Sample records for a-cyclodextrin inclusion compounds

  1. Solid-state studies and antioxidant properties of the γ-cyclodextrin·fisetin inclusion compound.

    PubMed

    Pais, Joana M; Barroca, Maria João; Marques, Maria Paula M; Almeida Paz, Filipe A; Braga, Susana S

    2017-01-01

    Fisetin is a natural antioxidant with a wide range of nutraceutical properties, including antidiabetic, neuroprotecting, and suppression or prevention of tumors. The present work describes the preparation of a water-soluble, solid inclusion compound of fisetin with gamma-cyclodextrin (γ-CD), a cyclic oligosaccharide approved for human consumption. A detailed physicochemical analysis of the product is carried out using elemental analysis, powder X-ray diffraction (PXRD), Raman, infrared and 13 C{ 1 H} CP-MAS NMR spectroscopies, and thermal analysis (TGA) to verify fisetin inclusion and to present a hypothetical structural arrangement for the host-guest units. The antioxidant activity of the γ-CD·fisetin inclusion compound is evaluated by the DPPH assay.

  2. In Situ Visualization of the Local Photothermal Effect Produced on α-Cyclodextrin Inclusion Compound Associated with Gold Nanoparticles.

    PubMed

    Silva, Nataly; Muñoz, Camila; Diaz-Marcos, Jordi; Samitier, Josep; Yutronic, Nicolás; Kogan, Marcelo J; Jara, Paul

    2016-12-01

    Evidence of guest migration in α-cyclodextrin-octylamine (α-CD-OA) inclusion compound (IC) generated via plasmonic heating of gold nanoparticles (AuNPs) has been studied. In this report, we demonstrate local effects generated by laser-mediated irradiation of a sample of AuNPs covered with inclusion compounds on surface-derivatized glass under liquid conditions by atomic force microscopy (AFM). Functionalized AuNPs on the glass and covered by the ICs were monitored by recording images by AFM during 5 h of irradiation, and images showed that after irradiation, a drastic decrease in the height of the AuNPs occurred. The absorption spectrum of the irradiated sample showed a hypsochromic shift from 542 to 536 nm, evidence suggesting that much of the population of nanoparticles lost all of the parts of the overlay of ICs due to the plasmonic heat generated by the irradiation. Mass spectrometry matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) performed on a sample containing a collection of drops obtained from the surface of the functionalized glass provided evidence that the irradiation lead to disintegration of the ICs and therefore exit of the octylamine molecule (the guest) from the cyclodextrin cavity (the matrix). Graphical Abstract Atomic Force Microscopy observation of the disintegration of a cyclodextrin inclusion compound by gold nanoparticles photothermal effect.

  3. Stability and spatial arrangement of the 2,4-dichlorophenoxyacetic acid and β-cyclodextrin inclusion compound: A theoretical study

    NASA Astrophysics Data System (ADS)

    Pereira, Robson A.; Anconi, Cleber P. A.; Nascimento, Clebio S.; De Almeida, Wagner B.; Dos Santos, Hélio F.

    2015-07-01

    The present letter reports results from a comprehensive theoretical analysis of the inclusion process involving 2,4-dichlorophenoxyacetic acid (2,4-D) and β-cyclodextrin (β-CD) for which the experimental data of formation is available. Spatial arrangement and stabilization energies were evaluated in gas phase and aqueous solution through density functional theory (DFT) and through the use of SMD implicit solvation approach. The discussed methodology was applied to predict the stability and identify the most favorable form (deprotonated or neutral) as well as the most probable spatial arrangement of the studied inclusion compound.

  4. In Situ Visualization of the Local Photothermal Effect Produced on α-Cyclodextrin Inclusion Compound Associated with Gold Nanoparticles

    NASA Astrophysics Data System (ADS)

    Silva, Nataly; Muñoz, Camila; Diaz-Marcos, Jordi; Samitier, Josep; Yutronic, Nicolás; Kogan, Marcelo J.; Jara, Paul

    2016-04-01

    Evidence of guest migration in α-cyclodextrin-octylamine (α-CD-OA) inclusion compound (IC) generated via plasmonic heating of gold nanoparticles (AuNPs) has been studied. In this report, we demonstrate local effects generated by laser-mediated irradiation of a sample of AuNPs covered with inclusion compounds on surface-derivatized glass under liquid conditions by atomic force microscopy (AFM). Functionalized AuNPs on the glass and covered by the ICs were monitored by recording images by AFM during 5 h of irradiation, and images showed that after irradiation, a drastic decrease in the height of the AuNPs occurred. The absorption spectrum of the irradiated sample showed a hypsochromic shift from 542 to 536 nm, evidence suggesting that much of the population of nanoparticles lost all of the parts of the overlay of ICs due to the plasmonic heat generated by the irradiation. Mass spectrometry matrix-assisted laser desorption/ionization-time-of-flight (MALDI-TOF) performed on a sample containing a collection of drops obtained from the surface of the functionalized glass provided evidence that the irradiation lead to disintegration of the ICs and therefore exit of the octylamine molecule (the guest) from the cyclodextrin cavity (the matrix).

  5. Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene.

    PubMed

    Lumholdt, Ludmilla; Fourmentin, Sophie; Nielsen, Thorbjørn T; Larsen, Kim L

    2014-01-01

    Polypropylene nonwovens were functionalised using a self-assembled, amphiphilic cyclodextrin coating and the potential for water purification by removal of pollutants was studied. As benzene is one of the problematic compounds in the Water Framework Directive, six volatile organic compounds (benzene and five benzene-based substances) were chosen as model compounds. The compounds were tested as a mixture in order to provide a more realistic situation since the wastewater will be a complex mixture containing multiple pollutants. The volatile organic compounds are known to form stable inclusion complexes with cyclodextrins. Six different amphiphilic cyclodextrin derivatives were synthesised in order to elucidate whether or not the uptake abilities of the coating depend on the structure of the derivative. Headspace gas chromatography was used for quantification of the uptake exploiting the volatile nature of benzene and its derivatives. The capacity was shown to increase beyond the expected stoichiometries of guest-host complexes with ratios of up to 16:1.

  6. Cyclodextrin-based microsensor for volatile organic compounds

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Swanson, B.I.; Li, D.Q.

    1996-12-31

    The direct covalent attachment of modified {alpha}- and {beta}-cyclodextrin on oxide surfaces has been studied for application in chemical sensors. First, oxide surfaces were treated with a silane coupling layer followed by the addition of cyclodextrin to form a self-assembled monolayer (SAM) of host receptors. Second, the oxide surfaces were reacted with a sol-gel (SG) precursor based on cyclodextrin structure to form a thick film with defined hydrophobic cyclodextrin cavities. The sensing properties of both films (SAM and SG) were examined with surface acoustic wave (SAW) measurement platform. Molecular interactions between an organic guest and a host thin-film on amore » 200 MHZ SAW resonator are being studied as a method of tracking and recognizing the presence of volatile organics. Surface acoustic wave sensors based on the inclusion chemistry of the bucket-type (cyclodextrin) molecules, were capable of detecting volatile organic compounds (VOCs) down to ppb levels. Because the nature of the interactions is moderate but noncovalent, detection of these VOCs was possible using a reversible real-time mode. Pattern recognition with an array of complementary microsensors appears to be a viable approach for identifying and quantifying VOCs. Recent results using optical waveguides for sensor transduction will also be discussed.« less

  7. Formation of β-Cyclodextrin inclusion compound with doxycycline: A theoretical approach

    NASA Astrophysics Data System (ADS)

    Peraro, Cristian R.; Anconi, Amanda C. S. A.; Anconi, Cleber P. A.

    2018-01-01

    Recently, the inclusion compound formed by doxycycline and modified CD was investigated. In the inclusion compound, the unstable site of doxycycline was protected by the hydrophobic CD cavity. However, the guest arrangement inside CD cavity has not identified. In some situations, the correlation between protons of the guest and host in a 2D-ROESY experiment can be compatible with head and tail spatial arrangements. In the present work, the most stable guest spatial arrangement for the inclusion of doxycycline into β-CD was evaluated at B97-D/6-311++(2d,p) level of theory. For sake of comparison, tetracycline inclusion compound was also studied.

  8. Spectroscopic methods for aqueous cyclodextrin inclusion complex binding measurement for 1,4-dioxane, chlorinated co-contaminants, and ozone

    NASA Astrophysics Data System (ADS)

    Khan, Naima A.; Johnson, Michael D.; Carroll, Kenneth C.

    2018-03-01

    Recalcitrant organic contaminants, such as 1,4-dioxane, typically require advanced oxidation process (AOP) oxidants, such as ozone (O3), for their complete mineralization during water treatment. Unfortunately, the use of AOPs can be limited by these oxidants' relatively high reactivities and short half-lives. These drawbacks can be minimized by partial encapsulation of the oxidants within a cyclodextrin cavity to form inclusion complexes. We determined the inclusion complexes of O3 and three common co-contaminants (trichloroethene, 1,1,1-trichloroethane, and 1,4-dioxane) as guest compounds within hydroxypropyl-β-cyclodextrin. Both direct (ultraviolet or UV) and competitive (fluorescence changes with 6-p-toluidine-2-naphthalenesulfonic acid as the probe) methods were used, which gave comparable results for the inclusion constants of these species. Impacts of changing pH and NaCl concentrations were also assessed. Binding constants increased with pH and with ionic strength, which was attributed to variations in guest compound solubility. The results illustrate the versatility of cyclodextrins for inclusion complexation with various types of compounds, binding measurement methods are applicable to a wide range of applications, and have implications for both extraction of contaminants and delivery of reagents for treatment of contaminants in wastewater or contaminated groundwater.

  9. Improvement of drug loading onto ion exchange resin by cyclodextrin inclusion complex.

    PubMed

    Samprasit, Wipada; Rojanarata, Theerasak; Akkaramongkolporn, Prasert; Ngawhirunpat, Tanasait; Sila-on, Warisada; Opanasopit, Praneet

    2013-11-01

    Ion exchange resins have ability to exchange their counter ions for ionized drug in the surrounding medium, yielding "drug resin complex." Cyclodextrin can be applied for enhancement of drug solubility and stability. Cyclodextrin inclusion complex of poorly water-soluble NSAIDs, i.e. meloxicam and piroxicam, was characterized and its novel application for improving drug loading onto an anionic exchange resin, i.e. Dowex® 1×2, was investigated. β-Cyclodextrin (β-CD) and hydroxypropyl β-cyclodextrin (HP-β-CD) were used for the preparation of inclusion complex with drugs in solution state at various pH. The inclusion complex was characterized by phase solubility, continuous variation, spectroscopic and electrochemistry methods. Then, the drug with and without cyclodextrin were equilibrated with resin at 1:1 and 1:2 weight ratio of drug and resin. Solubility of the drugs was found to increase with increasing cyclodextrin concentration and pH. The increased solubility was explained predominantly due to the formation of inclusion complex at low pH and the increased ionization of drug at high pH. According to characterization studies, the inclusion complex was successfully formed with a 1:1 stoichiometry. The presence of cyclodextrin in the loading solution resulted in the improvement of drug loading onto resin. Enhancing drug loading onto ion-exchange resin via the formation of cyclodextrin inclusion complex is usable in the development of ion-exchange based drug delivery systems, which will beneficially reduce the use of harmful acidic or basic and organic chemicals.

  10. 1H NMR study of inclusion compounds of phenylurea derivatives in β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Dupuy, N.; Barbry, D.; Bria, M.; Marquis, S.; Vrielynck, L.; Kister, J.

    2005-04-01

    Proton nuclear magnetic resonance spectroscopy ( 1H NMR), which has become an important tool for the study "in situ" of β-cyclodextrin (β-CD) complexes, was used to study and structurally characterize the inclusion complexes formed between β-CD and isoproturon, fenuron, monuron and diuron. The high variation of the chemical shifts from the proton located inside the cavity (H-3, H-5 and H-6) coupled with the non variation of the one located outer sphere of the β-CD (H-1, H-2 and H-4) provided clear evidence of the inclusion phenomena. Two-dimensional rotating frame Overhauser effect spectroscopy (ROESY) experiments were carried out to further support the proposed inclusion mode.

  11. Supramolecular Inclusion in Cyclodextrins: A Pictorial Spectroscopic Demonstration

    ERIC Educational Resources Information Center

    Haldar, Basudeb; Mallick, Arabinda; Chattopadhyay, Nitin

    2008-01-01

    A spectroscopic experiment is presented that reveals that the hydrophobically end-modified water-soluble polymeric fluorophore, pyrene end-capped poly(ethylene oxide) (PYPY), interacts differently with [alpha], [beta], and [gamma]-cyclodextrins (CD) to form supramolecular inclusion complexes. The emission spectrum of PYPY in aqueous solution shows…

  12. Study on vitamin K 3-cyclodextrin inclusion complex and analytical application

    NASA Astrophysics Data System (ADS)

    Zhenming, Dong; Xiuping, Liu; Guomei, Zhang; Shaomin, Shuang; Jinghao, Pan

    2003-07-01

    The inclusion interaction of the complexes between Vitamin K3 (VK3) and β-cyclodextrin (β-CD), hydroxypropyl-β-cyclodextrin (HP-β-CD) and sulfobutylether-β-cyclodextrin (SBE-β-CD) were studied by using steady-state fluorescence measurements. The various factors affecting the inclusion process were examined in detail. The formation constants and inclusion stoichiometry for VK3-CDs were determined. The results showed that the inclusion ability of β-CD and its derivatives was the order: SBE-β-CD>HP-β-CD>β-CD. The related inclusion mechanism is proposed to explain the inclusion process. A method of determining VK3 was established with the linear range was 2.5×10-6-5.0×10-4 M, and was used to determine the VK3 tablets. The recoveries were in the range of 97.52-103.5%. The results were satisfactory.

  13. Ketoprofen-β-cyclodextrin inclusion complexes formation by supercritical process technology

    NASA Astrophysics Data System (ADS)

    Sumarno, Rahim, Rizki; Trisanti, Prida Novarita

    2017-05-01

    Ketoprofen was a poorly soluble which anti-inflammatory, analgesic and antipyretic drug, solubility of which can be enchanced by form complexation with β-cyclodextrin. Besides that, the inclusion complex reduces the incidence of gastrointestinal side effect of drug. The aims of this research are to study the effect of H2O concentration in the supercritical carbondioxide and operation condition in the formation of ketoprofen-β-Cyclodextrin inclusion complex. This research was began by dissolved H2O in supercritical CO2 at 40°C and various saturation pressures. Then, dissolved H2O contacted with (1:5 w/w) ketoprofen-β-Cyclodextrin mixture at 50°C and various operation pressures. It called saturation process. Saturation was done for ±2 hours with agitation process and continued by decompression process. The products were characterized by drug Release, Differential Scanning Calorimetry (DCS) dan Scanning Electron Microscopy (SEM) analyses. The percentage from this work were 76,82%-89,99% for inclusion complexes. The percentage drug release of ketoprofen were 82,83%-88,36% on various inclusion pressure and various inclusion period.

  14. Enhanced transport of low-polarity organic compounds through soil by cyclodextrin

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Brusseau, M.L.; Wang, X.; Hu, Q.

    1994-05-01

    The removal of low-polarity organic compounds from soils and aquifers by water flushing is often constrained by sorption interactions. There is great interest in developing systems that can enhance the transport of organic compounds through porous media, thus facilitating remediation. We investigated the potential of hydroxypropyl-[beta]-cyclodextrin (HPCD), a microbially produced compound, to reduce the sorption and to enhance the transport of several low-polarity organic compounds. The results show that cyclodextrin does not interact with the two porous media used in the study. As a result, there is no retardation of cyclodextrin during transport. The retardation of compounds such as anthracene,more » pyrene, and trichlorobiphenyl was significantly (orders of magnitude) reduced in the presence of cyclodextrin. The enhancement effect of the cyclodextrin was predictable with a simple equation based on three-phase partitioning. The nonreactive nature of cyclodextrin combined with its large affinity for low-polarity organic compounds makes cyclodextrin a possible candidate for use in in-situ remediation efforts. 22 refs., 6 figs., 3 tabs.« less

  15. Inclusion complexes of azadirachtin with native and methylated cyclodextrins: solubilization and binding ability.

    PubMed

    Liu, Yu; Chen, Guo-Song; Chen, Yong; Lin, Jun

    2005-06-02

    The inclusion complexation behavior of azadirachtin with several cyclodextrins and their methylated derivatives has been investigated in both solution and the solid state by means of XRD, TG-DTA, DSC, NMR, and UV-vis spectroscopy. The results show that the water solubility of azadirachtin was obviously increased after resulting inclusion complex with cyclodextrins. Typically, beta-cyclodextrin (beta-CD), dimethyl-beta-cyclodextrin (DMbetaCD), permethyl-beta-cyclodextrin (TMbetaCD), and hydroxypropyl-beta-cyclodextrin (HPbetaCD) are found to be able to solubilize azadirachtin to high levels up to 2.7, 1.3, 3.5, and 1.6 mg/mL (calculated as azadirachtin), respectively. This satisfactory water solubility and high thermal stability of the cyclodextrin-azadirachtin complexes, will be potentially useful for their application as herbal medicine or healthcare products.

  16. Inclusion complexes of β-cyclodextrin-dinitrocompounds as UV absorber for ballpoint pen ink.

    PubMed

    Srinivasan, Krishnan; Radhakrishnan, S; Stalin, Thambusamy

    2014-08-14

    2,4-Dinitrophenol (2,4-DNP), 2,4-dinitroaniline (2,4-DNA), 2,6-dinitroaniline (2,6-DNA) and 2,6-dinitrobenzoic acid (2,6-DNB) has appeared for the UV absorption bands in different wavelength region below 400 nm, a combination of these dinitro aromatic compounds gave the broad absorption spectra within the UV region. The absorption intensities have been increased by preparation of the inclusion complex of dinitro compounds with β-cyclodextrin (β-CD). Prepared inclusion complexes are used to improve the UV protection properties of the ball point pen ink against photo degradation. The formation of solid inclusion complexes was characterized by FT-IR, and (1)H NMR spectroscopy. The UV protecting properties of these inclusion complexes were calculated their sun protection factor (SPF) is also discussed. The stability of the ballpoint pen ink has been confirmed by UV-Visible spectroscopic method. Copyright © 2014 Elsevier B.V. All rights reserved.

  17. The effect of solvent interactions on alpha-, beta-, and gamma-cyclodextrin/flavor molecular inclusion complexes.

    PubMed

    Reineccius, Teresa A; Reineccius, Gary A; Peppard, Terry L

    2005-01-26

    Three commonly used flavor industry solvents (propylene glycol, triacetin, and triethyl citrate) were tested for their capacity to interfere with the ability of alpha-, beta-, and gamma-cyclodextrin to form molecular inclusion complexes with flavors. Six flavor compounds (ethyl butyrate, ethyl heptanoate, l-menthol, methyl anthranilate, neral, and geranial) were measured by headspace gas chromatography above 2:1 water/ethanol containing appropriate additions of cyclodextrin and flavor solvent. The smallest and most polar solvent molecule represented by propylene glycol had the least effect on cyclodextrin/flavorant complex formation. In contrast, triacetin, intermediate in size among the three flavor diluents studied, had the greatest effect, even though, based on at least some computed molecular parameters, it appears to be more polar than triethyl citrate. The explanation for this apparent anomaly may lie in differences in the extent to which triacetin and triethyl citrate are able to interact with cyclodextrins by means of partial interaction with the hydrophobic cavities of the latter.

  18. Crystal structures and molecular dynamics studies of the inclusion compounds of β-citronellol in β-cyclodextrin, heptakis(2,6-di-O-methyl)-β-cyclodextrin and heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Fourtaka, Katerina; Christoforides, Elias; Mentzafos, Dimitris; Bethanis, Kostas

    2018-06-01

    The crystal structures of the inclusion complexes of the β-citronellol (cl) inβ-Cyclodextrin (β-CD), heptakis(2,6-di-O-methyl)-β-Cyclodextrin (DM-β-CD) and heptakis(2,3,6-tri-O-methyl)-β-Cyclodextrin (TM-β-CD) have being investigated by X-ray crystallography. The cl/β-CD inclusion complex crystallizes in the P1space group forming dimers which are arranged along the c-axis according to the Intermediate Channel packing mode. Inside the dimeric host cavity two enantiomeric guest molecules are accommodated. The inclusion complexes of cl/DM-β-CD and cl/TM-β-CD crystallize in the P212121 space group having both 1:1 guest:host stoichiometry, the guest found always with the (-)-cl enantiomeric configuration. The guest is fully encapsulated inside the DM-β-CD host cavity whereas is partially encapsulated in the TM-β-CD which is severely puckered as in all TM-β-CD complexes and its primary side is efficiently blocked by the methoxy groups. The complex units in the case of cl/DM-β-CD pack along the crystallographic a-axis in a head-to-tail manner forming columns of herringbone mode whereas in the case of cl/TM-β-CD are arranged also head-to-tail, parallel to the b-axis, in a screw-channel mode. MD simulations based on the determined crystal structures showed that in a simulated aqueous environment the guest maintains the inclusion mode observed crystallographically in every case. MM/GBSA-calculations used for comparison of the inclusion complexes binding affinity with each other, indicated that the inclusion of β-citronellol in TM-β-CD is less favorable than in β-CD and DM-β-CD.

  19. Study of β-cyclodextrin inclusion complexes with volatile molecules geraniol and α-terpineol enantiomers in solid state and in solution

    NASA Astrophysics Data System (ADS)

    Ceborska, Magdalena; Szwed, Kamila; Asztemborska, Monika; Wszelaka-Rylik, Małgorzata; Kicińska, Ewa; Suwińska, Kinga

    2015-11-01

    Geraniol and α-terpineol are insoluble in water volatile compounds. α-Terpineol is a potentially important agent for medical applications. Formation of molecular complexes with β-cyclodextrin would lead to the increase of water solubility and bioavailability. β-Cyclodextrin forms 2:2 inclusion complexes with both enantiomers of α-terpineol and their precursor geraniol. Solid state complexes are thoroughly characterized by single X-ray crystallography and their stability over vast range of temperatures is proven by TG analysis. Intermolecular host-guest, host-host and guest-guest interactions give good insight into the nature of formed inclusion complexes. Stability constants of the complexes in solution are determined by HPLC.

  20. Solubility Enhancement of Steviol Glycosides and Characterization of Their Inclusion Complexes with Gamma-Cyclodextrin

    PubMed Central

    Upreti, Mani; Strassburger, Ken; Chen, You L.; Wu, Shaoxiong; Prakash, Indra

    2011-01-01

    Steviol glycosidesrebaudioside (reb) A, C and D have low aqueous solubilities. To improve their aqueous solubilities, inclusion complex of steviol glycosides, reb A, C and D and gamma cyclodextrin were prepared by freeze drying method and further characterized by means of differential scanning calorimetry, Fourier transform infrared spectroscopy and Raman spectroscopy. The effect of gamma cyclodextrin on chemical shifts of the steviol glycosides was also studied in proton NMR experiments as well as in solid state 13C CP/MAS NMR experiments. These results indicated that the steviol glycosides were clearly in inclusion complex formation with the gamma cyclodextrin which also results in solubility enhancement of these steviol glycosides. Phase solubility studies showed that amounts of soluble reb A, C and D increased with increasing amounts of gamma cyclodextrin indicating formation of 1:1 stoichiometric and higher order inclusion complexes. PMID:22174615

  1. Hot-melt extrusion as a continuous manufacturing process to form ternary cyclodextrin inclusion complexes.

    PubMed

    Thiry, Justine; Krier, Fabrice; Ratwatte, Shenelka; Thomassin, Jean-Michel; Jerome, Christine; Evrard, Brigitte

    2017-01-01

    The aim of this study was to evaluate hot-melt extrusion (HME) as a continuous process to form cyclodextrin (CD) inclusion complexes in order to increase the solubility and dissolution rate of itraconazole (ITZ), a class II model drug molecule of the Biopharmaceutics Classification System. Different CD derivatives were tested in a 1:1 (CD:ITZ) molar ratio to obtain CD ternary inclusion complexes in the presence of a polymer, namely Soluplus ® (SOL). The CD used in this series of experiments were β-cyclodextrin (βCD), hydroxypropyl-β-cyclodextrin (HPβCD) with degrees of substitution of 0.63 and 0.87, randomly methylated β-cyclodextrin (Rameb ® ), sulfobutylether-β-cyclodextrin (Captisol ® ) and methyl-β-cyclodextrin (Crysmeb ® ). Rheology testing and mini extrusion using a conical twin screw mini extruder were performed to test the processability of the different CD mixtures since CD are not thermoplastic. This allowed Captisol ® and Crysmeb ® to be discarded from the study due to their high impact on the viscosity of the SOL/ITZ mixture. The remaining CD were processed by HME in an 18mm twin screw extruder. Saturation concentration measurements confirmed the enhancement of solubility of ITZ for the four CD formulations. Biphasic dissolution tests indicated that all four formulations had faster release profiles compared to the SOL/ITZ solid dispersion. Formulations of HPβCD 0.63 and Rameb ® even reached 95% of ITZ released in both phases after 1h. The formulations were characterized using thermal differential scanning calorimetry and attenuated total reflectance infra-red analysis. These analyses confirmed that the increased release profile was due to the formation of ternary inclusion complexes. Copyright © 2016 Elsevier B.V. All rights reserved.

  2. Piroxicam/2-hydroxypropyl-beta-cyclodextrin inclusion complex prepared by a new fluid-bed coating technique.

    PubMed

    Zhang, Xingwang; Wu, Danni; Lai, Jie; Lu, Yi; Yin, Zongning; Wu, Wei

    2009-02-01

    This work was aimed at investigating the feasibility of fluid-bed coating as a new method to prepare cyclodextrin inclusion complex. The inclusion complex of the model drug piroxicam (PIX) and 2-hydroxypropyl-beta-cyclodextrin (HPCD) in aqueous ethanol solution was sprayed and deposited onto the surface of the pellet substrate upon removal of the solvent. The coating process was fluent with high coating efficiency. Scanning electron microscopy revealed a coarse pellet surface, and a loosely packed coating structure. Significantly enhanced dissolution, over 90% at 5 min, was observed at stoichiometric PIX/HPCD molar ratio (1/1) and at a ratio with excessive HPCD (1/2). Differential scanning calorimetry and powder X-ray diffractometry confirmed absence of crystallinity of PIX at PIX/HPCD molar ratio of 1/1 and 1/2. Fourier transform-infrared spectrometry and Raman spectrometry revealed interaction between PIX and HPCD adding evidence on inclusion of PIX moieties into HPCD cavities. Solid-state (13)C NMR spectrometry indicated possible inclusion of PIX through the pyridine ring. It is concluded that fluid-bed coating has potential to be used as a new technique to prepare cyclodextrin inclusion complex.

  3. Inclusion complex of novel curcumin analogue CDF and β-cyclodextrin (1:2) and its enhanced in vivo anticancer activity against pancreatic cancer.

    PubMed

    Dandawate, Prasad R; Vyas, Alok; Ahmad, Aamir; Banerjee, Sanjeev; Deshpande, Jyoti; Swamy, K Venkateswara; Jamadar, Abeda; Dumhe-Klaire, Anne Catherine; Padhye, Subhash; Sarkar, Fazlul H

    2012-07-01

    Several formulations have been proposed to improve the systemic delivery of novel cancer therapeutic compounds, including cyclodextrin derivatives. We aimed to synthesize and characterize of CDF-β-cyclodextrin inclusion complex (1:2) (CDFCD). The compound was characterized by Fourier transform infrared, differential scanning calorimetry, powder X-ray diffraction studies, H1 & C13 NMR studies and scanning electron microscopic analysis. Its activity was tested against multiple cancer cell lines, and in vivo bioavailability was checked. CDF-β-cyclodextrin was found to lower IC(50) value by half when tested against multiple cancer cell lines. It preferentially accumulated in the pancreas, where levels of CDF-β-cyclodextrin in mice were 10 times higher than in serum, following intravenous administration of an aqueous CDF-β-cyclodextrin preparation. Novel curcumin analog CDF preferentially accumulates in the pancreas, leading to its potent anticancer activity against pancreatic cancer cells. Synthesis of such CDF-β-cyclodextrin self-assembly is an effective strategy to enhance its bioavailability and tissue distribution, warranting further evaluation for CDF delivery in clinical settings for treatment of human malignancies.

  4. Inclusion compound of vitamin B6 in β-CD. Physico-chemical and structural investigations

    NASA Astrophysics Data System (ADS)

    Borodi, Gheorghe; Kacso, Irina; Farcaş, Sorin I.; Bratu, Ioan

    2009-08-01

    Structural and physico-chemical characterization of supramolecular assembly of vitamin B6 with β-cyclodextrin (β-CD) prepared by different methods (kneading, co-precipitation and freeze-drying) has been performed by using several spectroscopic techniques (FTIR, 1H NMR, UV-Vis), powder X-ray diffraction and DSC in order to evidence the inclusion compound formation. An analysis of the chemical shifts observed in the 1H-NMR spectra and of the vibrational frequency shifts led to the tentative conclusion that the vitamin B6 probably enters the cyclodextrin torus when forming the β-CD-vitamin B6 inclusion complex.

  5. Production, Characterization, and Stability of Orange or Eucalyptus Essential Oil/β-Cyclodextrin Inclusion Complex.

    PubMed

    Kringel, Dianini Hüttner; Antunes, Mariana Dias; Klein, Bruna; Crizel, Rosane Lopes; Wagner, Roger; de Oliveira, Roberto Pedroso; Dias, Alvaro Renato Guerra; Zavareze, Elessandra da Rosa

    2017-11-01

    The aim of this study was to produce and characterize inclusion complexes (IC) between β-cyclodextrin (β-CD) and orange essential oil (OEO) or eucalyptus essential oil (EEO), and to compare these with their pure compounds and physical mixtures. The samples were evaluated by chemical composition, morphology, thermal stability, and volatile compounds by static headspace-gas chromatography (SH-GC). Comparing the free essential oil and physical mixture with the inclusion complex, of both essential oils (OEO and EEO), it was observed differences occurred in the chemical composition, thermal stability, and morphology. These differences show that there was the formation of the inclusion complex and demonstrate the necessity of the precipitation method used to guarantee the interaction between β-CD and essential oils. The slow loss of the volatile compounds from both essential oils, when complexed with β-CD, showed a higher stability when compared with their physical mixtures and free essential oils. Therefore, the results showed that the chemical composition, molecular size, and structure of the essential oils influence the characteristics of the inclusion complexes. The application of the β-CD in the formation of inclusion complexes with essential oils can expand the potential applications in foods. © 2017 Institute of Food Technologists®.

  6. Study on the inclusion complex between β-cyclodextrin derivatives and flurbiprofen by spectrofluorometric

    NASA Astrophysics Data System (ADS)

    Miao, Jiabing; Guo, Zhaohua; Wang, Yongwang; Chen, Dong; Li, Yifan; Zhang, Feng

    2017-08-01

    The inclusion behavior between β-cyclodextrin derivatives (β-CDs) and flurbiprofen had been studied by fluorescence spectrophotometry. The effects of type and concentration of β-CDs; ionic strength; pH as well as temperature on inclusion behavior were investigated. And then the thermodynamic parameters ΔH/ΔS and ΔG of the inclusion complex of flurbiprofen and HP-β-CD were calculated, the driving force of the inclusion reaction had been also certified. The experimental results indicate, the fluorescence intensity (F) of flurbiprofen increases with the raising of β-CDs concentration, among the studied types of β-cyclodextrin derivatives, hydroxypropy l-β-cyclodextrin (HP-β-CD) has the most obvious enhancement, namely HP-β-CD has the strongest ability to complex with flurbiprofen. Plot of 1/ (F-F0) against 1/ [β-CD] yields a straight line, indicating 1:1 stoichiometric complex formed between β-CDs and flurbiprofen. Inclusion constant is enhanced with the increase in ionic strength of solution, whereas followes an opposite tendency with the rise of pH value. In the inclusive process, under normal temperature ΔG<0, it illustrates that this process is spontaneous, and the driving force is the change of enthalpy.

  7. Cyclodextrin Inclusion Complex to Improve Physicochemical Properties of Herbicide Bentazon: Exploring Better Formulations

    PubMed Central

    Yáñez, Claudia; Cañete-Rosales, Paulina; Castillo, Juan Pablo; Catalán, Nicole; Undabeytia, Tomás; Morillo, Esmeralda

    2012-01-01

    The knowledge of the host-guest complexes using cyclodextrins (CDs) has prompted an increase in the development of new formulations. The capacity of these organic host structures of including guest within their hydrophobic cavities, improves physicochemical properties of the guest. In the case of pesticides, several inclusion complexes with cyclodextrins have been reported. However, in order to explore rationally new pesticide formulations, it is essential to know the effect of cyclodextrins on the properties of guest molecules. In this study, the inclusion complexes of bentazon (Btz) with native βCD and two derivatives, 2-hydroxypropyl-β-cyclodextrin (HPCD) and sulfobutylether-β-cyclodextrin (SBECD), were prepared by two methods: kneading and freeze-drying, and their characterization was investigated with different analytical techniques including Fourier transform infrared spectroscopy (FT-IR), differential thermal analysis (DTA), X-ray diffractometry (XRD) and differential pulse voltammetry (DPV). All these approaches indicate that Btz forms inclusion complexes with CDs in solution and in solid state, with a stoichiometry of 1∶1, although some of them are obtained in mixtures with free Btz. The calculated association constant of the Btz/HPCD complex by DPV was 244±19 M−1 being an intermediate value compared with those obtained with βCD and SBECD. The use of CDs significantly increases Btz photostability, and depending on the CDs, decreases the surface tension. The results indicated that bentazon forms inclusion complexes with CDs showing improved physicochemical properties compared to free bentazon indicating that CDs may serve as excipient in herbicide formulations. PMID:22952577

  8. Inclusion complex of benzocaine and β-cyclodextrin: 1H NMR and isothermal titration calorimetry studies

    NASA Astrophysics Data System (ADS)

    Mic, Mihaela; Pırnǎu, Adrian; Bogdan, Mircea; Turcu, Ioan

    2013-11-01

    The supramolecular structure of the inclusion complex of β-cyclodextrin with benzocaine in aqueous solution has been investigated by 1H NMR spectroscopy and isothermal titration nanocalorimetry (ITC). Analysis of 1H NMR data by continuous variation method indicates that the benzocaine: β-cyclodextrin inclusion complex occurs and has a 1:1 stoichiometry. Rotating frame NOE spectroscopy (ROESY) was used to ascertain the solution geometry of the host-guest complex which indicates that the benzocaine molecule was included with the aromatic ring into the cyclodextrin cavity. Although the affinity of benzocaine for cyclodextrin is relatively high, the association constant cannot be measured using ITC due to the low solubility of benzocaine in water.

  9. Preparation, characterization and in vitro evaluation of a new nucleotide analogue prodrug cyclodextrin inclusion complexes.

    PubMed

    Diab, Roudayna; Jordheim, Lars P; Degobert, Ghania; Peyrottes, Suzanne; Périgaud, Christian; Dumontet, Charles; Fessi, Hatem

    2009-01-01

    Bis(tbutyl-S-acyl-2-thioethyl)-cytidine monophosophate is a new cytotoxic mononucleotide prodrug which have been developed to reverse the cellular resistance to nucleoside analogues. Unfortunately, its in vivo utilisation was hampered by its poor water solubility, raising the need of a molecular vector capable to mask its physicochemical characteristics although without affecting its cytotoxic activity. Hydroxypropyl-beta-cyclodextrin was used to prepare the prodrug inclusion complexes, allowing it to be solubilized in water and hence to be used for in vitro and in vivo experiments. A molar ratio of the cyclodextrin: prodrug of 3 was sufficient to obtain complete solubilization of the prodrug. The inclusion complex was characterized by differential scanning calorimetry, which revealed the disappearance of the melting peak of the prodrug suggesting the formation of inclusion complex. Proton Nuclear Magnetic Resonance spectroscopy provided a definitive proof of the inclusion complex formation, which was evidenced by the large chemical shift displacements observed for protons located in the interior of the hydrophobic cyclodextrin cavity. The complex retained its cytotoxic activity as shown by in vitro cell survival assays on murine leukemia cells. These results provided a basis for potential therapeutic applications of co-formulation of this new nucleotide analogue with hydroxypropyl-beta-CD in cancer therapy.

  10. Empirical, thermodynamic and quantum-chemical investigations of inclusion complexation between flavanones and (2-hydroxypropyl)-cyclodextrins.

    PubMed

    Liu, Benguo; Li, Wei; Nguyen, Tien An; Zhao, Jian

    2012-09-15

    The inclusion complexation of (2-hydroxypropyl)-cyclodextrins with flavanones was investigated by phase solubility measurements, as well as thermodynamic and quantum chemical methods. Inclusion complexes were formed between (2-hydroxypropyl)-α-cyclodextrin (HP-α-CD), (2-hydroxypropyl)-β-cyclodextrin (HP-β-CD), (2-hydroxypropyl)-γ-cyclodextrin (HP-γ-CD) and β-cyclodextrin (β-CD) and four flavanones (naringenin, naringin, hesperetin and dihydromyricetin) in aqueous solutions and their phase solubility was determined. For all the flavanones, the stability constants of their complexes formed with different CDs followed the rank order: HP-β-CD (MW 1540)>HP-β-CD (MW 1460)>HP-β-CD (MW 1380)>β-CD>HP-γ-CD>HP-α-CD. Experimental results and quantum chemical calculations showed that the ability of flavanones to form inclusion complex with (2-hydroxypropyl)-cyclodextrins was determined by both the steric effect and hydrophobicity of the flavanones. For flavanones that have similar molecular volumes, the hydrophobicity of the molecule was the main determining factor of its ability to form inclusion complexes with HP-β-CD, and the hydrophobicity parameter Log P is highly correlated with the stability constant of the complexes. Results of thermodynamic study demonstrated that hydrophobic interaction is the main driving force for the formation process of the flavanone-CD inclusion complexes. Quantum chemical analysis of the most active hydroxyl groups and HOMO (the highest occupied molecular orbital) showed that the B ring of the flavanones was most likely involved in hydrogen bonding with the side groups in the cavity of the CDs, through which the inclusion complex was stabilised. Copyright © 2012 Elsevier Ltd. All rights reserved.

  11. Synthesis, characterization and cytotoxic evaluation of inclusion complexes between Riparin A and β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Araújo, Éverton José Ferreira de; Silva, Oskar Almeida; Rezende-Júnior, Luís Mário; Sousa, Ian Jhemes Oliveira; Araújo, Danielle Yasmin Moura Lopes de; Carvalho, Rusbene Bruno Fonseca de; Pereira, Sean Telles; Gutierrez, Stanley Juan Chavez; Ferreira, Paulo Michel Pinheiro; Lima, Francisco das Chagas Alves

    2017-08-01

    This study performed a physicochemical characterization of the inclusion complex generated between Riparin A and β-cyclodextrin (Rip A/β-CD) and compared the cytotoxic potential of the incorporated Rip A upon Artemia salina larvae. Samples were analyzed by phase solubility diagram, dissolution profile, differential scanning calorimetry, X-ray diffraction, infrared spectroscopy, proton nuclear magnetic resonance, scanning electron microscopy and artemicidal action. Riparin A/β-cyclodextrin complexes presented increased water solubility, AL type solubility diagram and Kst constant of 373 L/mol. Thermal analysis demonstrated reduction of the melt peak of complexed Rip A at 116.2 °C. Infrared spectroscopy confirmed generation of inclusion complexes, 1H NMR pointed out the interaction with H-3 of β-CD cavities, alterations in the crystalline natures of Rip A when incorporated within β-CD were observed and inclusion complexes presented higher cytotoxic on A. salina nauplii, with CL50 value of 117.2 (84.9-161.8) μg/mL. So, Rip A was incorporated into β-CDs with high efficiency and water solubility of Rip A was improved. Such solubility was corroborated by cytotoxic evaluation and these outcomes support the improvement of biological properties for complexes between Riparin A/β-cyclodextrin.

  12. Host-guest inclusion system of glycyrrhetic acid with polyamine-β-cyclodextrin: Preparation, characterization, and anticancer activity

    NASA Astrophysics Data System (ADS)

    Shen, Zhi; Qin, Qi; Liao, Xiali; Yang, Bo

    2017-12-01

    The inclusion complexation behaviors of glycyrrhetic acid (CTA) with four polyamine-modified β-cyclodextrins (CDs) have been investigated by 1H and 2D NMR, thermal gravimetric analysis, X-ray power diffraction and scanning electron microscopy. The results showed that Glycyrrhetic acid was encapsulated into the cavity of cyclodextrin to form the complexes with 1:1 stoichiometry. The water solubility of GTA was significantly enhanced by inclusion complexation with polyamine-modified β-cyclodextrins. The calculated IC50 values indicated that the antitumor activities of inclusion complexes were better than that of GTA. Satisfactory aqueous solubility, along with high thermal stability of inclusion complexes will be potentially useful for their application on the formulation design of natural medicine.

  13. Diffusion coefficients in systems with inclusion compounds. 1. alpha. -Cyclodextrin-L-phenylalanine-water at 25 degree C

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Paduano, L.; Sartorio, R.; Vitagliano, V.

    Diffusion coefficients in the ternary system {alpha}-cyclodextrin (at one concentration)-L-phenylalanine (at four concentrations)-water have been measured by using the Gouy interferometric technique. The effect of the inclusion equilibrium on the cross-term diffusion coefficients was observed. The measured diffusion coefficients in the ternary systems were used to calculate values of the binding constants. These values are in good agreement with the value obtained from calorimetric studies.

  14. Nanoaggregation of inclusion complexes of glibenclamide with cyclodextrins.

    PubMed

    Lucio, David; Irache, Juan Manuel; Font, María; Martínez-Ohárriz, María Cristina

    2017-03-15

    Glibenclamide is a sulfonylurea used for the oral treatment of type II diabetes mellitus. This drug shows low bioavailability as consequence of its low solubility. In order to solve this problem, the interaction with cyclodextrin has been proposed. This study tries to provide an explanation about the processes involved in the formation of GB-βCDs complexes, which have been interpreted in different ways by several authors. Among native cyclodextrins, βCD presents the most appropriate cavity to host glibenclamide molecules showing A L solubility diagrams (K 1:1 ≈1700M -1 ). However, [Formula: see text] solubility profiles were found for βCD derivatives, highlighting the coexistence of several phenomena involved in the drug solubility enhancement. At low CD concentration, the formation of inclusion complexes can be studied and the stability constants can be calculated (K 1:1 ≈1400M -1 ). Whereas at high CD concentration, the enhancement of GB solubility would be mainly attributed to the formation of nanoaggregates of CD and GB-CD complexes (sizes between 100 and 300nm). The inclusion mode into βCD occurs through the cyclohexyl ring of GB, adopting a semi-folded conformation which maximizes the hydrogen bond network. As consequence of all these phenomena, a 150-fold enhancement of drug solubility has been achieved using β-cyclodextrin derivatives. Thus, its use has proven to be an interesting tool to improve the oral administration of glibenclamide in accordance with dosage bulk and dose/solubility ratio requirements. Copyright © 2017 Elsevier B.V. All rights reserved.

  15. Complexation of adamantyl compounds by beta-cyclodextrin and monoaminoderivatives.

    PubMed

    Carrazana, Jorge; Jover, Aida; Meijide, Francisco; Soto, Victor H; Vazquez Tato, José

    2005-05-19

    Since the beta-cyclodextrin cavity is not a smooth cone but has constrictions in the neighborhoods of the H3 and H5 atoms, the hypothesis that bulky hydrophobic guests can form two isomeric inclusion complexes (one of them, c(p), is formed by the entrance of the guest by the primary side of the cavity, and the other one, c(s), results from the entrance by the secondary side) is checked. Thus, the inclusion processes of two 1-substituted adamantyl derivatives (rimantidine and adamantylmethanol) with beta-cyclodextrin and its two monoamino derivatives at positions 6 (6-NH2beta-CD) and 3 (3-NH2beta-CD) were studied. From rotating-frame Overhauser enhancement spectroscopy experiments, it was deduced that both guests form c(s) complexes with beta-CD and 6-NH2beta-CD but c(p) complexes with 3-NH2beta-CD. In all cases, the hydrophilic group attached to the adamantyl residue protrudes toward the bulk solvent outside the cyclodextrin cavity. The thermodynamic parameters (free energy, equilibrium constant, enthalpy, and entropy) associated with the inclusion phenomena were measured by isothermal titration calorimetry experiments. From these results, the difference in the free energy for the formation of the two complexes, c(s) and c(p), for the same host/guest system has been estimated as being 11.5 +/- 0.8 kJ mol(-1). This large difference explains why under normal experimental conditions only one of the two complexes (c(s)) is detected. It is also concluded that a hyperboloid of revolution can be a better schematic picture to represent the actual geometry of the cyclodextrin cavities than the usual smooth cone or trapezium.

  16. Characterization of Cyclodextrin/Volatile Inclusion Complexes: A Review.

    PubMed

    Kfoury, Miriana; Landy, David; Fourmentin, Sophie

    2018-05-17

    Cyclodextrins (CDs) are a family of cyclic oligosaccharides that constitute one of the most widely used molecular hosts in supramolecular chemistry. Encapsulation in the hydrophobic cavity of CDs positively affects the physical and chemical characteristics of the guests upon the formation of inclusion complexes. Such a property is interestingly employed to retain volatile guests and reduce their volatility. Within this scope, the starting crucial point for a suitable and careful characterization of an inclusion complex is to assess the value of the formation constant (K f ), also called stability or binding constant. This task requires the application of the appropriate analytical method and technique. Thus, the aim of the present paper is to give a general overview of the main analytical tools used for the determination of K f values for CD/volatile inclusion complexes. This review emphasizes on the advantages, inconvenients and limits of each applied method. A special attention is also dedicated to the improvement of the current methods and to the development of new techniques. Further, the applicability of each technique is illustrated by a summary of data obtained from the literature.

  17. Stability of natamycin and its cyclodextrin inclusion complexes in aqueous solution.

    PubMed

    Koontz, John L; Marcy, Joseph E; Barbeau, William E; Duncan, Susan E

    2003-11-19

    Aqueous solutions of natamycin and its beta-cyclodextrin (beta-CD), hydroxypropyl beta-cyclodextrin, and gamma-cyclodextrin (gamma-CD) inclusion complexes were completely degraded after 24 h of exposure to 1000 lx fluorescent lighting at 4 degrees C. After 14 days of storage in darkness at 4 degrees C, 92.2% of natamycin remained in active form. The natamycin:beta-CD complex and natamycin:gamma-CD complex were significantly more stable (p < 0.05) than natamycin in its free state in aqueous solutions stored in darkness at 4 degrees C. Clear poly(ethylene terephthalate) packaging with a UV light absorber allowed 85.0% of natamycin to remain after 14 days of storage under 1000 lx fluorescent lighting at 4 degrees C. Natamycin:cyclodextrin complexes can be dissociated for analysis in methanol/water/acetic acid, 60:40:5, v/v/v. Natamycin and its complexes in dissociated form were quantified by reverse phase HPLC with detection by photodiode array at 304 nm.

  18. Microencapsulation of caffeic acid phenethyl ester and caffeic acid phenethyl amide by inclusion in hydroxypropyl-β-cyclodextrin.

    PubMed

    Garrido, E Manuela P J; Cerqueira, Ana S; Chavarria, Daniel; Silva, Tiago; Borges, Fernanda; Garrido, Jorge M P J

    2018-07-15

    Caffeic acid phenethyl ester (CAPE) is a bioactive polyphenolic compound obtained from propolis extract. Although it has a broad therapeutic potential, the bioavailability of CAPE is limited, due to reduced solubility and poor plasmatic stability. Efforts to reduce these pharmacokinetic drawbacks resulted in the synthesis of caffeic acid phenethyl amide (CAPA). Cyclodextrins have been proved as promising excipients for the formulation of active ingredients. Herein, we report the inclusion complexation behavior and binding ability of CAPE and CAPA with hydroxypropyl-β-cyclodextrin (HP-β-CD). The supramolecular interactions were examined through UV and FTIR spectroscopy, DSC, 1 H NMR and 2D ROESY. The CAPE/HP-β-CD and CAPA/HP-β-CD inclusion complexes stability constants were determined to be, respectively, 2911.6 and 584.6 M -1 in water and 2866.2 and 700.1 M -1 at physiological pH. The aqueous solubility increased notably, proving that HP-β-CD can be potentially useful to improve the biological, chemical and physical properties of CAPE and CAPA. Copyright © 2018 Elsevier Ltd. All rights reserved.

  19. Inclusion complexes of yellow bell pepper pigments with β-cyclodextrin: preparation, characterisation and application as food natural colorant.

    PubMed

    Lobo, Francine Albernaz Tf; Silva, Vitoria; Domingues, Josiane; Rodrigues, Silvana; Costa, Valéria; Falcão, Deborah; de Lima Araújo, Kátia G

    2018-05-01

    This work aimed to prepare inclusion complexes using yellow bell pepper pigments and β-cyclodextrin by two different procedures (method A, ultrasonic homogenisation; method B, kneading), to characterise them and evaluate their colour stability in an isotonic beverage model. The extract/β-cyclodextrin ratio was 1:2 for both inclusion methodologies evaluated. The formed extract-β-cyclodextrin complexes and a physical mixture of extract and β-cyclodextrin were evaluated by differential scanning calorimetry (DSC) and Fourier transform infrared spectroscopy (FTIR). Both methodologies resulted in good complex yield and inclusion efficiency. The colour indices L* (lightness), a* (green/red) and b* (blue/yellow) of isotonic drinks added with the complexes were measured during storage under irradiance (1400 lx) and in the absence of light at temperatures between 25 and 31 °C for 21 days. The complex obtained by inclusion method B promoted better colour protection for the beverage compared with the use of the crude extract, showing that the molecular inclusion of yellow bell pepper carotenoids can provide good results for that purpose. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

  20. Solid-state flurbiprofen and methyl-β-cyclodextrin inclusion complexes prepared using a single-step, organic solvent-free supercritical fluid process.

    PubMed

    Rudrangi, Shashi Ravi Suman; Kaialy, Waseem; Ghori, Muhammad U; Trivedi, Vivek; Snowden, Martin J; Alexander, Bruce David

    2016-07-01

    The aim of this study was to enhance the apparent solubility and dissolution properties of flurbiprofen through inclusion complexation with cyclodextrins. Especially, the efficacy of supercritical fluid technology as a preparative technique for the preparation of flurbiprofen-methyl-β-cyclodextrin inclusion complexes was evaluated. The complexes were prepared by supercritical carbon dioxide processing and were evaluated by solubility, differential scanning calorimetry, X-ray powder diffraction, scanning electron microscopy, practical yield, drug content estimation and in vitro dissolution studies. Computational molecular docking studies were conducted to study the possibility of molecular arrangement of inclusion complexes between flurbiprofen and methyl-β-cyclodextrin. The studies support the formation of stable molecular inclusion complexes between the drug and cyclodextrin in a 1:1 stoichiometry. In vitro dissolution studies showed that the dissolution properties of flurbiprofen were significantly enhanced by the binary mixtures prepared by supercritical carbon dioxide processing. The amount of flurbiprofen dissolved into solution alone was very low with 1.11±0.09% dissolving at the end of 60min, while the binary mixtures processed by supercritical carbon dioxide at 45°C and 200bar released 99.39±2.34% of the drug at the end of 30min. All the binary mixtures processed by supercritical carbon dioxide at 45°C exhibited a drug release of more than 80% within the first 10min irrespective of the pressure employed. The study demonstrated the single step, organic solvent-free supercritical carbon dioxide process as a promising approach for the preparation of inclusion complexes between flurbiprofen and methyl-β-cyclodextrin in solid-state. Copyright © 2016 Elsevier B.V. All rights reserved.

  1. Inclusion of Paracetamol into β-cyclodextrin nanocavities in solution and in the solid state

    NASA Astrophysics Data System (ADS)

    El-Kemary, Maged; Sobhy, Saffaa; El-Daly, Samy; Abdel-Shafi, Ayman

    2011-09-01

    We report on steady-state UV-visible absorption and emission characteristics of Paracetamol, drug used as antipyretic agent, in water and within cyclodextrins (CDs): β-CD, 2-hydroxypropyl- β-CD (HP- β-CD) and 2,6-dimethyl- β-CD (Me- β-CD). The results reveal that Paracetamol forms a 1:1 inclusion complex with CD. Upon encapsulation, the emission intensity enhances, indicating a confinement effect of the nanocages on the photophysical behavior of the drug. Due to its methyl groups, the Me- β-CD shows the largest effect for the drug. The observed binding constant showing the following trend: Me- β-CD > HP- β-CD > β-CD. The less complexing effectiveness of HP- β-CD is due to the steric effect of the hydroxypropyl-substituents, which can hamper the inclusion of the guest molecules. The solid state inclusion complex was prepared by co-precipitation method and its characterization was investigated by Fourier transform infrared spectroscopy, 1H NMR and X-ray diffractometry. These approaches indicated that Paracetamol was able to form an inclusion complex with CDs, and the inclusion compounds exhibited different spectroscopic features and properties from Paracetamol.

  2. Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent.

    PubMed

    Zengerle, Michael; Brandhuber, Florian; Schneider, Christian; Worek, Franz; Reiter, Georg; Kubik, Stefan

    2011-01-01

    The potential of appropriately substituted cyclodextrins to act as scavengers for neurotoxic organophosphonates under physiological conditions was evaluated. To this end, a series of derivatives containing substituents with an aldoxime or a ketoxime moiety along the narrow opening of the β-cyclodextrin cavity was synthesized, and the ability of these compounds to reduce the inhibitory effect of the neurotoxic organophosphonate cyclosarin on its key target, acetylcholinesterase, was assessed in vitro. All compounds exhibited a larger effect than native β-cyclodextrin, and characteristic differences were noted. These differences in activity were correlated with the structural and electronic parameters of the substituents. In addition, the relatively strong effect of the cyclodextrin derivatives on cyclosarin degradation and, in particular, the observed enantioselectivity are good indications that noncovalent interactions between the cyclodextrin ring and the substrate, presumably involving the inclusion of the cyclohexyl moiety of cyclosarin into the cyclodextrin cavity, contribute to the mode of action. Among the nine compounds investigated, one exhibited remarkable activity, completely preventing acetylcholinesterase inhibition by the (-)-enantiomer of cyclosarin within seconds under the conditions of the assay. Thus, these investigations demonstrate that decoration of cyclodextrins with appropriate substituents represents a promising approach for the development of scavengers able to detoxify highly toxic nerve agents.

  3. Highly efficient cyclosarin degradation mediated by a β-cyclodextrin derivative containing an oxime-derived substituent

    PubMed Central

    Zengerle, Michael; Brandhuber, Florian; Schneider, Christian; Worek, Franz; Reiter, Georg

    2011-01-01

    Summary The potential of appropriately substituted cyclodextrins to act as scavengers for neurotoxic organophosphonates under physiological conditions was evaluated. To this end, a series of derivatives containing substituents with an aldoxime or a ketoxime moiety along the narrow opening of the β-cyclodextrin cavity was synthesized, and the ability of these compounds to reduce the inhibitory effect of the neurotoxic organophosphonate cyclosarin on its key target, acetylcholinesterase, was assessed in vitro. All compounds exhibited a larger effect than native β-cyclodextrin, and characteristic differences were noted. These differences in activity were correlated with the structural and electronic parameters of the substituents. In addition, the relatively strong effect of the cyclodextrin derivatives on cyclosarin degradation and, in particular, the observed enantioselectivity are good indications that noncovalent interactions between the cyclodextrin ring and the substrate, presumably involving the inclusion of the cyclohexyl moiety of cyclosarin into the cyclodextrin cavity, contribute to the mode of action. Among the nine compounds investigated, one exhibited remarkable activity, completely preventing acetylcholinesterase inhibition by the (−)-enantiomer of cyclosarin within seconds under the conditions of the assay. Thus, these investigations demonstrate that decoration of cyclodextrins with appropriate substituents represents a promising approach for the development of scavengers able to detoxify highly toxic nerve agents. PMID:22238531

  4. Determination of binding constants of cyclodextrin inclusion complexes with amino acids and dipeptides by potentiometric titration.

    PubMed

    Kahle, Claudia; Holzgrabe, Ulrike

    2004-10-01

    Cyclodextrins are well known for their ability to separate enantiomers of drugs, natural products, and other chiral substances using HPLC, GC, or CE. The resolution of the enantiomers is due to the formation of diastereomeric complexes between the cyclodextrin and the pairs of enantiomers. The aim of this study was to determine the binding constants of the complexes between alpha- and beta-cyclodextrin and the enantiomers of a series of aliphatic and aromatic amino acids, and dipeptides, using a potentiometric titration method. The results of this method are compared to other methods, and correlated to findings in cyclodextrin-modified capillary electrophoresis and possible complex structures. Potentiometric titration was found to be an appropriate tool to determine the binding constants of cyclodextrin inclusion complexes.

  5. Inclusion compounds between α-, β- and γ-cyclodextrins: iron II lactate: a theoretical and experimental study using diffusion coefficients and molecular mechanics

    NASA Astrophysics Data System (ADS)

    Leite, Rosiley A.; Lino, Antonio C. S.; Takahata, Yuji

    2003-01-01

    The inclusion compounds between iron II lactate and three different cyclodextrins (CDs) were studied by means of experimental and theoretical data. The importance of iron II in the human metabolism effort the necessity of a minimum concentration to the human life. Malnutrition is one great problem in social politics of many countries on the world. The possibility to the development of novel medicines with the iron II species stable look for an increase on the efficiency for this kind of aid. Kinetics measurements confirm the possibility to stop the oxidation reaction. It was the first indication of efficient molecular encapsulation. Diffusion coefficient measurements were carried out by Taylor-Aris diffusion technique. The decrease of diffusion coefficients measured for iron II lactate when alone and forming the inclusion complexes was obtained for all hosts molecules used. Molecular Mechanics calculations were performed to elucidate the perfect arrange of iron II lactate inside CDs cavity. No great differences were obtained to the binding energy for the different hosts. Using the software HyperChem6.03v MM+, AMBER94 and OPLS Forced Fields for iron atom in two chemical environments (a) vacuum and (b) with addition of 250 water molecules (MM+). The solvent treatment was decisive to the order of stability. This order was β-CD>γ-CD>α-CD, the same order of solubility in water. The results contained in this work confirm the possibility to protect iron II lactate against oxidation.

  6. INTERACTIONS BETWEEN ORGANIC COMPOUNDS AND CYCLODEXTRIN-CLAY SYSTEMS

    EPA Science Inventory

    Computational and experimental techniques are combined in order to better understand interactions involving organic compounds and cyclodextrin (CD)-clay systems. CD-clay systems may have great potential in the containment of organic contaminants in the environment. This study w...

  7. Promising applications in drug delivery systems of a novel β-cyclodextrin derivative obtained by green synthesis.

    PubMed

    García, Agustina; Leonardi, Darío; Lamas, María C

    2016-01-15

    An efficient and green method has been developed for the synthesis of succinyl-β-cyclodextrin in aqueous media obtaining very good yield. Acidic groups have been introduced in the synthesized carrier molecule to improve the guest-host affinity. To evaluate the suitability of the novel excipient focused to develop oral dosage forms, albendazole, a BSC class II compound, was chosen as a model drug. The β-cyclodextrin derivative and the inclusion complex were thoroughly characterized in solution and solid state by phase solubility studies, FT-IR spectroscopy, SEM, XRD, ESI-MS, DSC, 1D (1)H NMR, 1D (13)C NMR, selective 1D TOCSY, 2D COSY, 2D HSQC, 2D HMBC and ROESY NMR spectroscopy. Phase solubility studies indicated that both of them β-cyclodextrin and succinyl-β-cyclodextrin formed 1:1 inclusion complexes with albendazole, and the stability constants were 68M(-1) (β-cyclodextrin), 437M(-1) (succinyl-β-cyclodextrin), respectively. Water solubility and dissolution rate of albendazole were significantly improved in complex forms. Thus, the succinyl-β-cyclodextrin derivative could be a promising excipient to design oral dosage forms. Copyright © 2015 Elsevier Ltd. All rights reserved.

  8. Characterization of mitotane (o,p'-DDD)--cyclodextrin inclusion complexes: phase-solubility method and NMR.

    PubMed

    Alfonsi, R; Attivi, D; Astier, A; Socha, M; Morice, S; Gibaud, S

    2013-05-01

    Mitotane (o,p'-dichlorodimethyl dichloroethane [o,p'-DDD]) is used for the treatment of adrenocortical cancer and occasionally Cushing's syndrome. This drug is very poorly soluble in water, and following oral administration, approximately 60% of the dose is recovered in the feces unaltered. The preparation of a soluble formulation (i.e. by complexation with cyclodextrins) with improved bioavailability is the aim of this work. The inclusion of mitotane in methyl-ß-cyclodextrins was studied using both phase-solubility methods and NMR experiments. To elucidate the inclusion mechanism, o,p'-DDD was compared to its regioisomer (i.e. p,p'-DDD). It was demonstrated that two dimethyl-ß-cyclodextrins (DMßCD) can complex with the aromatic rings. From the phase-solubility diagrams, we observe that both cases are very different: K(1:1) is between 37 000 and 85 000 mol.l(-1), whereas K(1:2) is between 5.3 and 32 mol.l(-1). The NMR experiments confirmed the inclusion but it also gave an insight into the kinetics of the dissociation: the ortho-chloro moiety is in slow exchange on the NMR time scale, whereas the para-chloro moiety is in fast exchange rate. Copyright © 2013 Elsevier Masson SAS. All rights reserved.

  9. Preparation, characterization, and in vitro anti-inflammatory evaluation of novel water soluble kamebakaurin/hydroxypropyl-β-cyclodextrin inclusion complex

    NASA Astrophysics Data System (ADS)

    Raza, Aun; Sun, Huifang; Bano, Shumaila; Zhao, Yingying; Xu, Xiuquan; Tang, Jian

    2017-02-01

    To enhance the aqueous solubility of kamebakaurin (KA), it was complexed with hydroxypropyl-β-cyclodextrin (HP-β-CD). In this study, the interaction KA with HP-β-CD and their inclusion complex behavior were determined by different characterization techniques such as UV-vis, 1H NMR, FT-IR, PXRD and SEM. All the characterization information proved the development of inclusion complex KA/HP-β-CD, and this inclusion complex demonstrated discriminable spectroscopic characteristics and properties from free compound KA. The results demonstrated that the water solubility of KA was remarkably increased in the presence of HP-β-CD. Furthermore, in vitro anti-inflammatory study showed that inclusion complex KA/HP-β-CD maintained the anti-inflammatory effect of KA. These results demonstrate that HP-β-CD will be promisingly employed in the application of water-insoluble anti-inflammatory phytochemicals such as KA.

  10. Anti-aggregatory effect of cyclodextrins in the refolding process of recombinant growth hormones from Escherichia coli inclusion bodies.

    PubMed

    Bajorunaite, Egle; Cirkovas, Andrejus; Radzevicius, Kostas; Larsen, Kim Lambertsen; Sereikaite, Jolanta; Bumelis, Vladas-Algirdas

    2009-06-01

    Cyclodextrins with different ring size and ring substituents were tested for recombinant mink and porcine growth hormones aggregation suppression in the refolding process from Escherichia coli inclusion bodies. Methyl-beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin show a positive effect on the aggregation suppression of both proteins. The influence of different methyl-beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin concentrations on the renaturation yield of both growth hormones was investigated. Moreover, methyl-beta-cyclodextrin and 2-hydroxypropyl-beta-cyclodextrin suppress not only folding-related, but also temperature-related aggregates formation of both proteins. Circular dichroism experiments (monitoring of protein solution turbidity by registering high tension voltage) showed that the onset temperature of aggregation of both growth hormones increased with increasing 2-hydroxypropyl-beta-cyclodextrin concentration. In conclusion, cyclodextrins have perspectives in biotechnology of veterinary growth hormones not only for protein production, but also for its storage.

  11. [Effect of β-cyclodextrin inclusion complex on transport of major components of Xiangfu Siwu decoction essential oil in Caco-2 cell monolayer model].

    PubMed

    Xi, Jun-zuan; Qian, Da-wei; Duan, Jin-ao; Liu, Pei; Zhu, Yue; Zhu, Zhen-hua; Zhang, Li

    2015-08-01

    Although the essential oil of Xiangfu Siwu decoction (XFSWD) has strong pharmacological activity, its special physical and chemical properties restrict the clinical application and curative effect. In this paper, Xiangfu Siwu decoction essential oil (XFS-WO) was prepared by forming inclusion complex with β-cyclodextrin (β-CD). The present study is to investigate the effect of β-CD inclusion complex on the transport of major components of XFSWO using Caco-2 cell monolayer model, thus to research the effect of this formation on the absorption of drugs with low solubility and high permeability, which belong to class 2 in biopharmaceutics classification system. A sensitive and rapid UPLC-MS/MS method was developed for simultaneous quantification of senkyunolide A, 3-n-butylphthalide, Z-ligustilide, dehydrocostus lactone and α-cyperone, which are active compounds in XFSWO. The transport parameters were analyzed and compared in free oil and its β-CD inclusion complex. The result revealed that the formation of XFSWO/β-CD inclusion complex has significantly increased the transportation and absorption of major active ingredients than free oil. Accordingly, it can be speculated that cyclodextrin inclusion complex can improve bioavailability of poorly water-soluble drugs. Above all these mentioned researches, it provided foundation and basis for physiological disposition and pharmaceutical study of XFSWD.

  12. Development of carvedilol-cyclodextrin inclusion complexes using fluid-bed granulation: a novel solid-state complexation alternative with technological advantages.

    PubMed

    Alonso, Ellen C P; Riccomini, Karina; Silva, Luis Antônio D; Galter, Daniela; Lima, Eliana M; Durig, Thomas; Taveira, Stephania F; Martins, Felipe Terra; Cunha-Filho, Marcílio S S; Marreto, Ricardo N

    2016-10-01

    This study sought to evaluate the achievement of carvedilol (CARV) inclusion complexes with modified cyclodextrins (HPβCD and HPγCD) using fluid-bed granulation (FB). The solid complexes were produced using FB and spray drying (SD) and were characterised by differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction, SEM, flowability and particle size analyses and in vitro dissolution. The DSC, FTIR and powder X-ray diffraction findings suggested successful CARV inclusion in the modified β- and γ-cyclodextrins, which was more evident in acidic media. The CARV dissolution rate was ~7-fold higher for complexes with both cyclodextrins prepared using SD than for raw CARV. Complexes prepared with HPβCD using FB also resulted in a significant improvement in dissolution rate (~5-fold) and presented superior flowability and larger particle size. The findings suggested that FB is the best alternative for large-scale production of solid dosage forms containing CARV. Additionally, the results suggest that HPγCD could be considered as another option for CARV complexation because of its excellent performance in inclusion complex formation in the solid state. © 2016 Royal Pharmaceutical Society.

  13. A circular dichroism and structural study of the inclusion complex artemisinin-β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Marconi, Giancarlo; Monti, Sandra; Manoli, Francesco; Degli Esposti, Alessandra; Mayer, Bernd

    2004-01-01

    The inclusion complex between the powerful antimalarial agent Artemisinin and β-cyclodextrin has been studied by means of Circular Dichroism and elucidated by Density Functional Theory calculations on the isolated molecule combined to a statistical Monte Carlo search of the most stable geometry of the complex. The results evidence a host-guest structure in full agreement with the almost unaffected functionality of the drug, which is found to experience a significant hydrophilic environment when complexed.

  14. Modified β-Cyclodextrin Inclusion Complex to Improve the Physicochemical Properties of Albendazole. Complete In Vitro Evaluation and Characterization

    PubMed Central

    García, Agustina; Leonardi, Darío; Salazar, Mario Oscar; Lamas, María Celina

    2014-01-01

    The potential use of natural cyclodextrins and their synthetic derivatives have been studied extensively in pharmaceutical research and development to modify certain properties of hydrophobic drugs. The ability of these host molecules of including guest molecules within their cavities improves notably the physicochemical properties of poorly soluble drugs, such as albendazole, the first chosen drug to treat gastrointestinal helminthic infections. Thus, the aim of this work was to synthesize a beta cyclodextrin citrate derivative, to analyze its ability to form complexes with albendazole and to evaluate its solubility and dissolution rate. The synthesis progress of the cyclodextrin derivative was followed by electrospray mass spectrometry and the acid-base titration of the product. The derivative exhibited an important drug affinity. Nuclear magnetic resonance experiments demonstrated that the tail and the aromatic ring of the drug were inside the cavity of the cyclodextrin derivative. The inclusion complex was prepared by spray drying and full characterized. The drug dissolution rate displayed exceptional results, achieving 100% drug release after 20 minutes. The studies indicated that the inclusion complex with the cyclodextrin derivative improved remarkably the physicochemical properties of albendazole, being a suitable excipient to design oral dosage forms. PMID:24551084

  15. Preparation, characterization and molecular modeling studies of the inclusion complex of Caffeine with Beta-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Prabu, Samikannu; Swaminathan, Meenakshisundaram; Sivakumar, Krishnamoorthy; Rajamohan, Rajaram

    2015-11-01

    The formation through supramolecular interaction of a host-guest inclusion complex of caffeine (CA) with nano-hydrophobic cavity beta-cyclodextrin (β-CD) is achieved by a physical mixture, a kneading method and a co-precipitation method. The formation of the inclusion complex of CA with β-CD in solution state is confirmed by UV-visible spectrophotometer, fluorescence spectrophotometer and time-resolved fluorescence spectrophotometer. The stoichiometry of the inclusion complex is 1:1; the imidazole ring and pyrimidine ring of caffeine is deeply entrapped in the beta-cyclodextrin as confirmed by spectral shifts. The Benesi-Hildebrand plot is used to calculate the binding constant of the inclusion complex of CA with β-CD at room temperature. The Gibbs free energy change of the inclusion complex process is calculated and the process is found to be spontaneous. The thermal stability of the inclusion complex of CA with β-CD is analyzed using differential scanning calorimetry. The crystal structure modification of a solid inclusion complex is confirmed by scanning electron microscopy image analysis. The formation of the inclusion complex of CA with β-CD in the solid phase is also confirmed by FT-IR and XRD. The formation of the inclusion complex between CA and β-CD, as confirmed by molecular docking studies, is in good relationship with the results obtained through different experimental methods.

  16. Complexation of morin with three kinds of cyclodextrin. A thermodynamic and reactivity study

    NASA Astrophysics Data System (ADS)

    Jullian, Carolina; Orosteguis, Teresita; Pérez-Cruz, Fernanda; Sánchez, Paulina; Mendizabal, Fernando; Olea-Azar, Claudio

    2008-11-01

    Properties of inclusion complexes between morin (M) and β-cyclodextrin (βCD), 2-hydroxypropyl-β-cyclodextrin (HPβCD) and Heptakis (2,6- O-di methyl) β-cyclodextrin (DMβCD) such as aqueous solubility and the association constants of this complex have been determined. The water solubility of morin was increased by inclusion with cyclodextrins. The phase-solubility diagrams drawn from UV spectral measurements are of the A L-type. Also ORAC FL studies were done. An increase in the antioxidant reactivity is observed when morin form inclusion complex with the three cyclodextrin studied. Finally, thermodynamics studies of cyclodextrin complexes indicated that for DMβCD the inclusion is primarily enthalpy-driven process meanwhile βCD and HPβCD are entropy-driven processes. This is corroborated by the different inclusion geometries obtained by 2D-NMR.

  17. Theoretical and Experimental Study of Inclusion Complexes of β-Cyclodextrins with Chalcone and 2',4'-Dihydroxychalcone.

    PubMed

    Sancho, Matias I; Andujar, Sebastian; Porasso, Rodolfo D; Enriz, Ricardo D

    2016-03-31

    The inclusion complexes formed by chalcone and 2',4'-dihydroxychalcone with β-cyclodextrin have been studied combining experimental (phase solubility diagrams, Fourier transform infrared spectroscopy) and molecular modeling (molecular dynamics, quantum mechanics/molecular mechanics calculations) techniques. The formation constants of the complexes were determined at different temperatures, and the thermodynamic parameters of the process were obtained. The inclusion of chalcone in β-cyclodextrin is an exothermic process, while the inclusion of 2',4'-dihydroxychalcone is endothermic. Free energy profiles, derived from umbrella sampling using molecular dynamics simulations, were constructed to analyze the binding affinity and the complexation reaction at a molecular level. Hybrid QM/MM calculations were also employed to obtain a better description of the energetic and structural aspects of the complexes. The intermolecular interactions that stabilize both inclusion complexes were characterized by means of quantum atoms in molecules theory and reduce density gradient method. The calculated interactions were experimentally observed using FTIR.

  18. (13)C and (15)N solid-state NMR studies on albendazole and cyclodextrin albendazole complexes.

    PubMed

    Ferreira, M João G; García, A; Leonardi, D; Salomon, Claudio J; Lamas, M Celina; Nunes, Teresa G

    2015-06-05

    (13)C and (15)N solid-state nuclear magnetic resonance (NMR) spectra were recorded from albendazole (ABZ) and from ABZ:β-cyclodextrin, ABZ:methyl-β-cyclodextrin, ABZ:hydroxypropyl-β-cyclodextrin and ABZ:citrate-β-cyclodextrin, which were prepared by the spray-drying technique. ABZ signals were typical of a crystalline solid for the pure drug and of an amorphous compound obtained from ABZ:cyclodextrin samples. Relevant spectral differences were correlated with chemical interaction between ABZ and cyclodextrins. The number and type of complexes revealed a strong dependence on the cyclodextrin group substituent. Solid-state NMR data were consistent with the presence of stable inclusion complexes. Copyright © 2015 Elsevier Ltd. All rights reserved.

  19. [Study on two preparation methods for beta-CD inclusion compound of four traditional Chinese medicine volatile oils].

    PubMed

    Li, Hailiang; Cui, Xiaoli; Tong, Yan; Gong, Muxin

    2012-04-01

    To compare inclusion effects and process conditions of two preparation methods-colloid mill and saturated solution-for beta-CD inclusion compound of four traditional Chinese medicine volatile oils and study the relationship between each process condition and volatile oil physical properties and the regularity of selective inclusion of volatile oil components. Volatile oils from Nardostachyos Radix et Rhizoma, Amomi Fructus, Zingiberis Rhizoma and Angelicaesinensis Radix were prepared using two methods in the orthogonal test. These inclusion compounds by optimized processes were assessed and compared by such methods as TLC, IR and scanning electron microscope. Inclusion oils were extracted by steam distillation, and the components found before and after inclusion were analyzed by GC-MS. Analysis showed that new inclusion compounds, but inclusion compounds prepared by the two processes had differences to some extent. The colloid mill method showed a better inclusion effect than the saturated solution method, indicating that their process conditions had relations with volatile oil physical properties. There were differences in the inclusion selectivity of components between each other. The colloid mill method for inclusion preparation is more suitable for industrial requirements. To prepare volatile oil inclusion compounds with heavy gravity and high refractive index, the colloid mill method needs longer time and more water, while the saturated solution method requires higher temperature and more beta-cyclodextrin. The inclusion complex prepared with the colloid mill method contains extended molecular weight chemical composition, but the kinds of components are reduced.

  20. Piroxicam-β-Cyclodextrin: A GI Safer Piroxicam

    PubMed Central

    Scarpignato, C

    2013-01-01

    to a more rapid onset of action after oral administration and improved GI tolerability because of minimization of the drug gastric effects. One such drug, piroxicam-β-cyclodextrin (PBC), has been used in Europe for 25 years. Preclinical and clinical pharmacology of PBC do show that the β-cyclodextrin inclusion complex of piroxicam is better tolerated from the upper GI tract than free piroxicam, while retaining all the analgesic and anti-inflammatory properties of the parent compound. In addition, the drug is endowed with a quick absorption rate, which translates into a faster onset of analgesic activity, an effect confirmed in several clinical studies. An analysis of the available trials show that PBC has a GI safety profile, which is better than that displayed by uncomplexed piroxicam. Being an inclusion complex of piroxicam, whose CV safety has been pointed out by several observational studies, PBC should be viewed as a CV safe anti-inflmmatory compound and a GI safer alternative to piroxicam. As a consequence, it should be considered as a useful addition to our therapeutic armamentarium. PMID:23394552

  1. Preparation and Characterization of Nanoparticle β-Cyclodextrin:Geraniol Inclusion Complexes.

    PubMed

    Hadian, Zahra; Maleki, Majedeh; Abdi, Khosro; Atyabi, Fatemeh; Mohammadi, Abdoreza; Khaksar, Ramin

    2018-01-01

    The aim of the present study was to formulate β-cyclodextrin (β-CD) nanoparticles loaded with geraniol (GR) essential oil (EO) with appropriate physicochemical properties. Complexation of GR with β-CD was optimized by evaluation of four formulations, using the co-precipitation method, and the encapsulation efficiency (EE), loading, size, particle size distribution (PDI) and zeta potential were investigated. Further characterization was performed with nuclear magnetic resonance spectroscopy ( 1 H NMR), differential scanning calorimetry (DSC), scanning electron microscopy (SEM) and infra-red (IR) spectroscopy analysis. Results showed that the physicochemical properties of the nanoparticles were affected by GR content in formulations that yielded nanoscale-size particles ranging from 111 to 258 nm. The highest encapsulation efficiency (79.4 ± 5.4%) was obtained when the molar ratio of EO to β-CD was 0.44: 0.13 with negative zeta potential (-21.1 ± 0.5 mV). The 1 H-NMR spectrum confirmed the formation structure of the EO and β-CD nanoparticle complex. Complexation with geraniol resulted in changes of IR profile, NMR chemical shifts, DSC properties, and SEM of β-cyclodextrin. Inclusion complex of essential oil with β-cyclodextrin was considered as promising bioactive materials for designing functional food.

  2. Preparation and Characterization of Nanoparticle β-Cyclodextrin:Geraniol Inclusion Complexes

    PubMed Central

    Hadian, Zahra; Maleki, Majedeh; Abdi, Khosro; Atyabi, Fatemeh; Mohammadi, Abdoreza; Khaksar, Ramin

    2018-01-01

    The aim of the present study was to formulate β-cyclodextrin (β-CD) nanoparticles loaded with geraniol (GR) essential oil (EO) with appropriate physicochemical properties. Complexation of GR with β-CD was optimized by evaluation of four formulations, using the co-precipitation method, and the encapsulation efficiency (EE), loading, size, particle size distribution (PDI) and zeta potential were investigated. Further characterization was performed with nuclear magnetic resonance spectroscopy (1H NMR), differential scanning calorimetry (DSC), scanning electron microscopy (SEM) and infra-red (IR) spectroscopy analysis. Results showed that the physicochemical properties of the nanoparticles were affected by GR content in formulations that yielded nanoscale-size particles ranging from 111 to 258 nm. The highest encapsulation efficiency (79.4 ± 5.4%) was obtained when the molar ratio of EO to β-CD was 0.44: 0.13 with negative zeta potential (-21.1 ± 0.5 mV). The 1H-NMR spectrum confirmed the formation structure of the EO and β-CD nanoparticle complex. Complexation with geraniol resulted in changes of IR profile, NMR chemical shifts, DSC properties, and SEM of β-cyclodextrin. Inclusion complex of essential oil with β-cyclodextrin was considered as promising bioactive materials for designing functional food.

  3. Self-association and cyclodextrin solubilization of drugs.

    PubMed

    Loftsson, Thorsteinn; Magnúsdóttir, Auethur; Másson, Már; Sigurjónsdóttir, Jóhanna F

    2002-11-01

    Phase-solubility diagrams are frequently used to calculate stoichiometry of drug/cyclodextrin complexes. Linear diagrams (A(L)-type systems) are thought to indicate that the complexes are first order with respect to cyclodextrin and first or higher order with respect to the drug. Positive deviation from linearity (A(P)-type systems) are thought to indicate formation of complexes that are first order with respect to the drug but second or higher order with respect to cyclodextrin. The phase solubility of several different compounds, i.e., cholesterol, ibuprofen, diflunisal, alprazolam, 17beta-estradiol and diethylstilbestrol, and various charged and uncharged cyclodextrins was investigated. Phase-solubility diagrams of cholesterol in aqueous cyclodextrin solutions were all of A(P) type. However, the phase-solubility diagrams obtained with charged cyclodextrins could not be fitted to complexes of second or higher order with respect to cyclodextrin. The phase-solubility diagrams of ibuprofen and diflunisal were of A(L) type with slope greater than unity indicating formation of 2:1 drug/cyclodextrin complexes. However, Job's plots and space filling docking studies indicated that 1:1 complexes were formed. These and other observations show that stoichiometry of drug/cyclodextrin complexes cannot be derived from simple phase-solubility studies. Furthermore, the results indicate that drug/cyclodextrin complexes can self-associate to form water-soluble aggregates, which then can further solubilize the drug through non-inclusion complexation. Copyright 2002 Wiley-Liss, Inc. and the American Pharmaceutical Association J Pharm Sci 91:2307-2316, 2002

  4. Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

    PubMed Central

    Becker, Lisa F; Schwarz, Dennis H

    2014-01-01

    Summary Methyl and ethyl thioether groups were introduced at all primary positions of α-, β-, and γ-cyclodextrin by nucleophilic displacement reactions starting from the corresponding per-(6-deoxy-6-bromo)cyclodextrins. Further modification of all 2-OH positions by etherification with iodo terminated triethylene glycol monomethyl ether (and tetraethylene glycol monomethyl ether, respectively) furnished water-soluble hosts. Especially the β-cyclodextrin derivatives exhibit very high binding potentials towards the anaesthetic drugs sevoflurane and halothane. Since the resulting inclusion compounds are highly soluble in water at temperatures ≤37 °C they are good candidates for new aqueous dosage forms which would avoid inhalation anaesthesia. PMID:25550759

  5. Synthesis and Utilization of Trialkylammonium-Substituted Cyclodextrins as Water-Soluble Chiral NMR Solvating Agents for Anionic Compounds.

    PubMed

    Dowey, Alison E; Puentes, Cira Mollings; Carey-Hatch, Mira; Sandridge, Keyana L; Krishna, Nikhil B; Wenzel, Thomas J

    2016-04-01

    Cationic trialkylammonium-substituted α-, β-, and γ-cyclodextrins containing trimethyl-, triethyl-, and tri-n-propylammonium substituent groups were synthesized and analyzed for utility as water-soluble chiral nuclear magnetic resonance (NMR) solvating agents. Racemic and enantiomerically pure (3-chloro-2-hydroxypropyl)trimethyl-, triethyl-, and tri-n-propyl ammonium chloride were synthesized from the corresponding trialkyl amine hydrochloride and either racemic or enantiomerically pure epichlorohydrin. The ammonium salts were then reacted with α-, β-, and γ-cyclodextrins at basic pH to provide the corresponding randomly substituted cationic cyclodextrins. The (1) H NMR spectra of a range of anionic, aromatic compounds was recorded with the cationic cyclodextrins. Cyclodextrins with a single stereochemistry at the hydroxy group on the (2-hydroxypropyl)trialkylammonium chloride substituent were often but not always more effective than the corresponding cyclodextrin in which the C-2 position was racemic. In several cases, the larger triethyl or tri-n-propyl derivatives were more effective than the corresponding trimethyl derivative at causing enantiomeric differentiation. None of the cyclodextrin derivatives were consistently the most effective for all of the anionic compounds studied. © 2016 Wiley Periodicals, Inc.

  6. Preparation, characterization, and thermal stability of β-cyclodextrin/soybean lecithin inclusion complex.

    PubMed

    Wang, Xinge; Luo, Zhigang; Xiao, Zhigang

    2014-01-30

    β-Cyclodextrin (β-CD), which is widely used to increase the stability, solubility, and bioavailability of guests, can form host-guest inclusion complexes with a wide variety of organic molecules. In this study the β-CD/soybean lecithin inclusion complex was prepared. The effect of reaction parameters such as reaction temperature, reaction time and the molar ratio of β-CD/soybean lecithin on inclusion ratio were studied. The inclusion ratio of the product prepared under the optimal conditions of β-CD/soybean lecithin molar ratio 2:1, reaction temperature 60°C reaction time 2h was 40.2%. The results of UV-vis, DSC, XRD and FT-IR spectrum indicated the formation of inclusion complex. The thermal stability experiment indicated that the thermal stability of soybean lecithin in inclusion complex was significantly improved compared with free soybean lecithin. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. Applications of cyclodextrins in medical textiles - review.

    PubMed

    Radu, Cezar-Doru; Parteni, Oana; Ochiuz, Lacramioara

    2016-02-28

    This paper presents data on the general properties and complexing ability of cyclodextrins and assessment methods (phase solubility, DSC tests and X-ray diffraction, FTIR spectra, analytical method). It focuses on the formation of drug deposits on the surface of a textile underlayer, using a cyclodextrin compound favoring the inclusion of a drug/active principle and its release onto the dermis of patients suffering from skin disorders, or for protection against insects. Moreover, it presents the kinetics, duration, diffusion flow and release media of the cyclodextrin drug for in vitro studies, as well as the release modeling of the active principle. The information focuses on therapies: antibacterial, anti-allergic, antifungal, chronic venous insufficiency, psoriasis and protection against insects. The pharmacodynamic agents/active ingredients used on cotton, woolen and synthetic textile fabrics are presented. Copyright © 2016 Elsevier B.V. All rights reserved.

  8. DSC, X-ray and FTIR studies of a gemfibrozil/dimethyl-β-cyclodextrin inclusion complex produced by co-grinding.

    PubMed

    Aigner, Z; Berkesi, O; Farkas, G; Szabó-Révész, P

    2012-01-05

    The steps of formation of an inclusion complex produced by the co-grinding of gemfibrozil and dimethyl-β-cyclodextrin were investigated by differential scanning calorimetry (DSC), X-ray powder diffractometry (XRPD) and Fourier transform infrared (FTIR) spectroscopy with curve-fitting analysis. The endothermic peak at 59.25°C reflecting the melting of gemfibrozil progressively disappeared from the DSC curves of the products on increase of the duration of co-grinding. The crystallinity of the samples too gradually decreased, and after 35min of co-grinding the product was totally amorphous. Up to this co-grinding time, XRPD and FTIR investigations indicated a linear correlation between the cyclodextrin complexation and the co-grinding time. After co-grinding for 30min, the ratio of complex formation did not increase. These studies demonstrated that co-grinding is a suitable method for the complexation of gemfibrozil with dimethyl-β-cyclodextrin. XRPD analysis revealed the amorphous state of the gemfibrozil-dimethyl-β-cyclodextrin product. FTIR spectroscopy with curve-fitting analysis may be useful as a semiquantitative analytical method for discriminating the molecular and amorphous states of gemfibrozil. Copyright © 2011 Elsevier B.V. All rights reserved.

  9. Preparation, characterization and binding behaviors of host-guest inclusion complexes of metoclopramide hydrochloride with α- and β-cyclodextrin molecules

    NASA Astrophysics Data System (ADS)

    Barman, Siti; Barman, Biraj Kumar; Roy, Mahendra Nath

    2018-03-01

    The supramolecular interaction of metoclopramide hydrochloride (MP) with α-cyclodextrin (α-CD) and β-cyclodextrin (β-CD) has been inspected by ultraviolet-visible (UV-vis) light, infra-red (IR) light, fluorescence and 1H NMR spectroscopy. The formation of an inclusion complex greatly affects the physical-chemical properties of the guest molecules, such as solubility, chemical reactivity and the spectroscopic and electrochemical properties. Thus the changes in the spectral properties and physico-chemical properties confirm the inclusion complex formation. Surface tension, conductivity studies and Job's plot indicate a 1: 1 stoichiometry of the MP:CD host-guest inclusion complexes. The binding/association constants have been evaluated by both UV-Vis and fluorescence spectroscopic study indicating a higher degree of encapsulation for β-cyclodextrin (β-CD). Furthermore, the negative value of thermodynamic parameter (ΔG°) of the host-guest system suggests that the inclusion process proceeded spontaneously at 298.15 K. Based on the NMR data, the plausible mode of interaction of MP:α-CD and MP:β-CD complexes were proposed, which suggested that lipophilic aromatic ring of the MP entered into the cavity of CDs from the wider side, with the amide (sbnd CONH) and methoxy (-OMe) residues inside the CD cavity.

  10. Phase Structure and Properties of a Biodegradable Block Copolymer Coalesced from It's Crystalline Inclusion Compound Formed with alpha-Cyclodextrin

    NASA Astrophysics Data System (ADS)

    Shuai, Xintao; Wei, Min; Probeni, Francis; Bullions, Todd A.; Shin, I. Daniel; Tonelli, Alan E.

    2002-03-01

    A well-defined biodegradable block copolymer of poly(epsilon caprolactone) (PCL) and poly(L-lactic acid) (PLLA) was synthesized and characterized and then included as a guest in an inclusion compound (IC) formed with the host alpha-cyclodextrin (CD). The PCL-b-PLLA block copolymer was subsequently coalesced from it's CD-IC crystals by either treatment with hot water (50 C) or an aqueous amylase solution at 25 C. The coalesced PCL-b-PLLA was examined by FTIR, DSC, TGA, and WAXD and was found to be much more homogeneosly organized, with much less segregation and crystallinity of the PCL and PLLA microphases. The morpholgy, crystallization kinetics, thermal behavior, and biodegradability of the coalesced PCL-b-PLLA block copolymer was studied by comparison to similar observations made on as-synthesized PCL-b-PLLA, PCL and PLLA homopolymers, and their solution-cast blend. The PCL and PLLA blocks are found to be more intimately mixed, with less phase segregation, in the coalesced diblock copolymer, and this leads to homogeneous bulk crystallization, which is not observed for the as-synthesized diblock copolymer. The coalesced PCL-b-PLLA was also found to be more quickly biodegraded (lipase from Rhizopus arrhizus)than the as-synthesized PCL-b-PLLA or the physical blend of PCL and PLLA homopolymers. Overall, the coalescence of the inherently phase segregated diblock copolymer PCL-b-PLLA results in a small amount of compact, chain-extended PCL and PLLA crystals embedded in an amorphous phase, largely consisting of well-mixed PCL and PLLA blocks. Thus, we have demonstrated that it is possible to control the morpholgy of a biodegradable diblock copolymer, thereby significantly modifying it's properties, by coalescence from it's CD-IC crystals.

  11. Complexation of phytochemicals with cyclodextrin derivatives - An insight.

    PubMed

    Suvarna, Vasanti; Gujar, Parul; Murahari, Manikanta

    2017-04-01

    Natural compounds have been attracting huge attention because of their broad therapeutic properties with specificity in their action in human health care as functional foods, pharmaceuticals and nutraceuticals. However poor bioavailability and reduced bioactivity attributed to poor solubility and instability is the major drawback hindering the incorporation of these therapeutically potential molecules in novel drug delivery systems. Based on the findings of reported research investigations; complexation of poorly water soluble phytochemicals with cyclodextrins has emerged to be a promising approach to improve their aqueous solubility, stability, rate of dissolution and bioavailability. The present article summarizes the encapsulation of natural compounds ranging from various flavonoids, phenolic derivatives, coumestans to triterpenes, with cyclodextrin and their derivatives. Also the article highlights the method of complexation, complexation ability, drug solubility, stability, bioavailability and safety aspects of reported natural compounds. Additionally we present the glimpses of patents published in recent 10-15 years to highlight the significance of inclusion of phytochemicals in cyclodextrins. In patents narrated, improvement in stability and solubility of curcumin by complexation with alkyl ether derivative of gamma-cyclodextrin is claimed. Another patent mentioned, complexation of artemisinins with β-cyclodextrin, improved the stability and integrity of peroxide part of artemisinins for long period. On the other hand the complex of dihydromyricetin with γ-CD has shown improved solubility, stability and bioavailability. Thus it can be concluded that phytochemicals have multiple biological activities with broader safety index and improvement of their solubility will be truly beneficial to aid their effective delivery in healthcare. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  12. Prediction of selectivity for enantiomeric separations of uncharged compounds by capillary electrophoresis involving dual cyclodextrin systems.

    PubMed

    Abushoffa, Adel M; Fillet, Marianne; Hubert, Phillipe; Crommen, Jacques

    2002-03-01

    The single-isomer polyanionic cyclodextrin (CD) derivative heptakis-6-sulfato-beta-cyclodextrin (HSbetaCD) has been tested as chiral additive for the enantioseparation of non-steroidal anti-inflammatory drugs, such as fenoprofen, flurbiprofen, ibuprofen and ketoprofen, in capillary electrophoresis, using a pH 2.5 phosphoric acid-triethanolamine buffer in the reversed polarity mode. In most cases, the enantiomers of these acidic compounds, present in uncharged form at that pH, were only poorly resolved with HSbetaCD alone. However, the use of HSbetaCD in combination with the neutral CD derivative, heptakis-(2,3,6-tri-O-methyl)-beta-cyclodextrin (TMbetaCD), which has a particularly high enantioselectivity towards these compounds, has led to complete enantioresolution in reasonably low migration times in most cases. Affinity constants for the enantiomers with the two cyclodextrins were determined, using linear regression in a two-step approach. Affinity constants with the charged HSbetaCD were first calculated in single systems while those with the neutral TMbetaCD were determined in dual systems. Selectivity for the enantiomeric separation of these compounds in dual CD systems could be predicted using recently developed mathematical models.

  13. Separation of drug stereoisomers by the formation of. beta. -cyclodextrin inclusion complexes

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Armstrong, D.W.; Ward, T.J.; Armstrong, R.D.

    For many drugs, only racemic mixtures are available for clinical use. Because different stereoisomers of drugs often cause different physiological responses, the use of pure isomers could elicit more exact therapeutic effects. Differential complexation of a variety of drug stereoisomers by immobilized ..beta..-cyclodextrin was investigated. Chiral recognition and racemic resolution were observed with a number of compounds from such clinically useful classes as ..beta..-blockers, calcium-channel blockers, sedative hypnotics, antihistamines, anticonvulsants, diuretics, and synthetic opiates. Separation of the diastereomers of the cardioactive and antimalarial cinchona alkaloids and of two antiestrogens was demonstrated as well. Three dimensional projections of ..beta..-cyclodextrin complexes ofmore » propanol, which is resolved by this technique, and warfarin, which is not, are compared. These studies have improved the understanding and application of the chiral interactions of ..beta..-cyclodextrin, and they have demonstrated a means to measure optical purity and to isolate or produce pure enantiomers of drugs. In addition, this highly specific technique could also be used in the pharmacological evaluation of enantiometric drugs. 27 references, 3 figures, 2 tables.« less

  14. Electrospinning of cyclodextrin/linalool-inclusion complex nanofibers: Fast-dissolving nanofibrous web with prolonged release and antibacterial activity.

    PubMed

    Aytac, Zeynep; Yildiz, Zehra Irem; Kayaci-Senirmak, Fatma; Tekinay, Turgay; Uyar, Tamer

    2017-09-15

    The volatility and limited water solubility of linalool is a critical issue to be solved. Here, we demonstrated the electrospinning of polymer-free nanofibrous webs of cyclodextrin/linalool-inclusion complex (CD/linalool-IC-NFs). Three types of modified cyclodextrin (HPβCD, MβCD, and HPγCD) were used to electrospin CD/linalool-IC-NFs. Free-standing CD/linalool-IC-NFs facilitate maximum loading of linalool up to 12% (w/w). A significant amount of linalool (45-89%) was preserved in CD/linalool-IC-NFs, due to enhancement in the thermal stability of linalool by cyclodextrin inclusion complexation. Remarkably, CD/linalool-IC-NFs have shown fast-dissolving characteristics in which these nanofibrous webs dissolved in water within two seconds. Furthermore, linalool release from CD/linalool-IC-NFs inhibited growth of model Gram-negative (E. coli) and Gram-positive (S. aureus) bacteria to a great extent. Briefly, characteristics of liquid linalool have been preserved in a solid nanofiber form and designed CD/linalool-IC-NFs confer high loading capacity, enhanced shelf life and strong antibacterial activity of linalool. Copyright © 2017 Elsevier Ltd. All rights reserved.

  15. Post monitoring of a cyclodextrin remeditated chlorinated solvent contaminated aquifer

    NASA Astrophysics Data System (ADS)

    Blanford, W. J.

    2006-12-01

    Hydroxypropyl-â-cyclodextrin (HPâCD) has been tested successfully in the laboratory and in the field for enhanced flushing of low-polarity contaminants from aquifers. The cyclodextrin molecule forms a toroidal structure, which has a hydrophobic cavity. Within this cavity, organic compounds of appropriate shape and size can form inclusion complexes, which is the basis for the use of cyclodextrin in groundwater remediation. The hydrophilic exterior of the molecule makes cyclodextrin highly water-soluble. The solubility of cyclodextrins can be further enhanced by adding functional groups, such as hydroxypropyl groups, to the cyclodextrin core. The aqueous solubility of HPâCD exceeds 950 g/L. These high solubilities are advantageous for field applications because they permit relatively high concentrations of the flushing agent. In order for cyclodextrin to become a feasible remediative alternative, it must be demonstrate a short term resistance to biodegradation during field application, but ultimately biodegrade so as not to pose a long term presence in the aquifer. The potential for degradation of cyclodextrin as well as changes in the chlorinated solvents and groundwater geochemistry were examined during the post monitoring of a field demonstration in a shallow aquifer at Little Creek Naval Amphibious Base in Virginia. It was found that a portion of the cyclodextrin remaining in the aquifer after the cessation of field activities biodegraded during the 425 days of post monitoring. This degradation also led to the degradation of the chlorinated solvents trichloroethylene and 1,1-trichloroethane through both biological and chemical processes. The aquifer remained anaerobic with average dissolved oxygen levels below 0.5 mg/L. Dissolved nitrate and sulfate concentrations within the cyclodextrin plume decreased due their being used as terminal electron acceptors during the degradation of the cyclodextrin. The concentrations of total iron at the field site showed no

  16. Design of Safer Flame Retardant Textiles through Inclusion Complex Formation with Cyclodextrins: A Combined Experimental and Modeling Study

    NASA Astrophysics Data System (ADS)

    Zhang, Nanshan

    Triphenyl phosphate (TPP) is widely used as a phosphorus flame retardant. It is also one component of a commercial flame retardant mixture known as Firemaster 550. TPP is likely to be released into the environment due to its high volatility and has been detected at a concentration as high as 47,000 ng/m3 in air. Recent studies have also indicated that FRs like TPP could contribute to obesity and osteoporosis in humans. Cyclodextrins (CDs) are enzymatic degradation products of starch and consist of several (alpha-1,4)-linked alpha-Dglucopyranose units. CDs own a hydrophilic outside and a hydrophobic inner cavity, which enables the formation of non-covalently bonded cyclodextrin inclusion complexes (CD-ICs) with a vast array of molecules. We hypothesize that the formation of inclusion complexes between TPP and cyclodextrins will reduce its exposure yet also retain flame retarding properties of TPP, since the formation of FR-CD-ICs is expected to eliminate unnecessary loss of FRs, especially volatile FR compounds like TPP, and release them only during a fire when they are actually needed. After creating the TPP-beta-CD-IC, we applied it to polyethylene terephthalate (PET) films by a hot press technique. Flame tests indicated TPP-beta-CD-IC exhibited flame resistant performance matching that of neat TPP, even though much less TPP was contained in its beta-CD-IC. Incorporation of FRs and other chemical additives into textile substrates in the form of their crystalline CD-ICs is a promising way to reduce the exposure of hazardous chemicals to humans and to our environment while not impacting their efficacy. Two other parent CDs (alpha-CD and gamma-CD) were applied and their abilities to form ICs with guest TPP were studied. Results from a series of characterization methods, including FTIR, DSC, TGA, XRD and NMR indicated the successful synthesis of TPP-gamma-CD-IC via two routes. However, alpha-CD appears unable to form an IC with TPP, which is likely attributable to a

  17. Thermodynamic study on the effects of β-cyclodextrin inclusion with berberine

    NASA Astrophysics Data System (ADS)

    Yu, Jun-Sheng; Wei, Fang-Di; Gao, Wei; Zhao, Chang-Chun

    2002-01-01

    The fluorescence enhancement of berberine (Berb) as a result of complex with β-cyclodextrin (β-CD) is investigated. The association constants of α-CD and β-CD with Berb are 60 and 137 M -1 at 20 °C in pH 7.20 aqueous solution. Effects of temperature on the forming inclusion complexes of β-CD with Berb have been examined through using fluorescence titration. Enthalpy and entropy values calculated from fluorescence data are -33.7·kJ mol -1 and 74.3 J·mol -1·K -1, respectively. It was found that the dielectric constant of β-CD cavity is about 24 in a rough analogy with absolute alcohol. These results suggest that the extrusion of 'high energy water' molecules from the cavity of β-CD and hydrophobic interaction upon the inclusion complex formation are the main forces of the inclusion reaction. Effect of pH on the association of β-CD with Berb was also studied. Mechanism of the inclusion of β-CD with Berb is further studied by absorption and NMR measurements. Results show that β-CD forms a 1:1 inclusion complex with Berb.

  18. Peptides: β-cyclodextrin inclusion compounds as highly effective antimicrobial and anti-epithelial proliferation agents.

    PubMed

    Consuegra, Jessika; de Lima, Maria Elena; Santos, Daniel; Sinisterra, Rubén Dario; Cortés, Maria Esperanza

    2013-12-01

    The use of antimicrobial peptides (AMPs) as therapeutic agents for periodontal infections has great advantages, such as broad spectrum of action, low toxicity, and limited bacterial resistance. However, their practical use is limited because of the large amount of peptide required to exercise the microbicidal function. LyeTxI, LL37f, and KR12 cationic peptides were prepared with β-cyclodextrin (βCD) at 1:1 molar ratios. The susceptibility of Porphyromonas gingivalis, Aggregatibacter actinomycetemcomitans, and Fusobacterium nucleatum were assessed in anaerobic conditions. Cytotoxicity assays were performed using osteoblast and Caco-2 epithelial cells, and hemolytic activity was assessed on rabbit erythrocytes at an absorbance of 414 nm. Parameters of surface roughness and electrical charge were established by atomic force microscopy and zeta (ζ) potential, respectively. AMP/βCDs drastically decreased the peptide concentration required for activity against the bacteria tested. Moreover, AMPs associated with βCD were able to modify cell-surface parameters, such as roughness and ζ potential. On the other hand, AMP/βCD did not alter the degree of hemolysis induced by the pure AMPs. The effective concentration at half-maximum values of the peptides and compounds on osteoblasts were greater than the concentrations required to achieve inhibition of bacterial growth in all the species tested. AMP/βCDs inhibited the proliferation of Caco-2 epithelial cells in a more efficient manner than AMPs alone. AMP/βCD compounds more effectively inhibit periodontopathogenic bacteria than AMPs alone, with the additional ability of inhibiting the proliferation of epithelial cells at concentrations that are non-cytotoxic for osteoblasts and erythrocytes.

  19. [In-vitro evaluation of cinnarizine as a competing agent to beta-cyclodextrin inclusion complexes: effect of cinnarizine on the membrane permeation rate of progesterone from its beta-cyclodextrin inclusion complex].

    PubMed

    Muraoka, Atsushi; Tokumura, Tadakazu; Machida, Yoshiharu

    2008-01-01

    The use of competing agents is considered a powerful tool for the development of a drug-delivery system with drug/cyclodextrin inclusion complexes. However, there are very few studies examining this issue. To explain this phenomenon, it was thought that a competing agent with a sufficiently high stability constant had not yet been reported. In this study, cinnarizine (CN), which has a high stability constant with beta-cyclodextrin (beta-CD) and unique solubility characteristics, was selected, and its ability as a competing agent was examined in a membrane permeability study. The permeability study showed that the permeation rates of the drugs flurbiprofen, progesterone, and spironolactone decreased with their stability constants with the addition of beta-CD. In one of the drugs, progesterone (Pro), the decrease was restored by the addition of CN. The amount of CN added was a 1:1 molar ratio to the amount of Pro. However, no similar action was induced with the addition of DL-phenylalanine (Phe) in the permeation study at the 1:5 (Pro:Phe) molar ratio. These finding indicate that CN acts as a competing agent, and its action is much stronger than that of Phe.

  20. Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

    PubMed Central

    Letort, Sophie; Bosco, Michaël; Cornelio, Benedetta; Brégier, Frédérique; Daulon, Sébastien; Gouhier, Géraldine

    2017-01-01

    New derivatives of cyclodextrins were prepared in order to determine the relative importance of the structural key elements involved in the degradation of organophosphorus nerve agents. To avoid a competitive inclusion between the organophosphorus substrate and the iodosobenzoate group, responsible for its degradation, the latter group had to be covalently bound to the cyclodextrin scaffold. Although the presence of the α nucleophile iodosobenzoate was a determinant in the hydrolysis process, an imidazole group was added to get a synergistic effect towards the degradation of the agents. The degradation efficiency was found to be dependent on the relative position of the heterocycle towards the reactive group as well as on the nature of the organophosphorus derivative. PMID:28382180

  1. Structure-efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds.

    PubMed

    Letort, Sophie; Bosco, Michaël; Cornelio, Benedetta; Brégier, Frédérique; Daulon, Sébastien; Gouhier, Géraldine; Estour, François

    2017-01-01

    New derivatives of cyclodextrins were prepared in order to determine the relative importance of the structural key elements involved in the degradation of organophosphorus nerve agents. To avoid a competitive inclusion between the organophosphorus substrate and the iodosobenzoate group, responsible for its degradation, the latter group had to be covalently bound to the cyclodextrin scaffold. Although the presence of the α nucleophile iodosobenzoate was a determinant in the hydrolysis process, an imidazole group was added to get a synergistic effect towards the degradation of the agents. The degradation efficiency was found to be dependent on the relative position of the heterocycle towards the reactive group as well as on the nature of the organophosphorus derivative.

  2. Enantioseparation of mandelic acid derivatives by high performance liquid chromatography with substituted β-cyclodextrin as chiral mobile phase additive and evaluation of inclusion complex formation

    PubMed Central

    Tong, Shengqiang; Zhang, Hu; Shen, Mangmang

    2014-01-01

    The enantioseparation of ten mandelic acid derivatives was performed by reverse phase high performance liquid chromatography with hydroxypropyl-β-cyclodextrin (HP-β-CD) or sulfobutyl ether-β-cyclodextrin (SBE-β-CD) as chiral mobile phase additives, in which inclusion complex formations between cyclodextrins and enantiomers were evaluated. The effects of various factors such as the composition of mobile phase, concentration of cyclodextrins and column temperature on retention and enantioselectivity were studied. The peak resolutions and retention time of the enantiomers were strongly affected by the pH, the organic modifier and the type of β-cyclodextrin in the mobile phase, while the concentration of buffer solution and temperature had a relatively low effect on resolutions. Enantioseparations were successfully achieved on a Shimpack CLC-ODS column (150×4.6 mm i.d., 5 μm). The mobile phase was a mixture of acetonitrile and 0.10 mol L-1 of phosphate buffer at pH 2.68 containing 20 mmol L-1 of HP-β-CD or SBE-β-CD. Semi-preparative enantioseparation of about 10 mg of α-cyclohexylmandelic acid and α-cyclopentylmandelic acid were established individually. Cyclodextrin-enantiomer complex stoichiometries as well as binding constants were investigated. Results showed that stoichiomertries for all the inclusion complex of cyclodextrin-enantiomers were 1:1. PMID:24893270

  3. Characterization, phase solubility and molecular modeling of α-cyclodextrin/pyrimethamine inclusion complex

    NASA Astrophysics Data System (ADS)

    Araujo, Marcia Valeria Gaspar de; Macedo, Osmir F. L.; Nascimento, Cristiane da Cunha; Conegero, Leila Souza; Barreto, Ledjane Silva; Almeida, Luis Eduardo; Costa, Nivan Bezerra da; Gimenez, Iara F.

    2009-02-01

    An inclusion complex between the dihydrofolate reductase inhibitor pyrimethamine (PYR) and α-cyclodextrin (α-CD) was prepared and characterized. From the phase-solubility diagram, a linear increase of PYR solubility was verified as a function of α-CD concentration, suggesting the formation of a soluble complex. A 1:1 host-guest stoichiometry can be proposed according to the Job's plot, obtained from the difference of PYR fluorescence intensity in the presence and absence of α-CD. Differential scanning calorimetry (DSC) measurements provided additional evidences of complexation such as the absence of the endothermic peak assigned to the melting of the drug. The inclusion mode characterized by two-dimensional 1H NMR spectroscopy (ROESY) involves penetration of the p-chlorophenyl ring into the α-CD cavity, in agreement to the orientation optimized by molecular modeling methods.

  4. Antimicrobial coatings on polyethylene terephthalate based on curcumin/cyclodextrin complex embedded in a multilayer polyelectrolyte architecture.

    PubMed

    Shlar, Ilya; Droby, Samir; Rodov, Victor

    2018-04-01

    Bacterial contamination is a growing concern worldwide. The aim of this work was to develop an antimicrobial coating based on curcumin-cyclodextrin inclusion complex and using polyethylene terephthalate (PET) film as a support matrix. After a pre-treatment aimed to provide sufficient electric charge to the PET surface, it was electrostatically coated with repeated multilayers comprising alternately deposited positively-charged poly-l-lysine (PLL) and negatively-charged poly-l-glutamic acid (PLGA) and carboxymethyl-β-cyclodextrin (CMBCD). The coatings had an architecture (PLL-PLGA) 6 -(PLL-PLGA-PLL-CMBCD) n , with the number of repeated multilayers n varying from 5 to 20. The CMBCD molecules were either covalently cross-linked using carbodiimide crosslinker chemistry or left unbound. The surface morphology, structure and elemental composition of the coatings were analysed by scanning electron microscopy and energy dispersive x-ray spectroscopy. To impart antimicrobial properties to the coatings they were loaded with a natural phenolic compound curcumin forming inclusion complexes with β-cyclodextrin. The non-cross-linked coatings showed bactericidal activity towards Escherichia coli in the dark, and this activity was further enhanced upon illumination with white light. Curcumin was released from the non-cross-linked coatings into an aqueous medium in the form of cyclodextrin inclusion complex. After the cross-linking, the coating lost its dark antimicrobial activity but retained the photodynamic properties. Stabilized cross-linked curcumin-loaded coatings can serve a basis for developing photoactivated antimicrobial surfaces controlling bacterial contamination and spread. Copyright © 2018 Elsevier B.V. All rights reserved.

  5. Analytical techniques for characterization of cyclodextrin complexes in the solid state: A review.

    PubMed

    Mura, Paola

    2015-09-10

    Cyclodextrins are cyclic oligosaccharides able to form inclusion complexes with a variety of hydrophobic guest molecules, positively modifying their physicochemical properties. A thorough analytical characterization of cyclodextrin complexes is of fundamental importance to provide an adequate support in selection of the most suitable cyclodextrin for each guest molecule, and also in view of possible future patenting and marketing of drug-cyclodextrin formulations. The demonstration of the actual formation of a drug-cyclodextrin inclusion complex in solution does not guarantee its existence also in the solid state. Moreover, the technique used to prepare the solid complex can strongly influence the properties of the final product. Therefore, an appropriate characterization of the drug-cyclodextrin solid systems obtained has also a key role in driving in the choice of the most effective preparation method, able to maximize host-guest interactions. The analytical characterization of drug-cyclodextrin solid systems and the assessment of the actual inclusion complex formation is not a simple task and involves the combined use of several analytical techniques, whose results have to be evaluated together. The objective of the present review is to present a general prospect of the principal analytical techniques which can be employed for a suitable characterization of drug-cyclodextrin systems in the solid state, evidencing their respective potential advantages and limits. The applications of each examined technique are described and discussed by pertinent examples from literature. Copyright © 2015 Elsevier B.V. All rights reserved.

  6. Analytical techniques for characterization of cyclodextrin complexes in aqueous solution: a review.

    PubMed

    Mura, Paola

    2014-12-01

    Cyclodextrins are cyclic oligosaccharides endowed with a hydrophilic outer surface and a hydrophobic inner cavity, able to form inclusion complexes with a wide variety of guest molecules, positively affecting their physicochemical properties. In particular, in the pharmaceutical field, cyclodextrin complexation is mainly used to increase the aqueous solubility and dissolution rate of poorly soluble drugs, and to enhance their bioavailability and stability. Analytical characterization of host-guest interactions is of fundamental importance for fully exploiting the potential benefits of complexation, helping in selection of the most appropriate cyclodextrin. The assessment of the actual formation of a drug-cyclodextrin inclusion complex and its full characterization is not a simple task and often requires the use of different analytical methods, whose results have to be combined and examined together. The purpose of the present review is to give, as much as possible, a general overview of the main analytical tools which can be employed for the characterization of drug-cyclodextrin inclusion complexes in solution, with emphasis on their respective potential merits, disadvantages and limits. Further, the applicability of each examined technique is illustrated and discussed by specific examples from literature. Copyright © 2014 Elsevier B.V. All rights reserved.

  7. ESR, electrochemical and cyclodextrin-inclusion studies of triazolopyridyl pyridyl ketones and dipyridyl ketones derivatives

    NASA Astrophysics Data System (ADS)

    Olea-Azar, C.; Abarca, B.; Norambuena, E.; Opazo, L.; Jullian, C.; Valencia, S.; Ballesteros, R.; Chadlaoui, M.

    2008-11-01

    The electron spin resonance (ESR) spectra of free radicals obtained by electrolytic reduction of triazolopyridyl pyridyl ketones and dipyridyl ketones derivatives were measured in dimethylsulfoxide (DMSO). The hyperfine patterns indicate that the spin density delocalization is dependent of the rings presented in the molecule. The electrochemistry of these compounds was characterized using cyclic voltammetry, in DMSO as solvent. When one carbonyl is present in the molecule one step in the reduction mechanism was observed while two carbonyl are present two steps were detected. The first wave was assigned to the generation of the correspondent free radical species, and the second wave was assigned to the dianion derivatives. The phase-solubility measurements indicated an interaction between molecules selected and cyclodextrins in water. These inclusion complexes are 1:1 with βCD, and HP-βCD. The values of Ks showed a different kind of complexes depending on which rings are included. AM1 and DFT calculations were performed to obtain the optimized geometries, theoretical hyperfine constants, and spin distributions, respectively. The theoretical results are in complete agreement with the experimental ones.

  8. Use of cyclodextrins as a cosmetic delivery system for fragrance materials: linalool and benzyl acetate.

    PubMed

    Numanoğlu, Ulya; Sen, Tangül; Tarimci, Nilüfer; Kartal, Murat; Koo, Otilia M Y; Onyüksel, Hayat

    2007-10-19

    The aim of this study was to increase the stability and water solubility of fragrance materials, to provide controlled release of these compounds, and to convert these substances from liquid to powder form by preparing their inclusion complexes with cyclodextrins (CDs). For this purpose, linalool and benzyl acetate were chosen as the fragrance materials. The use of beta-cyclodextrin (beta CD) and 2-hydroxypropyl-beta-cyclodextrin (2-HP beta CD) for increasing the solubility of these 2 fragrance materials was studied. Linalool and benzyl acetate gave a B-type diagram with beta CD, whereas they gave an A(L)-type diagram with 2-HP beta CD. Therefore, complexes of fragrance materials with 2-HP beta CD at 1:1 and 1:2 molar ratios (guest:host) were prepared. The formation of inclusion complexes was confirmed using proton nuclear magnetic resonance ((1)H-NMR) spectroscopy and circular dichroism spectroscopy. The results of the solubility studies showed that preparing the inclusion complex with 2-HP beta CD at a 1:1 molar ratio increased the solubility of linalool 5.9-fold and that of benzyl acetate 4.2-fold, whereas the complexes at a 1:2 molar ratio increased the solubility 6.4- and 4.5-fold for linalool and benzyl acetate, respectively. The stability and in vitro release studies were performed on the gel formulations prepared using uncomplexed fragrance materials or inclusion complexes of fragrance materials at a 1:1 molar ratio. It was observed that the volatility of both fragrance materials was decreased by preparing the inclusion complexes with 2-HP beta CD. Also, in vitro release data indicated that controlled release of fragrances could be possible if inclusion complexes were prepared.

  9. Molecular structures of the inclusion complexes beta-cyclodextrin-1,2-bis(4-aminophenyl)ethane and beta-cyclodextrin-4,4'-diaminobiphenyl; packing of dimeric beta-cyclodextrin inclusion complexes.

    PubMed

    Giastas, Petros; Yannakopoulou, Konstantina; Mavridis, Irene M

    2003-04-01

    The present investigation is part of an ongoing study on the influence of the long end-functonalized guest molecules DBA and BNZ in the crystal packing of beta-cyclodextrin (betaCD) dimeric complexes. The title compounds are 2:2 host:guest complexes showing limited host-guest hydrogen bonding at the primary faces of the betaCD dimers. Within the betaCD cavity the guests exhibit mutual pi...pi interactions and between betaCD dimers perpendicular NH...pi interactions. The DBA guest molecule exhibits one extended and two bent conformations in the complex. The BNZ guest molecule is not planar inside betaCD, in contrast to the structure of BNZ itself, which indicates that the cavity isolates the molecules and forbids the pi...pi stacking of the aromatic rings. NMR spectroscopy studies show that in aqueous solution both DBA and BNZ form strong complexes that have 1:1 stoichiometry and structures similar to the solid state ones. The relative packing of the dimers is the same in both complexes. The axes of two adjacent dimers form an angle close to 20 degrees and have a lateral displacement approximately 2.45 A, both of which characterize the screw-channel mode of packing. Although the betaCD/BNZ complex indeed crystallizes in a space group characterizing the latter mode, the betaCD/DBA complex crystallizes in a space group with novel dimensions not resembling any of the packing modes reported so far. The new lattice is attributed to the three conformations exhibited by the guest in the crystals. However, this lattice can be transformed into another, which is isostructural to that of the betaCD/BNZ inclusion complex, if the conformation of the guest is not taken into account.

  10. Regioselective self-acylating cyclodextrins in organic solvent

    NASA Astrophysics Data System (ADS)

    Cho, Eunae; Yun, Deokgyu; Jeong, Daham; Im, Jieun; Kim, Hyunki; Dindulkar, Someshwar D.; Choi, Youngjin; Jung, Seunho

    2016-03-01

    Amphiphilic cyclodextrins have been synthesized with self-acylating reaction using vinyl esters in dimethylformamide. In the present study no base, catalyst, or enzyme was used, and the structural analyses using thin layer chromatography, nuclear magnetic resonance spectroscopy and mass spectrometry show that the cyclodextrin is substituted preferentially by one acyl moiety at the C2 position of the glucose unit, suggesting that cyclodextrin functions as a regioselective catalytic carbohydrate in organic solvent. In the self-acylation, the most acidic OH group at the 2-position and the inclusion complexing ability of cyclodextrin were considered to be significant. The substrate preference was also observed in favor of the long-chain acyl group, which could be attributed to the inclusion ability of cyclodextrin cavity. Furthermore, using the model amphiphilic building block, 2-O-mono-lauryl β-cyclodextrin, the self-organized supramolecular architecture with nano-vesicular morphology in water was investigated by fluorescence spectroscopy, dynamic light scattering and transmission electron microscopy. The cavity-type nano-assembled vesicle and the novel synthetic methods for the preparation of mono-acylated cyclodextrin should be of great interest with regard to drug/gene delivery systems, functional surfactants, and carbohydrate derivatization methods.

  11. β-Cyclodextrin inclusion complex: preparation, characterization, and its aspirin release in vitro

    NASA Astrophysics Data System (ADS)

    Zhou, Hui-Yun; Jiang, Ling-Juan; Zhang, Yan-Ping; Li, Jun-Bo

    2012-09-01

    In this work, the optimal clathration condition was investigated for the preparation of aspirin-β-cyclodextrin (Asp-β-CD) inclusion complex using design of experiment (DOE) methodology. A 3-level, 3-factor Box-Behnken design with a total of 17 experimental runs was used. The Asp-β-CD inclusion complex was prepared by saturated solution method. The influence on the embedding rate was investigated, including molar ratio of β-CD to Asp, clathration temperature and clathration time, and the optimum values of such three test variables were found to be 0.82, 49°C and 2.0 h, respectively. The embedding rate could be up to 61.19%. The formation of the bonding between -COOH group of Asp and O-H group of β-CD might play an important role in the process of clathration according to FT-IR spectra. Release kinetics of Asp from inclusion complex was studied for the evaluation of drug release mechanism and diffusion coefficients. The results showed that the drug release from matrix occurred through Fickian diffusion mechanism. The cumulative release of Asp reached only 40% over 24 h, so the inclusion complex could potentially be applied as a long-acting delivery system.

  12. Biosynthesis of ketomycin. (II) biomimetic model for beta-lactamase catalysis: host-guest interactions in cyclodextrin-penicillin inclusion complex

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Mak, H.W.

    The antibiotic ketomycin is formed from shikimic acid via chorismic acid and prephenic acid. Phenylalanine and 2',5'-dihydrophenylalanine derived from shikimic acid are not intermediates in the biosynthesis. Degradation of ketomycin derived from (1,6-/sup 14/C)shikimic acid showed that prephenic acid is converted into ketomycin with stereospecific discrimination between the two enantiotopic edges of the ring, the pro-S-R edge giving rise to the C-2', C-3' side of the cyclohexane ring of ketomycin. The resistance of pathogenic bacteria to the action of ..beta..-lactam antibiotics is mainly ascribed to their ability to produce ..beta..-lactamase to cleave the ..beta..-lactam ring. It is essential to understandmore » the molecular nature of ..beta..-lactamase-penicillin recognition for designing and formulating more effective ..beta..-lactam antibiotics. A biomimetic study of ..beta..-lactamase is therefore initiated. To meet the requirements of hydrophobic and serine protease characteristics of ..beta..-lactamase, ..cap alpha..-cyclodextrin is chosen as a biomimetic model for ..beta..-lactamase. The structural specificity and the chemical dynamics of ..cap alpha..-cyclodextrin-phenoxymethyl penicillin inclusion complex in solid state and in solution have been determined by IR and NMR spectroscopy. The spectral results strongly indicate that the phenyl portion of the phenoxymethyl penicillin forms a stable inclusion complex with the hydrophobic cavity of ..cap alpha..-cyclodextrin in solution as well as in the solid state. Kinetic studies followed by /sup 1/HNMR and HPLC analyses under alkaline condition have shown that the ..cap alpha..-cyclodextrin mimics the catalytic function of serine of ..beta..-lactamase in the stereospecific hydrolysis of the ..beta..-lactam ring of phenoxymethyl penicillin.« less

  13. Cyclodextrins: A Weapon in the Fight Against Antimicrobial Resistance

    NASA Astrophysics Data System (ADS)

    Wong, Chew Ee; Dolzhenko, Anton V.; Lee, Sui Mae; Young, David James

    Antimicrobial resistance poses one of the most serious global challenges of our age. Cyclodextrins (CDs) are widely utilized excipients in formulations because of their solubilizing properties, low toxicity, and low inflammatory response. This review summarizes recent investigations of antimicrobial agents involving CDs and CD-based antimicrobial materials. CDs have been employed for antimicrobial applications either through formation of inclusion complexes or by chemical modification of their hydroxyl groups to tailor pharmaceutically active compounds. Applications of these CD inclusion complexes include drug delivery, antimicrobial coatings on materials (e.g., biomedical devices and implants) and antimicrobial dressings that help to prevent wound infections. There are relatively limited studies of chemically modified CDs with antimicrobial activity. The mechanism of action of antimicrobial CD inclusion complexes and derivatives needs further elucidation, but activity of CDs and their derivatives is often associated with their interaction with bacterial cell membranes.

  14. Study of production and pyrolysis characteristics of sweet orange flavor-β-cyclodextrin inclusion complex.

    PubMed

    Zhu, Guangyong; Xiao, Zuobing; Zhou, Rujun; Zhu, Yalun

    2014-05-25

    Flavor plays an important role and has been widely used in foods. Encapsulation can prevent the loss of volatile aromatic ingredients, provide protection and enhance the stability of the flavor. Kinetic and thermodynamic parameters are helpful in understanding the mechanism of molecular recognition between hosts and guests. This work focused on the study of production of a sweet orange flavor-β-cyclodextrin (CD) inclusion complex, and investigated the combination of flavor and β-CD by thermogravimetric analysis. Pyrolysis characteristics, kinetic and thermodynamic parameters of the flavor-β-CD inclusion complex were determined. The results showed that the flavor-β-CD inclusion complexes can form large aggregates in water. During thermal degradation of blank β-CD and flavor-β-CD inclusion complex, three main stages can be distinguished. The thermogravimetric (TG) curve of blank β-CD shows a leveling-off from room temperature to 250°C, while the TG curve of flavor-β-CD inclusion complex is downward sloping in this temperature range. Copyright © 2014 Elsevier Ltd. All rights reserved.

  15. Amphiphilic cyclodextrin nanoparticles.

    PubMed

    Varan, Gamze; Varan, Cem; Erdoğar, Nazlı; Hıncal, A Atilla; Bilensoy, Erem

    2017-10-15

    Cyclodextrins are cyclic oligosaccharides obtained by enzymatic digestion of starch. The α-, β- and γ- cyclodextrins contain respectively 6, 7 and 8 glucopyranose units, with primary and secondary hydroxyl groups located on the narrow and wider rims of a truncated cone shape structure. Such structure is that of a hydrophobic inner cavity with a hydrophilic outer surface allowing to interact with a wide range of molecules like ions, protein and oligonucleotides to form inclusion complexes. Many cyclodextrin applications in the pharmaceutical area have been widely described in the literature due to their low toxicity and low immunogenicity. The most important is to increase the solubility of hydrophobic drugs in water. Chemically modified cyclodextrin derivatives have been synthesized to enhance their properties and more specifically their pharmacological activity. Among these, amphiphilic derivatives were designed to build organized molecular structures, through selfassembling systems or by incorporation in lipid membranes, expected to improve the vectorization in the organism of the drug-containing cyclodextrin cavities. These derivatives can form a variety of supramolecular structures such as micelles, vesicles and nanoparticles. The purpose of this review is to summarize applications of amphiphilic cyclodextrins in different areas of drug delivery, particularly in protein and peptide drug delivery and gene delivery. The article highlights important amphiphilic cyclodextrin applications in the design of novel delivery systems like nanoparticles. Copyright © 2017 Elsevier B.V. All rights reserved.

  16. The effect of mechanical grinding on the formation, crystalline changes and dissolution behaviour of the inclusion complex of telmisartan and β-cyclodextrins.

    PubMed

    Borba, Paola Aline Amarante; Pinotti, Marihá; Andrade, George Ricardo Santana; da Costa, Nivan Bezerra; Olchanheski Junior, Luiz Renato; Fernandes, Daniel; de Campos, Carlos Eduardo Maduro; Stulzer, Hellen Karine

    2015-11-20

    Telmisartan (TEL) was entrapped into β-cyclodextrin aiming the improvement of its biopharmaceutical properties of low solubility. A solid state grinding process was used to prepare the molecular inclusion complex (MIC) for up to 30min. The inclusion ratio of drug and β-cyclodextrin was established as 1:2 and 1:3 (mol/mol) by phase solubility study and Job Plot. DSC, XRPD and FTIR confirmed the molecular interactions between TEL and β-cyclodextrin. Computer molecular modeling supports the presence of hydrogen bonds between guest and host and demonstrated the most probable complexes configuration. MIC_1:2_30 and MIC_1:3_30 enhanced the dissolution rate of the drug achieving a delivery rate comparable with the reference medicine available in the market (81% and 87% in 5min, for MIC_1:3_30 and Micardis(®), respectively). These formulations showed rapid and effective antihypertensive effect against angiotensin II in rats up to 180min, with statistically significant results against placebo and control in the first 30min after administration. Copyright © 2015 Elsevier Ltd. All rights reserved.

  17. Enhancement of bioavailability of cinnarizine from its beta-cyclodextrin complex on oral administration with DL-phenylalanine as a competing agent.

    PubMed

    Tokumura, T; Nanba, M; Tsushima, Y; Tatsuishi, K; Kayano, M; Machida, Y; Nagai, T

    1986-04-01

    The present investigation is concerned with an improvement of the bioavailability of cinnarizine by administering its beta-cyclodextrin complex together with another compound which competes with the beta-cyclodextrin molecule in complex formation in aqueous solution (competing agent). The bioavailability of cinnarizine on oral administration of the cinnarizine-beta-cyclodextrin inclusion complex was enhanced by the simultaneous administration of DL-phenylalanine as a competing agent, e.g., the AUC was 1.9 and 2.7 times as large as those of the cinnarizine-beta-cyclodextrin complex alone and cinnarizine alone, respectively. The enhancement of AUC and Cmax completely depended on the dose of DL-phenylalanine. It was found from these results that DL-phenylalanine acted as a competing agent in the GI tract and the minimum effective dose required of DL-phenylalanine might be 1 g for 50 mg of cinnarizine in the cinnarizine-beta-cyclodextrin complex. Evaluating the competing effect of DL-phenylalanine in vitro using an absorption simulator, it was found that the decreased penetration rate of cinnarizine through the artificial lipid barrier with addition of beta-cyclodextrin was restored with the addition of DL-phenylalanine.

  18. Novel "anchor modification" of polymeric biomaterial surfaces by the utilization of cyclodextrin inclusion complex supramolecules.

    PubMed

    Zhao, Xiaobin; Courtney, James M

    2009-07-01

    In this article, a novel approach for the surface modification of polymeric biomaterials by the utilization of supramolecules was studied. The supramolecules selected were cyclodextrin inclusion complexes (CICs). The biomaterial selected for surface modification was plasticized poly (vinyl chloride) (PVC-P). Results indicate that when the CICs were blended into PVC-P, they tend to migrate and "anchor" on the surface to achieve a remarkable protein-resistant surface, with improved blood compatibility. In comparison with a physical mixture of cyclodextrins and a "guest" molecule, such as poly(ethylene oxide) (PEO)-poly(propylene oxide) (PPO)-PEO and PPO-PEO-PPO for PVC-P modification, CICs modified PVC-P are more consistent in processing and achieve reproducible surface characteristics. Based on this study, a novel "anchor modification" was proposed regarding CICs modified surface. This "anchor modification" is likely to reduce plasticizer extraction from PVC-P and also can be utilized for the modification of polymers other than PVC-P.

  19. Cyclodextrins improving the physicochemical and pharmacological properties of antidepressant drugs: a patent review.

    PubMed

    Diniz, Tâmara Coimbra; Pinto, Tiago Coimbra Costa; Menezes, Paula Dos Passos; Silva, Juliane Cabral; Teles, Roxana Braga de Andrade; Ximenes, Rosana Christine Cavalcanti; Guimarães, Adriana Gibara; Serafini, Mairim Russo; Araújo, Adriano Antunes de Souza; Quintans Júnior, Lucindo José; Almeida, Jackson Roberto Guedes da Silva

    2018-01-01

    Depression is a serious mood disorder and is one of the most common mental illnesses. Despite the availability of several classes of antidepressants, a substantial percentage of patients are unresponsive to these drugs, which have a slow onset of action in addition to producing undesirable side effects. Some scientific evidence suggests that cyclodextrins (CDs) can improve the physicochemical and pharmacological profile of antidepressant drugs (ADDs). The purpose of this paper is to disclose current data technology prospects involving antidepressant drugs and cyclodextrins. Areas covered: We conducted a patent review to evaluate the antidepressive activity of the compounds complexed in CDs, and we analyzed whether these complexes improved their physicochemical properties and pharmacological action. The present review used 8 specialized patent databases for patent research, using the term 'cyclodextrin' combined with 'antidepressive agents' and its related terms. We found 608 patents. In the end, considering the inclusion criteria, 27 patents reporting the benefits of complexation of ADDs with CDs were included. Expert opinion: The use of CDs can be considered an important tool for the optimization of physicochemical and pharmacological properties of ADDs, such as stability, solubility and bioavailability.

  20. NMR study on the stabilization and chiral discrimination of sulforaphane enantiomers and analogues by cyclodextrins.

    PubMed

    Recio, Rocío; Elhalem, Eleonora; Benito, Juan M; Fernández, Inmaculada; Khiar, Noureddine

    2018-05-01

    Sulforaphane (SFN), a phytochemical isolated from broccoli, is an important antitumoral compound with additional beneficial effect on other important diseases. However, the chemical instability of SFN has hampered its clinical use. In order to circumvent this problem, we report the first comparative study on the inclusion complexes of SFN and SFN homologues with different cyclodextrins by NMR spectroscopy. From this study it has been shown that α-CD is the most indicated cyclodextrin for the stabilization of SFN and SFN homologues, and that the highest affinity constant is that of the isothiocyanate obtained from the wasabi. Furthermore, the study of the inclusion complexes of α-CD and the non-natural SFN and analogues with S absolute configuration at sulfur shows for the first time that α-CD is able to discriminate between the two enantiomers, with the natural R enantiomers forming the inclusion complexes with higher affinity. Copyright © 2017 Elsevier Ltd. All rights reserved.

  1. The role of cyclodextrins in ORAC-fluorescence assays. antioxidant capacity of tyrosol and caffeic acid with hydroxypropyl-β-cyclodextrin.

    PubMed

    García-Padial, Marcos; Martínez-Ohárriz, María Cristina; Navarro-Blasco, Iñigo; Zornoza, Arantza

    2013-12-18

    Tyrosol and caffeic acid are biophenols that contribute to the beneficial properties of virgin olive oil. The influence of hydroxypropyl-β-cyclodextrin (HPβ-CD) on their respective antioxidant capacities was analyzed. The ORAC antioxidant activity of tyrosol (expressed as μM Trolox equivalents/μM Tyrosol) was 0.83 ± 0.03 and it increased up to 1.20 ± 0.11 in the presence of 0.8 mM HPβ-CD. However, the ORAC antioxidant activity of caffeic acid experienced no change. The different effect of HPβ-CD on each compound was discussed. In addition, the effect of increasing concentrations of different cyclodextrins in the development of ORAC-fluorescence (ORAC-FL) assays was studied. The ORAC signal was higher for HPβ-CD, followed by Mβ-CD, β-CD, γ-CD and finally α-CD. These results could be explained by the formation of inclusion complexes with fluorescein.

  2. Intestinal Permeability of β-Lapachone and Its Cyclodextrin Complexes and Physical Mixtures.

    PubMed

    Mangas-Sanjuan, Victor; Gutiérrez-Nieto, Jorge; Echezarreta-López, Magdalena; González-Álvarez, Isabel; González-Álvarez, Marta; Casabó, Vicente-Germán; Bermejo, Marival; Landin, Mariana

    2016-12-01

    β-Lapachone (βLAP) is a promising, poorly soluble, antitumoral drug. βLAP combination with cyclodextrins (CDs) improves its solubility and dissolution but there is not enough information about the impact of cyclodextrins on βLAP intestinal permeability. The objectives of this work were to characterize βLAP intestinal permeability and to elucidate cyclodextrins effect on the dissolution properties and on the intestinal permeability. The final goal was to evaluate CDs influence on the oral absorption of βLAP. Binary systems (physical mixtures and inclusion complexes) including βLAP and CDs (β-cyclodextrin: βCD, random-methyl-β-cyclodextrin: RMβCD and sulfobutylether-β-cyclodextrin: SBEβCD) have been prepared and analysed by differential scanning calorimetry. βLAP (and its combinations with CDs) absorption rate coefficients and effective permeability values have been determined in vitro in MDCK or MDCK-Mdr1 monolayers and in situ in rat by a closed loop perfusion technique. DSC results confirmed the formation of the inclusion complexes. βLAP-CDs inclusion complexes improve drug solubility and dissolution rate in comparison with physical mixtures. βLAP presented a high permeability value which can provide complete oral absorption. Its oral absorption is limited by its low solubility and dissolution rate. Cyclodextrin (both as physical mixtures and inclusion complexes) showed a positive effect on the intestinal permeability of βLAP. Complexation with CDs does not reduce βLAP intestinal permeability in spite of the potential negative effect of the reduction in free fraction of the drug. The use of RMβCD or SBEβCD inclusion complexes could benefit βLAP oral absorption by enhancing its solubility, dissolution rate and permeability.

  3. Characterization of aspartame-cyclodextrin complexation.

    PubMed

    Sohajda, Tamás; Béni, Szabolcs; Varga, Erzsébet; Iványi, Róbert; Rácz, Akos; Szente, Lajos; Noszál, Béla

    2009-12-05

    The inclusion complex formation of aspartame (guest) and various cyclodextrins (host) were examined using 1H NMR titration and capillary electrophoresis. Initially the protonation constants of aspartame were determined by NMR-pH titration with in situ pH measurement to yield log K1=7.83 and log K2=2.96. Based on these values the stability of the complexes formed by aspartame and 21 different cyclodextrins (CDs) were studied at pH 2.5, pH 5.2 and pH 9.0 values where aspartame exists predominantly in monocationic, zwitterionic and monoanionic form, respectively. The host cyclodextrin derivatives differed in various sidechains, degree of substitution, charge and purity so that the effect of these properties could be examined systematically. Concerning size, the seven-membered beta-cyclodextrin and its derivatives have been found to be the most suitable host molecules for complexation. Highest stability was observed for the acetylated derivative with a degree of substitution of 7. The purity of the CD enhanced the complexation while the degree of substitution did not provide obvious consequences. Finally, geometric aspects of the inclusion complex were assessed by 2D ROESY NMR and molecular modelling which proved that the guest's aromatic ring enters the wider end of the host cavity.

  4. Cyclodextrins sequester neuroactive steroids and differentiate mechanisms that rate limit steroid actions

    PubMed Central

    Shu, H-J; Zeng, C-M; Wang, C; Covey, D F; Zorumski, C F; Mennerick, S

    2006-01-01

    Background and purpose: Neuroactive steroids are potent modulators of GABAA receptors and are thus of interest for their sedative, anxiolytic, anticonvulsant and anaesthetic properties. Cyclodextrins may be useful tools to manipulate neuroactive effects of steroids on GABAA receptors because cyclodextrins form inclusion complexes with at least some steroids that are active at the GABAA receptor, such as (3α,5α)-3-hydroxypregnan-20-one (3α5αP, allopregnanolone). Experimental approach: To assess the versatility of cyclodextrins as steroid modulators, we investigated interactions between γ-cyclodextrin and neuroactive steroids of different structural classes. Key results: Both a bioassay based on electrophysiological assessment of GABAA receptor function and optical measurements of cellular accumulation of a fluorescent steroid analogue suggest that γ-cyclodextrin sequesters steroids rather than directly influencing GABAA receptor function. Neither a 5β-reduced A/B ring fusion nor a sulphate group at carbon 3 affected the presumed inclusion complex formation between steroid and γ-cyclodextrin. Apparent dissociation constants for interactions between natural steroids and γ-cyclodexrin ranged from 10-60 μM. Although γ-cyclodextrin accommodates a range of natural and synthetic steroids, C11 substitutions reduced inclusion complex formation. Using γ-cyclodextrin to remove steroid not directly bound to GABAA receptors, we found that cellular retention of receptor-unbound steroid rate limits potentiation by 3α- hydroxysteroids but not inhibition by sulphated steroids. Conclusions and implications: We conclude that γ-cyclodextrins can be useful, albeit non-specific, tools for terminating the actions of multiple classes of naturally occurring neuroactive steroids. PMID:17160009

  5. Formation of β-cyclodextrin inclusion enhances the stability and aqueous solubility of natural borneol.

    PubMed

    Su, Jianyu; Chen, Jianping; Li, Lin; Li, Bing; Shi, Lei; Chen, Ling; Xu, Zhenbo

    2012-06-01

    The aims of this study were to optimize the preparation conditions of natural borneol/β-cyclodextrin (NB/β-CD) inclusion complex by ultrasound method, and to investigate its improvement of stability and solubility. The complex was characterized by different various spectroscopic techniques including Fourier transform infrared spectroscopy, X-ray diffractometry, and differential scanning calorimetry. The results demonstrate that NB could be efficiently loaded into β-CD to form an inclusion complex by ultrasound method at a molar ratio of 1: 1and mass ratio of 1: 6. The complex exhibited different physicochemical characteristics from that of free NB. Typically, formation of β-CD inclusion significantly enhanced the stability and aqueous solubility of NB. Natural borneol (NB) has the potential to be widely used in the fields of medical and functional food, due to its specificity. However, the disadvantages of unstability in the preparation and storage process due to its easy sublimation and the low water solubility limit its application. This research provides an effective way to improve the solubility and stability of NB by preparing NB/β-CD inclusion complex. Furthermore, theoretical basis is also provided for the application development of NB. © 2012 Institute of Food Technologists®

  6. New β-Cyclodextrin Entrapped in Polyethyleneimine Film-Modified Electrodes for Pharmaceutical Compounds Determination

    PubMed Central

    Fritea, Luminţa; Tertiş, Mihaela; Cristea, Cecilia; Săndulescu, Robert

    2013-01-01

    The electrochemical behavior of ascorbic acid and uric acid on glassy carbon bare electrodes and ones modified with β-cyclodextrin entrapped in polyethyleneimine film has been investigated using square wave voltammetry. The electrode modification was achieved in order to separate the voltammetric peaks of ascorbic acid and uric acid when present in the same solution. On the modified electrodes the potential of the oxidation peak of the ascorbic acid was shifted to more negative values by over 0.3 V, while in the case of uric acid, the negative potential shift was about 0.15 V compared to the bare glassy carbon electrode. When the two compounds were found together in the solution, on the bare electrode only a single broad signal was observed, while on the modified electrode the peak potentials of these two compounds were separated by 0.4 V. When the uric acid concentration remained constant, the peak intensity of the ascorbic acid is increased linearly with the concentration (r2 = 0.996) and when the ascorbic acid concentration remains constant, the peak intensity of the uric acid increased linearly with the concentration (r2 = 0.992). FTIR measurements supported the formation of inclusion complexes. In order to characterize the modification of the electrodes microscopic studies were performed. The modified electrodes were successfully employed for the determination of ascorbic acid in pharmaceutical formulations with a detection limit of 0.22 μM. PMID:24287544

  7. Water soluble biocompatible vesicles based on polysaccharides and oligosaccharides inclusion complexes for carotenoid delivery.

    PubMed

    Polyakov, Nikolay E; Kispert, Lowell D

    2015-09-05

    Since carotenoids are highly hydrophobic, air- and light-sensitive hydrocarbon compounds, developing methods for increasing their bioavailability and stability towards irradiation and reactive oxygen species is an important goal. Application of inclusion complexes of "host-guest" type with polysaccharides and oligosaccharides such as arabinogalactan, cyclodextrins and glycyrrhizin minimizes the disadvantages of carotenoids when these compounds are used in food processing (colors and antioxidant capacity) as well as for production of therapeutic formulations. Cyclodextrin complexes which have been used demonstrated enhanced storage stability but suffered from poor solubility. Polysaccharide and oligosaccharide based inclusion complexes play an important role in pharmacology by providing increased solubility and stability of lipophilic drugs. In addition they are used as drug delivery systems to increase absorption rate and bioavailability of the drugs. In this review we summarize the existing data on preparation methods, analysis, and chemical reactivity of carotenoids in inclusion complexes with cyclodextrin, arabinogalactan and glycyrrhizin. It was demonstrated that incorporation of carotenoids into the "host" macromolecule results in significant changes in their physical and chemical properties. In particular, polysaccharide complexes show enhanced photostability of carotenoids in water solutions. A significant decrease in the reactivity towards metal ions and reactive oxygen species in solution was also detected. Copyright © 2015 Elsevier Ltd. All rights reserved.

  8. Cyclodextrins as excipients in tablet formulations.

    PubMed

    Conceição, Jaime; Adeoye, Oluwatomide; Cabral-Marques, Helena Maria; Lobo, José Manuel Sousa

    2018-04-22

    This paper aims to provide a critical review of cyclodextrins as excipients in tablet formulations, highlighting: (i) the principal pharmaceutical applications of cyclodextrins; (ii) the most relevant technological aspects in pharmaceutical formulation development; and (iii) the actual regulatory status of cyclodextrins. Moreover, several illustrative examples are presented. Cyclodextrins can be used as complexing excipients in tablet formulations for low-dose drugs. By contrast, for medium-dose drugs and/or when the complexation efficiency is low, the methods to enhance the complexation efficiency play a key part in reducing the cyclodextrin quantity. In addition, these compounds are used as fillers, disintegrants, binders and multifunctional direct compression excipients of the tablets. Copyright © 2018 Elsevier Ltd. All rights reserved.

  9. Preparation, physicochemical characterization and release behavior of the inclusion complex of trans-anethole and β-cyclodextrin.

    PubMed

    Zhang, Wenwen; Li, Xinying; Yu, Taocheng; Yuan, Lun; Rao, Gang; Li, Defu; Mu, Changdao

    2015-08-01

    Trans-anethole (AT) has a variety of antimicrobial properties and is widely used as food functional ingredient. However, the applications of AT are limited due to its low water solubility, strong odor and low physicochemical stability. Therefore, the aim of this work was to encapsulate AT with β-cyclodextrin (β-CD) for obtaining inclusion complex by co-precipitation method. The measurements effectively confirmed the formation of inclusion complex between AT and β-CD. The results showed that the inclusion complex presented new solid crystalline phases and was more thermally stable than the physical mixture and β-CD. The phase solubility study showed that the aqueous solubility of AT was increased by being included in β-CD. The calculated stability constant of inclusion complex was 1195M -1 , indicating the strong interaction between AT and β-CD. Furthermore, the release study suggested that β-CD provided the protection for AT against evaporation. The release behavior of AT from the inclusion complex was controlled. Copyright © 2015 Elsevier Ltd. All rights reserved.

  10. Nano-Assemblies of Modified Cyclodextrins and Their Complexes with Guest Molecules: Incorporation in Nanostructured Membranes and Amphiphile Nanoarchitectonics Design

    PubMed Central

    Zerkoune, Leïla; Angelova, Angelina; Lesieur, Sylviane

    2014-01-01

    A variety of cyclodextrin-based molecular structures, with substitutions of either primary or secondary faces of the natural oligosaccharide macrocycles of α-, β-, or γ-cyclodextrins, have been designed towards innovative applications of self-assembled cyclodextrin nanomaterials. Amphiphilic cyclodextrins have been obtained by chemical or enzymatic modifications of their macrocycles using phospholipidyl, peptidolipidyl, cholesteryl, and oligo(ethylene oxide) anchors as well as variable numbers of grafted hydrophobic hydrocarbon or fluorinated chains. These novel compounds may self-assemble in an aqueous medium into different types of supramolecular nanoassemblies (vesicles, micelles, nanorods, nanospheres, and other kinds of nanoparticles and liquid crystalline structures). This review discusses the supramolecular nanoarchitectures, which can be formed by amphiphilic cyclodextrin derivatives in mixtures with other molecules (phospholipids, surfactants, and olygonucleotides). Biomedical applications are foreseen for nanoencapsulation of drug molecules in the hydrophobic interchain volumes and nanocavities of the amphiphilic cyclodextrins (serving as drug carriers or pharmaceutical excipients), anticancer phototherapy, gene delivery, as well as for protection of instable active ingredients through inclusion complexation in nanostructured media. PMID:28344245

  11. The preparation, characterization, and pharmacokinetic studies of chitosan nanoparticles loaded with paclitaxel/dimethyl-β-cyclodextrin inclusion complexes

    PubMed Central

    Ye, Ya-Jing; Wang, Yun; Lou, Kai-Yan; Chen, Yan-Zuo; Chen, Rongjun; Gao, Feng

    2015-01-01

    A novel biocompatible and biodegradable drug-delivery nanoparticle (NP) has been developed to minimize the severe side effects of the poorly water-soluble anticancer drug paclitaxel (PTX) for clinical use. PTX was loaded into the hydrophobic cavity of a hydrophilic cyclodextrin derivative, heptakis (2,6-di-O-methyl)-β-cyclodextrin (DM-β-CD), using an aqueous solution-stirring method followed by lyophilization. The resulting PTX/DM-β-CD inclusion complex dramatically enhanced the solubility of PTX in water and was directly incorporated into chitosan (CS) to form NPs (with a size of 323.9–407.8 nm in diameter) using an ionic gelation method. The formed NPs had a zeta potential of +15.9–23.3 mV and showed high colloidal stability. With the same weight ratio of PTX to CS of 0.7, the loading efficiency of the PTX/DM-β-CD inclusion complex-loaded CS NPs was 30.3-fold higher than that of the PTX-loaded CS NPs. Moreover, it is notable that PTX was released from the DM-β-CD/CS NPs in a sustained-release manner. The pharmacokinetic studies revealed that, compared with reference formulation (Taxol®), the PTX/DM-β-CD inclusion complex-loaded CS NPs exhibited a significant increase in AUC0→24h (the area under the plasma drug concentration–time curve over the period of 24 hours) and mean residence time by 2.7-fold and 1.4-fold, respectively. Therefore, the novel drug/DM-β-CD inclusion complex-loaded CS NPs have promising applications for the significantly improved delivery and controlled release of the poorly water-soluble drug PTX or its derivatives, thus possibly leading to enhanced therapeutic efficacy and less severe side effects. PMID:26170666

  12. Host-guest interaction between pinocembrin and cyclodextrins: Characterization, solubilization and stability

    NASA Astrophysics Data System (ADS)

    Zhou, Shu-Ya; Ma, Shui-Xian; Cheng, Hui-Lin; Yang, Li-Juan; Chen, Wen; Yin, Yan-Qing; Shi, Yi-Min; Yang, Xiao-Dong

    2014-01-01

    The inclusion complexation behavior, characterization and binding ability of pinocembrin with β-cyclodextrin (β-CD) and its derivative 2-hydroxypropyl-β-cyclodextrin (HPβCD) were investigated in both solution and the solid state by means of XRD, DSC, 1H and 2D NMR and UV-vis spectroscopy. The results showed that the water solubility and thermal stability of pinocembrin were obviously increased in the inclusion complex with cyclodextrins. This satisfactory water solubility and high stability of the pinocembrin/CD complexes will be potentially useful for their application as herbal medicines or healthcare products.

  13. Hydroxypropyl-β-cyclodextrin for Delivery of Baicalin via Inclusion Complexation by Supercritical Fluid Encapsulation.

    PubMed

    Li, Ying; He, Zhen-Dan; Zheng, Qian-En; Hu, Chengshen; Lai, Wing-Fu

    2018-05-14

    Over the years, various methods have been developed to enhance the solubility of insoluble drugs; however, most of these methods are time-consuming and labor intensive or involve the use of toxic materials. A method that can safely and effectively enhance the solubility of insoluble drugs is lacking. This study adopted baicalin as an insoluble drug model, and used hydroxypropyl-β-cyclodextrin for the delivery of baicalin via the inclusion complexation by supercritical fluid encapsulation. Different parameters for the complex preparation as well as the physicochemical properties of the complex have been investigated. Our results showed that when compared to the conventional solution mixing approach, supercritical fluid encapsulation enables a more precise control of the properties of the complex, and gives higher loading and encapsulation efficiency. It is anticipated that our reported method can be useful in enhancing the preparation efficiency of inclusion complexes, and can expand the application potential of insoluble herbal ingredients in treatment development and pharmaceutical formulation.

  14. Cyclodextrin controlled release of poorly water-soluble drugs from hydrogels.

    PubMed

    Woldum, Henriette Sie; Larsen, Kim Lambertsen; Madsen, Flemming

    2008-01-01

    The effect of 2-hydroxypropyl-beta-cyclodextrin and gamma-cyclodextrin on the release of ibuprofen, ketoprofen and prednisolone was studied. Stability constants calculated for inclusion complexes show size dependence for complexes with both cyclodextrins. Hydrogels were prepared by ultraviolet irradiation and release of each model drug was studied. For drugs formulated using cyclodextrins an increase in the achievable concentration and in the release from hydrogels was obtained due to increased solubility, although the solubility of all gamma-cyclodextrin complexes was limited. The load also was increased by adjusting pH for the acidic drugs and this exceeds the increase obtained with gamma-cyclodextrin addition.

  15. Electrochemical and surface plasmon resonance characterization of β-cyclodextrin-based self-assembled monolayers and evaluation of their inclusion complexes with glucocorticoids

    NASA Astrophysics Data System (ADS)

    Frasconi, Marco; Mazzei, Franco

    2009-07-01

    This paper describes the characterization of a self-assembled β-cyclodextrin (β-CD)-derivative monolayer (β-CD-SAM) on a gold surface and the study of their inclusion complexes with glucocorticoids. To this aim the arrangement of a self-assembled β-cyclodextrin-derivative monolayer on a gold surface was monitored in situ by means of surface plasmon resonance (SPR) spectroscopy and double-layer capacitance measurements. Film thickness and dielectric constant were evaluated for a monolayer of β-CD using one-color-approach SPR. The selectivity of the β-CD host surface was verified by using electroactive species permeable and impermeable in the β-CD cavity. The redox probe was selected according to its capacity to permeate the β-CD monolayer and its electrochemical behavior. In order to evaluate the feasibility of an inclusion complex between β-CD-SAM with some steroids such as cortisol and cortisone, voltammetric experiments in the presence of the redox probes as molecules competitive with the steroids have been performed. The formation constant of the surface host-guest by β-CD-SAM and the steroids under study was calculated.

  16. Theoretical study of β- and γ-cyclodextrin complexes with ferrocene-containing azoles

    NASA Astrophysics Data System (ADS)

    Kiselev, S. S.; Snegur, L. V.; Simenel, A. A.; Davankov, V. A.; Il'in, M. M.; Borisov, Yu. A.

    2017-12-01

    The interaction between cyclodextrins (β- and γ-CD) and ferrocenyl azoles (i.e., pyrazole ferrocenes (I, III-V) and benzimidazole ferrocenes (VI, VII)), along with 1-ferrocenylethanol (II), each in the form of (R)- and (S)-enantiomers, in forming inclusion complexes is studied for the first time using detailed quantum chemical calculations. Compounds are calculated in terms of the density functional theory (DFT), using the Becke-Lee-Yang-Parr (B3LYP) approach in the 6-31G* basis sets. For the considered CD complexes with enantiomers of I-VII, structures in which a guest partially enters a host cavity from the side of the heterocyclic substituent (pyrazole or benzimidazole) are found to be energetically advantageous. It is shown that for successful resolution of (R,S)-enantiomers on chiral phases containing cyclodextrins, we must consider the interaction between outer hydroxyl groups on the CD cone's surface, in addition to the correspondence of geometric dimensions. The calculated data correlate well with the data from the chromatographic separation of guest enantiomers on cyclodextrin sorbents.

  17. The influence of dissolved H2O content in supercritical carbon dioxide to the inclusion complexes formation of ketoprofen/β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Goenawan, Joshua; Trisanti, P. N.; Sumarno

    2015-12-01

    This work studies the relation between dissolved H2O content in supercritical carbon dioxide (SC-CO2) with the formation of ketoprofen (KP)/β-cyclodextrin(CD) inclusion complexes. The process involves a physical mixture of these two compounds into contact with the supercritical carbon dioxide which had been previously saturated with H2O over a certain duration. The pressure used for saturation process is 130 bar and saturation temperature was ranged between 30 °C to 50 °C. The inclusion process was achieved by keeping it for 2 hours at 160 bar and 200 bar with inclusion temperature of 50 °C. The results enable us to suggest explanations for the inclusion formation. The inclusion complexes can be formed by contacting the dissolved H2O in SC-CO2 to the physical mixture of KP and CD. An increase in the temperature of saturation process resulted in an increase of dissolved H2O content in the supercritical carbon dioxide. The increasing levels of this water soluble resulted an increase in the inclusion complexes that has been formed. The formation of inclusion complexes includes the water molecules enhancing the emptying of the CD cavities and being replaced by KP, towards a more stable energy state. The drug release used for analyzing the dissolution rate of the KP/CD complexes. The results vary from 79,85% to 99,98% after 45 minutes which is above the rate that has been assigned by Farmakope Indonesia at 70% dissolution rate for KP. The use of SC-CO2 offers a new methods for increasing the rate of dissolution of drugs that are hydrophobic such as KP. CO2 used as a supercritical fluid because of its relatively low cost, easily obtainable supercritical conditions, and lack of toxicity. The material samples were characterized by DSC and Spectrophotometer UV-vis technique.

  18. Study to explore the mechanism to form inclusion complexes of β-cyclodextrin with vitamin molecules

    PubMed Central

    Saha, Subhadeep; Roy, Aditi; Roy, Kanak; Roy, Mahendra Nath

    2016-01-01

    Host–guest inclusion complexes of β-cyclodextrin with two vitamins viz., nicotinic acid and ascorbic acid in aqueous medium have been explored by reliable spectroscopic, physicochemical and calorimetric methods as stabilizer, carrier and regulatory releaser of the guest molecules. Job’s plots have been drawn by UV-visible spectroscopy to confirm the 1:1 stoichiometry of the host-guest assembly. Stereo-chemical nature of the inclusion complexes has been explained by 2D NMR spectroscopy. Surface tension and conductivity studies further support the inclusion process. Association constants for the vitamin-β-CD inclusion complexes have been calculated by UV-visible spectroscopy using both Benesi–Hildebrand method and non-linear programme, while the thermodynamic parameters have been estimated with the help of van’t Hoff equation. Isothermal titration calorimetric studies have been performed to determine the stoichiometry, association constant and thermodynamic parameters with high accuracy. The outcomes reveal that there is a drop in ΔSo, which is overcome by higher negative value of ΔHo, making the overall inclusion process thermodynamically favorable. The association constant is found to be higher for ascorbic acid than that for nicotinic acid, which has been explained on the basis of their molecular structures. PMID:27762346

  19. The interaction of caffeine with substituted cyclodextrins in water

    NASA Astrophysics Data System (ADS)

    Terekhova, I. V.; Kumeev, R. S.; Al'Per, G. A.

    2007-07-01

    The interaction of caffeine with hydroxypropyl-and methylcyclodextrins in water was studied by the calorimetry, spectroscopy, and solubility methods at 298.15 K. The interaction of caffeine with these cyclodextrins did not result in the formation of stable inclusion complexes and was mostly accompanied by predominantly endothermic effects of particle dehydration. The introduction of substituents and changes in the size of cyclodextrin molecular cavity did not influence the ability of cyclodextrins to form complexes with caffeine. The conclusion was drawn that substituted cyclodextrins could not be used for increasing the solubility of caffeine in water.

  20. Preparation, characterisation and antitumour activity of β-, γ- and HP-β-cyclodextrin inclusion complexes of oxaliplatin

    NASA Astrophysics Data System (ADS)

    Zhang, Da; Zhang, Jianqiang; Jiang, Kunming; Li, Ke; Cong, Yangwei; Pu, Shaoping; Jin, Yi; Lin, Jun

    2016-01-01

    Three water-soluble oxaliplatin complexes were prepared by inclusion complexation with β-cyclodextrin (β-CD), γ-CD and HP-β-CD. The structures of oxaliplatin/CDs were confirmed by NMR, FTIR, TGA, XRD as well as SEM analysis. The results show that the water solubility of oxaliplatin was increased in the complex with CDs in 1:1 stoichiometry inclusion modes, and the cyclohexane ring of oxaliplatin molecule was deeply inserted into the cavity of CDs. Moreover, the stoichiometry was established by a Job plot and the water stability constant (Kc) of oxaliplatin/CDs was calculated by phase solubility studies, all results show that the oxaliplatin/β-CD complex is more stable than free oxaliplatin, oxaliplatin/HP-β-CD and oxaliplatin/γ-CD. Meanwhile, the inclusion complexes displayed almost twice as high cytotoxicity compared to free oxaliplatin against HCT116 and MCF-7 cells. This satisfactory water solubility and higher cytotoxic activity of the oxaliplatin/CD complexes will potentially be useful for their application in anti-tumour therapy.

  1. Beta-cyclodextrin enhanced gastroprotective effect of (-)-linalool, a monoterpene present in rosewood essential oil, in gastric lesion models.

    PubMed

    da Silva, Francilene Vieira; de Barros Fernandes, Hélio; Oliveira, Irisdalva Sousa; Viana, Ana Flávia Seraine Custódio; da Costa, Douglas Soares; Lopes, Miriam Teresa Paz; de Lira, Kamila Lopes; Quintans-Júnior, Lucindo José; de Sousa, Adriano Antunes; de Cássia Meneses Oliveira, Rita

    2016-11-01

    (-)-Linalool is a monoterpene constituent of many essential oils. This particular monoterpene has both anti-inflammatory and antimicrobial activity. Moreover, this compound has been shown to be antinociceptive. However, the poor chemical stability and short half-life prevents the clinical application of (-)-linalool and many other essential oils. Important to the topic of this study, β-cyclodextrin (β-CD) has been used to increase the solubility, stability, and pharmacological effects of numerous lipophilic compounds in vivo. In this study, the gastroprotective activities of (-)-linalool (LIN) and linalool incorporated into inclusion complex containing β-cyclodextrin (LIN-βCD) were evaluated using models of acute and chronic gastric ulcers in rodents. LIN and LIN-βCD showed strong gastroprotective activity (p < 0.001). The LIN-βCD complex revealed that the gastroprotective effect was significantly improved compared with LIN uncomplexed, suggesting that this improvement is related to increased solubility and stability. Taking together the potentiation of the antioxidant profile of this monoterpene, our results suggest that β-CD may represent an important tool for improved gastroprotective activity of (-)-linalool and other water-insoluble compounds.

  2. Recovery and purification of cholesterol from cholesterol-β-cyclodextrin inclusion complex using ultrasound-assisted extraction.

    PubMed

    Li, Yong; Chen, Youliang; Li, Hua

    2017-01-01

    Response surface methodology was used to optimize ultrasound-assisted ethanol extraction (UAE) of cholesterol from cholesterol-β-cyclodextrin (C-β-CD) inclusion complex prepared from duck yolk oil. The best extraction conditions were solvent-solid ratio 10mL/g, ultrasonic power 251W, extraction temperature 56°C and sonication time 36min. Under these conditions, the highest cholesterol extraction yield and cholesterol content obtained 98.12±0.25% and 43.38±0.61mg/g inclusion complex, respectively. As compared with Reflux extraction and Soxhlet extraction, the UAE was more efficient and economical. To increase the purity of crude cholesterol extraction, silica gel column chromatography and crystallization were carried out. Finally, cholesterol was obtained at 95.1% purity, 71.7% recovery and 22.0% yield. Copyright © 2016 Elsevier B.V. All rights reserved.

  3. Fast-Dissolving, Prolonged Release, and Antibacterial Cyclodextrin/Limonene-Inclusion Complex Nanofibrous Webs via Polymer-Free Electrospinning.

    PubMed

    Aytac, Zeynep; Yildiz, Zehra Irem; Kayaci-Senirmak, Fatma; San Keskin, Nalan Oya; Kusku, Semran Ipek; Durgun, Engin; Tekinay, Turgay; Uyar, Tamer

    2016-10-05

    We have proposed a new strategy for preparing free-standing nanofibrous webs from an inclusion complex (IC) of a well-known flavor/fragrance compound (limonene) with three modified cyclodextrins (HPβCD, MβCD, and HPγCD) via electrospinning (CD/limonene-IC-NFs) without using a polymeric matrix. The experimental and computational modeling studies proved that the stoichiometry of the complexes was 1:1 for CD/limonene systems. MβCD/limonene-IC-NF released much more limonene at 37, 50, and 75 °C than HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF because of the greater amount of preserved limonene. Moreover, MβCD/limonene-IC-NF has released only 25% (w/w) of its limonene, whereas HPβCD/limonene-IC-NF and HPγCD/limonene-IC-NF released 51 and 88% (w/w) of their limonene in 100 days, respectively. CD/limonene-IC-NFs exhibited high antibacterial activity against E. coli and S. aureus. The water solubility of limonene increased significantly and CD/limonene-IC-NFs were dissolved in water in a few seconds. In brief, CD/limonene-IC-NFs with fast-dissolving character enhanced the thermal stability and prolonged the shelf life along with antibacterial properties could be quite applicable in food and oral care applications.

  4. Temperature effect on the vibrational dynamics of cyclodextrin inclusion complexes: investigation by FTIR-ATR spectroscopy and numerical simulation.

    PubMed

    Crupi, Vincenza; Majolino, Domenico; Venuti, Valentina; Guella, Graziano; Mancini, Ines; Rossi, Barbara; Verrocchio, Paolo; Viliani, Gabriele; Stancanelli, Rosanna

    2010-07-01

    The vibrational dynamics of solid inclusion complexes of the nonsteroidal anti-inflammatory drug Ibuprofen (IBP) with beta-cyclodextrin (beta-CD) and methyl-beta-cyclodextrin (Me-beta-CD) has been investigated by using attenuated total reflection-Fourier transform infrared FTIR-ATR spectroscopy, in order to monitor the changes induced, as a consequence of complexation, on the vibrational spectrum of IBP, in the wavenumber range 600-4000 cm(-1). Quantum chemical calculations were performed on monomeric and dimeric structures of IBP, derived from symmetric hydrogen bonding of the two carboxylic groups, in order to unambiguously assign some characteristic IR bands in the IBP spectrum. The evolution in temperature from 250 to 340 K of the C horizontal lineO stretching vibration, described by a best-fit procedure, allowed us to extract the thermodynamic parameter DeltaH associated to the binding of IBP with betaCDs in the solid phase. By comparing these results, Me-beta-CD has been shown to be the most effective carrier for IBP.

  5. Development of Orodispersible Tablets of Candesartan Cilexetil-β-cyclodextrin Complex

    PubMed Central

    Sravya, Maddukuri; Deveswaran, Rajamanickam; Bharath, Srinivasan; Basavaraj, Basappa Veerbadraiah; Madhavan, Varadharajan

    2013-01-01

    The aim of this study was to investigate the use of inclusion complexation technique employing β-cyclodextrin in improving the dissolution profile of candesartan cilexetil, a BCS class-II drug, and to formulate the inclusion complex into orodispersible tablets. The inclusion complexes were formed by physical mixing, kneading, coevaporation, and lyophilisation methods. Inclusion complexes were characterized by FTIR, DSC, XRD, NMR, and mass spectral studies. Inclusion complexes prepared using kneading, and lyophilisation techniques in the molar ratio 1 : 5 with β-cyclodextrin were used for formulating orodispersible tablets by direct compression with different superdisintegrants like croscarmellose sodium, crospovidone, sodium starch glycolate, and low substituted hydroxypropyl cellulose in varying concentrations. The directly compressible powder was evaluated for precompression parameters, and the prepared orodispersible tablets were evaluated for postcompression parameters. Drug-excipient compatibility studies showed no interaction, and characterization proved the formation of inclusion complex. In vitro disintegration time was found to be within 3 minutes, and all the formulations showed complete drug release of 100% within 20 minutes. The optimized formulation was found to be stable after 6 months and showed no significant change in drug content. This work proved β-cyclodextrins to be effective solubilizing agent in improving the solubility of poorly water soluble drugs. PMID:26555987

  6. Effect of γ-Cyclodextrin Inclusion Complex on the Absorption of R-α-Lipoic Acid in Rats

    PubMed Central

    Uchida, Ryota; Iwamoto, Kosuke; Nagayama, Suetada; Miyajima, Atsushi; Okamoto, Hinako; Ikuta, Naoko; Fukumi, Hiroshi; Terao, Keiji; Hirota, Takashi

    2015-01-01

    R-α-lipoic acid (RLA) is an endogenous organic acid, and works as a cofactor for mitochondrial enzymes and as a kind of antioxidant. Inclusion complexes of RLA with α-, β- or γ-cyclodextrins (CD) were prepared and orally administered as a suspension to rats. Among them, RLA/γ-CD showed the highest plasma exposure, and its area under the plasma concentration-time curve (AUC) of RLA was 2.2 times higher than that after oral administration of non-inclusion RLA. On the other hand, the AUC after oral administration of non-inclusion RLA and RLA/γ-CD to pylorus-ligated rats did not differ. However, the AUC after intraduodenal administration of RLA/γ-CD was 5.1 times higher than that of non-inclusion RLA, and was almost comparable to the AUC after intraduodenal administration of RLA-Na solution. Furthermore, the AUC after intraduodenal administration of RLA/γ-CD was not affected by biliary ligation or co-administration of an amylase inhibitor. These findings demonstrated that RLA was absorbed from the small intestine effectively when orally administered as a γ-CD inclusion complex, which could be easily dissolved in the lumen of the intestine. In conclusion, γ-CD inclusion complex is an appropriate formulation for supplying RLA as a drug or nutritional supplement with respect to absorption. PMID:25946345

  7. Interaction Mode between Inclusion Complex of Vitamin K3 with γ- Cyclodextrin and Herring-Sperm DNA.

    PubMed

    Tang, Yan; Cai, Li; Xue, Kang; Wang, Chunling; Xiong, Xiaoli

    2016-05-03

    Methods including spectroscopy, electronic chemistry and thermodynamics were used to study the inclusion effect between γ-cyclodextrin (CD) and vitamin K3(K3), as well as the interaction mode between herring-sperm DNA (hsDNA) and γ-CD-K3 inclusion complex. The results from ultraviolet spectroscopic method indicated that VK3 and γ-CD formed 1:1 inclusion complex, with the inclusion constant Kf = 1.02 × 10(4) L/mol, which is based on Benesi-Hildebrand's viewpoint. The outcomes from the probe method and Scatchard methods suggested that the interaction mode between γ-CD-K3 and DNA was a mixture mode, which included intercalation and electrostatic binding effects. The binding constants were K (θ)25°C = 2.16 × 10(4) L/mol, and K(θ)37°C = 1.06 × 10(4) L/mol. The thermodynamic functions of the interaction between γ-CD-K3 and DNA were ΔrHm(θ) = -2.74 × 10(4) J/mol, ΔrSm(θ) = 174.74 J·mol(-1)K(-1), therefore, both ΔrHm(θ) (enthalpy) and ΔrSm(θ) (entropy) worked as driven forces in this action.

  8. Amphiphilic Cyclodextrin Derivatives for Targeted Drug Delivery to Tumors.

    PubMed

    Erdogar, Nazlı; Varan, Gamze; Bilensoy, Erem

    2017-01-01

    Villiers has extensively studied cyclodextrins, a family of macrocyclic oligosaccharides linked by α-1,4 glycosidic bonds, in different fields since their discovery in 1891. The unique structure enabling inclusion complexation for natural cyclodextrins and cyclodextrin derivatives make them attractive for novel drug delivery systems. Cyclodextrins can be modified with long aliphatic chains to render an amphiphilic property and these different amphiphilic cyclodextrins are able to form nanoparticles without surfactants. In the literature, several different amphiphilic cyclodextrins are reported and applied to drug delivery and targeting especially to tumors. Specificly, folateconjugated amphiphilic cyclodextrin derivatives are used for active tumor targeting of poorly water soluble drugs and improve the efficacy and safety of therapeutic agents. On the other hand, effect of positive surface charge has also been under research in the recent years. Polycationic amphiphilic cyclodextrins have shown promise towards forming small complexes with negatively charged molecules such as drugs or plasmid DNA. Polycationic amphiphilic cyclodextrins enhance interaction with cell membrane due to their net positive surface charge. The scope of this review is to describe potential uses and pharmaceutical applications of tumor-targeted amphiphilic cyclodextrins, with focus on folate-conjugated cyclodextrin derivatives and polycationic cyclodextrin derivatives both studied by our group at Hacettepe University. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  9. Composite material of DNA and cyclodextrin-immobilized poly(ethyleneimine): Accumulation of harmful compounds from multi-component solution.

    PubMed

    Yamada, Masanori; Hori, Minako; Tabuchi, Shinya

    2010-08-01

    Water-soluble beta-cyclodextrin-immobilized poly(ethyleneimine) (PEICD) was synthesized by the grafting of beta-cyclodextrin to the branched poly(ethyleneimine). In an aqueous solution, this PEICD polymer could encapsulate bisphenol A, known to be a harmful compound. Additionally, the stability constant of bisphenol A to the PEICD polymer was 1.1 x 10(4)M(-1). However, the water-solubility of PEICD has been making it difficult to utilize it as an environmental material. Therefore, we prepared the DNA-PEICD composite material by mixing the double-stranded DNA and PEICD. This DNA-PEICD composite material was extremely stable in water and possessed both properties of the intercalation into the double-stranded DNA and the encapsulation into the CD cavity. As a result, this material can accumulate various harmful compounds, such as dioxin- and polychlorobiphenyl (PCB)-derivatives and bisphenol A, from a multi-component solution. Therefore, the DNA-PEICD composite material may have the potential to be used as an environmental material. Copyright 2010 Elsevier B.V. All rights reserved.

  10. Effect of cyclodextrin complexation on the aqueous solubility and solubility/dose ratio of praziquantel.

    PubMed

    Maragos, Stratos; Archontaki, Helen; Macheras, Panos; Valsami, Georgia

    2009-01-01

    Praziquantel (PZQ), the primary drug of choice in the treatment of schistosomiasis, is a highly lipophilic drug that possesses high permeability and low aqueous solubility and is, therefore, classified as a Class II drug according to the Biopharmaceutics Classification System (BCS). In this work, beta-cyclodextrin (beta-CD) and hydroxypropyl-beta-cyclodextrin (HP-beta-CD) were used in order to determine whether increasing the aqueous solubility of a drug by complexation with CDs, a BCS-Class II compound like PZQ could behave as BCS-Class I (highly soluble/highly permeable) drug. Phase solubility and the kneading and lyophilization techniques were used for inclusion complex preparation; solubility was determined by UV spectroscopy. The ability of the water soluble polymer polyvinylpyrolidone (PVP) to increase the complexation and solubilization efficiency of beta-CD and HP-beta-CD for PZQ was examined. Results showed significant improvement of PZQ solubility in the presence of both cyclodextrins but no additional effect in the presence of PVP. The solubility/dose ratios values of PZQ-cyclodextrin complexes calculated considering the low (150 mg) and the high dose (600 mg) of PZQ, used in practice, indicate that PZQ complexation with CDs may result in drug dosage forms that would behave as a BCS-Class I depending on the administered dose.

  11. A water-soluble, mucoadhesive quaternary ammonium chitosan-methyl-β-cyclodextrin conjugate forming inclusion complexes with dexamethasone.

    PubMed

    Piras, Anna Maria; Zambito, Ylenia; Burgalassi, Susi; Monti, Daniela; Tampucci, Silvia; Terreni, Eleonora; Fabiano, Angela; Balzano, Federica; Uccello-Barretta, Gloria; Chetoni, Patrizia

    2018-03-30

    The ocular bioavailability of lipophilic drugs, such as dexamethasone, depends on both drug water solubility and mucoadhesion/permeation. Cyclodextrins and chitosan are frequently employed to either improve drug solubility or prolong drug contact onto mucosae, respectively. Although the covalent conjugation of cyclodextrin and chitosan brings to mucoadhesive drug complexes, their water solubility is restricted to acidic pHs. This paper describes a straightforward grafting of methyl-β-cyclodextrin (MCD) on quaternary ammonium chitosan (QA-Ch60), mediated by hexamethylene diisocyanate. The resulting product is a water-soluble chitosan derivative, having a 10-atom long spacer between the quaternized chitosan and the cyclodextrin. The derivative is capable of complexing the model drug dexamethasone and stable complexes were also observed for the lyophilized products. Furthermore, the conjugate preserves the mucoadhesive properties typical of quaternized chitosan and its safety as solubilizing excipient for ophthalmic applications was preliminary assessed by in vitro cytotoxicity evaluations. Taken as a whole, the observed features appear promising for future processing of the developed product into 3D solid forms, such as controlled drug delivery systems, films or drug eluting medical devices.

  12. Spectral characteristics of tramadol in different solvents and β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Anton Smith, A.; Manavalan, R.; Kannan, K.; Rajendiran, N.

    2009-10-01

    Effect of solvents and β-cyclodextrin on the absorption and fluorescence spectra of tramadol drug has been investigated and compared with anisole. The solid inclusion complex of tramadol with β-CD is investigated by FT-IR, 1H NMR, scanning electron microscope (SEM), DSC and semiempirical methods. The thermodynamic parameter (Δ G) of inclusion process is determined. A solvent study shows (i) the spectral behaviour of both tramadol and anisole molecules is similar to each other and (ii) the cyclohexanol group in tramadol is not effectively conjugated with anisole group. However, in β-CD, due to space restriction of the CD cavity, a weak interaction is present between the above groups in tramadol. β-Cyclodextrin studies show that tramadol forms 1:2 inclusion complex with β-CD. A mechanism is proposed for the inclusion process.

  13. Effect of the chiral discrimination on the vibrational properties of (R)-, (S)- and (R, S)-ibuprofen/methyl-β-cyclodextrin inclusion complexes

    NASA Astrophysics Data System (ADS)

    Crupi, V.; Guella, G.; Majolino, D.; Mancini, I.; Paciaroni, A.; Rossi, B.; Venuti, V.; Verrocchio, P.; Viliani, G.

    2011-05-01

    The effects of chiral discrimination of ibuprofen (IBP) on the complexation process with methyl-β-cyclodextrin (Me-β-CD) were investigated in the solid phase by FTIR-ATR spectroscopy and numerical simulation. The inclusion mechanism was deduced from the temperature-dependent analysis of the vibrational spectra, in the C=O stretching region, of complexes formed by Me-β-CD with the two enantiomeric and the racemic forms of IBP. The mechanism turned out to be enthalpy-driven, with IBP enantiomers giving rise to more stable inclusion complexes with respect to the racemate.

  14. Biological activity of some derivatives of β-cyclodextrin.

    PubMed

    Batalova, T A; Dorovskich, V A; Kurochkina, G I; Grachev, M K; Plastinin, M L; Sergievich, A A

    2011-10-01

    New compounds of β-cyclodextrin containing covalently bound (conjugated) residues of acetylsalicylic and 1-(4-isobutylphenyl)-propionic acids were synthesized in the reaction of chlorides of the corresponding acids with β-cyclodextrin. We studied antiplatelet and antiphlogistic properties of these substances. It was shown that new compounds are comparable and in some cases are superior to the reference drugs acetylsalicylic acid and ibuprofen by anti-inflammatory and antiaggregant activities.

  15. Host-guest complexes of 2-hydroxypropyl-β-cyclodextrin/β-cyclodextrin and nifedipine: 1H NMR, molecular modeling, and dissolution studies

    NASA Astrophysics Data System (ADS)

    de Araújo, Márcia Valéria Gaspar; Vieira, João Victor Francisco; da Silva, Caroline W. P.; Barison, Andersson; Andrade, George Ricardo Santana; da Costa, Nivan Bezerra; Barboza, Fernanda Malaquias; Nadal, Jessica Mendes; Novatski, Andressa; Farago, Paulo Vitor; Zawadzki, Sônia Faria

    2017-12-01

    Nifedipine (NIF) is a hydrophobic drug widely used for treating cardiovascular diseases. This calcium channel blocker can present a higher apparent solubility by its inclusion into different cyclodextrins (CDs) as host-guest complexes. This paper focused on the structural investigation and dissolution behavior of inclusion complexes prepared with 2-hydroxypropyl-β-cyclodextrin (HPβCD) or β-cyclodextrin (βCD) and NIF. Drug amorphization was observed for HPβCD/NIF and βCD/NIF inclusion complexes by X-ray diffractometry (XRD). The sharp endothermic peak of NIF was not observed for these both host-guest complexes by differential scanning calorimetry (DSC). These results of XRD and DSC provide evidences of complexation between drug and the investigated CDs. 1H and saturation transfer difference nuclear magnetic resonance studies revealed the enhancement in the signal at 2.27 ppm for HPβCD/NIF and βCD/NIF inclusion complexes that corresponded to the methyl groups of NIF from the non-aromatic ring. This result suggested that non-aromatic ring of NIF was inserted into HPβCD and βCD cavities. Considering the mathematical simulations, it was observed that the inclusion process can occur in the both NH-in or NH-out forms. However, since it was used aqueous medium, it is possible to indicate that the obtained host-guest complexes HPβCD/NIF and βCD/NIF are in NH-in form which corresponded to the previous results obtained by 1H NMR experiments. Dissolution assays demonstrated that NIF inclusion complexes improved the drug release nevertheless without changing its biexponential release behavior. These host-guest complexes can be further used as feasible NIF carriers in solid dosage forms.

  16. A diffuse reflectance comparative study of benzil inclusion within microcrystalline cellulose and beta-cyclodextrin.

    PubMed

    Vieira Ferreira, Luis F; Ferreira Machado, Isabel; Da Silva, José P; Oliveira, Anabela S

    2004-02-01

    Diffuse reflectance and laser-induced techniques were used to study photochemical and photophysical processes of benzil adsorbed on two solid powdered supports, microcrystalline cellulose and [small beta]-cyclodextrin. In both substrates, a distribution of ground-state benzil conformers exists, largely dominated by skew conformations where the carbonyl groups are twisted one to the other. Room temperature phosphorescence was observed in air-equilibrated samples in both cases. The decay times vary greatly and the largest lifetime was obtained for benzil/[small beta]-cyclodextrin, showing that this host's cavity accommodates benzil well, enhancing its room temperature phosphorescence. Triplet-triplet absorption of benzil entrapped in cellulose was detected and benzil ketyl radical formation also occurred. With benzil included into [small beta]-cyclodextrin, and following laser excitation, benzoyl radicals were detected on the millisecond timescale. Product analysis and identification of laser-irradiated benzil samples in the two hosts clearly showed that the main degradation photoproducts were benzoic acid and benzaldehyde. The main differences were a larger benzoic acid/benzaldehyde ratio in the case of cellulose and the formation of benzyl alcohol in this support.

  17. Comparative evaluation of polymeric and amphiphilic cyclodextrin nanoparticles for effective camptothecin delivery.

    PubMed

    Cirpanli, Yasemin; Bilensoy, Erem; Lale Doğan, A; Caliş, Sema

    2009-09-01

    Camptothecin (CPT) is a potent anticancer agent. The clinical application of CPT is restricted by poor water solubility and instability under physiological conditions. Solubilization and stabilization of CPT were realized through nanoparticulate systems of amphiphilic cyclodextrins, poly(lactide-co-glycolide) (PLGA) or poly-epsilon-caprolactone (PCL). Nanoparticles were prepared with nanoprecipitation technique, whereas cyclodextrin nanoparticles were prepared from preformed inclusion complexes of CPT with amphiphilic cyclodextrins. Polymeric nanoparticles, on the other hand, were loaded with CPT:HP-beta-CD inclusion complex to solubilize and stabilize the drug. Mean particle sizes were under 275 nm, and polydispersity indices were lower than 0.2 for all formulations. Drug-loading values were significantly higher for amphiphilic cyclodextrin nanoparticles when compared with those for PLGA and PCL nanoparticles. Nanoparticle formulations showed a significant controlled release profile extended up to 12 days for amphiphilic cyclodextrin nanoparticles and 48h for polymeric nanoparticles. Anticancer efficacy of the nanoparticles was evaluated in comparison with CPT solution in dimethyl sulfoxide (DMSO) on MCF-7 breast adenocarcinoma cells. Amphiphilic cyclodextrin nanoparticles showed higher anticancer efficacy than PLGA or PCL nanoparticles loaded with CPT and the CPT solution in DMSO. These results indicated that CPT-loaded amphiphilic cyclodextrin nanoparticles might provide a promising carrier system for the effective delivery of this anticancer drug having bioavailability problems.

  18. Phase solubility, 1H NMR and molecular modelling studies of bupivacaine hydrochloride complexation with different cyclodextrin derivates

    NASA Astrophysics Data System (ADS)

    Jug, Mario; Mennini, Natascia; Melani, Fabrizio; Maestrelli, Francesca; Mura, Paola

    2010-11-01

    A novel method, which simultaneously exploits experimental (NMR) and theoretically calculated data obtained by a molecular modelling technique, was proposed, to obtain deeper insight into inclusion geometry and possible stereoselective binding of bupivacaine hydrochloride with selected cyclodextrin derivatives. Sulphobuthylether-β-cyclodextrin and water soluble polymeric β-cyclodextrin demonstrated to be the best complexing agents for the drug, resulting in formation of the most stable inclusion complexes with the highest increase in aqueous drug solubility. The drug-carrier binding modes with these cyclodextrins and phenomena which may be directly related to the higher stability and better aqueous solubility of complexes formed were discussed in details.

  19. Cyclodextrin inclusion complex formation and solid-state characterization of the natural antioxidants alpha-tocopherol and quercetin.

    PubMed

    Koontz, John L; Marcy, Joseph E; O'Keefe, Sean F; Duncan, Susan E

    2009-02-25

    Cyclodextrin (CD) complexation procedures are relatively simple processes, but these techniques often require very specific conditions for each individual guest molecule. Variations of the coprecipitation from aqueous solution technique were optimized for the CD complexation of the natural antioxidants alpha-tocopherol and quercetin. Solid inclusion complex products of alpha-tocopherol/beta-CD and quercetin/gamma-CD had molar ratios of 1.7:1, which were equivalent to 18.1% (w/w) alpha-tocopherol and 13.0% (w/w) quercetin. The molar reactant ratios of CD/antioxidant were optimized at 8:1 to improve the yield of complexation. The product yields of alpha-tocopherol/beta-CD and quercetin/gamma-CD complexes from their individual reactants were calculated as 24 and 21% (w/w), respectively. ATR/FT-IR, 13C CP/MAS NMR, TGA, and DSC provided evidence of antioxidant interaction with CD at the molecular level, which indicated true CD inclusion complexation in the solid state. Natural antioxidant/CD inclusion complexes may serve as novel additives in controlled-release active packaging to extend the oxidative stability of foods.

  20. Crystallographic and theoretical studies of an inclusion complex of β-cyclodextrin with fentanyl.

    PubMed

    Ogawa, Noriko; Nagase, Hiromasa; Loftsson, Thorsteinn; Endo, Tomohiro; Takahashi, Chisato; Kawashima, Yoshiaki; Ueda, Haruhisa; Yamamoto, Hiromitsu

    2017-10-15

    The crystal structure of an inclusion complex of β-cyclodextrin (β-CD) with fentanyl was determined by single crystal X-ray diffraction analysis. The crystal belongs to the triclinic space group P1 and the complex comprises one fentanyl, two β-CD, and several water molecules. β-CD and fentanyl form a host-guest inclusion complex at a ratio of 2:1 and the asymmetric unit of the complex contains two host molecules (β-CDs) in a head-to-head arrangement that form dimers through hydrogen bonds between the secondary hydroxyl groups of β-CD and one guest molecule. Fentanyl is totally contained within the β-CD cavity and the structure of the phenylethyl part of fentanyl inside the dimeric cavity of the complex is disordered. Furthermore, theoretical molecular conformational calculations were conducted to clarify the mobility of the guest molecule in the β-CD cavity using CONFLEX software. Crystal optimization and crystal energy calculations were also conducted. The results of the theoretical calculations confirmed that the conformation of disorder part 1, which was high in occupancy by crystal structure analysis, was more stable. The phenylethyl part of fentanyl existed in several stable conformations. Copyright © 2017 Elsevier B.V. All rights reserved.

  1. Fluorometric and theoretical studies on inclusion complexes of β-cyclodextrin and D-, L-phenylalanine

    NASA Astrophysics Data System (ADS)

    Aree, Thammarat; Arunchai, Rungthiwa; Koonrugsa, Narongsak; Intasiri, Amarawan

    2012-10-01

    Inclusion complexes of β-cyclodextrin (β-CD) with L- and D-phenylalanine (Phe) have been characterized in solution by fluorometry and in gas phase by semiempirical PM3 calculations. The unimolar stoichiometric ratio of both β-CD-L-Phe and β-CD-D-Phe complexes and the stability constants (K) were deduced from fluorometric titrations. The β-CD-L-Phe complex is more stable than the β-CD-D-Phe complex as indicated by the larger K values, 21.1 vs. 6.86 M-1. This is consistent with the stabilization energies (ΔEstb) and inclusion geometries obtained from PM3 calculations. The β-CD-L-Phe complex with L-Phe residing in the central β-CD cavity and pointing its COOH group downwards to the O6 end has ΔEstb = -62.7 kJ mol-1, whereas the β-CD-D-Phe complex with D-Phe placing at 3 Å beneath the β-CD O4-plane and pointing its COOH group upwards to the O2/O3 end has ΔEstb = -53.3 kJ mol-1. The unison of host-guest intermolecular hydrogen bonds, hydrophobic interactions and molecular deformations plays an essential role in forming and stabilizing the inclusion complexes. Our results show that the β-CD-L-Phe and β-CD-D-Phe inclusion complexes are relatively stable and differentiable, suggesting the applications of CDs in foods and drugs.

  2. Ternary cyclodextrin polyurethanes containing phosphate groups: Synthesis and complexation of ciprofloxacin.

    PubMed

    Moreira, Mirna Pereira; Andrade, George Ricardo Santana; de Araujo, Marcia Valeria Gaspar; Kubota, Tatiana; Gimenez, Iara F

    2016-10-20

    Synthesis of ternary polyurethanes (PUs) from hexamethylenediisocyanate, β-cyclodextrin and β-glycerophosphate (acid and calcium salt) was studies varying synthesis parameters such as monomer proportion, heating method (reflux and microwave), and catalyst amount. Favorable conditions were provided by microwave irradiation and use of β-glycerophosphoric acid although the results suggest that it is possible to obtain ternary PUs with the calcium salt. FTIR data indicated the existence of secondary urea linkages. After characterization of ternary PUs by FTIR spectroscopy, XRD and thermal analysis, as well as evidences that the cyclodextrin cavities remained active toward inclusion of guest molecules, the possibility of inclusion of the antibiotic ciprofloxacin was evaluated. Absence of ciprofloxacin melting peak in DSC curves indicated that it is molecularly dispersed within the polymer, possibly included in the cyclodextrin. In vitro release experiments suggested additional non-inclusion interactions, showing also that the use of dialysis membranes may mask the actual release profile. Copyright © 2016. Published by Elsevier Ltd.

  3. Synthesis and characterization of nano-encapsulated black pepper oleoresin using hydroxypropyl beta-cyclodextrin for antioxidant and antimicrobial applications.

    PubMed

    Teixeira, Bruna N; Ozdemir, Necla; Hill, Laura E; Gomes, Carmen L

    2013-12-01

    Previous studies have reported antimicrobial and antioxidant activity of black pepper oleoresin which is associated to its phenolic compounds and piperine. The ability of cyclodextrins to form an inclusion complex with a guest molecule could improve black pepper oleoresin application, bioavailability, and stability in foods. Hydroxypropyl beta-cyclodextrin (HPBCD) inclusion complex with black pepper olereosin were synthesized using the kneading method and characterized for its physico-chemical properties and its antioxidant and antimicrobial activities. Inclusion complex size was 103.9 ± 7.6 nm and indicated to be a polydisperse system. The entrapment efficiency was 78.3 ± 3.6%, which suggests that other constituents in black pepper oleoresin have higher affinities for HPBCD than piperine (major compound in black pepper oleoresin). Thermograms showed the disappearance of oxidation peaks of black pepper oleoresin, proving complex formation with HPBCD. Phase solubility results indicated 1:1 stoichiometric inclusion complex formation and an increase of black pepper oleoresin aqueous solubility with HPBCD concentration. Nano-encapsulation with HPBCD did not affect (P > 0.05) total phenolic content; however, it enhanced (P < 0.05) black pepper oleoresin antioxidant activity. Black pepper oleoresin and its inclusion complex were analyzed for their antimicrobial activity against Escherichia coli K12 and Salmonella enterica serovar Typhimurium LT2. Both free and encapsulated black pepper oleoresin effectively inhibited bacterial growth within the concentration range tested. Black pepper oleoresin encapsulated in HPBCD was able to inhibit Salmonella at lower (P < 0.05) concentrations than its corresponding free extract. Therefore, black pepper oleoresin-HPBCD nanocapsules could have important applications in the food industry as antimicrobial and antioxidant system. © 2013 Institute of Food Technologists®

  4. Complexation of Statins with β-Cyclodextrin in Solutions of Small Molecular Additives and Macromolecular Colloids

    NASA Astrophysics Data System (ADS)

    Süle, András; Csempesz, Ferenc

    The solubility of lovastatin and simvastatin (inevitable drugs in the management of cardiovascular diseases) was studied by phase-solubility measurements in multicomponent colloidal and non-colloidal media. Complexation in aqueous solutions of the highly lipophilic statins with β-cyclodextrin (β-CD) in the absence and the presence of dissolved polyvinyl pyrrolidone, its monomeric compound, tartaric acid and urea, respectively, were investigated. For the characterization of the CD-statin inclusion complexes, stability constants for the associates have been calculated.

  5. Antifungal activity improved by coproduction of cyclodextrins and anabaenolysins in Cyanobacteria

    PubMed Central

    Shishido, Tania K.; Jokela, Jouni; Kolehmainen, Clara-Theresia; Fewer, David P.; Wahlsten, Matti; Wang, Hao; Rouhiainen, Leo; Rizzi, Ermanno; De Bellis, Gianluca; Permi, Perttu; Sivonen, Kaarina

    2015-01-01

    Cyclodextrins are cyclic oligosaccharides widely used in the pharmaceutical industry to improve drug delivery and to increase the solubility of hydrophobic compounds. Anabaenolysins are lipopeptides produced by cyanobacteria with potent lytic activity in cholesterol-containing membranes. Here, we identified the 23- to 24-kb gene clusters responsible for the production of the lipopeptide anabaenolysin. The hybrid nonribosomal peptide synthetase and polyketide synthase biosynthetic gene cluster is encoded in the genomes of three anabaenolysin-producing strains of Anabaena. We detected previously unidentified strains producing known anabaenolysins A and B and discovered the production of new variants of anabaenolysins C and D. Bioassays demonstrated that anabaenolysins have weak antifungal activity against Candida albicans. Surprisingly, addition of the hydrophilic fraction of the whole-cell extracts increased the antifungal activity of the hydrophobic anabaenolysins. The fraction contained compounds identified by NMR as α-, β-, and γ-cyclodextrins, which undergo acetylation. Cyclodextrins have been used for decades to improve the solubility and bioavailability of many drugs including antifungal compounds. This study shows a natural example of cyclodextrins improving the solubility and efficacy of an antifungal compound in an ancient lineage of photosynthetic bacteria. PMID:26474830

  6. Host-guest chemistry of cyclodextrin carbamates and cellulose derivatives in aqueous solution.

    PubMed

    Guo, Xin; Jia, Xiangxiang; Du, Jiaojiao; Xiao, Longqiang; Li, Feifei; Liao, Liqiong; Liu, Lijian

    2013-10-15

    Supramolecular polymer micelles were prepared on basis of the inclusion complexation between cyclodextrin carbamates and cellulose derivatives in aqueous media. Cyclodextrin carbamates were synthesized by microwave-assisted method from cyclodextrin and urea. The urea modified cyclodextrin shows the higher yield than the physical mixture of urea/cyclodextrin in the micellization with cellulose derivatives. The supramolecular structure of the core-shell micelles was demonstrated by (1)H NMR spectra, TEM images, and fluorescence spectra. The drug release behavior of the supramolecular polymer micelles was evaluated using prednisone acetate as a model drug. The drug loaded micelles showed steady and long time drug release behavior. With these properties, the supramolecular polymer micelles are attractive as drug carriers for pharmaceutical applications. Copyright © 2013 Elsevier Ltd. All rights reserved.

  7. Lanthanide-cyclodextrin complexes as probes for elucidating optical purity by NMR spectroscopy

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Wenzel, T.J.; Bogyo, M.S.; Lebeau, E.L.

    1994-06-01

    A multidentate ligand is bonded to cyclodextrins by the reaction of diethylenetriaminepentaacetic dianhydride with 6-mono- and 2-mono(ethylenediamine) derivatives of cyclodextrin. Adding Dy(III) to the cyclodextrin derivatives enhances the enantiomeric resolution in the [sup 1]H NMR spectra of carbionoxamine maleate, doxylamine succinate, pheniramine maleate, propranolol hydrochloride, and tryptophan. The enhancement is more pronounced with the secondary derivative. The Dy(III)-induced shifts can be used to elucidate the geometry of cyclodextrin-substrate inclusion complexes. Lanthanide-induced shifts are reported for complexes of aspartame, tryptophan, propranolol, and 1-anilino-8-naphthalenesulfonate with cyclodextrins, and the relative magnitudes of the shifts agree with previously reported structures of the complexes. 37more » refs., 9 figs., 5 tabs.« less

  8. Inclusion complexes of cypermethrin and permethrin with monochlorotriazinyl-beta-cyclodextrin: A combined spectroscopy, TG/DSC and DFT study

    NASA Astrophysics Data System (ADS)

    Yao, Qi; You, Bin; Zhou, Shuli; Chen, Meng; Wang, Yujiao; Li, Wei

    2014-01-01

    The suitable size hydrophobic cavity and monochlorotriazinyl group as a reactive anchor make MCT-β-CD to be widely used in fabric finishing. In this paper, the inclusion complexes of monochlorotriazinyl-beta-cyclodextrin (MCT-β-CD) with cypermethrin (CYPERM) and permethrin (PERM) are synthesized and analyzed by TG/DSC, FT-IR and Raman spectroscopy. TG/DSC reveals that the decomposed temperatures of inclusion complexes are lower by 25-30 °C than that of physical mixtures. DFT calculations in conjunction with FT-IR and Raman spectral analyses are used to study the structures of MCT-β-CD and their inclusion complexes. Four isomers of trisubstituted MCT-β-CD are designed and DFT calculations reveal that 1,3,5-trisubstituted MCT-β-CD has the lowest energy and can be considered as main component of MCT-β-CD. The ground-state geometries, vibrational wavenumbers, IR and Raman intensities of MCT-β-CD and their inclusion complexes were calculated at B3LYP/6-31G (d) level of theory. Upon examining the optimized geometry of inclusion complex, we find that the CYPERM and PERM are inserted into the toroid of MCT-β-CD from the larger opening. The band at 1646 cm-1 in IR and at 1668 cm-1 in Raman spectrum reveals that monochloroazinyl group of MCT-β-CD exists in ketone form but not in anion form. The noticeable IR and Raman shift of phenyl reveals that these two benzene rings of CYPERM and PERM stays inside the cavity of MCT-β-CD and has weak interaction with MCT-β-CD. This spectroscopy conclusion is consistent with theoretical predicted structure.

  9. Functionalized β-cyclodextrin based potentiometric sensor for naproxen determination.

    PubMed

    Lenik, Joanna; Łyszczek, Renata

    2016-04-01

    Potentiometric sensors based on neutral β-cyclodextrins: (2-hydroxypropyl)-β-cyclodextrin, heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, heptakis(2,3,6-tri-O-benzoyl)-β-cyclodextrin and anionic β-cyclodextrin: (2-hydroxy-3-N,N,N-trimethylamino)propyl-β-cyclodextrin chloride for naproxen are described. Inclusion complexes of naproxen with the above-mentioned cyclodextrins were studied using IR spectroscopy. The electrode surface was made from PVC membranes doped with the appropriate β-cyclodextrin as ionophores and quaternary ammonium chlorides as positive charge additives that were dispersed in plasticizers. The optimum membrane contains heptakis(2,3,6-tri-O-benzoyl)-β-cyclodextrin, o-nitrophenyloctyl ether and tetraoctyl ammonium chloride as a lipophilic salt. The electrode is characterized by a Nernstian response slope of -59.0 ± 0.5 mV decade(-1) over the linear range of 5.0 × 10(-5)-1.0 × 10(-2) mol L(-1) and the detection limit 1.0 × 10(-5) mol L(-1), as well as the response time 10s. It can be used in the pH range 6.2-8.5 for 10 months without any considerable deterioration. Incorporation of β-cyclodextrins improved the electrode selectivity towards naproxen ions from several inorganic and organic interferents and some common drug excipients due to concovalent interactions (host molecule-guest molecule). The notable advantages of the naproxen-selective electrode include its high sensitivity, high selectivity, cost-effectiveness as well as accurate and comfortable application in drug analysis and milk samples. Copyright © 2015. Published by Elsevier B.V.

  10. Cyclodextrin Nanoparticles Bearing 8-Hydroxyquinoline Ligands as Multifunctional Biomaterials.

    PubMed

    Oliveri, Valentina; Bellia, Francesco; Vecchio, Graziella

    2017-03-28

    Cyclodextrins are used as building blocks for the development of a host of polymeric biomaterials. The cyclodextrin polymers have found numerous applications as they exhibit unique features such as mechanical properties, stimuli responsiveness and drug loading ability. Notwithstanding the abundance of cyclodextrin polymers studied, metal-chelating polymers based on cyclodextrins have been poorly explored. Herein we report the synthesis and the characterization of the first metal-chelating β-cyclodextrin polymer bearing 8-hydroxyquinoline ligands. The metal ions (Cu 2+ or Zn 2+ ) can modulate the assembly of the polymer nanoparticles. Moreover, the protective activity of the new chelating polymer against self- and metal-induced Aβ aggregation and free radical species are significantly higher than those of the parent compounds. These synergistic effects suggest that the incorporation of hydroxyquinoline moieties into a soluble β-cyclodextrin polymer could represent a promising strategy to design multifunctional biomaterials. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  11. Redox-Active Carbohydrate-Coated Nanoparticles: Self-Assembly of a Cyclodextrin-Polystyrene Glycopolymer with Tetrazine-Naphthalimide.

    PubMed

    Gross, Andrew J; Haddad, Raoudha; Travelet, Christophe; Reynaud, Eric; Audebert, Pierre; Borsali, Redouane; Cosnier, Serge

    2016-11-15

    The controlled self-assembly of precise and well-defined photochemically and electrochemically active carbohydrate-coated nanoparticles offers the exciting prospect of biocompatible catalysts for energy storage/conversion and biolabeling applications. Here an aqueous nanoparticle system has been developed with a versatile outer layer for host-guest molecule encapsulation via β-cyclodextrin inclusion complexes. A β-cyclodextrin-modified polystyrene polymer was first obtained by copper nanopowder click chemistry. The glycopolymer enables self-assembly and controlled encapsulation of tetrazine-naphthalimide, as a model redox-active agent, into nanoparticles via nanoprecipitation. Cyclodextrin host-guest interactions permit encapsulation and internanoparticle cross-linking for the formation of fluorescent compound and clustered self-assemblies with chemically reversible electroactivity in aqueous solution. Light scattering experiments revealed stable particles with hydrodynamic diameters of 138 and 654 nm for nanoparticles prepared with tetrazine, of which 95% of the nanoparticles represent the smaller objects by number. Dynamic light scattering revealed differences as a function of preparation method in terms of size, 3-month stability, polydispersity, radius of gyration, and shape factor. Individual self-assemblies were visualized by atomic force microscopy and fluorescence microscopy and monitored in real-time by nanoparticle tracking analysis. UV-vis and fluorescence spectra provided insight into the optical properties and critical evidence for host-guest encapsulation as evidenced by solvachromatism and enhanced tetrazine uptake. Cyclic voltammetry was used to investigate the electrochemical properties and provided further support for encapsulation and an estimate of the tetrazine loading capacity in tandem with light scattering data.

  12. Controlled synthesis and inclusion ability of a hyaluronic acid derivative bearing beta-cyclodextrin molecules.

    PubMed

    Charlot, Aurélia; Heyraud, Alain; Guenot, Pierre; Rinaudo, Marguerite; Auzély-Velty, Rachel

    2006-03-01

    A new synthetic route to beta-cyclodextrin-linked hyaluronic acid (HA-CD) was developed. This was based on the preparation of a HA derivative selectively modified with adipic dihydrazide (HA-ADH) and a beta-cyclodextrin derivative possessing an aldehyde function on the primary face, followed by their coupling by a reductive amination-type reaction. The CD-polysaccharide was fully characterized in terms of chemical integrity and purity by high-resolution NMR spectroscopy. The complexation ability of the grafted CD was further demonstrated by isothermal titration calorimetry using sodium adamantane acetate (ADAc) and Ibuprofen as model guest molecules. The thermodynamic parameters for the complexation of these negatively charged guest molecules by the beta-CD grafted on negatively charged HA were shown to be largely influenced by the ionic strength of the aqueous medium.

  13. Solubility of (+/-)-ibuprofen and S (+)-ibuprofen in the presence of cosolvents and cyclodextrins.

    PubMed

    Nerurkar, Jayanti; Beach, J W; Park, M O; Jun, H W

    2005-01-01

    Aqueous solubility is an important parameter for the development of liquid formulations and in the determination of bioavailability of oral dosage forms. Ibuprofen (IB), a nonsteroidal anti-inflammatory drug, is a chiral molecule and is currently used clinically as a racemate (racIB). However, the S form of ibuprofen or S(+)-ibuprofen (SIB) is the biologically active isomer and is primarily responsible for the antiinflammatory activity. Phase solubility studies were carried out to compare the saturation solubilities of racIB and SIB in the presence of common pharmaceutical solvents such as glycerol, sorbitol solution, propylene glycol (PG), and polyethylene glycol (PEG 300) over the range of 20% to 80% v/v in aqueous based systems. The solubilities of the two compounds were also compared in the presence of cyclodextrins such as beta cyclodextrin (CD), hydroxypropyl beta cyclodextrin (HPCD), and beta cyclodextrin sulfobutyl ether sodium salt (CDSB) over the range of 5% to 25% w/v. Solubility determinations were carried at 25 degrees C and 37 degrees C. Cosolvents exponentially increased the solubility of both SIB and racIB, especially in the presence of PG and PEG 300. Glycerol was not very effective in increasing the aqueous solubilities of both compounds, whereas sorbitol solution had a minimal effect on their solubility. PG and PEG 300 increased the solubility of SIB by 400-fold and 1500-fold, respectively, whereas the rise in solubility for racIB was 193-fold and 700-fold, respectively, at 25 degrees C for the highest concentration of the cosolvents used (80% v/v). Of the two compounds studied, higher equilibrium solubilities were observed for SIB as compared with racIB. The derivatized cyclodextrins increased the aqueous solubility of racIB and SIB in a concentration-dependent manner giving AL type of phase diagrams. The phase solubility diagrams indicated the formation of soluble inclusion complexes between the drugs and HPCD and CDSB, which was of 1

  14. Preparation and structural characterization of corn starch-aroma compound inclusion complexes.

    PubMed

    Zhang, Shu; Zhou, Yibin; Jin, Shanshan; Meng, Xin; Yang, Liping; Wang, Haisong

    2017-01-01

    Six corn starch inclusion complexes were synthesized using small nonpolar or weak polar aroma compounds (heptanolide, carvone and menthone) and small polar aroma compounds (linalool, heptanol and menthol). The objectives of this study were to (a) investigate the ability of corn starch to form inclusion complexes with these aroma compounds and (b) characterize the structure of the corn starch inclusion complexes. The resulting inclusion ratios were 75.6, 36.9, 43.8, 91.9, 67.2 and 54.7% for heptanolide, carvone, menthone, linalool, heptanol and menthol respectively. The inclusion complexes had laminated structures with a certain amount of holes or blocky constructions. Compared with gelatinized corn starch, the transition temperatures, peak temperatures and enthalpies of the inclusion complexes were significantly different. The major peak of CO at 1771 cm -1 and significant peak shifts revealed the formation of inclusion complexes. X-ray diffractometry (XRD) analyses revealed that the crystallinity of corn starch-polar aroma compound inclusion complexes increased. Based on cross-polarization magic angle spinning 13 C nuclear magnetic resonance (CP-MAS 13 C NMR) results, novel peaks and chemical shifts were attributed to the presence of small aroma compounds, thereby confirming the formation of corn starch inclusion complexes. Small nonpolar and polar aroma compounds can be complexed to corn starch. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.

  15. Enhanced dissolution, stability and physicochemical characterization of ATRA/2-hydroxypropyl-β-cyclodextrin inclusion complex pellets prepared by fluid-bed coating technique.

    PubMed

    Chen, Zhongjian; Lu, Yi; Qi, Jianping; Wu, Wei

    2013-02-01

    The aim of this work was to prepare stable all-trans-retinoic acid (ATRA)/2-hydroxypropyl-β-cyclodextrin (HPCD) inclusion complex pellets with industrial feasible technology, the fluid-bed coating technique, using PVP K30 simultaneously as binder and reprecipitation retarder. The coating process was fluent with high coating efficiency. In vitro dissolution of the inclusion complex pellets in 5% w/v Cremopher EL solution was dramatically enhanced with no reprecipitation observed, and significantly improved stability against humidity (92.5% and 75% RH) and illumination (4500 lx ± 500 lx) was achieved by HPCD inclusion. Differential scanning calorimetry and powder X-ray diffractometry confirmed the absence of crystallinity of ATRA. Fourier transform-infrared spectrometry revealed interaction between ATRA and HPCD adding evidence on inclusion of ATRA moieties into HPCD cavities. Solid-state (13)C NMR spectrometry indicated possible inclusion of ATRA through the polyene chain, which was the main reason for the enhanced photostability. It is concluded that the fluid-bed coating technique has the potential use in the industrial preparation of ATRA/HPCD inclusion complex pellets.

  16. Enhancement of the release of azelaic acid through the synthetic membranes by inclusion complex formation with hydroxypropyl-beta-cyclodextrin.

    PubMed

    Manosroi, Jiradej; Apriyani, Maria Goretti; Foe, Kuncoro; Manosroi, Aranya

    2005-04-11

    The aim of this study was to investigate the release rates of azelaic acid and azelaic acid-hydroxypropyl-beta-cyclodextrin (HPbetaCD) inclusion complex through three types of synthetic membranes, namely cellophane, silicone and elastomer membranes. Solid inclusion complexes of azelaic acid-HPbetaCD at the molar ratio of 1:1 were prepared by coevaporation and freeze-drying methods, subsequently characterized by differential scanning calorimetry, X-ray diffractometry and dissolution studies. Solid inclusion complex obtained by coevaporation method which exhibited the inclusion of azelaic acid in the HPbetaCD cavity and gave the highest dissolution rate of azelaic acid was selected for the release study. Release studies of azelaic acid and this complex through the synthetic membranes were conducted using vertical Franz diffusion cells at 30 degrees C for 6 days. The release rates of azelaic acid through the synthetic membranes were enhanced by the formation of inclusion complex with HPbetaCD at the molar ratio of 1:1, with the increasing fluxes of about 41, 81 and 28 times of the uncomplexed system in cellophane, silicone and elastomer membranes, respectively. The result from this study can be applied for the development of azelaic acid for topical use.

  17. Studying anti-oxidative properties of inclusion complexes of α-lipoic acid with γ-cyclodextrin in single living fission yeast by confocal Raman microspectroscopy

    NASA Astrophysics Data System (ADS)

    Noothalapati, Hemanth; Ikarashi, Ryo; Iwasaki, Keita; Nishida, Tatsuro; Kaino, Tomohiro; Yoshikiyo, Keisuke; Terao, Keiji; Nakata, Daisuke; Ikuta, Naoko; Ando, Masahiro; Hamaguchi, Hiro-o.; Kawamukai, Makoto; Yamamoto, Tatsuyuki

    2018-05-01

    α-lipoic acid (ALA) is an essential cofactor for many enzyme complexes in aerobic metabolism, especially in mitochondria of eukaryotic cells where respiration takes place. It also has excellent anti-oxidative properties. The acid has two stereo-isomers, R- and S- lipoic acid (R-LA and S-LA), but only the R-LA has biological significance and is exclusively produced in our body. A mutant strain of fission yeast, Δdps1, cannot synthesize coenzyme Q10, which is essential during yeast respiration, leading to oxidative stress. Therefore, it shows growth delay in the minimal medium. We studied anti-oxidant properties of ALA in its free form and their inclusion complexes with γ-cyclodextrin using this mutant yeast model. Both free forms R- and S-LA as well as 1:1 inclusion complexes with γ-cyclodextrin recovered growth of Δdps1 depending on the concentration and form. However, it has no effect on the growth of wild type fission yeast strain at all. Raman microspectroscopy was employed to understand the anti-oxidant property at the molecular level. A sensitive Raman band at 1602 cm-1 was monitored with and without addition of ALAs. It was found that 0.5 mM and 1.0 mM concentrations of ALAs had similar effect in both free and inclusion forms. At 2.5 mM ALAs, free forms inhibited the growth while inclusion complexes helped in recovered. 5.0 mM ALA showed inhibitory effect irrespective of form. Our results suggest that the Raman band at 1602 cm-1 is a good measure of oxidative stress in fission yeast.

  18. Introduction of β-cyclodextrin into poly(aspartic acid) matrix for adsorption and time-release of ibuprofen.

    PubMed

    Sun, Zhao-Yang; Shen, Ming-Xing; Yang, An-Wen; Liang, Cong-Qiang; Wang, Nan; Cao, Gui-Ping

    2011-01-21

    Biodegradable copolymers with molecule inclusion ability was prepared by introduction of β-cyclodextrin into poly(aspartic acid) matrices. The ibuprofen loading and dissolution properties of poly(aspartic acid)-β-cyclodextrin were investigated.

  19. The 2.0-A resolution structure of soybean beta-amylase complexed with alpha-cyclodextrin.

    PubMed

    Mikami, B; Hehre, E J; Sato, M; Katsube, Y; Hirose, M; Morita, Y; Sacchettini, J C

    1993-07-13

    New crystallographic findings are presented which offer a deeper understanding of the structure and functioning of beta-amylase, the first known exo-type starch-hydrolyzing enzyme. A refined three-dimensional structure of soybean beta-amylase, complexed with the inhibitor alpha-cyclodextrin, has been determined at 2.0-A resolution with a conventional R-value of 17.5%. The model contains 491 amino acid residues, 319 water molecules, 1 sulfate ion, and 1 alpha-cyclodextrin molecule. The protein consists of a core with an (alpha/beta)8 supersecondary structure, plus a smaller globular region formed by long loops (L3, L4, and L5) extending from beta-strands beta 3, beta 4, and beta 5. Between the two regions is a cleft that opens into a pocket whose floor contains the postulated catalytic center near the carboxyl group of Glu 186. The annular alpha-cyclodextrin binds in (and partly projects from) the cleft with its glucosyl O-2/O-3 face abutting the (alpha/beta)8 side and with its alpha-D(1 --> 4) glucosidic linkage progression running clockwise as viewed from that side. The ligand does not bind deeply enough to interact with the carboxyl group of Glu 186. Rather, it occupies most of the cleft entrance, strongly suggesting that alpha-cyclodextrin inhibits catalysis by blocking substrate access to the more deeply located reaction center. Of the various alpha-cyclodextrin interactions with protein residues in loops L4, L5, L6, and L7, most notable is the shallow inclusion complex formed with Leu 383 (in L7, on the core side of the cleft) through contacts of its methyl groups with the C-3 atoms of four of the ligand's D-glucopyranosyl residues. All six residues of the bound alpha-cyclodextrin are of 4C1 conformation and are joined by alpha-1,4 linkages with similar torsional angles to form a nearly symmetrical torus as reported for crystalline inclusion complexes with alpha-cyclodextrin. We envision a significant role for the methyl groups of Leu 383 at the cleft entrance

  20. Synthesis of polyrotaxanes from acetyl-β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Ristić, I. S.; Nikolić, L.; Nikolić, V.; Ilić, D.; Budinski-Simendić, J.

    2011-12-01

    Polyrotaxanes are intermediary products in the synthesis of topological gels. They are created by inclusion complex formation of hydrophobic linear macromolecules with cyclodextrins or their derivatives. Then, pairs of cyclodextrin molecules with covalently linkage were practically forming the nodes of the semi-flexible polymer network. Such gels are called topological gels and they can absorb huge quantities of water due to the net flexibility allowing the poly(ethylene oxide) chains to slide through the cyclodextrin cavities, without being pulled out altogether. For polyrotaxane formation poly(ethylene oxide) was used like linear macromolecules. There are hydroxyl groups at poly(ethylene oxide) chains, whereby the linking of the voluminous molecules should be made. To avoid the reaction of cyclodextrin OH groups with stoppers, they should be protected by, e.g., acetylation. In this work, the acetylation of the OH groups of β-cyclodextrin was performed by acetic acid anhydride with iodine as the catalyst. The acetylation reaction was assessed by the FTIR and HPLC method. By the HPLC analysis was found that the acetylation was completed in 20 minutes. Inserting of poly(ethylene oxide) with 4000 g/mol molecule mass into acetyl-β-cyclodextrin with 2:1 poly(ethylene oxide) monomer unit to acetyl-β-cyclodextrin ratio was also monitored by FTIR, and it was found that the process was completed in 12 h at the temperature of 10°C. If the process is performed at temperatures above 10°C, or for periods longer than 12 hours, the process of uncontrolled hydrolysis of acetate groups was initiated.

  1. Improved thermal stability of polylactic acid (PLA) composite film via PLA-β-cyclodextrin-inclusion complex systems.

    PubMed

    Byun, Youngjae; Rodriguez, Katia; Han, Jung H; Kim, Young Teck

    2015-11-01

    The effects of the incorporation of PLA-β-cyclodextrin-inclusion complex (IC) and β-cyclodextrin (β-CD) on biopolyester PLA films were investigated. Thermal stability, surface morphology, barrier, and mechanical properties of the films were measured at varying IC (1, 3, 5, and 7%) and β-CD (1 and 5%) concentrations. The PLA-IC-composite films (IC-PLA-CFs) showed uniform morphological structure, while samples containing β-CD (β-CD-PLA-CFs) showed high agglomeration of β-CD due to poor interfacial interaction between β-CD and PLA moieties. According to the thermal property analysis, the 5% IC-PLA-CFs showed 6.6 times lower dimensional changes (6.5%) at the temperature range of 20-80°C than that of pure PLA film (43.0%). The increase of IC or β-CD content in the PLA-composite films shifted the glass transition and crystallization temperature to higher temperature regions. The crystallinity of both composite films improved by increasing IC or β-CD content. Both composite films had higher oxygen and water vapor permeability as IC or β-CD content increased in comparison to pure PLA film. All the composite films had less flexibility and lower tensile strength than the pure PLA film. In conclusion, this study shows that the IC technique is valuable to improve the thermal expansion stability of PLA-based films. Published by Elsevier B.V.

  2. Convenient QSAR model for predicting the complexation of structurally diverse compounds with beta-cyclodextrins.

    PubMed

    Pérez-Garrido, Alfonso; Morales Helguera, Aliuska; Abellán Guillén, Adela; Cordeiro, M Natália D S; Garrido Escudero, Amalio

    2009-01-15

    This paper reports a QSAR study for predicting the complexation of a large and heterogeneous variety of substances (233 organic compounds) with beta-cyclodextrins (beta-CDs). Several different theoretical molecular descriptors, calculated solely from the molecular structure of the compounds under investigation, and an efficient variable selection procedure, like the Genetic Algorithm, led to models with satisfactory global accuracy and predictivity. But the best-final QSAR model is based on Topological descriptors meanwhile offering a reasonable interpretation. This QSAR model was able to explain ca. 84% of the variance in the experimental activity, and displayed very good internal cross-validation statistics and predictivity on external data. It shows that the driving forces for CD complexation are mainly hydrophobic and steric (van der Waals) interactions. Thus, the results of our study provide a valuable tool for future screening and priority testing of beta-CDs guest molecules.

  3. Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin.

    PubMed

    Liu, Zhichang; Frasconi, Marco; Lei, Juying; Brown, Zachary J; Zhu, Zhixue; Cao, Dennis; Iehl, Julien; Liu, Guoliang; Fahrenbach, Albert C; Botros, Youssry Y; Farha, Omar K; Hupp, Joseph T; Mirkin, Chad A; Fraser Stoddart, J

    2013-01-01

    Gold recovery using environmentally benign chemistry is imperative from an environmental perspective. Here we report the spontaneous assembly of a one-dimensional supramolecular complex with an extended {[K(OH₂)₆][AuBr₄](α-cyclodextrin)₂}n chain superstructure formed during the rapid co-precipitation of α-cyclodextrin and KAuBr₄ in water. This phase change is selective for this gold salt, even in the presence of other square-planar palladium and platinum complexes. From single-crystal X-ray analyses of six inclusion complexes between α-, β- and γ-cyclodextrins with KAuBr₄ and KAuCl₄, we hypothesize that a perfect match in molecular recognition between α-cyclodextrin and [AuBr₄](-) leads to a near-axial orientation of the ion with respect to the α-cyclodextrin channel, which facilitates a highly specific second-sphere coordination involving [AuBr₄](-) and [K(OH₂)₆](+) and drives the co-precipitation of the 1:2 adduct. This discovery heralds a green host-guest procedure for gold recovery from gold-bearing raw materials making use of α-cyclodextrin-an inexpensive and environmentally benign carbohydrate.

  4. Cyclodextrin-based supramolecular systems for drug delivery: Recent progress and future perspective

    PubMed Central

    Zhang, Jianxiang; Ma, Peter X

    2013-01-01

    The excellent biocompatibility and unique inclusion capability as well as powerful functionalization capacity of cyclodextrins and their derivatives make them especially attractive for engineering novel functional materials for biomedical applications. There has been increasing interest recently to fabricate supramolecular systems for drug and gene delivery based on cyclodextrin materials. This review focuses on state of the art and recent advances in the construction of cyclodextrin-based assemblies and their applications for controlled drug delivery. First, we introduce cyclodextrin materials utilized for self-assembly. The fabrication technologies of supramolecular systems including nanoplatforms and hydrogels as well as their applications in nanomedicine and pharmaceutical sciences are then highlighted. At the end, the future directions of this field are discussed. PMID:23673149

  5. Cyclodextrins, blood-brain barrier, and treatment of neurological diseases.

    PubMed

    Vecsernyés, Miklós; Fenyvesi, Ferenc; Bácskay, Ildikó; Deli, Mária A; Szente, Lajos; Fenyvesi, Éva

    2014-11-01

    Biological barriers are the main defense systems of the homeostasis of the organism and protected organs. The blood-brain barrier (BBB), formed by the endothelial cells of brain capillaries, not only provides nutrients and protection to the central nervous system but also restricts the entry of drugs, emphasizing its importance in the treatment of neurological diseases. Cyclodextrins are increasingly used in human pharmacotherapy. Due to their favorable profile to form hydrophilic inclusion complexes with poorly soluble active pharmaceutical ingredients, they are present as excipients in many marketed drugs. Application of cyclodextrins is widespread in formulations for oral, parenteral, nasal, pulmonary, and skin delivery of drugs. Experimental and clinical data suggest that cyclodextrins can be used not only as excipients for centrally acting marketed drugs like antiepileptics, but also as active pharmaceutical ingredients to treat neurological diseases. Hydroxypropyl-β-cyclodextrin received orphan drug designation for the treatment of Niemann-Pick type C disease. In addition to this rare lysosomal storage disease with neurological symptoms, experimental research revealed the potential therapeutic use of cyclodextrins and cyclodextrin nanoparticles in neurodegenerative diseases, stroke, neuroinfections and brain tumors. In this context, the biological effects of cyclodextrins, their interaction with plasma membranes and extraction of different lipids are highly relevant at the level of the BBB. Copyright © 2015 IMSS. Published by Elsevier Inc. All rights reserved.

  6. Supra-molecular inclusion complexation of ionic liquid 1-butyl-3-methylimidazolium octylsulphate with α- and β-cyclodextrins

    NASA Astrophysics Data System (ADS)

    Banjare, Manoj Kumar; Behera, Kamalakanta; Satnami, Manmohan L.; Pandey, Siddharth; Ghosh, Kallol K.

    2017-12-01

    Host-guest complexation between ionic liquid (IL) 1-butyl-3-methylimidazolium octylsulphate [Bmim][OS] and cyclodextrins (α- and β- CDs) have been studied. Surface tension, conductivity measurements revealed the formation of 1:1 (M) stoichiometry for inclusion complexes (ICs) and further confirmed by UV-Visible and FT-IR results. The nature of the complexes has been established using interfacial and thermodynamic parameters. The aggregation number, Stern-Volmer constants, association constants were obtained from fluorescence quenching and Benesi-Hildebrand methods. The critical micelle concentration (cmc) and association constants of [Bmim][OS] are higher for β-CD as compared to α-CD. FT-IR spectra indicated that CDs and [Bmim][OS] could from ICs with stoichiometry 1:1 (M).

  7. In vitro investigations of α-amylase mediated hydrolysis of cyclodextrins in the presence of ibuprofen, flurbiprofen, or benzo[a]pyrene.

    PubMed

    Lumholdt, Ludmilla Riisager; Holm, René; Jørgensen, Erling Bonne; Larsen, Kim Lambertsen

    2012-11-15

    In vitro studies of α-amylase degradation of α-, β- and γ-cyclodextrins and 2-hydroxypropyl-β- and -γ-cyclodextrins were investigated spectrophotometrically by measuring the formation of reducing sugars, the reaction products of α-amylase degradation. This was done to evaluate potential degradation and thereby biological conversion of the cyclodextrins if dosed orally, as the intestinal tract contains α-amylase for digestive purposes. The results demonstrated that only γ- and 2-hydroxypropyl-γ-cyclodextrins can be degraded by α-amylase to a relevant extent, that is, γ- and 2-hydroxypropyl-γ-cyclodextrins have different biopharmaceutical behaviours than the other evaluated cyclodextrins. The rate of degradation was affected by the addition of the inclusion complex forming additives flurbiprofen, ibuprofen and benzo[a]pyrene. This effect between the degradation dynamics and the included additives was caused by a correlation between solubility of the additives and the stability of the complex. Copyright © 2012 Elsevier Ltd. All rights reserved.

  8. Spectral and theoretical study on complexation of sulfamethoxazole with β- and HPβ-cyclodextrins in binary and ternary systems

    NASA Astrophysics Data System (ADS)

    Varghese, Beena; Suliman, FakhrEldin O.; Al-Hajri, Aalia; Al Bishri, Nahed Surur S.; Al-Rwashda, Nathir

    2018-02-01

    The inclusion complexes of sulfamethoxazole (SMX) with β-cyclodextrin (βCD) and (2-hydroxypropyl) β-cyclodextrin (HPβCD) were prepared. Fluorescence spectroscopy and electrospray mass spectrometry, ESI-MS, were used to investigate and characterize the inclusion complexation of SMX with cyclodextrins in solutions. Whereas in the solid state the complexes were characterized by Fourier transform infrared spectroscopy (FTIR), powder X-ray diffraction (PXRD) and Raman techniques. Enhanced twisted intramolecular charge transfer (TICT), emission as well as local excited (LE) bands were observed upon addition of HPβCD indicate that SMX enters deeper into the cyclodextrins cavity. The stoichiometries and association constants of these complexes have been determined by monitoring the fluorescence data. The effect of presence of ternary components like arginine and cysteine on the complexation efficiency of SMX with cyclodextrins was investigated. Molecular Dynamic simulations were also performed to shed an atomistic insight into the complexation mechanism. The results obtained showed that complexes of SMX with both cyclodextrins are stabilized in aqueous media by strong hydrogen bonding interactions.

  9. Using molecular recognition of beta-cyclodextrin to determine molecular weights of low-molecular-weight explosives by MALDI-TOF mass spectrometry.

    PubMed

    Zhang, Min; Shi, Zhen; Bai, Yinjuan; Gao, Yong; Hu, Rongzu; Zhao, Fenqi

    2006-02-01

    This study presents a novel method for determining the molecular weights of low molecular weight (MW) energetic compounds through their complexes of beta-cyclodextrin (beta-CD) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) in a mass range of 500 to 1700 Da, avoiding matrix interference. The MWs of one composite explosive composed of 2,6-DNT, TNT, and RDX, one propellant with unknown components, and 14 single-compound explosives (RDX, HMX, 3,4-DNT, 2,6-DNT, 2,5-DNT, 2,4,6-TNT, TNAZ, DNI, BTTN, NG, TO, NTO, NP, and 662) were measured. The molecular recognition and inclusion behavior of beta-CD to energetic materials (EMs) were investigated. The results show that (1) the established method is sensitive, simple, accurate, and suitable for determining the MWs of low-MW single-compound explosives and energetic components in composite explosives and propellants; and (2) beta-CD has good inclusion and modular recognition abilities to the above EMs.

  10. Enhancement of selectivity and resolution in the enantioseparation of uncharged compounds using mixtures of oppositely charged cyclodextrins in capillary electrophoresis.

    PubMed

    Abushoffa, Adel M; Fillet, Marianne; Servais, Anne-Catherine; Hubert, Philippe; Crommen, Jacques

    2003-01-01

    The enantiomeric separation of some nonsteroidal anti-inflammatory drugs (NSAIDs) was investigated in capillary electrophoresis (CE) using dual systems with mixtures of charged cyclodextrin (CD) derivatives. A significant enhancement of selectivity and resolution could be achieved in the enantioseparation of these analytes in their uncharged form by the simultaneous addition of two oppositely charged CD derivatives to the background electrolyte. The combination of the single-isomer cationic CD, permethyl-6-monoamino-6-monodeoxy-beta-CD (PMMAbetaCD) and the single-isomer polyanionic CD, heptakis-6-sulfato-beta-cyclodextrin (HSbetaCD) in a pH 2.5 phosphoric acid-triethanolamine buffer, was designed and employed for the enantioseparation of profens. The improvement in selectivity and resolution can be attributed to the fact that the two CDs, which lead to independent and enantioselective complexation with the analyte enantiomers, have not only opposite effects on the electrophoretic mobility of these compounds but also opposite affinity patterns towards the enantiomers of these compounds. Binding constants for these enantiomers with each CD were determined using linear regression approach, in order to be able to predict the effect of the concentrations of the two CDs on enantiomeric selectivity and resolution in such dual systems.

  11. A cyclodextrin-capped histone deacetylase inhibitor.

    PubMed

    Amin, Jahangir; Puglisi, Antonino; Clarke, James; Milton, John; Wang, Minghua; Paranal, Ronald M; Bradner, James E; Spencer, John

    2013-06-01

    We have synthesized a β-cyclodextrin (βCD)-capped histone deacetylase (HDAC) inhibitor 3 containing an alkyl linker and a zinc-binding hydroxamic acid motif. Biological evaluation (HDAC inhibition studies) of 3 enabled us to establish the effect of replacing an aryl cap (in SAHA (vorinostat,)) 1 by a large saccharidic scaffold "cap". HDAC inhibition was observed for 3, to a lesser extent than SAHA, and rationalized by molecular docking into the active site of HDAC8. However, compound 3 displayed no cellular activity. Copyright © 2013 Elsevier Ltd. All rights reserved.

  12. Naked eye screening of 11 phenolic compounds and colorimetric determination using polydiacetylene vesicles with α-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Anekthirakun, Pimpimon; Sukwattanasinitt, Mongkol; Tuntulani, Thawatchai; Imyim, Apichat

    2013-07-01

    The colorimetric response (CR) of poly(10,12-pentacosadiynoic acid) vesicles (PPCDA) induced by α-cyclodextrin (α-CD) in an aqueous solution has been studied. Various parameters affecting the CR, such as response time and concentration were investigated. The blue color of 0.01 mM PPCDA solution became pinkish red with the addition of α-CD at the concentration higher than 3 mM. The inhibition of the color transition from blue to red was investigated using 11 phenolic compounds. The color transition could be inhibited and observed by naked eye in the presence of 4 phenolic compounds, i.e. 4-nitrophenol (4-NP) and 4-bromophenol (4-BP) and 4-chlorophenol (4-CP) and 3-nitrophenol (3-NP). A colorimetric method for the determination of these compounds was validated and applied for surface water analysis. The linear range from the plot of CR against phenolic compounds concentration was in the order of 0.5-2.0 mM with R2 more than 0.99. The recoveries were 90-95% with good precision (1-4%RSD, n = 10).

  13. Supramolecular structure of glibenclamide and β-cyclodextrins complexes.

    PubMed

    Lucio, David; Irache, Juan Manuel; Font, María; Martínez-Ohárriz, María Cristina

    2017-09-15

    Glibenclamide is an antidiabetic drug showing low bioavailability as consequence of its low solubility. To solve this drawback, the interaction with cyclodextrins has been proposed. The formation of GB-βCDs inclusion complexes was carried out using different methods, βCD derivatives and drug-to-cyclodextrin ratios. The structures of the corresponding complexes have been studied by molecular modelling, X-ray diffraction and differential thermal analysis. The dissolution behavior of inclusion complexes has been compared to that of pure GB. Dimeric inclusion complexes were obtained with different CD disposals, head-to-head for βCD and head-to-tail for HPβCD and RMβCD. Amorphous inclusion complexes were obtained by employing methods of freeze-drying or coevaporation in ammonia-water. However, crystalline structures were formed by kneading and coevaporation in ethanol/water in the case of GB-βCD complexes. The arrangement of these structures depended on the GB:βCD ratio, yielding cage type structures for 1:3 and 1:5 ratios and channel-type structures for higher GB contents. The amount of GB released and its dissolution rate was considerably increased by the use of amorphous inclusion complexes; whereas, slower GB release rates were found from crystalline inclusion complexes formed by kneading or coevaporation in ethanol/water. In addition, it was found that the porous structure strongly conditioned the GB dissolution rate from crystalline products. Copyright © 2017 Elsevier B.V. All rights reserved.

  14. Biophysical aspects of cyclodextrin interaction with paraoxon.

    PubMed

    Soni, Sunil-Datta; Bhonsle, Jayendra B; Garcia, Gregory E

    2014-03-01

    Cyclodextrins are torus-shaped polymers of glucose that can bind organophosphorous compounds such as nerve agents and pesticides. We demonstrate here that cyclodextrin can bind up to two paraoxon molecules with a K(av) of 6775 M(-1). Molecular modeling shows that the paraoxon appears to bind in polar opposite orientation and have an average binding energy of -89 Kcals/mol. Published 2013. This article is a U.S. Government work and is in the public domain in the USA. Published 2013. This article is a U.S. Government work and is in the public domain in the USA.

  15. Cyclodextrin-enhanced solubilization of organic contaminants with implications for aquifer remediation

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    McCray, J.E.; Boving, T.B.; Brusseau, M.L.

    2000-12-31

    Reagents that enhance the aqueous solubility of nonaqueous phase organic liquid (NAPL) contaminants are under investigation for use in enhanced subsurface remediation technologies. Cyclodextrin, a glucose-based molecule, is such a reagent. In this paper, laboratory experiments and numerical model simulations are used to evaluate and understand the potential remediation performance of cyclodextrin. Physical properties of cyclodextrin solutions such as density, viscosity, and NAPL-aqueous interfacial tension are measured. Their analysis indicates that no serious obstacles exist related to fluid properties that would prevent the use of cyclodextrin solutions for subsurface NAPL remediation. Cyclodextrin-enhanced solubilization for a large suite of typical groundmore » water contaminants is measured in the laboratory, and the results are related to the physiochemical properties of the organic compounds. The most-hydrophobic contaminants experience a larger relative solubility enhancement than the less-hydrophobic contaminants but have lower aqueous-phase apparent solubilities. Numerical model simulations of enhanced-solubilization flushing of NAPL-contaminated soil demonstrate that the more-hydrophilic compounds exhibit the greatest mass-removal relates due to their greater apparent solubilities, and thus are initially more effectively removed from soil by enhanced-solubilization-flushing reagents. However, the relatively more hydrophobic contaminants exhibit a greater improvement in contaminant mass-removal (compared with water flushing) than that exhibited for the relatively hydrophilic contaminants.« less

  16. Influence of the preparation method on the physicochemical properties of indomethacin and methyl-β-cyclodextrin complexes.

    PubMed

    Rudrangi, Shashi Ravi Suman; Bhomia, Ruchir; Trivedi, Vivek; Vine, George J; Mitchell, John C; Alexander, Bruce David; Wicks, Stephen Richard

    2015-02-20

    The main objective of this study was to investigate different manufacturing processes claimed to promote inclusion complexation between indomethacin and cyclodextrins in order to enhance the apparent solubility and dissolution properties of indomethacin. Especially, the effectiveness of supercritical carbon dioxide processing for preparing solid drug-cyclodextrin inclusion complexes was investigated and compared to other preparation methods. The complexes were prepared by physical mixing, co-evaporation, freeze drying from aqueous solution, spray drying and supercritical carbon dioxide processing methods. The prepared complexes were then evaluated by scanning electron microscopy, differential scanning calorimetry, X-ray powder diffraction, solubility and dissolution studies. The method of preparation of the inclusion complexes was shown to influence the physicochemical properties of the formed complexes. Indomethacin exists in a highly crystalline solid form. Physical mixing of indomethacin and methyl-β-cyclodextrin appeared not to reduce the degree of crystallinity of the drug. The co-evaporated and freeze dried complexes had a lower degree of crystallinity than the physical mix; however the lowest degree of crystallinity was achieved in complexes prepared by spray drying and supercritical carbon dioxide processing methods. All systems based on methyl-β-cyclodextrin exhibited better dissolution properties than the drug alone. The greatest improvement in drug dissolution properties was obtained from complexes prepared using supercritical carbon dioxide processing, thereafter by spray drying, freeze drying, co-evaporation and finally by physical mixing. Supercritical carbon dioxide processing is well known as an energy efficient alternative to other pharmaceutical processes and may have application for the preparation of solid-state drug-cyclodextrin inclusion complexes. It is an effective and economic method that allows the formation of solid complexes with a

  17. Construction and Characterization of a Chitosan-Immobilized-Enzyme and β-Cyclodextrin-Included-Ferrocene-Based Electrochemical Biosensor for H₂O₂ Detection.

    PubMed

    Dong, Wenbo; Wang, Kaiyin; Chen, Yu; Li, Weiping; Ye, Yanchun; Jin, Shaohua

    2017-07-28

    An electrochemical detection biosensor was prepared with the chitosan-immobilized-enzyme (CTS-CAT) and β-cyclodextrin-included-ferrocene (β-CD-FE) complex for the determination of H₂O₂. Ferrocene (FE) was included in β-cyclodextrin (β-CD) to increase its stability. The structure of the β-CD-FE was characterized. The inclusion amount, inclusion rate, and electrochemical properties of inclusion complexes were determined to optimize the reaction conditions for the inclusion. CTS-CAT was prepared by a step-by-step immobilization method, which overcame the disadvantages of the conventional preparation methods. The immobilization conditions were optimized to obtain the desired enzyme activity. CTS-CAT/β-CD-FE composite electrodes were prepared by compositing the CTS-CAT with the β-CD-FE complex on a glassy carbon electrode and used for the electrochemical detection of H₂O₂. It was found that the CTS-CAT could produce a strong reduction peak current in response to H₂O₂ and the β-CD-FE could amplify the current signal. The peak current exhibited a linear relationship with the H₂O₂ concentration in the range of 1.0 × 10 -7 -6.0 × 10 -3 mol/L. Our work provided a novel method for the construction of electrochemical biosensors with a fast response, good stability, high sensitivity, and a wide linear response range based on the composite of chitosan and cyclodextrin.

  18. Analyses of polycyclic aromatic hydrocarbon (PAH) and chiral-PAH analogues-methyl-β-cyclodextrin guest-host inclusion complexes by fluorescence spectrophotometry and multivariate regression analysis.

    PubMed

    Greene, LaVana; Elzey, Brianda; Franklin, Mariah; Fakayode, Sayo O

    2017-03-05

    The negative health impact of polycyclic aromatic hydrocarbons (PAHs) and differences in pharmacological activity of enantiomers of chiral molecules in humans highlights the need for analysis of PAHs and their chiral analogue molecules in humans. Herein, the first use of cyclodextrin guest-host inclusion complexation, fluorescence spectrophotometry, and chemometric approach to PAH (anthracene) and chiral-PAH analogue derivatives (1-(9-anthryl)-2,2,2-triflouroethanol (TFE)) analyses are reported. The binding constants (K b ), stoichiometry (n), and thermodynamic properties (Gibbs free energy (ΔG), enthalpy (ΔH), and entropy (ΔS)) of anthracene and enantiomers of TFE-methyl-β-cyclodextrin (Me-β-CD) guest-host complexes were also determined. Chemometric partial-least-square (PLS) regression analysis of emission spectra data of Me-β-CD-guest-host inclusion complexes was used for the determination of anthracene and TFE enantiomer concentrations in Me-β-CD-guest-host inclusion complex samples. The values of calculated K b and negative ΔG suggest the thermodynamic favorability of anthracene-Me-β-CD and enantiomeric of TFE-Me-β-CD inclusion complexation reactions. However, anthracene-Me-β-CD and enantiomer TFE-Me-β-CD inclusion complexations showed notable differences in the binding affinity behaviors and thermodynamic properties. The PLS regression analysis resulted in square-correlation-coefficients of 0.997530 or better and a low LOD of 3.81×10 -7 M for anthracene and 3.48×10 -8 M for TFE enantiomers at physiological conditions. Most importantly, PLS regression accurately determined the anthracene and TFE enantiomer concentrations with an average low error of 2.31% for anthracene, 4.44% for R-TFE and 3.60% for S-TFE. The results of the study are highly significant because of its high sensitivity and accuracy for analysis of PAH and chiral PAH analogue derivatives without the need of an expensive chiral column, enantiomeric resolution, or use of a polarized

  19. Bioadhesive tablets containing cyclodextrin complex of itraconazole for the treatment of vaginal candidiasis.

    PubMed

    Cevher, Erdal; Açma, Ayşe; Sinani, Genada; Aksu, Buket; Zloh, Mire; Mülazımoğlu, Lütfiye

    2014-08-01

    Itraconazole (ITR) is commonly used in the treatment of Candida infections. It has a nephrotoxic effect and low bioavailability in patients who suffer from renal insufficiency, and its poor solubility in water makes ITR largely unavailable. Cyclodextrins (CyDs) are used to form inclusion complexes with drugs to improve their aqueous solubility and to reduce their side effects. In this study, ITR was complexed with γ-cyclodextrin (γ-CyD), hydroxypropyl-β-cyclodextrin (HP-β-CyD), methyl-β-cyclodextrin (Met-β-CyD) and sulphobutyl ether-β-cyclodextrin (SBE7-β-CyD) to increase its water solubility and to reduce the side effects of the drug without decreasing antifungal activity. Complex formation between ITR and CyDs was evaluated using SEM, (1)H NMR and XRD studies. The antifungal activity of the complexes was analyzed on Candida albicans strains, and the susceptibility of the strains was found to be higher for the ITR-SBE7-β-CyD complex than for the complexes that were prepared with other CyDs. Vaginal bioadhesive sustained release tablet formulations were developed using the ITR-SBE7-β-CyD inclusion complex to increase the residence time of ITR in the vagina, thereby boosting the efficacy of the treatment. The swelling, matrix erosion and bioadhesion properties of formulations and the drug release rate of these tablets were analyzed, and the most therapeutically effective vaginal formulation was determined. Copyright © 2014 Elsevier B.V. All rights reserved.

  20. Separation of profen enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors.

    PubMed

    Blanco, M; Coello, J; Iturriaga, H; Maspoch, S; Pérez-Maseda, C

    1998-01-09

    A method for resolving the enantiomers of various 2-arylpropionic acids (viz. ketoprofen, ibuprofen and fenoprofen) by capillary zone electrophoresis (CZE) using a background electrolyte (BGE) containing a cyclodextrin as chiral selector is proposed. The effects of the type of cyclodextrin used and its concentration on resolution were studied and heptakis-2,3,6-tri- O-methyl-beta-cyclodextrin was found to be the sole effective choice for the quantitative enantiomeric resolution of all the compounds tested. The influence of pH, BGE concentration, capillary temperature and addition of methanol to the BGE on resolution and other separation-related parameters was also studied. The three compounds studied can be enantiomerically resolved with a high efficiency in a short time (less than 20 min) with no capillary treatment. This makes the proposed method suitable for assessing the enantiomeric purity of commercially available pharmaceuticals.

  1. A supramolecular complex between proteinases and beta-cyclodextrin that preserves enzymatic activity: physicochemical characterization.

    PubMed

    Denadai, Angelo M L; Santoro, Marcelo M; Lopes, Miriam T P; Chenna, Angélica; de Sousa, Frederico B; Avelar, Gabriela M; Gomes, Marco R Túlio; Guzman, Fanny; Salas, Carlos E; Sinisterra, Rubén D

    2006-01-01

    Cyclodextrins are suitable drug delivery systems because of their ability to subtly modify the physical, chemical, and biological properties of guest molecules through labile interactions by formation of inclusion and/or association complexes. Plant cysteine proteinases from Caricaceae and Bromeliaceae are the subject of therapeutic interest, because of their anti-inflammatory, antitumoral, immunogenic, and wound-healing properties. In this study, we analyzed the association between beta-cyclodextrin (betaCD) and fraction P1G10 containing the bioactive proteinases from Carica candamarcensis, and described the physicochemical nature of the solid-state self-assembled complexes by Fourier transform infrared (FTIR) spectroscopy, thermogravimetry (TG), differential scanning calorimetry (DSC), X-ray powder diffraction (XRD), and nuclear magnetic resonance (NMR), as well as in solution by circular dichroism (CD), isothermal titration calorimetry (ITC), and amidase activity. The physicochemical analyses suggest the formation of a complex between P1G10 and betaCD. Higher secondary interactions, namely hydrophobic interactions, hydrogen bonding and van der Waals forces were observed at higher P1G10 : betaCD mass ratios. These results provide evidence of the occurrence of strong solid-state supramolecular non-covalent interactions between P1G10 and betaCD. Microcalorimetric analysis demonstrates that complexation results in a favorable enthalpic contribution, as has already been described during formation of similar betaCD inclusion compounds. The amidase activity of the complex shows that the enzyme activity is not readily available at 24 hours after dissolution of the complex in aqueous buffer; the proteinase becomes biologically active by the second day and remains stable until day 16, when a gradual decrease occurs, with basal activity attained by day 29. The reported results underscore the potential for betaCDs as candidates for complexing cysteine proteinases, resulting

  2. Nanoliposome-Encapsulated Brinzolamide-hydropropyl-β-cyclodextrin Inclusion Complex: A Potential Therapeutic Ocular Drug-Delivery System

    PubMed Central

    Wang, Fazhan; Bao, Xingting; Fang, Aiping; Li, Huili; Zhou, Yang; Liu, Yongmei; Jiang, Chunling; Wu, Jinhui; Song, Xiangrong

    2018-01-01

    Novel ocular drug delivery systems (NODDSs) remain to be explored to overcome the anatomical and physiological barriers of the eyes. This study was to encapsulate brinzolamide (BRZ)-hydropropyl-β-cyclodextrin (HP-β-CD) inclusion complex (HP-β-CD/BRZ) into nanoliposomes and investigate its potential as one of NODDS to improve BRZ local glaucomatous therapeutic effect. HP-β-CD/BRZ was firstly prepared to enhance the solubility of poorly water-soluble BRZ. The HP-β-CD/BRZ loaded nanoliposomes (BCL) were subsequently constructed by thin-film dispersion method. After the optimization of the ratio of BRZ to HP-β-CD, the optimal BCL showed an average size of 82.29 ± 6.20 nm, ζ potential of -3.57 ± 0.46 mV and entrapment efficiency (EE) of 92.50 ± 2.10% with nearly spherical in shape. The X-ray diffraction (XRD) confirmed the formation of HP-β-CD/BRZ and BCL. The in vitro release study of BCL was evaluated using the dialysis technique, and BCL showed moderate sustained release. BCL (1 mg/mL BRZ) showed a 9.36-fold increase in the apparent permeability coefficient and had a sustained and enhanced intraocular pressure reduction efficacy when compared with the commercially available formulation (BRZ-Sus) (10 mg/mL BRZ). In conclusion, BCL might have a promising future as a NODDS for glaucoma treatment. PMID:29487529

  3. The influence of the preparation methods on the inclusion of model drugs in a beta-cyclodextrin cavity.

    PubMed

    Salústio, P J; Feio, G; Figueirinhas, J L; Pinto, J F; Cabral Marques, H M

    2009-02-01

    The work aims to prove the complexation of two model drugs (ibuprofen, IB and indomethacin, IN) by beta-cyclodextrin (betaCD), and the effect of water in such a process, and makes a comparison of their complexation yields. Two methods were considered: kneading of a binary mixture of the drug, betaCD, and inclusion of either IB or IN in aqueous solutions of betaCD. In the latter method water was removed by air stream, spray-drying and freeze-drying. To prove the formation of complexes in final products, optical microscopy, UV spectroscopy, IR spectroscopy, DSC, X-ray and NMR were considered. Each powder was added to an acidic solution (pH=2) to quantify the concentration of the drug inside betaCD cavity. Other media (pH=5 and 7) were used to prove the existence of drug not complexed in each powder, as the drugs solubility increases with the pH. It was observed that complexation occurred in all powders, and that the fraction of drug inside the betaCD did not depend neither on the method of complexation nor on the processes of drying considered.

  4. Characterization of Albendazole-Randomly Methylated-β-Cyclodextrin Inclusion Complex and In Vivo Evaluation of Its Antihelmitic Activity in a Murine Model of Trichinellosis

    PubMed Central

    García, Agustina; Leonardi, Darío; Vasconi, María D.; Hinrichsen, Lucila I.; Lamas, María C.

    2014-01-01

    Albendazole is a benzimidazole carbamate extensively used in oral chemotherapy against intestinal parasites, due to its broad spectrum activity, good tolerance and low cost. However, the drug has the disadvantage of poor bioavailability due to its very low solubility in water; as a consequence, a very active area of research focuses on the development of new pharmaceutical formulations to increase its solubility, dissolution rate, and bioavailability. The primary objective of this study was to prepare randomly methylated β-cyclodextrins inclusion complexes to increase albendazole dissolution rate, in order to enhance its antiparasitic activity. This formulation therapeutic efficacy was contrasted with that of the pure drug by treating Trichinella spiralis infected mice during the intestinal phase of the parasite cycle, on days five and six post-infection. This protocol significantly decreased muscle larval burden measured in the parenteral stage on day 30 post-infection, when compared with the untreated control. Thus, it could be demonstrated that the inclusion complexes improve the in vivo therapeutic activity of albendazole. PMID:25406084

  5. Pharmaceutical applications of cyclodextrins: effects on drug permeation through biological membranes.

    PubMed

    Loftsson, Thorsteinn; Brewster, Marcus E

    2011-09-01

    Cyclodextrins are useful solubilizing excipients that have gained currency in the formulator's armamentarium based on their ability to temporarily camouflage undesirable physicochemical properties. In this context cyclodextrins can increase oral bioavailability, stabilize compounds to chemical and enzymatic degradation and can affect permeability through biological membranes under certain circumstances. This latter property is examined herein as a function of the published literature as well as work completed in our laboratories.   Cyclodextrins can increase the uptake of drugs through biological barriers if the limiting barrier component is the unstirred water layer (UWL) that exists between the membrane and bulk water. This means that cyclodextrins are most useful when they interact with lipophiles in systems where such an UWL is present and contributes significantly to the barrier properties of the membrane. Furthermore, these principles are used to direct the optimal formulation of drugs in cyclodextrins. A second related critical success factor in the formulation of cyclodextrin-based drug product is an understanding of the kinetics and thermodynamics of complexation and the need to optimize the cyclodextrin amount and drug-to-cyclodextrin ratios. Drug formulations, especially those targeting compartments associated with limited dissolution (i.e. the eye, subcutaneous space, etc.), should be carefully designed such that the thermodynamic activity of the drug in the formulation is optimal meaning that there is sufficient cyclodextrin to solubilize the drug but not more than that. Increasing the cyclodextrin concentration decreases the formulation 'push' and may reduce the bioavailability of the system. A mechanism-based understanding of cyclodextrin complexation is essential for the appropriate formulation of contemporary drug candidates. © 2011 The Authors. JPP © 2011 Royal Pharmaceutical Society.

  6. Equilibrium location for spherical DNA and toroidal cyclodextrin

    NASA Astrophysics Data System (ADS)

    Sarapat, Pakhapoom; Baowan, Duangkamon; Hill, James M.

    2018-05-01

    Cyclodextrin comprises a ring structure composed of glucose molecules with an ability to form complexes of certain substances within its central cavity. The compound can be utilised for various applications including food, textiles, cosmetics, pharmaceutics, and gene delivery. In gene transfer, the possibility of forming complexes depends upon the interaction energy between cyclodextrin and DNA molecules which here are modelled as a torus and a sphere, respectively. Our proposed model is derived using the continuum approximation together with the Lennard-Jones potential, and the total interaction energy is obtained by integrating over both the spherical and toroidal surfaces. The results suggest that the DNA prefers to be symmetrically situated about 1.2 Å above the centre of the cyclodextrin to minimise its energy. Furthermore, an optimal configuration can be determined for any given size of torus and sphere.

  7. Influence of valine enantiomer configuration on the molecular dynamics simulation of their separation by β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Alvira, Elena

    2017-07-01

    The influence of enantiomeric configurations on the separation of valine by β-cyclodextrin with different solvents, is analysed by a molecular dynamics simulation at constant temperature. Different methods to select the initial dispositions of valine enantiomers in the trajectories are proposed, and their influence on the interaction energy, residence time, elution order and capacity to form inclusion complexes is studied. The residence time is the most influenced quantity, whereas the capacity to form inclusion complexes is hardly affected by enantiomeric dispositions. In any case, guests tend to locate in the same areas of β-cyclodextrin but with different orientations according to disposition.

  8. Selective isolation of gold facilitated by second-sphere coordination with α-cyclodextrin

    PubMed Central

    Liu, Zhichang; Frasconi, Marco; Lei, Juying; Brown, Zachary J.; Zhu, Zhixue; Cao, Dennis; Iehl, Julien; Liu, Guoliang; Fahrenbach, Albert C.; Botros, Youssry Y.; Farha, Omar K.; Hupp, Joseph T.; Mirkin, Chad A.; Fraser Stoddart, J.

    2013-01-01

    Gold recovery using environmentally benign chemistry is imperative from an environmental perspective. Here we report the spontaneous assembly of a one-dimensional supramolecular complex with an extended {[K(OH2)6][AuBr4](α-cyclodextrin)2}n chain superstructure formed during the rapid co-precipitation of α-cyclodextrin and KAuBr4 in water. This phase change is selective for this gold salt, even in the presence of other square-planar palladium and platinum complexes. From single-crystal X-ray analyses of six inclusion complexes between α-, β- and γ-cyclodextrins with KAuBr4 and KAuCl4, we hypothesize that a perfect match in molecular recognition between α-cyclodextrin and [AuBr4]− leads to a near-axial orientation of the ion with respect to the α-cyclodextrin channel, which facilitates a highly specific second-sphere coordination involving [AuBr4]− and [K(OH2)6]+ and drives the co-precipitation of the 1:2 adduct. This discovery heralds a green host–guest procedure for gold recovery from gold-bearing raw materials making use of α-cyclodextrin—an inexpensive and environmentally benign carbohydrate. PMID:23673640

  9. A combinatorial approach of inclusion complexation and dendrimer synthesization for effective targeting EGFR-TK.

    PubMed

    Shende, Pravin; Patil, Sampada; Gaud, R S

    2017-07-01

    The aim of the present study was to use a combinatorial approach of inclusion complexation and dendrimer synthesization of gefitinib using solvent-free technique for targeting EGFR-TK to treat Non-Small-Cell Lung Cancer (NSCLC). The inclusion complex of gefitinib with β-cyclodextrin was prepared by trituration method. This complex encapsulated G4 PAMAM dendrimers were synthesized by Michael addition and amidation reactions using green chemistry and then PEGylated by conjugation reaction. FTIR and DSC confirmed the formation of inclusion complex of gefitinib and β-cyclodextrin and PEGylation of G4 PAMAM dendrimers. Gefitinib showed higher solubility, encapsulation efficiency and controlled release profile from PEGylated dendrimers compared to inclusion complex. The PEGylated dendrimers of inclusion complex of gefitinib were found to reduce hemolytic toxicity and lesser GI 50 value on Human lung cancer cell line A-549 by effective targeting EGFR-TK. A combinatorial approach of inclusion complexation and dendrimer synthesization is one of the alternative advanced approaches to treat NSCLC. Copyright © 2017 Elsevier B.V. All rights reserved.

  10. Detoxification of tabun at physiological pH mediated by substituted β-cyclodextrin and glucose derivatives containing oxime groups.

    PubMed

    Brandhuber, Florian; Zengerle, Michael; Porwol, Luzian; Tenberken, Oliver; Thiermann, Horst; Worek, Franz; Kubik, Stefan; Reiter, Georg

    2012-12-16

    The ability of 13 β-cyclodextrin and 2 glucose derivatives containing substituents with oxime groups as nucleophilic components to accelerate the degradation of tabun at physiological pH has been evaluated. To this end, a qualitative and a quantitative enzymatic assay as well as a highly sensitive enantioselective GC-MS assay were used. In addition, an assay was developed that provided information about the mode of action of the investigated compounds. The results show that attachment of pyridinium-derived substituents with an aldoxime group in 3- or 4-position to a β-cyclodextrin ring affords active compounds mediating tabun degradation. Activities differ depending on the structure, the number, and the position of the substituent on the ring. Highest activity was observed for a β-cyclodextrin containing a 4-formylpyridinium oxime residue in 6-position of one glucose subunit, which detoxifies tabun with a half-time of 10.2 min. Comparison of the activity of this compound with that of an analog in which the cyclodextrin ring was replaced by a glucose residue demonstrated that the cyclodextrin is not necessary for activity but certainly beneficial. Finally, the results provide evidence that the mode of action of the cyclodextrin involves covalent modification of its oxime group rendering the scavenger inactive after reaction with the first tabun molecule. Copyright © 2012 Elsevier Ireland Ltd. All rights reserved.

  11. Interactions of Indole Derivatives with β-Cyclodextrin: A Quantitative Structure-Property Relationship Study

    PubMed Central

    Šoškić, Milan; Porobić, Ivana

    2016-01-01

    Retention factors for 31 indole derivatives, most of them with auxin activity, were determined by high-performance liquid chromatography, using bonded β-cyclodextrin as a stationary phase. A three-parameter QSPR (quantitative structure-property relationship) model, based on physico-chemical and structural descriptors was derived, which accounted for about 98% variations in the retention factors. The model suggests that the indole nucleus occupies the relatively apolar cavity of β-cyclodextrin while the carboxyl group of the indole -3-carboxylic acids makes hydrogen bonds with the hydroxyl groups of β-cyclodextrin. The length and flexibility of the side chain containing carboxyl group strongly affect the binding of these compounds to β-cyclodextrin. Non-acidic derivatives, unlike the indole-3-carboxylic acids, are poorly retained on the column. A reasonably well correlation was found between the retention factors of the indole-3-acetic acids and their relative binding affinities for human serum albumin, a carrier protein in the blood plasma. A less satisfactory correlation was obtained when the retention factors of the indole derivatives were compared with their affinities for auxin-binding protein 1, a plant auxin receptor. PMID:27124734

  12. Influence of chirality on vibrational and relaxational properties of (S)- and (R,S)-ibuprofen/methyl-β-cyclodextrin inclusion complexes: an INS and QENS study.

    PubMed

    Crupi, Vincenza; Guella, Graziano; Longeville, Stéphane; Majolino, Domenico; Mancini, Ines; Paciaroni, Alessandro; Rossi, Barbara; Venuti, Valentina

    2013-10-03

    In this paper, we analyze the internal picosecond dynamics of enantiomeric ((S)-) and racemic ((R,S)-) ibuprofen (IBP), when forming inclusion complexes, in solid state, with methyl-β-cyclodextrin (Me-β-CD), by inelastic and quasi elastic neutron scattering. The study was aimed at understanding, by the analysis of the vibrational and relaxational properties of the inclusion complexes also with respect to the single components, if and how the differences in the structural properties of the hydrogen bond (HB) network of (S)- and (R,S)-IBP can have influence on the complexation process triggered by "host-guest" interactions, whose detailed knowledge is retained as a prerequisite for enantiodiscrimination. From the results, a similar complexation mechanism for (S)- and (R,S)-IBP is argued, with a preferred penetration mode involving the isopropyl group of IBP.

  13. Tabun scavengers based on hydroxamic acid containing cyclodextrins.

    PubMed

    Brandhuber, Florian; Zengerle, Michael; Porwol, Luzian; Bierwisch, Anne; Koller, Marianne; Reiter, Georg; Worek, Franz; Kubik, Stefan

    2013-04-28

    Arrangement of several hydroxamic acid-derived substituents along the cavity of a cyclodextrin ring leads to compounds that detoxify tabun in TRIS-HCl buffer at physiological pH and 37.0 °C with half-times as low as 3 min.

  14. Chemical Microsensors For Detection Of Explosives And Chemical Warfare Agents

    DOEpatents

    Yang, Xiaoguang; Swanson, Basil I.

    2001-11-13

    An article of manufacture is provided including a substrate having an oxide surface layer and a layer of a cyclodextrin derivative chemically bonded to said substrate, said layer of a cyclodextrin derivative adapted for the inclusion of selected compounds, e.g., nitro-containing organic compounds, therewith. Such an article can be a chemical microsensor capable of detecting a resultant mass change from inclusion of the nitro-containing organic compound.

  15. Molecular Modeling and Physicochemical Properties of Supramolecular Complexes of Limonene with α- and β-Cyclodextrins.

    PubMed

    Dos Passos Menezes, Paula; Dos Santos, Polliana Barbosa Pereira; Dória, Grace Anne Azevedo; de Sousa, Bruna Maria Hipólito; Serafini, Mairim Russo; Nunes, Paula Santos; Quintans-Júnior, Lucindo José; de Matos, Iara Lisboa; Alves, Péricles Barreto; Bezerra, Daniel Pereira; Mendonça Júnior, Francisco Jaime Bezerra; da Silva, Gabriel Francisco; de Aquino, Thiago Mendonça; de Souza Bento, Edson; Scotti, Marcus Tullius; Scotti, Luciana; de Souza Araujo, Adriano Antunes

    2017-02-01

    This study evaluated three different methods for the formation of an inclusion complex between alpha- and beta-cyclodextrin (α- and β-CD) and limonene (LIM) with the goal of improving the physicochemical properties of limonene. The study samples were prepared through physical mixing (PM), paste complexation (PC), and slurry complexation (SC) methods in the molar ratio of 1:1 (cyclodextrin:limonene). The complexes prepared were evaluated with thermogravimetry/derivate thermogravimetry, infrared spectroscopy, X-ray diffraction, complexation efficiency through gas chromatography/mass spectrometry analyses, molecular modeling, and nuclear magnetic resonance. The results showed that the physical mixing procedure did not produce complexation, but the paste and slurry methods produced inclusion complexes, which demonstrated interactions outside of the cavity of the CDs. However, the paste obtained with β-cyclodextrin did not demonstrate complexation in the gas chromatographic technique because, after extraction, most of the limonene was either surface-adsorbed by β-cyclodextrin or volatilized during the procedure. We conclude that paste complexation and slurry complexation are effective and economic methods to improve the physicochemical character of limonene and could have important applications in pharmacological activities in terms of an increase in solubility.

  16. Inhalable Andrographolide-β-cyclodextrin Inclusion Complexes for Treatment of Staphylococcus aureus Pneumonia by Regulating Immune Responses.

    PubMed

    Zhang, Tongtong; Zhu, Lifei; Li, Miao; Hu, Yuzhen; Zhang, Erfeng; Jiang, Qingcheng; Han, Guang; Jin, Yiguang

    2017-05-01

    Bacterial pneumonia is a serious disease with high mortality if no appropriate and immediate therapy is available. Andrographolide (AG) is an anti-inflammatory agent extracted from a traditional Chinese herb andrographis paniculata. Oral AG tablets and pills are clinically applied for treatment of upper respiratory tract infections. However, the low solubility and bioavailability of AG lead to high doses and long-term therapy. Here we developed an andrographolide-β-cyclodextrin inclusion complex (AG-β-CD) for inhalation therapy of Staphylococcus aureus pneumonia. AG-β-CD was identified with X-ray diffraction and FT-IR. Surprisingly, both AG-β-CD and AG showed little in vitro anti-S. aureus activity. However, pulmonary delivery of AG, AG-β-CD, or penicillin had significant anti-S. aureus pneumonia effects. Leukocytes, neutrophils, white blood cells, total proteins, TNF-α, IL-6, NF-κB p65 expression, and bacterial colonies in the bronchoalveolar lavage fluids were detected. Pulmonary delivery of AG and AG-β-CD led to bacterial inhibition and inflammation alleviation by regulating immune responses, while penicillin only killed bacteria without significant immune regulation. Moreover, the antipneumonia activity of AG-β-CD was much higher than that of AG, probably resulting from locally accelerated AG dissolution due to β-CD inclusion. The aerodynamic diameter of AG-β-CD powders was 2.03 μm, suitable for pulmonary delivery. Inhalable AG-β-CD is a promising antibacterial and anti-inflammatory medicine for the treatment of S. aureus pneumonia by regulating immune responses, and the effect is enhanced by β-CD inclusion. AG and its formulations might be potent weapons against the resistant bacterial pneumonia due to their specific mechanism in the future.

  17. Preparation, characterization and in vivo evaluation of formulation of repaglinide with hydroxypropyl-β-cyclodextrin.

    PubMed

    Liu, Meina; Cao, Wen; Sun, Yinghua; He, Zhonggui

    2014-12-30

    The therapeutic efficacy of repaglinide (RPG) is limited by the low and variable oral bioavailability owing to its limited aqueous solubility. In our present study, the development and evaluation of inclusion complex applying hydroxypropyl-β-cyclodextrin (HP-β-CD) for the improvement of oral bioavailability of repaglinide was investigated systematically. The inclusion complex of repaglinide was prepared by lyophilization technique using drug: hydroxypropyl-β-cyclodextrin (1:15 mole). The prepared complexation was characterized by differential scanning calorimetry (DSC), X-ray diffractometry (XRD), NMR spectroscopy and evaluated by dissolution studies. The (1)H NMR was used in the structure study of repaglinide-HP-β-CD (RPG-HP-β-CD) inclusion complex. The analysis proved the higher probability of the repaglinide A-ring into the narrow rim of the β-cyclodextrin molecule. All the characterization information confirmed the formation of RPG-HP-β-CD inclusion complex. The in vivo pharmacokinetics of RPG-HP-β-CD and their physical mixture were performed in beagle dogs. For the first time, a simple, rapid, and sensitive LC-MS/MS method for determination of RPG in beagle dog plasma was developed. The Cmax and AUC0-t of RPG-HP-β-CD were 2.5 and 2 times higher than that of the physical mixture. These results suggested that the interaction of repaglinide with HP-β-CD could notably improve the dissolution rate and bioavailability of repaglinide comparing with its physical mixture. Copyright © 2014 Elsevier B.V. All rights reserved.

  18. Cyclodextrins in Food Technology and Human Nutrition: Benefits and Limitations.

    PubMed

    Fenyvesi, É; Vikmon, M; Szente, L

    2016-09-09

    Cyclodextrins are tasteless, odorless, nondigestible, noncaloric, noncariogenic saccharides, which reduce the digestion of carbohydrates and lipids. They have low glycemic index and decrease the glycemic index of the food. They are either non- or only partly digestible by the enzymes of the human gastrointestinal (GI) tract and fermented by the gut microflora. Based on these properties, cyclodextrins are dietary fibers useful for controlling the body weight and blood lipid profile. They are prebiotics, improve the intestinal microflora by selective proliferation of bifidobacteria. These antiobesity and anti-diabetic effects make them bioactive food supplements and nutraceuticals. In this review, these features are evaluated for α-, β- and γ-cyclodextrins, which are the cyclodextrin variants approved by authorities for food applications. The mechanisms behind these effects are reviewed together with the applications as solubilizers, stabilizers of dietary lipids, such as unsaturated fatty acids, phytosterols, vitamins, flavonoids, carotenoids and other nutraceuticals. The recent applications of cyclodextrins for reducing unwanted components, such as trans-fats, allergens, mycotoxins, acrylamides, bitter compounds, as well as in smart active packaging of foods are also overviewed.

  19. Sorption of Aromatic Compounds with Copolymer Sorbent Materials Containing β-Cyclodextrin.

    PubMed

    Wilson, Lee D; Mohamed, Mohamed H; Berhaut, Christopher L

    2011-08-29

    Urethane copolymer sorbent materials that incorporate β-cyclodextrin (CD) have been prepared and their sorption properties with chlorinated aromatic compounds (i.e., pentachlorophenol, 2,4-dichlorophenol and 2,4-dichlorophenoxy acetic acid) have been evaluated. The sorption properties of granular activated carbon (GAC) were similarly compared in aqueous solution at variable pH conditions. The sorbents displayed variable BET surface areas as follows: MDI-X copolymers (< 10¹ m²/g), CDI-X copolymers (< 10¹ m²/g), and granular activated carbon (GAC ~10³ m²/g). The sorption capacities for the copolymers sorbents are listed in descending order, as follows: GAC > CDI-3 copolymer ≈ MDI-3 copolymer. The sorption capacity for the aromatic adsorbates with each sorbent are listed in descending order, as follows: 2,4-dichlorophenol > 2,4-dichlorophenoxy acetic acid > pentachlorophenol. In general, the differences in the sorption properties of the copolymer sorbents with the chlorinated organics were related to the following factors: (i) surface area of the sorbent; (ii) CD content and accessibility; and (iii) and the chemical nature of the sorbent material.

  20. Sorption of Aromatic Compounds with Copolymer Sorbent Materials Containing β-Cyclodextrin

    PubMed Central

    Wilson, Lee D.; Mohamed, Mohamed H.; Berhaut, Christopher L.

    2011-01-01

    Urethane copolymer sorbent materials that incorporate β-cyclodextrin (CD) have been prepared and their sorption properties with chlorinated aromatic compounds (i.e., pentachlorophenol, 2,4-dichlorophenol and 2,4-dichlorophenoxy acetic acid) have been evaluated. The sorption properties of granular activated carbon (GAC) were similarly compared in aqueous solution at variable pH conditions. The sorbents displayed variable BET surface areas as follows: MDI-X copolymers (< 101 m2/g), CDI-X copolymers (< 101 m2/g), and granular activated carbon (GAC ~103 m2/g). The sorption capacities for the copolymers sorbents are listed in descending order, as follows: GAC > CDI-3 copolymer ≈ MDI-3 copolymer. The sorption capacity for the aromatic adsorbates with each sorbent are listed in descending order, as follows: 2,4-dichlorophenol > 2,4-dichlorophenoxy acetic acid > pentachlorophenol. In general, the differences in the sorption properties of the copolymer sorbents with the chlorinated organics were related to the following factors: (i) surface area of the sorbent; (ii) CD content and accessibility; and (iii) and the chemical nature of the sorbent material. PMID:28824156

  1. Spectrofluorimetric determination of stoichiometry and association constants of the complexes of harmane and harmine with beta-cyclodextrin and chemically modified beta-cyclodextrins.

    PubMed

    Martín, L; León, A; Olives, A I; Del Castillo, B; Martín, M A

    2003-06-13

    The association characteristics of the inclusion complexes of the beta-carboline alkaloids harmane and harmine with beta-cyclodextrin (beta-CD) and chemically modified beta-cyclodextrins such as hydroxypropyl-beta-cyclodextrin (HPbeta-CD), 2,3-di-O-methyl-beta-cyclodextrin (DMbeta-CD) and 2,3,6-tri-O-methyl-beta-cyclodextrin (TMbeta-CD) are described. The association constants vary from 112 for harmine/DMbeta-CD to 418 for harmane/HPbeta-CD. The magnitude of the interactions between the host and the guest molecules depends on the chemical and geometrical characteristics of the guest molecules and therefore the association constants vary for the different cyclodextrin complexes. The steric hindrance is higher in the case of harmine due to the presence of methoxy group on the beta-carboline ring. The association obtained for the harmane complexes is stronger than the one observed for harmine complexes except in the case of harmine/TMbeta-CD. Important differences in the association constants were observed depending on the experimental variable used in the calculations (absolute value of fluorescence intensity or the ratio between the fluorescence intensities corresponding to the neutral and cationic forms). When fluorescence intensity values were considered, the association constants were higher than when the ratio of the emission intensity for the cationic and neutral species was used. These differences are a consequence of the co-existence of acid-base equilibria in the ground and in excited states together with the complexation equilibria. The existence of a proton transfer reaction in the excited states of harmane or harmine implies the need for the experimental dialysis procedure for separation of the complexes from free harmane or harmine. Such methodology allows quantitative results for stoichiometry determinations to be obtained, which show the existence of both 1:1 and 1:2 beta-carboline alkaloid:CD complexes with different solubility properties.

  2. Preparation of olanzapine and methyl-β-cyclodextrin complexes using a single-step, organic solvent-free supercritical fluid process: An approach to enhance the solubility and dissolution properties.

    PubMed

    Rudrangi, Shashi Ravi Suman; Trivedi, Vivek; Mitchell, John C; Wicks, Stephen Richard; Alexander, Bruce David

    2015-10-15

    The purpose of this study was to evaluate a single-step, organic solvent-free supercritical fluid process for the preparation of olanzapine-methyl-β-cyclodextrin complexes with an express goal to enhance the dissolution properties of olanzapine. The complexes were prepared by supercritical carbon dioxide processing, co-evaporation, freeze drying and physical mixing. The prepared complexes were then analysed by differential scanning calorimetry, X-ray powder diffraction, scanning electron microscopy, solubility and dissolution studies. Computational molecular docking studies were performed to study the formation of molecular inclusion complexation of olanzapine with methyl-β-cyclodextrin. All the binary mixtures of olanzapine with methyl-β-cyclodextrin, except physical mixture, exhibited a faster and greater extent of drug dissolution than the drug alone. Products obtained by the supercritical carbon dioxide processing method exhibited the highest apparent drug dissolution. The characterisation by different analytical techniques suggests complete complexation or amorphisation of olanzapine and methyl-β-cyclodextrin complexes prepared by supercritical carbon dioxide processing method. Therefore, organic solvent-free supercritical carbon dioxide processing method proved to be novel and efficient for the preparation of solid inclusion complexes of olanzapine with methyl-β-cyclodextrin. The preliminary data also suggests that the complexes of olanzapine with methyl-β-cyclodextrin will lead to better therapeutic efficacy due to better solubility and dissolution properties. Copyright © 2015 Elsevier B.V. All rights reserved.

  3. Enantioseparation of dopa and related compounds by cyclodextrin-modified microemulsion electrokinetic chromatography.

    PubMed

    Borst, Claudia; Holzgrabe, Ulrike

    2008-09-19

    A chiral microemulsion electrokinetic chromatography method has been developed for the enantiomeric separation of 3,4-dihydroxyphenylalanine (dopa), its precursors phenylalanine and tyrosine, and the structurally related substance methyldopa. The separations were achieved using an oil-in-water microemulsion, which consisted of the oil-compound ethyl acetate, the surfactant sodium dodecylsulfate (SDS), the co-surfactant 1-butanol, the organic modifier propan-2-ol and 20mM phosphate buffer pH 2.5 or 2.0 as aqueous phase. For enantioseparation sulfated beta-cyclodextrin was added. The resolution of each racemate was optimized by varying the concentration of the buffer and all components of the microemulsion. Enantioseparation could be achieved for dl-dopa, dl-phenylalanine and dl-tyrosine within 13 min with a resolution of 4.3, 3.1 and 3.3, respectively, and for methyldopa in 17 min (Rs: 1.4). The established methods allowed the detection of dopa, phenylalanine, tyrosine and methyldopa with a limit at 0.5, 1.0, 0.2 and 2.0 microg/ml.

  4. Construction and Characterization of a Chitosan-Immobilized-Enzyme and β-Cyclodextrin-Included-Ferrocene-Based Electrochemical Biosensor for H2O2 Detection

    PubMed Central

    Dong, Wenbo; Wang, Kaiyin; Chen, Yu; Li, Weiping; Ye, Yanchun; Jin, Shaohua

    2017-01-01

    An electrochemical detection biosensor was prepared with the chitosan-immobilized-enzyme (CTS-CAT) and β-cyclodextrin-included-ferrocene (β-CD-FE) complex for the determination of H2O2. Ferrocene (FE) was included in β-cyclodextrin (β-CD) to increase its stability. The structure of the β-CD-FE was characterized. The inclusion amount, inclusion rate, and electrochemical properties of inclusion complexes were determined to optimize the reaction conditions for the inclusion. CTS-CAT was prepared by a step-by-step immobilization method, which overcame the disadvantages of the conventional preparation methods. The immobilization conditions were optimized to obtain the desired enzyme activity. CTS-CAT/β-CD-FE composite electrodes were prepared by compositing the CTS-CAT with the β-CD-FE complex on a glassy carbon electrode and used for the electrochemical detection of H2O2. It was found that the CTS-CAT could produce a strong reduction peak current in response to H2O2 and the β-CD-FE could amplify the current signal. The peak current exhibited a linear relationship with the H2O2 concentration in the range of 1.0 × 10−7–6.0 × 10−3 mol/L. Our work provided a novel method for the construction of electrochemical biosensors with a fast response, good stability, high sensitivity, and a wide linear response range based on the composite of chitosan and cyclodextrin. PMID:28773229

  5. Efficacy and Safety Profile of Diclofenac/Cyclodextrin and Progesterone/Cyclodextrin Formulations: A Review of the Literature Data.

    PubMed

    Scavone, Cristina; Bonagura, Angela Colomba; Fiorentino, Sonia; Cimmaruta, Daniela; Cenami, Rosina; Torella, Marco; Fossati, Tiziano; Rossi, Francesco

    2016-06-01

    According to health technology assessment, patients deserve the best medicine. The development of drugs associated with solubility enhancers, such as cyclodextrins, represents a measure taken in order to improve the management of patients. Different drugs, such as estradiol, testosterone, dexamethasone, opioids, non-steroidal anti-inflammatories (NSAIDs; i.e. diclofenac), and progesterone are associated with cyclodextrins. Products containing the association of diclofenac/cyclodextrins are available for subcutaneous, intramuscular, and intravenous administration in doses that range from 25 to 75 mg. Medicinal products containing the association of progesterone/cyclodextrins are indicated for intramuscular and subcutaneous injection at a dose equal to 25 mg. The effects of cyclodextrins have been discussed in the solubility profile and permeability through biological membranes of drug molecules. A literature search was performed in order to give an overview of the pharmacokinetic characteristics, and efficacy and safety profiles of diclofenac/hydroxypropyl-β-cyclodextrin (HPβCD) and progesterone/HPβCD associations. The results of more than 20 clinical studies were reviewed. It was suggested that the new diclofenac/HPβCD formulation gives a rapid and effective response to acute pain and, furthermore, has pharmacokinetic and efficacy/safety profiles comparable to other medicinal products not containing cyclodextrins. One of the principal aspects of these new diclofenac formulations is that in lowering the dose (lower than 50 mg) the drugs could be more tolerable, especially in patients with comorbid conditions. Moreover, results of studies investigating the characteristics of progesterone and cyclodextrins showed that the new formulation (progesterone/HPβCD 25 mg solution) has the same bioavailability as other products containing progesterone. It is more rapidly absorbed and allows the achievement of peak plasma concentrations in a shorter time. Finally, the

  6. Determining the Binding Sites of β-Cyclodextrin and Peptides by Electron-Capture Dissociation High Resolution Tandem Mass Spectrometry

    NASA Astrophysics Data System (ADS)

    Qi, Yulin; Geib, Timon; Volmer, Dietrich A.

    2015-07-01

    Cyclodextrins (CDs) are a group of cyclic oligosaccharides, which readily form inclusion complexes with hydrophobic compounds to increase bioavailability, thus making CDs ideal drug excipients. Recent studies have also shown that CDs exhibit a wide range of protective effects, preventing proteins from aggregation, degradation, and folding. These effects strongly depend on the binding sites on the protein surface. CDs only exhibit weak interactions with amino acids, however; conventional analytical techniques therefore usually fail to reveal the exact location of the binding sites. Moreover, some studies even suggest that CD inclusion complexes are merely electrostatic adducts. Here, electron capture dissociation (ECD) was applied in this proof-of-concept study to examine the exact nature of the CD/peptide complexes, and CD binding sites were unambiguously located for the first time via Fourier-transform ion cyclotron resonance (FTICR) tandem mass spectrometry.

  7. A novel multi-tiered experimental approach unfolding the mechanisms behind cyclodextrin-vitamin inclusion complexes for enhanced vitamin solubility and stability.

    PubMed

    Braithwaite, Miles C; Kumar, Pradeep; Choonara, Yahya E; du Toit, Lisa C; Tomar, Lomas K; Tyagi, Charu; Pillay, Viness

    2017-10-30

    This study was conducted to provide a mechanistic account for understanding the synthesis, characterization and solubility phenomena of vitamin complexes with cyclodextrins (CD) for enhanced solubility and stability employing experimental and in silico molecular modeling strategies. New geometric, molecular and energetic analyses were pursued to explicate experimentally derived cholecalciferol complexes. Various CD molecules (α-, β-, γ-, and hydroxypropyl β-) were complexed with three vitamins: cholecalciferol, ascorbic acid and α-tocopherol. The Inclusion Efficiency (IE%) was computed for each CD-vitamin complex. The highest IE% achieved for a cholecalciferol complex was for 'βCDD 3 -8', after utilizing a unique CD:cholecalciferol molar synthesis ratio of 2.5:1, never before reported as successful. 2HPβCD-cholecalciferol, γCD-cholecalciferol and α-tocopherol inclusion complexes (IC's) reached maximal IE% with a CD:vitamin molar ratio of 5:1. The results demonstrate that IE%, thermal stability, concentration, carrier solubility, molecular mechanics and intended release profile are key factors to consider when synthesizing vitamin-CD complexes. Phase-solubility data provided insights into the design of formulations with IC's that may provide analogous oral vitamin release profiles even when hydrophobic and hydrophilic vitamins are co-incorporated. Static lattice atomistic simulations were able to validate experimentally derived cholecalciferol IE phenomena and are invaluable parameters when approaching formulation strategies using CD's for improved solubility and efficacy of vitamins. Copyright © 2017 Elsevier B.V. All rights reserved.

  8. Cyclodextrin-enhanced degradation of toluene and p-toluic acid by Pseudomonas putida.

    PubMed Central

    Schwartz, A; Bar, R

    1995-01-01

    Degradation of an immiscible aromatic solvent, toluene, and a water-soluble aromatic compound, p-toluic acid, by a Pseudomonas putida strain in the presence of beta-cyclodextrin (beta-CD) was investigated. The ability of CDs to interact with hydrophobic organics and form inclusion compounds was exploited in this study to remove or alleviate the toxicities of substrates and consequently to enable or enhance degradation. Liquid toluene was found to be highly toxic to P. putida. However, this phase toxicity was removed when crystalline beta-CD-complexed toluene was provided as the substrate. The latter was fully degraded at a concentration of up to 10 g/liter. Degradation of toluene vapors was enhanced in the presence of beta-CD as a result of reduced molecular toxicity and facilitated absorption of the gaseous substrate. Similarly, beta-CD alleviated the inhibitory effect of p-toluic acid on P. putida. This protective effect of CD was remarkably more prominent when the microbial culture was shock loaded with an otherwise toxic dose of p-toluic acid (1.8 g/liter). PMID:7618884

  9. Influence of beta-cyclodextrin and chitosan in the formulation of a colon-specific drug delivery system.

    PubMed

    Rehman, K; Amin, M C I M; Muda, S

    2013-12-01

    The increase in diseases of the colon underscores the need to develop cost-effective site-directed therapies. We formulated a polysaccharide-based matrix system that could release ibuprofen under conditions simulating those in the colon by employing a wet granulation method. Tablets were prepared in a series of formulations containing a polysaccharide (beta-cyclodextrin and chitosan) matrix system along with ethylcellulose. We characterized physicochemical properties and performed an in vitro drug release assay in the absence and presence of digestive enzymes to assess the ability of the polysaccharides to function as a protective barrier against the upper gastrointestinal environment. Fourier transform infrared spectroscopy studies revealed no chemical interaction between ibuprofen and polysaccharides; however, spectrum analysis suggested the formation of an inclusion complex of beta-cyclodextrin with ibuprofen. The formulations contained 50% ethylcellulose and 50% beta-cyclodextrins (1:1) were proven to be the better formulation that slowly released the drug until 24 h (101.04 ± 0.65% maximum drug release in which 83.08 ± 0.89% drug was released in colonic medium) showed better drug release profiles than the formulations containing chitosan. We conclude that a beta-cyclodextrin drug carrier system may represent an effective approach for treatment of diseases of the colon. © Georg Thieme Verlag KG Stuttgart · New York.

  10. Influencing of resorption and side-effects of salicylic acid by complexing with beta-cyclodextrin.

    PubMed

    Szejtli, J; Gerlóczy, A; Sebestyén, G; Fónagy, A

    1981-04-01

    After oral administration of 14C-labelled salicylic acid and its beta-cyclodextrin complex to rats, the blood radioactivity-level increases in the first 2 h than decreases. The blood level obtained with the inclusion complex is somewhat but not significantly lower than with free acid. Since the resorption of cyclodextrin is a considerably slower process, it is very likely that the resorption of salicylic acid take place in the form of free acid after dissociation of the complex. The urinary excretion cumulative curves show that the free salicylic acid is completely excreted, while about 10% of the salicylic acid administered in the form of complex is lost. The cyclodextrin complex formation increases the pK value of all hydroxy-benzoic acids. Direct observations reveals that complex formation decreases the stomach-irritating effect of salicylic acid. The ratio of radioactivity was nearly the same in the organs of animals treated by both free salicylic and cyclodextrin complex.

  11. Gold nanoparticles interacting with β-cyclodextrin-phenylethylamine inclusion complex: a ternary system for photothermal drug release.

    PubMed

    Sierpe, Rodrigo; Lang, Erika; Jara, Paul; Guerrero, Ariel R; Chornik, Boris; Kogan, Marcelo J; Yutronic, Nicolás

    2015-07-22

    We report the synthesis of a 1:1 β-cyclodextrin-phenylethylamine (βCD-PhEA) inclusion complex (IC) and the adhesion of gold nanoparticles (AuNPs) onto microcrystals of this complex, which forms a ternary system. The formation of the IC was confirmed by powder X-ray diffraction and NMR analyses ((1)H and ROESY). The stability constant of the IC (760 M(-1)) was determined using the phase solubility method. The adhesion of AuNPs was obtained using the magnetron sputtering technique, and the presence of AuNPs was confirmed using UV-vis spectroscopy (surface plasmon resonance effect), which showed an absorbance at 533 nm. The powder X-ray diffractograms of βCD-PhEA were similar to those of the crystals decorated with AuNPs. A comparison of the one- and two-dimensional NMR spectra of the IC with and without AuNPs suggests partial displacement of the guest to the outside of the βCD due to attraction toward AuNPs, a characteristic tropism effect. The size, morphology, and distribution of the AuNPs were analyzed using TEM and SEM. The average size of the AuNPs was 14 nm. Changes in the IR and Raman spectra were attributed to the formation of the complex and to the specific interactions of this group with the AuNPs. Laser irradiation assays show that the ternary system βCD-PhEA-AuNPs in solution enables the release of the guest.

  12. Ion-exclusion chromatography with conductimetric detection of aliphatic carboxylic acids on a weakly acidic cation-exchange resin by elution with benzoic acid-beta-cyclodextrin.

    PubMed

    Tanaka, Kazuhiko; Mori, Masanobu; Xu, Qun; Helaleh, Murad I H; Ikedo, Mikaru; Taoda, Hiroshi; Hu, Wenzhi; Hasebe, Kiyoshi; Fritz, James S; Haddad, Paul R

    2003-05-16

    In this study, an aqueous solution consisting of benzoic acid with low background conductivity and beta-cyclodextrin (beta-CD) of hydrophilic nature and the inclusion effect to benzoic acid were used as eluent for the ion-exclusion chromatographic separation of aliphatic carboxylic acids with different pKa values and hydrophobicity on a polymethacrylate-based weakly acidic cation-exchange resin in the H+ form. With increasing concentration of beta-cyclodextrin in the eluent, the retention times of the carboxylic acids decreased due to the increased hydrophilicity of the polymethacrylate-based cation-exchange resin surface from the adsorption of OH groups of beta-cyclodextrin. Moreover, the eluent background conductivity decreased with increasing concentration of beta-cyclodextrin in 1 mM benzoic acid, which could result in higher sensitivity for conductimetric detection. The ion-exclusion chromatographic separation of carboxylic acids with high resolution and sensitivity was accomplished successfully by elution with a 1 mM benzoic acid-10 mM cyclodextrin solution without chemical suppression.

  13. Cyclodextrin-functionalized mesostructured silica nanoparticles for removal of polycyclic aromatic hydrocarbons.

    PubMed

    Topuz, Fuat; Uyar, Tamer

    2017-07-01

    Polycyclic aromatic hydrocarbons (PAHs) are the byproducts of the incomplete combustion of carbon-based fuels, and have high affinity towards DNA strands, ultimately exerting their carcinogenic effects. They are ubiquitousenvironmental contaminants,and can accumulate on tissues due to their lipophilic nature. In this article, we describe a novel concept for PAH removal from aqueous solutions using cyclodextrin-functionalized mesostructured silica nanoparticles (CDMSNs) and pristine mesostructured silica nanoparticles (MSNs). The adsorption applications of MSNs are greatly restricted due to the absence of surface functional groups on such particles. In this regard, cyclodextrins can serve as ideal functional molecules with their toroidal, cone-type structure, capable of inclusion-complex formation with many hydrophobic molecules, including genotoxic PAHs. The CDMSNs were synthesized by the surfactant-templated, NaOH-catalyzed condensation reactions of tetraethyl orthosilicate (TEOS) in the presence of two different types of cyclodextrin (i.e. hydroxypropyl-β-cyclodextrin (HP-β-CD) and native β-cyclodextrin (β-CD)). The physical incorporation of CD moieties was supported by XPS, FT-IR, NMR, TGA and solid-state 13 C NMR. The CDMSNs were treated with aqueous solutions of five different PAHs (e.g. pyrene, anthracene, phenanthrene, fluorene and fluoranthene). The functionalization of MSNs with cyclodextrin moieties significantly boosted the sorption capacity (q) of the MSNs up to ∼2-fold, and the q ranged between 0.3 and 1.65mg per gram CDMSNs, of which the performance was comparable to that of the activated carbon. Copyright © 2017 Elsevier Inc. All rights reserved.

  14. New Electrochemically-Modified Carbon Paste Inclusion β-Cyclodextrin and Carbon Nanotubes Sensors for Quantification of Dorzolamide Hydrochloride

    PubMed Central

    Alarfaj, Nawal Ahmad; El-Tohamy, Maha Farouk

    2016-01-01

    The present article introduces a new approach to fabricate carbon paste sensors, including carbon paste, modified carbon paste inclusion β-cyclodextrin, and carbon nanotubes for the quantification of dorzolamide hydrochloride (DRZ). This study is mainly based on the construction of three different carbon paste sensors by the incorporation of DRZ with phosphotungstic acid (PTA) to form dorzolamide-phosphotungstate (DRZ-PT) as an electroactive material in the presence of the solvent mediator ortho-nitrophenyloctyl ether (o-NPOE). The fabricated conventional carbon paste sensor (sensor I), as well as the other modified carbon paste sensors using β-cyclodextrin (sensor II) and carbon nanotubes (sensor III), have been investigated. The sensors displayed Nernstian responses of 55.4 ± 0.6, 56.4 ± 0.4 and 58.1 ± 0.2 mV·decade−1 over concentration ranges of 1.0 × 10−5–1.0 × 10−2, 1.0 × 10−6–1.0 × 10−2, and 5.0 × 10−8–1.0 × 10−2 mol·L−1 with lower detection limits of 5.0 × 10−6, 5.0 × 10−7, and 2.5 × 10−9 mol·L−1 for sensors I, II, and III, respectively. The critical performance of the developed sensors was checked with respect to the effect of various parameters, including pH, selectivity, response time, linear concentration relationship, lifespan, etc. Method validation was applied according to the international conference on harmonisation of technical requirements for registration of pharmaceuticals for human use ICH guidelines. The developed sensors were employed for the determination of DRZ in its bulk and dosage forms, as well as bio-samples. The observed data were statistically analyzed and compared with those obtained from other published methods. PMID:27918458

  15. New Electrochemically-Modified Carbon Paste Inclusion β-Cyclodextrin and Carbon Nanotubes Sensors for Quantification of Dorzolamide Hydrochloride.

    PubMed

    Alarfaj, Nawal Ahmad; El-Tohamy, Maha Farouk

    2016-12-02

    The present article introduces a new approach to fabricate carbon paste sensors, including carbon paste, modified carbon paste inclusion β-cyclodextrin, and carbon nanotubes for the quantification of dorzolamide hydrochloride (DRZ). This study is mainly based on the construction of three different carbon paste sensors by the incorporation of DRZ with phosphotungstic acid (PTA) to form dorzolamide-phosphotungstate (DRZ-PT) as an electroactive material in the presence of the solvent mediator ortho-nitrophenyloctyl ether ( o -NPOE). The fabricated conventional carbon paste sensor (sensor I), as well as the other modified carbon paste sensors using β-cyclodextrin (sensor II) and carbon nanotubes (sensor III), have been investigated. The sensors displayed Nernstian responses of 55.4 ± 0.6, 56.4 ± 0.4 and 58.1 ± 0.2 mV·decade -1 over concentration ranges of 1.0 × 10 -5 -1.0 × 10 -2 , 1.0 × 10 -6 -1.0 × 10 -2 , and 5.0 × 10 -8 -1.0 × 10 -2 mol·L -1 with lower detection limits of 5.0 × 10 -6 , 5.0 × 10 -7 , and 2.5 × 10 -9 mol·L -1 for sensors I, II, and III, respectively. The critical performance of the developed sensors was checked with respect to the effect of various parameters, including pH, selectivity, response time, linear concentration relationship, lifespan, etc. Method validation was applied according to the international conference on harmonisation of technical requirements for registration of pharmaceuticals for human use ICH guidelines. The developed sensors were employed for the determination of DRZ in its bulk and dosage forms, as well as bio-samples. The observed data were statistically analyzed and compared with those obtained from other published methods.

  16. Formulation, optimization and evaluation of curcumin-β-cyclodextrin-loaded sponge for effective drug delivery in thermal burns chemotherapy.

    PubMed

    Kaur, Navdeep; Garg, Tarun; Goyal, Amit K; Rath, Goutam

    2016-09-01

    The present study was designed to determine the role of curcumin-β-cyclodextrin-loaded sponge on burn wound healing in rats. Curcumin-β-cyclodextrin complex was prepared by the solvent evaporation encapsulation method. Molecular inclusion complex of curcumin-β-cyclodextrin was incorporated into gelatin sponge. The developed sponge was characterized for drug entrapment, drug release and morphology. The biological activity of optimized formulation was determined on burn wounds which were made on rats. The burn wound healing efficacy was analyzed through physical and histological changes observed at the wound sites. There was a significant decrease in rate of wound contraction in experimental groups then the control group. Curcumin-β-cyclodextrin-loaded sponge treated wound was found to heal in rate comparable to marketed formulation with no sign of adverse consequence. The result clearly substantiates the beneficial effects of curcumin-β-cyclodextrin-loaded sponge in the acceleration of wound healing.

  17. [Separation of gamma linolenic acid from evening primrose oil with urea inclusion--orthogonal experiment of optimizing technological parameters and observation of urea inclusion compound I].

    PubMed

    Wang, Hua; Ling, Man; Xue, Gang; Liu, Fengxia; Guo, Shuxian

    2010-05-01

    The influence on the urea inclusion compound under different conditions (allocated proportion, time of inclusion, temperature of inclusion) were studied through the orthogonal test, and theoretical reference of urea inclusion process for further optimization wound be offered. The orthogonal experiment was adopted, and microscope was used to observe the shape, aperture size of the urea inclusion compound under different technological parameters, the GC was employed to inspect the purity of GLA. The results indicated that the ratio of fatty acids and urea, inclusion of temperature, time of inclusion had great effect on urea inclusion compound. The three factors and its interactions significantly affected the purity of GLA. The results also showed that the best process was that the ratio of fatty acids and urea was 1 : 3, temperature of inclusion was--15 degrees C, time of inclusion was 24 h. Under the best condition, the purity of GLA reach up to 95.575 9%; and it is feasible to observe the shape and the amount of the urea inclusion compound to reflect and guide the urea inclusion technology.

  18. Inclusion complex from cyclodextrin-grafted hyaluronic acid and pseudo protein as biodegradable nano-delivery vehicle for gambogic acid.

    PubMed

    Ji, Ying; Shan, Shuo; He, Mingyu; Chu, Chih-Chang

    2017-10-15

    β-Cyclodextrin can form inclusion complex with a series of guest molecules including phenyl moieties, and has gained considerable popularity in the study of supramolecular nanostructure. In this study, a biodegradable nanocomplex (HA(CD)-4Phe4 nanocomplex) was developed from β-cyclodextrin grafted hyaluronic acid (HA) and phenylalanine based poly(ester amide). The phenylalanine based poly(ester amide) is a biodegradable pseudo protein which provides the encapsulation capacity for gambogic acid (GA), a naturally-derived chemotherapeutic which has been effectively employed to treat multidrug resistant tumor. The therapeutic potency of free GA is limited due to its poor solubility in water and the lack of tumor-selective toxicity. The nanocomplex carrier enhanced the solubility and availability of GA in aqueous media, and the HA component enabled the targeted delivery to tumor cells with overexpression of CD44 receptors. In the presence of hyaluronidase, the release of GA from the nanocomplex was significantly accelerated, due to the enzymatic biodegradation of the carrier. Compared to free GA, GA-loaded nanocomplex exhibited improved cytotoxicity in MDA-MB-435/MDR multidrug resistant melanoma cells, and induced enhanced level of apoptosis and mitochondrial depolarization, at low concentration of GA (1-2µM). The nanocomplex enhanced the therapeutic potency of GA, especially when diluted in physiological environment. In addition, suppressed matrix metalloproteinase activity was also detected in MDA-MB-435/MDR cells treated by GA-loaded nanocomplex, which demonstrated its potency in the inhibition of tumor metastasis. The in vitro data suggested that HA(CD)-4Phe4 nanocomplex could provide a promising alternative in the treatment of multidrug resistant tumor cells. Gambogic acid (GA), naturally derived from genus Garcinia trees, exhibited significant cytotoxic activity against multiple types of tumors with resistance to traditional chemotherapeutics. Unfortunately

  19. Novel inclusion complex of ibuprofen tromethamine with cyclodextrins: physico-chemical characterization.

    PubMed

    Al Omari, Mahmoud M; Daraghmeh, Nidal H; El-Barghouthi, Musa I; Zughul, Mohammad B; Chowdhry, Babur Z; Leharne, Stephen A; Badwan, Adnan A

    2009-10-15

    Guest-host interactions of ibuprofen tromethamine salt (Ibu.T) with native and modified cyclodextrins (CyDs) have been investigated using several techniques, namely phase solubility diagrams (PSDs), proton nuclear magnetic resonance ((1)H NMR), differential scanning calorimetry (DSC), Fourier transform infrared spectroscopy (FT-IR), X-ray powder diffractometry (XRPD), scanning-electron microscopy (SEM) and molecular mechanics (MM). From the analysis of PSD data (A(L)-type) it is concluded that the anionic tromethamine salt of ibuprofen (pK(a)=4.55) forms 1:1 soluble complexes with all CyDs investigated in buffered water at pH 7.0, while the neutral form of Ibu forms an insoluble complex with beta-CyD (B(S)-type) in buffered water at pH 2.0. Ibu.T has a lower tendency to complex with beta-CyD (K(11)=58 M(-1) at pH 7.0) compared with the neutral Ibu (K(11)=4200 M(-1)) in water. Complex formation of Ibu.T with beta-CyD (DeltaG(o)=-20.4 kJ/mol) is enthalpy driven (DeltaH(o)=-22.9 kJ/mol) and is accompanied by a small unfavorable entropy (DeltaS(o)=-8.4 J/mol K) change. (1)H NMR studies and MM computations revealed that, on complexation, the hydrophobic central benzene ring of Ibu.T and part of the isobutyl group reside within the beta-CyD cavity leaving the peripheral groups (carboxylate, tromethamine and methyl groups) located near the hydroxyl group networks at either rim of beta-CyD. PSD, (1)H NMR, DSC, FT-IR, XRPD, SEM and MM studies confirmed the formation of Ibu.T/beta-CyD inclusion complex in solution and the solid state.

  20. Effect of beta-cyclodextrin in improving the correlation between lycopene concentration and ORAC values.

    PubMed

    Bangalore, Dharmendra V; McGlynn, William; Scott, Darren D

    2005-03-23

    Lycopene, a lipophilic antioxidant, plays a crucial role in biological systems. It may play an important role in human biological systems by providing protection against cardiovascular disease and some cancers and by boosting the immune system. The oxygen radical absorbance capacity (ORAC) has been validated as an index of antioxidant activity for many hydrophilic antioxidants but not for lycopene. This study validates the ORAC assay for different concentrations of lycopene in the presence of beta-cyclodextrin, a water-solubility enhancer. Lyc-O-Mato 6% extract was used as a source of lycopene for these experiments. Lycopene was extracted according to a standard spectrophotometric assay procedure in the presence of beta-cyclodextrin at concentrations of 0, 0.4, 0.8, and 1.6%, and the antioxidant activity of lycopene was measured with the ORAC assay. Experiments were conducted in quadruplicate and statistical pooled correlations analyzed. Statistical analysis showed a very high correlation (R2 = 0.99) between ORAC and ascorbic acid concentrations, validating this method. Lycopene concentration correlated poorly with ORAC (R2 = 0.33) in the absence of beta-cyclodextrin. Correlations improved with increasing levels of beta-cyclodextrin (R2 = 0.58 and 0.91 for 0.4 and 0.8% beta-cyclodextrin, respectively). A very high beta-cyclodextrin concentration (1.6%) decreased the correlation between ORAC and lycopene concentration. Inclusion of beta-cyclodextrin in the ORAC assay improves correlation between ORAC and lycopene concentration, thus expanding the scope of the ORAC assay to include an additional fat-soluble antioxidant.

  1. Biodiesel fuel production from waste cooking oil by the inclusion complex of heteropoly acid with bridged bis-cyclodextrin.

    PubMed

    Zou, Changjun; Zhao, Pinwen; Shi, Lihong; Huang, Shaobing; Luo, Pingya

    2013-10-01

    The inclusion complex of Cs2.5H0.5PW12O40 with bridged bis-cyclodextrin (CsPW/B) is prepared as a highly efficient catalyst for the direct production of biodiesel via the transesterification of waste cooking oil. CsPW/B is characterized by X-ray diffraction, and the biodiesel is analyzed by Gas Chromatography-Mass Spectrometer. The conversion rate of waste cooking oil is up to 94.2% under the optimum experimental conditions that are methanol/oil molar ratio of 9:1, catalyst dosage of 3 wt%, temperature of 65 °C and reaction time of 180 min. The physical properties of biodiesel sample satisfy the requirement of ASTM D6751 standards. The novel CsPW/B catalyst used for the transesterification can lead to 96.9% fatty acid methyl esters and 86.5% of the biodiesel product can serve as the ideal substitute for diesel fuel, indicating its excellent potential application in biodiesel production. Copyright © 2013 Elsevier Ltd. All rights reserved.

  2. Sorption of agrochemical model compounds by sorbent materials containing beta-cyclodextrin.

    PubMed

    Wilson, Lee D; Mohamed, Mohamed H; Guo, Rui; Pratt, Dawn Y; Kwon, Jae Hyuck; Mahmud, Sarker T

    2010-04-01

    Polymeric sorbent materials that incorporate beta-cyclodextrin (CD) have been prepared and their sorption behavior toward two model agrochemical contaminant compounds, p-nitrophenol (PNP) and methyl chloride examined. The sorption of PNP was studied in aqueous solution using ultraviolet-visible (UV-Vis) spectroscopy, whereas the sorption of methyl chloride from the gas phase was studied using a Langmuir adsorption method. The sorption results for PNP in solution were compared between granular activated carbon (GAC), modified GAC, CD copolymers, and CD-based mesoporous silica hybrid materials. Nitrogen porosimetry at 77 K was used to estimate the surface area and pore structure properties of the sorbent materials. The sorbents displayed variable surface areas as follows: copolymers (36.2-157 m(2)/g), CD-silica materials (307-906 m(2)/g), surface modified GAC (657 m(2)/g), and granular activated carbon (approximately 10(3) m(2)/g). The sorption capacities for PNP and methyl chloride with the different sorbents are listed in descending order as follows: GAC > copolymers > surface modified GAC > CD-silica hybrid materials. In general, the differences in the sorption properties of the sorbents were related to the following: (i) surface area of the sorbent, (ii) CD content and accessibility, (iii) and the chemical nature of the sorbent material.

  3. Cyclodextrins and Iatrogenic Hearing Loss: New Drugs with Significant Risk

    PubMed Central

    Crumling, Mark A.; King, Kelly A.; Duncan, R. Keith

    2017-01-01

    Cyclodextrins are a family of cyclic oligosaccharides with widespread usage in medicine, industry and basic sciences owing to their ability to solubilize and stabilize guest compounds. In medicine, cyclodextrins primarily act as a complexing vehicle and consequently serve as powerful drug delivery agents. Recently, uncomplexed cyclodextrins have emerged as potent therapeutic compounds in their own right, based on their ability to sequester and mobilize cellular lipids. In particular, 2-hydroxypropyl-β-cyclodextrin (HPβCD) has garnered attention because of its cholesterol chelating properties, which appear to treat a rare neurodegenerative disorder and to promote atherosclerosis regression related to stroke and heart disease. Despite the potential health benefits, use of HPβCD has been linked to significant hearing loss in several species, including humans. Evidence in mice supports a rapid onset of hearing loss that is dose-dependent. Ototoxicity can occur following central or peripheral drug delivery, with either route resulting in the preferential loss of cochlear outer hair cells (OHCs) within hours of dosing. Inner hair cells and spiral ganglion cells are spared at doses that cause ~85% OHC loss; additionally, no other major organ systems appear adversely affected. Evidence from a first-to-human phase 1 clinical trial mirrors animal studies to a large extent, indicating rapid onset and involvement of OHCs. All patients in the trial experienced some permanent hearing loss, although a temporary loss of function can be observed acutely following drug delivery. The long-term impact of HPβCD use as a maintenance drug, and the mechanism(s) of ototoxicity, are unknown. β-cyclodextrins preferentially target membrane cholesterol, but other lipid species and proteins may be directly or indirectly involved. Moreover, as cholesterol is ubiquitous in cell membranes, it remains unclear why OHCs are preferentially susceptible to HPβCD. It is possible that HPβCD acts

  4. Nanostructures formed by cyclodextrin covered procainamide through supramolecular self assembly - Spectral and molecular modeling study

    NASA Astrophysics Data System (ADS)

    Rajendiran, N.; Mohandoss, T.; Sankaranarayanan, R. K.

    2015-02-01

    Inclusion complexation behavior of procainamide (PCA) with two cyclodextrins (α-CD and β-CD) were analyzed by absorption, fluorescence, scanning electron microscope (SEM), transmission electron microscope (TEM), Raman image, FT-IR, differential scanning colorimeter (DSC), Powder X ray diffraction (XRD) and 1H NMR. Blue shift was observed in β-CD whereas no significant spectral shift observed in α-CD. The inclusion complex formation results suggest that water molecules also present in the inside of the CD cavity. The present study revealed that the phenyl ring of the PCA drug is entrapped in the CD cavity. Cyclodextrin studies show that PCA forms 1:2 inclusion complex with α-CD and β-CD. PCA:α-CD complex form nano-sized particles (46 nm) and PCA:β-CD complex form self-assembled to micro-sized tubular structures. The shape-shifting of 2D nanosheets into 1D microtubes by simple rolling mechanism were analysed by micro-Raman and TEM images. Thermodynamic parameters (ΔH, ΔG and ΔS) of inclusion process were determined from semiempirical PM3 calculations.

  5. Evidence of formation of site-selective inclusion complexation between beta-cyclodextrin and poly(ethylene oxide)-block-poly(propylene oxide)- block-poly(ethylene oxide) copolymers.

    PubMed

    Tsai, Chi-Chun; Zhang, Wen-Bin; Wang, Chien-Lung; Van Horn, Ryan M; Graham, Matthew J; Huang, Jing; Chen, Yongming; Guo, Mingming; Cheng, Stephen Z D

    2010-05-28

    A series of inclusion complexes of poly(ethylene oxide)-block-poly(propylene oxide)-block-poly(ethylene oxide) (PEO-b-PPO-b-PEO) with beta-cyclodextrin (beta-CD) was prepared. Their formation, structure, and dynamics were investigated by solution two-dimensional rotating-frame Overhauser effect spectroscopy (2D ROESY) and one-dimensional (1D) and 2D solid-state (13)C NMR. The inclusion complexes between the PEO-b-PPO-b-PEO copolymers and the beta-CDs were formed in aqueous solution and detected by 2D ROESY. The high efficiency of cross polarization and spin diffusion experiments in (13)C solid-state NMR showed that the mobility of the PPO blocks dramatically decreases after beta-CD complexation, indicating that they are selectively incorporated onto the PPO blocks. The hydrophobic cavities of beta-CD restrict the PPO block mobility, which is evidence of the formation of inclusion complexes in the solid state. The 2D wide-line separation NMR experiments suggested that beta-CDs only thread onto the PPO blocks while forming the inclusion complexes. The stoichiometry of inclusion complexes was studied using (1)H NMR, and a 3:1 (PO unit to beta-CD) was found for all inclusion complexes, which indicated that the number of threaded beta-CDs was only dependent on the molecular weight of the PPO blocks. 1D wide angle x-ray diffraction studies demonstrated that the beta-CD in the inclusion complex formed a channel-like structure that is different from the pure beta-CD crystal structure.

  6. Evidence of formation of site-selective inclusion complexation between β-cyclodextrin and poly(ethylene oxide)-block-poly(propylene oxide)- block-poly(ethylene oxide) copolymers

    NASA Astrophysics Data System (ADS)

    Tsai, Chi-Chun; Zhang, Wen-Bin; Wang, Chien-Lung; Van Horn, Ryan M.; Graham, Matthew J.; Huang, Jing; Chen, Yongming; Guo, Mingming; Cheng, Stephen Z. D.

    2010-05-01

    A series of inclusion complexes of poly(ethylene oxide)-block-poly(propylene oxide)-block-poly(ethylene oxide) (PEO-b-PPO-b-PEO) with β-cyclodextrin (β-CD) was prepared. Their formation, structure, and dynamics were investigated by solution two-dimensional rotating-frame Overhauser effect spectroscopy (2D ROESY) and one-dimensional (1D) and 2D solid-state C13 NMR. The inclusion complexes between the PEO-b-PPO-b-PEO copolymers and the β-CDs were formed in aqueous solution and detected by 2D ROESY. The high efficiency of cross polarization and spin diffusion experiments in C13 solid-state NMR showed that the mobility of the PPO blocks dramatically decreases after β-CD complexation, indicating that they are selectively incorporated onto the PPO blocks. The hydrophobic cavities of β-CD restrict the PPO block mobility, which is evidence of the formation of inclusion complexes in the solid state. The 2D wide-line separation NMR experiments suggested that β-CDs only thread onto the PPO blocks while forming the inclusion complexes. The stoichiometry of inclusion complexes was studied using H1 NMR, and a 3:1 (PO unit to β-CD) was found for all inclusion complexes, which indicated that the number of threaded β-CDs was only dependent on the molecular weight of the PPO blocks. 1D wide angle x-ray diffraction studies demonstrated that the β-CD in the inclusion complex formed a channel-like structure that is different from the pure β-CD crystal structure.

  7. Encapsulation of the Antioxidant R-(+)-α-Lipoic Acid in Permethylated α- and β-Cyclodextrins: Thermal and X-ray Structural Characterization of the 1:1 Inclusion Complexes.

    PubMed

    Caira, Mino R; Bourne, Susan A; Mzondo, Buntubonke

    2017-05-23

    The naturally occurring compound α-lipoic acid (ALA) is implicated in manifold critical biological roles and its potent antioxidant properties and potential for treatment of various diseases have led to its widespread use as a dietary supplement. However, shortcomings of poor aqueous solubility and low thermal stability have hampered its development as a medicinal agent, prompting the use of cyclodextrins (CDs) to address these problems. The paucity of published structural data on the nature of the interactions between ALA and CDs motivated the present study, which describes the synthesis and X-ray structural elucidation of crystalline inclusion complexes between the biologically relevant R-(+)-α-lipoic acid (RALA) and the host molecules permethylated α-CD (TMA) and permethylated β-CD (TMB). Single crystal X-ray diffraction of TMA·RALA·6H₂O and TMB·RALA revealed significantly different orientations of the RALA molecule within the TMA and TMB cavities, but in both cases the guest molecule is fully encapsulated by the respective parent host molecules and residues of CD molecules of neighboring complex units. While pure RALA melted at 46-48 °C, combined thermal analysis techniques indicated that on heating the respective complexes, the release of RALA occurred at significantly higher onset temperatures, in the range 150-170 °C.

  8. Self-assembling nucleic acid delivery vehicles via linear, water-soluble, cyclodextrin-containing polymers.

    PubMed

    Davis, M E; Pun, S H; Bellocq, N C; Reineke, T M; Popielarski, S R; Mishra, S; Heidel, J D

    2004-01-01

    Non-viral (synthetic) nucleic acid delivery systems have the potential to provide for the practical application of nucleic acid-based therapeutics. We have designed and prepared a tunable, non-viral nucleic acid delivery system that self-assembles with nucleic acids and centers around a new class of polymeric materials; namely, linear, water-soluble cyclodextrin-containing polymers. The relationships between polymer structure and gene delivery are illustrated, and the roles of the cyclodextrin moieties for minimizing toxicity and forming inclusion complexes in the self-assembly processes are highlighted. This vehicle is the first example of a polymer-based gene delivery system formed entirely by self-assembly.

  9. Polymer-free nanofibers from vanillin/cyclodextrin inclusion complexes: high thermal stability, enhanced solubility and antioxidant property.

    PubMed

    Celebioglu, Asli; Kayaci-Senirmak, Fatma; İpek, Semran; Durgun, Engin; Uyar, Tamer

    2016-07-13

    Vanillin/cyclodextrin inclusion complex nanofibers (vanillin/CD-IC NFs) were successfully obtained from three modified CD types (HPβCD, HPγCD and MβCD) in three different solvent systems (water, DMF and DMAc) via an electrospinning technique without using a carrier polymeric matrix. Vanillin/CD-IC NFs with uniform and bead-free fiber morphology were successfully produced and their free-standing nanofibrous webs were obtained. The polymer-free CD/vanillin-IC-NFs allow us to accomplish a much higher vanillin loading (∼12%, w/w) when compared to electrospun polymeric nanofibers containing CD/vanillin-IC (∼5%, w/w). Vanillin has a volatile nature yet, after electrospinning, a significant amount of vanillin was preserved due to complex formation depending on the CD types. Maximum preservation of vanillin was observed for vanillin/MβCD-IC NFs which is up to ∼85% w/w, besides, a considerable amount of vanillin (∼75% w/w) was also preserved for vanillin/HPβCD-IC NFs and vanillin/HPγCD-IC NFs. Phase solubility studies suggested a 1 : 1 molar complexation tendency between guest vanillin and host CD molecules. Molecular modelling studies and experimental findings revealed that vanillin : CD complexation was strongest for MβCD when compared to HPβCD and HPγCD in vanillin/CD-IC NFs. For vanillin/CD-IC NFs, water solubility and the antioxidant property of vanillin was improved significantly owing to inclusion complexation. In brief, polymer-free vanillin/CD-IC NFs are capable of incorporating a much higher loading of vanillin and effectively preserve volatile vanillin. Hence, encapsulation of volatile active agents such as flavor, fragrance and essential oils in electrospun polymer-free CD-IC NFs may have potential for food related applications by integrating the particularly large surface area of NFs with the non-toxic nature of CD and inclusion complexation benefits, such as high temperature stability, improved water solubility and an enhanced

  10. New ethanol and propylene glycol free gel formulations containing a minoxidil-methyl-β-cyclodextrin complex as promising tools for alopecia treatment.

    PubMed

    Lopedota, Angela; Cutrignelli, Annalisa; Denora, Nunzio; Laquintana, Valentino; Lopalco, Antonio; Selva, Stefano; Ragni, Lorella; Tongiani, Serena; Franco, Massimo

    2015-05-01

    New topical totally aqueous formulations that improve the low water solubility of minoxidil and realize an adequate permeability of drug in the skin are proposed. These formulations are lacking in propylene glycol and alcohol that are the principal irritant ingredients present in minoxidil commercial solutions. In order to enhance poor water solubility of minoxidil randomly methyl-β-cyclodextrin was used, and four hydrogels such as, calcium alginate, sodium alginate, carbopol 934 and hydroxyethylcellulose were utilized to ensure a prolonged time of contact with the scalp. The inclusion complex minoxidil/methyl-β-cyclodextrin with a molar ratio 1:1 was obtained by freeze drying and evaluated by NMR, FT-IR and DSC analysis. An apparent stability constant of formed inclusion complex was calculated by phase solubility diagram and its value was 400 M(-1). The solid inclusion complex was used to prepare gel formulations with similar dose to minoxidil commercial solution. The gels were evaluated for various technological parameters including rheological behavior, in vitro drug release and ex vivo permeation through pig skin. The best performance was observed for the calcium alginate formulation.

  11. Enantiodifferentiation of chiral baclofen by β-cyclodextrin using capillary electrophoresis: A molecular modeling approach

    NASA Astrophysics Data System (ADS)

    Suliman, FakhrEldin O.; Elbashir, Abdalla A.

    2012-07-01

    Using capillary electrophoresis baclofen (BF) enantiomers were separated only in the presence of β-cyclodextrin (βCD) as a chiral selector when added to the background electrolyte. Proton nuclear magnetic resonance and electrospray ionization mass spectrometry (ESI-MS) techniques were used to determine the structure of the BF-βCD inclusion complexes. From the MS data BF was found to form a 1:1 complex with α- and βCD, while the NMR data suggest location of the aromatic ring of BF into the cyclodextrin cavity. A molecular modeling study, using the semiempirical PM6 calculations was used to investigate the mechanism of enantiodifferentiation of BF with cyclodextrins. Optimization of the structures of the complexes by PM6 method indicated that separation is obtained in the presence of β-CD due to a large binding energy difference (ΔΔE) of 46.8 kJ mol-1 between S-BF-βCD and R-BF-βCD complexes. In the case of αCD complexes ΔΔE was 1.3 kJ mol-1 indicating poor resolution between the two enantiomers. Furthermore, molecular dynamic simulations show that the formation of more stable S-BF-βCD complex compared to R-BF-β-CD complex is primarily due to differences in intermolecular hydrogen bonding.

  12. Visible Light-Cured Glycol Chitosan Hydrogel Containing a Beta-Cyclodextrin-Curcumin Inclusion Complex Improves Wound Healing In Vivo.

    PubMed

    Yoon, Sun-Jung; Hyun, Hoon; Lee, Deok-Won; Yang, Dae Hyeok

    2017-09-10

    Scarless wound healing is ideal for patients suffering from soft tissue defects. In this study, we prepared a novel wet dressing (β-CD-ic-CUR/GC) based on the visible light-cured glycol chitosan (GC) hydrogel and inclusion complex between beta-cyclodextrin (β-CD) and curcumin (CUR). We also evaluated its efficacy in the acceleration of wound healing as compared to that of CUR-loaded GC (CUR/GC). The conjugation of glycidyl methacrylate (GM) to GC for photo-curing was confirmed by ¹H-NMR measurement, and the photo-cured GC hydrogel was characterized by the analyses of rheology, swelling ratio, SEM and degradation rate. After visible light irradiation, the surface/cross-sectional morphologies and storage (G')/loss (G'') moduli revealed the formation of hydrogel with interconnected porosity. The dressing β-CD-ic-CUR/GC exhibited a controlled release of 90% CUR in a sustained manner for 30 days. On the other hand, CUR/GC showed CUR release of 16%. β-CD acted as an excipient in improving the water-solubility of CUR and affected the release behavior of CUR. The in vivo animal tests including measurement of the remaining unhealed wound area and histological analyses showed that β-CD-ic-CUR/GC may have potential as a wet dressing agent to enhance soft tissue recovery in open fractures.

  13. Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

    PubMed Central

    Nardello-Rataj, Véronique

    2014-01-01

    Summary Host–guest chemistry is useful for the construction of nanosized objects. Some of the widely used hosts are probably the cyclodextrins (CDs). CDs can form water-soluble complexes with numerous hydrophobic compounds. They have been widespread used in medicine, drug delivery and are of interest for the biocides encapsulation. Indeed, this enables the development of more or less complex systems that release antimicrobial agents with time. In this paper, the general features of CDs and their applications in the field of biocides have been reviewed. As the key point is the formation of biocide–CD inclusion complexes, this review deals with this in depth and the advantages of biocide encapsulation are highlighted throughout several examples from the literature. Finally, some future directions of investigation have been proposed. We hope that scientists studying biocide applications receive inspiration from this review to exploit the opportunities offered by CDs in their respective research areas. PMID:25550722

  14. Signal enhancement of carboxylic acids by inclusion with β-cyclodextrin in negative high-voltage-assisted laser desorption ionization mass spectrometry.

    PubMed

    Ren, Xinxin; Liu, Jia; Zhang, Chengsen; Sun, Jiamu; Luo, Hai

    2014-01-15

    It is difficult to directly analyze carboxylic acids in complex mixtures by ambient high-voltage-assisted laser desorption ionization mass spectrometry (HALDI-MS) in negative ion mode due to the low ionization efficiency of carboxylic acids. A method for the rapid detection of carboxylic acids in negative HALDI-MS has been developed based on their inclusion with β-cyclodextrin (β-CD). The negative HALDI-MS signal-to-noise ratios (S/Ns) of aliphatic, aromatic and hetero atom-containing carboxylic acids can all be significantly improved by forming 1:1 complexes with β-CD. These complexes are mainly formed by specific inclusion interactions which are verified by their collision-induced dissociation behaviors in comparison with that of their corresponding maltoheptaose complexes. A HALDI-MS/MS method has been successfully developed for the detection of α-lipoic acid in complex cosmetics and ibuprofen in a viscous drug suspension. The negative HALDI-MS S/Ns of carboxylic acids can be improved up to 30 times via forming non-covalent complexes with β-CD. The developed method shows the advantages of being rapid and simple, and is promising for rapid detection of active ingredients in complex samples or fast screening of drugs and cosmetics. Copyright © 2013 John Wiley & Sons, Ltd.

  15. Evaluation of the potential toxicity of unmodified and modified cyclodextrins on murine blood-brain barrier endothelial cells.

    PubMed

    Shityakov, Sergey; Salmas, Ramin Ekhteiari; Salvador, Ellaine; Roewer, Norbert; Broscheit, Jens; Förster, Carola

    2016-04-01

    In this study, we investigated the cytotoxic effects of unmodified α-cyclodextrin (α-CD) and modified cyclodextrins, including trimethyl-β-cyclodextrin (TRIMEB) and hydroxypropyl-β-cyclodextrin (HPβCD), on immortalized murine microvascular endothelial (cEND) cells of the blood-brain barrier (BBB). A CellTiter-Glo viability test, performed on the cEND cells showed significant differences among the different cyclodextrins. After 24 hr of incubation, TRIMEB was the most cytotoxic, and HPβCD was non-toxic. α-CD and TRIMEB exhibited greater cytotoxicity in the Dulbecco's modified Eagle's medium than in heat-inactivated human serum indicating protective properties of the human serum. The predicted dynamic toxicity profiles (Td) for α-CD and TRIMEB indicated higher cytotoxicity for these cyclodextrins compared to the reference compound (dimethylsulfoxide). Molecular dynamics simulation of cholesterol binding to the CDs suggested that not just cholesterol but phospholipids extraction might be involved in the cytotoxicity. Overall, the results demonstrate that HPβCD has the potential to be used as a candidate for drug delivery vector development and signify a correlation between the in vitro cytotoxic effect and cholesterol binding of cyclodextrins.

  16. Preparation, Characterization, and Pharmacological Activity of Cymbopogon winterianus Jowitt ex Bor (Poaceae) Leaf Essential Oil of β-Cyclodextrin Inclusion Complexes

    PubMed Central

    Santos, Priscila L.; Araújo, Adriano A. S.; Quintans, Jullyana S. S.; Oliveira, Makson G. B.; Brito, Renan G.; Serafini, Mairim R.; Menezes, Paula P.; Santos, Marcio R. V.; Alves, Pericles B.; de Lucca Júnior, Waldecy; Blank, Arie F.; La Rocca, Viviana; Almeida, Reinaldo N.; Quintans-Júnior, Lucindo J.

    2015-01-01

    This study aimed to evaluate the orofacial antinociceptive effect of the Cymbopogon winterianus essential oil (LEO) complexed in β-cyclodextrin (LEO-CD) and to assess the possible involvement of the central nervous system (CNS). The LEO was extracted, chromatographed, and complexed in β-cyclodextrin. The complex was characterized by differential scanning calorimetry (DSC) and thermogravimetry derivative (TG/DTG). Male Swiss mice (2-3 months) were treated with LEO-CD (50–200 mg/kg, p.o.), vehicle (distilled water, p.o.), or standard drug (i.p.) and subjected to the orofacial nociception formalin-, capsaicin-, and glutamate-induced. After the formalin test, the animals were perfused and the brains subjected to immunofluorescence for Fos. The rota-rod test (7 rpm/min) was carried out. Geraniol (37.57%) was the main compound of LEO. DSC and TG/DTG proved the complexation. The orofacial nociceptive behavior was significantly (p < 0.05) reduced. The number of Fos-positive cells was significantly changed in the dorsal raphe nucleus (p < 0.01), locus coeruleus (p < 0.001), trigeminal nucleus (p < 0.05), and trigeminal thalamic tract (p < 0.05). LEO-CD did not cause changes in motor coordination in the rota-rod test. Thus, our results suggested that LEO-CD has an orofacial antinociceptive profile, probably mediated by the activation of the CNS without changing the motor coordination. PMID:26246838

  17. Efficient photosensitized splitting of the thymine dimer/oxetane unit on its modifying beta-cyclodextrin by a binding electron donor.

    PubMed

    Tang, Wen-Jian; Song, Qin-Hua; Wang, Hong-Bo; Yu, Jing-Yu; Guo, Qing-Xiang

    2006-07-07

    Two modified beta-cyclodextrins (beta-CDs) with a thymine dimer and a thymine oxetane adduct respectively, TD-CD and Ox-CD, have been prepared, and utilized to bind an electron-rich chromophore, indole or N,N-dimethylaniline (DMA), to form a supramolecular complex. We have examined the photosensitized splitting of the dimer/oxetane unit in TD-CD/Ox-CD by indole or DMA via an electron-transfer pathway, and observed high splitting efficiencies of the dimer/oxetane unit. On the basis of measurements of fluorescence spectra and splitting quantum yields, it is suggested that the splitting reaction occurs in a supramolecular complex by an inclusion interaction between the modified beta-CDs and DMA or indole. The back electron transfer, which leads low splitting efficiencies for the covalently-linked chromophore-dimer/oxetane compounds, is suppressed in the non-covalently-bound complex, and the mechanism has been discussed.

  18. Design, characterization and comparison of materials based on β and γ cyclodextrin covalently connected to microporous silica for environmental analysis.

    PubMed

    Belenguer-Sapiña, Carolina; Pellicer-Castell, Enric; El Haskouri, Jamal; Guillem, Carmen; Simó-Alfonso, Ernesto Francisco; Amorós, Pedro; Mauri-Aucejo, Adela

    2018-08-17

    Determination of organic pollutants in environmental samples presents great difficulties due to the lack of sensitivity and selectivity in many of the existing analytical methods. In this work, the efficiency of materials based on silica structures containing bounded γ-cyclodextrin has been evaluated to determinate phenolic compounds and polycyclic aromatic hydrocarbons in air and water samples, respectively, in comparison with materials made of β-cyclodextrin. According to the results obtained for the material characterization, the new γ-cyclodextrin solid phase does not apparently present any porosity when used in air samples, but it has been shown to work efficiently for the preconcentration of polycyclic aromatic hydrocarbons in water, with recoveries around 80%. In addition, the use of the β-cyclodextrin material for phenolic compounds sampling can be highlighted with recoveries between 83% and 95%, and recoveries for 4-vinylphenol and 2-methoxy-4-vinylphenol have been especially improved in comparison with the use of materials containing trapped β-cyclodextrin in our previous researches. The observed phenomena can be explained on the basis of the analyte molecules size and the diameter of the cyclodextrin cavities, the influence of the cyclodextrin type in the material structure as well as on the interactions taking place with the pollutants and the influence of the matrix type in the retention and desorption mechanisms. Copyright © 2018 Elsevier B.V. All rights reserved.

  19. The influence of cyclomaltooligosaccharides (cyclodextrins) on the enzymatic decomposition of l-phenylalanine catalyzed by phenylalanine ammonia-lyase.

    PubMed

    Gubica, Tomasz; Pełka, Agnieszka; Pałka, Katarzyna; Temeriusz, Andrzej; Kańska, Marianna

    2011-09-27

    Cyclomaltohexaose (α-cyclodextrin) and cyclomaltoheptaose (β-cyclodextrin) as well as their four methyl ether derivatives, that is, hexakis(2,3-di-O-methyl)cyclomaltohexaose, hexakis(2,3,6-tri-O-methyl)cyclomaltohexaose, heptakis(2,3-di-O-methyl)cyclomaltoheptaose, and heptakis(2,3,6-tri-O-methyl)cyclomaltoheptaose were investigated as the additives in the course of enzymatic decomposition of l-phenylalanine catalyzed by phenylalanine ammonia-lyase. Only a few of those additives behaved like classical inhibitors of the enzymatic reaction under investigation because the values of the Michaelis constants that were obtained, as well as the maximum velocity values depended mostly atypically on the concentrations of those additives. In most cases cyclodextrins caused mixed inhibition, both competitive and noncompetitive, but they also acted as activators for selected concentrations. This atypical behaviour of cyclodextrins is caused by three different and independent effects. The inhibitory effect of cyclodextrins is connected with the decrease of substrate concentration and unfavourable influence on the flexibility of the enzyme molecules. On the other hand, the activating effect is connected with the decrease of product concentration (the product is an inhibitor of the enzymatic reaction under investigation). All these effects are caused by the ability of the cyclodextrins to form inclusion complexes. Copyright © 2011 Elsevier Ltd. All rights reserved.

  20. Controlled release of chlorhexidine digluconate using β-cyclodextrin and microfibrillated cellulose.

    PubMed

    Lavoine, Nathalie; Tabary, Nicolas; Desloges, Isabelle; Martel, Bernard; Bras, Julien

    2014-09-01

    This study aims to develop a high-performance delivery system using microfibrillated cellulose (MFC)-coated papers as a controlled release system combined with the well-known drug delivery agent, β-cyclodextrin (βCD). Chlorhexidine digluconate (CHX), an antibacterial molecule, was mixed with a suspension of MFC or a βCD solution or mixed with both the substances, before coating onto a cellulosic substrate. The intermittent diffusion of CHX (i.e., diffusion interrupted by the renewal of the release medium periodically) was conducted in an aqueous medium, and the release mechanism of CHX was elucidated by field emission gun-scanning electron microscopy, SEM, NMR, and Fourier transform infrared analyses. According to the literature, both βCD and MFC are efficient controlled delivery systems. This study indicated that βCD releases CHX more gradually and over a longer period of time compared to MFC, which is mainly due to the ability of βCD to form an inclusion complex with CHX. Furthermore from the release study, a complementary action when the two compounds were combined was deduced. MFC mainly affected the burst effect, while βCD primarily controlled the amount of CHX released over time. In this paper, two different types of controlled release systems are proposed and compared. Depending on the final application, the use of βCD alone would release low amounts of active molecules over time (slow delivery), whereas the combination of β-cyclodextrin and MFC would be more suitable for the release of higher amounts of active molecules over time (rapid delivery). Copyright © 2014 Elsevier B.V. All rights reserved.

  1. Computer-aided molecular modeling techniques for predicting the stability of drug cyclodextrin inclusion complexes in aqueous solutions

    NASA Astrophysics Data System (ADS)

    Faucci, Maria Teresa; Melani, Fabrizio; Mura, Paola

    2002-06-01

    Molecular modeling was used to investigate factors influencing complex formation between cyclodextrins and guest molecules and predict their stability through a theoretical model based on the search for a correlation between experimental stability constants ( Ks) and some theoretical parameters describing complexation (docking energy, host-guest contact surfaces, intermolecular interaction fields) calculated from complex structures at a minimum conformational energy, obtained through stochastic methods based on molecular dynamic simulations. Naproxen, ibuprofen, ketoprofen and ibuproxam were used as model drug molecules. Multiple Regression Analysis allowed identification of the significant factors for the complex stability. A mathematical model ( r=0.897) related log Ks with complex docking energy and lipophilic molecular fields of cyclodextrin and drug.

  2. Bioengineering of a cellulosic fabric for insecticide delivery via grafted cyclodextrin.

    PubMed

    Romi, Roberto; Lo Nostro, Pierandrea; Bocci, Eugenio; Ridi, Francesca; Baglioni, Piero

    2005-01-01

    beta-Cyclodextrin (beta-CD) can be easily grafted onto cellulosic textiles through covalent bonds. In such a way beta-CD empty cavities provide an efficient tool for entrapping different kinds of hydrophobic molecules on the surface of the fabric and releasing them slowly in time. The capability of cyclodextrins to include hydrophobic molecules such as fragrances, antimicrobial agents, and other chemicals can be then exploited to produce new grafted textiles with peculiar and useful performances. In this work we report the inclusion of two different products, the pyrethroid insecticide permethrin (PERM) and the insect repellent N,N-diethyl-m-toluamide (DEET), into beta-CD molecules grafted on cotton fabric. UV-vis spectrophotometry and thermal analysis confirmed the presence of the guest molecules on the fabric surface. Bioassays were carried out on two mosquito species of medical importance, Aedes aegypti and Anopheles stephensi; knock down effect and mortality were measured using standard World Health Organization (WHO) cone tests. Repellency and irritancy (blood feeding inhibition) were also measured using cage tests and a baited tunnel device. PERM-treated fabrics kept the insecticidal/irritant efficacy even for a long time after the treatment, whereas DEET activity lasted more shortly.

  3. Physico-chemical characterization and antibacterial activity of inclusion complexes of Hyptis martiusii Benth essential oil in β-cyclodextrin.

    PubMed

    Andrade, Tatianny A; Freitas, Thiago S; Araújo, Francielly O; Menezes, Paula P; Dória, Grace Anne A; Rabelo, Alessandra S; Quintans-Júnior, Lucindo J; Santos, Márcio R V; Bezerra, Daniel P; Serafini, Mairim R; Menezes, Irwin Rose A; Nunes, Paula Santos; Araújo, Adriano A S; Costa, Maria S; Campina, Fábia F; Santos, Antonia T L; Silva, Ana R P; Coutinho, Henrique D M

    2017-05-01

    Cyclodextrins (CDs) have been used as important pharmaceutical excipients for improve the physicochemical properties of the drugs of low solubility as the essential oil of Hyptis martiusii. This oil is important therapeutically, but the low solubility and bioavailability compromises your use. Therein, the aim of this study was to obtain and to characterize physico-chemically the samples obtained by physical mixture (PM), paste complexation (PC) and slurry complexation (SC) of the essential oil Hyptis martiusii (EOHM) in β-CD, and to compare the antibacterial and modulatory-antibiotic activity of products obtained and oil free. The physicochemical characterization was performed by differential scanning calorimetry (DSC), thermogravimetry/derivative thermogravimetry (TG/DTG), scanning electron microscopy (SEM), X-ray diffraction (XRD) and Karl Fischer titration. Additionally, the antibacterial tests were performed by microdilution technique. Thus, it was observed that the PM method showed low complexing capacity, unlike PC and SC in which it was observed the formation of inclusion complexes. In addition, the second stage of the TG/DTG curves showed that SC was the best method inclusion with mass loss of 6.9% over the PC that was 6.0%. The XRD results corroborate with the results above suggesting the formation of new solid phase and the SEM photomicrographs showed the porous surface of the samples PC and SC. The essential oil alone demonstrated an antibacterial and modulatory effect against the S. aureus and the Gram negative strain, respectively. However, the β-CD and the inclusion complex did not demonstrate any biological activity in the performed antibacterial assays. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

  4. Molecular inclusion complex of curcumin-β-cyclodextrin nanoparticle to enhance curcumin skin permeability from hydrophilic matrix gel.

    PubMed

    Rachmawati, Heni; Edityaningrum, Citra Ariani; Mauludin, Rachmat

    2013-12-01

    Curcumin (CUR) has various pharmacological effects, but its extensive first-pass metabolism and short elimination half-life limit its bioavailability. Therefore, transdermal application has become a potential alternative to delivery CUR. To increase CUR solubility for the development of a transparent homogenous gel and also enhance the permeation rate of CUR into the skin, β-cyclodextrin-curcumin nanoparticle complex (BCD-CUR-N) was developed. CUR encapsulation efficiency was increased by raising the percentage of CUR to BCD up to 20%. The mean particle size of the best CUR loading formula was 156 nm. All evaluation data using infrared spectroscopy, Raman spectroscopy, powder X-ray diffractometry, differential thermal analysis and scanning electron microscopy confirmed the successful formation of the inclusion complex. BCD-CUR-N increased the CUR dissolution rate of 10-fold (p < 0.01). In addition, the improvement of CUR permeability acrossed skin model tissue was observed in gel containing the BCD-CUR-N and was about 1.8-fold when compared with the free CUR gel (p < 0.01). Overall, CUR in the form of the BCD-CUR-N improved the solubility further on the penetration of CUR.

  5. Preparation and Physicochemical Characterization of an Inclusion Complex Between Dimethylated β-Cyclodextrin and a Drug Lead From a New Class of Orally Active Antimalarial 3,5-Diaryl-2-Aminopyridines.

    PubMed

    Joseph, Laurelle M; Chibale, Kelly; Caira, Mino R

    2016-11-01

    Cyclodextrins (CDs) were used to increase the aqueous solubility of a recently discovered orally active 3,5-diaryl-2-aminopyridine antimalarial drug lead (MMP). Phase-solubility studies using β-CD, hydroxypropyl-β-CD, and heptakis(2,6-di-O-methyl)-β-CD (DIMEB) as potential solubilizers for MMP yielded solubility enhancement factors of 17, 49, and 65, respectively, at 25°C with CD concentrations ∼20 mM. A crystalline complex, DIMEB⋅MMP⋅2H 2 O, was prepared and characterized by thermal and single-crystal X-ray analyses. The latter technique revealed preferential encapsulation of the hydrophobic methylsulfonylphenyl moiety of MMP within the CD cavity and protrusion of the more polar methoxypyridinyl and aminopyridine residues from the cavity. This inclusion mode results in a DIMEB complex with a new packing arrangement and an intricate network of intermolecular hydrogen bonds linking guest residues that protrude from 2 1 -related host cavities. A summary of the results of the performance of the inclusion complex in preliminary pharmacokinetic and efficacy tests in mouse models is provided. Copyright © 2016 American Pharmacists Association®. Published by Elsevier Inc. All rights reserved.

  6. Inclusion complex and nanoclusters of cyclodextrin to increase the solubility and efficacy of albendazole.

    PubMed

    Pacheco, P A; Rodrigues, L N C; Ferreira, J F S; Gomes, A C P; Veríssimo, C J; Louvandini, H; Costa, R L D; Katiki, L M

    2018-03-01

    Albendazole (ABZ), a benzimidazole widely used to control gastrointestinal parasites, is poorly soluble in water, resulting in variable and incomplete bioavailability. This has favored the appearance ABZ-resistant nematodes and, consequently, an increase in its clinical ineffectiveness. Among the pharmaceutical techniques developed to increase drug efficacy, cyclodextrins (CDs) and other polymers have been extensively used with water-insoluble pharmaceutical drugs to increase their solubility and availability. Our objective was to prepare ABZ formulations, including β-cyclodextrin (βCD) or hydroxypropyl-β-cyclodextrin (HPβCD), associated or not to the water-soluble polymer polyvinylpyrrolidone (PVP). These formulations had their solubility and anthelmintic effect both evaluated in vitro. Also, their anthelmintic efficacy was evaluated in lambs naturally infected with gastrointestinal nematodes (GIN) through the fecal egg count (FEC) reduction test. In vitro, the complex ABZ/HPβCD had higher solubility than ABZ/βCD. The addition of PVP to the complexes increased solubility and dissolution rates more effectively for ABZ/HPβCD than for ABZ/βCD. In vivo, 48 lambs naturally infected with GIN were divided into six experimental groups: control, ABZ, ABZ/βCD, ABZ/βCD-PVP, ABZ/HPβCD, and ABZ/HPβCD-PVP. Each treated animal received 10 mg/kg of body weight (based on the ABZ dose) for three consecutive days. After 10 days of the last administered dose, treatment efficacy was calculated. The efficacy values were as follows: ABZ (70.33%), ABZ/βCD (85.33%), ABZ/βCD-PVP (82.86%), ABZ/HPβCD (78.37%), and ABZ/HPβCD-PVP (43.79%). In vitro, ABZ/HPβCD and ABZ/HPβCD-PVP had high solubility and dissolution rates. In vivo, although the efficacies of ABZ/βCD, ABZ/βCD-PVP, and ABZ/HPβCD increased slightly when compared to pure ABZ, this increase was not significant (P > 0.05).

  7. Ibuprofen-in-cyclodextrin-in-W/O/W emulsion - Improving the initial and long-term encapsulation efficiency of a model active ingredient.

    PubMed

    Hattrem, Magnus N; Kristiansen, Kåre A; Aachmann, Finn L; Dille, Morten J; Draget, Kurt I

    2015-06-20

    A challenge in formulating water-in-oil-in-water (W/O/W) emulsions is the uncontrolled release of the encapsulated compound prior to application. Pharmaceuticals and nutraceuticals usually have amphipathic nature, which may contribute to leakage of the active ingredient. In the present study, cyclodextrins (CyDs) were used to impart a change in the relative polarity and size of a model compound (ibuprofen) by the formation of inclusion complexes. Various inclusion complexes (2-hydroxypropyl (HP)-β-CyD-, α-CyD- and γ-CyD-ibuprofen) were prepared and presented within W/O/W emulsions, and the initial and long-term encapsulation efficiency was investigated. HP-β-CyD-ibuprofen provided the highest encapsulation of ibuprofen in comparison to a W/O/W emulsion with unassociated ibuprofen confined within the inner water phase, with a four-fold increase in the encapsulation efficiency. An improved, although lower, encapsulation efficiency was obtained for the inclusion complex γ-CyD-ibuprofen in comparison to HP-β-CyD-ibuprofen, whereas α-CyD-ibuprofen had a similar encapsulation efficiency to that of unassociated ibuprofen. The lower encapsulation efficiency of ibuprofen in combination with α-CyD and γ-CyD was attributed to a lower association constant for the γ-CyD-ibuprofen inclusion complex and the ability of α-CyD to form inclusion complexes with fatty acids. For the W/O/W emulsion prepared with HP-β-CyD-ibuprofen, the highest encapsulation of ibuprofen was obtained at hyper- and iso-osmotic conditions and by using an excess molar ratio of CyD to ibuprofen. In the last part of the study, it was suggested that the chemical modification of the HP-β-CyD molecule did not influence the encapsulation of ibuprofen, as a similar encapsulation efficiency was obtained for an inclusion complex prepared with mono-1-glucose-β-CyD. Copyright © 2015 Elsevier B.V. All rights reserved.

  8. Molecular insight into the inclusion of the dietary plant flavonol fisetin and its chromophore within a chemically modified γ-cyclodextrin: Multi-spectroscopic, molecular docking and solubility studies.

    PubMed

    Pahari, Biswapathik; Chakraborty, Sandipan; Sengupta, Pradeep K

    2018-09-15

    We explored the encapsulation of dietary plant flavonols fisetin and its chromophore 3-hydroxyflavone, within 2-hydroxypropyl-γ-cyclodextrin (HPγ-CDx) nano-cavity in aqueous solution using multi-spectroscopic approaches and molecular docking. Upon addition of HPγ-CDx, dramatic changes occur in the intrinsic 'two color' fluorescence behavior of the fluorophores. This is manifested by significant increase in the steady state fluorescence intensities, anisotropies, average fluorescence lifetimes and rotational correlation times. Furthermore, in the CDx environment, intrinsically achiral flavonols exhibit prominent induced circular dichroism bands. These findings indicate that the flavonol molecules spontaneously enter the relatively hydrophobic, chiral environment of the HPγ-CDx nano-cavities. Molecular docking computations corroborate the spectroscopic findings, and predict selectivity in orientation of the encapsulated flavonols. HPγ-CDx inclusion increases the aqueous solubility of individual flavonols ∼100-1000 times. The present study demonstrates that the hydroxypropyl substituent in γ-CDx controls the inclusion mode of the flavonols, leading to their enhanced solubilization and altered spectral signatures. Copyright © 2018 Elsevier Ltd. All rights reserved.

  9. Comparative study of the complex forming ability and enantioselectivity of cyclodextrin polymers by CE and 1H NMR.

    PubMed

    Danel, Cécile; Azaroual, Nathalie; Chavaria, Cédric; Odou, Pascal; Martel, Bernard; Vaccher, Claude

    2013-02-15

    The interactions between nine drugs (baclofen, bupivacaine, chlorpheniramine, ketoconazole, paliperidone, promethazine, propranolol, risperidone and verapamil) and six cyclodextrins (α-CD, β-CD, γ-CD, HP-β-CD, HP-γ-CD and Me-β-CD) or six polymers of cyclodextrins (polyα-CD, polyβ-CD, polyγ-CD, polyHP-β-CD, polyHP-γ-CD and polyMe-β-CD) were studied by affinity capillary electrophoresis and/or (1)H NMR at pH 2.5. An exhaustive qualitative study was performed through the determination of the retardation factor. Then, four compounds and both β-CD and polyβ-CD were selected for the quantitative study of the interactions at pH 2.5 and 7.0. By comparing the results obtained with the β-CD and polyβ-CD, it appears that the apparent binding constants are up to five times higher with the polymer. The 2D-NMR results seem to indicate that the structure of the polymeric network favours the inclusion of the guest in the hydrophobic cavity of the CD units. Moreover, the poly-CDs have shown very high enantioselective abilities at both pH. Copyright © 2012 Elsevier Ltd. All rights reserved.

  10. Temperature Dependence of Positron Annihilation in beta-Cyclodextrin and beta-Cyclodextrin Complexes

    NASA Astrophysics Data System (ADS)

    Hu, Y.; Hsu Hadley, F. H., Jr.; Trinh, T.

    1996-11-01

    The effects of temperature on positron annihilation in beta-cyclodextrin and beta-cyclodextrin complexed with benzyl salicylate, benzyl acetate, ethyl salicylate, geraniol, linalool and nerol were studied. Samples were prepared by slurry, air-dried and freeze-dried methods. Lifetime spectra were measured as a function of temperature for each sample. Comparison of the annihilation rate and intensity of the longer-lived component showed that positronium formation was affected by guest molecules, preparation methods and temperature variations. Results can be used to explain beta-cyclodextrin complex formation with different guest molecules.

  11. Tuning the constrained photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline inside the cyclodextrin nanocavities: A detailed insight via experimental and theoretical approach

    NASA Astrophysics Data System (ADS)

    Varghese, Beena; Al-Busafi, Saleh N.; Suliman, FakhrEldin O.; Al-Kindy, Salma M. Z.

    2017-02-01

    The modulation in the photophysics of a pyrazoline dye 3-naphthyl-1-phenyl-5-(4-carboxyphenyl)-2-pyrazoline (NPCP), when it drifts from bulk water into the nanocages of aqueous cyclodextrin solutions was investigated. The intramolecular charge transfer (ICT) fluorescence band intensity was found to increase with a blue shift in the presence of cyclodextrins. The results from 1H NMR and 1Hsbnd H COSY NMR spectral analysis clearly points out the position of pyrazoline ring inside the cavity and its role in complexation process. A quantitative assessment of the emission intensity data on Benesi-Hildebrand (B-H) equation along with ESI-MS spectra reveals the probable stoichiometry of NPCP-CD complexes. Molecular docking and molecular dynamics studies were conducted for β/γ cyclodextrin associated inclusion complexes of NPCP. The results obtained by computational studies are in good relation with the data obtained through experimental methods and both ascertain the encapsulation of NPCP into cyclodextrins.

  12. Fabrication of electrospun polylactic acid nanofilm incorporating cinnamon essential oil/β-cyclodextrin inclusion complex for antimicrobial packaging.

    PubMed

    Wen, Peng; Zhu, Ding-He; Feng, Kun; Liu, Fang-Jun; Lou, Wen-Yong; Li, Ning; Zong, Min-Hua; Wu, Hong

    2016-04-01

    A novel antimicrobial packaging material was obtained by incorporating cinnamon essential oil/β-cyclodextrin inclusion complex (CEO/β-CD-IC) into polylacticacid (PLA) nanofibers via electrospinning technique. The CEO/β-CD-IC was prepared by the co-precipitation method and SEM and FT-IR spectroscopy analysis indicated the successful formation of CEO/β-CD-IC, which improved the thermal stability of CEO. The CEO/β-CD-IC was then incorporated into PLA nanofibers by electrospinning and the resulting PLA/CEO/β-CD nanofilm showed better antimicrobial activity compared to PLA/CEO nanofilm. The minimum inhibitory concentration (MIC) of PLA/CEO/β-CD nanofilm against Escherichia coli and Staphylococcus aureus was approximately 1 mg/ml (corresponding CEO concentration 11.35 μg/ml) and minimum bactericidal concentration (MBC) was approximately 7 mg/ml (corresponding CEO concentration 79.45 μg/ml). Furthermore, compared with the casting method, the mild electrospinning process was more favorable for maintaining greater CEO in the obtained film. The PLA/CEO/β-CD nanofilm can effectively prolong the shelf life of pork, suggesting it has potential application in active food packaging. Copyright © 2015 Elsevier Ltd. All rights reserved.

  13. Stabilization and prolonged reactivity of aqueous-phase ozone with cyclodextrin

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Dettmer, Adam; Ball, Raymond; Boving, Thomas B.

    Recalcitrant organic groundwater contaminants, such as 1,4-dioxane, may require strong oxidants for complete mineralization. However, their efficacy for in-situ chemical oxidation (ISCO) is limited by oxidant decay and reactivity. Hydroxypropyl-β-cyclodextrin (HPβCD) was examined for its ability to stabilize aqueous-phase ozone (O3) and prolong oxidation potential through inclusion complex formation. Partial transformation of HPβCD by O3 was observed. However, HPβCD proved to be sufficiently recalcitrant, because it was only partially degraded in the presence of O3. The formation of a HPβCD:O3 clathrate complex was observed, which stabilized decay of O3. The presence of HPβCD increased the O3 half-life linearly with increasingmore » HPβCD:O3 molar ratio. The O3 half-life in solutions increased by as much as 40-fold relative to HPβCD-free O3 solutions. Observed O3 release from HPβCD and indigo oxidation confirmed that the formation of the inclusion complex is reversible. This proof-of-concept study demonstrates that HPβCD can complex O3 while preserving its reactivity. These results suggest that the use of clathrate stabilizers, such as HPβCD, can support the development of a facilitated-transport enabled ISCO for the O3treatment of groundwater contaminated with recalcitrant compounds.« less

  14. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Schibilla, Frauke; Voskuhl, Jens; Fokina, Natalie A.

    We report the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane, and triamantane by β-cyclodextrin and γ-cyclodextrin (β-CD and γ-CD), which have particularly well-suited hydrophobicity and symmetry for an optimal fit of the host and guest molecules. We studied the host–guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity, but observed 1:2 association for the largest ND in the series (triamantane) with β-CD. Here, we found higher binding affinities for carboxy-substituted NDs than for amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with d-mannose by using adamantane, diamantane, and triamantanemore » as non-covalent anchors, and the resulting vesicles were compared with the lectin concanavalin A in agglutination experiments. Agglutination was directly correlated to the host–guest association: adamantane showed lower agglutination than di- or triamantane with β-CDV and almost no agglutination with γ-CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.« less

  15. Host-Guest Complexes of Cyclodextrins and Nanodiamonds as a Strong Non-Covalent Binding Motif for Self-Assembled Nanomaterials

    DOE PAGES

    Schibilla, Frauke; Voskuhl, Jens; Fokina, Natalie A.; ...

    2017-11-06

    We report the inclusion of carboxy- and amine-substituted molecular nanodiamonds (NDs) adamantane, diamantane, and triamantane by β-cyclodextrin and γ-cyclodextrin (β-CD and γ-CD), which have particularly well-suited hydrophobicity and symmetry for an optimal fit of the host and guest molecules. We studied the host–guest interactions in detail and generally observed 1:1 association of the NDs with the larger γ-CD cavity, but observed 1:2 association for the largest ND in the series (triamantane) with β-CD. Here, we found higher binding affinities for carboxy-substituted NDs than for amine-substituted NDs. Additionally, cyclodextrin vesicles (CDVs) were decorated with d-mannose by using adamantane, diamantane, and triamantanemore » as non-covalent anchors, and the resulting vesicles were compared with the lectin concanavalin A in agglutination experiments. Agglutination was directly correlated to the host–guest association: adamantane showed lower agglutination than di- or triamantane with β-CDV and almost no agglutination with γ-CDV, whereas high agglutination was observed for di- and triamantane with γ-CDV.« less

  16. Use of Carboxymethyl-beta-cyclodextrin (CMCD) as Flushing Agent for Remediation of Metal Contaminated Soil

    NASA Astrophysics Data System (ADS)

    Skold, M. E.; Thyne, G. D.; McCray, J. E.; Drexler, J. W.

    2005-12-01

    One of the major challenges in remediating soil and ground water is the presence of mixed organic and inorganic contaminants. Due to their very different behavior, research has to a large extent focused on remediation of either organic or inorganic contaminants rather than mixed waste. Cyclodextrins (CDs) are a group of non-toxic sugar based molecules that do not sorb to soil particles and do not experience pore size exclusion. Thus, they have good hydraulic properties. CDs enhance the solubility of organic compounds by forming inclusion complexes between organic contaminants and the non-polar cavity at the center of the CD. By substituting functional groups to the cyclodextrin molecule it can form complexes with heavy metals. Previous studies have shown that carboxymethyl-beta-cyclodextrin (CMCD) can simultaneously complex organic and inorganic contaminants. The aim of this study is to compare how strongly CMCD complexes several common heavy metals, radioactive elements and a common divalent cation. Results from batch experiments show that CMCD has the ability to complex a wide array of heavy metals and radioactive elements. The solubility of metal oxalates and metal oxides clearly increased in the presence of CMCD. Logarithmic conditional formation constants ranged from 3.5 to 6 for heavy metals and from 3 to 6 for radioactive elements. Calcium, which may compete for binding sites, has a logarithmic conditional formation constant of 3.1. Batch experiments performed at 10 and 25 degrees C showed little temperature effect on conditional formation constants. Results from batch experiments were compared to results from column experiments where Pb was sorbed onto hydrous ferric oxide coated sand and subsequently removed by a CMCD solution. The results indicate that CMCD is a potential flushing agent for remediation of mixed waste sites.

  17. Anti-inflammatory, analgesic and ulcerogenic properties of S-(+)-ibuproxam, racemic ibuproxam-beta-cyclodextrin and S-(+)-ibuproxam-beta-cyclodextrin.

    PubMed

    Bole-Vunduk, B; Verhnjak, K; Zmitek, J

    1996-11-01

    The anti-inflammatory, analgesic and gastric mucosal damage-inducing activities of S-(+)-ibuproxam, and S-(+)-ibuproxam-beta-cyclodextrin, new propionic acid derivatives, and racemic ibuproxam-beta-cyclodextrin were investigated in three animal models and compared with those of racemic ibuproxam, racemic ibuprofen and its optical enantiomer S-(+)-ibuprofen. The anti-inflammatory activities of racemic ibuprofen, S-(+)-ibuprofen and racemic ibuproxam in carrageenan-induced paw oedema in rats were almost equipotent and slightly greater than those of S-(+)-ibuproxam and S-(+)-ibuproxam-beta-cyclodextrin, and significantly greater than that of racemic ibuproxam-beta-cyclodextrin. In abdominal constriction tests in mice, the analgesic effects of racemic ibuproxam, S-(+)-ibuproxam, racemic ibuproxam-beta-cyclodextrin and S-(+)-ibuproxam-beta-cyclodextrin were significantly less pronounced than those of racemic ibuprofen and S-(+)-ibuprofen. Ulcerogenic activity of S-(+)-ibuproxam-beta-cyclodextrin in rats was found to be significantly weaker than that of racemic ibuproxam-beta-cyclodextrin, racemic ibuproxam and S-(+)-ibuproxam and, most notably, weaker than those of racemic ibuprofen and S-(+)ibuprofen. These results indicate that S-(+)-ibuproxam-beta-cyclodextrin could be a novel potent anti-inflammatory and analgesic agent with a therapeutic index more favourable than that of the classical non-steroid anti-inflammatory drugs ibuprofen and ibuproxam.

  18. Liposomes entrapping β-cyclodextrin/ibuprofen inclusion complex: Role of the host and the guest on the bilayer integrity and microviscosity.

    PubMed

    Angelini, Guido; Campestre, Cristina; Boncompagni, Simona; Gasbarri, Carla

    2017-12-01

    Multilamellar vesicles (MLVs) from 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) were prepared by using the dehydration-rehydration method. The β-cyclodextrin/Ibuprofen inclusion complex (β-CD/Ibu) was formed and solubilised into the aqueous compartments of the investigated vesicles. The resulting POPC MLVs entrapping β-CD/Ibu complex were essentially homogeneous in shape as demonstrated by Transmission Electron Microscopy (TEM). The liposomal stability was determined at 37.0±0.1°C by following the outflux rate of 5(6)-carboxyfluorescein (CF) at pH 7.40, while the membrane microviscosity was estimated by the ratio of the fluorescence intensities of pyrene in excimer and monomer state. The results presented herein confirm that interactions between POPC and β-CD occur and suggest that associations between POPC and Ibuprofen are also involved in the properties of the investigated liposomes. Copyright © 2017 Elsevier B.V. All rights reserved.

  19. An in vitro Comparison of Microdialysis Relative Recovery of Met- and Leu-Enkephalin Using Cyclodextrins and Antibodies as Affinity Agents

    PubMed Central

    Fletcher, Heidi J.; Stenken, Julie A.

    2008-01-01

    Cyclodextrins and antibodies have been used as affinity agents to improve relative recovery during microdialysis sampling. Two neuropeptides, methionine-enkephalin (ME) and leucine-enkephalin (LE), were chosen to compare the use of cyclodextrins and antibodies as possible affinity agents for improving their relative recovery across polycarbonate and polyethersulfone membranes during in vitro sampling. Cyclodextrins (CD) including β-CD, 2-hydroxypropyl-β-cyclodextrin (2HPβ-CD), and γ-CD gave improvements of relative recovery for both peptides of less than 2-fold as compared to controls. Comparisons of relative recovery between tyrosine-glycine-glycine, tyrosine, and phenylalanine using different cyclodextrins in the perfusion fluid were also obtained. Inclusion of an antibody against met-enkephalin in the microdialysis perfusion fluid resulted in relative recovery increases of up to 2.5-fold. These results show that using antibodies as affinity agents during microdialysis sampling may be more effective agents to improve the relative recovery of these opioid neuropeptides. PMID:18558138

  20. High-pressure/low-temperature neutron scattering of gas inclusion compounds: Progress and prospects

    PubMed Central

    Zhao, Yusheng; Xu, Hongwu; Daemen, Luke L.; Lokshin, Konstantin; Tait, Kimberly T.; Mao, Wendy L.; Luo, Junhua; Currier, Robert P.; Hickmott, Donald D.

    2007-01-01

    Alternative energy resources such as hydrogen and methane gases are becoming increasingly important for the future economy. A major challenge for using hydrogen is to develop suitable materials to store it under a variety of conditions, which requires systematic studies of the structures, stability, and kinetics of various hydrogen-storing compounds. Neutron scattering is particularly useful for these studies. We have developed high-pressure/low-temperature gas/fluid cells in conjunction with neutron diffraction and inelastic neutron scattering instruments allowing in situ and real-time examination of gas uptake/release processes. We studied the formation of methane and hydrogen clathrates, a group of inclusion compounds consisting of frameworks of hydrogen-bonded H2O molecules with gas molecules trapped inside the cages. Our results reveal that clathrate can store up to four hydrogen molecules in each of its large cages with an intermolecular H2–H2 distance of only 2.93 Å. This distance is much shorter than that in the solid/metallic hydrogen (3.78 Å), suggesting a strong densification effect of the clathrate framework on the enclosed hydrogen molecules. The framework-pressurizing effect is striking and may exist in other inclusion compounds such as metal-organic frameworks (MOFs). Owing to the enormous variety and flexibility of their frameworks, inclusion compounds may offer superior properties for storage of hydrogen and/or hydrogen-rich molecules, relative to other types of compounds. We have investigated the hydrogen storage properties of two MOFs, Cu3[Co(CN)6]2 and Cu3(BTC)2 (BTC = benzenetricarboxylate), and our preliminary results demonstrate that the developed neutron-scattering techniques are equally well suited for studying MOFs and other inclusion compounds. PMID:17389387

  1. Peptide-Appended Permethylated β-Cyclodextrins with Hydrophilic and Hydrophobic Spacers

    PubMed Central

    2017-01-01

    A novel synthetic methodology, employing a combination of the strain-promoted azide–alkyne cycloaddition and maleimide–thiol reactions, for the preparation of permethylated β-cyclodextrin-linker-peptidyl conjugates is reported. Two different bifunctional maleimide cross-linking probes, the polyethylene glycol containing hydrophilic linker bicyclo[6.1.0] nonyne-maleimide and the hydrophobic 5′-dibenzoazacyclooctyne-maleimide, were attached to azide-appended permethylated β-cyclodextrin. The successfully introduced maleimide function was exploited to covalently graft a cysteine-containing peptide (Ac-Tyr-Arg-Cys-Amide) to produce the target conjugates. The final target compounds were isolated in high purity after purification by isocratic preparative reverse-phase high-performance liquid chromatography. This novel synthetic approach is expected to give access to many different cyclodextrin–linker peptides. PMID:28697600

  2. Cyclodextrin-supported organic matrix for application of MALDI-MS for forensics. Soft-ionization to obtain protonated molecules of low molecular weight compounds

    NASA Astrophysics Data System (ADS)

    Yonezawa, Tetsu; Asano, Takashi; Fujino, Tatsuya; Nishihara, Hiroshi

    2013-06-01

    A mass measurement technique for detecting low-molecular-weight drugs with a cyclodextrin-supported organic matrix was investigated. By using cyclodextrin-supported 2,4,6-trihydroxyacetophenone (THAP), the matrix-related peaks of drugs were suppressed. The peaks of protonated molecules of the sample and THAP were mainly observed, and small fragments were detected in a few cases. Despite the Na+ and K+ peaks were observed in the spectrum, Na+ or K+ adduct sample molecules were undetected, owing to the sugar units of cyclodextrin. The advantages of MALDI-MS with cyclodextrin-supported matrices as an analytical tool for forensic samples are discussed. The suppression of alkali adducted molecules and desorption process are also discussed.

  3. Comparative evaluation of the chiral recognition potential of single-isomer sulfated beta-cyclodextrin synthesis intermediates in non-aqueous capillary electrophoresis.

    PubMed

    Fejős, Ida; Varga, Erzsébet; Benkovics, Gábor; Darcsi, András; Malanga, Milo; Fenyvesi, Éva; Sohajda, Tamás; Szente, Lajos; Béni, Szabolcs

    2016-10-07

    The enantioselectivity of neutral single-isomer synthetic precursors of sulfated-β-cyclodextrins was studied. Four neutral single-isomer cyclodextrins substituted on the secondary side with acetyl and/or methyl functional groups, heptakis(2-O-methyl-3,6-dihydroxy)-β-cyclodextrin (HM-β-CD), heptakis(2,3-di-O-acetyl-6-hydroxy)-β-cyclodextrin (HDA-β-CD), heptakis(2,3-di-O-methyl-6-hydroxy)-β-cyclodextrin (HDM-β-CD), heptakis(2-O-methyl-3-O-acetyl-6-hydroxy)-β-cyclodextrin (HMA-β-CD), and their sulfated analogs the negatively charged heptakis(2,3-di-O-methyl-6-sulfato)-β-cyclodextrin (HDMS-β-CD) and heptakis(2,3-di-O-acetyl-6-sulfato)-β-cyclodextrin (HDAS-β-CD) were investigated by non-aqueous capillary electrophoresis in the view of enantiodiscrimination for various drugs and related pharmaceutical compounds. The focus of the present work was on the chiral selectivity studies of the neutral derivatives, which are the synthesis intermediates of the sulfated products. The chiral recognition experiments proved that among the neutral compounds the HMA-β-CD shows remarkable enantioselectivity towards chiral guests in non-aqueous capillary electrophoresis, while HM-β-CD, HDA-β-CD and HDM-β-CD failed to resolve any of the 25 studied racemates under the applied experimental conditions. In order to get deeper insight into the molecular interactions between the studied single-isomer cyclodextrin and chiral fluoroquinolones (ofloxacin, gatifloxacin and lomefloxacin) and β-blockers (propranolol), 1 H and ROESY NMR experiments were performed. The 2-O-methylation in combination with the 3-O-acetylation of the host was evidenced to exclusively carry the essential spatial arrangement for chiral recognition. Copyright © 2016 Elsevier B.V. All rights reserved.

  4. Functionalization of Lipid-Based Nutrient Supplement with β-Cyclodextrin Inclusions of Oregano Essential Oil.

    PubMed

    Gaur, Shashank; Lopez, Emely C; Ojha, Ankur; Andrade, Juan E

    2018-06-01

    Intestinal parasitic infection is one of the main causes of acute undernutrition in children. Oral consumption of oregano essential oil (OEO) can reduce intestinal parasitic infections, however, its addition to therapeutic and supplementary foods is hampered by its undesirable flavor. The objective of this study was to develop a functional lipid-based nutrient supplement (LNS) containing OEO, which is stable, acceptable and provides targeted intestinal delivery of bioactive. β-cyclodextrin (β-CyD) inclusion complexes of OEO (β-CyD-OEO), and carvacrol (β-CyD-CV) (1:1 molar) were prepared using slurry complexation (-20 °C) method and characterized based on encapsulation efficiency, moisture content, morphology, and 2-phase in vitro digestion stability. Carvacrol (CV) content was measured using reverse phase HPLC-UV. LNS containing β-CyD-OEO (27.2 mg encapsulate/20 g LNS) was formulated using Indian staples and ingredients. Discriminatory sensory tests (triangle) were performed with college students (n = 58) and low-income women (n = 25), with young children at home (1 to 6 years), living in Mehsana, India to evaluate differences between LNS with and without bioactive ingredient (β-CyD-OEO only). Moisture of dried complexes ranged 9.1% to 9.7% d.b., whereas water activity 0.35 to 0.412. The complex size and encapsulation efficiency of β-CyD-OEO and β-CyD-CV were 1.5 to 7 μm and 4 to 20 μm, and 86.04 ± 4.48% and 81.39 ± 3.34%, respectively. The bioactive complexes were stable through the gastric and intestinal phases. Bioaccessibility of encapsulated CV ranged 6.0% to 7.7%. Sensory tests revealed no differences (P > 0.05) in color, aroma, and taste between LNS with and without β-CyD-OEO complexes. Functionalization of LNS with β-CyD-OEO is feasible based on in vitro stability and sensory studies. Despite its antiparasitic activities, the addition of oregano essential oil into foods is limited due to its strong flavor and volatility. In this

  5. Chiral discrimination in cyclodextrin complexes of amino acid derivatives: beta-cyclodextrin/N-acetyl-L-phenylalanine and N-acetyl-D-phenylalanine complexes.

    PubMed

    Alexander, Jennifer M; Clark, Joanna L; Brett, Tom J; Stezowski, John J

    2002-04-16

    In a systematic study of molecular recognition of amino acid derivatives in solid-state beta-cyclodextrin (beta-CD) complexes, we have determined crystal structures for complexes of beta-cyclodextrin/N-acetyl-L-phenylalanine at 298 and 20 K and for N-acetyl-D-phenylalanine at 298 K. The crystal structures for the N-acetyl-L-phenylalanine complex present disordered inclusion complexes for which the distribution of guest molecules at room temperature is not resolvable; however, they can be located with considerable confidence at low temperature. In contrast, the complex with N-acetyl-D-phenylalanine is well ordered at room temperature. The latter complex presents an example of a complex in this series in which a water molecule is included deeply in the hydrophobic torus of the extended dimer host. In an effort to understand the mechanisms of molecular recognition giving rise to the dramatic differences in crystallographic order in these crystal structures, we have examined the intermolecular interactions in detail and have examined insertion of the enantiomer of the D-complex into the chiral beta-CD complex crystal lattice.

  6. A new technique for promoting cyclic utilization of cyclodextrins in biotransformation.

    PubMed

    Shen, Yanbing; Yu, Ziqi; Yang, Xu; Wang, Fang; Luo, Jianmei; Wang, Min

    2017-01-01

    Cyclodextrins (CDs) can improve the productivity of steroid biotransformation by enhancing substrate solubility. CDs can be recycled by grafting them with appropriate carriers. Loofah fiber is an excellent grafting material for CDs, and can be applied to the biotransformation and recycling of β-cyclodextrin (β-CD). In this work, a technique for recycling β-CD in cortisone acetate (CA) biotransformation by Arthrobacter simplex CPCC 140451 was studied. Loofah fiber-grafted β-CD (LF-β-CD) was prepared using epichlorohydrin, which is a cross-linking agent. The grafting yield of β-CD was 74.8 mg g -1 dried fibers. LF-β-CD could increase the solubility of CA and enhance biotransformation. The initial conversion rate of CA was 1.5-fold higher than that of the blank group. LF-β-CD was also used in biocatalytic reactions for eight cycles, and it maintained the conversion ratio of CA at approximately 90%. Given the above positive results, LF-β-CD can be utilized in biotechnological recycling applications. This method can also be applied to CD derivatives and hydrophobic compounds.

  7. Intranasal Administration of PACAP: Uptake by Brain and Brain Region Targeting with Cyclodextrins

    PubMed Central

    Nonaka, Naoko; Farr, Susan A.; Nakamachi, Tomoya; Morley, John E.; Nakamura, Masanori; Shioda, Seiji; Banks, William A.

    2012-01-01

    Pituitary adenylate cyclase activating polypeptide (PACAP) is a potent neurotrophic and neuroprotectant that is transported across the blood-brain barrier in amounts sufficient to affect brain function. However, its short half-life in blood makes it difficult to administer peripherally. Here, we determined whether the radioactively labeled 38 amino acid form of PACAP can enter the brain after intranasal (i.n.) administration. Occipital cortex and striatum were the regions with the highest uptake, peaking at levels of about 2-4 percent of the injected dose per g of brain region. Inclusion of unlabeled PACAP greatly increased retention of I-PACAP by brain probably because of inhibition of the brain-to-blood efflux transporter for PACAP located at the blood-brain barrier. Sufficient amounts of PACAP could be delivered to the brain to affect function as shown by improvement of memory in aged SAMP8 mice, a model of Alzheimer’s disease. We found that each of three cyclodextrins when included in the i.n. injection produced a unique distribution pattern of I-PACAP among brain regions. As examples, β-cyclodextrin greatly increased uptake by the occipital cortex and hypothalamus, α-cyclodextrin increased uptake by the olfactory bulb and decreased uptake by the occipital cortex and striatum, and (2-hydropropyl)-β-cyclodextrin increased uptake by the thalamus and decreased uptake by the striatum. These results show that therapeutic amounts of PACAP can be delivered to the brain by intranasal administration and that cyclodextrins may be useful in the therapeutic targeting of peptides to specific brain regions. PMID:22687366

  8. Inkjet printing of antiviral PCL nanoparticles and anticancer cyclodextrin inclusion complexes on bioadhesive film for cervical administration.

    PubMed

    Varan, Cem; Wickström, Henrika; Sandler, Niklas; Aktaş, Yeşim; Bilensoy, Erem

    2017-10-15

    Personalized medicine is an important treatment approach for diseases like cancer with high intrasubject variability. In this framework, printing is one of the most promising methods since it permits dose and geometry adjustment of the final product. With this study, a combination product consisting of anticancer (paclitaxel) and antiviral (cidofovir) drugs was manufactured by inkjet printing onto adhesive film for local treatment of cervical cancers as a result of HPV infection. Furthermore, solubility problem of paclitaxel was overcome by maintaining this poorly soluble drug in a cyclodextrin inclusion complex and release of cidofovir was controlled by encapsulation in polycaprolactone nanoparticles. In vitro characterization studies of printed film formulations were performed and cell culture studies showed that drug loaded film formulation was effective on human cervical adenocarcinoma cells. Our study suggests that inkjet printing technology can be utilized in the development of antiviral/anticancer combination dosage forms for mucosal application. The drug amount in the delivery system can be accurately controlled and modified. Moreover, prolonged drug release time can be obtained. Printing of anticancer and antiviral drugs on film seem to be a potential approach for HPV-related cervical cancer treatment and a good candidate for further studies. Copyright © 2017 Elsevier B.V. All rights reserved.

  9. β-cyclodextrin-ionic liquid polymer based dynamically coating for simultaneous determination of tetracyclines by capillary electrophoresis.

    PubMed

    Zhou, Chunyan; Deng, Jingjing; Shi, Guoyue; Zhou, Tianshu

    2017-04-01

    Tetracyclines are a group of broad spectrum antibiotics widely used in animal husbandry to prevent and treat diseases. However, the improper use of tetracyclines may result in the presence of their residues in animal tissues or waste. Recently, great attention has been drawn towards the green solvents ionic liquids. Ionic liquids have been employed as a coating material to modify the electroosmotic flow in capillary electrophoresis. In this study, a functionalized ionic liquid, mono-6-deoxy-6-(3-methylimidazolium)-β-cyclodextrin tosylate, was synthesized and used for the simultaneous separation and quantification of tetracyclines by capillary electrophoresis. Good separation efficiency could be achieved due to the multiple functions of β-cyclodextrin derived ionic liquid, including the electrostatic interaction, the hydrogen bonding, and the cavity structure in β-cyclodextrin ionic liquid which can entrap the tetracyclines to form inclusion complex. After optimization, baseline separation achieved in 25 min with the running buffer consisted of 10 mmol/L, pH 7.2 phosphate buffer and 20 mmol/L β-cyclodextrin ionic liquid. The satisfied result demonstrated that the β-cyclodextrin ionic liquid is an ideal background electrolyte modifier in the separation of tetracyclines with high stability and good reproducibility. And it is an effective strategy to design and synthesize specific ILs as additive applied in separation. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  10. Cyclodextrin-water soluble polymer ternary complexes enhance the solubility and dissolution behaviour of poorly soluble drugs. Case example: itraconazole.

    PubMed

    Taupitz, Thomas; Dressman, Jennifer B; Buchanan, Charles M; Klein, Sandra

    2013-04-01

    The aim of the present series of experiments was to improve the solubility and dissolution/precipitation behaviour of a poorly soluble, weakly basic drug, using itraconazole as a case example. Binary inclusion complexes of itraconazole with two commonly used cyclodextrin derivatives and a recently introduced cyclodextrin derivative were prepared. Their solubility and dissolution behaviour was compared with that of the pure drug and the marketed formulation Sporanox®. Ternary complexes were prepared by addition of Soluplus®, a new highly water soluble polymer, during the formation of the itraconazole/cyclodextrin complex. A solid dispersion made of itraconazole and Soluplus® was also studied as a control. Solid state analysis was performed for all formulations and for pure itraconazole using powder X-ray diffraction (pX-RD) and differential scanning calorimetry (DSC). Solubility tests indicated that with all formulation approaches, the aqueous solubility of itraconazole formed with hydroxypropyl-β-cyclodextrin (HP-β-CD) or hydroxybutenyl-β-cyclodextrin (HBen-β-CD) and Soluplus® proved to be the most favourable formulation approaches. Whereas the marketed formulation and the pure drug showed very poor dissolution, both of these ternary inclusion complexes resulted in fast and extensive release of itraconazole in all test media. Using the results of the dissolution experiments, a newly developed physiologically based pharmacokinetic (PBPK) in silico model was applied to compare the in vivo behaviour of Sporanox® with the predicted performance of the most promising ternary complexes from the in vitro studies. The PBPK modelling predicted that the bioavailability of itraconazole is likely to be increased after oral administration of ternary complex formulations, especially when itraconazole is formulated as a ternary complex comprising HP-β-CD or HBen-β-CD and Soluplus®. Copyright © 2012 Elsevier B.V. All rights reserved.

  11. Multi-stage tandem mass spectrometric analysis of novel β-cyclodextrin-substituted and novel bis-pyridinium gemini surfactants designed as nanomedical drug delivery agents.

    PubMed

    Donkuru, McDonald; Chitanda, Jackson M; Verrall, Ronald E; El-Aneed, Anas

    2014-04-15

    This study aimed at evaluating the collision-induced dissociation tandem mass spectrometric (CID-MS/MS) fragmentation patterns of novel β-cyclodextrin-substituted- and bis-pyridinium gemini surfactants currently being explored as nanomaterial drug delivery agents. In the β-cyclodextrin-substituted gemini surfactants, a β-cyclodextrin ring is grafted onto an N,N-bis(dimethylalkyl)-α,ω-aminoalkane-diammonium moiety using variable succinyl linkers. In contrast, the bis-pyridinium gemini surfactants are based on a 1,1'-(1,1'-(ethane-1,2-diylbis(sulfanediyl))bis(alkane-2,1-diyl))dipyridinium template, defined by two symmetrical N-alkylpyridinium parts connected through a fixed ethane dithiol spacer. Detection of the precursor ion [M](2+) species of the synthesized compounds and the determination of mass accuracies were conducted using a QqTOF-MS instrument. A multi-stage tandem MS analysis of the detected [M](2+) species was conducted using the QqQ-LIT-MS instrument. Both instruments were equipped with an electrospray ionization (ESI) source. Abundant precursor ion [M](2+) species were detected for all compounds at sub-1 ppm mass accuracies. The β-cyclodextrin-substituted compounds, fragmented via two main pathways: Pathway 1: the loss of one head-tail region produces a [M-(N(Me)2-R)](2+) ion, from which sugar moieties (Glc) are sequentially cleaved; Pathway 2: both head-tail regions are lost to give [M-2(N(Me)2-R)](+), followed by consecutive loss of Glc units. Alternatively, the cleavage of the Glc units could also have occurred simultaneously. Nevertheless, the fragmentation evolved around the quaternary ammonium cations, with characteristic cleavage of Glc moieties. For the bis-pyridinium gemini compounds, they either lost neutral pyridine(s) to give doubly charged ions (Pathway A) or formed complementary pyridinium alongside other singly charged ions (Pathway B). Similar to β-cyclodextrin-substituted compounds, the fragmentation was centered on the

  12. Encapsulation of serotonin in β-cyclodextrin nano-cavities: Fluorescence spectroscopic and molecular modeling studies

    NASA Astrophysics Data System (ADS)

    Chaudhuri, Sudip; Chakraborty, Sandipan; Sengupta, Pradeep K.

    2010-06-01

    Serotonin is a physiologically important biogenic amine, deficiency of which leads to mental disorders such as Alzheimer's disease, schizophrenia, infantile autism, and depression. Both β-cyclodextrin (β-CD) and its chemically substituted synthetic varieties (often possessing enhanced aqueous solubility and improved drug complexing abilities) are finding wide applications as drug delivery vehicles. Here we have studied the encapsulation of serotonin in β-CD and succinyl-2-hydroxypropyl β-cyclodextrin (SHP-β-CD) by exploiting the intrinsic serotonin fluorescence. Enhanced fluorescence emission intensity (which increases by ˜18% and 34% in β-CD and SHPβ-CD respectively) and anisotropy ( r) ( r = 0.075 and 0.1 in β-CD and SHPβ-CD respectively) are observed in presence of the cyclodextrins. From the fluorescence data host-guest interaction with 1:1 stoichiometry is evident, the association constants ( K) being 126.06 M -1 and 461.62 M -1 for β-CD and SHPβ-CD respectively. Additionally, molecular docking and semiempirical calculations have been carried out which provide, for the first time, detailed insights regarding the encapsulation process. In particular, it is evident that the indole ring is inserted within the β-CD cavity with the aliphatic amine side chain protruding towards the primary rim of the β-CD cavity. Docking calculations reveal that hydrogen bonding interactions are involved in the formation of the inclusion complex. Semiempirical calculations indicate that formation of the 1:1 inclusion complex is energetically favorable which is consistent with the fluorescence data.

  13. Structural investigation of the β-cyclodextrin complexes with chiral bicyclic monoterpenes - Influence of the functionality group on the host-guest stoichiometry

    NASA Astrophysics Data System (ADS)

    Ceborska, Magdalena

    2017-10-01

    The crystal structures of the complexes of β-cyclodextrin with (+)- and (-)-camphors are presented. The comparison of the obtained crystal structures with available data for other complexes of β-cyclodextrin with chiral bicyclic monoterpenes (hydrocarbon (+)-fenchene and alcohols: (-)-isopinocampheol, and (+)-, and (-)-borneols) obtained from Cambridge Structural Database (CSD) shows the trend of alcohols to form dimeric complexes of 2:3 stoichiometry, while hydrocarbons and ketones prefer to form 2:2 host-guest inclusion complexes.

  14. Cyclodextrins: improving the therapeutic response of analgesic drugs: a patent review.

    PubMed

    de Oliveira, Makson G B; Guimarães, Adriana G; Araújo, Adriano A S; Quintans, Jullyana S S; Santos, Márcio R V; Quintans-Júnior, Lucindo J

    2015-01-01

    Cyclodextrins (CDs) are cyclic oligosaccharides that have recently been recognized as useful tools for optimizing the delivery of such problematic drugs. CDs can be found in at least 35 pharmaceutical products, such as anticancer agents, analgesic and anti-inflammatory drugs. Besides, several studies have demonstrated that CD-complexed drugs could provide benefits in solubility, stability and also improve pharmacological response when compared with the drug alone. The patent search was conducted in the databases WIPO, Espacenet, USPTO, Derwent and INPI, using the keywords cyclodextrin, pain and its related terms (analgesia, hyperalgesia, hypernociception, nociception, antinociception, antinociceptive). We found 442 patents. Criteria such as the complexation of analgesic agents and evidence of improvement of the therapeutic effect were indispensable for the inclusion of the patent. So, 18 patents were selected. We noticed that some patents are related to the complexation of opioids, NSAIDs, as well as natural products, in different types of CDs. The use of CDs creates the prospect of developing new therapeutic options for the most effective treatment of painful conditions, allowing a reduction of dosage of analgesic drugs and the occurrence of side effects. Thus, CDs can be an important tool to improve the efficacy and pharmacological profile of analgesic drugs.

  15. Twinning, Epitaxy and Domain Switching in Ferroelastic Inclusion Compounds

    NASA Technical Reports Server (NTRS)

    Hollingsworth, Mark D.; Peterson, Matthew L.

    2003-01-01

    Our research is in the area of solid-state organic chemistry, which lies at the interface between physical organic chemistry and materials science. We use crystalline solids as models to probe fundamental issues about physical processes, molecular interactions and chemical reactions that are important for fabrication, stabilization and application of technological materials. Much of our most recent work has focused on the phenomena of ferroelastic and ferroelectric domain switching, in which application of an external force or electric field to a crystal causes the molecules inside the crystal to reorient, in tandem, to a new orientational state. To better understand and control the domain switching process, we have designed and synthesized over twenty closely related, ferroelastic organic crystals. Our approach has been to use crystalline inclusion compounds, in which one molecule (the guest) is trapped within the crystalline framework of a second molecule (the host). By keeping the host constant and varying the proportions and kinds of guests, it has been possible to tailor these materials so that domain switching is rapid and reversible (which is desirable for high technology applications). Inclusion compounds therefore serve as powerful systems for understanding the specific molecular mechanisms that control domain switching.

  16. INTERACTIONS OF METHYL ORANGE WITH CYCLODEXTRIN/SODIUM-MONTMORILLONITE SYSTEMS PROBED BY UV-VISIBLE SPECTROSCOPY

    EPA Science Inventory

    Clay mineral colloids play important roles in the adsorption of polar organic contaminants in the environment. Similarly, cyclodextrins (CD) can entrap poorly water-soluble organic compounds. A combination of CDs and clay minerals affords great opportunities to investigate simult...

  17. Mathematical modelling of the transport of hydroxypropyl-β-cyclodextrin inclusion complexes of ranitidine hydrochloride and furosemide loaded chitosan nanoparticles across a Caco-2 cell monolayer.

    PubMed

    Sadighi, Armin; Ostad, S N; Rezayat, S M; Foroutan, M; Faramarzi, M A; Dorkoosh, F A

    2012-01-17

    Chitosan nanoparticles (CS-NPs) have been used to enhance the permeability of furosemide and ranitidine hydrochloride (ranitidine HCl) which were selected as candidates for two different biopharmaceutical drug classes having low permeability across Caco-2 cell monolayers. Drugs loaded CS-NPs were prepared by ionic gelation of CS and pentasodium tripolyphosphate (TPP) which added to the drugs inclusion complexes with hydroxypropyl-β-cyclodextrin (HP-βCD). The stability constants for furosemide/HP-βCD and ranitidine HCl/HP-βCD were calculated as 335 M(-1) and 410 M(-1), whereas the association efficiencies (AE%) of the drugs/HP-βCD inclusion complexes with CS-NPs were determined to be 23.0 and 19.5%, respectively. Zetasizer and scanning electron microscopy (SEM) were used to characterise drugs/HP-βCD-NPs size and morphology. Transport of both nano and non-nano formulations of drugs/HP-βCD complexes across a Caco-2 cell monolayer was assessed and fitted to mathematical models. Furosemide/HP-βCD-NPs demonstrated transport kinetics best suited for the Higuchi model, whereas other drug formulations demonstrated power law transportation behaviour. Permeability experiments revealed that furosemide/HP-βCD and ranitidine HCl/HP-βCD nano formulations greatly induce the opening of tight junctions and enhance drug transition through Caco-2 monolayers. Copyright © 2011 Elsevier B.V. All rights reserved.

  18. Chlorhexidine: beta-cyclodextrin inhibits yeast growth by extraction of ergosterol.

    PubMed

    Teixeira, K I R; Araújo, P V; Sinisterra, R D; Cortés, M E

    2012-04-01

    Chlorhexidine (Cx) augmented with beta-cyclodextrin (β-cd) inclusion compounds, termed Cx:β-cd complexes, have been developed for use as antiseptic agents. The aim of this study was to examine the interactions of Cx:β-cd complexes, prepared at different molecular ratios, with sterol and yeast membranes. The Minimal Inhibitory Concentration (MIC) against the yeast Candida albicans (C.a.) was determined for each complex; the MICs were found to range from 0.5 to 2 μg/mL. To confirm the MIC data, quantitative analysis of viable cells was performed using trypan blue staining. Mechanistic characterization of the interactions that the Cx:β-cd complexes have with the yeast membrane and assessment of membrane morphology following exposure to Cx:β-cd complexes were performed using Sterol Quantification Method analysis (SQM) and scanning electron microscopy (SEM). SQM revealed that sterol extraction increased with increasing β-cd concentrations (1.71 ×10(3); 1.4 ×10(3); 3.45 ×10(3), and 3.74 ×10(3) CFU for 1:1, 1:2, 1:3, and 1:4, respectively), likely as a consequence of membrane ergosterol solubilization. SEM images demonstrated that cell membrane damage is a visible and significant mechanism that contributes to the antimicrobial effects of Cx:β-cd complexes. Cell disorganization increased significantly as the proportion of β-cyclodextrin present in the complex increased. Morphology of cells exposed to complexes with 1:3 and 1:4 molar ratios of Cx:β-cd were observed to have large aggregates mixed with yeast remains, representing more membrane disruption than that observed in cells treated with Cx alone. In conclusion, nanoaggregates of Cx:β-cd complexes block yeast growth via ergosterol extraction, permeabilizing the membrane by creating cluster-like structures within the cell membrane, possibly due to high amounts of hydrogen bonding.

  19. Removal of emerging micropollutants from water using cyclodextrin.

    PubMed

    Nagy, Zsuzsanna Magdolna; Molnár, Mónika; Fekete-Kertész, Ildikó; Molnár-Perl, Ibolya; Fenyvesi, Éva; Gruiz, Katalin

    2014-07-01

    Small scale laboratory experiment series were performed to study the suitability of a cyclodextrin-based sorbent (ß-cyclodextrin bead polymer, BCDP) for modelling the removal of micropollutants from drinking water and purified waste water using simulated inflow test solutions containing target analytes (ibuprofen, naproxen, ketoprofen, bisphenol-A, diclofenac, β-estradiol, ethinylestradiol, estriol, cholesterol at 2-6 μg/L level). This work was focused on the preliminary evaluation of BCDP as a sorbent in two different model systems (filtration and fluidization) applied for risk reduction of emerging micropollutants. For comparison different filter systems combined with various sorbents (commercial filter and activated carbon) were applied and evaluated in the filtration experiment series. The spiked test solution (inflow) and the treated outflows were characterized by an integrated methodology including chemical analytical methods gas chromatography-tandem mass spectrometry (GC-MS/MS) and various environmental toxicity tests to determine the efficiency and selectivity of the applied sorbents. Under experimental conditions the cyclodextrin-based filters used for purification of drinking water in most cases were able to absorb more than 90% of the bisphenol-A and of the estrogenic compounds. Both the analytical chemistry and toxicity results showed efficient elimination of these pollutants. Especially the toxicity of the filtrate decreased considerably. Laboratory experiment modelling post-purification of waste water was also performed applying fluidization technology by ß-cyclodextrin bead polymer. The BCDP removed efficiently from the spiked test solution most of the micropollutants, especially the bisphenol-A (94%) and the hormones (87-99%) The results confirmed that the BCDP-containing sorbents provide a good solution to water quality problems and they are able to decrease the load and risk posed by micropollutants to the water systems. Copyright © 2014

  20. Circularly Polarized Luminescence from a Pyrene-Cyclodextrin Supra-Dendron.

    PubMed

    Zhang, Yuening; Yang, Dong; Han, Jianlei; Zhou, Jin; Jin, Qingxian; Liu, Minghua; Duan, Pengfei

    2018-05-22

    Soft nanomaterials with circularly polarized luminescence (CPL) have been currently attracting great interest. Here, we report a pyrene-containing π-peptide dendron hydrogel, which shows 1D and 2D nanostructures with varied CPL activities. It was found that the individual dendrons formed hydrogels in a wide pH range (3-12) and self-assembled into helices with pH-tuned pitches. Through chirality transfer, the pyrene unit could show CPL originated from both the monomer and excimer bands. When cyclodextrin was introduced, different supra-dendrons were obtained with β-cyclodextrin (PGAc@β-CD) and γ-cyclodextrin (PGAc@γ-CD) through host-guest interactions, respectively. Interestingly, the PGAc@β-CD and PGAc@γ-CD supra-dendrons self-assembled into 2D nanosheet and entangled nanofibers, respectively, showing cyclodextrin induced circularly polarized emission from both the monomer and excimer bands of the pyrene moiety. Thus, through a simple host-guest interaction, both the nanostructures and the chiroptical activities could be modulated.

  1. The Periplasmic Cyclodextrin Binding Protein CymE from Klebsiella oxytoca and Its Role in Maltodextrin and Cyclodextrin Transport

    PubMed Central

    Pajatsch, Markus; Gerhart, Maria; Peist, Ralf; Horlacher, Reinhold; Boos, Winfried; Böck, August

    1998-01-01

    Klebsiella oxytoca M5a1 has the capacity to transport and to metabolize α-, β- and γ-cyclodextrins. Cyclodextrin transport is mediated by the products of the cymE, cymF, cymG, cymD, and cymA genes, which are functionally homologous to the malE, malF, malG, malK, and lamB gene products of Escherichia coli. CymE, which is the periplasmic binding protein, has been overproduced and purified. By substrate-induced fluorescence quenching, the binding of ligands was analyzed. CymE bound α-cyclodextrin, β-cyclodextrin, and γ-cyclodextrin, with dissociation constants (Kd) of 0.02, 0.14 and 0.30 μM, respectively, and linear maltoheptaose, with a Kd of 70 μM. In transport experiments, α-cyclodextrin was taken up by the cym system of K. oxytoca three to five times less efficiently than maltohexaose by the E. coli maltose system. Besides α-cyclodextrin, maltohexaose was also taken up by the K. oxytoca cym system, but because of the inability of maltodextrins to induce the cym system, growth of E. coli mal mutants on linear maltodextrin was not observed when the cells harbored only the cym uptake system. Strains which gained this capacity by mutation could easily be selected, however. PMID:9573146

  2. Using reversed phase high performance liquid chromatography to study the complexation of anthocyanins with β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Deineka, V. I.; Lapshova, M. S.; Deineka, L. A.

    2014-06-01

    It is shown by means of reversed phase high performance liquid chromatography (RP HPLC) with mobile phases containing additions of β-cyclodextrin that 5-glucosides of cyanidin and pelargonidin form stronger inclusion complexes than 3-glucosides; this is explained by the steric interference of the glucoside radical.

  3. Two-photon absorption properties of cationic 1,4-bis(styryl)benzene derivative and its inclusion complexes with cyclodextrins.

    PubMed

    Nag, Okhil Kumar; Nayak, Rati Ranjan; Lim, Chang Su; Kim, In Hong; Kyhm, Kwangseuk; Cho, Bong Rae; Woo, Han Young

    2010-07-29

    Two-photon absorption properties of 1,4-bis{4'-[N,N-bis(6''-trimethylammoniumhexyl)amino]styryl}benzene tetrabromide (C1) and its inclusion complexes (ICs) with cyclodextrins (CDs) have been studied. Upon complexation with CDs, the absorption spectra of C1 showed a slight red shift, whereas the emission spectra showed a blue shift with concomitant increase in the fluorescence quantum efficiency. A Stern-Volmer study using K(3)Fe(CN)(6) as a quencher revealed significant reduction in the photoinduced charge transfer quenching, in accord with the IC formation. Comparison of the spectroscopic results reveals that C1 forms increasingly more stable ICs in the order C1/beta-CD < C1/gamma-CD < C1/(3gamma:beta)-CD (gamma-CD/beta-CD 3:1, mole ratio). Moreover, the two-photon action cross section of C1 increased from 200 GM for C1 to 400 GM for C1/beta-CD, 460 GM for C1/gamma-CD, and 650 GM for C1/(3gamma:beta)-CD, respectively. Furthermore, the two-photon microscopy images of HeLa cells stained with C1 emitted strong two-photon excited fluorescence in the plasma membrane. These results provide a useful guideline for the development of efficient two-photon materials for bioimaging applications.

  4. Mesoporous silicas with covalently immobilized β-cyclodextrin moieties: synthesis, structure, and sorption properties

    NASA Astrophysics Data System (ADS)

    Roik, Nadiia V.; Belyakova, Lyudmila A.; Trofymchuk, Iryna M.; Dziazko, Marina O.; Oranska, Olena I.

    2017-09-01

    Mesoporous silicas with chemically attached macrocyclic moieties were successfully prepared by sol-gel condensation of tetraethyl orthosilicate and β-cyclodextrin-silane in the presence of a structure-directing agent. Introduction of β-cyclodextrin groups into the silica framework was confirmed by the results of IR spectral, thermogravimetric, and quantitative chemical analysis of surface compounds. The porous structure of the obtained materials was characterized by nitrogen adsorption-desorption measurements, powder X-ray diffraction, transmission electron microscopy, and dynamic light scattering. It was found that the composition of the reaction mixture used in β-cyclodextrin-silane synthesis significantly affects the structural parameters of the resulting silicas. The increase in (3-aminopropyl)triethoxysilane as well as the coupling agent content in relation to β-cyclodextrin leads ultimately to the lowering or complete loss of hexagonal arrangement of pore channels in the synthesized materials. Formation of hexagonally ordered mesoporous structure was observed at molar composition of the mixture 0.049 TEOS:0.001 β-CD-silane:0.007 CTMAB:0.27 NH4OH:7.2 H2O and equimolar ratio of components in β-CD-silane synthesis. The sorption of alizarin yellow on starting silica and synthesized materials with chemically attached β-cyclodextrin moieties was studied in phosphate buffer solutions with pH 7.0. Experimental results of the dye equilibrium sorption were analyzed using Langmuir, Freundlich, and Redlich-Peterson isotherm models. It was proved that the Redlich-Peterson isotherm model is the most appropriate for fitting the equilibrium sorption of alizarin yellow on parent silica with hexagonally arranged mesoporous structure as well as on modified one with chemically immobilized β-cyclodextrin groups. [Figure not available: see fulltext.

  5. Solubility and transdermal permeation properties of a dehydroepiandrosterone cyclodextrin complex from hydrophilic and lipophilic vehicles.

    PubMed

    Ceschel, GianCarlo; Bergamante, Valentina; Maffei, Paola; Lombardi Borgia, Simone; Calabrese, Valeria; Biserni, Stefano; Ronchi, Celestino

    2005-01-01

    The permeation ability of a compound is due principally to its concentration in the vehicle and to its aptitude to cross the stratum corneum of the skin. In this work ex-vivo permeation studies on newly developed formulations containing dehydroepiandrosterone (DHEA) were carried out to investigate vehicles that increase drug permeation through the skin. To enhance the solubility of DHEA, its complex form with alpha-cyclodextrin was used. In addition, the two forms (pure drug and complex form) were introduced in hydrophilic (water), lipophilic (paraffin oil), and microemulsion vehicles to evaluate the synergic effect of cyclodextrins and microemulsion vehicles on solubility and permeation. From the results, DHEA solubility is notably conditioned by the type of the vehicle used: the highest solubilities (both for pure and complex drug forms) were obtained with microemulsion, followed by paraffin oil and water. Moreover, in all the studied vehicles, the c-DHEA was more soluble than DHEA. Permeation profile fluxes showed very interesting differences. That reflect the varying drug forms (pure drug and complex form), vehicles used, and drug concentrations in the vehicles. The major flux was obtained in complex of DHEA with alpha-cyclodextrins in the microemulsion vehicle. Therefore, this type of vehicle and drug form would be very useful in the development of a topical formulation containing DHEA.

  6. Synthesis and characterization of water-soluble hydroxybutenyl cyclomaltooligosaccharides (cyclodextrins).

    PubMed

    Buchanan, Charles M; Alderson, Susan R; Cleven, Curtis D; Dixon, Daniel W; Ivanyi, Robert; Lambert, Juanelle L; Lowman, Douglas W; Offerman, Rick J; Szejtli, Jozsef; Szente, Lajos

    2002-03-15

    We have examined the synthesis of hydroxybutenyl cyclomaltooligosaccharides (cyclodextrins) and the ability of these cyclodextrin ethers to form guest-host complexes with guest molecules. The hydroxybutenyl cyclodextrin ethers were prepared by a base-catalyzed reaction of 3,4-epoxy-1-butene with the parent cyclodextrins in an aqueous medium. Reaction byproducts were removed by nanofiltration before the hydroxybutenyl cyclodextrins were isolated by co-evaporation of water-EtOH. Hydroxybutenyl cyclodextrins containing no unsubstituted parent cyclodextrin typically have a degree of substitution of 2-4 and a molar substitution of 4-7. These hydroxybutenyl cyclodextrins are randomly substituted, amorphous solids. The hydroxybutenyl cyclodextrin ethers were found to be highly water soluble. Complexes of HBen-beta-CD with glibenclamide and ibuprofen were prepared and isolated. In both cases, the guest content of the complexes was large, and a significant increase in the solubility of the free drug was observed. Dissolution of the complexes in pH 1.4 water was very rapid, and significant increases in the solubility of the free drugs were observed. Significantly, after reaching equilibrium concentration, a decrease in the drug concentration over time was not observed.

  7. Dispersive micro-solid-phase extraction of benzoylurea insecticides in honey samples with a β-cyclodextrin-modified attapulgite composite as sorbent.

    PubMed

    Zhang, Panjie; Cui, Xiangqian; Yang, Xiaoling; Zhang, Sanbing; Zhou, Wenfeng; Gao, Haixiang; Lu, Runhua

    2016-01-01

    A β-cyclodextrin-modified attapulgite composite was prepared and used as a dispersive micro-solid-phase extraction sorbent for the determination of benzoylurea insecticides in honey samples. Parameters that may influence the extraction efficiency, such as the type and volume of the eluent, the amount of the sorbent, the extraction time and the ionic strength were investigated and optimized using batch and column procedures. Under optimized conditions, good linearity was obtained for all of the tested compounds, with R(2) values of at least 0.9834. The limits of detection were determined in the range of 0.2-1.0 μg/L. The recoveries of the four benzoylurea insecticides in vitex honey and acacia honey increased from 15.2 to 81.4% and from 14.2 to 82.0%, respectively. Although the β-cyclodextrin-modified attapulgite composite did not show a brilliant adsorption capacity for the selected benzoylurea insecticides, it exhibited a higher adsorption capacity toward relatively hydrophobic compounds, such as chlorfluazuron and hexaflumuron (recoveries in vitex honey samples ranged from 70.0 to 81.4% with a precision of 1.0-3.7%). It seemed that the logPow of the benzoylurea insecticides is related to their recoveries. The results confirmed the possibility of using cyclodextrin-modified palygorskite in the determination of relatively hydrophobic trace pharmaceutical residues. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

  8. Evaluation of newly synthesized and commercially available charged cyclomaltooligosaccharides (cyclodextrins) for capillary electrokinetic chromatography.

    PubMed

    Culha, Mustafa; Schell, Fred M; Fox, Shannon; Green, Thomas; Betts, Thomas; Sepaniak, Michael J

    2004-01-22

    A highly new charged cyclodextrin (CD) derivatives, (6-O-carboxymethyl-2,3-di-O-methyl)cyclomaltoheptaoses (CDM-beta-CDs), was synthesized and characterized as anionic reagents for capillary electrophoresis (CE) in an electrokinetic chromatography mode of separation. Substitution with dimethyl groups at the secondary hydroxyl sites of the CD is aimed at influencing the magnitude and selectivity of analyte-CD interactions, while substitution by carboxymethyl groups at the primary hydroxyl sites provides for high charge and electrophoretic mobility. Full regioselective methylation at the secondary hydroxyl sites was achieved in this work, while substitution at the primary hydroxyl sites generated a mixture of multiply charged products. The separation performance of CDM-beta-CD was evaluated using a variety of analyte mixtures. The results obtained from commercially available negatively charged cyclodextrins, heptakis(2,3-di-O-methyl-6-O-sulfo)cyclomaltoheptaose (HDMS-beta-CD) and O-(carboxymethyl)cyclomaltoheptaose (CM-beta-CD) with an average degree of substitution one (DS 1), were compared to CDM-beta-CD using a sample composed of eight positional isomers of dihydroxynaphthalene. Four hydroxylated polychlorobiphenyl derivatives, a group of chiral and isomeric catchecins, and chiral binaphthyl compounds were also separated with CDM-beta-CD. The effect of adding neutral beta-cyclodextrin (beta-CD) into the running buffer containing charged cyclodextrins was investigated and provided evidence of significant inter-CD interactions. Under certain running buffer conditions, the charged cyclodextrins also appear to adsorb to the capillary walls to various degrees.

  9. Genistein in 1:1 Inclusion Complexes with Ramified Cyclodextrins: Theoretical, Physicochemical and Biological Evaluation

    PubMed Central

    Danciu, Corina; Soica, Codruta; Oltean, Mircea; Avram, Stefana; Borcan, Florin; Csanyi, Erzsebet; Ambrus, Rita; Zupko, Istvan; Muntean, Delia; Dehelean, Cristina A.; Craina, Marius; Popovici, Ramona A.

    2014-01-01

    Genistein is one of the most studied phytocompound in the class of isoflavones, presenting a notable estrogenic activity and in vitro and/or in vivo benefits in different types of cancer such as those of the bladder, kidney, lung, pancreatic, skin and endometrial cancer. A big inconvenience for drug development is low water solubility, which can be solved by using hydrophilic cyclodextrins. The aim of this study is to theoretically analyze, based on the interaction energy, the possibility of a complex formation between genistein (Gen) and three different ramified cyclodextrins (CD), using a 1:1 molar ratio Gen:CD. Theoretical data were correlated with a screening of both in vitro and in vivo activity. Proliferation of different human cancer cell lines, antimicrobial activity and angiogenesis behavior was analyzed in order to see if complexation has a beneficial effect for any of the above mentioned activities and if so, which of the three CDs is the most suitable for the incorporation of genistein, and which may lead to future improved pharmaceutical formulations. Results showed antiproliferative activity with different IC50 values for all tested cell lines, remarkable antimicrobial activity on Bacillus subtilis and antiangiogenic activity as revealed by CAM assay. Differences regarding the intensity of the activity for pure and the three Gen complexes were noticed as explained in the text. The data represent a proof that the three CDs can be used for furtherer research towards practical use in the pharmaceutical and medical field. PMID:24473144

  10. SUPRAMOLECULAR COMPOSITE MATERIALS FROM CELLULOSE, CHITOSAN AND CYCLODEXTRIN: FACILE PREPARATION AND THEIR SELECTIVE INCLUSION COMPLEX FORMATION WITH ENDOCRINE DISRUPTORS

    PubMed Central

    Duri, Simon; Tran, Chieu D.

    2013-01-01

    We have successfully developed a simple and one step method to prepare high performance supramolecular polysaccharide composites from cellulose (CEL), chitosan (CS) and (2,3,6-tri-O-acetyl)-α-, β- and γ-cyclodextrin (α-, β- and γ-TCD). In this method, [BMIm+Cl−], an ionic liquid (IL), was used as a solvent to dissolve and prepare the composites. Since majority (>88%) of the IL used was recovered for reuse, the method is recyclable. XRD, FT-IR, NIR and SEM were used to monitor the dissolution process and to confirm that the polysaccharides were regenerated without any chemical modifications. It was found that unique properties of each component including superior mechanical properties (from CEL), excellent adsorbent for pollutants and toxins (from CS) and size/structure selectivity through inclusion complex formation (from TCDs) remain intact in the composites. Specifically, results from kinetics and adsorption isotherms show that while CS-based composites can effectively adsorb the endocrine disruptors (polychlrophenols, bisphenol-A), its adsorption is independent on the size and structure of the analytes. Conversely, the adsorption by γ-TCD-based composites exhibits strong dependency on size and structure of the analytes. For example, while all three TCD-based composites (i.e., α-, β- and γ-TCD) can effectively adsorb 2-, 3- and 4-chlorophenol, only γ-TCD-based composite can adsorb analytes with bulky groups including 3,4-dichloro- and 2,4,5-trichlorophenol. Furthermore, equilibrium sorption capacities for the analytes with bulky groups by γ-TCD-based composite are much higher than those by CS-based composites. Together, these results indicate that γ-TCD-based composite with its relatively larger cavity size can readily form inclusion complexes with analytes with bulky groups, and through inclusion complex formation, it can strongly adsorb much more analytes and with size/structure selectivity compared to CS-based composites which can adsorb the

  11. Cyclodextrins as new formulation entities and therapeutic agents.

    PubMed

    Sikharam, Sreevalli; Egan, Talmage D; Kern, Steven E

    2005-08-01

    This review is focused on recent advances in the application of cyclodextrins to new drug formulations, with emphasis on the field of anesthesia. Cyclodextrins are well-known excipients in the pharmaceutical industry. Their recent application to the anesthetic induction agent propofol as a means of creating a non-lipid formulation may lead to their introduction into anesthesia pharmacology. The development of a novel cyclodextrin as specific reversal agent for the neuromuscular blocker rocuronium (that acts as an in-vivo scavenging system to bind free rocuronium in the circulation) will also increase the likelihood that cyclodextrins will have a greater clinical presence in anesthesiology in the future. Cyclodextrin-containing polymers are also finding a role in the delivery of nucleic acids and protein therapeutic agents. Recent developments in cyclodextrins as excipients for anesthetics may soon culminate in their introduction into anesthesiology, although more research is necessary to better define their potential.

  12. Core-shell nanofibers of curcumin/cyclodextrin inclusion complex and polylactic acid: Enhanced water solubility and slow release of curcumin.

    PubMed

    Aytac, Zeynep; Uyar, Tamer

    2017-02-25

    Core-shell nanofibers were designed via electrospinning using inclusion complex (IC) of model hydrophobic drug (curcumin, CUR) with cyclodextrin (CD) in the core and polymer (polylactic acid, PLA) in the shell (cCUR/HPβCD-IC-sPLA-NF). CD-IC of CUR and HPβCD was formed at 1:2 molar ratio. The successful formation of core-shell nanofibers was revealed by TEM and CLSM images. cCUR/HPβCD-IC-sPLA-NF released CUR slowly but much more in total than PLA-CUR-NF at pH 1 and pH 7.4 due to the restriction of CUR in the core of nanofibers and solubility improvement shown in phase solubility diagram, respectively. Improved antioxidant activity of cCUR/HPβCD-IC-sPLA-NF in methanol:water (1:1) is related with the solubility enhancement achieved in water based system. The slow reaction of cCUR/HPβCD-IC-sPLA-NF in methanol is associated with the shell inhibiting the quick release of CUR. On the other hand, cCUR/HPβCD-IC-sPLA-NF exhibited slightly higher rate of antioxidant activity than PLA-CUR-NF in methanol:water (1:1) owing to the enhanced solubility. To conclude, slow release of CUR was achieved by core-shell nanofiber structure and inclusion complexation of CUR with HPβCD provides high solubility. Briefly, electrospinning of core-shell nanofibers with CD-IC core could offer slow release of drugs as well as solubility enhancement for hydrophobic drugs. Copyright © 2017 Elsevier B.V. All rights reserved.

  13. Physico-chemical and Biological Evaluation of Flavonols: Fisetin, Quercetin and Kaempferol Alone and Incorporated in beta Cyclodextrins.

    PubMed

    Corina, Danciu; Bojin, Florina; Ambrus, Rita; Muntean, Delia; Soica, Codruta; Paunescu, Virgil; Cristea, Mirabela; Pinzaru, Iulia; Dehelean, Cristina

    2017-01-01

    Fisetin,quercetin and kaempferol are among the important representatives of flavonols, biological active phytocomounds, with low water solubility. To evaluate the antimicrobial effect, respectively the antiproliferative and pro apoptotic activity on the B164A5 murine melanoma cell line of pure flavonols and their beta cyclodextrins complexes. Incorporation of fisetin, quercetin and kaempferol in beta cyclodextrins was proved by scanning electron microscopy (SEM), differencial scanning calorimetry (DSC) and X-ray powder diffraction (XRPD). Pure compounds and their complexes were tested for antiproliferative (MTT) and pro-apoptotic activity (Annexin V-PI) on the B164A5 murine melanoma cell line and for the antimicrobial properties (Disk Diffusion Method) on the selected strains. The phytocompounds presented in a different manner in vitro chemopreventive activity against B164A5 murine melanoma cell line and weak antimicrobial effect. The three flavonols: fisetin, quercetin and kaempferol were successfully incorporated in beta-cyclodextrin (BCD) and hydroxylpropyl-beta-cyclodextrin (HPBCD). Incorporation in beta cyclodextrins had a mix effect on the biological activity conducing to decrease, increase or consistent effect compared to pure phytocompound, depending on the screened process and on the chosen combination. Copyright© Bentham Science Publishers; For any queries, please email at epub@benthamscience.org.

  14. Synthesis of a thiol-β-cyclodextrin, a potential agent for controlling enzymatic browning in fruits and vegetables.

    PubMed

    Manta, Carmen; Peralta-Altier, Gabriela; Gioia, Larissa; Méndez, María F; Seoane, Gustavo; Ovsejevi, Karen

    2013-11-27

    A thiol-β-cyclodextrin was synthesized by a simple and environmentally friendly three-step method comprising epoxy activation of β-cyclodextrin, thiosulfate-mediated oxirane opening, and further reduction of the S-alkyl thiosulfate to a thiol group. The final step was optimized by using thiopropyl-agarose, a solid phase reducing agent with many advantages over soluble ones. β-Cyclodextrin thiolation was confirmed by titration with a thiol-reactive reagent, NMR studies, and MALDI-TOF/TOF. Thiolated cyclodextrin had an average value of one thiol group per molecule. Thiol-β-cyclodextrin proved to be an excellent agent for controlling polyphenol oxidase activity. This copper-containing enzyme is responsible for browning in fruits and vegetables. Under the same conditions, thiol-β-cyclodextrin generated a reductive microenvironment that increased the antibrowning effect on Red Delicious apples compared to unmodified β-cyclodextrin.

  15. Investigation of Cyclodextrin-Based Nanosponges for Solubility and Bioavailability Enhancement of Rilpivirine.

    PubMed

    Rao, Monica R P; Chaudhari, Jagruti; Trotta, Francesco; Caldera, Fabrizio

    2018-06-04

    Rilpivrine is BCS class II drug used for treatment of HIV infection. The drug has low aqueous solubility (0.0166 mg/ml) and dissolution rate leading to low bioavailability (32%). Aim of this work was to enhance solubility and dissolution of rilpivirine using beta-cyclodextrin-based nanosponges. These nanosponges are biocompatible nanoporous particles having high loading capacity to form supramolecular inclusion and non-inclusion complexes with hydrophilic and lipophilic drugs for solubility enhancement. Beta-cyclodextrin was crosslinked with carbonyl diimidazole and pyromellitic dianhydride to prepare nanosponges. The nanosponges were loaded with rilpivirine by solvent evaporation method. Binary and ternary complexes of drug with β-CD, HP-β-CD, nanosponges, and tocopherol polyethylene glycol succinate were prepared and characterized by phase solubility, saturation solubility in different media, in vitro dissolution, and in vivo pharmacokinetics. Spectral analysis by Fourier transform infrared spectroscopy, powder X-ray diffraction, and differential scanning calorimetry was performed. Results obtained from spectral characterization confirmed inclusion complexation. Phase solubility studies indicated stable complex formation. Saturation solubility was found to be 10-13-folds higher with ternary complexes in distilled water and 12-14-fold higher in 0.1 N HCl. Solubility enhancement was evident in biorelevant media. Molecular modeling studies revealed possible mode of entrapment of rilpivirine within β-CD cavities. A 3-fold increase in dissolution with ternary complexes was observed. Animal studies revealed nearly 2-fold increase in oral bioavailability of rilpivirine. It was inferred that electronic interactions, hydrogen bonding, and van der Waals forces are involved in the supramolecular interactions.

  16. Enantiomeric separation by capillary electrochromatography on a sulfated poly β-cyclodextrin modified silica-based monolith.

    PubMed

    Yuan, Ruijuan; Wang, Yan; Ding, Guosheng

    2010-01-01

    A sulfated poly β-cyclodextrin (SPCD) modified silica-based monolithic column was prepared for enantiomeric separation. First, 2-hydroxy-3-allyloxy-propyl-β-cyclodextrin (allyl-β-CD) was bonded onto a bifunctional reagent 3-(methacryloxy)propyltriethoxysilane (γ-MAPS) modified silica-based monolith through radical polymerization; the column was then sulfated with chlorosulfonic acid. The SPCD chiral stationary phase resolved the boring problem associated with desalting when sulfated CDs were synthesized to act as chiral additives. The inorganic salt in the column introduced during the sulfating process could be easily removed by washing the column with water for some time. Chiral compounds investigated were successfully resolved into their enantiomers on the SPCD modified monolith in the capillary electrochromatography (CEC) mode. Due to the existence of the -SO(3)H group, electrosmotic flow (EOF) was obviously increased, and all of the separations could be carried out in 20 min with only a minor loss in the column efficiency and resolution.

  17. Analysis of the phase solubility diagram of a phenacetin/competitor/beta-cyclodextrin ternary system, involving competitive inclusion complexation.

    PubMed

    Ono, N; Hirayama, F; Arima, H; Uekama, K

    2001-01-01

    The competitive inclusion complexations in the ternary phenacetin/competitors/beta-cyclodextrin (beta-CyD) systems were investigated by the solubility method, where m-bromobenzoic acid (m-BBA) and o-toluic acid (o-TA) were used as competitors. The solubility changes of the drug and competitors as a function of beta-CyD concentration in the ternary systems were formulated using their stability constants and intrinsic solubilities. The decrease in solubility of phenacetin by the addition of competitors could be quantitatively simulated by the formulation, when both drug and competitor give A(L) type solubility diagrams. On the other hand, when one of the guests gives a B(S) type solubility diagram, its solubility change was clearly reflected in that of the another guest, i.e., phenacetin gave an A(L) type solubility diagram in the binary phenacetin/beta-CyD system and o-TA gave a B(S) type diagram in the binary o-TA/beta-CyD system, but in the ternary phenacetin/o-TA/beta-CyD system, a new plateau region appeared in the original A(L) type diagram of phenacetin. This was explained by the solubilization theory of Higuchi and Connors. The solubility analysis of the ternary drug/competitor/CyD systems may be particularly useful for determination of the stability constant of a drug whose physicochemical and spectroscopic analyses are difficult, because they can be calculated by monitoring the solubility change of a competitor, without monitoring that of a drug. Furthermore, the present results suggest that attention should be paid to the type of the phase solubility diagram, as well as the magnitude of the stability constant and the solubility of the complex, for a rational formulation design of CyD complexes.

  18. Enhanced extracellular production of trans-resveratrol in Vitis vinifera suspension cultured cells by using cyclodextrins and methyljasmonate.

    PubMed

    Belchí-Navarro, Sarai; Almagro, Lorena; Lijavetzky, Diego; Bru, Roque; Pedreño, María A

    2012-01-01

    In this work, the effect of different inducing factors on trans-resveratrol extracellular production in Monastrell grapevine suspension cultured cells is evaluated. A detailed analysis provides the optimal concentrations of cyclodextrins, methyljasmonate and UV irradiation dosage, optimal cell density, elicitation time and sucrose content in the culture media. The results indicate that trans-resveratrol production decreases as the initial cell density increases for a constant elicitor concentration in Monastrell suspension cultured cells treated with cyclodextrins individually or in combination with methyljasmonate; the decrease observed in cell cultures elicited with cyclodextrins alone is far more drastic than those observed in the combined treatment. trans-Resveratrol extracellular production observed by the joint use of cyclodextrins and methyljasmonate (1,447.8 ± 60.4 μmol trans-resveratrol g(-1) dry weight) is lower when these chemical compounds are combined with UV light short exposure (669.9 ± 45.2 μmol trans-resveratrol g(-1) dry weight). Likewise, trans-resveratrol production is dependent on levels of sucrose in the elicitation medium with the maximal levels observed with 20 g l(-1) sucrose and the joint action of cyclodextrins and 100 μM methyljasmonate. The sucrose concentration did not seem to limit the process although it affects significantly the specific productivity since the lowest sucrose concentration is 10 g l(-1), the highest productivity is reached (100.7 ± 5.8 μmol trans-resveratrol g(-1) dry weight g(-1) sucrose) using cyclodextrins and 25 μM methyljasmonate.

  19. Fluorimetric and mass spectrometric study of the interaction of β-cyclodextrin and osthole

    NASA Astrophysics Data System (ADS)

    Zhang, Huarong; Zhang, Hanqi; Qu, Chenling; Bai, Lifei; Ding, Lan

    2007-11-01

    The inclusion complex of β-cyclodextrin (β-CD) and osthole was studied by the electrospray ionization mass spectrometry (ESI-MS) and fluorescence spectrometry. From the mass spectrum, the 1:1 stoichiometric inclusion complex of β-CD and osthole was observed. The tandem mass spectrum was performed. The fluorescence intensity of osthole increased in the present of β-CD. According to the 1:1 β-CD-osthole mode, the dissociation constant ( KD) was obtained by ESI-MS and fluorescence spectrometry. The KD of β-CD-osthole inclusion complex is 6.96 × 10 -3 mol L -1 obtained by mass spectrometry and that is 8.14 × 10 -3 mol L -1 obtained by fluorescence spectrometry, which is consistent with each other.

  20. Complexation of carbendazim with hydroxypropyl-β-cyclodextrin to improve solubility and fungicidal activity.

    PubMed

    Ge, Xia; Huang, Zheng; Tian, Shilong; Huang, Yulong; Zeng, Chaozhen

    2012-06-05

    The effect of hydroxypropyl-β-cyclodextrin (HPβCD) on the improvement of the solubility and fungicidal activity of carbendazim (MBC) has been investigated. The inclusion complexation of HPβCD with MBC has been prepared and characterized by phase solubility diagram, fluorescence, (1)H NMR, ROESY and FT-IR spectra. The stoichiometric ratio and stability constant were determined by Job's plot and phase solubility studies, respectively. The inclusion complex MBC·HPβCD has exhibited different properties from MBC. The obtained inclusion complex was found to significantly improve the water solubility of MBC. In addition, the biological activity indicated that the complex displayed the better fungicidal activity than MBC. The present study provided useful information for a more rational application of MBC. Copyright © 2012 Elsevier Ltd. All rights reserved.

  1. Mechanochemical Preparation of Stable Sub-100 nm γ-Cyclodextrin:Buckminsterfullerene (C60) Nanoparticles by Electrostatic or Steric Stabilization.

    PubMed

    Van Guyse, Joachim F R; de la Rosa, Victor R; Hoogenboom, Richard

    2018-02-21

    Buckminster fullerene (C 60 )'s main hurdle to enter the field of biomedicine is its low bioavailability, which results from its extremely low water solubility. A well-known approach to increase the water solubility of C 60 is by complexation with γ-cyclodextrins. However, the formed complexes are not stable in time as they rapidly aggregate and eventually precipitate due to attractive intermolecular forces, a common problem in inclusion complexes of cyclodextrins. In this study we attempt to overcome the attractive intermolecular forces between the complexes by designing custom γ-cyclodextrin (γCD)-based supramolecular hosts for C 60 that inhibit the aggregation found in native γCD-C 60 complexes. The approach entails the introduction of either repulsive electrostatic forces or increased steric hindrance to prevent aggregation, thus enhancing the biomedical application potential of C 60 . These modifications have led to new sub-100 nm nanostructures that show long-term stability in solution. © 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  2. Effective cleavage of phosphodiester promoted by the zinc(II) and copper(II) inclusion complexes of β-cyclodextrin.

    PubMed

    Zhou, Ying-Hua; Chen, Li-Qing; Tao, Jun; Shen, Jun-Li; Gong, Dao-Yu; Yun, Rui-Rui; Cheng, Yong

    2016-10-01

    To construct the model of metallohydrolase, two inclusion complexes [MLCl 2 (β-CD)] (1, M=Zn(II); 2, M=Cu(II); L=N,N'-bis(2-pyridylmethyl)amantadine; β-CD=β-cyclodextrin) were synthesized by mixing β-CDs with the pre-synthesized complexes G1, [ZnLCl 2 ] and G2, [CuLCl 2 ]. Structures of G1, G2, 1 and 2 were characterized by X-ray crystallography, respectively. In solution, two chloride anions of G1 and G2 underwent ligand exchange with solvent molecules according to ESI-MS analysis. The chemical equilibrium constants were determined by potentiometric pH titration. The kinetics of bis(4-nitrophenyl) phosphate (BNPP) hydrolysis catalyzed by G1, G2, 1 and 2 were examined at pHs ranging from 7.50 to 10.50 at 308±0.1K. The pH profile of rate constant of BNPP hydrolysis catalyzed by 1 exhibited an exponential increase with the second-order rate constant of 2.68×10 -3 M -1 s -1 assigned to the di-hydroxo species, which was approximately an order of magnitude higher than those of reported mono-Zn(II)-hydroxo species. The high reactivity was presumably hydroxyl-rich microenvironment provided by β-CDs, which might effect in stabilizing either the labile zinc-hydroxo species or the catalytic transition state. Copyright © 2016 Elsevier Inc. All rights reserved.

  3. Formulation, characterization and evaluation of cyclodextrin-complexed bendamustine-encapsulated PLGA nanospheres for sustained delivery in cancer treatment.

    PubMed

    Gidwani, Bina; Vyas, Amber

    2016-03-01

    PLGA nanospheres are considered to be promising drug carrier in the treatment of cancer. Inclusion complex of bendamustine (BM) with epichlorohydrin beta cyclodextrin polymer was prepared by freeze-drying method. Phase solubility study revealed formation of AL type complex with stability constant (Ks = 645 M(-1)). This inclusion complex was encapsulated into PLGA nanospheres using solid-in-oil-in-water (S/O/W) technique. The particle size and zeta potential of PLGA nanospheres loaded with cyclodextrin-complexed BM were about 151.4 ± 2.53 nm and - 31.9 ± (-3.08) mV. In-vitro release study represented biphasic release pattern with 20% burst effect and sustained slow release. DSC studies indicated that inclusion complex incorporated in PLGA nanospheres was not in a crystalline state but existed in an amorphous or molecular state. The cytotoxicity experiment was studied in Z-138 cells and IC50 value was found to be 4.3 ± 0.11 µM. Cell viability studies revealed that the PLGA nanospheres loaded with complex exerts a more pronounced effect on the cancer cells as compared to the free drug. In conclusion, PLGA nanospheres loaded with inclusion complex of BM led to sustained drug delivery. The nanospheres were stable after 3 months of storage conditions with slight change in their particle size, zeta potential and entrapment efficiency.

  4. Dual fluorescence of N-phenylanthranilic acid: Effect of solvents, pH and beta-cyclodextrin.

    PubMed

    Rajendiran, N; Balasubramanian, T

    2007-11-01

    Spectral characteristics of N-phenylanthranilic acid (NPAA) have been studied in different solvents, pH and beta-cyclodextrin (beta-CD) and compared with anthranilic acid (2-aminobenzoic acid, 2ABA). In all solvents a dual fluorescence is observed in NPAA, whereas 2ABA gives single emission. Combining the results observed in the absorption, fluorescence emission and fluorescence excitation spectra, it is found that strong intramolecular hydrogen bonding (IHB) interactions present in NPAA molecule. The inclusion complex of NPAA with beta-CD is analysed by UV-vis, fluorimetry, FT-IR, (1)H NMR, scanning electron microscope and AM 1 method. The above spectral studies show that NPAA forms a 1:1 inclusion complex with beta-CD and COOH group present in the beta-CD cavity. A mechanism is proposed to explain the inclusion process.

  5. Dual fluorescence of N-phenylanthranilic acid: Effect of solvents, pH and β-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Rajendiran, N.; Balasubramanian, T.

    2007-11-01

    Spectral characteristics of N-phenylanthranilic acid (NPAA) have been studied in different solvents, pH and β-cyclodextrin (β-CD) and compared with anthranilic acid (2-aminobenzoic acid, 2ABA). In all solvents a dual fluorescence is observed in NPAA, whereas 2ABA gives single emission. Combining the results observed in the absorption, fluorescence emission and fluorescence excitation spectra, it is found that strong intramolecular hydrogen bonding (IHB) interactions present in NPAA molecule. The inclusion complex of NPAA with β-CD is analysed by UV-vis, fluorimetry, FT-IR, 1H NMR, scanning electron microscope and AM 1 method. The above spectral studies show that NPAA forms a 1:1 inclusion complex with β-CD and COOH group present in the β-CD cavity. A mechanism is proposed to explain the inclusion process.

  6. Solubility profiles, hydration and desolvation of curcumin complexed with γ-cyclodextrin and hydroxypropyl-γ-cyclodextrin

    NASA Astrophysics Data System (ADS)

    Shityakov, Sergey; Salmas, Ramin Ekhteiari; Durdagi, Serdar; Roewer, Norbert; Förster, Carola; Broscheit, Jens

    2017-04-01

    In this study, we investigated curcumin (CUR) solubility profiles and hydration/desolvation effects of this substance formulated with γ-cyclodextrin (γ-CD) and hydroxypropyl-γ-cyclodextrin (HP-γ-CD) excipients. The CUR/HP-γ-CD complex was found to be more stable in solution with the highest apparent stability constant for CUR/HP-γ-CD (Kc = 1.58*104 M-1) as the more soluble form in distilled water. The in silico calculations, including molecular docking, Monte Carlo (MC), and molecular dynamics (MD) simulations, indicated that water molecules play an important role in host-guest complexation mediating the CUR binding to cyclodextrins via hydrogen bond formations. The CUR hydration/desolvation effects contributed to the complex formation by elevating the CUR binding affinity to both CDs. The CUR/HP-γ-CD complex after the CUR hydration was determined with a minimal Gibbs free energy of binding (ΔGbind = -9.93 kcal*mol-1) due to the major hydrophobic (vdW) forces. Overall, the results of this study can aid a development of cyclodextrin-based drug delivery vectors, signifying the importance of water molecules during the formulation processes.

  7. Use of natural and modified cyclodextrins as inhibiting agents of peach juice enzymatic browning.

    PubMed

    López-Nicolas, José M; Pérez-López, Antonio J; Carbonell-Barrachina, Angel; García-Carmona, Francisco

    2007-06-27

    Although cyclodextrins (CDs) have been successfully used as antibrowning agents in different fruit juices, no research has studied the effect of these compounds on enzymatic browning in peach juice. In this paper, the color of fresh peach juice was evaluated in the presence of two types of natural (alpha-CD and beta-CD) and a modified (maltosyl-beta-CD) CD, and the effectiveness of these compounds as browning inhibitors was determined using the color space CIELAB system. Moreover, to clarify the mechanism by which CDs inhibit peach juice enzymatic browning, the process was kinetically modeled in the absence and presence of CDs using a colorimetric method; the apparent complexation constants between the mixtures of diphenols present in peach juice and some types of CD were calculated. The results show that the highest affinity constant was presented by alpha-CD (Kc = 18.31 mM-1) followed by maltosyl-beta-CD (Kc = 11.17 mM-1), whereas beta-CD was incapable of inhibiting peach juice enzymatic browning. Cyclodextrin; browning; peach; juice; color; polyphenol oxidase.

  8. Effects of cyclodextrin glycosiltransferase modified starch and cyclodextrins on plasma glucose and lipids metabolism in mice

    USDA-ARS?s Scientific Manuscript database

    The potential functional and nutritional benefits of granular starch treated with cyclodextrin glycosyltransferase (CGTase) and the released cyclodextrins (CDs) were explored in in vivo studies. The metabolic effects of diets in the C57BL/6J mouse containing native and enzymatically modified corn st...

  9. Complexation of sesquiterpene lactones with cyclodextrins: synthesis and effects on their activities on parasitic weeds.

    PubMed

    Cala, Antonio; Molinillo, José M G; Fernández-Aparicio, Mónica; Ayuso, Jesús; Álvarez, José A; Rubiales, Diego; Macías, Francisco A

    2017-08-09

    Allelochemicals are safer, more selective and more active alternatives than synthetic agrochemicals for weed control. However, the low solubility of these compounds in aqueous media limits their use as agrochemicals. Herein, we propose the application of α-, β- and γ-cyclodextrins to improve the physicochemical properties and biological activities of three sesquiterpene lactones: dehydrocostuslactone, costunolide and (-)-α-santonin. Complexation was achieved by kneading and coprecipitation methods. Aqueous solubility was increased in the range 100-4600% and the solubility-phase diagrams suggested that complex formation had been successful. The results of the PM3 semiempirical calculations were consistent with the experimental results. The activities on etiolated wheat coleoptiles, Standard Target Species and parasitic weeds were improved. Cyclodextrins preserved or enhanced the activity of the three sesquiterpene lactones. Free cyclodextrins did not show significant activity and therefore the enhancement in activity was due to complexation. These results are promising for applications in agrochemical design.

  10. Inhibition of Clostridium perfringens epsilon toxin by β-cyclodextrin derivatives.

    PubMed

    Robinson, Tanisha M; Jicsinszky, Laszlo; Karginov, Andrei V; Karginov, Vladimir A

    2017-10-15

    Clostridium perfringens epsilon toxin (ETX) is considered as one of the most dangerous potential biological weapons. The goal of this work was to identify inhibitors of ETX using a novel approach for the inactivation of pore-forming toxins. The approach is based on the blocking of the target pore with molecules having the same symmetry as the pore itself. About 200 various β-cyclodextrin derivatives were screened for inhibitors of ETX activity using a colorimetric cell viability assay. Several compounds with dose-dependent activities at low micromolar concentrations have been identified. The same compounds were also able to inhibit lethal toxin of Bacillus anthracis. Copyright © 2017 Elsevier B.V. All rights reserved.

  11. Sol-Gel Synthesis of Ordered β-Cyclodextrin-Containing Silicas

    NASA Astrophysics Data System (ADS)

    Trofymchuk, Iryna Mykolaivna; Roik, Nadiia; Belyakova, Lyudmila

    2016-03-01

    New approaches for β-cyclodextrin-containing silicas synthesis were demonstrated. Materials with hexagonally ordered mesoporous structure were prepared by postsynthesis grafting and by co-condensation methods. β-Cyclodextrin activated by a N, N'-carbonyldiimidazole was employed for postsynthesis treatment of 3-aminopropyl-modified MCM-41 support as well as for sol-gel synthesis with β-cyclodextrin-containing organosilane and tetraethyl orthosilicate participation in the presence of cetyltrimethylammonium bromide. The successful incorporation of cyclic oligosaccharide moieties in silica surface layer was verified by means of FT-IR spectroscopy and chemical analysis. Obtained β-cyclodextrin-containing materials were characterized by X-ray diffraction, transmission electron microscopy, and low-temperature adsorption-desorption of nitrogen. In spite of commensurable loading of β-cyclodextrin groups attained by both proposed approaches (up to 0.028 μmol · m-2), it was found that co-condensation procedure provides uniform distribution of β-cyclodextrin functionalities in silica framework, whereas postsynthesis grafting results in modification of external surface of silica surface. Adsorption of benzene from aqueous solutions onto the surface of β-cyclodextrin-containing materials prepared by co-condensation method was studied as the function of time and equilibrium concentration. Langmuir and Freundlich models were used to evaluate adsorption processes and parameters. Adsorption experiments showed that β-cyclodextrin-containing silicas could be promising for the trace amount removal of aromatics from water.

  12. Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer.

    PubMed

    Alsbaiee, Alaaeddin; Smith, Brian J; Xiao, Leilei; Ling, Yuhan; Helbling, Damian E; Dichtel, William R

    2016-01-14

    The global occurrence in water resources of organic micropollutants, such as pesticides and pharmaceuticals, has raised concerns about potential negative effects on aquatic ecosystems and human health. Activated carbons are the most widespread adsorbent materials used to remove organic pollutants from water but they have several deficiencies, including slow pollutant uptake (of the order of hours) and poor removal of many relatively hydrophilic micropollutants. Furthermore, regenerating spent activated carbon is energy intensive (requiring heating to 500-900 degrees Celsius) and does not fully restore performance. Insoluble polymers of β-cyclodextrin, an inexpensive, sustainably produced macrocycle of glucose, are likewise of interest for removing micropollutants from water by means of adsorption. β-cyclodextrin is known to encapsulate pollutants to form well-defined host-guest complexes, but until now cross-linked β-cyclodextrin polymers have had low surface areas and poor removal performance compared to conventional activated carbons. Here we crosslink β-cyclodextrin with rigid aromatic groups, providing a high-surface-area, mesoporous polymer of β-cyclodextrin. It rapidly sequesters a variety of organic micropollutants with adsorption rate constants 15 to 200 times greater than those of activated carbons and non-porous β-cyclodextrin adsorbent materials. In addition, the polymer can be regenerated several times using a mild washing procedure with no loss in performance. Finally, the polymer outperformed a leading activated carbon for the rapid removal of a complex mixture of organic micropollutants at environmentally relevant concentrations. These findings demonstrate the promise of porous cyclodextrin-based polymers for rapid, flow-through water treatment.

  13. Rapid removal of organic micropollutants from water by a porous β-cyclodextrin polymer

    NASA Astrophysics Data System (ADS)

    Alsbaiee, Alaaeddin; Smith, Brian J.; Xiao, Leilei; Ling, Yuhan; Helbling, Damian E.; Dichtel, William R.

    2016-01-01

    The global occurrence in water resources of organic micropollutants, such as pesticides and pharmaceuticals, has raised concerns about potential negative effects on aquatic ecosystems and human health. Activated carbons are the most widespread adsorbent materials used to remove organic pollutants from water but they have several deficiencies, including slow pollutant uptake (of the order of hours) and poor removal of many relatively hydrophilic micropollutants. Furthermore, regenerating spent activated carbon is energy intensive (requiring heating to 500-900 degrees Celsius) and does not fully restore performance. Insoluble polymers of β-cyclodextrin, an inexpensive, sustainably produced macrocycle of glucose, are likewise of interest for removing micropollutants from water by means of adsorption. β-cyclodextrin is known to encapsulate pollutants to form well-defined host-guest complexes, but until now cross-linked β-cyclodextrin polymers have had low surface areas and poor removal performance compared to conventional activated carbons. Here we crosslink β-cyclodextrin with rigid aromatic groups, providing a high-surface-area, mesoporous polymer of β-cyclodextrin. It rapidly sequesters a variety of organic micropollutants with adsorption rate constants 15 to 200 times greater than those of activated carbons and non-porous β-cyclodextrin adsorbent materials. In addition, the polymer can be regenerated several times using a mild washing procedure with no loss in performance. Finally, the polymer outperformed a leading activated carbon for the rapid removal of a complex mixture of organic micropollutants at environmentally relevant concentrations. These findings demonstrate the promise of porous cyclodextrin-based polymers for rapid, flow-through water treatment.

  14. Solution-state structure and affinities of cyclodextrin: Fentanyl complexes by nuclear magnetic resonance spectroscopy and molecular dynamics simulation

    DOE Office of Scientific and Technical Information (OSTI.GOV)

    Mayer, Brian P.; Kennedy, Daniel J.; Lau, Edmond Y.

    Cyclodextrins (CDs) are investigated for their ability to form inclusion complexes with the analgesic fentanyl and three similar molecules: acetylfentanyl, thiofentanyl, and acetylthiofentanyl. Stoichiometry, binding strength, and complex structure are revealed through nuclear magnetic resonance (NMR) techniques and discussed in terms of molecular dynamics (MD) simulations. It was found that β-cyclodextrin is generally capable of forming the strongest complexes with the fentanyl panel. Two-dimensional NMR data and computational chemical calculations are used to derive solution-state structures of the complexes. Binding of the fentanyls to the CDs occurs at the amide phenyl ring, leaving the majority of the molecule solvated bymore » water, an observation common to all four fentanyls. This finding suggests a universal binding behavior, as the vast majority of previously synthesized fentanyl analogues contain this structural moiety. Furthermore, this baseline study serves as the most complete work on CD:fentanyl complexes to date and provides the insights into strategies for producing future generations of designer cyclodextrins capable of stronger and more selective complexation of fentanyl and its analogues.« less

  15. Solution-state structure and affinities of cyclodextrin: Fentanyl complexes by nuclear magnetic resonance spectroscopy and molecular dynamics simulation

    DOE PAGES

    Mayer, Brian P.; Kennedy, Daniel J.; Lau, Edmond Y.; ...

    2016-02-04

    Cyclodextrins (CDs) are investigated for their ability to form inclusion complexes with the analgesic fentanyl and three similar molecules: acetylfentanyl, thiofentanyl, and acetylthiofentanyl. Stoichiometry, binding strength, and complex structure are revealed through nuclear magnetic resonance (NMR) techniques and discussed in terms of molecular dynamics (MD) simulations. It was found that β-cyclodextrin is generally capable of forming the strongest complexes with the fentanyl panel. Two-dimensional NMR data and computational chemical calculations are used to derive solution-state structures of the complexes. Binding of the fentanyls to the CDs occurs at the amide phenyl ring, leaving the majority of the molecule solvated bymore » water, an observation common to all four fentanyls. This finding suggests a universal binding behavior, as the vast majority of previously synthesized fentanyl analogues contain this structural moiety. Furthermore, this baseline study serves as the most complete work on CD:fentanyl complexes to date and provides the insights into strategies for producing future generations of designer cyclodextrins capable of stronger and more selective complexation of fentanyl and its analogues.« less

  16. Interactions between cyclodextrins and cellular components: Towards greener medical applications?

    PubMed Central

    2016-01-01

    In the field of host–guest chemistry, some of the most widely used hosts are probably cyclodextrins (CDs). As CDs are able to increase the water solubility of numerous drugs by inclusion into their hydrophobic cavity, they have been widespread used to develop numerous pharmaceutical formulations. Nevertheless, CDs are also able to interact with endogenous substances that originate from an organism, tissue or cell. These interactions can be useful for a vast array of topics including cholesterol manipulation, treatment of Alzheimer’s disease, control of pathogens, etc. In addition, the use of natural CDs offers the great advantage of avoiding or reducing the use of common petroleum-sourced drugs. In this paper, the general features and applications of CDs have been reviewed as well as their interactions with isolated biomolecules leading to the formation of inclusion or exclusion complexes. Finally, some potential medical applications are highlighted throughout several examples. PMID:28144335

  17. Characterization of a new TiF(4) and β-cyclodextrin inclusion complex and its in vitro evaluation on inhibiting enamel demineralization.

    PubMed

    Nassur, Camila; Alexandria, Adílis Kalina; Pomarico, Luciana; de Sousa, Valeria Pereira; Cabral, Lúcio Mendes; Maia, Lucianne Cople

    2013-03-01

    Titanium tetrafluoride (TiF(4)) is an effective but instable caries preventive agent. As the stability problems could be minimized through the use of drug carriers this study aimed to prepare and characterize a new TiF(4) nanoinclusion complex and to evaluate its potential in inhibiting enamel demineralization under pH cycling conditions. The TiF(4) nanosystems were prepared using β-cyclodextrin (βCD) and sodium montmorillonite (MMTNa). Bovine enamel blocks (n=48) with known surface microhardness (SMH), were randomly assigned to 4 groups (n=12) and submitted to one of the following treatments: distilled deionized water (as negative control) and solutions containing 1% βCD, 1% TiF(4) and TiF(4):βCD. The solutions were blinded applied once on the blocks with a microbrush(®) on the surface for 1min before pH-cycling. After that, samples were reavaluated by SMH, %SMH loss, cross-sectional microhardness (CSMH), scanning electron microscope (SEM) and energy dispersive spectrometry (EDX). The inclusion complex of TiF(4):βCD offered better protection against demineralization in the subsurface. The SEM analysis showed that TiF(4) and TiF(4):βCD samples presented the most intact enamel than the control. The EDX analysis identified titanium in TiF(4) and TiF(4):βCD groups. TiF(4):βCD has higher potential on inhibiting demineralization in the inner enamel. TiF(4):βCD is a new alternative to TiF(4) stabilization in order to reduce enamel subsurface demineralization. Copyright © 2012 Elsevier Ltd. All rights reserved.

  18. Insights into the multi-equilibrium, superstructure system based on β-cyclodextrin and a highly water soluble guest.

    PubMed

    De Paula, Elgte Elmin B; De Sousa, Frederico B; Da Silva, Júlio César C; Fernandes, Flaviana R; Melo, Maria Norma; Frézard, Frédéric; Grazul, Richard M; Sinisterra, Rubén D; Machado, Flávia C

    2012-12-15

    Pentamidine isethionate (PNT) is an antiprotozoal active in many cases of leishmaniasis, despite the present limitations including high toxicity and parenteral administration. In the present work, a PNT encapsulation strategy into β-cyclodextrin cavity at 1:1 and 2:1 (βCD:PNT) molar ratios was used in order to improve the drug's physical and chemical properties. Combining thermodynamic and structural approaches such as isothermal titration calorimetry (ITC), electrospray ionization mass spectrometry (ESI-MS) and nuclear magnetic resonance ((1)H NMR, and ROESY) the inclusion process and the thermodynamics parameters were identified. ITC and ESI-MS experimental data suggest the simultaneous formation of different supramolecular complexes in solution. Moreover, NMR data are in accordance with these results, suggesting a deep inclusion of PNT into the βCD cavity, through correlations observed in 2D ROESY contour maps. The systems were also characterized by FTIR, TG/DTA and SEM. These techniques indicate the formation of inclusion complex in the solid state. In vivo PNT activity was evaluated orally in mice. The inclusion complex showed a significant reduction of parasite load compared to free PNT. Copyright © 2012 Elsevier B.V. All rights reserved.

  19. Intramolecular Oxidative O-Demethylation of an Oxoferryl Porphyrin Complexed with a Per-O-methylated β-Cyclodextrin Dimer.

    PubMed

    Kitagishi, Hiroaki; Kurosawa, Shun; Kano, Koji

    2016-11-22

    The intramolecular oxidation of ROCH 3 to ROCH 2 OH, where the latter compound spontaneously decomposed to ROH and HCHO, was observed during the reaction of the supramolecular complex (met-hemoCD3) with cumene hydroperoxide in aqueous solution. Met-hemoCD3 is composed of meso-tetrakis(4-sulfonatophenyl)porphinatoiron(III) (Fe III TPPS) and a per-O-methylated β-cyclodextrin dimer having an -OCH 2 PyCH 2 O- linker (Py=pyridine-3,5-diyl). The O=Fe IV TPPS complex was formed by the reaction of met-hemoCD3 with cumene hydroperoxide, and isolated by gel-filtration chromatography. Although the isolated O=Fe IV TPPS complex in the cyclodextrin cage was stable in aqueous solution at 25 °C, it was gradually converted to Fe II TPPS (t 1/2 =7.6 h). This conversion was accompanied by oxidative O-demethylation of an OCH 3 group in the cyclodextrin dimer. The results indicated that hydrogen abstraction by O=Fe IV TPPS from ROCH 3 yields HO-Fe III TPPS and ROCH 2 . . This was followed by radical coupling to afford Fe II TPPS and ROCH 2 OH. The hemiacetal (ROCH 2 OH) immediately decomposed to ROH and HCHO. This study revealed the ability of oxoferryl porphyrin to induce two-electron oxidation. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

  20. Functionalization of Cyclodextrins with N-Hydroxyphthalimide Moiety: A New Class of Supramolecular Pro-Oxidant Organocatalysts.

    PubMed

    Melone, Lucio; Petroselli, Manuel; Pastori, Nadia; Punta, Carlo

    2015-08-31

    N-hydroxyphthalimide (NHPI) is an organocatalyst for free-radical processes able to promote the aerobic oxidation of a wide range of organic substrates. In particular, NHPI can catalyze the hydroperoxidation of polyunsaturated fatty acids (PUFA). This property could be of interest for biological applications. This work reports the synthesis of two β-cyclodextrin derivatives (CD5 and CD6) having a different degree of methylation and bearing a NHPI moiety. These compounds, having different solubility in water, have been successfully tested for the hydroperoxidation of methyl linoleate, chosen as the PUFA model molecule.

  1. Functional electrospun polystyrene nanofibers incorporating α-, β-, and γ-cyclodextrins: comparison of molecular filter performance.

    PubMed

    Uyar, Tamer; Havelund, Rasmus; Hacaloglu, Jale; Besenbacher, Flemming; Kingshott, Peter

    2010-09-28

    Electrospinning has been used to successfully create polystyrene (PS) nanofibers containing either of three different types of cyclodextrin (CD); α-CD, β-CD, and γ-CD. These three CDs are chosen because they have different sized cavities that potentially allow for selective inclusion complex (IC) formation with molecules of different size or differences in affinity of IC formation with one type of molecule. The CD containing electrospun PS nanofibers (PS/CD) were initially characterized by scanning electron microscopy (SEM) to determine the uniformity of the fibers and their fiber diameter distributions. X-ray photoelectron spectroscopy (XPS) was used to quantitatively determine the concentration of each CD on the different fiber surfaces. Static time-of-flight secondary ion mass spectrometry (static-ToF-SIMS) showed the presence of each type of CD on the PS nanofibers by the detection of both the CD sodium adduct molecular ions (M + Na+) and lower molecular weight oxygen containing fragment ions. The comparative efficiency of the PS/CD nanofibers/nanoweb for removing phenolphthalein, a model organic compound, from solution was determined by UV-vis spectrometry, and the kinetics of phenolphthalein capture was shown to follow the trend PS/α-CD > PS/β-CD > PS/γ-CD. Direct pyrolysis mass spectrometry (DP-MS) was also performed to ascertain the relative binding strengths of the phenolphthalein for the CD cavities, and the results showed the trend in the interaction strength was β-CD > γ-CD > α-CD. Our results demonstrate that nanofibers produced by electrospinning that incorporate cyclodextrins with different sized cavities can indeed filter organic molecules and can potentially be used for filtration, purification, and/or separation processes.

  2. Impact of beta-cyclodextrin and resistant starch on bile acid metabolism and fecal steroid excretion in regard to their hypolipidemic action in hamsters.

    PubMed

    Trautwein, E A; Forgbert, K; Rieckhoff, D; Erbersdobler, H F

    1999-01-29

    To examine the impact on bile acid metabolism and fecal steroid excretion as a mechanism involved in the lipid-lowering action of beta-cyclodextrin and resistant starch in comparison to cholestyramine, male golden Syrian hamsters were fed 0% (control), 8% or 12% of beta-cyclodextrin or resistant starch or 1% cholestyramine. Resistant starch, beta-cyclodextrin and cholestyramine significantly lowered plasma total cholesterol and triacylglycerol concentrations compared to control. Distinct changes in the bile acid profile of gallbladder bile were caused by resistant starch, beta-cyclodextrin and cholestyramine. While cholestyramine significantly reduced chenodeoxycholate independently of its taurine-glycine conjugation, beta-cyclodextrin and resistant starch decreased especially the percentage of taurochenodeoxycholate by -75% and -44%, respectively. As a result, the cholate:chenodeoxycholate ratio was significantly increased by 100% with beta-cyclodextrin and by 550% with cholestyramine while resistant starch revealed no effect on this ratio. beta-Cyclodextrin and resistant starch, not cholestyramine, significantly increased the glycine:taurine conjugation ratio demonstrating the predominance of glycine conjugated bile acids. Daily fecal excretion of bile acids was 4-times higher with 8% beta-cyclodextrin and 19-times with 1% cholestyramine compared to control. beta-Cyclodextrin and cholestyramine also induced a 2-fold increase in fecal neutral sterol excretion, demonstrating the sterol binding capacity of these two compounds. Resistant starch had only a modest effect on fecal bile acid excretion (80% increase) and no effect on excretion of neutral sterols, suggesting a weak interaction with intestinal steroid absorption. These data demonstrate the lipid-lowering potential of beta-cyclodextrin and resistant starch. An impaired reabsorption of circulating bile acids and intestinal cholesterol absorption leading to an increase in fecal bile acid and neutral sterol

  3. Characterization of the host-guest complex of a curcumin analog with β-cyclodextrin and β-cyclodextrin-gemini surfactant and evaluation of its anticancer activity.

    PubMed

    Poorghorban, Masoomeh; Das, Umashankar; Alaidi, Osama; Chitanda, Jackson M; Michel, Deborah; Dimmock, Jonathan; Verrall, Ronald; Grochulski, Pawel; Badea, Ildiko

    2015-01-01

    Curcumin analogs, including the novel compound NC 2067, are potent cytotoxic agents that suffer from poor solubility, and hence, low bioavailability. Cyclodextrin-based carriers can be used to encapsulate such agents. In order to understand the interaction between the two molecules, the physicochemical properties of the host-guest complexes of NC 2067 with β-cyclodextrin (CD) or β-cyclodextrin-gemini surfactant (CDgemini surfactant) were investigated for the first time. Moreover, possible supramolecular structures were examined in order to aid the development of new drug delivery systems. Furthermore, the in vitro anticancer activity of the complex of NC 2067 with CDgemini surfactant nanoparticles was demonstrated in the A375 melanoma cell line. Physicochemical properties of the complexes formed of NC 2067 with CD or CDgemini surfactant were investigated by synchrotron-based powder X-ray diffraction, Fourier-transform infrared spectroscopy, and thermogravimetric analysis. Synchrotron-based small- and wide-angle X-ray scattering and size measurements were employed to assess the supramolecular morphology of the complex formed by NC 2067 with CDgemini surfactant. Lastly, the in vitro cell toxicity of the formulations toward A375 melanoma cells at various drug-to-carrier mole ratios were measured by cell viability assay. Physical mixtures of NC 2067 and CD or CDgemini surfactant showed characteristics of the individual components, whereas the complex of NC 2067 and CD or CDgemini surfactant presented new structural features, supporting the formation of the host-guest complexes. Complexes of NC 2067 with CDgemini surfactants formed nanoparticles having sizes of 100-200 nm. NC 2067 retained its anticancer activity in the complex with CDgemini surfactant for different drug-to-carrier mole ratios, with an IC50 (half-maximal inhibitory concentration) value comparable to that for NC 2067 without the carrier. The formation of host-guest complexes of NC 2067 with CD or

  4. Complexes between methyltestosterone and β-cyclodextrin for application in aquaculture production.

    PubMed

    Carvalho, Lucas Bragança de; Burusco, Kepa Koldo; Jaime, Carlos; Venâncio, Tiago; Carvalho, Aline Ferreira Souza de; Murgas, Luis David Solis; Pinto, Luciana de Matos Alves

    2018-01-01

    The inclusion complexes between 17-α-methyltestosterone (MT) and β-cyclodextrin (bCD) were prepared and characterized in dissolution and solid phase. The complex promoted a sixfold increment in solubility of the hormone. It has a limited solubility and stoichiometry of 2:1 (bCD:MT) determined by DSC, NMR and solubility experiments, the association constant Ka=2846Lmol -1 and complex fraction of 76% (assessed by DOSY-NMR, in (1:3) DMSO/D 2 O). The association constant obtained in water by the solubility isotherms is 7540Lmol -1 . 2D-ROESY experiments indicate the intermolecular orientation (complete inclusion of the hormone in the cavity). Simulations by molecular dynamics agreed with the formation of the inclusion complex 2:1. Release tests showed the slower release for the complexes, with 50% for lyophilization and 56% for malaxation. These results clearly demonstrate the complexation of MT in bCD, which formulations are promising for further applications involving this steroid in aquaculture, both for sexual reversal and in technologies of hormone in water sequestration. Copyright © 2017 Elsevier Ltd. All rights reserved.

  5. Exploiting β-Cyclodextrin in Molecular Imprinting for Achieving Recognition of Benzylparaben in Aqueous Media

    PubMed Central

    Asman, Saliza; Mohamad, Sharifah; Muhamad Sarih, Norazilawati

    2015-01-01

    The molecularly imprinted polymer (MIP) based on methacrylic acid functionalized β-cyclodextrin (MAA-β-CD) monomer was synthesized for the purpose of selective recognition of benzylparaben (BzP). The MAA-β-CD monomer was produced by bridging a methacrylic acid (MAA) and β-cyclodextrin (β-CD) using toluene-2,4-diisocyanate (TDI) by reacting the –OH group of MAA and one of the primary –OH groups of β-CD. This monomer comprised of triple interactions that included an inclusion complex, π–π interaction, and hydrogen bonding. To demonstrate β-CD performance in MIPs, two MIPs were prepared; molecularly imprinted polymer-methacrylic acid functionalized β-cyclodextrin, MIP(MAA-β-CD), and molecularly imprinted polymer-methacrylic acid, MIP(MAA); both prepared by a reversible addition fragmentation chain transfer polymerization (RAFT) in the bulk polymerization process. Both MIPs were characterized using the Fourier Transform Infrared Spectroscopy (FTIR), Field Emission Scanning Electron Microscopy (FESEM), and Brunauer-Emmett-Teller (BET). The presence of β-CD not only influenced the morphological structure, it also affected the specific surface area, average pore diameter, and total pore volume of the MIP. The rebinding of the imprinting effect was evaluated in binding experiments, which proved that the β-CD contributed significantly to the enhancement of the recognition affinity and selective adsorption of the MIP. PMID:25667978

  6. Elaboration of antibiofilm surfaces functionalized with antifungal-cyclodextrin inclusion complexes.

    PubMed

    Gharbi, Aïcha; Humblot, Vincent; Turpin, Frédéric; Pradier, Claire-Marie; Imbert, Christine; Berjeaud, Jean-Marc

    2012-07-01

    To tackle the loss of activity of surfaces functionalized by coating and covalently bound molecules to materials, an intermediate system implying the noncovalent immobilization of active molecules in the inner cavity of grafted cyclodextrins (CDs) was investigated. The antifungal and antibiofilm activities of the most stable complexes of Anidulafungin (ANF; echinocandin) and thymol (THY; terpen) in various CDs were demonstrated to be almost the same as the free molecules. The selected CD was covalently bond to self-assembled monolayers on gold surfaces. The immobilized antifungal agents reduced the number of culturable Candida albicans ATCC 3153 attached to the surface by 64 ± 8% for ANF and 75 ± 15% for THY. The inhibitory activity was persistent for THY-loaded samples, whereas it was completely lost for ANF-loaded surfaces after one use. However, reloading of the echinocandin restored the activity. Using fluorescent dying and confocal microscopy, it was proposed that the ANF-loaded surfaces inhibited the adherence of the yeasts, whereas the activity of immobilized THY was found fungicidal. This kind of tailored approach for functionalizing surfaces that could allow a progressive release of ANF or THY gave promising results but still needs to be improved to display a full activity. © 2012 Federation of European Microbiological Societies. Published by Blackwell Publishing Ltd. All rights reserved.

  7. Direct investigation of the vectorization properties of amphiphilic cyclodextrins in phospholipid films.

    PubMed

    Javierre, Isabelle; Nedyalkov, Mickael; Petkova, Vera; Benattar, Jean Jacques; Weisse, Sandrine; Auzély-Velty, Rachel; Djedaïni-Pilard, Florence; Perly, Bruno

    2002-10-01

    Recently, new cyclodextrin derivatives were synthesized and shown to exhibit strong amphiphilic properties. In this paper, we study the action of these new amphiphilic cyclodextrins on phospholipids. Mixed phospholipid/cyclodextrin derivative films were prepared and studied using X-ray reflectivity for various phospholipid/cyclodextrin ratios. A molar ratio of 3 provides a highly stable film the molecular structure of which has been investigated in detail. The cholesterol tail of the cyclodextrin molecule was found to be anchored into the phospholipid film. The cyclodextrin moieties exposed to the aqueous medium are prone to the addition of the guest molecule Dosulepin, making them of high interest for drug delivery. For this purpose and as an example of a potential application, this cyclodextrin molecular carrier property is also addressed to this complex film architecture.

  8. Combined use of chiral ionic liquid surfactants and neutral cyclodextrins: evaluation of ionic liquid head groups for enantioseparation of neutral compounds in capillary electrophoresis.

    PubMed

    Liu, Yijin; Shamsi, Shahab A

    2014-09-19

    Cyclodextrins (CDs) are most commonly used chiral selectors in capillary electrophoresis (CE). Although the use of neutral CDs and its derivatives have shown to resolve plethora of charged enantiomers, they cannot resolve neutral enantiomers. The use of ionic liquids (ILs) surfactants forming successful complex with CDs present itself an opportunity to resolve neutral enantiomers. In this work, the effect of IL head groups and their complexation ability with heptakis (2,3,6-tri-O-methyl)-β-cyclodextrin (TM-β-CD) was studied for the separation of neutral enantiomers by CE. First, cationic IL type surfactants with different chiral head groups were synthesized. Physicochemical properties such as critical micelle concentration were determined by surface tension, whereas aggregation and polarity were determined by fluorescence spectroscopy. The complexation ability of ILs with TM-β-CD was characterized in the gas phase by CE-mass spectrometry. The influence of the type of ILs head group and its concentration on chiral resolution, resolution per unit time and selectivity were investigated for four structurally diverse neutral compounds. The binding constants of the neutral analytes to the IL-CD complex were estimated by y-reciprocal method. The hydrophobicity of the side chain of the IL head group displayed significant effect on the binding constants and enantioseparations. Copyright © 2014 Elsevier B.V. All rights reserved.

  9. Effect of Foods and β-Cyclodextrin on the Bioaccessibility and the Uptake by Caco-2 Cells of Hydroxytyrosol from Either a Pure Standard or Alperujo.

    PubMed

    Malapert, Aurélia; Tomao, Valérie; Dangles, Olivier; Reboul, Emmanuelle

    2018-05-09

    Hydroxytyrosol bioaccessibility and absorption by the intestinal cells were studied using an in vitro digestion model and Caco-2 TC7 monolayers cells in culture in the presence and absence of β-cyclodextrin and foods. Hydroxytyrosol was either provided as a pure standard or in an alperujo powder. The presence of foods significantly decreased hydroxytyrosol bioaccessibility and absorption (-20 and -10%, respectively), while β-cyclodextrin had no effect. Moreover, the presence of other compounds from alperujo in the intestinal compartment reduced hydroxytyrosol absorption by Caco-2 cells compared to pure standard (-60%). The final bioavailability of hydroxytyrosol, defined as its quantity at the basolateral side of cultured cell monolayers compared to the initial amount in the test meal, was 6.9 ± 0.4, 31.1 ± 1.1, and 40.9 ± 1.5% when hydroxytyrosol was from alperujo or a standard administered with or without food, respectively. Our results show that conversely to foods, β-cyclodextrin does not alter hydroxytyrosol bioavailability.

  10. Comparison of Positively and Negatively Charged Achiral Co-Monomers Added to Cyclodextrin Monolith: Improved Chiral Separations in Capillary Electrochromatography

    PubMed Central

    Lu, Yang; Shamsi, Shahab A.

    2014-01-01

    Cyclodextrins (CDs) and their derivatives have been one of the most popular and successful chiral additives used in electrokinetic chromatography because of the presence of multiple chiral centers, which leads to multiple chiral interactions. However, there has been relatively less published work on the use of CDs as monolithic media for capillary electrochromatography (CEC). The goal of this study was to show how the addition of achiral co-monomer to a polymerizable CD such as glycidyl methacrylate β-cyclodextrin (GMA/β-CD) can affect the enantioselective separations in monolithic CEC. To achieve this goal, polymeric monoliths columns were prepared by co-polymerizing GMA/β-CD with cationic or anionic achiral co-monomers [(2-acrylamido-2-methyl-1-propanesulfonic acid (AMPS) and vinyl benzyltrimethyl-ammonium (VBTA)] in the presence of conventional crosslinker (ethylene dimethacrylate) and ternary porogen system including butanediol, propanol and water. A total of 34 negatively charged compounds, 30 positively charged compounds and 33 neutral compounds were screened to compare the enantioresolution capability on the GMA/β-CD, GMA/β-CD-VBTA and GMA/β-CD-AMPS monolithic columns. PMID:24108813

  11. Encapsulation of labetalol, pseudoephedrine in β-cyclodextrin cavity: spectral and molecular modeling studies.

    PubMed

    Prabhu, A Antony Muthu; Rajendiran, N

    2012-11-01

    The absorption and fluorescence spectra of labetalol and pseudoephedrine have been studied in different polarities of solvents and β-cyclodextrin (β-CD). The inclusion complexation with β-CD is investigated by UV-visible, steady state and time resolved fluorescence spectra and PM3 method. In protic solvents, the normal emission originates from a locally excited state and the longer wavelength emission is due to intramolecular charge transfer (TICT). Labetalol forms a 1:2 complex and pseudoephedrine forms 1:1 complex with β-CD. Nanosecond time-resolved studies indicated that both molecules show triexponential decay. Thermodynamic parameters (ΔG, ΔH, ΔS) and HOMO, LUMO orbital investigations confirm the stability of the inclusion complex. The geometry of the most stable complex shows that the aromatic ring is deeply self included inside the β-CD cavity and intermolecular hydrogen bonds were established between host and guest molecules. This suggests that hydrophobic effect and hydrogen bond play an important role in the inclusion process.

  12. Chemical microsensors

    DOEpatents

    Li, DeQuan; Swanson, Basil I.

    1995-01-01

    An article of manufacture is provided including a substrate having an oxide surface layer and a selective thin film of a cyclodextrin derivative chemically bound upon said substrate, said film is adapted for the inclusion of a selected organic compound therewith. Such an article can be either a chemical sensor capable of detecting a resultant mass change from inclusion of the selected organic compound or a chemical separator capable of reversibly selectively separating a selected organic compound.

  13. Nootkatone encapsulation by cyclodextrins: Effect on water solubility and photostability.

    PubMed

    Kfoury, Miriana; Landy, David; Ruellan, Steven; Auezova, Lizette; Greige-Gerges, Hélène; Fourmentin, Sophie

    2017-12-01

    Nootkatone (NO) is a sesquiterpenoid volatile flavor, used in foods, cosmetics and pharmaceuticals, possessing also insect repellent activity. Its application is limited because of its low aqueous solubility and stability; this could be resolved by encapsulation in cyclodextrins (CDs). This study evaluated the encapsulation of NO by CDs using phase solubility studies, Isothermal Titration Calorimetry, Nuclear Magnetic Resonance spectroscopy and molecular modeling. Solid CD/NO inclusion complex was prepared and characterized for encapsulation efficiency and loading capacity using UV-Visible. Thermal properties were investigated by thermogravimetric-differential thermal analysis and release studies were performed using multiple headspace extraction. Formation constants (K f ) proved the formation of stable inclusion complexes. NO aqueous solubility, photo- and thermal stability were enhanced and the release could be insured from solid complex in aqueous solution. This suggests that CDs are promising carrier to improve NO properties and, consequently, to enlarge its use in foods, cosmetics, pharmaceuticals and agrochemicals preparations. Copyright © 2016 Elsevier Ltd. All rights reserved.

  14. Coupling of non-aqueous electrokinetic chromatography using cationic cyclodextrins with electrospray ionization mass spectrometry.

    PubMed

    Mol, Roelof; de Jong, Gerhardus J; Somsen, Govert W

    2008-01-01

    Non-aqueous electrokinetic chromatography (NAEKC) using cationic cyclodextrins (CDs) was coupled to electrospray ionization mass spectrometry (ESI-MS). A methanolic background electrolyte (BGE) was used which contained the hydrochloride salts of the single-isomer derivative cyclodextrins 6-monodeoxy-6-mono(2-hydroxy)propylamino-beta-cyclodextrin (IPA-beta-CD) or 6-monodeoxy-6-mono(3-hydroxy)propylamino-beta-cyclodextrin (PA-beta-CD). Applying a reversed capillary electrophoresis (CE) polarity (-30 kV), efficient separation of negatively charged compounds was achieved with plate numbers of up to 190,000. PA-beta-CD appeared to be the most suitable for the separation of various acidic drugs while also providing a high chiral selectivity. Analyte detection was achieved by ESI-MS in the negative-ion mode using a sheath-liquid interface. In order to prevent current drops caused by the cathodic electroosmotic flow, a pressure of 15 mbar was applied on the inlet vial during NAEKC/MS analysis. The effect of the cationic CDs on the MS signal intensities of acidic test drugs was thoroughly studied. When a voltage is applied across the CE capillary, the overall mobility of the cationic CDs is towards the inlet vial so that no CD molecules enter the ion source. The chloride counter ions of the CDs, which migrated towards the capillary outlet, were found to cause ionization suppression, although significant analyte signals could still be detected. Depending on the CD concentration in the BGE, limits of detection for acidic drugs were in the 50-400 ng/mL range in full-scan mode.

  15. Characterization of inclusion complexes of organic ions with hydrophilic hosts by ion transfer voltammetry with solvent polymeric membranes.

    PubMed

    Olmos, José Manuel; Laborda, Eduardo; Ortuño, Joaquín Ángel; Molina, Ángela

    2017-03-01

    The quantitative characterization of inclusion complexes formed in aqueous phase between organic ions and hydrophilic hosts by ion-transfer voltammetry with solvent polymeric membrane ion sensors is studied, both in a theoretical and experimental way. Simple analytical solutions are presented for the determination of the binding constant of the complex from the variation with the host concentration of the electrochemical signal. These solutions are valid for any voltammetric technique and for solvent polymeric membrane ion sensors comprising one polarisable interface (1PI) and also, for the first time, two polarisable interfaces (2PIs). Suitable experimental conditions and data analysis procedures are discussed and applied to the study of the interactions of a common ionic liquid cation (1-octyl-3-metyl-imidazolium) and an ionisable drug (clomipramine) with two hydrophilic cyclodextrins: α-cyclodextrin and 2-hydroxypropyl-β-cyclodextrin. The experimental study is performed via square wave voltammetry with 2PIs and 1PI solvent polymeric membranes and in both cases the electrochemical experiments enable the detection of inclusion complexes and the determination of the corresponding binding constant. Copyright © 2016 Elsevier B.V. All rights reserved.

  16. Development of biosensor for phenolic compounds containing PPO in β-cyclodextrin modified support and iridium nanoparticles.

    PubMed

    da Silva, Cristiano P; Franzoi, Ana C; Fernandes, Suellen C; Dupont, Jairton; Vieira, Iolanda C

    2013-04-10

    A biosensor based on the iridium nanoparticles dispersed in ionic liquid (IL) 1-butyl-3-methylimidazolium hexafluorophosphate (Ir-BMI·PF6) and a celery (Apium graveolens) extract as a source of polyphenol oxidase (PPO) was constructed. A modified support based on β-cyclodextrin (β-CDEP) was used for enzyme immobilization. The behavior of phenolic compounds was investigated by square-wave voltammetry and rutin was selected by presenting the greatest signal. The best performance was obtained with a composition of 70:10:10:10% (w/w/w/w) of the graphite powder:β-CDEP:Nujol:Ir-BMI·PF6 composition, a PPO concentration of 500unitsmL(-1), in 0.1M phosphate buffer solution (pH 6.0) with frequency, pulse amplitude and scan increment at 100Hz, 60mV, and 3.0mV, respectively. Under optimized conditions, the cathodic currents increased linearly for the rutin concentration range of 1.3×10(-7)-2.0×10(-6)M with a detection limit of 7.9×10(-8)M. This sensor demonstrated acceptable repeatability and reproducibility and the results for the rutin recovery ranged from 92.8 to 103.4%. A relative error of 0.7% was obtained in the rutin determination in simulated samples. Copyright © 2013 Elsevier Inc. All rights reserved.

  17. Self-assembly behavior of β-cyclodextrin and imipramine. A Free energy perturbation study

    NASA Astrophysics Data System (ADS)

    Sun, Tingting; Shao, Xueguang; Cai, Wensheng

    2010-05-01

    The self-assembly behavior of β-cyclodextrin (β-CD) and imipramine (IMI), an antidepressant drug, was investigated by molecular dynamics simulations in the gas phase and in an aqueous solution. The binding free energies for 10 possible arrangements of β-CD/IMI complexes with stoichiometries of 1:1, 2:1, and 1:2 were determined using free energy perturbation calculations. The calculations suggest that the 2:1 inclusion mode is the most energetically favored in both phases, in good agreement with experiment. The environment and the neutral and charged IMI influence the stability of the aggregates. The electrostatic interactions constitute the main contribution to the stability. The results reported in this contribution shed new light on the mechanism of association of β-CD with IMI.

  18. Optimization of β-cyclodextrin cross-linked polymer for monitoring of quercetin

    NASA Astrophysics Data System (ADS)

    Zhu, Xiashi; Ping, Wenhui

    2014-11-01

    A novel method for the separation/analysis of quercetin was described, which was based on the investigation of the inclusion interactions of β-cyclodextrin cross-linked polymer (β-CDCP) with quercetin (Qu) and the adsorption behavior of Qu on β-CDCP. The inclusion interaction of β-CDCP with Qu was studied through FTIR, TGA and 13C NMR. Under the optimum conditions, the preconcentration factor of the proposed method was approximately 8.8, the β-CDCP could be used repeatedly for 30 times and offered better recovery. The linear range, limit of detection (LOD) and the relative standard deviation (RSD) was found to be 0.10-12.0 μg mL-1, 4.6 ng mL-1 and 3.10% (n = 3, c = 2.0 μg mL-1) respectively. This technique had been successfully applied to the determination of Qu in real samples.

  19. Solubilization of ibuprofen with β-cyclodextrin derivatives: energetic and structural studies.

    PubMed

    di Cagno, Massimiliano; Stein, Paul C; Skalko-Basnet, Nataša; Brandl, Martin; Bauer-Brandl, Annette

    2011-06-01

    The aim of this work was to investigate the complexation of ibuprofen as model drug with various β-cyclodextrins (native β-cyclodextrin, hydroxypropyl-β-cyclodextrin with two different molar degrees of substitution, and methyl-β-cyclodextrin). Solutions of the commercially available β-cyclodextrins were prepared in phosphate buffer (73mM). The pH value was adjusted to 7.4 and the solutions were isotonized with NaCl. A solution of ibuprofen was prepared in the same way. A thermal activity monitor was used for isothermal titration calorimetry (ITC). (1)H NMR analysis was employed to investigate the structures of the complexes. ITC analysis showed that each type of β-cyclodextrin had its characteristic values of both enthalpy and mass equilibrium constant for the complexation processes with the drug molecules. (1)H NMR spectroscopy of the complexes showed through significant differences in chemical shifts that the physical interaction between the cyclodextrins and ibuprofen molecules were also different, probably due to different three-dimensional arrangements of ibuprofen in the cyclodextrin cavity, induced by the different substituents bonded to the glucose rings. These differences were connected to the thermodynamic parameters of the complexes. Copyright © 2011 Elsevier B.V. All rights reserved.

  20. Compound ultrarefractory CAI-bearing inclusions from CV3 carbonaceous chondrites

    NASA Astrophysics Data System (ADS)

    Ivanova, Marina A.; Krot, Alexander N.; Nagashima, Kazuhide; MacPherson, Glenn J.

    2012-12-01

    Abstract-Two <span class="hlt">compound</span> calcium-aluminum-rich <span class="hlt">inclusions</span> (CAIs), 3N from the oxidized CV chondrite Northwest Africa (NWA) 3118 and 33E from the reduced CV chondrite Efremovka, contain ultrarefractory (UR) <span class="hlt">inclusions</span>. 3N is <span class="hlt">a</span> forsterite-bearing type B (FoB) CAI that encloses UR <span class="hlt">inclusion</span> 3N-24 composed of Zr,Sc,Y-rich oxides, Y-rich perovskite, and Zr,Sc-rich Al,Ti-diopside. 33E contains <span class="hlt">a</span> fluffy type <span class="hlt">A</span> (FTA) CAI and UR CAI 33E-1, surrounded by Wark-Lovering rim layers of spinel, Al-diopside, and forsterite, and <span class="hlt">a</span> common forsterite-rich accretionary rim. 33E-1 is composed of Zr,Sc,Y-rich oxides, Y-rich perovskite, Zr,Sc,Y-rich pyroxenes (Al,Ti-diopside, Sc-rich pyroxene), and gehlenite. 3N-24's UR oxides and Zr,Sc-rich Al,Ti-diopsides are 16O-poor (Δ17O approximately -2‰ to -5‰). Spinel in 3N-24 and spinel and Al-diopside in the FoB CAI are 16O-rich (Δ17O approximately -23 ± 2‰). 33E-1's UR oxides and Zr,Sc-rich Al,Ti-diopsides are 16O-depleted (Δ17O approximately -2‰ to -5‰) vs. Al,Ti-diopside of the FTA CAI and spinel (Δ17O approximately -23 ± 2‰), and Wark-Lovering rim Al,Ti-diopside (Δ17O approximately -7‰ to -19‰). We infer that the <span class="hlt">inclusions</span> experienced multistage formation in nebular regions with different oxygen-isotope compositions. 3N-24 and 33E-1's precursors formed by evaporation/condensation above 1600 °C. 3N and 33E's precursors formed by condensation and melting (3N only) at significantly lower temperatures. 3N-24 and 3N's precursors aggregated into <span class="hlt">a</span> <span class="hlt">compound</span> object and experienced partial melting and thermal annealing. 33E-1 and 33E avoided melting prior to and after aggregation. They acquired Wark-Lovering and common forsterite-rich accretionary rims, probably by condensation, followed by thermal annealing. We suggest 3N-24 and 33E-1 originated in <span class="hlt">a</span> 16O-rich gaseous reservoir and subsequently experienced isotope exchange in <span class="hlt">a</span> 16O-poor gaseous reservoir. Mechanism and timing of oxygen-isotope exchange remain</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_15");'>15</a></li> <li><a href="#" onclick='return showDiv("page_16");'>16</a></li> <li class="active"><span>17</span></li> <li><a href="#" onclick='return showDiv("page_18");'>18</a></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_17 --> <div id="page_18" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_16");'>16</a></li> <li><a href="#" onclick='return showDiv("page_17");'>17</a></li> <li class="active"><span>18</span></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="341"> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/14592694','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/14592694"><span>The effect of pH and triethanolamine on sulfisoxazole complexation with hydroxypropyl-beta-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Gladys, Granero; Claudia, Garnero; Marcela, Longhi</p> <p>2003-11-01</p> <p><span class="hlt">A</span> novel complexation of sulfisoxazole with hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> (HP-beta-CD) was studied. Two systems were used: binary complexes prepared with HP-beta-CD and multicomponent system (HP-beta-CD and the basic <span class="hlt">compound</span> triethanolamine (TEA)). <span class="hlt">Inclusion</span> complex formation in aqueous solutions and in solid state were investigated by the solubility method, thermal analysis (differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA)), Fourier-transform infrared spectroscopy (FT-IR) and dissolution studies. The solid complexes of sulfisoxazole were prepared by freeze-drying the homogeneous concentrated aqueous solutions in molar ratios of sulfisoxazole:HP-beta-CD 1:1 and 1:2, and sulfisoxazole:TEA:HP-beta-CD 1:1:2. FT-IR and thermal analysis showed differences among sulfisoxazole:HP-beta-CD and sulfisoxazole:TEA:HP-beta-CD and their corresponding physical mixtures and individual components. The HP-beta-CD solubilization of sulfisoxazole could be improved by ionization of the drug molecule through pH adjustments. However, larger improvements of the HP-beta-CD solubilization are obtained when multicomponent systems are used, allowing to reduce the amount of CD necessary to prepare the target formulation.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25728864','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25728864"><span>β-<span class="hlt">cyclodextrin</span> in personal care formulations: role on the complexation of malodours causing molecules.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Lopedota, A; Cutrignelli, A; Laquintana, V; Franco, M; Donelli, D; Ragni, L; Tongiani, S; Denora, N</p> <p>2015-08-01</p> <p>The aim of this study was to prove the capability of β-<span class="hlt">cyclodextrin</span> (β-CD) to interact with some representative molecules responsible to cause body malodour, such as carboxylic acids, thiols and steroids, present in sweat and body secretions. The association constants in guest-CD were determined by (1) H-NMR spectroscopy for thiols and steroids such as 3-mercapto-1-hexanol, androstenone, androstenol and androsterone, and pH-potentiometric titration for acetic acid, l(+) lactic acid, isobutyric acid, isovaleric acid and 3-hydroxy-3-methyl-hexanoic acid. All considered systems are able to interact with relatively weak association constants with β-<span class="hlt">cyclodextrin</span>, in <span class="hlt">a</span> 1 : 1 host-guest ratio. From these findings, it is possible to conclude that β-CD is capable to interact with different components present in the sweat and body secretion, forming <span class="hlt">inclusion</span> complexes. For this reason, β-CD could be <span class="hlt">a</span> component of body care formulations, such as deodorants. © 2015 Society of Cosmetic Scientists and the Société Française de Cosmétologie.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/18177023','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/18177023"><span>Hartree-Fock and density functional theory study of alpha-<span class="hlt">cyclodextrin</span> conformers.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Jiménez, Verónica; Alderete, Joel B</p> <p>2008-01-31</p> <p>Herein, we report the geometry optimization of four conformers of alpha-<span class="hlt">cyclodextrin</span> (alpha-CD) by means of PM3, HF/STO-3G, HF/3-21G, HF/6-31G(d), B3LYP/6-31G(d), and X3LYP/6-31G(d) calculations. The analysis of several geometrical parameters indicates that all conformers possess bond lengths, angles, and dihedrals that agree fairly well with the crystalline structure of alpha-CD. However, only three of them (1-3) resemble the polar character of CDs and show intramolecular hydrogen-bonding patterns that agree with experimental NMR data. Among them, conformer 3 appears to be the most stable species both in the gas phase and in solution; therefore, it is expected to be the most suitable representative structure for alpha-CD conformation. The purpose of selecting such <span class="hlt">a</span> species is to identify an appropriate structure to be employed as <span class="hlt">a</span> starting point for reliable computational studies on complexation phenomena. Our results indicate that the choice of <span class="hlt">a</span> particular alpha-CD conformer should affect the results of ab initio computational studies on the <span class="hlt">inclusion</span> complexation with this <span class="hlt">cyclodextrin</span> since both the direction and the magnitude of the dipole moment depend strongly on the conformation of alpha-CD.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://eric.ed.gov/?q=Allergy&pg=3&id=EJ1090618','ERIC'); return false;" href="https://eric.ed.gov/?q=Allergy&pg=3&id=EJ1090618"><span>Molecular Recognition: Detection of Colorless <span class="hlt">Compounds</span> Based on Color Change</span></a></p> <p><a target="_blank" href="http://www.eric.ed.gov/ERICWebPortal/search/extended.jsp?_pageLabel=advanced">ERIC Educational Resources Information Center</a></p> <p>Khalafi, Lida; Kashani, Samira; Karimi, Javad</p> <p>2016-01-01</p> <p><span class="hlt">A</span> laboratory experiment is described in which students measure the amount of cetirizine in allergy-treatment tablets based on molecular recognition. The basis of recognition is competition of cetirizine with phenolphthalein to form an <span class="hlt">inclusion</span> complex with ß-<span class="hlt">cyclodextrin</span>. Phenolphthalein is pinkish under basic condition, whereas it's complex form…</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20622447','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20622447"><span>Complexation of tocotrienol with gamma-<span class="hlt">cyclodextrin</span> enhances intestinal absorption of tocotrienol in rats.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ikeda, Saiko; Uchida, Tomono; Ichikawa, Tomio; Watanabe, Takashi; Uekaji, Yukiko; Nakata, Daisuke; Terao, Keiji; Yano, Tomohiro</p> <p>2010-01-01</p> <p>To determine the bioavailability of tocotrienol complex with gamma-<span class="hlt">cyclodextrin</span>, the effects of tocotrienol/gamma-<span class="hlt">cyclodextrin</span> complex on tocotrienol concentration in rat plasma and tissues were studied. Rats were administered by oral gavage an emulsion containing tocotrienol, tocotrienol with gamma-<span class="hlt">cyclodextrin</span>, or tocotrienol/gamma-<span class="hlt">cyclodextrin</span> complex. At 3 h after administration, the plasma gamma-tocotrienol concentration of the rats administered tocotrienol/gamma-<span class="hlt">cyclodextrin</span> complex was higher than that of the rats administered tocotrienol and gamma-<span class="hlt">cyclodextrin</span>. In order to determine the effect of complexation on tocotrienol absorption, rats were injected with Triton WR1339, which prevents the catabolism of triacylglycerol-rich lipoprotein by lipoprotein lipase, and then administered by oral gavage an emulsion containing tocotrienol, tocotrienol with gamma-<span class="hlt">cyclodextrin</span>, or tocotrienol/gamma-<span class="hlt">cyclodextrin</span> complex. The plasma gamma-tocotrienol concentration of the Triton-treated rats administered tocotrienol/gamma-<span class="hlt">cyclodextrin</span> complex was higher than that of the other Triton-treated rats. These results suggest that complexation of tocotrienol with gamma-<span class="hlt">cyclodextrin</span> elevates plasma and tissue tocotrienol concentrations by enhancing intestinal absorption.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26794740','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26794740"><span>Clove essential oil-in-<span class="hlt">cyclodextrin</span>-in-liposomes in the aqueous and lyophilized states: From laboratory to large scale using <span class="hlt">a</span> membrane contactor.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sebaaly, Carine; Charcosset, Catherine; Stainmesse, Serge; Fessi, Hatem; Greige-Gerges, Hélène</p> <p>2016-03-15</p> <p>This work is dedicated to prepare liposomal dry powder formulations of <span class="hlt">inclusion</span> complexes of clove essential oil (CEO) and its main component eugenol (Eug). Ethanol injection method and membrane contactor were applied to prepare liposomes at laboratory and large scale, respectively. Various liposomal formulations were tested: (1) free hydroxypropyl-β-<span class="hlt">cyclodextrin</span> loaded liposomes; (2) drug in hydroxypropyl-β-<span class="hlt">cyclodextrin</span> in liposomes (DCL); (3) DCL2 obtained by double loading technique, where the drug is added in the organic phase and the <span class="hlt">inclusion</span> complex in the aqueous phase. Liposomes were characterized for their particle size, polydispersity index, Zeta potential, morphology, encapsulation efficiency of CEO components and Eug loading rate. Reproducible results were obtained with both injection devices. Compared to Eug-loaded liposomes, DCL and DCL2 improved the loading rate of Eug and possessed smaller vesicles size. The DPPH(•) scavenging activity of Eug and CEO was maintained upon incorporation of Eug and CEO into DCL and DCL2. Contrary to DCL2, DCL formulations were stable after 1 month of storage at 4°C and upon reconstitution of the dried lyophilized cakes. Hence, DCL in aqueous and lyophilized forms, are considered as <span class="hlt">a</span> promising carrier system to preserve volatile and hydrophobic drugs enlarging their application in cosmetic, pharmaceutical and food industries. Copyright © 2015 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2018MApFl...6a3001H','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2018MApFl...6a3001H"><span><span class="hlt">Inclusion</span> of fluorophores in <span class="hlt">cyclodextrins</span>: <span class="hlt">a</span> closer look at the fluorometric determination of association constants by linear and nonlinear fitting procedures</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Hutterer, Rudi</p> <p>2018-01-01</p> <p>The author discusses methods for the fluorometric determination of affinity constants by linear and nonlinear fitting methods. This is outlined in particular for the interaction between <span class="hlt">cyclodextrins</span> and several anesthetic drugs including benzocaine. Special emphasis is given to the limitations of certain fits, and the impact of such studies on enzyme-substrate interactions are demonstrated. Both the experimental part and methods of analysis are well suited for students in an advanced lab.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/21469949','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/21469949"><span>In vitro and in vivo studies on the complexes of glipizide with water-soluble β-<span class="hlt">cyclodextrin</span>-epichlorohydrin polymers.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Nie, Shufang; Zhang, Shu; Pan, Weisan; Liu, Yanli</p> <p>2011-05-01</p> <p>The purpose of this study was to evaluate the potential of <span class="hlt">a</span> newly modified <span class="hlt">cyclodextrin</span> derivative, water-soluble β-<span class="hlt">cyclodextrin</span>-epichlorohydrin polymer (β-CDP), as an effective drug carrier to enhance the dissolution rate and oral bioavailability of glipizide as <span class="hlt">a</span> poorly water-soluble model drug. <span class="hlt">Inclusion</span> complexes of glipizide with β-CDP were prepared by the co-evaporation method and characterized by phase solubility, dissolution, and differential scanning calorimetry. The solubility curve was classified as type <span class="hlt">A</span>(L), which indicated the formation of 1:1 complex between glipizide and β-CDP. β-CDP had better properties of increasing the aqueous solubility of glipizide compared with HP-β-CD. The dissolution rate of drug from the β-CDP complexes was significantly greater than that of the corresponding physical mixtures indicating that the formation of amorphous complex increased the solubility of glipizide. Moreover, the increment in drug dissolution rate from the glipizide/β-CDP systems was higher than that from the corresponding ones with HP-β-CD, which indicated that β-CDP could provide greater capability of solubilization for poorly soluble drugs. Furthermore, in vivo study revealed that the bioavailability of glipizide was significantly improved by glipizide /β-CDP <span class="hlt">inclusion</span> complex after oral administration to beagle dogs.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20014042','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20014042"><span>Prolonged absorption of antimony(V) by the oral route from non-<span class="hlt">inclusion</span> meglumine antimoniate-beta-<span class="hlt">cyclodextrin</span> conjugates.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ribeiro, Raul R; Ferreira, Weverson A; Martins, Patricia S; Neto, Rubens L M; Rocha, Olguita G F; Le Moyec, Laurence; Demicheli, Cynthia; Frézard, Frédéric</p> <p>2010-03-01</p> <p>The orally active composition comprising meglumine antimoniate (MA) and beta-<span class="hlt">cyclodextrin</span> (beta-CD) differs markedly from conventional drug-CD complexes, since it combines <span class="hlt">a</span> water-soluble drug and <span class="hlt">a</span> hydrophilic CD. In order to obtain insights into the mechanism(s) responsible for the improved oral delivery of the drug, physicochemical and pharmacokinetic studies were carried out. The composition investigated here was prepared at <span class="hlt">a</span> 7:1 antimony(Sb)/beta-CD molar ratio, <span class="hlt">a</span> condition that improves its solubility in water and allows the oral administration of <span class="hlt">a</span> high dose of Sb in large animals. It was characterized by circular dichroism, (1)H-NMR, ESI-MS and photon correlation spectroscopy. Pharmacokinetic data were obtained in Beagle dogs after oral administration of the composition at 100 mg Sb/kg. (1)H-NMR and ESI-MS data supported the formation of non-<span class="hlt">inclusion</span> complexes between MA and beta-CD. Sub-micron assemblies were also evidenced that slowly dissociate and presumably release the MA drug, upon reconstitution of the composition in water. Pharmacokinetic studies of MA and MA/beta-CD in dogs showed <span class="hlt">a</span> prolongation of the serum mean residence time of Sb from 4.1 to 6.8 h, upon complexation of MA with beta-CD. Evidence was also obtained that Sb remains essentially under the form of pentavalent Sb-meglumine complex, following gastro-intestinal absorption from the MA/beta-CD composition. In conclusion, the present data support the model that the sustained drug release property of 7:1 MA/beta-CD composition resulted in the prolongation of MA absorption by the oral route and, consequently, in the increase of the drug mean residence time in serum. Copyright (c) 2009 John Wiley & Sons, Ltd.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2008bfc..conf..123A','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2008bfc..conf..123A"><span>Production of <span class="hlt">Cyclodextrins</span> by CGTase from Bacillus clausii Using Different Starches as Substrates</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Alves-Prado, H. F.; Carneiro, A. A. J.; Pavezzi, F. C.; Gomes, E.; Boscolo, M.; Franco, C. M. L.; da Silva, R.</p> <p></p> <p><span class="hlt">Cyclodextrins</span> (CDs) are cyclic oligasaccharides composed by d-glucose monomers joined by α-1,4-d glicosidic linkages. The main types of CDs are α-, β- and γ-CDs consisting of cycles of six, seven, and eight glucose monomers, respectively. Their ability to form <span class="hlt">inclusion</span> complexes is the most important characteristic, allowing their wide industrial application. The physical property of the CD-complexed <span class="hlt">compound</span> can be altered to improve stability, volatility, solubility, or bio-availability. The cyclomaltodextrin glucanotransferase (CGTase, EC 2.4.1.19) is an enzyme capable of converting starch into CD molecules. In this work, the CGTase produced by Bacillus clausii strain E16 was used to produce CD from maltodextrin and different starches (commercial soluble starch, corn, cassava, sweet potato, and waxy corn starches) as substrates. It was observed that the substrate sources influence the kind of CD obtained and that this CGTase displays <span class="hlt">a</span> β-CGTase action, presenting <span class="hlt">a</span> better conversion of soluble starch at 1.0%, of which 80% was converted in CDs. The ratio of total CD produced was 0:0.89:0.11 for α/β/γ. It was also observed that root and tuber starches were more accessible to CGTase action than seed starch under the studied conditions.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25549553','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25549553"><span>Photodynamic effects induced by meso-tris(pentafluorophenyl)corrole and its <span class="hlt">cyclodextrin</span> conjugates on cytoskeletal components of HeLa cells.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Barata, Joana F B; Zamarrón, Alicia; Neves, M Graça P M S; Faustino, M Amparo F; Tomé, Augusto C; Cavaleiro, José A S; Röder, Beate; Juarranz, Ángeles; Sanz-Rodríguez, Francisco</p> <p>2015-03-06</p> <p>The aim of this work was to synthesize new corrole β-<span class="hlt">cyclodextrin</span> conjugates βCD1 (with one β-<span class="hlt">cyclodextrin</span> moiety) and βCD2 (with two β-<span class="hlt">cyclodextrin</span> moieties) from 5,10,15-tris(pentafluorophenyl)corrole (TPFC) and to test in vitro the efficacy of these <span class="hlt">compounds</span> towards tumoral HeLa cells. No dark cytotoxicity was observed for TPFC and βCD1 at the concentration used for PDT cell treatment, even during long incubation periods (24 h). Fluorescence microscopy showed that TPFC and βCD1 accumulate in HeLa cells at lysosomes and in the Golgi apparatus, respectively. The cell survival after the PDT treatment with visible light was dependent on light exposure level and <span class="hlt">compound</span> concentration. βCD1 was able to penetrate efficiently in the cytoplasm of the HeLa cells. In particular, we have analyzed the photodynamic effect of the corrole derivatives on the microtubules of HeLa cells and the morphological alterations on the mitotic spindle. TPFC and βCD1 caused photocytotoxicity in tumoral HeLa cells and induced <span class="hlt">a</span> rapid metaphase blockage of cells that also showed clearly altered configurations of the mitotic spindle. The results showed that TPFC has the highest photosensitizing efficiency on tumoral cells. Copyright © 2014 Elsevier Masson SAS. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19048792','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19048792"><span>[Characterization of microstructure of ibuprofen-hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> and ibuprofen-beta-<span class="hlt">cyclodextrin</span> by atomic force microscope].</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Wang, Li-juan; Zhu, Zhao-jing; Che, Ke-ke; Ju, Feng-ge</p> <p>2008-09-01</p> <p>The microstructures of ibuprofen-hydroxypropyl-bets-<span class="hlt">cyclodextrin</span> (IBU-HP-beta-CyD) and ibuprofen-beta-<span class="hlt">cyclodextrin</span> (IBU-beta-CyD) were observed by atomic force microscope (AFM). The high resolving capability of AFM has the tungsten filament probe with the spring constant of 0.06 N x m(-1). Samples were observed in <span class="hlt">a</span> small scale scanning area of 10.5 nm x 10.5 nm and 800 x 800 pixels. The original scanning images were gained by tapping mode at room temperature. Their three-dimensional reconstruction of microstructure was performed by G3DR software. The outer diameters of HP-beta-CyD and beta-CyD are 1.53 nm. The benzene diameter of IBU is 0.62 nm, fitting to the inner diameters of HP-beta-CyD and beta-CyD. The benzene and hydrophobic chain of IBU enter into the hole of <span class="hlt">cyclodextrin</span> at 1:1 ratio. The results were evidenced by IR, X-ray diffraction and the phase solubility.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://pubs.er.usgs.gov/publication/70006493','USGSPUBS'); return false;" href="https://pubs.er.usgs.gov/publication/70006493"><span>Liquid chromatography of hydrocarbonaeous quaternary amines on <span class="hlt">cyclodextrin</span> bonded silica</span></a></p> <p><a target="_blank" href="http://pubs.er.usgs.gov/pubs/index.jsp?view=adv">USGS Publications Warehouse</a></p> <p>Abidi, S.L.</p> <p>1986-01-01</p> <p>Mixtures of n-alkylbenzyldimethylammonium chloride (ABDAC) were resolved into homologous components by high-performance liquid chromatography (HPLC) with <span class="hlt">a</span> <span class="hlt">cyclodextrin</span>-bonded silica stationary phase. With <span class="hlt">a</span> few exceptions, results from this study are similar to those obtained from traditional reversed-phase HPLC. It was found that the presence of electrolytes in aqueous mobile phases is not <span class="hlt">a</span> critical factor in determining the success of HPLC separation. Under normal HPLC conditions, <span class="hlt">a</span> mobile phase consisting of either methanol–water (50:50) or acetonitrile–water (30:70) was employed for obtaining adequate resolution of the quaternary ammonium mixtures. Although the percent organic modifier–water profiles were similar to those in previous studies with these <span class="hlt">compounds</span>, resolution (R) and selectivity (α) parameters were found to be quite susceptible to changes in the mobile phase solvent composition. The retention behavior of the cationic analytes in the homologous series is consistent with the hydrophobic-interaction concept proposed for the retention mechanism via dominant <span class="hlt">inclusion</span> complex formation. Several electrolytes were chosen for <span class="hlt">a</span> study of the counter ion effect on the chromatographic characteristics of ABDAC components. Among the electrolytes examined, the perchlorate ion was found most likely to act as an ion-pairing counter ion for ammonium cations in the HPLC system studied. <span class="hlt">A</span> correlation study established linear relationships between the chain length of ABDAC and the logarithmic capacity factor (k2). The analytical utility of the HPLC method was demonstrated by the analysis of various unknown mixtures.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/15986687','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/15986687"><span>Molecular printboards: monolayers of beta-<span class="hlt">cyclodextrins</span> on silicon oxide surfaces.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Onclin, Steffen; Mulder, Alart; Huskens, Jurriaan; Ravoo, Bart Jan; Reinhoudt, David N</p> <p>2004-06-22</p> <p>Monolayers of beta-<span class="hlt">cyclodextrin</span> host molecules have been prepared on SiO2 surfaces. An ordered and stable cyano-terminated monolayer was modified in three consecutive surface reactions. First, the cyanide groups were reduced to their corresponding free amines using Red Al as <span class="hlt">a</span> reducing agent. Second, 1,4-phenylene diisothiocyanate was used to react with the amine monolayer where it acts as <span class="hlt">a</span> linking molecule, exposing isothiocyanates that can be derivatized further. Finally, per-6-amino beta-<span class="hlt">cyclodextrin</span> was reacted with these isothiocyanate functions to yield <span class="hlt">a</span> monolayer exposing beta-<span class="hlt">cyclodextrin</span>. All monolayers were characterized by contact angle measurements, ellipsometric thickness measurements, Brewster angle Fourier transform infrared spectroscopy, X-ray photoelectron spectroscopy, and time-of-flight secondary ion mass spectrometry, which indicate the formation of <span class="hlt">a</span> densely packed <span class="hlt">cyclodextrin</span> surface. It was demonstrated that the beta-<span class="hlt">cyclodextrin</span> monolayer could bind suitable guest molecules in <span class="hlt">a</span> reversible manner. <span class="hlt">A</span> fluorescent molecule (1), equipped with two adamantyl groups for complexation, was adsorbed onto the host monolayer from solution to form <span class="hlt">a</span> monolayer of guest molecules. Subsequently, the guest molecules were desorbed from the surface by competition with increasing beta-<span class="hlt">cyclodextrin</span> concentration in solution. The data were fitted using <span class="hlt">a</span> model. An intrinsic binding constant of 3.3 +/- 1 x 10(5) M(-1) was obtained, which corresponds well to previously obtained results with <span class="hlt">a</span> divalent guest molecule on beta-<span class="hlt">cyclodextrin</span> monolayers on gold. In addition, the number of guest molecules bound to the host surface was determined, and <span class="hlt">a</span> surface coverage of ca. 30% was found.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19799384','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19799384"><span>Effects of addition of alpha-<span class="hlt">cyclodextrin</span> on the sensory quality, volatile <span class="hlt">compounds</span>, and color parameters of fresh pear juice.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>López-Nicolás, José M; Andreu-Sevilla, Antonio J; Carbonell-Barrachina, Angel A; García-Carmona, Francisco</p> <p>2009-10-28</p> <p><span class="hlt">Cyclodextrins</span> (CDs) are widely used as browning inhibitors in different fruit juices. However, pear juice quality is affected by many properties, such as odor and aroma, and to date, no paper has reported the effect of the addition of CDs on the flavor profile of <span class="hlt">a</span> fruit juice. In this study, the aroma profile of pear juice was mainly formed by volatile <span class="hlt">compounds</span> from four chemical families: esters, aldehydes, alcohols, and hydrocarbons. Even though the addition of alpha-CD had <span class="hlt">a</span> significant effect on both the concentration of individual volatile <span class="hlt">compounds</span> and their grouping, only the highest concentration, 90 mM, prevented the oxidation of the volatile precursors present in freshly squeezed juice. Moreover, correlation of these results, concerning the color and aroma of pear juice in the presence of CDs, with the consumer preferences has not been reported. <span class="hlt">A</span> descriptive sensory analysis of pear juices in both the presence and the absence of CDs was carried out, and odor/aroma attributes (fresh, fruity, pear-like, unnatural, etc.), plus global color, odor, aroma, and quality, were quantified using <span class="hlt">a</span> trained panel of judges. The addition of alpha-CD at 90 mM resulted in pear juices with the best color but with low aromatic intensity and low sensory quality. On the other hand, the addition of alpha-CD at 15 mM led to <span class="hlt">a</span> pear juice also with an acceptable color but at the same time with <span class="hlt">a</span> high intensity of fruity and pear-like odors/aromas, making it the best appreciated juice by the panel.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27978804','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27978804"><span><span class="hlt">Cyclodextrins</span> Based Electrochemical Sensors for Biomedical and Pharmaceutical Analysis.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Lenik, Joanna</p> <p>2017-01-01</p> <p>Electrochemical sensors are very convenient devices, as they may be used in <span class="hlt">a</span> lot of fields starting from the food industry to environmental monitoring and medical diagnostics. They offer the values of simple design, reversible and reproducible measurements, as well as ensuring precise and accurate analytical information. Compared with other methods, electrochemical sensors are relatively simple as well as having low costs, which has led to intensive development, especially in the field of medicine and pharmaceuticals within the last decade. Recently, the number of publications covering the determination of aminoacids, dopamine, cholesterol, uric acid, biomarkers, vitamins and other pharmaceutical and biological <span class="hlt">compounds</span> has significantly increased. Many possible types of such sensors and biosensors have been proposed: owing to the kind of the detection-potentiometric voltametric, amperometry, and the materials that can be used for, e.g. designing molecular architecture of the electrode/solution interface, carbon paste, carbon nanotubes, glass carbon, graphite, graphene, PVC, conductive polymers and/or nanoparticles. The active <span class="hlt">compounds</span> which provide the complex formation with analyte (in the case of non-current techniques) or activate biomolecules electrochemically by particle recognition and selective preconcentration of analyte on the electrode surface (in the case of current techniques) are the most recently used <span class="hlt">cyclodextrins</span>. These macrocyclic <span class="hlt">compounds</span> have the ability to interact with <span class="hlt">a</span> large diversity of guest particles to form complexes of the type of guest host, for example, with particles from drugs, biomolecules, through their hydrophilic outer surface and lipophilic inner cavities. <span class="hlt">Cyclodextrins</span> have been the subject of frequent electrochemical studies that focused mostly on both their interactions in <span class="hlt">a</span> solid state and in solution. The process of preparing of CDs modified electrodes would, consequently, open new avenues for new electrochemical</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25172711','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25172711"><span>Effect of <span class="hlt">inclusion</span> of hydroxycinnamic and chlorogenic acids from green coffee bean in β-<span class="hlt">cyclodextrin</span> on their interactions with whey, egg white and soy protein isolates.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Budryn, Grażyna; Pałecz, Bartłomiej; Rachwał-Rosiak, Danuta; Oracz, Joanna; Zaczyńska, Donata; Belica, Sylwia; Navarro-González, Inmaculada; Meseguer, Josefina María Vegara; Pérez-Sánchez, Horacio</p> <p>2015-02-01</p> <p>The aim of the study was to characterise the interactions of hydroxycinnamic and chlorogenic acids (CHAs) from green coffee, with isolates of proteins from egg white (EWP), whey (WPC) and soy (SPI), depending on pH and temperature. The binding degree was determined by liquid chromatography coupled to <span class="hlt">a</span> diode array detector and an ultrahigh resolution hybrid quadruple-time-of-flight mass spectrometer with ESI source (LC-QTOF-MS/MS). As <span class="hlt">a</span> result of binding, the concentration of CHAs in proteins ranged from 9.44-12.2, 11.8-13.1 and 12.1-14.4g/100g for SPI, WPC and EWP, respectively. Thermodynamic parameters of protein-ligand interactions were determined by isothermal titration calorimetry (ITC) and energetics of interactions at the atomic level by molecular modelling. The amount of CHAs released during proteolytic digestion was in the range 0.33-2.67g/100g. <span class="hlt">Inclusion</span> of CHAs with β-<span class="hlt">cyclodextrin</span> strongly limited these interactions to <span class="hlt">a</span> level of 0.03-0.06g/100g. Copyright © 2014 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26344257','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26344257"><span>Microwave-assisted synthesis of <span class="hlt">cyclodextrin</span> polyurethanes.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Biswas, Atanu; Appell, Michael; Liu, Zengshe; Cheng, H N</p> <p>2015-11-20</p> <p><span class="hlt">Cyclodextrin</span> (CD) has often been incorporated into polyurethanes in order to facilitate its use in encapsulation or removal of organic species for various applications. In this work <span class="hlt">a</span> microwave-assisted method has been developed to produce polyurethanes consisting of α-, β-, and γ-CD and three common diisocyanates. As compared to conventional heating, this new synthetic method saves energy, significantly reduces reaction time, and gets similar or improved yield. The reaction products have been fully characterized with (13)C, (1)H, and two-dimensional NMR spectroscopy. With suitable stoichiometry of starting CD and diisocyanate, the resulting CD polyurethane is organic-soluble and water-insoluble and is shown to remove Nile red dye and phenol from water. Possible applications include the removal of undesirable materials from process streams, toxic <span class="hlt">compounds</span> from the environment, and encapsulation of color or fragrance molecules. Published by Elsevier Ltd.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20050726','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20050726"><span>Combining strategies to optimize <span class="hlt">a</span> gel formulation containing miconazole: the influence of modified <span class="hlt">cyclodextrin</span> on textural properties and drug release.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ribeiro, Andreza Maria; Figueiras, Ana; Freire, Cristina; Santos, Delfim; Veiga, Francisco</p> <p>2010-06-01</p> <p>Miconazol, an antimycotic drug, is commonly formulated into semisolid formulations designed to be applied in the oral cavity to treat oral candidiasis. However, given its limited aqueous solubility, permeation through the biological membranes is low and therefore its activity is also limited. <span class="hlt">Cyclodextrins</span> (CDs) have been widely used to increase the solubility and stability of poorly water-soluble drugs. The aim of this study is to formulate <span class="hlt">a</span> gel containing an <span class="hlt">inclusion</span> complex between <span class="hlt">a</span> modified CD, methyl-beta-<span class="hlt">cyclodextrin</span> (MbetaCD), and miconazole (MCZ). The influence of the CD on the textural properties of the prepared gel and the drug release from formulation were evaluated. The gels were prepared using two polymers, Carbopol 71G and Pluronic F127, which were selected taking into account their bioadhesiveness and thermal-sensitive gelling properties, respectively. Texture profile analyses were performed at two different temperatures to ascertain the influence of the temperature on the gel texture properties. The in vitro MCZ release profiles from the prepared gel and the commercial gel formulations were evaluated and compared using modified Franz diffusion cells. The addition of MbetaCD to the gel resulted in <span class="hlt">a</span> decrease of the gel adhesiveness and firmness, and the MCZ release profile through f1 and f2 proved to be similar to the commercial product. <span class="hlt">A</span> gel comprising miconazol in the form of an <span class="hlt">inclusion</span> complex with MbetaCD showed suitable textural properties to be applied to the buccal mucosa. The MbetaCD enhanced the solubility of the MCZ in the gel formulation resulting in adequate in vitro drug release profiles.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/21039545','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/21039545"><span>Pharmaceutical applications of <span class="hlt">cyclodextrins</span>: basic science and product development.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Loftsson, Thorsteinn; Brewster, Marcus E</p> <p>2010-11-01</p> <p>Drug pipelines are becoming increasingly difficult to formulate. This is punctuated by both retrospective and prospective analyses that show that while 40% of currently marketed drugs are poorly soluble based on the definition of the biopharmaceutical classification system (BCS), about 90% of drugs in development can be characterized as poorly soluble. Although <span class="hlt">a</span> number of techniques have been suggested for increasing oral bioavailability and for enabling parenteral formulations, <span class="hlt">cyclodextrins</span> have emerged as <span class="hlt">a</span> productive approach. This short review is intended to provide both some basic science information as well as data on the ability to develop drugs in <span class="hlt">cyclodextrin</span>-containing formulations. There are currently <span class="hlt">a</span> number of marketed products that make use of these functional solubilizing excipients and new product introduction continues to demonstrate their high added value. The ability to predict whether <span class="hlt">cyclodextrins</span> will be of benefit in creating <span class="hlt">a</span> dosage form for <span class="hlt">a</span> particular drug candidate requires <span class="hlt">a</span> good working knowledge of the properties of <span class="hlt">cyclodextrins</span>, their mechanism of solubilization and factors that contribute to, or detract from, the biopharmaceutical characteristics of the formed complexes. We provide basic science information as well as data on the development of drugs in <span class="hlt">cyclodextrin</span>-containing formulations. <span class="hlt">Cyclodextrins</span> have emerged as an important tool in the formulator's armamentarium to improve apparent solubility and dissolution rate for poorly water-soluble drug candidates. The continued interest and productivity of these materials bode well for future application and their currency as excipients in research, development and drug product marketing. © 2010 The Authors. Journal compilation © 2010 Royal Pharmaceutical Society of Great Britain.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_16");'>16</a></li> <li><a href="#" onclick='return showDiv("page_17");'>17</a></li> <li class="active"><span>18</span></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_18 --> <div id="page_19" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_17");'>17</a></li> <li><a href="#" onclick='return showDiv("page_18");'>18</a></li> <li class="active"><span>19</span></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="361"> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3509578','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3509578"><span>Effect of β-<span class="hlt">Cyclodextrin</span> Complexation on Solubility and Enzymatic Conversion of Naringin</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Cui, Li; Zhang, Zhen-Hai; Sun, E; Jia, Xiao-Bin</p> <p>2012-01-01</p> <p>In the present paper, the effect of β-<span class="hlt">cyclodextrin</span> (β-CD) <span class="hlt">inclusion</span> complexation on the solubility and enzymatic hydrolysis of naringin was investigated. The <span class="hlt">inclusion</span> complex of naringin/β-CD at the molar ratio of 1:1 was obtained by the dropping method and was characterized by differential scanning calorimetry. The solubility of naringin complexes in water at 37 ± 0.1 °C was 15 times greater than that of free naringin. Snailase-involved hydrolysis conditions were tested for the bioconversion of naringin into naringenin using the univariate experimental design. Naringin can be transformed into naringenin by snailase-involved hydrolysis. The optimum conditions for enzymatic hydrolysis were determined as follows: pH 5.0, temperature 37 °C, ratio of snailase/substrate 0.8, substrate concentration 20 mg·mL−1, and reaction time 12 h. Under the optimum conditions, the transforming rate of naringenin from naringin for <span class="hlt">inclusion</span> complexes and free naringin was 98.7% and 56.2% respectively, suggesting that β-CD complexation can improve the aqueous solubility and consequently the enzymatic hydrolysis rate of naringin. PMID:23203062</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20851400','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20851400"><span>Sensitizing of pyrene fluorescence by β-<span class="hlt">cyclodextrin</span>-modified TiO2 nanoparticles.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Shown, Indrajit; Ujihara, Masaki; Imae, Toyoko</p> <p>2010-12-15</p> <p>TiO(2) nanoparticles were synthesized by hydrolysis of tetraisopropyl orthotitanate in an aqueous solution of <span class="hlt">cyclodextrin</span>. The β-<span class="hlt">cyclodextrin</span>-modified spherical TiO(2) nanoparticles were water-dispersible and had an average particle diameter of 4.4 ± 1 nm. Pyrene fluorescence was enhanced by increasing the concentration of β-<span class="hlt">cyclodextrin</span>-modified TiO(2) nanoparticle and the sensitization effect was triply stronger than the case of the β-<span class="hlt">cyclodextrin</span> only. The increase in <span class="hlt">a</span> concentration of host (β-<span class="hlt">cyclodextrin</span>) changes its microenvironment for guest (pyrene), that is, the interaction of pyrene with apolar cavity of β-<span class="hlt">cyclodextrin</span> increases, resulting in enhancement of fluorescence. The sensitization behavior of pyrene fluorescence in the presence of TiO(2) nanoparticles occurs from the increase in the extinction coefficient of pyrene, demonstrating the charge transfer between pyrene and metal oxide nanoparticle. Crown Copyright © 2010. Published by Elsevier Inc. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2018JMoSt1160....1S','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2018JMoSt1160....1S"><span>In-vitro dissolution rate and molecular docking studies of cabergoline drug with β-<span class="hlt">cyclodextrin</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Shanmuga priya, Arumugam; Balakrishnan, Suganya bharathi; Veerakanellore, Giri Babu; Stalin, Thambusamy</p> <p>2018-05-01</p> <p>The physicochemical properties and dissolution profile of cabergoline drug (CAB) with β-<span class="hlt">cyclodextrin</span> (β-CD) <span class="hlt">inclusion</span> complex were investigated by the UV spectroscopy. The <span class="hlt">inclusion</span> complex has used to calculate the stability constant and gives the stoichiometry molar ratio is 1:1 between CAB and β-CD. The phase solubility diagram and the aqueous solubility of CAB (60%) was found to be enhanced by β-CD. In addition, the phase solubility profile of CAB with β-CD was classified as AL-type. Binary systems of CAB with β-CD were prepared by Physical mixture, Kneading and solvent evaporation methods. The solid-state properties of the <span class="hlt">inclusion</span> complex were characterized by Fourier transformation-infrared spectroscopy, Differential scanning calorimetry, Powder X-ray diffractometric patterns and Scanning electron microscopic techniques. Theoretically, β-CD and CAB <span class="hlt">inclusion</span> complex obtained by molecular docking studies, it is in good correlation with the results obtained through experimental methods using the Schrödinger software program. In-vitro dissolution profiles of the <span class="hlt">inclusion</span> complexes were carried out and obvious increase in dissolution rate was observed when compared with pure CAB drug and the complexes.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26453474','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26453474"><span><span class="hlt">A</span> novel <span class="hlt">inclusion</span> complex (β-CD/ABP-dHC-cecropin <span class="hlt">A</span>) with antibiotic propertiess for use as an anti-Agrobacterium additive in transgenic poplar rooting medium.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhang, Jiaxin; Li, Jianfeng; Movahedi, Ali; Sang, Ming; Xu, Chen; Xu, Junjie; Wei, Zhiheng; Yin, Tongming; Zhuge, Qiang</p> <p>2015-12-01</p> <p>The increasing resistance of bacteria and fungi to currently available antibiotics is <span class="hlt">a</span> major concern worldwide, leading to enormous effort to develop novel antibiotics with new modes of action.We recently reported that ABP-dHC-cecropin <span class="hlt">A</span> exhibited strong antibacterial and antifungal activity, making it <span class="hlt">a</span> candidate antibiotic substitute. In this study, β-<span class="hlt">cyclodextrin</span> (β-CD) combined with ABP-dHC-cecropin <span class="hlt">A</span> enhanced the physical and chemical properties of ABP-dHC-cecropin <span class="hlt">A</span> but did not significantly decrease its antibacterial activity. Thus, β-CD/ABP-dHC-cecropin <span class="hlt">A</span> should be considered <span class="hlt">a</span> novel antibacterial drug. We used β-CD/ABP-dHC-cecropin <span class="hlt">A</span> as an anti-Agrobacterium <span class="hlt">compound</span> to supplementtransgenic poplar medium. Sideeffects of the <span class="hlt">inclusion</span> complex had little impact on plantgrowth. Thus, β-CD/ABP-dHC-cecropin <span class="hlt">A</span> may be used as traditional antibiotics forpoplar transplantation with greater antibbacterial effects. Copyright © 2015 Elsevier Inc. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28378257','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28378257"><span>New doxorubicin nanocarriers based on <span class="hlt">cyclodextrins</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Viale, Maurizio; Giglio, Valentina; Monticone, Massimiliano; Maric, Irena; Lentini, Giovanni; Rocco, Mattia; Vecchio, Graziella</p> <p>2017-10-01</p> <p>Polymeric nanoparticles and fibrin gels (FBGs) are attractive biomaterials for local delivery of <span class="hlt">a</span> variety of biotherapeutic agents, from drugs to proteins. We combined these different drug delivery approaches by preparing nanoparticle-loaded FBGs characterized by their intrinsic features of drug delivery rate and antiproliferative/apoptotic activities. <span class="hlt">Inclusion</span> complexes of doxorubicin (DOXO) with oligomeric β-<span class="hlt">cyclodextrins</span> (oCyD) functionalized with different functional groups were studied. These nanocarriers were able to interact with FBGs as shown by <span class="hlt">a</span> decreased release rate of DOXO. One of these complexes, oCyDNH 2 /DOXO, demonstrated good antiproliferative and apoptotic activity in vitro, reflecting <span class="hlt">a</span> higher drug uptake by cells. As hypothesized, the nanocarrier/FBG complexes showed <span class="hlt">a</span> lower drug release rate than similar FBGs loaded with the corresponding non-functionalized oCyD/DOXO. Taken together, our results provide experimental evidence that oCyDNH 2 /DOXO complexes may be useful components in enhanced FBGs and further build support for the great promise these complex molecules hold for clinical use in localized anticancer therapy of inoperable or surgically removable tumors of different histological origin.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/22146714','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/22146714"><span>Encapsulation of citral isomers in extracted lemongrass oil with <span class="hlt">cyclodextrins</span>: molecular modeling and physicochemical characterizations.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Rungsardthong Ruktanonchai, Uracha; Srinuanchai, Wanwisa; Saesoo, Somsak; Sramala, Issara; Puttipipatkhachorn, Satit; Soottitantawat, Apinan</p> <p>2011-01-01</p> <p>The complexation between two isomers of citral in lemongrass oil and varying types of <span class="hlt">cyclodextrins</span> (CDs), α-CD, β-CD, and HP-β-CD, were studied by molecular modeling and physicochemical characterization. The results obtained revealed that the most favorable complex formation governing between citrals in lemongrass oil and CDs were found at <span class="hlt">a</span> 1:2 mole ratio for all CDs. Complex formation between E-citral and CD was more favorable than between Z-citral and CD. The thermal stability of the <span class="hlt">inclusion</span> complex was observed compared to the citral in the lemongrass oil. The release time course of citral from the <span class="hlt">inclusion</span> complex was the diffusion control, and it correlated well with Avrami's equation. The release rate constants of the E- and Z-citral <span class="hlt">inclusion</span> complexes at 50 °C, 50% RH were observed at 1.32×10(-2) h(-1) and 1.43×10(-2) h(-1) respectively.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24311389','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24311389"><span>Hydroxypropyl-sulfobutyl-β-<span class="hlt">cyclodextrin</span> improves the oral bioavailability of edaravone by modulating drug efflux pump of enterocytes.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Rong, Wen-Ting; Lu, Ya-Peng; Tao, Qing; Guo, Miao; Lu, Yu; Ren, Yong; Yu, Shu-Qin</p> <p>2014-02-01</p> <p>The objective of the study was to evaluate the effect of hydroxypropyl-sulfobutyl-β-<span class="hlt">cyclodextrin</span> (HP-SBE-βCD) on the bioavailability and intestinal absorption of edaravone, and identify its mechanism of action. We devised HP-SBE-βCD as <span class="hlt">a</span> carrier and modulator of P-glycoprotein (Pgp) efflux pump, and edaravone as <span class="hlt">a</span> model drug, and prepared edaravone/HP-SBE-βCD <span class="hlt">inclusion</span> complex. HP-SBE-βCD improved the water solubility and enhanced the bioavailability of edaravone by 10.3-fold in rats. Then, in situ single-pass intestinal perfusion showed that HP-SBE-βCD had an effect of improving the permeability and inhibiting the efflux of edaravone. Furthermore, the effects of HP-SBE-βCD on Pgp were achieved through interfering with the lipid raft and depleting the cholesterol of enterocytes membrane. From the results, we presented the novel mechanisms. First, edaravone/HP-SBE-βCD had <span class="hlt">a</span> lower release from the <span class="hlt">inclusion</span> <span class="hlt">compound</span> to protect edaravone from the low pH of the stomach. Then, HP-SBE-βCD modulated the membrane microenvironment of intestinal absorption epithelial cells. At last, the result was that HP-SBE-βCD enhanced the absorption of edaravone by interfering with Pgp. In conclusion, HP-SBE-βCD improves the bioavailability of drug not only because of its enhancing water solubility of the drug, but also because it modulates the Pgp-mediated efflux from enterocytes. © 2013 Wiley Periodicals, Inc. and the American Pharmacists Association.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2007JaJAP..46.7273T','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2007JaJAP..46.7273T"><span>Gap Fill Materials Using <span class="hlt">Cyclodextrin</span> Derivatives in ArF Lithography</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Takei, Satoshi; Shinjo, Tetsuya; Sakaida, Yasushi; Hashimoto, Keisuke</p> <p>2007-11-01</p> <p>High planarizing gap fill materials based on β-<span class="hlt">cyclodextrin</span> in ArF photoresist under-layer materials have been developed for fast etching in CF4 gas. Gap fill materials used in the via-first dual damascene process need to have high etch rates to prevent crowning or fencing on top of the trench after etching and <span class="hlt">a</span> small thickness bias between the dense and blanket areas to minimize issues observed during trench lithography by narrowing the process latitude. <span class="hlt">Cyclodextrin</span> is <span class="hlt">a</span> circular oligomer with <span class="hlt">a</span> nanoscale porous structure that has <span class="hlt">a</span> high number of oxygen atoms, as calculated using the Ohnishi parameter, providing high etch rates. Additionally, since gap fill materials using <span class="hlt">cyclodextrin</span> derivatives have low viscosities and molecular weights, they are expected to exhibit excellent flow properties and minimal thermal shrinkage during baking. In this paper, we describe the composition and basic film properties of gap fill materials; planarization in the via-first dual damascene process and etch rates in CF4 gas compared with dextrin with α-glycoside bonds in polysaccharide, poly(2-hydroxypropyl methacrylate) and poly(4-hydroxystyrene). The β-<span class="hlt">cyclodextrin</span> used in this study was obtained by esterifying the hydroxyl groups of dextrin resulting in improved wettability on via substrates and solubility in photoresist solvents such as propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate and ethyl lactate. Gap fill materials using <span class="hlt">cyclodextrin</span> derivatives showed good planarization and via filling performance without observing voids in via holes. In addition to superior via filling performance, the etch rate of gap fill materials using β-<span class="hlt">cyclodextrin</span> derivatives was 2.8-2.9 times higher than that of an ArF photoresist, evaluated under CF4 gas conditions by reactive ion etching. These results were attributed to the combination of both nanoscale porous structures and <span class="hlt">a</span> high density of oxygen atoms in our gap fill materials using <span class="hlt">cyclodextrin</span></p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20665507','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20665507"><span>Structural evaluation of crystalline ternary γ-<span class="hlt">cyclodextrin</span> complex.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Higashi, Kenjirou; Ideura, Saori; Waraya, Haruka; Moribe, Kunikazu; Yamamoto, Keiji</p> <p>2011-01-01</p> <p>The structure of <span class="hlt">a</span> crystalline γ-<span class="hlt">cyclodextrin</span> (γ-CD) ternary complex containing salicylic acid (SA) and flurbiprofen (FBP) prepared by sealed heating was investigated. FBP/γ-CD <span class="hlt">inclusion</span> complex was prepared by coprecipitation; its molar ratio was determined as 1/1. Powder X-ray diffraction measurements showed that the molecular packing of γ-CD changed from hexagonal to monoclinic columnar form by sealed heating of SA with dried FBP/γ-CD <span class="hlt">inclusion</span> complex, indicating ternary complex formation. The stoichiometry of SA/FBP/γ-CD was estimated as 2/1/1. Solid-state transformation of γ-CD molecular packing upon water vapor adsorption and desorption was irreversible for this ternary complex, in contrast to the reversible transition for the FBP/γ-CD <span class="hlt">inclusion</span> complex. The ternary complex contained one FBP molecule in the cavity of γ-CD and two SA molecules in the intermolecular space between neighboring γ-CD column stacks. Infrared and (13) C solid-state NMR spectroscopies revealed that the molecular states of SA and FBP changed upon ternary complex formation. In the complex, dimer FBP molecules were sandwiched between two γ-CD molecules whereas each monomer SA molecule was present in the intermolecular space of γ-CD. Ternary complex formation was also observed for other drug-guest systems using naproxen and ketoprofen. Thus, the complex can be used to formulate variety of drugs. Copyright © 2010 Wiley-Liss, Inc. and the American Pharmacists Association</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19267300','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19267300"><span><span class="hlt">Cyclodextrin</span> modified hydrogels of PVP/PEG for sustained drug release.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Nielsen, Anne Louise; Madsen, Flemming; Larsen, Kim Lambertsen</p> <p>2009-02-01</p> <p>Hydrogels are water swollen networks of polymers and especially hydrogels consisting of poly vinylpyrrolidone/poly ethyleneglycol-dimethacrylate (PVP/PEG-DMA) blends show promising wound care properties. Enhanced functionality of the hydrogels can be achieved by incorporating drugs and other substances that may assist wound healing into the gel matrix. Controlling the release of active <span class="hlt">compounds</span> from the hydrogels may be possible by carefully modifying the polymer matrix. For this purpose, <span class="hlt">cyclodextrins</span> (CD) were grafted to the polymer matrix in 4-5 w/w% in an attempt to retard the release of water-soluble drugs. Ibuprofenate (IBU) was chosen as model drug and loaded in IBU/CD ratios of 0.6, 1.2, and 2.5. Vinyl derivatives of alpha-, beta- and gamma-CD were produced, added to the prepolymer blend and cured by UV-light. During this curing process the CD derivatives were covalently incorporated into the hydrogel matrix. The modified hydrogels were loaded with ibuprofenate by swelling. The release of the model drug from CD modified hydrogels show that especially covalently bonded beta-<span class="hlt">cyclodextrin</span> can change both the release rate and the release profile of ibuprofen.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25557507','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25557507"><span>Encapsulation of carvacrol, <span class="hlt">a</span> monoterpene present in the essential oil of oregano, with β-<span class="hlt">cyclodextrin</span>, improves the pharmacological response on cancer pain experimental protocols.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Guimarães, Adriana Gibara; Oliveira, Marlange Almeida; Alves, Rafael dos Santos; Menezes, Paula dos Passos; Serafini, Mairim Russo; Araújo, Adriano Antunes de Souza; Bezerra, Daniel Pereira; Quintans Júnior, Lucindo José</p> <p>2015-02-05</p> <p>Cancer pain is <span class="hlt">a</span> major public health problem worldwide due to the strong impact on the quality of life of patients and side effects of the existing therapeutic options. Monoterpenes, as carvacrol (CARV), have been extensively studied about their therapeutic properties, especially their importance in the control of painful conditions and inflammation, which can be improved through the use of <span class="hlt">inclusion</span> complexes of β-<span class="hlt">cyclodextrin</span> (β-CD). We evaluated the effect of encapsulation of CARV in β-CD (CARV/β-CD) on the nociception induced by tumor cells (Sarcoma 180) in rodents. <span class="hlt">Inclusion</span> complexes were prepared in two different procedures and characterized through thermal analysis and scanning electron microscopy. CARV/β-CD complex was administered (50 mg/kg, p.o.) in mice with tumor on the hind paw and was able to reduce the hyperalgesia (von Frey) during 24 h, unlike the free CARV (100 mg/kg, p.o.), which promoted effects until 9 h. Administration on alternate days of complex of CARV/β-CD (12.5-50 mg/kg, p.o.) reduced hyperalgesia, as well as spontaneous and palpation-induced nociception. However, pure CARV (50 mg/kg) did not cause significant changes in nociceptive responses. Together, these results produced evidence that the encapsulation of carvacrol in β-<span class="hlt">cyclodextrin</span> can be useful for the development of new options for pain management. Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5238591','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5238591"><span>Stabilization of nanosized titanium dioxide by <span class="hlt">cyclodextrin</span> polymers and its photocatalytic effect on the degradation of wastewater pollutants</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Agócs, Tamás Zoltán; Puskás, István; Varga, Erzsébet; Molnár, Mónika</p> <p>2016-01-01</p> <p>Advanced oxidation processes (AOPs) are considered highly competitive water treatment technologies for the removal of organic pollutants. Among AOP techniques, photocatalysis has recently been the most widely studied. Our aims were to investigate how the dispersion of nanosized titanium dioxide (nanoTiO2) applied in photodegradation-based procedures can be stabilized with <span class="hlt">cyclodextrins</span> in order to obtain <span class="hlt">a</span> new, more efficient photocatalyst for the purification of waters polluted by xenobiotics applying UV irradiation. During our work, on the one hand, we studied the behavior and stability of nanoTiO2 in <span class="hlt">cyclodextrin</span> solutions. On the other hand, we used various monomer and polymer <span class="hlt">cyclodextrin</span> derivatives, and assessed the options for nanoTiO2 stabilization in the presence of various salts and tap water on the basis of turbidity tests. The physical stability of nanoTiO2 dispersions is diminished in the presence of the salts found in tap water (and occurring also in surface waters and ground water) and they are precipitated immediately. This colloidal instability can be improved by <span class="hlt">cyclodextrin</span> derivatives. Based on the results of our studies we have selected carboxymethyl β-<span class="hlt">cyclodextrin</span> polymer (CMBCD-P) for stabilization of nanoTiO2 dispersions. The photocatalytic degradation of methylene blue and ibuprofen as model organic pollutants in various media (distilled water, NaCl solution and tap water) has been studied using nanoTiO2 as catalyst stabilized by CMBCD-P. CMBCD-P itself showed <span class="hlt">a</span> catalytic effect on the UV degradation of methylene blue. In addition to enhancing the colloid stability of nanoTiO2 CMBCD-P showed also synergistic effects in catalyzing the photodecomposition process of the dye. On the other hand, ibuprofen as <span class="hlt">a</span> model pharmaceutical, <span class="hlt">a</span> pollutant of emerging concern (EP), was protected by CMBCD-P against the photocatalytic degradation showing that <span class="hlt">inclusion</span> complex formation can result in opposite effects depending on the structure of the host</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28144360','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28144360"><span>Stabilization of nanosized titanium dioxide by <span class="hlt">cyclodextrin</span> polymers and its photocatalytic effect on the degradation of wastewater pollutants.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Agócs, Tamás Zoltán; Puskás, István; Varga, Erzsébet; Molnár, Mónika; Fenyvesi, Éva</p> <p>2016-01-01</p> <p>Advanced oxidation processes (AOPs) are considered highly competitive water treatment technologies for the removal of organic pollutants. Among AOP techniques, photocatalysis has recently been the most widely studied. Our aims were to investigate how the dispersion of nanosized titanium dioxide (nanoTiO 2 ) applied in photodegradation-based procedures can be stabilized with <span class="hlt">cyclodextrins</span> in order to obtain <span class="hlt">a</span> new, more efficient photocatalyst for the purification of waters polluted by xenobiotics applying UV irradiation. During our work, on the one hand, we studied the behavior and stability of nanoTiO 2 in <span class="hlt">cyclodextrin</span> solutions. On the other hand, we used various monomer and polymer <span class="hlt">cyclodextrin</span> derivatives, and assessed the options for nanoTiO 2 stabilization in the presence of various salts and tap water on the basis of turbidity tests. The physical stability of nanoTiO 2 dispersions is diminished in the presence of the salts found in tap water (and occurring also in surface waters and ground water) and they are precipitated immediately. This colloidal instability can be improved by <span class="hlt">cyclodextrin</span> derivatives. Based on the results of our studies we have selected carboxymethyl β-<span class="hlt">cyclodextrin</span> polymer (CMBCD-P) for stabilization of nanoTiO 2 dispersions. The photocatalytic degradation of methylene blue and ibuprofen as model organic pollutants in various media (distilled water, NaCl solution and tap water) has been studied using nanoTiO 2 as catalyst stabilized by CMBCD-P. CMBCD-P itself showed <span class="hlt">a</span> catalytic effect on the UV degradation of methylene blue. In addition to enhancing the colloid stability of nanoTiO 2 CMBCD-P showed also synergistic effects in catalyzing the photodecomposition process of the dye. On the other hand, ibuprofen as <span class="hlt">a</span> model pharmaceutical, <span class="hlt">a</span> pollutant of emerging concern (EP), was protected by CMBCD-P against the photocatalytic degradation showing that <span class="hlt">inclusion</span> complex formation can result in opposite effects depending on the structure of the</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2014ApSS..305..267W','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2014ApSS..305..267W"><span>Adsorption of environmental pollutants using magnetic hybrid nanoparticles modified with β-<span class="hlt">cyclodextrin</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Wang, Niejun; Zhou, Lilin; Guo, Jun; Ye, Qiquan; Lin, Jin-Ming; Yuan, Jinying</p> <p>2014-06-01</p> <p>Graft through strategy was utilized to coat magnetic Fe3O4 nanoparticles with poly(glycidyl methacrylate) using ordinary radical polymerization and then β-<span class="hlt">cyclodextrin</span> was linked onto the surface of nanoparticles. With these nanoparticles modified with <span class="hlt">cyclodextrin</span> groups, adsorption of two model environmental pollutants, bisphenol <span class="hlt">A</span> and copper ions, was studied. Host-guest interactions between <span class="hlt">cyclodextrin</span> and aromatic molecules had <span class="hlt">a</span> great contribution to the adsorption of bisphenol <span class="hlt">A</span>, while multiple hydroxyls of <span class="hlt">cyclodextrin</span> also helped the adsorption of copper ions. These magnetic nanoparticles could be applied in the elimination, enrichment and detection of some environmental pollutants.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28614348','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28614348"><span>Organic <span class="hlt">compounds</span> in fluid <span class="hlt">inclusions</span> of Archean quartz-Analogues of prebiotic chemistry on early Earth.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Schreiber, Ulrich; Mayer, Christian; Schmitz, Oliver J; Rosendahl, Pia; Bronja, Amela; Greule, Markus; Keppler, Frank; Mulder, Ines; Sattler, Tobias; Schöler, Heinz F</p> <p>2017-01-01</p> <p>The origin of life is still an unsolved mystery in science. Hypothetically, prebiotic chemistry and the formation of protocells may have evolved in the hydrothermal environment of tectonic fault zones in the upper continental crust, an environment where sensitive molecules are protected against degradation induced e.g. by UV radiation. The composition of fluid <span class="hlt">inclusions</span> in minerals such as quartz crystals which have grown in this environment during the Archean period might provide important information about the first organic molecules formed by hydrothermal synthesis. Here we present evidence for organic <span class="hlt">compounds</span> which were preserved in fluid <span class="hlt">inclusions</span> of Archean quartz minerals from Western Australia. We found <span class="hlt">a</span> variety of organic <span class="hlt">compounds</span> such as alkanes, halocarbons, alcohols and aldehydes which unambiguously show that simple and even more complex prebiotic organic molecules have been formed by hydrothermal processes. Stable-isotope analysis confirms that the methane found in the <span class="hlt">inclusions</span> has most likely been formed from abiotic sources by hydrothermal chemistry. Obviously, the liquid phase in the continental Archean crust provided an interesting choice of functional organic molecules. We conclude that organic substances such as these could have made an important contribution to prebiotic chemistry which might eventually have led to the formation of living cells.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27727482','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27727482"><span>Supra-dendron Gelator Based on Azobenzene-<span class="hlt">Cyclodextrin</span> Host-Guest Interactions: Photoswitched Optical and Chiroptical Reversibility.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Xie, Fan; Ouyang, Guanghui; Qin, Long; Liu, Minghua</p> <p>2016-12-12</p> <p><span class="hlt">A</span> novel amphiphilic dendron (AZOC 8 GAc) with three l-glutamic acid units and an azobenzene moiety covalently linked by an alkyl spacer has been designed. The <span class="hlt">compound</span> formed hydrogels with water at very low concentration and self-assembled into chiral-twist structures. The gel showed <span class="hlt">a</span> reversible macroscopic volume phase transition in response to pH variations and photo-irradiation. During the photo-triggered changes, although the gel showed complete reversibility in its optical absorptions, only an incomplete chiroptical property change was achieved. On the other hand, the dendron could form <span class="hlt">a</span> 1:1 <span class="hlt">inclusion</span> complex through <span class="hlt">a</span> host-guest interaction with α-<span class="hlt">cyclodextrin</span> (α-CD), designated as supra-dendron gelator AZOC 8 GAc/α-CD. The supra-dendron showed similar gelation behavior to that of AZOC 8 GAc, but with enhanced photoisomerization-transition efficiency and chiroptical switching capacity, which was completely reversible in terms of both optical and chiroptical performances. The self-assembly of the supra-dendron is <span class="hlt">a</span> hierarchical or multi-supramolecular self-assembling process. This work has clearly illustrated that the hierarchical and multi-supramolecular self-assembling system endows the supramolecular nanostructures or materials with superior reversible optical and chiroptical switching. © 2016 Wiley-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19124130','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19124130"><span>Novel beta-<span class="hlt">cyclodextrin</span> derivative functionalized polymethacrylate-based monolithic columns for enantioselective separation of ibuprofen and naproxen enantiomers in capillary electrochromatography.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tian, Yun; Zhong, Cheng; Fu, Enqin; Zeng, Zhaorui</p> <p>2009-02-06</p> <p><span class="hlt">A</span> novel enantioselective polymethacrylate-based monolithic column for capillary electrochromatography was prepared by ring-opening reaction of epoxy groups from poly(glycidyl methacrylate-co-ethylene dimethacrylate) monolith with <span class="hlt">a</span> novel beta-<span class="hlt">cyclodextrin</span> derivative bearing 4-dimethylamino-1,8-naphthalimide functionalities. Conditions for the ring-opening reaction with respect to different reaction parameters were thoroughly optimized to obtain high electroosmotic flow, separation efficiency and enantioselectivity for the analytes. The nonaqueous mobile phase composition regarding acetonitrile-methanol ratio and the concentration of electrolyte were examined to manipulate the hydrophobic <span class="hlt">inclusion</span> and anion-exchange interaction between the analytes and chiral stationary phase. It was observed that in addition to beta-<span class="hlt">cyclodextrin</span> cavity, the electrostatic interaction exhibited pronounced influence on the enantioseparation of acidic analytes. Acidic enantiomers (ibuprofen and naproxen) could be separated with separation factor (alpha) values up to 1.08 and <span class="hlt">a</span> maximum separation efficiency of 86000 plates/m could be achieved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29230268','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29230268"><span>An Alginate/<span class="hlt">Cyclodextrin</span> Spray Drying Matrix to Improve Shelf Life and Antioxidant Efficiency of <span class="hlt">a</span> Blood Orange By-Product Extract Rich in Polyphenols: MMPs Inhibition and Antiglycation Activity in Dysmetabolic Diseases.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Lauro, Maria Rosaria; Crascì, Lucia; Giannone, Virgilio; Ballistreri, Gabriele; Fabroni, Simona; Sansone, Francesca; Rapisarda, Paolo; Panico, Anna Maria; Puglisi, Giovanni</p> <p>2017-01-01</p> <p>Alginate and β -<span class="hlt">cyclodextrin</span> were used to produce easily dosable and spray-dried microsystems of <span class="hlt">a</span> dried blood orange extract with antidysmetabolic properties, obtained from <span class="hlt">a</span> by-product fluid extract. The spray-dried applied conditions were able to obtain <span class="hlt">a</span> concentrate dried extract without the loss of AOA and with TPC and TMA values of 35-40% higher than that of the starting material. They were also effective in producing microparticles with 80-100% of encapsulation efficiency. The 2% sodium alginate was capable of improving the extract shelf life , while the beta-<span class="hlt">cyclodextrin</span> (1 : 1 molar ratio with dried extract) prolonged the extract antioxidant efficiency by 6 hours. The good inhibition effect of the dried extract on the AGE formation and the MMP-2 and MMP-9 activity is presumably due to <span class="hlt">a</span> synergic effect exerted by both anthocyanin and bioflavonoid extract <span class="hlt">compounds</span> and was improved by the use of alginate and <span class="hlt">cyclodextrin</span>.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5688344','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5688344"><span>An Alginate/<span class="hlt">Cyclodextrin</span> Spray Drying Matrix to Improve Shelf Life and Antioxidant Efficiency of <span class="hlt">a</span> Blood Orange By-Product Extract Rich in Polyphenols: MMPs Inhibition and Antiglycation Activity in Dysmetabolic Diseases</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Giannone, Virgilio; Ballistreri, Gabriele; Fabroni, Simona; Rapisarda, Paolo; Panico, Anna Maria; Puglisi, Giovanni</p> <p>2017-01-01</p> <p>Alginate and β-<span class="hlt">cyclodextrin</span> were used to produce easily dosable and spray-dried microsystems of <span class="hlt">a</span> dried blood orange extract with antidysmetabolic properties, obtained from <span class="hlt">a</span> by-product fluid extract. The spray-dried applied conditions were able to obtain <span class="hlt">a</span> concentrate dried extract without the loss of AOA and with TPC and TMA values of 35–40% higher than that of the starting material. They were also effective in producing microparticles with 80–100% of encapsulation efficiency. The 2% sodium alginate was capable of improving the extract shelf life, while the beta-<span class="hlt">cyclodextrin</span> (1 : 1 molar ratio with dried extract) prolonged the extract antioxidant efficiency by 6 hours. The good inhibition effect of the dried extract on the AGE formation and the MMP-2 and MMP-9 activity is presumably due to <span class="hlt">a</span> synergic effect exerted by both anthocyanin and bioflavonoid extract <span class="hlt">compounds</span> and was improved by the use of alginate and <span class="hlt">cyclodextrin</span>. PMID:29230268</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/10839140','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/10839140"><span>Enantioselective determination by capillary electrophoresis with <span class="hlt">cyclodextrins</span> as chiral selectors.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Fanali, S</p> <p>2000-04-14</p> <p>This review surveys the separation of enantiomers by capillary electrophoresis using <span class="hlt">cyclodextrins</span> as chiral selector. <span class="hlt">Cyclodextrins</span> or their derivatives have been widely employed for the direct chiral resolution of <span class="hlt">a</span> wide number of enantiomers, mainly of pharmaceutical interest, selected examples are reported in the tables. For method optimisation, several parameters influencing the enantioresolution, e.g., <span class="hlt">cyclodextrin</span> type and concentration, buffer pH and composition, presence of organic solvents or complexing additives in the buffer were considered and discussed. Finally, selected applications to real samples such as pharmaceutical formulations, biological and medical samples are also discussed.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_17");'>17</a></li> <li><a href="#" onclick='return showDiv("page_18");'>18</a></li> <li class="active"><span>19</span></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_19 --> <div id="page_20" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_18");'>18</a></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li class="active"><span>20</span></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="381"> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2006JMoSt.794...35S','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2006JMoSt.794...35S"><span><span class="hlt">A</span> study on the spectroscopy and photophysics of 4-hydroxy-3-methoxybenzoic acid in different solvents, pH and β-<span class="hlt">cyclodextrin</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Stalin, T.; Rajendiran, N.</p> <p>2006-08-01</p> <p>Effect of solvents, buffer solutions of different pH and β-<span class="hlt">cyclodextrin</span> (β-CD) on the absorption and fluorescence spectra of 4-hydroxy-3-methoxybenzoic acid (vanillic acid, HMB) have been investigated and compared with 4-hydroxy-3,5-dimethoxybenzoic acid (HDMB). The <span class="hlt">inclusion</span> complex of β-CD with HMB is investigated by UV-vis, fluorimetry, FT-IR, 1H NMR, scanning electron microscope (SEM) and semiempirical methods. The thermodynamic parameters (Δ G, Δ H and Δ S) of <span class="hlt">inclusion</span> process are also determined. Solvent study shows in the S 0 state, HMB is more polar than HDMB, whereas the polarity is same in the S 1 state. pH studies suggest proton transfer reactions follow the same trend in HMB and HDMB molecules. β-CD studies indicates (i) HMB forms 1:1 <span class="hlt">inclusion</span> complex with β-CD and (ii) unusual blue shift of hydroxyl ion (dianion) in the β-CD medium confirms OH group present in the interior part of the β-CD cavity and COOH group present in the upper part of the β-CD cavity. <span class="hlt">A</span> mechanism is proposed to explain the <span class="hlt">inclusion</span> process.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2015CryRp..60.1006Y','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2015CryRp..60.1006Y"><span>Synthesis and crystal structures of <span class="hlt">inclusion</span> <span class="hlt">compounds</span> of 2,2'-dithiosalicylic acid and triethylamine/tripropylamine</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Yang, Y. X.; Li, H. Y.; Wu, J. F.</p> <p>2015-12-01</p> <p>Herein we reported two new <span class="hlt">inclusion</span> <span class="hlt">compounds</span> of 2,2'-dithiosalicylic acid (C14H10O4S2, DTSA) and triethylamine and tripropylamine, [C14H8O4S 2 2- · [N+(C2H5)3]2 · H2O] (1) and [C14H10O4S2 · C14H8O4S 2 2- · [N+(C3H7)3]2] (2). <span class="hlt">Compound</span> 1: triclinic P overline 1, <span class="hlt">a</span> = 8.2159(2), b = 12.5724(3), c = 14.9203(3) Å, α = 97.0390(10), β = 101.4310(10)°, γ = 101.3370(10)°, V = 1460.06(6) Å3, Z = 2, R 1 = 0.0526, wR 2 = 0.1495; <span class="hlt">Compound</span> 2: monoclinic P21/ c, <span class="hlt">a</span> = 20.5178(13), b = 15.3623(8), c = 15.5529(9) Å, β = 102.036(3)°, V = 4794.5(5) Å3, Z = 4, R 1 = 0.0533, wR 2 = 0.1252. In these two crystal structures, DTSA utilizes conventional O-H···O hydrogen bonds to link to generate varied host lattices, in which the central N atoms of the guest amine molecules accept the protons of DTSA to form the corresponding cations to act as the couterions to develop the stable crystal structures. Noticeably, except Van der Waals forces usually existing between the host and guest molecules, the central N atoms of the guests of the two <span class="hlt">compounds</span> can construct strong N-H…O hydrogen bonds with the related host molecules, which further enforce the host-guest interactions to help form the final <span class="hlt">inclusion</span> <span class="hlt">compounds</span>.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/18969046','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/18969046"><span>Spectrofluorimetric study of the beta-<span class="hlt">cyclodextrin</span>-ibuprofen complex and determination of ibuprofen in pharmaceutical preparations and serum.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Hergert, L A; Escandar, G M</p> <p>2003-06-13</p> <p>The <span class="hlt">inclusion</span> complexation of ibuprofen in beta-<span class="hlt">cyclodextrin</span> (beta-CD) has been examined by means of spectrofluorimetry at both acid and alkaline pH. The results suggest that stable 1:1 complexes are formed in both media. The analysis of the pK(<span class="hlt">a</span>) values for ibuprofen in both the absence and presence of beta-CD (4.12 and 4.66, respectively) suggests that in the <span class="hlt">inclusion</span> complex the carboxylic group is located outside the <span class="hlt">cyclodextrin</span> (CD) but interacting with it. Further structural characterization of the complex was carried out by means of am1 semiempiral calculations. Based on the obtained results, <span class="hlt">a</span> spectrofluorimetric method for the determination of ibuprofen in the presence of beta-CD at 10 degrees C was developed in the range of 4.7-58 mug ml(-1). Better limits of detection (1.6 mug ml(-1)) and quantification (4.7 mug ml(-1)) were obtained in this latter case with respect to those obtained in the absence of beta-CD. The method was satisfactorily applied to the quantification of ibuprofen in pharmaceutical preparations. <span class="hlt">A</span> novel spectrofluorimetric determination of ibuprofen in the presence of beta-CD was also developed for serum samples at concentration levels between 5 and 70 mug ml(-1). It uses second-order fluorescence excitation-emission matrices coupled to an algorithm based on self-weighted alternating trilinear decomposition (SWATLD), and avoids resorting to separative instrumental analyses.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28956453','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28956453"><span>Viscosity reduction of isotonic solutions of the photosensitizer TPCS2<span class="hlt">a</span> by <span class="hlt">cyclodextrin</span> complexation.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tovsen, Marianne Lilletvedt; Tho, Ingunn; Tønnesen, Hanne Hjorth</p> <p>2018-02-01</p> <p>Meso-tetraphenyl chlorin disulphonate (TPCS 2<span class="hlt">a</span> ) is <span class="hlt">a</span> photosensitizer (PS) particularly developed and patented for use in the technology of photochemical internalization (PCI) against cancer. TPCS 2<span class="hlt">a</span> is known to aggregate in aqueous media even at low concentrations (≥0.1 µM) and to form <span class="hlt">a</span> high-viscosity network at clinically relevant concentrations (mM). The aim of this work was to evaluate the effect of two hydroxypropylated <span class="hlt">cyclodextrin</span> derivatives of beta and gamma type, respectively i.e. HPβCD and HPγCD, on the aggregation and solubilization of TPCS 2<span class="hlt">a</span> in isotonic solutions. Samples containing micromolar concentrations of TPCS 2<span class="hlt">a</span> were studied spectrophotometrically, while samples containing <span class="hlt">a</span> clinical relevant concentration (10 mM = 9 mg/ml) of TPCS 2<span class="hlt">a</span> were evaluated by dynamic viscosity measurements. HPβCD was determined to be <span class="hlt">a</span> more suitable solubilizer of TPCS 2<span class="hlt">a</span> than HPγCD in aqueous media both in the absence and presence of salt. The complexation stoichiometry between TPCS 2<span class="hlt">a</span> /HPβCD at micromolar to millimolar concentrations of TPCS 2<span class="hlt">a</span> was determined to be 1:3 and 1:2 in the absence and presence of isotonic NaCl, respectively. The network of TPCS 2<span class="hlt">a</span> (10 mM) was broken down in the presence of 3% w/v (= 20 mM) HPβCD, i.e. <span class="hlt">a</span> 1:2 molar ratio between TPCS 2<span class="hlt">a</span> and the <span class="hlt">cyclodextrin</span>. Formation of the <span class="hlt">inclusion</span> complex resulted in low viscosity samples both in water and in the presence of isotonic NaCl or phosphate buffered saline (PBS) at 25 °C and 37 °C.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3933798','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3933798"><span>Aripiprazole-<span class="hlt">Cyclodextrin</span> Binary Systems for Dissolution Enhancement: Effect of Preparation Technique, <span class="hlt">Cyclodextrin</span> Type and Molar Ratio</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>M. Badr-Eldin, Shaimaa; A. Ahmed, Tarek; R Ismail, Hatem</p> <p>2013-01-01</p> <p>Objective(s): The aim of this work was to investigate the effect of the natural and the chemically modified form of <span class="hlt">cyclodextrins</span> namely; β-<span class="hlt">cyclodextrin</span> (β-CD) and hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HP-β-CD) respectively on the solubility and dissolution rate of aripiprazole; an antipsychotic medication showing poor aqueous solubility. Materials and Methods: Phase solubility of aripiprazole with the studied CDs and the complexation efficiency values (CE) which reflect the solubilizing power of the CDs towards the drug was performed. Solid binary systems of aripiprazole with CDs were prepared by kneading, microwave irradiation and freeze-drying techniques at 1:1 and 1:2 (drug to CD) molar ratios. Drug-CD physical mixtures were also prepared in the same molar ratios for comparison. The dissolution of aripiprazole-binary systems was carried out to select the most appropriate CD type, molar ratio and preparation technique. Results: Phase solubility study indicated formation of higher order complexes and the complexation efficiency values was higher for HP-β-CD compared to β-CD. Drug dissolution study revealed that aripiprazole dissolution was increased upon increasing the CD molar ratio and, the freeze-drying technique was superior to the other studied methods especially when combined with the HP-β-CD. The <span class="hlt">cyclodextrin</span> type, preparation technique and molar ratio exhibited statistically significant effect on the drug dissolution at P≤ 0.05. Conclusion: The freeze-dried system prepared at molar ratio 1:2 (drug: CD) can be considered as efficient tool for enhancing aripiprazole dissolution with the possibility of improving its bioavailability. PMID:24570827</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/1996SPIE.2625..333R','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/1996SPIE.2625..333R"><span>Peripheral substitution of pheophorbides and bacteriopheophorbides to promote <span class="hlt">inclusion</span> into inert carrier systems for PDT</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Roehrs, Susanne; Ruebner-Heuermann, Anja; Hartwich, G.; Scheer, H.; Moser, Joerg G.</p> <p>1996-01-01</p> <p>Pheophorbide <span class="hlt">a</span> ethyl ester, pyropheophorbide <span class="hlt">a</span> ethyl ester, and bacteriopheophorbide ethyl ester were substituted in 31-position with tert.butyl phenoxy or tert.butyl benzoic acid ester groups resp. in order to enhance affinity to (beta) -<span class="hlt">cyclodextrin</span> dimers which form <span class="hlt">inclusion</span> complexes with these photosensitizing drugs. This is <span class="hlt">a</span> first step to construct inert transport complexes in order to photosensitize specifically cancer cells.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25158050','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25158050"><span>Computational investigation of enthalpy-entropy compensation in complexation of glycoconjugated bile salts with β-<span class="hlt">cyclodextrin</span> and analogs.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tidemand, Kasper D; Schönbeck, Christian; Holm, René; Westh, Peter; Peters, Günther H</p> <p>2014-09-18</p> <p>The <span class="hlt">inclusion</span> complexes of glycoconjugated bile salts with β-<span class="hlt">cyclodextrin</span> (β-CD) and 2-hydroxypropyl-β-<span class="hlt">cyclodextrins</span> (HP-β-CD) in aqueous solution were investigated by molecular dynamics simulations to provide <span class="hlt">a</span> molecular explanation of the experimentally observed destabilizing effect of the HP substituents. Good agreement with experimental data was found with respect to penetration depths of CDs. An increased degree of HP substitution (DS) resulted in an increased probability of blocking the cavity opening, thereby hindering the bile salt from entering CD. Further, the residence time of water molecules in the cavity increased with the DS. Release of water from the cavity resulted in <span class="hlt">a</span> positive enthalpy change, which correlates qualitatively with the experimentally determined increase in complexation enthalpy and contributes to the enthalpy-entropy compensation. The positive change in complexation entropy with DS was not able to compensate for this unfavorable change in enthalpy induced by the HP substituents, resulting in <span class="hlt">a</span> destabilizing effect. This was found to originate from fixation of the HP substituents and decreased free rotation of the bile salts within the CD cavities.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27132832','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27132832"><span>Increasing solubility of red bell pepper carotenoids by complexation with 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>de Lima Petito, Nicolly; da Silva Dias, Daiana; Costa, Valéria Gonçalves; Falcão, Deborah Quintanilha; de Lima Araujo, Kátia Gome</p> <p>2016-10-01</p> <p>Red bell pepper carotenoids were complexed with 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (2-HPβCD) in different mass ratios (1:4, 1:6, 1:8 and 1:10) through ultrasonic homogenization in order to increase carotenoid solubility and their use as natural pigment in food. <span class="hlt">Inclusion</span> complexes, red bell pepper extract and physical mixtures were analyzed by DSC, FT-IR, (1)H NMR and DLS. Solubility assay was performed to identify the effect of complexation on the solubility of carotenoids. From characterization assays, results showed that <span class="hlt">inclusion</span> process occurred for all tested ratios. Results for water solubility assays demonstrated clear differences between solubility index of <span class="hlt">inclusion</span> complexes (8.06±2.59-16.55±4.40mg/mL) and physical mixtures (3.53±1.44-7.3±1.88mg/mL), while carotenoid extract was no water soluble, as expected. These results indicated that molecular <span class="hlt">inclusion</span> of carotenoids in 2-HPβCD was efficient to enhance their solubility in water, enabling application of red bell pepper carotenoid as natural pigment and/or bioactive substances in food. Copyright © 2016 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25059157','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25059157"><span>Second-order data obtained by beta-<span class="hlt">cyclodextrin</span> complexes: <span class="hlt">a</span> novel approach for multicomponent analysis with three-way multivariate calibration methods.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Khani, Rouhollah; Ghasemi, Jahan B; Shemirani, Farzaneh</p> <p>2014-10-01</p> <p>This research reports the first application of β-<span class="hlt">cyclodextrin</span> (β-CD) complexes as <span class="hlt">a</span> new method for generation of three way data, combined with second-order calibration methods for quantification of <span class="hlt">a</span> binary mixture of caffeic (CA) and vanillic (VA) acids, as model <span class="hlt">compounds</span> in fruit juices samples. At first, the basic experimental parameters affecting the formation of <span class="hlt">inclusion</span> complexes between target analytes and β-CD were investigated and optimized. Then under the optimum conditions, parallel factor analysis (PARAFAC) and bilinear least squares/residual bilinearization (BLLS/RBL) were applied for deconvolution of trilinear data to get spectral and concentration profiles of CA and VA as <span class="hlt">a</span> function of β-CD concentrations. Due to severe concentration profile overlapping between CA and VA in β-CD concentration dimension, PARAFAC could not be successfully applied to the studied samples. So, BLLS/RBL performed better than PARAFAC. The resolution of the model <span class="hlt">compounds</span> was possible due to differences in the spectral absorbance changes of the β-CD complexes signals of the investigated analytes, opening <span class="hlt">a</span> new approach for second-order data generation. The proposed method was validated by comparison with <span class="hlt">a</span> reference method based on high-performance liquid chromatography photodiode array detection (HPLC-PDA), and no significant differences were found between the reference values and the ones obtained with the proposed method. Such <span class="hlt">a</span> chemometrics-based protocol may be <span class="hlt">a</span> very promising tool for more analytical applications in real samples monitoring, due to its advantages of simplicity, rapidity, accuracy, sufficient spectral resolution and concentration prediction even in the presence of unknown interferents. Copyright © 2014 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3161792','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3161792"><span>Tailored ß-<span class="hlt">Cyclodextrin</span> Blocks the Translocation Pores of Binary Exotoxins from C. Botulinum and C. Perfringens and Protects Cells from Intoxication</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Nestorovich, Ekaterina M.; Karginov, Vladimir A.; Popoff, Michel R.; Bezrukov, Sergey M.; Barth, Holger</p> <p>2011-01-01</p> <p>Background Clostridium botulinum C2 toxin and Clostridium perfringens iota toxin are binary exotoxins, which ADP-ribosylate actin in the cytosol of mammalian cells and thereby destroy the cytoskeleton. C2 and iota toxin consists of two individual proteins, an enzymatic active (<span class="hlt">A</span>-) component and <span class="hlt">a</span> separate receptor binding and translocation (B-) component. The latter forms <span class="hlt">a</span> complex with the <span class="hlt">A</span>-component on the surface of target cells and after receptor-mediated endocytosis, it mediates the translocation of the <span class="hlt">A</span>-component from acidified endosomal vesicles into the cytosol. To this end, the B-components form heptameric pores in endosomal membranes, which serve as translocation channels for the <span class="hlt">A</span>-components. Methodology/Principal Findings Here we demonstrate that <span class="hlt">a</span> 7-fold symmetrical positively charged ß-<span class="hlt">cyclodextrin</span> derivative, per-6-S-(3-aminomethyl)benzylthio-ß-<span class="hlt">cyclodextrin</span>, protects cultured cells from intoxication with C2 and iota toxins in <span class="hlt">a</span> concentration-dependent manner starting at low micromolar concentrations. We discovered that the <span class="hlt">compound</span> inhibited the pH-dependent membrane translocation of the <span class="hlt">A</span>-components of both toxins in intact cells. Consistently, the <span class="hlt">compound</span> strongly blocked transmembrane channels formed by the B-components of C2 and iota toxin in planar lipid bilayers in vitro. With C2 toxin, we consecutively ruled out all other possible inhibitory mechanisms showing that the <span class="hlt">compound</span> did not interfere with the binding of the toxin to the cells or with the enzyme activity of the <span class="hlt">A</span>-component. Conclusions/Significance The described ß-<span class="hlt">cyclodextrin</span> derivative was previously identified as one of the most potent inhibitors of the binary lethal toxin of Bacillus anthracis both in vitro and in vivo, implying that it might represent <span class="hlt">a</span> broad-spectrum inhibitor of binary pore-forming exotoxins from pathogenic bacteria. PMID:21887348</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2018FrCh....6...84D','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2018FrCh....6...84D"><span>Supramolecular Organocatalysis in Water Mediated by Macrocyclic <span class="hlt">Compounds</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>De Rosa, Margherita; La Manna, Pellegrino; Talotta, Carmen; Soriente, Annunziata; Gaeta, Carmine; Neri, Placido</p> <p>2018-04-01</p> <p>In the last decades many efforts have been devoted to design supramolecular organocatalysts able to work in water as the reaction medium. The use of water as solvent provides promising benefits with respect to environmental impact. In this context, macrocyclic <span class="hlt">compounds</span> played <span class="hlt">a</span> role of primary importance thanks to their ease of synthesis and their molecular recognition abilities toward the reactants. The aim of this review is to give an overview of the recent advances in the field of supramolecular organocatalysis in water, focusing the attention on calixarene and <span class="hlt">cyclodextrins</span> derivatives. Calixarenes and <span class="hlt">cyclodextrins</span>, thanks to their hydrophobic cavities, are able to host selectively the substrates isolating they from the reaction environment. In addition, the synthetic versatilities of these macrocycles permits to introduce useful functional groups in close proximity of the hydrophobic binding sites. Regarding the <span class="hlt">cyclodextrins</span> (CDs), we have here reviewed the their most recent uses as organocatalysts for the synthesis of heterocyclic <span class="hlt">compounds</span>, in multi-component reactions and in carbon-carbon bond forming reactions. Examples have been reported in which CD catalysts are able to drive the regiochemistry of common organic reactions. In addition, <span class="hlt">cyclodextrins</span> bearing catalytically active chiral groups, have shown excellent enantioselectivity in the catalysis of organic reactions. Recently reported results have shown that calixarene derivatives are able to accelerate organic reaction under "on-water" conditions with <span class="hlt">a</span> significant selectivity toward the reactants. Under "on-water conditions" the hydrophobic effect, induced by insoluble calixarene derivatives, forces the reactants and the catalyst to aggregate and thus accelerating the reaction between them thanks to an amplification of weak secondary interactions. Regarding the use of water-soluble calixarene organocatalysts, we have here reviewed their role in the acceleration of common organic reactions.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2008AIPC.1042...38G','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2008AIPC.1042...38G"><span><span class="hlt">Inclusion</span> Complexes Behavior at the Air-Water Interface. Molecular Dynamic Simulation Study.</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Gargallo, L.; Vargas, D.; Sandoval, C.; Saavedra, M.; Becerra, N.; Leiva, A.; Radić, D.</p> <p>2008-08-01</p> <p>The interfacial properties of the <span class="hlt">inclusion</span> complexes (ICs), obtained from the threading of α-<span class="hlt">cyclodextrin</span> (α-CD) onto poly(ethylene-oxide)(PEO), poly(ɛ-caprolactone)(PEC) and poly(tetrahydrofuran)(PTHF) and their precursor homopolymers (PHPoly), were studied at the air-water interface. The free surface energy was determined by wettability measurements. The experimental behavior of these systems was described by an atomistic molecular dynamics simulation (MDS).</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23235466','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23235466"><span>β-<span class="hlt">Cyclodextrin</span>'s orientation onto TiO2 and its paradoxical role in guest's photodegradation.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhang, Xu; Yang, Zixin; Li, Xuankun; Deng, Nansheng; Qian, Shahua</p> <p>2013-01-28</p> <p>This work revealed that β-<span class="hlt">cyclodextrin</span> was attached onto the surface of TiO(2) predominately by its secondary ring side, which caused paradoxical functions of β-<span class="hlt">cyclodextrin</span> in the photodegradation of the four bisphenols. The equilibrium between the guest adsorbed through β-<span class="hlt">cyclodextrin</span> onto TiO(2) and the one locked in β-CD in water could also change the role of β-<span class="hlt">cyclodextrin</span> in the degradation of <span class="hlt">a</span> certain guest.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/11952479','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/11952479"><span><span class="hlt">Cyclodextrins</span> in eye drop formulations: enhanced topical delivery of corticosteroids to the eye.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Loftsson, Thorsteinn; Stefánsson, Einar</p> <p>2002-04-01</p> <p><span class="hlt">Cyclodextrins</span> are cylindrical oligosaccharides with <span class="hlt">a</span> lipophilic central cavity and hydrophilic outer surface. They can form water-soluble complexes with lipophilic drugs, which 'hide' in the cavity. <span class="hlt">Cyclodextrins</span> can be used to form aqueous eye drop solutions with lipophilic drugs, such as steroids and some carbonic anhydrase inhibitors. The <span class="hlt">cyclodextrins</span> increase the water solubility of the drug, enhance drug absorption into the eye, improve aqueous stability and reduce local irritation. <span class="hlt">Cyclodextrins</span> are useful excipients in eye drop formulations of various drugs, including steroids of any kind, carbonic anhydrase inhibitors, pilocarpine, cyclosporins, etc. Their use in ophthalmology has already begun and is likely to expand the selection of drugs available as eye drops. In this paper we review the properties of <span class="hlt">cyclodextrins</span> and their application in eye drop formulations, of which their use in the formulation of dexamethasone eye drops is an example. <span class="hlt">Cyclodextrins</span> have been used to formulate eye drops containing corticosteroids, such as dexamethasone, with levels of concentration and ocular absorption which, according to human and animal studies, are many times those seen with presently available formulations. <span class="hlt">Cyclodextrin</span>-based dexamethasone eye drops are well tolerated in the eye and seem to provide <span class="hlt">a</span> higher degree of bioavailability and clinical efficiency than the steroid eye drop formulations presently available. Such formulations offer the possibility of once per day application of corticosteroid eye drops after eye surgery, and more intensive topical steroid treatment in severe inflammation. While <span class="hlt">cyclodextrins</span> have been known for more than <span class="hlt">a</span> century, their use in ophthalmology is just starting. <span class="hlt">Cyclodextrins</span> are useful excipients in eye drop formulations for <span class="hlt">a</span> variety of lipophilic drugs. They will facilitate eye drop formulations for drugs that otherwise might not be available for topical use, while improving absorption and stability and decreasing</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://www.ars.usda.gov/research/publications/publication/?seqNo115=303649','TEKTRAN'); return false;" href="http://www.ars.usda.gov/research/publications/publication/?seqNo115=303649"><span><span class="hlt">A</span> thermostable <span class="hlt">cyclodextrin</span> glycosyltransferase from Thermoanaerobacter sp. 5K</span></a></p> <p><a target="_blank" href="https://www.ars.usda.gov/research/publications/find-a-publication/">USDA-ARS?s Scientific Manuscript database</a></p> <p></p> <p></p> <p><span class="hlt">Cyclodextrin</span> glycosyltransferase (CGTase) from the thermophilic anaerobe Thermoanaerobacter sp. 5K was purified and characterized. The enzyme was purified with ammonium sulfate precipitation followed by <span class="hlt">a</span>-CD-bound, epoxy-activated Sepharose 6B affinity chromatography. Molecular weight of the purifie...</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29112365','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29112365"><span>Nanopyroxene Grafting with β-<span class="hlt">Cyclodextrin</span> Monomer for Wastewater Applications.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Nafie, Ghada; Vitale, Gerardo; Carbognani Ortega, Lante; Nassar, Nashaat N</p> <p>2017-12-06</p> <p>Emerging nanoparticle technology provides opportunities for environmentally friendly wastewater treatment applications, including those in the large liquid tailings containments in the Alberta oil sands. In this study, we synthesize β-<span class="hlt">cyclodextrin</span> grafted nanopyroxenes to offer an ecofriendly platform for the selective removal of organic <span class="hlt">compounds</span> typically present in these types of applications. We carry out computational modeling at the micro level through molecular mechanics and molecular dynamics simulations and laboratory experiments at the macro level to understand the interactions between the synthesized nanomaterials and two-model naphthenic acid molecules (cyclopentanecarboxylic and trans-4-pentylcyclohexanecarboxylic acids) typically existing in tailing ponds. The proof-of-concept computational modeling and experiments demonstrate that monomer grafted nanopyroxene  or nano-AE of the sodium iron-silicate aegirine are found to be promising candidates for the removal of polar organic <span class="hlt">compounds</span> from wastewater, among other applications. These nano-AE offer new possibilities for treating tailing ponds generated by the oil sands industry.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29680944','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29680944"><span>Effect of terbinafine on the biosynthetic pathway of isoprenoid <span class="hlt">compounds</span> in carrot suspension cultured cells.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Miras-Moreno, Begoña; Almagro, Lorena; Pedreño, María Angeles; Sabater-Jara, Ana Belén</p> <p>2018-07-01</p> <p>Terbinafine induced <span class="hlt">a</span> significant increase of squalene production. Terbinafine increased the expression levels of squalene synthase. <span class="hlt">Cyclodextrins</span> did not work as elicitors due to the gene expression levels obtained. Plant sterols are essential components of membrane lipids, which contributing to their fluidity and permeability. Besides their cholesterol-lowering properties, they also have anti-inflammatory, antidiabetic and anticancer activities. Squalene, which is phytosterol precursor, is widely used in medicine, foods and cosmetics due to its anti-tumor, antioxidant and anti-aging activities. Nowadays, vegetable oils constitute the main sources of phytosterols and squalene, but their isolation and purification involve complex extraction protocols and high costs. In this work, Daucus carota cell cultures were used to evaluate the effect of <span class="hlt">cyclodextrins</span> and terbinafine on the production and accumulation of squalene and phytosterols as well as the expression levels of squalene synthase and cycloartenol synthase genes. D. carota cell cultures were able to produce high levels of extracellular being phytosterols in the presence of <span class="hlt">cyclodextrins</span> (12 mg/L), these <span class="hlt">compounds</span> able to increase both the secretion and accumulation of phytosterols in the culture medium. Moreover, terbinafine induced <span class="hlt">a</span> significant increase in intracellular squalene production, as seen after 168 h of treatment (497.0 ± 23.5 µg g dry weight -1 ) while its extracellular production only increased in the presence of <span class="hlt">cyclodextrins</span>.The analysis of sqs and cas gene expression revealed that <span class="hlt">cyclodextrins</span> did not induce genes encoding enzymes involved in the phytosterol biosynthetic pathway since the expression levels of sqs and cas genes in <span class="hlt">cyclodextrin</span>-treated cells were lower than in control cells. The results, therefore, suggest that <span class="hlt">cyclodextrins</span> were only able to release phytosterols from the cells to the extracellular medium, thus contributing to their acumulation. To sum up, D. carota</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27037956','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27037956"><span><span class="hlt">Cyclodextrins</span> as Protective Agents of Protein Aggregation: An Overview.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Oliveri, Valentina; Vecchio, Graziella</p> <p>2016-06-06</p> <p><span class="hlt">Cyclodextrins</span> are extensively used in different fields (e.g., catalysis, chromatography, pharma, supramolecular chemistry, bioorganic chemistry, and bioinorganic chemistry), and their applications have been widely reviewed. Their main application in the field of pharmaceutical is as <span class="hlt">a</span> drug carrier. This review overviews, for the first time, the use of <span class="hlt">cyclodextrins</span> and their derivatives as antiaggregant agents in <span class="hlt">a</span> number of proteins (e.g., amyloid-β, insulin, recombinant human growth hormone, prion protein, transthyretin, and α-synuclein) and some multimeric enzymes. There are many diseases that are correlated to protein misfolding and amyloid formation processes affecting numerous organs and tissues. There are over 30 different amyloid proteins and <span class="hlt">a</span> number of corresponding diseases. Alzheimer's disease is the most common neurodegenerative disease. Treatment of these diseases is still <span class="hlt">a</span> goal to reach, and many molecules are studied in this perspective. <span class="hlt">Cyclodextrins</span> have also been studied, and they show great potential; as such, further studies could be very promising. This review aims to be <span class="hlt">a</span> stimulus for the design of new <span class="hlt">cyclodextrin</span> derivatives to obtain multifunctional systems with antiaggregant activity. © 2016 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28183619','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28183619"><span>Self-healing pH-sensitive poly[(methyl vinyl ether)-alt-(maleic acid)]-based supramolecular hydrogels formed by <span class="hlt">inclusion</span> complexation between <span class="hlt">cyclodextrin</span> and adamantane.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ma, Xiaoe; Zhou, Naizhen; Zhang, Tianzhu; Hu, Wanjun; Gu, Ning</p> <p>2017-04-01</p> <p>Self-healing materials are of interest for drug delivery, cell and gene therapy, tissue engineering, and other biomedical applications. In this work, on the base of biocompatible polymer poly(methyl vinyl ether-alt-maleic acid) (P(MVE-alt-MA)), host polymer β-<span class="hlt">cyclodextrin</span>-grafted P(MVE-alt-MA) (P(MVE-alt-MA)-g-β-CD) and guest polymer adamantane-grafted P(MVE-alt-MA) (P(MVE-alt-MA)-g-Ad) were first prepared. Then through taking advantage of the traditional host-guest interaction of β-<span class="hlt">cyclodextrin</span> and adamantane, <span class="hlt">a</span> novel self-healing pH-sensitive physical P(MVE-alt-MA)-g-β-CD/P(MVE-alt-MA)-g-Ad supramolecular hydrogels were obtained after simply mixing the aqueous solution of host polymer and guest polymer. This kind of supramolecular hydrogels not only possess pH-sensitivity, but also possess the ability to repair themselves after being damaged. Copyright © 2016 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23792039','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23792039"><span>Effect of 18β-glycyrrhetinic acid and hydroxypropyl γ<span class="hlt">cyclodextrin</span> complex on indomethacin-induced small intestinal injury in mice.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ishida, Tsukasa; Miki, Ikuya; Tanahashi, Toshihito; Yagi, Saori; Kondo, Yasuyuki; Inoue, Jun; Kawauchi, Shoji; Nishiumi, Sin; Yoshida, Masaru; Maeda, Hideko; Tode, Chisato; Takeuchi, Atsuko; Nakayama, Hirokazu; Azuma, Takeshi; Mizuno, Shigeto</p> <p>2013-08-15</p> <p>Non-steroidal anti-inflammatory drugs (NSAIDs)-induced small intestinal injury is <span class="hlt">a</span> serious clinical event with recent advances of diagnostic technologies, but <span class="hlt">a</span> successful therapeutic method to treat such injuries is still lacking. Licorice, <span class="hlt">a</span> traditional herbal medicine, and its derivatives have been widely used for the treatment of <span class="hlt">a</span> variety of diseases due to their extensive biological actions. However, it is unknown whether these derivatives have an effect on NSAIDs-induced small intestinal damage. Previously, the anti-inflammatory effects of three <span class="hlt">compounds</span> extracted from the licorice root, glycyrrhizin, 18β-glycyrrhetinic acid, and dipotassium glycyrrhizinate, were compared in vitro cell culture. The most prominent inhibitory effect on the tumor necrosis factor-α (TNF-α) production was observed with the administration of 18β-glycyrrhetinic acid as an active metabolite of glycyrrhizin. In this study, <span class="hlt">a</span> complex <span class="hlt">compound</span> of 18β-glycyrrhetinic acid and hydroxypropyl γ<span class="hlt">cyclodextrin</span> was examined to improve the oral bioavailability. After administration of this complex to indomethacin treated mice, <span class="hlt">a</span> significantly high plasma concentration of 18β-glycyrrhetinic acid was detected using the tandem mass spectrometry coupled with the HPLC. Furthermore, the complex form of 18β-glycyrrhetinic acid and hydroxypropyl γ<span class="hlt">cyclodextrin</span> reduced mRNA expressions of TNF-α, interleukin (IL)-1β, and IL-6, which was histologically confirmed in the improvement of indomethacin-induced small intestinal damage. These results suggest that the complex of 18β-glycyrrhetinic acid and hydroxypropyl γ<span class="hlt">cyclodextrin</span> has the potential therapeutic value for preventing the adverse effects of indomethacin-induced small intestinal injury. Copyright © 2013 Elsevier B.V. All rights reserved.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_18");'>18</a></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li class="active"><span>20</span></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_20 --> <div id="page_21" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li class="active"><span>21</span></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="401"> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2017JMoSt1128..239L','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2017JMoSt1128..239L"><span>Synthesis, characterization and biological activity of Rhein-<span class="hlt">cyclodextrin</span> conjugate</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Liu, Manshuo; Lv, Pin; Liao, Rongqiang; Zhao, Yulin; Yang, Bo</p> <p>2017-01-01</p> <p><span class="hlt">Cyclodextrin</span> conjugate complexation is <span class="hlt">a</span> useful method to enhance the solubility and absorption of poorly soluble drugs. <span class="hlt">A</span> series of new Rhein-β-<span class="hlt">cyclodextrin</span> conjugates (Rh-CD conjugates) have been synthesized and examined. Rhein is covalently linked with the β-CD by amido linkage in <span class="hlt">a</span> 1:1 molar ratio. The conjugates were characterized by 1H NMR, 13C NMR, HRMS, powder X-ray diffraction (powder XRD) as well as thermogravimetric analysis (TGA). The results reveal that incorporation of β-CD could improve the aqueous solubility of Rhein and the cytotoxicity against hepatocellular carcinoma (HepG2) cell line as well as antibacterial activity against three organisms. The improved biological activity and the satisfactory water solubility of the conjugates will be potentially useful for developing novel drug-<span class="hlt">cyclodextrin</span> conjugates, such as herbal medicine.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23560535','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23560535"><span>Synthesis, characterization, and evaluation of pluronic-based β-<span class="hlt">cyclodextrin</span> polyrotaxanes for mobilization of accumulated cholesterol from Niemann-Pick type C fibroblasts.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Collins, Christopher J; McCauliff, Leslie A; Hyun, Seok-Hee; Zhang, Zhaorui; Paul, Lake N; Kulkarni, Aditya; Zick, Klaus; Wirth, Mary; Storch, Judith; Thompson, David H</p> <p>2013-05-14</p> <p>Several lines of evidence suggest that β-<span class="hlt">cyclodextrin</span> (β-CD) derivatives initiate the efflux of accumulated, unesterified cholesterol from the late endosomal/lysosomal compartment in Niemann Pick C (NPC) disease models. Unfortunately, repeated injections or continuous infusions of current β-CD therapies are required to sustain suppression of symptoms and prolong life. In an effort to make CD treatment <span class="hlt">a</span> more viable option by boosting efficacy and improving pharmacokinetics, <span class="hlt">a</span> library of Pluronic surfactant-based β-CD polyrotaxanes has been developed using biocompatible poly(ethylene glycol) (PEG)-polypropylene glycol (PPG)-PEG triblock copolymers. These <span class="hlt">compounds</span> carry multiple copies of β-CD as shown by (1)H NMR, 2D nuclear Overhouser effect spectroscopy, gel permeation chromatography/multiangle light scattering, analytical ultracentrifugation analysis, matrix assisted laser desorption/ionization mass spectrometry, and diffusion-ordered spectroscopy. Analyses of free β-<span class="hlt">cyclodextrin</span> contamination in the <span class="hlt">compounds</span> were made by reverse phase high pressure liquid chromatography and hydrophilic interaction liquid chromatography. Dethreading kinetics were studied by reverse phase high pressure liquid chromatography, UV/vis, and (1)H NMR analysis. Filipin staining studies using npc2(-/-) fibroblasts show significant reversal of cholesterol accumulation after treatment with polyrotaxane <span class="hlt">compounds</span>. The rate and efficacy of reversal is similar to that achieved by equivalent amounts of monomeric β-CD alone.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23925928','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23925928"><span>Mycelium growth stimulation of the desert truffle Terfezia claveryi chatin by β-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>López-Nicolás, José Manuel; Pérez-Gilabert, Manuela; García-Carmona, Francisco; Lozano-Carrillo, María Cecilia; Morte, Asunción</p> <p>2013-01-01</p> <p>The commercial value of Terfezia claveryi, an edible desert truffle with important gastronomic, nutritional, and antioxidant properties, has led to growing interest in its cultivation. The erratic and slow growth of T. claveryi mycelium in vitro represents an impairment to obtain mycorrhizal plants, and it makes necessary to find <span class="hlt">a</span> new culture medium able to overcome these drawbacks. In this work, we analyze the effect of <span class="hlt">cyclodextrins</span> (CDs) on the growth of T. claveryi mycelium. Different parameters, including colony diameter, growth rate, and colony fresh weight, were evaluated, both in the presence and absence of these encapsulant agents. The results obtained confirm the ability of CDs to stimulate the growth of T. claveryi mycelium when present in the culture medium. <span class="hlt">A</span> similar effect was observed when CDs were added to the culture medium of Tuber melanosporum. Three natural (α-, β-, and γ) and two modified (hydroxypropil-β and methyl-β) CDs were assayed. The best results were obtained with β-<span class="hlt">cyclodextrin</span>, but no improvement was observed with its chemically modified derivatives. CDs complex the different <span class="hlt">compounds</span> present in the culture medium which impair mycelial growth. © 2013 American Institute of Chemical Engineers.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27685788','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27685788"><span>Enhancement of orofacial antinociceptive effect of carvacrol, <span class="hlt">a</span> monoterpene present in oregano and thyme oils, by β-<span class="hlt">cyclodextrin</span> <span class="hlt">inclusion</span> complex in mice.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Silva, Juliane C; Almeida, Jackson R G S; Quintans, Jullyana S S; Gopalsamy, Rajiv Gandhi; Shanmugam, Saravanan; Serafini, Mairim Russo; Oliveira, Maria R C; Silva, Bruno A F; Martins, Anita O B P B; Castro, Fyama F; Menezes, Irwin R A; Coutinho, Henrique D M; Oliveira, Rita C M; Thangaraj, Parimelazhagan; Araújo, Adriano A S; Quintans-Júnior, Lucindo J</p> <p>2016-12-01</p> <p>Orofacial pain is associated with diagnosis of chronic pain of head, face, mouth, neck and all the intraoral structures. Carvacrol, <span class="hlt">a</span> naturally occurring isoprenoid with diverse class of biological activities including anti-inflammatory, analgesic, antitumor and antioxidant properties. Now, the antinociceptive effect was studied in mice pretreatment with carvacrol (CARV) and β-<span class="hlt">cyclodextrin</span> complex containing carvacrol (CARV-βCD) in formalin-, capsaicin-, and glutamate- induced orofacial nociception. Mice were pretreated with vehicle (0.9% Nacl, p.o.), CARV (10 and 20mg/kg, p.o.), CARV-βCD (10 and 20mg/kg, p.o.) or MOR (10mg/kg, i.p.) before the nociceptive behavior induced by subcutaneous injections (s.c.) of formalin (20μl, 2%), capsaicin (20μl, 2.5μg) or glutamate (20μl, 25μM) into the upper lip respectively. The interference on motor coordination was determined using rotarod and grip strength meter apparatus. CARV-βCD reduced the nociceptive during the two phases of the formalin test, whereas CARV did not produced the reduction in face-rubbing behavior in the initial phase. CARV-βCD (20mg/kg, p.o.) produced 49.3% behavior pain while CARV alone at 20mg/kg, p.o, produced 28.7% of analgesic inhibition in the second phase of formalin test. CARV, CARV-βCD and Morphine (MOR) showed <span class="hlt">a</span> significant reduction against nociception caused by capsaicin or glutamate injection. Thus the encapsulation of carvacrol in β-<span class="hlt">cyclodextrin</span> can acts as <span class="hlt">a</span> considerable therapeutic agent with pharmacological interest for the orofacial pain management. Copyright © 2016 Elsevier Masson SAS. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24673836','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24673836"><span>Anaesthetic efficacy of bupivacaine 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span> for dental anaesthesia after inferior alveolar nerve block in rats.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Serpe, L; Franz-Montan, M; Santos, C P dos; Silva, C B da; Nolasco, F P; Caldas, C S; Volpato, M C; Paula, E de; Groppo, F C</p> <p>2014-05-01</p> <p>Bupivacaine is <span class="hlt">a</span> long-acting local anaesthetic that is widely used in medicine and dentistry. The duration and intensity of its sensory blockade in animal models is increased by its <span class="hlt">inclusion</span> in complexes with <span class="hlt">cyclodextrins</span>. The aim of the present study was to evaluate the anaesthetic efficacy of bupivacaine 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HPβCD) <span class="hlt">inclusion</span> complex for dental anaesthesia after inferior alveolar nerve block in rats. Thirty rats were each given an injection close to the mandibular foramen of 0.2ml of one of the following formulations: 0.5% bupivacaine alone; 0.5% bupivacaine with 1:200,000 epinephrine; and 0.5% bupivacaine-HPβCD <span class="hlt">inclusion</span> complex (bupivacaine-HPβCD). The other sides were used as controls, with either 0.9% saline or anaesthetic-free HPβCD solution being injected. The onset, success, and duration of pulpal anaesthesia were assessed by electrical stimulation ("pulp tester") on inferior molars. Results were analysed using ANOVA (Tukey), log rank, and chi square tests (α=5%). There were no differences among the formulations in onset of anaesthesia (p=0.59) or between the bupivacaine plus epinephrine and bupivacaine plus HPβCD in duration of anaesthesia, but bupivacaine plus epinephrine gave significantly higher values than bupivacaine alone (p=0.007). Bupivacaine plus epinephrine was <span class="hlt">a</span> better anaesthetic than bupivacaine alone (p=0.02), while Bupi-HPβCD gave intermediate results, and therefore did not differ significantly from the other 2 groups (p=0.18 with bupivacaine alone; and p=0.44 with bupivacaine plus epinephrine). The bupivacaine-HPβCD complex showed similar anaesthetic properties to those of bupivacaine with epinephrine. Copyright © 2014 The British Association of Oral and Maxillofacial Surgeons. Published by Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4590818','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4590818"><span>Solubility Enhancement of Raloxifene Using <span class="hlt">Inclusion</span> Complexes and Cogrinding Method</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Patil, Payal H.; Belgamwar, Veena S.; Patil, Pratibha R.; Surana, Sanjay J.</p> <p>2013-01-01</p> <p>The objective of the present work was to enhance the solubility and dissolution of practically water-insoluble drug raloxifene HCl (RLX), for the same two approaches that were used. In the first approach, drug was kneaded with hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HPβCD), and in the second one drug was cogrinded with modified guar gum (MGG). The drug-<span class="hlt">cyclodextrin</span> complex and drug-MGG cogrind mixtures were characterized by differential scanning calorimetry, X-ray diffraction studies, scanning electron microscopy, and Fourier transform infrared spectroscopy. The solubility and dissolution study reveals that solubility and dissolution rate of RLX remarkably increased in both methods. It was concluded that the prepared <span class="hlt">inclusion</span> complex showed <span class="hlt">a</span> remarkable increase in solubility and dissolution of poorly water-soluble drug raloxifene. In the cogrinding mixture, <span class="hlt">a</span> natural modified gum is used as <span class="hlt">a</span> surfactant and enhances the solubility and dissolution of RLX without requiring addition of organic solvent or high temperature for its preparation; thus, process is less cumbersome and cost effective. But when both methods were compared; HPβCD complexation method showed significant enhancement of drug solubility. PMID:26555984</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28411478','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28411478"><span><span class="hlt">A</span> supramolecular nanoparticle system based on β-<span class="hlt">cyclodextrin</span>-conjugated poly-l-lysine and hyaluronic acid for co-delivery of gene and chemotherapy agent targeting hepatocellular carcinoma.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Xiong, Qingqing; Cui, Mangmang; Bai, Yang; Liu, Yuanyuan; Liu, Di; Song, Tianqiang</p> <p>2017-07-01</p> <p><span class="hlt">A</span> novel supramolecular nanoparticle system with core-shell structure was designed based on β-<span class="hlt">cyclodextrin</span>-conjugated poly-l-lysine (PLCD) and hyaluronic acid for co-delivery of gene and chemotherapy agent targeting hepatocellular carcinoma (HCC). PLCD was synthesized by the conjugation of monoaldehyde activated β-<span class="hlt">cyclodextrin</span> with poly-l-lysine via Shiff's base reaction. Doxorubicin, as <span class="hlt">a</span> model therapeutic drug, was included into the hydrophobic cavity of β-<span class="hlt">cyclodextrin</span> in PLCD through host-guest interaction. OligoRNA, as <span class="hlt">a</span> model gene, was further condensed into the <span class="hlt">inclusion</span> complexes by electrostatic interaction to form oligoRNA and doxorubicin co-loaded supramolecular nanoparticle system. Hyaluronic acid, which is often over-expressed by HCC cells, was coated on the surface of the above nanoparticles to construct HCC-targeted nanoparticle system. These nanoparticles had regular spherical shape with classic "core-shell" structure, and their size and zeta potential were 195.8nm and -22.7mV, respectively. The nanoparticles could effectively deliver doxorubicin and oligoRNA into HCC cells via CD44 receptor-mediated endocytosis and significantly inhibit the cell proliferation. In the nude mice bearing MHCC-97H tumor, the nanoparticles could be efficiently accumulated in the tumor, suggesting their strong hepatoma-targeting capability. These findings demonstrated that this novel supramolecular nanoparticle system had <span class="hlt">a</span> promising potential for combining gene therapy and chemotherapy to treat HCC. Copyright © 2017 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26935589','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26935589"><span>Capillary electrophoretic enantioseparation of basic drugs using <span class="hlt">a</span> new single-isomer <span class="hlt">cyclodextrin</span> derivative and theoretical study of the chiral recognition mechanism.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Liu, Yongjing; Deng, Miaoduo; Yu, Jia; Jiang, Zhen; Guo, Xingjie</p> <p>2016-05-01</p> <p><span class="hlt">A</span> novel single-isomer <span class="hlt">cyclodextrin</span> derivative, heptakis {2,6-di-O-[3-(1,3-dicarboxyl propylamino)-2-hydroxypropyl]}-β-<span class="hlt">cyclodextrin</span> (glutamic acid-β-<span class="hlt">cyclodextrin</span>) was synthesized and used as <span class="hlt">a</span> chiral selector in capillary electrophoresis for the enantioseparation of 12 basic drugs, including terbutaline, clorprenaline, tulobuterol, clenbuterol, procaterol, carvedilol, econazole, miconazole, homatropine methyl bromide, brompheniramine, chlorpheniramine and pheniramine. The primary factors affecting separation efficiency, which include the background electrolyte pH, the concentration of glutamic acid-β-<span class="hlt">cyclodextrin</span> and phosphate buffer concentration, were investigated. Satisfactory enantioseparations were obtained using an uncoated fused-silica capillary of 50 cm (effective length 40 cm) × 50 μm id with 120 mM phosphate buffer (pH 2.5-4.0) containing 0.5-4.5 mM glutamic acid-β-<span class="hlt">cyclodextrin</span> as background electrolyte. <span class="hlt">A</span> voltage of 20 kV was applied and the capillary temperature was kept at 20°C. The results proved that glutamic acid-β-<span class="hlt">cyclodextrin</span> was an effective chiral selector for studied 12 basic drugs. Moreover, the possible chiral recognition mechanism of brompheniramine, chlorpheniramine and pheniramine on glutamic acid-β-<span class="hlt">cyclodextrin</span> was investigated using the semi-empirical Parametric Method 3. © 2016 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28450165','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28450165"><span>Effect of guest drug character encapsulated in the cavity and intermolecular spaces of γ-<span class="hlt">cyclodextrins</span> on the dissolution property of ternary γ-<span class="hlt">cyclodextrin</span> complex.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Liu, Nan; Higashi, Kenjirou; Ueda, Keisuke; Moribe, Kunikazu</p> <p>2017-10-15</p> <p>Various ternary Guest 2/(Guest 1/γ-<span class="hlt">cyclodextrin</span> (CD)) complexes were prepared using <span class="hlt">a</span> cogrinding and subsequent heating method, wherein Guest 1 was incorporated in the cavity of γ-CD and Guest 2 was incorporated into the intermolecular spaces between γ-CD columns. Dissolution fluxes of Guest 1 and Guest 2 from all ternary complexes were almost identical. The dissolution flux of flurbiprofen (Guest 1) from the ternary complexes depended on the solubility of Guest 2 drugs (naproxen<ketoprofen<ethenzamide) in the dissolution medium of pH 1.2. It is noteworthy that the dissolution flux of flurbiprofen from the ternary complexes with ketoprofen and ethenzamide as Guest 2 drugs was further enhanced compared with that from the flurbiprofen/γ-CD <span class="hlt">inclusion</span> complex. The ternary complex of the acidic drug ketoprofen as Guest 1 and the neutral drug hydrocortisone as Guest 2 showed an increased dissolution flux, which was dependent on the increase in pH of the dissolution medium. The pH-dependent dissolution should reflect the solubility of ketoprofen/γ-CD <span class="hlt">inclusion</span> complex in each dissolution medium. These results indicated that the dissolution flux of the ternary γ-CD complexes could be controlled by selecting the appropriate Guest 1 and Guest 2 species. Copyright © 2017 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.osti.gov/biblio/335327-cyclodextrin-enhanced-solubilization-removal-residual-phase-chlorinated-solvents-from-porous-media','SCIGOV-STC'); return false;" href="https://www.osti.gov/biblio/335327-cyclodextrin-enhanced-solubilization-removal-residual-phase-chlorinated-solvents-from-porous-media"><span><span class="hlt">Cyclodextrin</span>-enhanced solubilization and removal of residual-phase chlorinated solvents from porous media</span></a></p> <p><a target="_blank" href="http://www.osti.gov/search">DOE Office of Scientific and Technical Information (OSTI.GOV)</a></p> <p>Boving, T.B.; Wang, X.; Brusseau, M.L.</p> <p>1999-03-01</p> <p>The development of improved methods for remediation of contaminated aquifers has emerged as <span class="hlt">a</span> significant environmental priority. One technology that appears to have considerable promise involves the use of solubilization agents such as surfactants and cosolvents for enhancing the removal of residual phase immiscible liquids. The authors examined the use of <span class="hlt">cyclodextrin</span>, <span class="hlt">a</span> glucose-based molecule, for solubilizing and removing residual-phase immiscible liquid from porous media. Batch experiments were conducted to measure the degree of trichloroethene (TCE) and tetrachloroethene (PCE) solubilization induced by hydroxypropyl-{beta}-<span class="hlt">cyclodextrin</span> (HPCD) and methyl-{beta}-<span class="hlt">cyclodextrin</span> (MCD). These studies revealed that the solubilities of TCE and PCE were enhanced bymore » up to 9.5 and 36.0 times, respectively. Column experiments were conducted to compare water and <span class="hlt">cyclodextrin</span>-enhanced flushing of Borden sand containing residual saturations of TCE and PCE. The results indicate that solubilization and mass removal were enhanced substantially with the use of <span class="hlt">cyclodextrins</span>. The effluent concentrations during the steady-state phase of the HPCD and MCD flushing experiments were close to the apparent solubilities measured with the batch experiments, indicating equilibrium concentrations were maintained during the initial phase of <span class="hlt">cyclodextrin</span> flushing. Mobilization was observed for only the TCE-MCD and PCE-5%MCD experiments.« less</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/15768437','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/15768437"><span>Temperature sensitive poly[N-isopropylacrylamide-co-(acryloyl beta-<span class="hlt">cyclodextrin</span>)] for improved drug release.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhang, Jian-Tao; Huang, Shi-Wen; Liu, Ji; Zhuo, Ren-Xi</p> <p>2005-03-15</p> <p>The model drugs ibuprofen (IBU) and tegafur (T-Fu) were loaded into poly[N-isopropylacrylamide-co-(acryloyl beta-<span class="hlt">cyclodextrin</span>)] [P(NIPA-co-<span class="hlt">A</span>-CD)] and PNIPA hydrogels by immersing dried gels in IBU or T-Fu alcohol solutions until they reached equilibrium. Drug release studies were carried out in water at 25 degrees C. In contrast to the release time of conventional PNIPA hydrogel, that of IBU from the beta-CD incorporated hydrogel was significantly prolonged and the drug loading was also greatly increased, which may be the result of the formation of <span class="hlt">inclusion</span> complexes between CD and ibuprofen. However, another hydrophilic drug, tegafur, did not display these properties because it could not form <span class="hlt">a</span> complex with the CD groups. [diagram in text].</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25320456','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25320456"><span>Antidiabetic effect of the α-lipoic acid γ-<span class="hlt">cyclodextrin</span> complex.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Naito, Yuki; Ikuta, Naoko; Nakata, Daisuke; Terao, Keiji; Matsumoto, Kinuyo; Kajiwara, Naemi; Okano, Ayaka; Yasui, Hiroyuki; Yoshikawa, Yutaka</p> <p>2014-09-01</p> <p>In recent years, the number of patients suffering from diabetes mellitus has been increasing worldwide. In particular, type 2 diabetes mellitus, <span class="hlt">a</span> lifestyle-related disease, is recognized as <span class="hlt">a</span> serious disease with various complications. Many types of pharmaceutics or specific health foods have been used for the management of diabetes mellitus. At the same time, the relationship between diabetes mellitus and α-lipoic acid has been recognized for many years. In this study, we found that the α-lipoic acid γ-<span class="hlt">cyclodextrin</span> complex exhibited an Hb<span class="hlt">A</span>1c lowering effect for treating type 2 diabetes mellitus in animal models. Moreover, in this study, we investigated the activation of phosphorylation of AMP-activated protein kinase, which plays <span class="hlt">a</span> role in cellular energy homeostasis, in the liver of KKA(y) mice by using α-lipoic acid and the α-lipoic acid γ-<span class="hlt">cyclodextrin</span> complex. Our results show that the α-lipoic acid γ-<span class="hlt">cyclodextrin</span> complex strongly induced the phosphorylation of AMP-activated protein kinase. Thus, we concluded that intake of the α-lipoic acid γ-<span class="hlt">cyclodextrin</span> complex exerted an antidiabetic effect by suppressing the elevation of postprandial hyperglycemia as well as doing exercise.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/3393422','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/3393422"><span>Formation and antimicrobial activity of complexes of beta-<span class="hlt">cyclodextrin</span> and some antimycotic imidazole derivatives.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Van Doorne, H; Bosch, E H; Lerk, C F</p> <p>1988-04-22</p> <p>Complex formation between beta-<span class="hlt">cyclodextrin</span> and six antimycotic imidazole derivatives has been studied. The solubility of all drugs was increased in the presence of beta-<span class="hlt">cyclodextrin</span>. The smallest increase (approx. 5-fold) was observed for miconazol, and the largest increase (approx. 160-fold) was observed for bifonazol. Apparent 1:1-complex constants were measured and found to decrease in the order: bifonazol greater than ketoconazol greater than tioconazol greater than miconazol greater than itraconazol greater than clotrimazol. The complexes appeared to possess <span class="hlt">a</span> low, if any, antimicrobial activity. Measurement of inhibition zone sizes, with four test organisms was used to study the release of the antimycotic drugs from topical preparations. The antimycotic drugs were more readily released from topical preparations containing beta-<span class="hlt">cyclodextrin</span> than from the same vehicles without beta-<span class="hlt">cyclodextrin</span>. The rationale of beta-<span class="hlt">cyclodextrin</span> addition to antimycotic topical preparations is discussed.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/16859846','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/16859846"><span><span class="hlt">Cyclodextrin</span>-insulin complex encapsulated polymethacrylic acid based nanoparticles for oral insulin delivery.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sajeesh, S; Sharma, Chandra P</p> <p>2006-11-15</p> <p>Present investigation was aimed at developing an oral insulin delivery system based on hydroxypropyl beta <span class="hlt">cyclodextrin</span>-insulin (HPbetaCD-I) complex encapsulated polymethacrylic acid-chitosan-polyether (polyethylene glycol-polypropylene glycol copolymer) (PMCP) nanoparticles. Nanoparticles were prepared by the free radical polymerization of methacrylic acid in presence of chitosan and polyether in <span class="hlt">a</span> solvent/surfactant free medium. Dynamic light scattering (DLS) experiment was conducted with particles dispersed in phosphate buffer (pH 7.4) and size distribution curve was observed in the range of 500-800 nm. HPbetaCD was used to prepare non-covalent <span class="hlt">inclusion</span> complex with insulin and complex was analyzed by Fourier transform infrared (FTIR) and fluorescence spectroscopic studies. HPbetaCD complexed insulin was encapsulated into PMCP nanoparticles by diffusion filling method and their in vitro release profile was evaluated at acidic/alkaline pH. PMCP nanoparticles displayed good insulin encapsulation efficiency and release profile was largely dependent on the pH of the medium. Enzyme linked immunosorbent assay (ELISA) study demonstrated that insulin encapsulated inside the particles was biologically active. Trypsin inhibitory effect of PMCP nanoparticles was evaluated using N-alpha-benzoyl-L-arginine ethyl ester (BAEE) and casein as substrates. Mucoadhesive studies of PMCP nanoparticles were conducted using freshly excised rat intestinal mucosa and the particles were found fairly adhesive. From the preliminary studies, <span class="hlt">cyclodextrin</span> complexed insulin encapsulated mucoadhesive nanoparticles appear to be <span class="hlt">a</span> good candidate for oral insulin delivery.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/21838803','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/21838803"><span>Probing of some <span class="hlt">compounds</span> as anti-aggregatory additives in the protein refolding process from Escherichia coli <span class="hlt">inclusion</span> bodies.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zilinskas, Albinas; Sereikaite, Jolanta</p> <p>2011-01-01</p> <p>Five <span class="hlt">compounds</span> of different chemical structure were tested for aggregation suppression during the refolding of porcine and mink growth hormones as model proteins from Escherichia coli <span class="hlt">inclusion</span> bodies by the dilution method. Of all <span class="hlt">compounds</span> tested in this work, 3-guanidinopropionic acid (GPA) containing <span class="hlt">a</span> guanidinium group was the most effective additive for aggregation suppression. Anti-aggregatory properties of GPA were compared with the ones of l-arginine. Copyright © 2011 International Union of Biochemistry and Molecular Biology, Inc.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3732634','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3732634"><span>Preparation and <span class="hlt">Cyclodextrin</span> Solubilization of the Antibacterial Agent Benzoyl Metronidazole</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Yang, Shuo</p> <p>2013-01-01</p> <p><span class="hlt">A</span> one-pot method for the preparation of benzoyl metronidazole was achieved by using N,N′-carbonyldiimidazole as <span class="hlt">a</span> coupling reagent. Moreover, it was found that the byproduct imidazole as the catalyst promoted the reaction. In addition, the β-<span class="hlt">cyclodextrin</span> solubilization of benzoyl metronidazole was investigated by phase-solubility method. The phase-solubility studies indicated that the solubility of benzoyl metronidazole (S = 0.1435 g/L) was substantially increased 9.7-fold (S′ = 1.3881 g/L) by formation of 1 : 1 benzoyl metronidazole/β-<span class="hlt">cyclodextrin</span> complexes in water, and the association constant K <span class="hlt">a</span> value was determined to be 251 (±23) dm3/mol. Therefore, β-<span class="hlt">cyclodextrin</span> can work as <span class="hlt">a</span> pharmaceutical solubilizer for benzoyl metronidazole and may improve its oral bioavailability. PMID:23970831</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19495987','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19495987"><span>Effect of <span class="hlt">cyclodextrin</span> complexation of curcumin on its solubility and antiangiogenic and anti-inflammatory activity in rat colitis model.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Yadav, Vivek R; Suresh, Sarasija; Devi, Kshama; Yadav, Seema</p> <p>2009-01-01</p> <p>The purpose of the study was to prepare and evaluate the anti-inflammatory activity of <span class="hlt">cyclodextrin</span> (CD) complex of curcumin for the treatment of inflammatory bowel disease (IBD) in colitis-induced rat model. <span class="hlt">Inclusion</span> complexes of curcumin were prepared by common solvent and kneading methods. These complexes were further evaluated for increase in solubility of poorly soluble curcumin. The <span class="hlt">inclusion</span> complexes were characterized for enhancement in solubility, in vitro dissolution, surface morphology, infrared, differential scanning calorimetry, and X-ray studies. Solubility, phase solubility, and in vitro dissolution studies showed that curcumin has higher affinity for hydroxypropyl-beta-CD (HPbetaCD) than other CDs. HPbetaCD complex of curcumin was further investigated for its antiangiogenic and anti-inflammatory activity using chick embryo and rat colitis model. HPbetaCD complex of curcumin proved to be <span class="hlt">a</span> potent angioinhibitory <span class="hlt">compound</span>, as demonstrated by inhibition of angiogenesis in chorioallantoic membrane assay. Curcumin- and HPbetaCD-treated rats showed <span class="hlt">a</span> faster weight gain compared to dextran sulfate solution (DSS) controls. Whole colon length appeared to be significantly longer in HPbetaCD-treated rats than pure curcumin and DSS controls. An additional finding in the DSS-treated rats was the predominance of eosinophils in the chronic cell infiltrate. Decreased mast cell numbers in the mucosa of the colon of CD of curcumin- and pure-curcumin-treated rats was observed. This study concluded that the degree of colitis caused by administration of DSS was significantly attenuated by CD of curcumin. Being <span class="hlt">a</span> nontoxic natural dietary product, curcumin could be useful in the therapeutic strategy for IBD patients.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4319568','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4319568"><span>Synthesis, Characterization, and Evaluation of Pluronic-Based β-<span class="hlt">Cyclodextrin</span> Polyrotaxanes for Mobilization of Accumulated Cholesterol from Niemann-Pick Type C Fibroblasts</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Collins, Christopher J.; McCauliff, Leslie A.; Hyun, Seok-Hee; Zhang, Zhaorui; Paul, Lake N.; Kulkarni, Aditya; Zick, Klaus; Wirth, Mary; Storch, Judith; Thompson, David H.</p> <p>2015-01-01</p> <p>Several lines of evidence suggest that β-<span class="hlt">cyclodextrin</span> (β-CD) derivatives initiate the efflux of accumulated, unesterified cholesterol from the late endosomal/lysosomal compartment in Niemann Pick C (NPC) disease models. Unfortunately, repeated injections or continuous infusions of current β-CD therapies are required to sustain suppression of symptoms and prolong life. In an effort to make CD treatment <span class="hlt">a</span> more viable option by boosting efficacy and improving pharmacokinetics, <span class="hlt">a</span> library of Pluronic surfactant-based β-CD polyrotaxanes has been developed using biocompatible poly(ethylene glycol) (PEG)–polypropylene glycol (PPG)–PEG triblock copolymers. These <span class="hlt">compounds</span> carry multiple copies of β-CD as shown by 1H NMR, 2D nuclear Overhouser effect spectroscopy, gel permeation chromatography/multiangle light scattering, analytical ultracentrifugation analysis, matrix assisted laser desorption/ionization mass spectrometry, and diffusion-ordered spectroscopy. Analyses of free β-<span class="hlt">cyclodextrin</span> contamination in the <span class="hlt">compounds</span> were made by reverse phase high pressure liquid chromatography and hydrophilic interaction liquid chromatography. Dethreading kinetics were studied by reverse phase high pressure liquid chromatography, UV/vis, and 1H NMR analysis. Filipin staining studies using npc2−/− fibroblasts show significant reversal of cholesterol accumulation after treatment with polyrotaxane <span class="hlt">compounds</span>. The rate and efficacy of reversal is similar to that achieved by equivalent amounts of monomeric β-CD alone. PMID:23560535</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/16376902','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/16376902"><span>Measurement of monomolecular binding constants of neutral phenols into the beta-<span class="hlt">cyclodextrin</span> by continuous frontal analysis in capillary and microchip electrophoresis via <span class="hlt">a</span> competitive assay.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Le Saux, Thomas; Hisamoto, Hideaki; Terabe, Shigeru</p> <p>2006-02-03</p> <p>Measurement of binding constant by chip electrophoresis is <span class="hlt">a</span> very promising technique for the high throughput screening of non-covalent interactions. Among the different electrophoretic methods available that yield the binding parameters, continuous frontal analysis is the most appropriate for <span class="hlt">a</span> transposition from capillary electrophoresis (CE) to microchip electrophoresis. Implementation of this methodology in microchip was exemplified by the measurement of <span class="hlt">inclusion</span> constants of 2-naphtalenesulfonate and neutral phenols (phenol, 4-chlorophenol and 4-nitrophenol) into beta-<span class="hlt">cyclodextrin</span> by competitive assays. The issue of competitor choice is discussed in relation to its appropriateness for proper monitoring of the interaction.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24060538','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24060538"><span>Efficient synthesis of pure monotosylated beta-<span class="hlt">cyclodextrin</span> and its dimers.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tripodo, Giuseppe; Wischke, Christian; Neffe, Axel T; Lendlein, Andreas</p> <p>2013-11-15</p> <p>6-O-Monotosyl-β-<span class="hlt">cyclodextrin</span> (mono-Ts-βCD) is one of the most important intermediates in the production of substituted βCD. So far, performing the monotosylation reaction and, in particular, the purification steps was challenging, relied on toxic solvents, and resulted in long and expensive procedures at, importantly, low yields. Here, the reaction of <span class="hlt">cyclodextrin</span> with p-toluenesulfonyl chloride in aqueous environment is described to obtain <span class="hlt">a</span> highly pure mono-Ts-βCD, for which <span class="hlt">a</span> single-step purification with <span class="hlt">a</span> cation exchange resin was applied. With this synthetic route and purification, yields could be increased from typically <10-15% to 35%, and organic solvents could be avoided. As characterized by FTIR, mass spectrometry, elemental analysis, and NMR, mono-Ts-βCD was obtained with <span class="hlt">a</span> molar purity of >98mol%. From mono-Ts-βCD, β-<span class="hlt">cyclodextrin</span> dimers linked by ethylenediamine (bis-Et-βCD) were successfully prepared (yield 93%, purity 96mol%) in <span class="hlt">a</span> one-step approach using an anion exchange resin to trap leaving groups that typically interfere in the reaction. This synthesis procedure with <span class="hlt">a</span> direct collection of side-products may be <span class="hlt">a</span> general strategy applicable for nucleophilic substitution of tosylated <span class="hlt">cyclodextrins</span>. Copyright © 2013 Elsevier Ltd. All rights reserved.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_19");'>19</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li class="active"><span>21</span></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_21 --> <div id="page_22" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li class="active"><span>22</span></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="421"> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28093037','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28093037"><span>Encapsulation of lemongrass oil with <span class="hlt">cyclodextrins</span> by spray drying and its controlled release characteristics.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Phunpee, Sarunya; Ruktanonchai, Uracha Rangsadthong; Yoshii, Hidefumi; Assabumrungrat, Suttichai; Soottitantawat, Apinan</p> <p>2017-04-01</p> <p><span class="hlt">Inclusion</span> of the two isomers of citral (E-citral and Z-citral), components of lemongrass oil, was investigated within the confines of various <span class="hlt">cyclodextrin</span> (α-CD, β-CD and γ-CD) host molecules. Aqueous complex formation constants for E-citral with α-CD, β-CD and γ-CD were determined to be 123, 185, and 204 L/mol, respectively, whereas Z-citral exhibited stronger affinities (157, 206, and 253 L/mol, respectively). The binding trend γ-CD > β-CD > α-CD is <span class="hlt">a</span> reflection of the more favorable geometrical accommodation of the citral isomers with increasing cavity size. Encapsulation of lemongrass oil within CDs was undertaken through shaking citral:CD (1:1, 1.5:1, and 2:1 molar ratio) mixtures followed by spray drying. Maximum citral retention occurred at <span class="hlt">a</span> 1:1 molar ratio with β-CD and α-CD demonstrating the highest levels of total E-citral and Z-citral retention, respectively. Furthermore, the β-CD complex demonstrated the slowest release rate of all <span class="hlt">inclusion</span> complex powders.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2004JSSCh.177..366W','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2004JSSCh.177..366W"><span>Structure and thermal decomposition of sulfated β-<span class="hlt">cyclodextrin</span> intercalated in <span class="hlt">a</span> layered double hydroxide</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Wang, Ji; Wei, Min; Rao, Guoying; Evans, David G.; Duan, Xue</p> <p>2004-01-01</p> <p>The sodium salt of hexasulfated β-<span class="hlt">cyclodextrin</span> has been synthesized and intercalated into <span class="hlt">a</span> magnesium-aluminum layered double hydroxide by ion exchange. The structure, composition and thermal decomposition behavior of the intercalated material have been studied by variable temperature X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR), inductively coupled plasma emission spectroscopy (ICP), and thermal analysis (TG-DTA) and <span class="hlt">a</span> model for the structure has been proposed. The thermal stability of the intercalated sulfated β-<span class="hlt">cyclodextrin</span> is significantly enhanced compared with the pure form before intercalation.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28471055','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28471055"><span><span class="hlt">A</span> novel in situ strategy for the preparation of <span class="hlt">a</span> β-<span class="hlt">cyclodextrin</span>/polydopamine-coated capillary column for capillary electrochromatography enantioseparations.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Guo, Heying; Niu, Xiaoying; Pan, Congjie; Yi, Tao; Chen, Hongli; Chen, Xingguo</p> <p>2017-06-01</p> <p>Inspired by the chiral recognition ability of β-<span class="hlt">cyclodextrin</span> and the natural adhesive properties of polydopamine under alkaline conditions, in this study, <span class="hlt">a</span> rapid and in situ modification strategy was developed to fabricate β-<span class="hlt">cyclodextrin</span>/polydopamine composite material coated-capillary columns for open tubular capillary electrochromatography. The results of scanning electron microscopy, FTIR spectroscopy, streaming potential, and electro-osmotic flow studies indicated that β-<span class="hlt">cyclodextrin</span>/polydopamine was successfully fixed on the inner wall of the capillary column. This coating can be achieved within 1 h affording <span class="hlt">a</span> greatly reduced capillary preparation time. The performance of the β-<span class="hlt">cyclodextrin</span>/polydopamine-coated capillary was validated by the analysis of seven pairs of chiral analytes, namely epinephrine, norepinephrine, isoprenaline, terbutaline, verapamil, tryptophane, carvedilol. Good enantioseparation efficiencies were achieved for all. For three consecutive runs, the relative standard deviations for the migration times of the analytes for intraday, interday, and column-to-column repeatability were in the range of 0.41-1.74, 1.03-4.18, and 1.66-8.24%, respectively. Moreover, the separation efficiency of the β-<span class="hlt">cyclodextrin</span>/polydopamine-coated capillary column did not decrease obviously over 90 runs. The strategy should also be feasible to introduce and immobilize other chiral selectors on the inner walls surface of capillary columns. © 2017 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5295198','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5295198"><span>SERS-Based Flavonoid Detection Using Ethylenediamine-β-<span class="hlt">Cyclodextrin</span> as <span class="hlt">a</span> Capturing Ligand</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Choi, Jae Min; Hahm, Eunil; Park, Kyeonghui; Jeong, Daham; Rho, Won-Yeop; Kim, Jaehi; Jeong, Dae Hong; Lee, Yoon-Sik; Jhang, Sung Ho; Chung, Hyun Jong; Cho, Eunae; Yu, Jae-Hyuk; Jun, Bong-Hyun; Jung, Seunho</p> <p>2017-01-01</p> <p>Ethylenediamine-modified β-<span class="hlt">cyclodextrin</span> (Et-β-CD) was immobilized on aggregated silver nanoparticle (NP)-embedded silica NPs (SiO2@Ag@Et-β-CD NPs) for the effective detection of flavonoids. Silica NPs were used as the template for embedding silver NPs to create hot spots and enhance surface-enhanced Raman scattering (SERS) signals. Et-β-CD was immobilized on Ag NPs to capture flavonoids via host-guest <span class="hlt">inclusion</span> complex formation, as indicated by enhanced ultraviolet absorption spectra. The resulting SiO2@Ag@Et-β-CD NPs were used as the SERS substrate for detecting flavonoids, such as hesperetin, naringenin, quercetin, and luteolin. In particular, luteolin was detected more strongly in the linear range 10−7 to 10−3 M than various organic molecules, namely ethylene glycol, β-estradiol, isopropyl alcohol, naphthalene, and toluene. In addition, the SERS signal for luteolin captured by the SiO2@Ag@Et-β-CD NPs remained even after repeated washing. These results indicated that the SiO2@Ag@Et-β-CD NPs can be used as <span class="hlt">a</span> rapid, sensitive, and selective sensor for flavonoids. PMID:28336842</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2018JMoSt1154..504T','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2018JMoSt1154..504T"><span>Encapsulation of boswellic acid with β- and hydroxypropyl-β-<span class="hlt">cyclodextrin</span>: Synthesis, characterization, in vitro drug release and molecular modelling studies</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Tambe, Amruta; Pandita, Nancy; Kharkar, Prashant; Sahu, Niteshkumar</p> <p>2018-02-01</p> <p>Boswellic acids (BAs) are <span class="hlt">a</span> group of pentacyclic triterpenes present in gum-resin of Boswellia serrata. They are well known for their anti-inflammatory, hypolipidemic, immunomodulatory and anti-tumor activity, but they have poor aqueous solubility and limited bioavailability. In order to enhance their aqueous solubility, <span class="hlt">inclusion</span> complexes of BAs with β-<span class="hlt">cyclodextrin</span> (β-CD) and hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HP-β-CD) were synthesized and their drug release profiles were studied. Molecular associations of β-CD and HP-β-CD with BAs were investigated by phase solubility studies. The stability constants were found to be 380.2 and 145.9 M-1 for BA: β-CD and BA: HP-β-CD <span class="hlt">inclusion</span> complexes, respectively with AN- type curve. BA: β-CD and BA: HP-β-CD <span class="hlt">inclusion</span> complexes were synthesized using kneading (KN), co-precipitation (CP) and solvent evaporation (SE) methods in 1:1 as well as 1:2 ratios. Further these were characterized by Fourier transform infrared (FTIR) spectrophotometry, Powder X-ray Diffraction (P-XRD) and Differential scanning calorimetric (DSC) analysis. FTIR analysis showed shifting of frequencies in complexes as compared to CDs and BAs. P-XRD data obtained for BA: β-CD complexes synthesized by CP and SE methods showed amorphous pattern. Also, DSC analysis showed <span class="hlt">a</span> change in thermal behaviour for synthesized complexes. In vitro drug release studies of BA: β-CD complexes showed enhanced release with 1:2 complexes than 1:1 complexes at pH 1.2 and pH 6.8. Similarly, drug release enhancement was observed more with BA: HP-β-CD complexes in 1:2 ratio than 1:1. To understand the interaction of BAs with CD cavity molecular modelling studies were performed which favored 1:2 complex formation over 1:1 complexes. The study thus highlights that CDs can be used for solubility and dissolution enhancement of BAs.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25216019','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25216019"><span>Capillary electrophoresis separation of peptide diastereomers that contain methionine sulfoxide by dual <span class="hlt">cyclodextrin</span>-crown ether systems.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhu, Qingfu; Heinemann, Stefan H; Schönherr, Roland; Scriba, Gerhard K E</p> <p>2014-12-01</p> <p><span class="hlt">A</span> dual-selector system employing achiral crown ethers in combination with <span class="hlt">cyclodextrins</span> has been developed for the separation of peptide diastereomers that contain methionine sulfoxide. The combinations of the crown ethers 15-crown-5, 18-crown-6, Kryptofix® 21 and Kryptofix® 22 and β-<span class="hlt">cyclodextrin</span>, carboxymethyl-β-<span class="hlt">cyclodextrin</span>, and sulfated β-<span class="hlt">cyclodextrin</span> were screened at pH 2.5 and pH 8.0 using <span class="hlt">a</span> 40/50.2 cm, 50 μm id fused-silica capillary and <span class="hlt">a</span> separation voltage of 25 kV. No diastereomer separation was observed in the sole presence of crown ethers, while only sulfated β-<span class="hlt">cyclodextrin</span> was able to resolve some peptide diastereomers at pH 8.0. Depending on the amino acid sequence of the peptide and the applied <span class="hlt">cyclodextrin</span>, the addition of crown ethers, especially the Krpytofix® diaza-crown ethers, resulted in significantly enhanced chiral recognition. Keeping one selector of the dual system constant, increasing concentrations of the second selector resulted in increased peak resolution and analyte migration time for peptide-crown ether-<span class="hlt">cyclodextrin</span> combinations. The simultaneous diastereomer separation of three structurally related peptides was achieved using the dual selector system. © 2014 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20470252','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20470252"><span>Use of <span class="hlt">cyclodextrins</span> in biotransformation reactions with cell cultures of Morus nigra: biosynthesis of prenylated chalcone isocordoin.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Bolasco, Adriana; Fioravanti, Rossella; Rossi, Francesca; Rossi, Paola; Vitali, Alberto</p> <p>2010-06-16</p> <p>In vivo biotransformation experiments were performed by using <span class="hlt">a</span> cell suspension culture of Morus nigra expressing <span class="hlt">a</span> high PT (prenyltransferase) activity, fed with the target substrate 2',4'-dihydroxychalcone. In order to improve the reaction yields by enhancing the chalcone solubility, three different <span class="hlt">cyclodextrins</span> have been used to host the substrate. The respective complexes have been studied by means of both spectroscopic and calorimetric techniques (Fourier-transform infrared, 1H-NMR and differential scanning calorimetry) and the solution behaviours have been characterized by solubility phase studies. The hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> complex was found to be the most suitable for biotransformation, and the reaction of prenylation resulted in <span class="hlt">a</span> 6-fold higher yield of the final product when compared with the use of the free substrate. The reaction provided as the sole product the 3'-dimethylallyl derivative isocordoin, <span class="hlt">a</span> biologically active plant <span class="hlt">compound</span>. The results obtained allow the development of systems based on the use of biofermentors or the use of immobilized cells in order to enhance the biotransformation yields.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24152895','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24152895"><span><span class="hlt">Cyclodextrin</span> based nanosponges for pharmaceutical use: <span class="hlt">a</span> review.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tejashri, Gursalkar; Amrita, Bajaj; Darshana, Jain</p> <p>2013-09-01</p> <p>Nanosponges are <span class="hlt">a</span> novel class of hyper-crosslinked polymer based colloidal structures consisting of solid nanoparticles with colloidal sizes and nanosized cavities. These nano-sized colloidal carriers have been recently developed and proposed for drug delivery, since their use can solubilize poorly water-soluble drugs and provide prolonged release as well as improve <span class="hlt">a</span> drug's bioavailability by modifying the pharmacokinetic parameters of actives. Development of nanosponges as drug delivery systems, with special reference to <span class="hlt">cyclodextrin</span> based nanosponges, is presented in this article. In the current review, attempts have been made to illustrate the features of <span class="hlt">cyclodextrin</span> based nanosponges and their applications in pharmaceutical formulations. Special emphasis has been placed on discussing the methods of preparation, characterization techniques and applications of these novel drug delivery carriers for therapeutic purposes. Nanosponges can be referred to as solid porous particles having <span class="hlt">a</span> capacity to load drugs and other actives into their nanocavity; they can be formulated as oral, parenteral, topical or inhalation dosage forms. Nanosponges offer high drug loading compared to other nanocarriers and are thus suitable for solving issues related to stability, solubility and delayed release of actives. Controlled release of the loaded actives and solubility enhancement of poorly water-soluble drugs are major advantages of nanosponge drug delivery systems.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2851804','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2851804"><span>Endocytosis of beta-<span class="hlt">cyclodextrins</span> is responsible for cholesterol reduction in Niemann-Pick type C mutant cells</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Rosenbaum, Anton I.; Zhang, Guangtao; Warren, J. David; Maxfield, Frederick R.</p> <p>2010-01-01</p> <p>Niemann-Pick type C disease (NPC) is <span class="hlt">a</span> lysosomal storage disorder causing accumulation of unesterified cholesterol in lysosomal storage organelles. Recent studies have shown that hydroxypropyl-β-<span class="hlt">cyclodextrin</span> injections in npc1−/− mice are partially effective in treating this disease. Using cultured fibroblasts, we have investigated the cellular mechanisms responsible for reduction of cholesterol accumulation. We show that decreased levels of cholesterol accumulation are maintained for several days after removal of <span class="hlt">cyclodextrin</span> from the culture medium. This suggests that endocytosed <span class="hlt">cyclodextrin</span> can reduce the cholesterol storage by acting from inside endocytic organelles rather than by removing cholesterol from the plasma membrane. To test this further, we incubated both NPC1 and NPC2 mutant cells with cholesterol-loaded <span class="hlt">cyclodextrin</span> for 1 h, followed by chase in serum-containing medium. Although the cholesterol content of the treated cells increased after the 1-h incubation, the cholesterol levels in the storage organelles were later reduced significantly. We covalently coupled <span class="hlt">cyclodextrin</span> to fluorescent dextran polymers. These cyclodextrin–dextran conjugates were delivered to cholesterol-enriched lysosomal storage organelles and were effective at reducing the cholesterol accumulation. We demonstrate that methyl-β-<span class="hlt">cyclodextrin</span> is more potent than hydroxypropyl-β-<span class="hlt">cyclodextrin</span> in reducing both cholesterol and bis(monoacylglycerol) phosphate accumulation in NPC mutant fibroblasts. Brief treatment of cells with <span class="hlt">cyclodextrins</span> causes an increase in cholesterol esterification by acyl Co<span class="hlt">A</span>:cholesterol acyl transferase, indicating increased cholesterol delivery to the endoplasmic reticulum. These findings suggest that <span class="hlt">cyclodextrin</span>-mediated enhanced cholesterol transport from the endocytic system can reduce cholesterol accumulation in cells with defects in either NPC1 or NPC2. PMID:20212119</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28840209','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28840209"><span>Complexation induced aggregation and deaggregation of acridine orange with sulfobutylether-β-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sayed, Mhejabeen; Jha, Shruti; Pal, Haridas</p> <p>2017-09-13</p> <p>The present study reports <span class="hlt">a</span> contrasting interaction behaviour of <span class="hlt">a</span> biologically important dye, acridine orange (AOH + ), with <span class="hlt">a</span> highly water soluble anionic host, based on <span class="hlt">a</span> β-<span class="hlt">cyclodextrin</span> (βCD) scaffold, i.e. sulfobutylether-β-<span class="hlt">cyclodextrin</span> (SBEβCD), in comparison to native βCD. AOH + shows striking modulation in its photophysical properties, representing sequential changes in the modes of interaction with increasing SBEβCD concentration. At lower SBEβCD concentrations, AOH + preferentially binds in dimeric forms at the negatively charged SBEβCD portals, leading to strong fluorescence quenching. At higher SBEβCD concentrations, the dimeric dyes convert to monomeric forms and subsequently undergo both <span class="hlt">inclusion</span> and exo complex formation with 1 : 1 stoichiometry, resulting in <span class="hlt">a</span> large fluorescence enhancement. The intriguing observation of sequential fluorescence switch off and switch on for an AOH + -SBEβCD system is clearly facilitated by the presence of butylether chains with SO 3 - end groups at the portals of SBEβCD, providing an additional ion-ion interaction and much enhanced hydrophobic interaction for cationic AOH + compared to the native βCD host. To the best of our knowledge, such fluorescence off/on switching through multistep host-guest binding has not been reported so far in the literature. The present study not only provides <span class="hlt">a</span> detailed insight into the unique binding interactions of AOH + with the SBEβCD host, but the findings of this study are also expected to be useful in designing supramolecular based drug formulations, drug delivery systems, sensors, and so on.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2017JPhCS.824a2016P','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2017JPhCS.824a2016P"><span>Encapsulation of Citronellal from Citronella Oil using β-<span class="hlt">Cyclodextrin</span> and Its Application as Mosquito (Aedes aegypti) Repellent</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Pujiastuti, A.; Cahyono, E.; Sumarni, W.</p> <p>2017-04-01</p> <p>Mosquito (Aedes aegypti) is <span class="hlt">a</span> threat to human health due to its capability to spread dengue fever. Citronellal in citronella oil is one ofnatural active <span class="hlt">compound</span> that has repellent activity. Essential oil is <span class="hlt">a</span> sensitive material whichiseasy to degrade. Encapsulation is coating technology use to avoid essential oil from degradation problems. β-<span class="hlt">Cyclodextrin</span> is frequently used as acoating material in encapsulation. The aims of this study wereto prepare the citronellal encapsulation and to evaluate its control-released and repellency. In this study, encapsulated citronellal was prepared using 83.65% citronellal and encapsulation were prepared with the theemulsion-based method and dried using freeze-dryer. The best-controlled release was performed in citronellal encapsulate with <span class="hlt">a</span> weight ratio of 1:1 (citronellal : β-<span class="hlt">Cyclodextrin</span>). The morphology of encapsulated citronellal was analyzed using SEM. SEM result showed it has three dimensions random shape and agglomerate in some part with thebrighter spot. Citronellal encapsulate showed the highest repellent effect at 84,67% for 5 minutes in mosquito repellency test although it has lower result compared with citronellal inliquid form.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=6011829','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=6011829"><span>An MM and QM Study of Biomimetic Catalysis of Diels-Alder Reactions Using <span class="hlt">Cyclodextrins</span></span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Chen, Wei; Sun, Lipeng; Tang, Zhiye; Ali, Zulfikhar A.; Wong, Bryan M.; Chang, Chia-en A.</p> <p>2018-01-01</p> <p>We performed <span class="hlt">a</span> computational investigation of the mechanism by which <span class="hlt">cyclodextrins</span> (CDs) catalyze Diels-Alder reactions between 9-anthracenemethanol and N-cyclohexylmaleimide. Hydrogen bonds (Hbonds) between N-cyclohexylmaleimide and the hydroxyl groups of <span class="hlt">cyclodextrins</span> were suggested to play an important role in this catalytic process. However, our free energy calculations and molecular dynamics simulations showed that these Hbonds are not stable, and quantum mechanical calculations suggested that the reaction is not promoted by these Hbonds. The binding of 9-anthracenemethanol and N-cyclohexylmaleimide to <span class="hlt">cyclodextrins</span> was the key to the catalytic process. <span class="hlt">Cyclodextrins</span> act as <span class="hlt">a</span> container to hold the two reactants in the cavity, pre-organize them for the reactions, and thus reduce the entropy penalty to the activation free energy. Dimethyl-β-CD was <span class="hlt">a</span> better catalyst for this specific reaction than β-CD because of its stronger van der Waals interaction with the pre-organized reactants and its better performance in reducing the activation energy. This computational work sheds light on the mechanism of the catalytic reaction by <span class="hlt">cyclodextrins</span> and introduces new perspectives of supramolecular catalysis. PMID:29938117</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23665921','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23665921"><span>Synthesis and characterization of thiolated carboxymethyl chitosan-graft-<span class="hlt">cyclodextrin</span> nanoparticles as <span class="hlt">a</span> drug delivery vehicle for albendazole.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Alamdarnejad, Ghazaleh; Sharif, Alireza; Taranejoo, Shahrouz; Janmaleki, Mohsen; Kalaee, Mohammad Reza; Dadgar, Mohsen; Khakpour, Mazyar</p> <p>2013-08-01</p> <p><span class="hlt">A</span> new strategy for the synthesis of thiolated carboxymethyl chitosan-g-<span class="hlt">cyclodextrin</span> nanoparticles by an ionic-gelation method is presented. The synthetic approach was based on the utilization of 1,6-hexamethylene diisocyanate during <span class="hlt">cyclodextrin</span> grafting onto carboxymethyl chitosan. The use of the 1,6-hexamethylene diisocyanate resulted in reactions between <span class="hlt">cyclodextrin</span> and active sites at the C6-position of chitosan, and preserved amino groups of chitosan for subsequent reactions with thioglycolic acid, as the thiolating agent, and tripolyphosphate, as the gelling counterion. Various methods such as scanning electron microscopy, rheology and in vitro release studies were employed to exhibit significant features of the nanoparticles for mucosal albendazole delivery applications. It was found that the thiolated carboxymethyl chitosan-g-<span class="hlt">cyclodextrin</span> nanoparticles prepared using an aqueous solution containing 1 wt% of tripolyphosphate and having 115.65 (μmol/g polymer) of grafted thiol groups show both the highest mucoadhesive properties and the highest albendazole entrapment efficiency. The latter was confirmed theoretically by calculating the enthalpy of mixing of albendazole in the above thiolated chitosan polymer.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/18692338','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/18692338"><span>Water-soluble loratadine <span class="hlt">inclusion</span> complex: analytical control of the preparation by microwave irradiation.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Nacsa, A; Ambrus, R; Berkesi, O; Szabó-Révész, P; Aigner, Z</p> <p>2008-11-04</p> <p>The majority of active pharmaceutical ingredients are poorly soluble in water. The rate-determining step of absorption is the dissolution of these drugs. <span class="hlt">Inclusion</span> complexation with <span class="hlt">cyclodextrin</span> derivatives can lead to improved aqueous solubility and bioavailability of pharmacons due to the formation of co-crystals through hydrogen-bonding between the components. <span class="hlt">Inclusion</span> complexes of loratadine were prepared by <span class="hlt">a</span> convenient new method involving microwave irradiation and the products were compared with those of <span class="hlt">a</span> conventional preparation method. Dissolution studies demonstrated that the solubility and rate of dissolution of loratadine increased in both of the methods used. The interactions between the components were investigated by thermal analysis and Fourier Transform Infrared studies. The microwave treatment did not cause any chemical changes in the loratadine molecule.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29682842','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29682842"><span>Recent Advances in <span class="hlt">Cyclodextrin</span>-Based Light-Responsive Supramolecular Systems.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhang, Xiaojin; Ma, Xin; Wang, Kang; Lin, Shijun; Zhu, Shitai; Dai, Yu; Xia, Fan</p> <p>2018-06-01</p> <p><span class="hlt">Cyclodextrins</span> (CDs), one of the host molecules in supramolecular chemistry, can host guest molecules to form <span class="hlt">inclusion</span> complexes via non-covalent and reversible host-guest interactions. CD-based light-responsive supramolecular systems are typically constructed using CDs and guest molecules with light-responsive moieties, including azobenzene, arylazopyrazole, o-nitrobenzyl ester, pyrenylmethyl ester, coumarin, and anthracene. To date, numerous efforts have been reported on the topic of CD-based light-responsive supramolecular systems, but these have not yet been highlighted in <span class="hlt">a</span> separated review. This review summarizes the efforts reported over the past ten years. The main text of this review is divided into five sections (vesicles, micelles, gels, capturers, and nanovalves) according to the formation of self-assemblies. This feature article aims to afford <span class="hlt">a</span> comprehensive understanding of the light-responsive moieties used in the construction of CD-based light-responsive supramolecular systems and to provide <span class="hlt">a</span> helpful guide for the further design of CD-based light-responsive supramolecular systems. © 2018 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/15000434','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/15000434"><span>Influence of <span class="hlt">cyclodextrin</span> complexation on the in vivo photoprotective effects of oxybenzone.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Felton, Linda A; Wiley, Cody J; Godwin, Donald A</p> <p>2004-01-01</p> <p>The objective of the current study was to investigate the influence of <span class="hlt">cyclodextrin</span> complexation on the in vivo photoprotective effects of <span class="hlt">a</span> model ultraviolet (UV) absorber, oxybenzone, and to compare these novel sunscreens to <span class="hlt">a</span> commercial SPF 30 sunscreen product. Aqueous-based solutions and suspensions containing 2.7 mg/mL oxybenzone and up to 20% (w/w) hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> (HPCD) were prepared. The sunscreens were applied to the dorsal skin of SKH-1 hairless mice and the animals were exposed to up to two minimal erythemal doses (MEDs) of UV radiation. Control animals received no sunscreen treatment. Lipid damage, as quantified by decreases in the lipid melting temperature of the epidermis, was determined using differential scanning calorimetry immediately after UV exposure. The number of sunburn cells (SBCs) and the extent of edema were measured 24 hours postexposure. Results showed that all oxybenzone-containing formulations decreased the number of SBCs formed, diminished swelling, and reduced the physical damage to the skin structure, in comparison to control. Thus, complexation did not prevent oxybenzone from reacting with light. The 20% HPCD formulation exhibited more substantial photoprotection at UV exposures of one or two MEDs, as evidenced by the formation of fewer SBCs. The 5% HPCD formulation also provided substantial protection against epidermal lipid damage. These studies demonstrate that <span class="hlt">inclusion</span> of HPCD in sunscreen formulations may enhance the in vivo photoprotective effects of the UV absorbers. No single HPCD-containing sunscreen, however, was found to be equivalent to <span class="hlt">a</span> commercially available sunscreen product for all biomarkers investigated.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2042808','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2042808"><span>Improved bioavailability and clinical response in patients with chronic liver disease following the administration of <span class="hlt">a</span> spironolactone: β-<span class="hlt">cyclodextrin</span> complex</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Abosehmah-Albidy, A. Z. M.; York, P.; Wong, V.; Losowsky, M. S.; Chrystyn, H.</p> <p>1997-01-01</p> <p>Aims To compare the absorption and clinical effect of spironolactone from an <span class="hlt">inclusion</span> complex with β-<span class="hlt">cyclodextrin</span> (SP-COMP) to Aldactone tablets (ALD) in chronic liver disease. Methods Patients, admitted with chronic liver disease, completed <span class="hlt">a</span> randomized crossover steady state study. They received their spironolactone dose as either daily SP-COMP or ALD for 7 days. Serial blood samples were drawn over <span class="hlt">a</span> 24 h period from day 7 of each therapy. Accurate fluid balance was recorded on days 5–7 and 12–14. Thirteen (six females) whose mean (s.d.) age and weight was 58.4(9.3) years and 74.3(19.0) kg completed the study. Results The mean (95% confidence limits) relative bioavailability for SP-COMP (compared with ALD) from steady state serum concentrations of canrenone, 6β-hydroxyl 7α-thiomethyl spironolactone and 7α-thiomethyl spironolactone was 310.0 (265.4, 336.7), 233.4(212.9, 250.8) and 254.8(230.8, 279.0)%, respectively. Improvements in clinical status and fluid balance occurred over the last 3 days of SP-COMP with <span class="hlt">a</span> mean (s.d.) net loss, in fluid balance, of 1370(860)ml compared with <span class="hlt">a</span> gain of 228(936)ml during ALD. Conclusions Better absorption of spironolactone from the spironolactone: β-<span class="hlt">cyclodextrin</span> complex formulation should lead to <span class="hlt">a</span> reduction in dosage and perhaps <span class="hlt">a</span> more consistent effect in patients with chronic liver disease. PMID:9241094</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28130905','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28130905"><span>Characterization of complexes between phenethylamine enantiomers and β-<span class="hlt">cyclodextrin</span> derivatives by capillary electrophoresis-Determination of binding constants and complex mobilities.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Wahl, Joachim; Furuishi, Takayuki; Yonemochi, Etsuo; Meinel, Lorenz; Holzgrabe, Ulrike</p> <p>2017-04-01</p> <p>To optimize chiral separation conditions and to improve the knowledge of enantioseparation, it is important to know the binding constants K between analytes and <span class="hlt">cyclodextrins</span> and the electrophoretic mobilities of the temporarily formed analyte-<span class="hlt">cyclodextrin</span>-complexes. K values for complexes between eight phenethylamine enantiomers, namely ephedrine, pseudoephedrine, methylephedrine and norephedrine, and four different β-<span class="hlt">cyclodextrin</span> derivatives were determined by affinity capillary electrophoresis. The binding constants were calculated from the electrophoretic mobility values of the phenethylamine enantiomers at increasing concentrations of <span class="hlt">cyclodextrins</span> in running buffer. Three different linear plotting methods (x-reciprocal, y-reciprocal, double reciprocal) and nonlinear regression were used for the determination of binding constants with β-<span class="hlt">cyclodextrin</span>, (2-hydroxypropyl)-β-<span class="hlt">cyclodextrin</span>, methyl-β-<span class="hlt">cyclodextrin</span> and 6-O-α-maltosyl-β-<span class="hlt">cyclodextrin</span>. The <span class="hlt">cyclodextrin</span> concentration in <span class="hlt">a</span> 50 mM phosphate buffer pH 3.0 was varied from 0 to 12 mM. To investigate the influence of the binding constant values on the enantioseparation the observed electrophoretic selectivities were compared with the obtained K values and the calculated enantiomer-<span class="hlt">cyclodextrin</span>-complex mobilities. The different electrophoretic mobilities of the temporarily formed complexes were crucial factors for the migration order and enantioseparation of ephedrine derivatives. To verify the apparent binding constants determined by capillary electrophoresis, <span class="hlt">a</span> titration process using ephedrine enantiomers and β-<span class="hlt">cyclodextrin</span> was carried out. Furthermore, the isothermal titration calorimetry measurements gave information about the thermal properties of the complexes. © 2017 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27185128','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27185128"><span>Determination of the glass transition temperature of <span class="hlt">cyclodextrin</span> polymers.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tabary, Nicolas; Garcia-Fernandez, Maria Jose; Danède, Florence; Descamps, Marc; Martel, Bernard; Willart, Jean-François</p> <p>2016-09-05</p> <p>The aim of this work was to determine the main physical characteristics of β-<span class="hlt">cyclodextrin</span> polymers, well known for improving complexation capacities and providing enhanced and sustained release of <span class="hlt">a</span> large panel of drugs. Two polymers were investigated: <span class="hlt">a</span> polymer of β-<span class="hlt">cyclodextrin</span> (polyβ-CD) and <span class="hlt">a</span> polymer of partially methylated (DS=0.57) β-<span class="hlt">cyclodextrin</span> (polyMe-β-CD). The physical characterizations were performed by powder X-ray diffraction and differential scanning calorimetry. The results indicate that these polymers are amorphous and that their glass transition is located above the thermal degradation point of the materials preventing their direct observation and thus their full characterization. We could however estimate the virtual glass transition temperatures by mixing the polymers with different plasticizers (trehalose and mannitol) which decreases Tg sufficiently to make the glass transition observable. Extrapolation to zero plasticizer concentration then yield the following Tg values: Tg (polyMe-β-CD)=317°C±5°C and Tg (polyβ-CD)=418°C±6°C. Copyright © 2016 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27133126','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27133126"><span>Optimization of <span class="hlt">a</span> method for preparing solid complexes of essential clove oil with β-<span class="hlt">cyclodextrins</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Hernández-Sánchez, Pilar; López-Miranda, Santiago; Guardiola, Lucía; Serrano-Martínez, Ana; Gabaldón, José Antonio; Nuñez-Delicado, Estrella</p> <p>2017-01-01</p> <p>Clove oil (CO) is an aromatic oily liquid used in the food, cosmetics and pharmaceutical industries for its functional properties. However, its disadvantages of pungent taste, volatility, light sensitivity and poor water solubility can be solved by applying microencapsulation or complexation techniques. Essential CO was successfully solubilized in aqueous solution by forming <span class="hlt">inclusion</span> complexes with β-<span class="hlt">cyclodextrins</span> (β-CDs). Moreover, phase solubility studies demonstrated that essential CO also forms insoluble complexes with β-CDs. Based on these results, essential CO-β-CD solid complexes were prepared by the novel approach of microwave irradiation (MWI), followed by three different drying methods: vacuum oven drying (VO), freeze-drying (FD) or spray-drying (SD). FD was the best option for drying the CO-β-CD solid complexes, followed by VO and SD. MWI can be used efficiently to prepare essential CO-β-CD complexes with good yield on an industrial scale. © 2016 Society of Chemical Industry. © 2016 Society of Chemical Industry.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_20");'>20</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li class="active"><span>22</span></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_22 --> <div id="page_23" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li class="active"><span>23</span></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li><a href="#" onclick='return showDiv("page_25");'>25</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="441"> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12541913','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12541913"><span>Method development of enantiomer separations by affinity capillary electrophoresis, <span class="hlt">cyclodextrin</span> electrokinetic chromatography and capillary electrophoresis-mass spectrometry.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Tanaka, Yoshihide</p> <p>2002-07-01</p> <p>Capillary electrophoresis (CE) has become <span class="hlt">a</span> powerful tool for enantiomer separations during the last decade. Since 1993, the author has investigated enantiomer separations by affinity capillary electrophoresis (affinity CE) with some proteins and by <span class="hlt">cyclodextrin</span> electrokinetic chromatography (CDEKC) with some charged <span class="hlt">cyclodextrins</span> (CDs). Many successful enantiomer separations are demonstrated from our study in this review article. In the enantiomer separations by affinity CE, the deterioration of detection sensitivity was observed under high concentration of the protein in running solutions. The partial filling technique was practically useful to solve the serious problem. It allowed operation at high protein concentrations, such as 500 mumol/L, without the detection problem. Charged CDs had several advantages for the enantiomer separations over neutral ones. Strong electrostatic interactions between <span class="hlt">a</span> charged CD and oppositely charged analytes should be effective for the formation of the complex. <span class="hlt">A</span> large difference in electrophoretic mobility between the free analyte and the <span class="hlt">inclusion</span> complex should also enhance the enantiomeric resolution. In CE-mass spectrometry (CE-MS), the partial filling technique was applied to avoid the introduction of nonvolatile chiral selectors into the CE-MS interface. By replacing the nonvolatile electrolytes in the running buffer by volatile ones, the separation conditions employed in CE with the UV detection method could be transferred to CE-MS.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3299942','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3299942"><span>Oxygen radical absorbance capacity (ORAC) of <span class="hlt">cyclodextrin</span>-solubilized flavonoids, resveratrol and astaxanthin as measured with the ORAC-EPR method</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Sueishi, Yoshimi; Ishikawa, Misa; Yoshioka, Daisuke; Endoh, Nobuyuki; Oowada, Shigeru; Shimmei, Masashi; Fujii, Hirotada; Kotake, Yashige</p> <p>2012-01-01</p> <p>Recently, we proposed an oxygen radical absorbance capacity method that directly quantifies the antioxidant’s scavenging capacity against free radicals and evaluated the radical scavenging abilities for water soluble antioxidant <span class="hlt">compounds</span>. In this study, we determined the radical scavenging abilities of lipophilic antioxidants which were solubilized by <span class="hlt">cyclodextrin</span> in water. Commonly employed fluorescence-based method measures the antioxidant’s protection capability for the fluorescent probe, while we directly quantify free-radical level using electron paramagnetic resonance spin trapping technique. In addition, the spin trapping-based method adopted controlled UV-photolysis of azo-initiator for free radical generation, but in fluorescence-based method, thermal decomposition of azo-initiator was utilized. We determined the radical scavenging abilities of seven well-known lipophilic antioxidants (five flavonoids, resveratrol and astaxanthin), using methylated β-<span class="hlt">cyclodextrin</span> as <span class="hlt">a</span> solubilizer. The results indicated that the agreement between spin trapping-based and fluorescence-based values was only fair partly because of <span class="hlt">a</span> large variation in the previous fluorescence-based data. Typical radical scavenging abilities in trolox equivalent unit are: catechin 0.96; epicatechin 0.94; epigallocatechin gallate 1.3; kaempferol 0.37; myricetin 3.2; resveratrol 0.64; and astaxanthin 0.28, indicating that myricetin possesses the highest antioxidant capacity among the <span class="hlt">compounds</span> tested. We sorted out the possible causes of the deviation between the two methods. PMID:22448093</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/22448093','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/22448093"><span>Oxygen radical absorbance capacity (ORAC) of <span class="hlt">cyclodextrin</span>-solubilized flavonoids, resveratrol and astaxanthin as measured with the ORAC-EPR method.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sueishi, Yoshimi; Ishikawa, Misa; Yoshioka, Daisuke; Endoh, Nobuyuki; Oowada, Shigeru; Shimmei, Masashi; Fujii, Hirotada; Kotake, Yashige</p> <p>2012-03-01</p> <p>Recently, we proposed an oxygen radical absorbance capacity method that directly quantifies the antioxidant's scavenging capacity against free radicals and evaluated the radical scavenging abilities for water soluble antioxidant <span class="hlt">compounds</span>. In this study, we determined the radical scavenging abilities of lipophilic antioxidants which were solubilized by <span class="hlt">cyclodextrin</span> in water. Commonly employed fluorescence-based method measures the antioxidant's protection capability for the fluorescent probe, while we directly quantify free-radical level using electron paramagnetic resonance spin trapping technique. In addition, the spin trapping-based method adopted controlled UV-photolysis of azo-initiator for free radical generation, but in fluorescence-based method, thermal decomposition of azo-initiator was utilized. We determined the radical scavenging abilities of seven well-known lipophilic antioxidants (five flavonoids, resveratrol and astaxanthin), using methylated β-<span class="hlt">cyclodextrin</span> as <span class="hlt">a</span> solubilizer. The results indicated that the agreement between spin trapping-based and fluorescence-based values was only fair partly because of <span class="hlt">a</span> large variation in the previous fluorescence-based data. Typical radical scavenging abilities in trolox equivalent unit are: catechin 0.96; epicatechin 0.94; epigallocatechin gallate 1.3; kaempferol 0.37; myricetin 3.2; resveratrol 0.64; and astaxanthin 0.28, indicating that myricetin possesses the highest antioxidant capacity among the <span class="hlt">compounds</span> tested. We sorted out the possible causes of the deviation between the two methods.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3317110','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3317110"><span>Sorption of Ochratoxin <span class="hlt">A</span> from Aqueous Solutions Using β-<span class="hlt">Cyclodextrin</span>-Polyurethane Polymer</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Appell, Michael; Jackson, Michael A.</p> <p>2012-01-01</p> <p>The ability of <span class="hlt">a</span> <span class="hlt">cyclodextrin</span>-polyurethane polymer to remove ochratoxin <span class="hlt">A</span> from aqueous solutions was examined by batch rebinding assays. The results from the aqueous binding studies were fit to two parameter models to gain insight into the interaction of ochratoxin <span class="hlt">A</span> with the nanosponge material. The ochratoxin <span class="hlt">A</span> sorption data fit well to the heterogeneous Freundlich isotherm model. The polymer was less effective at binding ochratoxin <span class="hlt">A</span> in high pH buffer (9.5) under conditions where ochratoxin <span class="hlt">A</span> exists predominantly in the dianionic state. Batch rebinding assays in red wine indicate the polymer is able to remove significant levels of ochratoxin <span class="hlt">A</span> from spiked solutions between 1–10 μg·L−1. These results suggest <span class="hlt">cyclodextrin</span> nanosponge materials are suitable to reduce levels of ochratoxin <span class="hlt">A</span> from spiked aqueous solutions and red wine samples. PMID:22474569</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/22474569','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/22474569"><span>Sorption of ochratoxin <span class="hlt">A</span> from aqueous solutions using β-<span class="hlt">cyclodextrin</span>-polyurethane polymer.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Appell, Michael; Jackson, Michael A</p> <p>2012-02-01</p> <p>The ability of <span class="hlt">a</span> <span class="hlt">cyclodextrin</span>-polyurethane polymer to remove ochratoxin <span class="hlt">A</span> from aqueous solutions was examined by batch rebinding assays. The results from the aqueous binding studies were fit to two parameter models to gain insight into the interaction of ochratoxin <span class="hlt">A</span> with the nanosponge material. The ochratoxin <span class="hlt">A</span> sorption data fit well to the heterogeneous Freundlich isotherm model. The polymer was less effective at binding ochratoxin <span class="hlt">A</span> in high pH buffer (9.5) under conditions where ochratoxin <span class="hlt">A</span> exists predominantly in the dianionic state. Batch rebinding assays in red wine indicate the polymer is able to remove significant levels of ochratoxin <span class="hlt">A</span> from spiked solutions between 1-10 μg·L(-1). These results suggest <span class="hlt">cyclodextrin</span> nanosponge materials are suitable to reduce levels of ochratoxin <span class="hlt">A</span> from spiked aqueous solutions and red wine samples.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://www.ars.usda.gov/research/publications/publication/?seqNo115=296634','TEKTRAN'); return false;" href="http://www.ars.usda.gov/research/publications/publication/?seqNo115=296634"><span>Microwave-assisted synthesis of <span class="hlt">cyclodextrin</span> polyurethanes</span></a></p> <p><a target="_blank" href="https://www.ars.usda.gov/research/publications/find-a-publication/">USDA-ARS?s Scientific Manuscript database</a></p> <p></p> <p></p> <p><span class="hlt">Cyclodextrin</span> (CD) has often been incorporated into polyurethanes in order to facilitate its use in encapsulation or removal of organic species for various applications. In this work <span class="hlt">a</span> microwave-assisted method has been developed to produce polyurethanes consisting of alpha-, ß-, and gamma-CD and thr...</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/9867418','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/9867418"><span>Crystal structure of <span class="hlt">a</span> new alpha-<span class="hlt">cyclodextrin</span> hydrate form. Molecular geometry and packing features: disordered solvent contribution.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Puliti, R; Mattia, C A; Paduano, L</p> <p>1998-08-01</p> <p>The crystallographic study of <span class="hlt">a</span> new hydrated form of alpha-<span class="hlt">cyclodextrin</span> (cyclohexaamylose) is reported. C36H60O30 . 11H2O; space group P2(1)2(1)2(1) with cell constants <span class="hlt">a</span> = 13.839(3), b = 15.398(3), c = 24.209(7) <span class="hlt">A</span>; final discrepancy index R = 0.057 for the 5182 observed reflections and 632 refined parameters. Besides four ordered water molecules placed outside alpha-<span class="hlt">cyclodextrins</span>, the structure shows regions of severely disordered solvent mainly confined in the oligosaccharide cavities. The contribution of the observed disorder has been computed via Fourier inversions of the residual electron density and incorporated into the structure factors in further refinements of the ordered part. The alpha-<span class="hlt">cyclodextrin</span> molecule assumes <span class="hlt">a</span> relaxed round shape stabilised by <span class="hlt">a</span> ring sequence of all the six possible O2 ... O3 intramolecular hydrogen bonds. The four ordered water molecules take part in an extensive network of hydrogen bonds (infinite chains and loops) without modifying the scheme of intramolecular H-bonds or the (-)gauche conformation of O-6-H hydroxyl groups. The structure shows <span class="hlt">a</span> new molecular arrangement, for an "empty" hydrated alpha-<span class="hlt">cyclodextrin</span>, like that "brick-type" observed for alpha-CD in the iodoanilide trihydrate complex crystallising in an isomorphous cell.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12504530','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12504530"><span>Surface effects and desorption of tetracycline supramolecular complex on bovine dentine.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Pataro, A L; Franco, C F; Santos, V R; Cortés, M E; Sinisterra, R D</p> <p>2003-03-01</p> <p>The aim of this in vitro study was to evaluate the antimicrobial activity, the substantivity, and surface effects of the <span class="hlt">inclusion</span> <span class="hlt">compound</span> tetracycline: beta-<span class="hlt">cyclodextrin</span> on bovine roots. The antimicrobial activity was assessed by dentine slabs which had been immersed in the <span class="hlt">inclusion</span> complex in concentrations 8.0%, 4.0%, 2.0%, 1.0%, 0.5% and 0.25% for 5min compared to <span class="hlt">a</span> control of tetracycline hydrochloride. Each slab was tested in <span class="hlt">a</span> broth of overnight culture of Actinobacillus actinomycetemcomitans (Y4-FDC). The <span class="hlt">inclusion</span> complex significantly inhibited the <span class="hlt">A</span>. actinomycetemcomitans (p<0.01) verified at concentrations from 1.0% to 8.0%. The substantivity of tetracycline was evaluated by the measure of desorption from the slabs previously immersed in solution samples and removed at 24h intervals. The tetracycline encapsulated in beta-<span class="hlt">cyclodextrin</span> showed <span class="hlt">a</span> flow rate near to zero order in comparison to free tetracycline. The surface morphology determined by SEM showed <span class="hlt">a</span> more homogeneous and integrated layer with the complex compared to the effect of free tetracycline. We concluded that the root surfaces treated with tetracycline: beta-<span class="hlt">cyclodextrin</span> release lower concentrations of active drug over 5 days at inhibitory concentrations against <span class="hlt">A</span>. actinomycetemcomitans with enhanced disponibility in comparison to tetracycline.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24028613','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24028613"><span>Modified-release ointment with nitroglycerin β-<span class="hlt">cyclodextrin</span> <span class="hlt">inclusion</span> complex for treatment of anal fissures.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Centkowska, Katarzyna; Sznitowska, Malgorzata</p> <p>2013-10-01</p> <p>The aim was to evaluate ointments for local treatment of anal fissures. Nitroglycerin (NTG) was complexed with β-<span class="hlt">cyclodextrin</span> (β-CD) to provide prolonged NTG release, with the intention of decreasing systemic drug absorption and thus reducing side effects. Gels, creams and anhydrous water-emulsifying (AWE) ointment with NTG-CD were compared with preparations containing uncomplexed NTG (diluted with crospovidone, NTG-cP). The in-vitro NTG release and ex-vivo skin absorption were studied. The prolonged-release ointment with the NTG-CD complex was formulated using AWE base or w/o cream (20% water); release of NTG from <span class="hlt">a</span> hydrogel was very fast with both the complexed and uncomplexed forms. From the AWE ointment base, 16.4% or 4.5% of the total NTG dose was released after 6 h when NTG-cP or NTG-CD was incorporated, respectively. With the complexed form, NTG absorption to the skin after <span class="hlt">a</span> 5-h application was 18.1 or 11.1 μg/g from AWE ointment or cream, respectively; absorption of the uncomplexed NTG was higher: 52.3 or 21.9 μg/g from AWE ointment and cream, respectively. Complexation with β-CD results in prolonged release of NTG from AWE ointment and w/o cream, which was confirmed by the ex-vivo skin absorption results. © 2013 Royal Pharmaceutical Society.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25582483','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25582483"><span>Quality by design in the chiral separation strategy for the determination of enantiomeric impurities: development of <span class="hlt">a</span> capillary electrophoresis method based on dual <span class="hlt">cyclodextrin</span> systems for the analysis of levosulpiride.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Orlandini, S; Pasquini, B; Del Bubba, M; Pinzauti, S; Furlanetto, S</p> <p>2015-02-06</p> <p>Quality by design (QbD) concepts, in accordance with International Conference on Harmonisation Pharmaceutical Development guideline Q8(R2), represent an innovative strategy for the development of analytical methods. In this paper QbD principles have been comprehensively applied in the set-up of <span class="hlt">a</span> capillary electrophoresis method aimed to quantify enantiomeric impurities. The test <span class="hlt">compound</span> was the chiral drug substance levosulpiride (S-SUL) and the developed method was intended to be used for routine analysis of the pharmaceutical product. The target of analytical QbD approach is to establish <span class="hlt">a</span> design space (DS) of critical process parameters (CPPs) where the critical quality attributes (CQAs) of the method have been assured to fulfil the desired requirements with <span class="hlt">a</span> selected probability. QbD can improve the understanding of the enantioseparation process, including both the electrophoretic behavior of enantiomers and their separation, therefore enabling its control. The CQAs were represented by enantioresolution and analysis time. The scouting phase made it possible to select <span class="hlt">a</span> separation system made by sulfated-β-<span class="hlt">cyclodextrin</span> and <span class="hlt">a</span> neutral <span class="hlt">cyclodextrin</span>, operating in reverse polarity mode. The type of neutral <span class="hlt">cyclodextrin</span> was included among other CPPs, both instrumental and related to background electrolyte composition, which were evaluated in <span class="hlt">a</span> screening phase by an asymmetric screening matrix. Response surface methodology was carried out by <span class="hlt">a</span> Doehlert design and allowed the contour plots to be drawn, highlighting significant interactions between some of the CPPs. DS was defined by applying Monte-Carlo simulations, and corresponded to the following intervals: sulfated-β-<span class="hlt">cyclodextrin</span> concentration, 9-12 mM; methyl-β-<span class="hlt">cyclodextrin</span> concentration, 29-38 mM; Britton-Robinson buffer pH, 3.24-3.50; voltage, 12-14 kV. Robustness of the method was examined by <span class="hlt">a</span> Plackett-Burman matrix and the obtained results, together with system repeatability data, led to define <span class="hlt">a</span> method</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29886278','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29886278"><span>Exploring the oxidation and iron binding profile of <span class="hlt">a</span> <span class="hlt">cyclodextrin</span> encapsulated quercetin complex unveiled <span class="hlt">a</span> controlled complex dissociation through <span class="hlt">a</span> chemical stimulus.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Diamantis, Dimitrios A; Ramesova, Sarka; Chatzigiannis, Christos M; Degano, Ilaria; Gerogianni, Paraskevi S; Karadima, Constantina; Perikleous, Sonia; Rekkas, Dimitrios; Gerothanassis, Ioannis P; Galaris, Dimitrios; Mavromoustakos, Thomas; Valsami, Georgia; Sokolova, Romana; Tzakos, Andreas G</p> <p>2018-06-07</p> <p>Flavonoids possess <span class="hlt">a</span> rich polypharmacological profile and their biological role is linked to their oxidation state protecting DNA from oxidative stress damage. However, their bioavailability is hampered due to their poor aqueous solubility. This can be surpassed through encapsulation to supramolecular carriers as <span class="hlt">cyclodextrin</span> (CD). <span class="hlt">A</span> quercetin- 2HP-β-CD complex has been formerly reported by us. However, once the flavonoid is in its 2HP-β-CD encapsulated state its oxidation potential, its decomplexation mechanism, its potential to protect DNA damage from oxidative stress remained elusive. To unveil this, an array of biophysical techniques was used. The quercetin-2HP-β-CD complex was evaluated through solubility and dissolution experiments, electrochemical and spectroelectrochemical studies (Cyclic Voltammetry) UV-Vis spectroscopy, HPLC-ESI-MS/MS and HPLC-DAD, fluorescence spectroscopy, NMR Spectroscopy, theoretical calculations (density functional theory (DFT)) and biological evaluation of the protection offered against H 2 O 2 -induced DNA damage. Encapsulation of quercetin inside the supramolecule's cavity enhanced its solubility and oxidation profile is retained in its encapsulated state. Although the protective ability of the quercetin-2HP-β-CD complex against H 2 O 2 was diminished, iron serves as <span class="hlt">a</span> chemical stimulus to dissociate the complex and release quercetin. We found that in <span class="hlt">a</span> quercetin-2HP-β-CD <span class="hlt">inclusion</span> complex quercetin retains its oxidation profile similarly to its native state, while iron can operate as <span class="hlt">a</span> chemical stimulus to release quercetin from its host cavity. The oxidation profile of <span class="hlt">a</span> natural product once it is encapsulated in <span class="hlt">a</span> supramolecular <span class="hlt">cyclodextrin</span> carrier as also it was discovered that decomplexation can be triggered by <span class="hlt">a</span> chemical stimulus. Copyright © 2018. Published by Elsevier B.V.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/17441106','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/17441106"><span>Synthesis of anatase TiO2 nanoparticles with beta-<span class="hlt">cyclodextrin</span> as <span class="hlt">a</span> supramolecular shell.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Li, Landong; Sun, Xiaohong; Yang, Yali; Guan, Naijia; Zhang, Fuxiang</p> <p>2006-11-20</p> <p>We report <span class="hlt">a</span> novel, green hydrothermal-synthesis route to well-dispersed anatase TiO2 nanoparticles with particle sizes of 9-16 nm in the presence of beta-CD (beta-<span class="hlt">cyclodextrin</span>). During the synthesis process, the CD-containing synthesis mixture assembled in both longitudinal and latitudinal directions. Driven by the interaction between molecules, the beta-CDs assembled in the longitudinal direction to form long-chain <span class="hlt">compounds</span>, whereas in the latitudinal direction, they tended to form regular aggregates through coordination with the Ti species from the hydrolysis of tetrabutyl titanate. In view of the effect of the coordination and the steric hindrance of beta-CDs as <span class="hlt">a</span> supramolecular shell, homogeneous nuclei and slow growth of TiO2 crystals during the synthesis process was observed, which was responsible for the formation of uniform TiO2 nanoparticles. The low beta-CD dosage and the high product yield (>90%) demonstrated well the potential of this synthesis route in the large-scale industrial production of anatase nanoparticles.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/19157122','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/19157122"><span>[Preparation of coated tablets of glycyrrhetic acid-HP-beta-<span class="hlt">cyclodextrin</span> tablets for colon-specific release].</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Cui, Qi-Hua; Cui, Jing-Hao; Zhang, Jin-Jin</p> <p>2008-10-01</p> <p>To prepare coated tablets of glycyrrhetinic acid and hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> (GTA-HP-beta-CYD) <span class="hlt">inclusion</span> complex tablets for colon-specific release. In order to improve the solubility of GTA, the GTA-HP-beta-CYD <span class="hlt">inclusion</span> complex was prepared by ultrasonic-lyophilization technique and its formation were characterized by X-ray powder diffraction profiles and infrared spectrometry. The effects of <span class="hlt">inclusion</span> condition on the <span class="hlt">inclusion</span> efficiency and stability coefficient of <span class="hlt">inclusion</span> complex were investigated, respectively. After prepared GTA-HP-beta-CYD tablets by powder direct compression, the pH dependant polymer Eudragit III and/or mixed with Eudragit II were used for further coating materials in fluid-bed coater. The influences of coating weight on the GTA release in different pH conditions were evaluated to establish the method for prepering colon specific delivery tablets with pulsed release properties. The formation of <span class="hlt">inclusion</span> complexes were proved by X-ray powder diffraction profile and phase solubility curve. The effect of pH value of solvent was played critical role on the preparation of GTA- HP-beta-CYD <span class="hlt">inclusion</span> complex. And the <span class="hlt">inclusion</span> efficiency of GTA was 9. 3% and the solubility was increased to 54. 6 times at optimized method. The Eudragit III coated GTA- HP-beta-CYD tablets with coating weight 10% and 16% were showed pH dependant colon specific release profiles with slow release rate. The release profile of tablets coated with the mixture of Eudragit II and Eudragit III (1:2) were indicated typical pH dependant colon specific and pulsed release properties while the coating weight was 17%. The preliminary method for preparation of colon specific release tablets containing glycyrrhetinic acid with improved solubility was established for further in vivo therapeutic experiment.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12052695','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12052695"><span>Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-beta-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Charoenchaitrakool, M; Dehghani, F; Foster, N R</p> <p>2002-06-04</p> <p>The dissolution rate of <span class="hlt">a</span> drug into the biological environment can be enhanced by forming complexes with <span class="hlt">cyclodextrins</span> and their derivatives. In this study, ibuprofen-methyl-beta-<span class="hlt">cyclodextrin</span> complexes were prepared successfully by passing ibuprofen-laden CO(2) through <span class="hlt">a</span> methyl-beta-<span class="hlt">cyclodextrin</span> packed bed. The maximum drug loading obtained in this work was 10.8 wt.%, which was comparable to that of <span class="hlt">a</span> 1:1 complex (13.6 wt.% of ibuprofen). The complex exhibited instantaneous dissolution profiles in water solution. The enhanced dissolution rate was attributed to the amorphous character and improved wettability of the product.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27918300','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27918300"><span>Three polymorphs of an <span class="hlt">inclusion</span> <span class="hlt">compound</span> of 2,2'-(disulfanediyl)dibenzoic acid and trimethylamine.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Yang, Yunxia; Li, Lihua; Zhang, Li; Dong, Wenjing; Ding, Keying</p> <p>2016-12-01</p> <p>Polymorphism is the ability of <span class="hlt">a</span> solid material to exist in more than one form or crystal structure and this is of interest in the fields of crystal engineering and solid-state chemistry. 2,2'-(Disulfanediyl)dibenzoic acid (also called 2,2'-dithiosalicylic acid, DTSA) is able to form different hydrogen bonds using its carboxyl groups. The central bridging S atoms allow the two terminal arene rings to rotate freely to generate various hydrogen-bonded linking modes. DTSA can act as <span class="hlt">a</span> potential host molecule with suitable guest molecules to develop new <span class="hlt">inclusion</span> <span class="hlt">compounds</span>. We report here the crystal structures of three new polymorphs of the <span class="hlt">inclusion</span> <span class="hlt">compound</span> of DTSA and trimethylamine, namely trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate 2,2'-(disulfanediyl)dibenzoic acid monosolvate, C 3 H 10 N + ·C 14 H 9 O 4 S 2 - ·C 14 H 10 O 4 S 2 , (1), tetrakis(trimethylazanium) bis{2-[(2-carboxyphenyl)disulfanyl]benzoate} 2,2'-(disulfanediyl)dibenzoate 2,2'-(disulfanediyl)dibenzoic acid monosolvate, 4C 3 H 10 N + ·2C 14 H 9 O 4 S 2 - ·C 14 H 8 O 4 S 2 2- ·C 14 H 10 O 4 S 2 , (2), and trimethylazanium 2-[(2-carboxyphenyl)disulfanyl]benzoate, C 3 H 10 N + ·C 14 H 9 O 4 S 2 - , (3). In the three polymorphs, DTSA utilizes its carboxyl groups to form conventional O-H...O hydrogen bonds to generate different host lattices. The central N atoms of the guest amine molecules accept H atoms from DTSA molecules to give the corresponding cations, which act as counter-ions to produce the stable crystal structures via N-H...O hydrogen bonding between the host acid and the guest molecule. It is noticeable that although these three <span class="hlt">compounds</span> are composed of the same components, the final crystal structures are totally different due to the various configurations of the host acid, the number of guest molecules and the inducer (i.e. ancillary experimental acid).</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23627717','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23627717"><span>Modeling of multiple equilibria in the self-aggregation of di-n-decyldimethylammonium chloride/octaethylene glycol monododecyl ether/<span class="hlt">cyclodextrin</span> ternary systems.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Leclercq, Loïc; Lubart, Quentin; Aubry, Jean-Marie; Nardello-Rataj, Véronique</p> <p>2013-05-28</p> <p>The surface tension equations of binary surfactant mixtures (di-n-decyldimethylammonium chloride and octaethylene glycol monododecyl ether) are established by combining the Szyszkowski equation of surfactant solutions, the ideal or nonideal mixing theory, and the phase separation model. For surfactant mixtures, the surface tension at the air-water interface is calculated using nonideal theory due to synergism between the two adsorbed surfactant types. The incorporation of <span class="hlt">cyclodextrin</span> complexation model to the surface tension equations gives <span class="hlt">a</span> robust model for the description of the surface tension isotherms of binary, ternary, and more complex systems involving numerous <span class="hlt">inclusion</span> complexes. The surface tension data obtained experimentally shows excellent agreement with the theoretical model below and above the formation of micelles. The strong synergistic effect observed between the two surfactants is disrupted by the presence of CDs, leading to ideal behavior of ternary systems. Indeed, depending on the nature of the <span class="hlt">cyclodextrin</span> (i.e., α, β, or γ), which allows <span class="hlt">a</span> tuning of the cavity size, the binding constants with the surfactants are modified as well as the surface properties due to strong modification of equilibria involved in the ternary mixture.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24641510','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24641510"><span>Nanosilica sol leads to further increase in polyethylene glycol (PEG) 1000-enhanced thermostability of β-<span class="hlt">cyclodextrin</span> glycosyltransferase from Bacillus circulans.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Li, Caiming; Huang, Min; Gu, Zhengbiao; Hong, Yan; Cheng, Li; Li, Zhaofeng</p> <p>2014-04-02</p> <p><span class="hlt">A</span> major disadvantage of <span class="hlt">cyclodextrin</span> production is the limited thermostability of <span class="hlt">cyclodextrin</span> glycosyltransferase. The ability of combinations of nanosilica sol with polyethylene glycol (PEG) 1000 to enhance the thermostability of the β-<span class="hlt">cyclodextrin</span> glycosyltransferase from Bacillus circulans was investigated. It was found that 10% PEG 1000 combined with 0.05% nanosilica sol could activate the β-<span class="hlt">cyclodextrin</span> glycosyltransferase by 17.2%. Furthermore, 0.05% nanosilica sol leads to further increase in PEG 1000-enhanced thermostability of β-<span class="hlt">cyclodextrin</span> glycosyltransferase. With the simultaneous addition of 10% PEG 1000 and 0.05% nanosilica into the enzyme solution, which was allowed to incubate for 60 min at 60 °C, 61.3% of β-<span class="hlt">cyclodextrin</span>-forming activity could be retained, which was much higher than that with only 10% PEG 1000 added. Atomic force microscopy, fluorescence spectroscopy, and circular dichroism analysis indicated that silica nanoparticles helped PEG 1000 further protect the tertiary and secondary structures of β-<span class="hlt">cyclodextrin</span> glycosyltransferase. This study provides an effective approach for improving the thermostability of <span class="hlt">cyclodextrin</span> glycosyltransferase and related enzymes.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12637096','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12637096"><span>Complex formation of sericoside with hydrophilic <span class="hlt">cyclodextrins</span>: improvement of solubility and skin penetration in topical emulsion based formulations.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Rode, T; Frauen, M; Müller, B W; Düsing, H J; Schönrock, U; Mundt, C; Wenck, H</p> <p>2003-03-01</p> <p>The main objective of this study was to devise novel methods for improving the solubility of the anti-inflammatory triterpenoid sericoside, the main component of Terminalia sericea extract, thus enabling its incorporation into topical formulations. Sericoside was stabilized by complex formation with hydrophilic derivatives of beta- and gamma-<span class="hlt">cyclodextrins</span> in <span class="hlt">a</span> molar ratio of 1.0:1.1. The complex of extract and <span class="hlt">cyclodextrin</span> was equilibrated in water at 25 degrees C for approximately 24 h. The dehydrated complexes of T. sericea extract and <span class="hlt">cyclodextrin</span> were characterized by differential scanning calorimetry, thermogravimetry analysis and X-ray diffraction. Complex formation with beta-<span class="hlt">cyclodextrin</span> as well as gamma-<span class="hlt">cyclodextrin</span> derivatives was detectable using these three analytical tools; however, only complexes with gamma-<span class="hlt">cyclodextrin</span> derivatives showed stability upon storage after incorporation into topical o/w or w/o formulations. Furthermore, <span class="hlt">a</span> T. sericea extract/gamma-<span class="hlt">cyclodextrin</span> complex incorporated in an o/w formulation resulted in <span class="hlt">a</span> 2.6-fold higher percutaneous penetration of sericoside in in vitro excised pig skin as compared to pure T. sericea extract. For the first time, the virtually insoluble anti-inflammatory active sericoside was incorporated into <span class="hlt">a</span> topical emulsion based formulation in <span class="hlt">a</span> stable manner, resulting in efficient skin penetration. Copyright 2003 Elsevier Science B.V.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29635682','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29635682"><span>Hydroxypropyl-β-<span class="hlt">cyclodextrin</span>-containing hydrogel enhances skin formononetin permeation/retention.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Dias, Paula Hollweg; Scopel, Marina; Martiny, Simony; Bianchi, Sara Elis; Bassani, Valquiria Linck; Zuanazzi, José Angelo Silveira</p> <p>2018-04-10</p> <p>This study was aimed to investigate the in vitro permeation potential of hydrogel formulations containing the isoflavones formononetin and biochanin <span class="hlt">A</span> and <span class="hlt">cyclodextrins</span> in different combinations. The permeation assay was performed using porcine skin discs on Franz diffusion cells model. The isoflavone contents of the formulations were quantified in the different layers of the skin using <span class="hlt">a</span> validated HPLC-PDA method. The isoflavones individually incorporated into the formulations showed high permeation potential, especially formononetin, after the incorporation of hydroxypropyl-β-<span class="hlt">cyclodextrin</span> that enhanced its permeation in the epidermis and dermis. Biochanin <span class="hlt">A</span> showed 2.7 times of permeation capacity in the epidermis and dermis mainly after incorporation of <span class="hlt">cyclodextrins</span> in the formulations. Formononetin showed reduction in its permeation when incorporated in the formulations together to biochanin <span class="hlt">A</span>, showing the absence of synergism. Our results indicated <span class="hlt">a</span> noticeable skin permeation promoting effect of HPβCD in formononetin formulation. Furthermore, formononetin and biochanin <span class="hlt">A</span> can permeate the skin being mostly retained in the epidermis and dermis, revealing its potential use in cosmetic preparations intended to prevent skin aging. © 2018 Royal Pharmaceutical Society.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23492812','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23492812"><span>Polybrominated dibenzo-p-dioxins, dibenzofurans, and biphenyls: <span class="hlt">inclusion</span> in the toxicity equivalency factor concept for dioxin-like <span class="hlt">compounds</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>van den Berg, Martin; Denison, Michael S; Birnbaum, Linda S; Devito, Michael J; Fiedler, Heidelore; Falandysz, Jerzy; Rose, Martin; Schrenk, Dieter; Safe, Stephen; Tohyama, Chiharu; Tritscher, Angelika; Tysklind, Mats; Peterson, Richard E</p> <p>2013-06-01</p> <p>In 2011, <span class="hlt">a</span> joint World Health Organization (WHO) and United Nations Environment Programme (UNEP) expert consultation took place, during which the possible <span class="hlt">inclusion</span> of brominated analogues of the dioxin-like <span class="hlt">compounds</span> in the WHO Toxicity Equivalency Factor (TEF) scheme was evaluated. The expert panel concluded that polybrominated dibenzo-p-dioxins (PBDDs), dibenzofurans (PBDFs), and some dioxin-like biphenyls (dl-PBBs) may contribute significantly in daily human background exposure to the total dioxin toxic equivalencies (TEQs). These <span class="hlt">compounds</span> are also commonly found in the aquatic environment. Available data for fish toxicity were evaluated for possible <span class="hlt">inclusion</span> in the WHO-UNEP TEF scheme (van den Berg et al., 1998). Because of the limited database, it was decided not to derive specific WHO-UNEP TEFs for fish, but for ecotoxicological risk assessment, the use of specific relative effect potencies (REPs) from fish embryo assays is recommended. Based on the limited mammalian REP database for these brominated <span class="hlt">compounds</span>, it was concluded that sufficient differentiation from the present TEF values of the chlorinated analogues (van den Berg et al., 2006) was not possible. However, the REPs for PBDDs, PBDFs, and non-ortho dl-PBBs in mammals closely follow those of the chlorinated analogues, at least within one order of magnitude. Therefore, the use of similar interim TEF values for brominated and chlorinated congeners for human risk assessment is recommended, pending more detailed information in the future.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li class="active"><span>23</span></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li><a href="#" onclick='return showDiv("page_25");'>25</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_23 --> <div id="page_24" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li class="active"><span>24</span></li> <li><a href="#" onclick='return showDiv("page_25");'>25</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="461"> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27265242','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27265242"><span>Effects of propolis and gamma-<span class="hlt">cyclodextrin</span> on intestinal neoplasia in normal weight and obese mice.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Cho, Youngjin; Gutierrez, Linda; Bordonaro, Michael; Russo, Daniel; Anzelmi, Frank; Hooven, Jayde T; Cerra, Carmine; Lazarova, Darina L</p> <p>2016-09-01</p> <p>Obesity is associated with colorectal cancer (CRC). This effect might be attributed to adipokine-supported signaling. We have established that propolis suppresses survival signaling in CRC cells in vitro; therefore, we ascertained the ability of <span class="hlt">a</span> propolis supplement to modulate intestinal neoplastic development in C57BL/6J-ApcMin/+/J mice in the lean and obese state. To induce obesity, mice were fed with <span class="hlt">a</span> Western diet containing 40% fat. Since the propolis supplement includes gamma-<span class="hlt">cyclodextrin</span>, the interventions included diets supplemented with or without gamma-<span class="hlt">cyclodextrin</span>. The animals were administered the following diets: (1) control diet, (2) control diet/gamma-<span class="hlt">cyclodextrin</span>, (3) control diet/propolis, (4) Western diet, (5) Western diet/gamma-<span class="hlt">cyclodextrin</span>, and (6) Western diet/propolis. Western diet, resulting in obesity, accelerated neoplastic progression, as evidenced by the larger size and higher grade dysplasia of the neoplasms. In the context of normal weight, gamma-<span class="hlt">cyclodextrin</span> and propolis affected neoplastic progression, as determined by the size of the lesions and their grade of dysplasia. <span class="hlt">A</span> statistically significant decrease in the number of adenomas was detected in mice fed <span class="hlt">a</span> control diet with the propolis supplement (61.8 ± 10.6 vs. 35.3 ± 7.6, P = 0.008). Although there was no significant difference in the polyp numbers between the six groups, the mice with the lowest number and size of adenomas were those fed <span class="hlt">a</span> Western diet with gamma-<span class="hlt">cyclodextrin</span>. This unexpected outcome might be explained by the increased levels of apoptosis detected in the intestinal tissues of these obese mice. We posit that butyrate derived from the metabolism of gamma-<span class="hlt">cyclodextrin</span> may contribute to the decreased neoplastic burden in the context of obesity; however, future studies are required to address this possibility. © 2016 The Authors. Cancer Medicine published by John Wiley & Sons Ltd.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2003AcSpA..59..909M','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2003AcSpA..59..909M"><span>Spectrofluorimetric study of host-guest complexation of ibuprofen with β-<span class="hlt">cyclodextrin</span> and its analytical application</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Manzoori, Jamshid L.; Amjadi, Mohammad</p> <p>2003-03-01</p> <p>The characteristics of host-guest complexation between β-<span class="hlt">cyclodextrin</span> (β-CD) and two forms of ibuprofen (protonated and deprotonated) were investigated by fluorescence spectrometry. 1:1 stoichiometries for both complexes were established and their association constants at different temperatures were calculated by applying <span class="hlt">a</span> non-linear regression method to the change in the fluorescence of ibuprofen that brought about by the presence of β-CD. The thermodynamic parameters (Δ H, Δ S and Δ G) associated with the <span class="hlt">inclusion</span> process were also determined. Based on the obtained results, <span class="hlt">a</span> sensitive spectrofluorimetric method for the determination of ibuprofen was developed with <span class="hlt">a</span> linear range of 0.1-2 μg ml -1 and <span class="hlt">a</span> detection limit of 0.03 μg ml -1. The method was applied satisfactorily to the determination of ibuprofen in pharmaceutical preparations.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26697780','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26697780"><span><span class="hlt">Cyclodextrin</span> based ternary system of modafinil: Effect of trimethyl chitosan and polyvinylpyrrolidone as complexing agents.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Patel, Parth; Agrawal, Y K; Sarvaiya, Jayrajsinh</p> <p>2016-03-01</p> <p>Modafinil is an approved drug for the treatment of narcolepsy and have <span class="hlt">a</span> strong market presence in many countries. The drug is widely consumed for off-label uses and currently listed as <span class="hlt">a</span> restricted drug. Modafinil has very low water solubility. To enhance the aqueous solubility of modafinil by the formation of <span class="hlt">a</span> ternary complex with Hydroxypropyl-β-<span class="hlt">cyclodextrin</span> and two hydrophilic polymers was the main objective of the present study. Pyrrolidone (PVP K30) and <span class="hlt">a</span> water soluble chitosan derivative, trimethyl chitosan (TMC) were studied by solution state and solid state characterization methods for their discriminatory efficiency in solubility enhancement of modafinil. Phase solubility study depicted the highest complexation efficiency (2.22) of <span class="hlt">cyclodextrin</span> derivative in the presence of TMC compared to the same in the presence of PVP K30 (0.08) and in the absence of any polymer (0.92). FT-IR analysis of binary and ternary complex expressed comparable contribution of both polymers in formation of <span class="hlt">inclusion</span> complex. The thermal behaviour of binary and ternary complex, involving individual polymers disclosed the influence of TMC on polymorphism of the drug. DSC study revealed efficiency of TMC to prevent conversion of metastable polymorphic form to stable polymorphic form. Ternary complex, involving TMC enhanced water solubility of the drug 1.5 times more compared to the binary complex of the drug whereas PVP K30 reduced the Solubility. Copyright © 2015 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://www.ars.usda.gov/research/publications/publication/?seqNo115=269407','TEKTRAN'); return false;" href="http://www.ars.usda.gov/research/publications/publication/?seqNo115=269407"><span>Sorption of Ochratoxin <span class="hlt">A</span> from aqueous solutions using beta-<span class="hlt">cyclodextrin</span>-polyurethane polymer</span></a></p> <p><a target="_blank" href="https://www.ars.usda.gov/research/publications/find-a-publication/">USDA-ARS?s Scientific Manuscript database</a></p> <p></p> <p></p> <p>The ability of <span class="hlt">a</span> <span class="hlt">cyclodextrin</span>-polyurethane polymer to remove ochratoxin <span class="hlt">A</span> from aqueous solutions, including wine, was examined by batch rebinding assays and equilibrium sorption isotherms. The results were fit to two parameter models. Freundlich analysis of the sorption isotherm indicates the polyme...</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/21651431','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/21651431"><span><span class="hlt">A</span> comprehensive evaluation of the toxicology of cigarette ingredients: aliphatic carbonyl <span class="hlt">compounds</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Coggins, Christopher R E; Jerome, Ann M; Edmiston, Jeffery S; Oldham, Michael J</p> <p>2011-06-01</p> <p>Aliphatic carbonyl <span class="hlt">compounds</span> are used as ingredients in cigarette tobacco or cigarette filters. <span class="hlt">A</span> battery of tests was used to compare toxicity of mainstream smoke from experimental cigarettes containing 15 aliphatic carbonyl <span class="hlt">compounds</span> that were added individually to experimental cigarettes at three different levels. Smoke from experimental and control cigarettes were evaluated using analytical chemistry, in vitro cytotoxicity (neutral red uptake), and mutagenicity (five bacterial strains) studies. For one <span class="hlt">compound</span>, glycerol triacetate (GTA), two 90-day inhalation studies were also performed, using different <span class="hlt">inclusion</span> levels into either tobacco or cigarette filter. Several smoke constituent concentrations were reduced with the highest <span class="hlt">inclusion</span> level of GTA in tobacco; incorporation of GTA into the filter, and the other <span class="hlt">compounds</span> into tobacco, produced effectively no changes. Cytotoxicity was reduced by the highest <span class="hlt">inclusion</span> of GTA into tobacco for both gas-vapor and particulate phases of smoke; incorporation of GTA into the filter, and the other <span class="hlt">compounds</span> into tobacco, showed no changes. Mutagenicity was reduced by the middle and high <span class="hlt">inclusion</span> levels of GTA into tobacco (TA1537 strain with S9); incorporation of GTA into the filter, and the other <span class="hlt">compounds</span> into tobacco, showed no changes. <span class="hlt">Inclusion</span> of GTA in tobacco at 100,000 ppm reduced the biological effects of the smoke in the various test systems reported in this study, although <span class="hlt">inclusion</span> into the filter did not appear to have any major effect on the endpoints studied. The other 14 aliphatic carbonyl <span class="hlt">compounds</span> that were tested lacked <span class="hlt">a</span> toxicological response.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26187193','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26187193"><span>Interaction of polyphenol oxidase of Solanum tuberosum with β-<span class="hlt">cyclodextrin</span>: Process details and applications.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Singh, Virendra; Jadhav, Swati B; Singhal, Rekha S</p> <p>2015-09-01</p> <p>Polysaccharides differing in structure and chemical nature were screened for their ability to bind non-covalently with polyphenol oxidase (PPO) from potato (as <span class="hlt">a</span> model) and their effect on enzyme activity. All the polysaccharides selected inhibited the PPO but β-<span class="hlt">cyclodextrin</span> showed maximum inhibition under optimum conditions. Process details for the inhibition of PPO were studied with respect to concentration of β-<span class="hlt">cyclodextrin</span>, temperature, pH, and time. Higher inhibition constant and lower half life was obtained at 40 °C than at 30 °C in the presence of inhibitor. β-<span class="hlt">Cyclodextrin</span> showed mixed type of inhibition of PPO. β-<span class="hlt">Cyclodextrin</span> was further exploited as anti-browning agent in selected fruit juices. It not only showed <span class="hlt">a</span> significant anti-browning effect on freshly prepared potato juice but was also effective in other fruit juices. Better effect was seen in pineapple, apple and pear as compared to banana, sugarcane and guava fruit juices. Copyright © 2015 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26471667','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26471667"><span>Interaction of cinnamic acid derivatives with β-<span class="hlt">cyclodextrin</span> in water: experimental and molecular modeling studies.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Liu, Benguo; Zeng, Jie; Chen, Chen; Liu, Yonglan; Ma, Hanjun; Mo, Haizhen; Liang, Guizhao</p> <p>2016-03-01</p> <p><span class="hlt">Cyclodextrins</span> (CDs) can be used to improve the solubility and stability of cinnamic acid derivatives (CAs). However, there was no detailed report about understanding the effects of the substituent groups in the benzene ring on the <span class="hlt">inclusion</span> behavior between CAs and CDs in aqueous solution. Here, the interaction of β-CD with CAs, including caffeic acid, ferulic acid, and p-coumaric acid, in water was investigated by phase-solubility method, UV, fluorescence, and (1)H NMR spectroscopy, together with ONIOM (our Own N-layer Integrated Orbital molecular Mechanics)-based QM/MM (Quantum Mechanics/Molecular Mechanics) calculations. Experimental results demonstrated that CAs could form 1:1 stoichiometric <span class="hlt">inclusion</span> complex with β-CD by non-covalent bonds, and that the maximum apparent stability constants were found in caffeic acid (176M(-1)) followed by p-coumaric acid (160M(-1)) and ferulic acid (133M(-1)). Moreover, our calculations reasonably illustrated the binding orientations of β-CD with CAs determined by experimental observations. Copyright © 2015. Published by Elsevier Ltd.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4878149','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=4878149"><span><span class="hlt">Cyclodextrin</span> promotes atherosclerosis regression via macrophage reprogramming</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Zimmer, Sebastian; Grebe, Alena; Bakke, Siril S.; Bode, Niklas; Halvorsen, Bente; Ulas, Thomas; Skjelland, Mona; De Nardo, Dominic; Labzin, Larisa I.; Kerksiek, Anja; Hempel, Chris; Heneka, Michael T.; Hawxhurst, Victoria; Fitzgerald, Michael L; Trebicka, Jonel; Gustafsson, Jan-Åke; Westerterp, Marit; Tall, Alan R.; Wright, Samuel D.; Espevik, Terje; Schultze, Joachim L.; Nickenig, Georg; Lütjohann, Dieter; Latz, Eicke</p> <p>2016-01-01</p> <p>Atherosclerosis is an inflammatory disease linked to elevated blood cholesterol levels. Despite ongoing advances in the prevention and treatment of atherosclerosis, cardiovascular disease remains the leading cause of death worldwide. Continuous retention of apolipoprotein B-containing lipoproteins in the subendothelial space causes <span class="hlt">a</span> local overabundance of free cholesterol. Since cholesterol accumulation and deposition of cholesterol crystals (CCs) triggers <span class="hlt">a</span> complex inflammatory response, we tested the efficacy of the cyclic oligosaccharide 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (CD), <span class="hlt">a</span> <span class="hlt">compound</span> that increases cholesterol solubility, in preventing and reversing atherosclerosis. Here we show that CD treatment of murine atherosclerosis reduced atherosclerotic plaque size and CC load, and promoted plaque regression even with <span class="hlt">a</span> continued cholesterol-rich diet. Mechanistically, CD increased oxysterol production in both macrophages and human atherosclerotic plaques, and promoted liver X receptor (LXR)-mediated transcriptional reprogramming to improve cholesterol efflux and exert anti-inflammatory effects. In vivo, this CD-mediated LXR agonism was required for the anti-atherosclerotic and anti-inflammatory effects of CD as well as for augmented reverse cholesterol transport. Since CD treatment in humans is safe and CD beneficially affects key mechanisms of atherogenesis, it may therefore be used clinically to prevent or treat human atherosclerosis. PMID:27053774</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23770429','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23770429"><span>The interaction of nifedipine with selected <span class="hlt">cyclodextrins</span> and the subsequent solubility-permeability trade-off.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Beig, Avital; Miller, Jonathan M; Dahan, Arik</p> <p>2013-11-01</p> <p>The purpose of this study was to investigate the interaction of 2-hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HPβCD) and 2,6-dimethyl-β-<span class="hlt">cyclodextrin</span> (DMβCD) with the lipophilic drug nifedipine and to investigate the subsequent solubility-permeability interplay. Solubility curves of nifedipine with HPβCD and DMβCD in MES buffer were evaluated using phase solubility methods. Then, the apparent permeability of nifedipine was investigated as <span class="hlt">a</span> function of increasing HPβCD/DMβCD concentration in the hexadecane-based PAMPA model. The interaction with nifedipine was CD dependent; significantly higher stability constant was obtained for DMβCD in comparison with HPβCD. Moreover, nifedipine displays different type of interaction with these CDs; <span class="hlt">a</span> 1:1 stoichiometric <span class="hlt">inclusion</span> complex was apparent with HPβCD, while 1:2 stoichiometry was apparent for DMβCD. In all cases, decreased apparent intestinal permeability of nifedipine as <span class="hlt">a</span> function of increasing CD level and nifedipine apparent solubility was obtained. <span class="hlt">A</span> quasi-equilibrium mass transport analysis was developed to explain this solubility-permeability interplay; the model enabled excellent quantitative prediction of nifedipine's permeability as <span class="hlt">a</span> function of CD concentrations. This work demonstrates that when using CDs in solubility-enabling formulations, <span class="hlt">a</span> trade-off exists between solubility increase and permeability decrease that must not be overlooked. This trade-off was found to be independent of the type of CD-drug interaction. The transport model presented here can aid in striking the appropriate solubility-permeability balance in order to achieve optimal overall absorption. Copyright © 2013 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5615528','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5615528"><span>Selective Removal of the Genotoxic <span class="hlt">Compound</span> 2-Aminopyridine in Water using Molecularly Imprinted Polymers Based on Magnetic Chitosan and β-<span class="hlt">Cyclodextrin</span></span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Zhang, Wei; Zhu, Zhiliang; Zhang, Hua; Qiu, Yanling</p> <p>2017-01-01</p> <p>To develop efficient materials with enhanced adsorption and selectivity for genotoxic 2-aminopyridine in water, based on magnetic chitosan (CTs) and β-<span class="hlt">cyclodextrin</span> (β-CD), the magnetic molecularly imprinted polymers (MMIPs) of Fe3O4-CTs@MIP and Fe3O4-MAH-β-CD@MIP were synthesized by <span class="hlt">a</span> molecular imprinting technique using 2-aminopyridine as <span class="hlt">a</span> template. The selective adsorption experiments for 2-aminopyridine were performed by four analogues including pyridine, aniline, 2-amino-5-chloropyridine and phenylenediamine. Results showed the target 2-aminopyridine could be selectively adsorbed and quickly separated by the synthesized MMIPs in the presence of the above structural analogues. The coexisting ions including Na+, K+, Mg2+, Ca2+, Cl− and SO42− showed little effect on the adsorption of 2-aminopyridine. The maximum adsorption capacity of 2-aminopyridine on Fe3O4-CTs@MIP and Fe3O4-MAH-β-CD@MIP was 39.2 mg·g−1 and 46.5 mg·g−1, respectively, which is much higher than values in previous reports. The comparison result with commercial activated carbon showed the obtained MMIPs had higher adsorption ability and selectivity for 2-aminopyridine. In addition, the synthesized MMIPs exhibited excellent performance of regeneration, which was used at least five times with little adsorption capacity loss. Therefore, the synthesized MMIPs are potential effective materials in applications for selective removal and analysis of the genotoxic <span class="hlt">compound</span> aminopyridine from environmental water. PMID:28858259</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2014AcSpA.131..424B','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2014AcSpA.131..424B"><span>Spectral, thermal, and molecular modeling studies on the encapsulation of selected sulfonamide drugs in β-<span class="hlt">cyclodextrin</span> nano-cavity</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Bani-Yaseen, Abdulilah Dawoud; Mo'ala, Abeer</p> <p>2014-10-01</p> <p>In the present work the <span class="hlt">inclusion</span> complexation of three sulfonamide (SA) drugs, namely sulfisoxazole (SSX), sulfamethizole (SMZ), and Sulfamethazine (STM) with β-<span class="hlt">cyclodextrin</span> (β-CD) has been investigated using UV-Vis spectroscopy, DSC, 1H NMR spectroscopy, and molecular modeling methods. The binding constant (Kb) of SA:β-CD <span class="hlt">inclusion</span> complexation was determined via applying the modified form of Benesi-Hildebrand equation employing the changes in absorbance at λmax. Obtained results revealed that SA drugs form 1:1 <span class="hlt">inclusion</span> complex with β-CD with Kb of 650, 1532, 714 M-1 at 25 °C for SSX, SMZ, and STM, respectively. The UV-Vis absorption spectra displayed solvatochromic behavior of bathochromic shift with decreasing solvent polarity that in turn is good agreement with their behavior in the presence of β-CD in terms of environment polarity dependency. The <span class="hlt">inclusion</span> complex formation between β-CD and tested SA drugs in liquid and solid states was confirmed by 1H NMR and DSC, respectively. Using semi-empirical quantum chemistry methods at PM3 theoretical level, <span class="hlt">inclusion</span> complexes' structures as well as energetic and thermodynamic parameters of encapsulation were elucidated. Obtained results revealed that the encapsulation is favorably energetic and enthalpic in nature with the <span class="hlt">inclusion</span> of the aniline moiety through the wide rim side of β-CD nano-cavity. Further, molecular modeling revealed that β-CD encapsulation of SA drugs reduced their (EHOMO - ELUMO) gap.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/20943339','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/20943339"><span>Enantiomeric separation of antimalarial drugs by capillary electrophoresis using neutral and negatively charged <span class="hlt">cyclodextrins</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Németh, Krisztina; Tárkányi, Gábor; Varga, Erzsébet; Imre, Tímea; Mizsei, Réka; Iványi, Róbert; Visy, Júlia; Szemán, Julianna; Jicsinszky, László; Szente, Lajos; Simonyi, Miklós</p> <p>2011-02-20</p> <p>Capillary electrophoresis (CE) methods for chiral resolution of five antimalarial drugs (primaquine, tafenoquine, mefloquine, chloroquine and quinacrine) were developed by using <span class="hlt">a</span> wide selection of neutral and anionic <span class="hlt">cyclodextrin</span> (CD) derivatives. The use of sulfobutyl-β-CD and carboxymethyl-β-CD (CMBCD) resulted in good resolution of quinacrine and tafenoquine, respectively. New results are presented for resolutions of chloroquine and mefloquine. Application of carboxyalkyl- and sulfobutyl-CD derivatives provided improved resolution for primaquine. The impurity in primaquine sample detected by CE was identified as quinocide by MS and NMR. CMBCD provided not only the best separation of primaquine from quinocide but also the simultaneous complete resolution of both <span class="hlt">compounds</span>. Copyright © 2010 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2017CPL...671...28T','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2017CPL...671...28T"><span>Thermodynamics and binding mode of novel structurally related 1,2,4-thiadiazole derivatives with native and modified <span class="hlt">cyclodextrins</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Terekhova, Irina V.; Chislov, Mikhail V.; Brusnikina, Maria A.; Chibunova, Ekaterina S.; Volkova, Tatyana V.; Zvereva, Irina A.; Proshin, Alexey N.</p> <p>2017-03-01</p> <p>Study of complex formation of <span class="hlt">cyclodextrins</span> with 1,2,4-thiadiazole derivatives intended for Alzheimer's disease treatment was carried out using 1H NMR, ITC and phase solubility methods. Structure of <span class="hlt">cyclodextrins</span> and thiadiazoles affects the binding mode and thermodynamics of complexation. The larger cavity of β- and γ-<span class="hlt">cyclodextrins</span> is more appropriate for deeper insertion of 1,2,4-thiadiazole derivatives which is accompanied by intensive dehydration and solvent reorganization. Benzene ring of the thiadiazoles is located inside macrocyclic cavity while piperidine ring is placed outside the cavity and can form H-bonds with <span class="hlt">cyclodextrin</span> exterior. Complexation with <span class="hlt">cyclodextrins</span> induces the enhancement of aqueous solubility of 1,2,4-thiadiazole derivatives.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28642042','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28642042"><span>Changes in membrane biophysical properties induced by the Budesonide/Hydroxypropyl-β-<span class="hlt">cyclodextrin</span> complex.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Dos Santos, Andreia G; Bayiha, Jules César; Dufour, Gilles; Cataldo, Didier; Evrard, Brigitte; Silva, Liana C; Deleu, Magali; Mingeot-Leclercq, Marie-Paule</p> <p>2017-10-01</p> <p>Budesonide (BUD), <span class="hlt">a</span> poorly soluble anti-inflammatory drug, is used to treat patients suffering from asthma and COPD (Chronic Obstructive Pulmonary Disease). Hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HPβCD), <span class="hlt">a</span> biocompatible <span class="hlt">cyclodextrin</span> known to interact with cholesterol, is used as <span class="hlt">a</span> drug-solubilizing agent in pharmaceutical formulations. Budesonide administered as an <span class="hlt">inclusion</span> complex within HPβCD (BUD:HPβCD) required <span class="hlt">a</span> quarter of the nominal dose of the suspension formulation and significantly reduced neutrophil-induced inflammation in <span class="hlt">a</span> COPD mouse model exceeding the effect of each molecule administered individually. This suggests the role of lipid domains enriched in cholesterol for inflammatory signaling activation. In this context, we investigated the effect of BUD:HPβCD on the biophysical properties of membrane lipids. On cellular models (<span class="hlt">A</span>549, lung epithelial cells), BUD:HPβCD extracted cholesterol similarly to HPβCD. On large unilamellar vesicles (LUVs), by using the fluorescent probes diphenylhexatriene (DPH) and calcein, we demonstrated an increase in membrane fluidity and permeability induced by BUD:HPβCD in vesicles containing cholesterol. On giant unilamellar vesicles (GUVs) and lipid monolayers, BUD:HPβCD induced the disruption of cholesterol-enriched raft-like liquid ordered domains as well as changes in lipid packing and lipid desorption from the cholesterol monolayers, respectively. Except for membrane fluidity, all these effects were enhanced when HPβCD was complexed with budesonide as compared with HPβCD. Since cholesterol-enriched domains have been linked to membrane signaling including pathways involved in inflammation processes, we hypothesized the effects of BUD:HPβCD could be partly mediated by changes in the biophysical properties of cholesterol-enriched domains. Copyright © 2017 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/23876498','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/23876498"><span>Sildenafil citrate monohydrate-<span class="hlt">cyclodextrin</span> nanosuspension complexes for use in metered-dose inhalers.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sawatdee, Somchai; Phetmung, Hirihattaya; Srichana, Teerapol</p> <p>2013-10-15</p> <p>Sildenafil is <span class="hlt">a</span> selective phosphodiesterase-5 inhibitor used for the treatment of erectile dysfunction and pulmonary hypertension. Sildenafil citrate monohydrate was complexed with α-, hydroxypropyl-β- and γ-<span class="hlt">cyclodextrin</span> (α-CD, HP-β-CD and γ-CD, respectively) to enhance its water solubility. The complexes of sildenafil citrate monohydrate with all types of CDs were characterized by phase solubility diagrams, (1)H and (13)C NMR, and dielectric constants. Sildenafil citrate monohydrate complexed with CDs was developed as nanosuspensions for use in <span class="hlt">a</span> pressurized metered-dose inhaler (pMDI). Sildenafil citrate monohydrate pMDI formulations were prepared by <span class="hlt">a</span> bottom-up process using dried ethanol as <span class="hlt">a</span> solvent and HFA-134<span class="hlt">a</span> as an antisolvent and propellant in order to form nanosuspensions. <span class="hlt">A</span> 3×3 factorial design was applied for the contents of the dried ethanol and HFA-134<span class="hlt">a</span> propellant. The phase solubility profiles of the sildenafil and <span class="hlt">cyclodextrins</span> were described as AL type with <span class="hlt">a</span> mole ratio 1:1. The piperazine moiety of sildenafil formed an <span class="hlt">inclusion</span> in the cavity of the CDs. The particle diameters of the sildenafil citrate monohydrate suspensions in pMDIs were all within <span class="hlt">a</span> nanosuspension size range. An assay of the sildenafil content showed that the formation of complexes with CDs was close to 100%. In the case of the formulations with CDs, the emitted doses varied within 97.4±10.8%, the fine particle fractions (FPFs) were in <span class="hlt">a</span> range of 45-81%, the fine particle dose (FPD) was 12.6±2.0 μg and the mass median aerodynamic diameters (MMADs) were 1.86±0.41 μm. In contrast, the formulations without CDs produced <span class="hlt">a</span> low emitted dose of sildenafil (<60%). Therefore, only sildenafil citrate monohydrate pMDI formulations containing CDs were suitable for use as aerosols. Copyright © 2013 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/15595572','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/15595572"><span>Drug-beta-<span class="hlt">cyclodextrin</span> containing pellets prepared with <span class="hlt">a</span> high-shear mixer.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Gainotti, Alessandro; Bettini, Ruggero; Gazzaniga, Andrea; Colombo, Paolo; Giordano, Ferdinando</p> <p>2004-01-01</p> <p>This work was aimed at investigating the preparation of beta-<span class="hlt">cyclodextrin</span>-microcrystalline cellulose pellets by means of <span class="hlt">a</span> high-shear mixer, both in the absence or in the presence of ibuprofen as model drug. Drug loading of pellets was accomplished by means of two alternative techniques: 1) solution layering or 2) powder layering. The prepared pellets were characterised in terms of size distribution, shape factor, friability and dissolution rate. The interaction between ibuprofen and beta-<span class="hlt">cyclodextrin</span> was monitored by Differential Scanning Calorimetry (DSC). Micro Fourier Transform Infrared spectroscopy (MicroFTIR) was applied to determine the distribution of components within each pellet on <span class="hlt">a</span> micro scale. Pellets with narrow size distribution and containing up to about 90% of BCD were prepared using water as binder. The process yield resulted around 84 and 63% for drug-free and medicate pellets respectively. Drug loaded pellets with favourable technological and biopharmaceutical characteristics can be obtained both by powder or solution layering techniques. The latter proved to be more suitable for producing pellets with high drug contents, reduced friability and high drug dissolution rates.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3663561','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3663561"><span>Polybrominated Dibenzo-p-Dioxins, Dibenzofurans, and Biphenyls: <span class="hlt">Inclusion</span> in the Toxicity Equivalency Factor Concept for Dioxin-Like <span class="hlt">Compounds</span></span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>van den Berg, Martin</p> <p>2013-01-01</p> <p>In 2011, <span class="hlt">a</span> joint World Health Organization (WHO) and United Nations Environment Programme (UNEP) expert consultation took place, during which the possible <span class="hlt">inclusion</span> of brominated analogues of the dioxin-like <span class="hlt">compounds</span> in the WHO Toxicity Equivalency Factor (TEF) scheme was evaluated. The expert panel concluded that polybrominated dibenzo-p-dioxins (PBDDs), dibenzofurans (PBDFs), and some dioxin-like biphenyls (dl-PBBs) may contribute significantly in daily human background exposure to the total dioxin toxic equivalencies (TEQs). These <span class="hlt">compounds</span> are also commonly found in the aquatic environment. Available data for fish toxicity were evaluated for possible <span class="hlt">inclusion</span> in the WHO-UNEP TEF scheme (van den Berg et al., 1998). Because of the limited database, it was decided not to derive specific WHO-UNEP TEFs for fish, but for ecotoxicological risk assessment, the use of specific relative effect potencies (REPs) from fish embryo assays is recommended. Based on the limited mammalian REP database for these brominated <span class="hlt">compounds</span>, it was concluded that sufficient differentiation from the present TEF values of the chlorinated analogues (van den Berg et al., 2006) was not possible. However, the REPs for PBDDs, PBDFs, and non-ortho dl-PBBs in mammals closely follow those of the chlorinated analogues, at least within one order of magnitude. Therefore, the use of similar interim TEF values for brominated and chlorinated congeners for human risk assessment is recommended, pending more detailed information in the future. PMID:23492812</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/24906752','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/24906752"><span>Porous silicon-<span class="hlt">cyclodextrin</span> based polymer composites for drug delivery applications.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Hernandez-Montelongo, J; Naveas, N; Degoutin, S; Tabary, N; Chai, F; Spampinato, V; Ceccone, G; Rossi, F; Torres-Costa, V; Manso-Silvan, M; Martel, B</p> <p>2014-09-22</p> <p>One of the main applications of porous silicon (PSi) in biomedicine is drug release, either as <span class="hlt">a</span> single material or as <span class="hlt">a</span> part of <span class="hlt">a</span> composite. PSi composites are attractive candidates for drug delivery systems because they can display new chemical and physical characteristics, which are not exhibited by the individual constituents alone. Since <span class="hlt">cyclodextrin</span>-based polymers have been proven efficient materials for drug delivery, in this work β-<span class="hlt">cyclodextrin</span>-citric acid in-situ polymerization was used to functionalize two kinds of PSi (nanoporous and macroporous). The synthesized composites were characterized by microscopy techniques (SEM and AFM), physicochemical methods (ATR-FTIR, XPS, water contact angle, TGA and TBO titration) and <span class="hlt">a</span> preliminary biological assay was performed. Both systems were tested as drug delivery platforms with two different model drugs, namely, ciprofloxacin (an antibiotic) and prednisolone (an anti-inflammatory), in two different media: pure water and PBS solution. Results show that both kinds of PSi/β-<span class="hlt">cyclodextrin</span>-citric acid polymer composites, nano- and macro-, provide enhanced release control for drug delivery applications than non-functionalized PSi samples. Copyright © 2014 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5831967','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=5831967"><span><span class="hlt">Cyclodextrin</span> Enhances Corneal Tolerability and Reduces Ocular Toxicity Caused by Diclofenac</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>Abdelkader, Hamdy; Fathalla, Zeinab; Moharram, Hossam; Ali, Taha F. S.</p> <p>2018-01-01</p> <p>With advances in refractive surgery and demand for cataract removal and lens replacement, the ocular use of nonsteroidal anti-inflammatory drugs (NSAIDs) has increased. One of the most commonly used NSAIDs is diclofenac (Diclo). In this study, <span class="hlt">cyclodextrins</span> (CDs), α-, β-, γ-, and HP-β-CDs, were investigated with in vitro irritation and in vivo ulceration models in rabbits to reduce Diclo toxicity. Diclo-, α-, β-, γ-, and HP-β-CD <span class="hlt">inclusion</span> complexes were prepared and characterized and Diclo-CD complexes were evaluated for corneal permeation, red blood cell (RBCs) haemolysis, corneal opacity/permeability, and toxicity. Guest- (Diclo-) host (CD) solid <span class="hlt">inclusion</span> complexes were formed only with β-, γ-, and HP-β-CDs. Amphipathic properties for Diclo were recorded and this surfactant-like functionality might contribute to the unwanted effects of Diclo on the surface of the eye. Contact angle and spreading coefficients were used to assess Diclo-CDs in solution. Reduction of ocular toxicity 3-fold to16-fold and comparable corneal permeability to free Diclo were recorded only with Diclo-γ-CD and Diclo-HP-β-CD complexes. These two complexes showed faster healing rates without scar formation compared with exposure to the Diclo solution and to untreated groups. This study also highlighted that Diclo-γ-CD and Diclo-HP-β-CD demonstrated fast healing without scar formation. PMID:29636847</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28541948','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28541948"><span>Attached β-<span class="hlt">cyclodextrin</span>/γ-(2,3-epoxypropoxy) propyl trimethoxysilane to graphene oxide and its application in copper removal.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Yu, Zongxue; Chen, Qi; Lv, Liang; Pan, Yang; Zeng, Guangyong; He, Yi</p> <p>2017-05-01</p> <p>The environmental applications of graphene oxide and β-<span class="hlt">cyclodextrin</span> (β-CD) have attracted great attention since their first discovery. Novel nanocomposites were successfully prepared by using an esterification reaction between β-<span class="hlt">cyclodextrin</span>/γ-(2,3-epoxypropoxy) propyl trimethoxysilane grafted graphene oxide (β-CD/GPTMS/GO). The β-CD/GPTMS/GO nanocomposites were used to remove the Cu 2+ from aqueous solutions. The characteristics of β-CD/GPTMS/GO were detected by scanning electron microscopy (SEM), Fourier transform infrared, X-ray diffraction (XRD), thermogravimetric analysis (TG) and energy dispersive X-ray (EDX). The dispersibility of graphene oxide was excellent due to the addition of β-CD. The adsorption isotherms data obtained at the optimum pH 7 were fitted by Langmuir isotherm model. The excellent adsorption properties of β-CD/GPTMS/GO for Cu 2+ ions could be attributed to the apolar cavity structure of β-CD, the high surface area and abundant functional groups on the surface of GO. The adsorption patterns of β-CD/GPTMS/GO were electrostatic attraction, formation of host-guest <span class="hlt">inclusion</span> complexes and the ion exchange adsorption. The efficient adsorption of β-CD/GPTMS/GO for Cu 2+ ions suggested that these novel nanocomposites may be ideal candidates for removing other cation pollutants from waste water.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li class="active"><span>24</span></li> <li><a href="#" onclick='return showDiv("page_25");'>25</a></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_24 --> <div id="page_25" class="hiddenDiv"> <div class="row"> <div class="col-sm-12"> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li class="active"><span>25</span></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div> </div> <div class="row"> <div class="col-sm-12"> <ol class="result-class" start="481"> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2009inpo.book..115T','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2009inpo.book..115T"><span>Molecular Processing of Polymers with <span class="hlt">Cyclodextrins</span></span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Tonelli, Alan E.</p> <p></p> <p>We summarize our recent studies employing the cyclic starch derivatives called <span class="hlt">cyclodextrins</span> (CDs) to both nanostructure and functionalize polymers. Two important structural characteristics of CDs are taken advantage of to achieve these goals. First the ability of CDs to form noncovalent <span class="hlt">inclusion</span> complexes (ICs) with <span class="hlt">a</span> variety of guest molecules, including many polymers, by threading and <span class="hlt">inclusion</span> into their relatively hydrophobic interior cavities, which are roughly cylindrical with diameters of ˜ 0.5 - 1.0 nm. α-, β-, and γ-CD contain six, seven, and eight α-1,4-linked glucose units, respectively. Warm water washing of polymer-CD-ICs containing polymer guests insoluble in water or treatment with amylase enzymes serves to remove the host CDs and results in the coalescence of the guest polymers into solid samples. When guest polymers are coalesced from the CD-ICs by removing their host CDs, they are observed to solidify with structures, morphologies, and even conformations that are distinct from bulk samples made from their solutions and melts. Molecularly mixed, intimate blends of two or more polymers that are normally immiscible can be obtained from their common CD-ICs, and the phase segregation of incompatible blocks can be controlled (suppressed or increased) in CD-IC coalesced block copolymers. In addition, additives may be more effectively delivered to polymers in the form of their crystalline CD-ICs or soluble CD-rotaxanes. Secondly, the many hydroxyl groups attached to the exterior rims of CDs, in addition to conferring water solubility, provide an opportunity to covalently bond them to polymers either during their syntheses or via postpolymerization reactions. Polymers containing CDs in their backbones or attached to their side chains are observed to more readily accept and retain additives, such as dyes and fragrances. Processing with CDs can serve to both nanostructure and functionalize polymers, leading to greater understanding of their behaviors</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12633708','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12633708"><span>Spectrofluorimetric study of host-guest complexation of ibuprofen with beta-<span class="hlt">cyclodextrin</span> and its analytical application.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Manzoori, Jamshid L; Amjadi, Mohammad</p> <p>2003-03-15</p> <p>The characteristics of host-guest complexation between beta-<span class="hlt">cyclodextrin</span> (beta-CD) and two forms of ibuprofen (protonated and deprotonated) were investigated by fluorescence spectrometry. 1:1 stoichiometries for both complexes were established and their association constants at different temperatures were calculated by applying <span class="hlt">a</span> non-linear regression method to the change in the fluorescence of ibuprofen that brought about by the presence of beta-CD. The thermodynamic parameters (deltaH, deltaS and deltaG) associated with the <span class="hlt">inclusion</span> process were also determined. Based on the obtained results, <span class="hlt">a</span> sensitive spectrofluorimetric method for the determination of ibuprofen was developed with <span class="hlt">a</span> linear range of 0.1-2 microg ml(-1) and <span class="hlt">a</span> detection limit of 0.03 microg ml(-1). The method was applied satisfactorily to the determination of ibuprofen in pharmaceutical preparations. Copyright 2002 Elsevier Science B.V.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29735104','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29735104"><span>Inhibition of interaction between epigallocatechin-3-gallate and myofibrillar protein by <span class="hlt">cyclodextrin</span> derivatives improves gel quality under oxidative stress.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Zhang, Yumeng; Chen, Lin; Lv, Yuanqi; Wang, Shuangxi; Suo, Zhiyao; Cheng, Xingguang; Xu, Xinglian; Zhou, Guanghong; Li, Zhixi; Feng, Xianchao</p> <p>2018-06-01</p> <p>High levels of polyphenols can interact with myofibrillar proteins (MPs), causing damage to <span class="hlt">a</span> MP emulsion gel. In this study, β-<span class="hlt">cyclodextrins</span> were used to reduce covalent and non-covalent interaction between epigallocatechin-3-gallate (EGCG) and MPs under oxidative stress. The loss of both thiol and free amine groups and the unfolding of MPs caused by EGCG (80 μM/g protein) were significantly prevented by β-<span class="hlt">cyclodextrins</span>, and the structural stability and solubility were improved. MP emulsion gel treated with EGCG (80 μM/g protein) had the highest cooking loss (68.64%) and gel strength (0.51 N). Addition of β-<span class="hlt">cyclodextrins</span> significantly reduced cooking loss (26.24-58.20%) and improved gel strength (0.31-0.41 N) of MP emulsion gel jeopardized by EGCG under oxidative stress. Damage to the emulsifying properties of MPs caused by EGCG was significantly prevented by addition of β-<span class="hlt">cyclodextrins</span>. β-<span class="hlt">cyclodextrins</span> reduced interaction between EGCG and MPs in the order Methyl-β-cyclodextrin > (2-Hydroxypropyl)-β-cyclodextrin > β-<span class="hlt">cyclodextrin</span>. In absence of EGCG, addition of β-<span class="hlt">cyclodextrins</span> partly protected MPs from oxidative attack and improved its solubility. It is concluded that β-<span class="hlt">cyclodextrins</span> does not markedly reduce the antioxidant ability of EGCG according to carbonyl analysis, and can effectively increase EGCG loading to potentially provide more durable antioxidant effect for meat products during processing, transportation and storage. Copyright © 2018 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3391002','PMC'); return false;" href="https://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3391002"><span>Evaluation of octyl p-methoxycinnamate included in liposomes and <span class="hlt">cyclodextrins</span> in anti-solar preparations: preparations, characterizations and in vitro penetration studies</span></a></p> <p><a target="_blank" href="http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pmc">PubMed Central</a></p> <p>de Souza de Bustamante Monteiro, Mariana Sato; Ozzetti, Rafael Antonio; Vergnanini, André Luiz; de Brito-Gitirana, Lycia; Volpato, Nadia Maria; de Freitas, Zaida Maria Faria; Ricci-Júnior, Eduardo; dos Santos, Elisabete Pereira</p> <p>2012-01-01</p> <p>Purpose Awareness of the harmful effects of ultraviolet radiation has led to the increasing use of sunscreens, thus, the development of safe and effective antisolar preparations is important. The <span class="hlt">inclusion</span> of sunscreen molecules in different release systems, like liposomes (lipo) and <span class="hlt">cyclodextrins</span> (CD) is therefore required. Methods The in vivo sun protection factor (SPF), water resistance, and in vitro transdermal penetration test of octyl p-methoxycinnamate (OMC) in different dispersions, such as OMC encapsulated in liposomes (lipo/OMC), OMC encapsulated in β-<span class="hlt">cyclodextrins</span> (β-CD/OMC), OMC encapsulated in both release systems (lipo/OMC and β-CD/OMC), and an OMC-free formulation were determined. Results Although the formulation containing only the lipo/OMC system revealed high value of in vivo SPF (11.0 ± 1.3) and water resistance (SPF = 10.3 ± 2.2), the formulation containing both release systems (lipo/OMC + β-<span class="hlt">cyclodextrin</span>/OMC) showed the best result in the in vivo SPF test (11.6 ± 1.6). In the penetration test, the formulation containing the lipo/OMC system had better performance, since <span class="hlt">a</span> high amount of OMC in the epidermis (18.04 ± 1.17 μg) and <span class="hlt">a</span> low amount of OMC in the dermis (9.4 ± 2.36 μg) were observed. These results suggest that liposomes interact with the cells of the stratum corneum, promoting retention of OMC in this layer. Conclusion According to our study, the lipo/OMC system is the most advantageous release system, due to its ability to both increase the amount of OMC in the epidermis and decrease the risk of percutaneous absorption. PMID:22787399</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2017PhRvE..95e2416R','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2017PhRvE..95e2416R"><span>β -<span class="hlt">Cyclodextrin</span> polymer binding to DNA: Modulating the physicochemical parameters</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Rocha, J. C. B.; Silva, E. F.; Oliveira, M. F.; Sousa, F. B.; Teixeira, A. V. N. C.; Rocha, M. S.</p> <p>2017-05-01</p> <p><span class="hlt">Cyclodextrins</span> and <span class="hlt">cyclodextrins</span>-modified molecules have interesting and appealing properties due to their capacity to host components that are normally insoluble or poorly soluble in water. In this work, we investigate the interaction of <span class="hlt">a</span> β -<span class="hlt">cyclodextrin</span> polymer (poly-β -CD) with λ -DNA. The polymers are obtained by the reaction of β -CD with epichlorohydrin in alkaline conditions. We have used optical tweezers to characterize the changes of the mechanical properties of DNA molecules by increasing the concentration of poly-β -CD in the sample. The physical chemistry of the interaction is then deduced from these measurements by using <span class="hlt">a</span> recently developed quenched-disorder statistical model. It is shown that the contour length of the DNA does not change in the whole range of poly-β -CD concentration (<300 μ M ). On the other hand, significant alterations were observed in the persistence length that identifies two binding modes corresponding to the clustering of ˜2.6 and ˜14 polymer molecules along the DNA double helix, depending on the polymer concentration. Comparing these results with the ones obtained for monomeric β -CD, it was observed that the concentration of CD that alters the DNA persistence length is considerably smaller when in the polymeric form. Also, the binding constant of the polymer-DNA interaction is three orders of magnitude higher than the one found for native (monomeric) β -CD. These results show that the polymerization of the β -CD strongly increases its binding affinity to the DNA molecule. This property can be wisely used to modulate the binding of <span class="hlt">cyclodextrins</span> to the DNA double helix.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28167265','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28167265"><span>Curcumin complexation with <span class="hlt">cyclodextrins</span> by the autoclave process: Method development and characterization of complex formation.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Hagbani, Turki Al; Nazzal, Sami</p> <p>2017-03-30</p> <p>One approach to enhance curcumin (CUR) aqueous solubility is to use <span class="hlt">cyclodextrins</span> (CDs) to form <span class="hlt">inclusion</span> complexes where CUR is encapsulated as <span class="hlt">a</span> guest molecule within the internal cavity of the water-soluble CD. Several methods have been reported for the complexation of CUR with CDs. Limited information, however, is available on the use of the autoclave process (AU) in complex formation. The aims of this work were therefore to (1) investigate and evaluate the AU cycle as <span class="hlt">a</span> complex formation method to enhance CUR solubility; (2) compare the efficacy of the AU process with the freeze-drying (FD) and evaporation (EV) processes in complex formation; and (3) confirm CUR stability by characterizing CUR:CD complexes by NMR, Raman spectroscopy, DSC, and XRD. Significant differences were found in the saturation solubility of CUR from its complexes with CD when prepared by the three complexation methods. The AU yielded <span class="hlt">a</span> complex with expected chemical and physical fingerprints for <span class="hlt">a</span> CUR:CD <span class="hlt">inclusion</span> complex that maintained the chemical integrity and stability of CUR and provided the highest solubility of CUR in water. Physical and chemical characterizations of the AU complexes confirmed the encapsulated of CUR inside the CD cavity and the transformation of the crystalline CUR:CD <span class="hlt">inclusion</span> complex to an amorphous form. It was concluded that the autoclave process with its short processing time could be used as an alternate and efficient methods for drug:CD complexation. Copyright © 2017 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://www.ars.usda.gov/research/publications/publication/?seqNo115=330476','TEKTRAN'); return false;" href="http://www.ars.usda.gov/research/publications/publication/?seqNo115=330476"><span>Glycemic response to corn starch modified with <span class="hlt">cyclodextrin</span> glycosyltransferase and its relationship to physical properties</span></a></p> <p><a target="_blank" href="https://www.ars.usda.gov/research/publications/find-a-publication/">USDA-ARS?s Scientific Manuscript database</a></p> <p></p> <p></p> <p>Corn starch was modified with <span class="hlt">cyclodextrin</span> glycosyltransferase (CGTase) below the gelatinization temperature. The porous, partially hydrolyzed, granules with or without CGTase hydrolysis products, <span class="hlt">cyclodextrins</span> (CDs) and short chain maltodextrins, may be used as an alternative to modified corn starc...</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('http://adsabs.harvard.edu/abs/2016E%26ES...36a2054R','NASAADS'); return false;" href="http://adsabs.harvard.edu/abs/2016E%26ES...36a2054R"><span>Encapsulation of bioactive <span class="hlt">compound</span> from extracted jasmine flower using β-<span class="hlt">Cyclodextrin</span> via electrospray</span></a></p> <p><a target="_blank" href="http://adsabs.harvard.edu/abstract_service.html">NASA Astrophysics Data System (ADS)</a></p> <p>Rahmam., S.; Naim., M. N.; Ng., E.; Mokhtar, M. Nn; Abu Bakar, N. F.</p> <p>2016-06-01</p> <p>The ability of electrospray to encapsulate the bioactive <span class="hlt">compound</span> extracted from Jasmine flower with β-Cyclodextrion (β-CD) without any thermal-assisted processing was demonstrated in this study. The extraction of Jasmine <span class="hlt">compound</span> were conducted using sonicator at 70 000 Hz, for 10 minutes and followed by mixing of the filtered <span class="hlt">compound</span> with β-CD. Then, the mixture was electrosprayed under <span class="hlt">a</span> stable Taylor cone jet mode at the voltage of 4 - 5 kV, with flow rate of 0.2 ml/hour. The aluminum substrate that used for collecting the deposit was placed at 30 cm from the needle's tip to allow the occurrence of evaporation and droplet fission until the droplet transform to solid particles. Characteristics of solidified bioactive <span class="hlt">compound</span> from Jasmine flower (non-encapsulated <span class="hlt">compound</span>) and solidified bioactive <span class="hlt">compound</span> with β-CD (encapsulated <span class="hlt">compound</span>) were studied in this work. From SEM images, it can be observed that the particles size distribution of encapsulated <span class="hlt">compound</span> deposits have better deposition array and did not aggregate with each other compared to the non-encapsulated <span class="hlt">compound</span>. FE-SEM images of encapsulated <span class="hlt">compound</span> deposits indicate more solid crystal looks while non-encapsulated <span class="hlt">compound</span> was obtained in the porous form. The electrospray process in this work has successfully encapsulated the Jasmine <span class="hlt">compound</span> with β-CD without any thermal-assisted process. The encapsulation occurrence was determined using FTIR analysis. Identical peaks that referred to the β-CD were found on the encapsulated <span class="hlt">compound</span> demonstrated that most deposits were encapsulated with β-CD.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27369582','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27369582"><span>Repellent effects of Melaleuca alternifolia (tea tree) oil against cattle tick larvae (Rhipicephalus australis) when formulated as emulsions and in β-<span class="hlt">cyclodextrin</span> <span class="hlt">inclusion</span> complexes.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Yim, Wei Tsun; Bhandari, Bhesh; Jackson, Louise; James, Peter</p> <p>2016-07-30</p> <p>Rhipicephalus australis (formerly Boophilus microplus) is <span class="hlt">a</span> one host tick responsible for major economic loss in tropical and subtropical cattle production enterprises. Control is largely dependent on the application of acaricides but resistance has developed to most currently registered chemical groups. Repellent <span class="hlt">compounds</span> that prevent initial attachment of tick larvae offer <span class="hlt">a</span> potential alternative to control with chemical toxicants. The repellent effects of Melaleuca alternifolia oil (TTO) emulsions and two β-<span class="hlt">cyclodextrin</span> complex formulations, <span class="hlt">a</span> slow release form (SR) and <span class="hlt">a</span> modified faster release form (FR), were examined in <span class="hlt">a</span> series of laboratory studies. Emulsions containing 4% and 5% TTO applied to cattle hair in laboratory studies completely repelled ascending tick larvae for 24h whereas 2% and 3% formulations provided 80% protection. At 48h, 5% TTO provided 78% repellency but lower concentrations repelled less than 60% of larvae. In <span class="hlt">a</span> study conducted over 15 days, 3% TTO emulsion applied to cattle hair provided close to 100% repellency for 2 days, but then protection fell to 23% by day 15. The FR formulation gave significantly greater repellency than the emulsion and the SR formulation from day 3 until the end of the study (P<0.05), providing almost complete repellency at day 3 (99.5%), then decreasing over the period of the study to 49% repellency at day 15. Proof of concept is established for the use of appropriately designed controlled-release formulations to extend the period of repellency provided by TTO against R. australis larvae. Copyright © 2016 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28213944','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28213944"><span>Separation of hydroxynorketamine stereoisomers using capillary electrophoresis with sulfated β-<span class="hlt">cyclodextrin</span> and highly sulfated γ-<span class="hlt">cyclodextrin</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sandbaumhüter, Friederike A; Theurillat, Regula; Thormann, Wolfgang</p> <p>2017-08-01</p> <p>The racemic N-methyl-d-aspartate receptor antagonist ketamine is used in anesthesia, analgesia and the treatment of depressive disorders. It is known that interactions of hydroxylated norketamine metabolites and 5,6-dehydronorketamine (DHNK) with the α 7 -nicotinic acetylcholine receptor and the α-amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor are responsible for the antidepressive effects. Ketamine and its first metabolite norketamine are not active on these receptors. As stereoselectivity plays <span class="hlt">a</span> role in ketamine metabolism, <span class="hlt">a</span> cationic capillary electrophoresis based method capable of resolving and analyzing the stereoisomers of four hydroxylated norketamine metabolites, norketamine and DHNK was developed. The assay is based on liquid/liquid extraction of the analytes from the biological matrix, electrokinetic sample injection across <span class="hlt">a</span> buffer plug and analysis of the stereoisomers in <span class="hlt">a</span> phosphate background electrolyte (BGE) at pH 3 comprising <span class="hlt">a</span> mixture of sulfated β-<span class="hlt">cyclodextrin</span> (5 mg/mL) and highly sulfated γ-<span class="hlt">cyclodextrin</span> (0.1%). The method was used to analyze samples of an in vitro study in which ketamine was incubated with equine liver microsomes and in plasma samples of dogs and horses that were collected after an i.v. bolus injection of racemic ketamine. © 2017 WILEY-VCH Verlag GmbH & Co. KGa<span class="hlt">A</span>, Weinheim.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12408908','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12408908"><span>Comparative studies of the influence of <span class="hlt">cyclodextrins</span> on the stability of the sunscreen agent, 2-ethylhexyl-p-methoxycinnamate.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Scalia, Santo; Casolari, Alberto; Iaconinoto, Antonietta; Simeoni, Silvia</p> <p>2002-11-07</p> <p>The effects of beta-<span class="hlt">cyclodextrin</span> (beta-CD) and hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> (HP-beta-CD) on the base-catalyzed degradation and light-induced decomposition of the sunscreen agent, trans-2-ethylhexyl-p-methoxycinnamate (trans-EHMC) were investigated. Reversed-phase liquid chromatography was used to study the interaction between natural and modified <span class="hlt">cyclodextrins</span>, added to the mobile phase, and the sunscreen. Among the available <span class="hlt">cyclodextrins</span> (beta-CD, HP-beta-CD, hydroxypropyl-alpha-<span class="hlt">cyclodextrin</span> and hydroxypropyl-gamma-<span class="hlt">cyclodextrin</span>), only HP-beta-CD and beta-CD produced <span class="hlt">a</span> significant decrease in the chromatographic retention of trans-EHMC. The complexation of the sunscreen agent with HP-beta-CD and beta-CD was confirmed by thermal analysis and nuclear magnetic resonance spectroscopy. beta-CD depressed the decomposition of trans-EHMC in alkaline solutions more effectively than HP-beta-CD. Moreover, the irradiation-induced degradation of the sunscreen agent in emulsion vehicles was reduced by complexation with beta-CD (the extent of degradation was 26.1% for the complex compared to 35.8% for free trans-EHMC) whereas HP-beta-CD had no significant effect. Therefore, the complex of beta-CD with trans-EHMC enhances the chemical- and photo-stability of the sunscreen agent. Moreover, it limits adverse interactions of the UV filter with other formulation ingredients.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/12207314','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/12207314"><span>Enantioselective analysis of ibuprofen in human plasma by anionic <span class="hlt">cyclodextrin</span>-modified electrokinetic chromatography.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Jabor, Valquíria A P; Lanchote, Vera L; Bonato, Pierina S</p> <p>2002-09-01</p> <p>This paper reports the development of <span class="hlt">a</span> rapid method for the enantioselective analysis of the nonsteroidal anti-inflammatory drug ibuprofen in human plasma by capillary electrophoresis employing the anionic <span class="hlt">cyclodextrin</span>-modified electrokinetic chromatography mode. Sample cleanup was carried out by acidification with HCl followed by liquid-liquid extraction with hexane:isopropanol (99:1 v/v). The complete enantioselective analysis was performed within 10 min, using 100 mmol L(-1) phosphoric acid/triethanolamine buffer, pH 2.6, containing 2.0% w/v sulfated beta-<span class="hlt">cyclodextrin</span> as chiral selector; fenoprofen, another nonsteroidal anti-inflammatory drug, was used as internal standard. The calibration curves were linear over the concentration range of 0.25-125.0 microg mL(-1) for each enantiomer of ibuprofen. The mean recoveries for ibuprofen enantiomers were up to 85%. The enantiomers studied could be quantified at three different concentrations (0.5, 5.0 and 50.0 microg mL(-1)) with <span class="hlt">a</span> coefficient of variation and relative error not higher than 15%. The quantitation limit was 0.2 microg mL(-1) for (+)-(S)- and (-)-(R)-ibuprofen using 1 mL of human plasma. The plasma endogenous <span class="hlt">compounds</span> and other drugs did not interfere with the present assay. The analysis of real plasma samples obtained from <span class="hlt">a</span> healthy volunteer after administration of 600 mg of racemic ibuprofen showed <span class="hlt">a</span> maximum plasma level of 29.6 and 39.9 microg mL(-1) of (-)-(R)- and (+)-(S)-ibuprofen, respectively, and the area under plasma concentration-time curve AUC(0-infinity) (+)-(S)/AUC(0-infinity) (-)-(R) ratio was 1.87.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26739777','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26739777"><span>Development of curcumin-<span class="hlt">cyclodextrin</span>/cellulose nanocrystals complexes: New anticancer drug delivery systems.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Ndong Ntoutoume, Gautier M A; Granet, Robert; Mbakidi, Jean Pierre; Brégier, Frédérique; Léger, David Y; Fidanzi-Dugas, Chloë; Lequart, Vincent; Joly, Nicolas; Liagre, Bertrand; Chaleix, Vincent; Sol, Vincent</p> <p>2016-02-01</p> <p>The synthesis of curcumin-<span class="hlt">cyclodextrin</span>/cellulose nanocrystals (CNCx) nano complexes was performed. CNCx were functionalized by ionic association with cationic β-<span class="hlt">cyclodextrin</span> (CD) and CD/CNCx complexes were used to encapsulate curcumin. Preliminary in vitro results showed that the resulting curcumin-CD/CNCx complexes exerted antiproliferative effect on colorectal and prostatic cancer cell lines, with IC50s lower than that of curcumin alone. Copyright © 2015 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/29635617','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/29635617"><span>Surfactant Dysfunction in ARDS and Bronchiolitis is Repaired with <span class="hlt">Cyclodextrins</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Al-Saiedy, Mustafa; Gunasekara, Lasantha; Green, Francis; Pratt, Ryan; Chiu, Andrea; Yang, Ailian; Dennis, John; Pieron, Cora; Bjornson, Candice; Winston, Brent; Amrein, Matthias</p> <p>2018-03-01</p> <p>Acute respiratory distress syndrome (ARDS) is caused by many factors including inhalation of toxicants, acute barotrauma, acid aspiration, and burns. Surfactant function is impaired in ARDS and acute airway injury resulting in high surface tension with alveolar and small airway collapse, edema, hypoxemia, and death. In this study, we explore the mechanisms whereby surfactant becomes dysfunctional in ARDS and bronchiolitis and its repair with <span class="hlt">a</span> <span class="hlt">cyclodextrin</span> drug that sequesters cholesterol. We used in vitro model systems, <span class="hlt">a</span> mouse model of ARDS, and samples from patients with acute bronchiolitis. Surface tension was measured by captive bubble surfactometry. Patient samples showed severe surfactant inhibition even in the absence of elevated cholesterol levels. Surfactant was also impaired in ARDS mice where the cholesterol to phospholipid ratio (W/W%) was increased. Methyl-β-<span class="hlt">cyclodextrin</span> (MβCD) restored surfactant function to normal in both human and animal samples. Model studies showed that the inhibition of surfactant was due to both elevated cholesterol and an interaction between cholesterol and oxidized phospholipids. MβCD was also shown to have anti-inflammatory effects. Inhaled <span class="hlt">cyclodextrins</span> have potential for the treatment of ARDS. They could be delivered in <span class="hlt">a</span> portable device carried in combat and used following exposure to toxic gases and fumes or shock secondary to hemorrhage and burns.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/25188303','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/25188303"><span>Insights on novel particulate self-assembled drug delivery beads based on partial <span class="hlt">inclusion</span> complexes between triglycerides and <span class="hlt">cyclodextrins</span>.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Aburahma, Mona Hassan</p> <p>2016-09-01</p> <p>Most of the newly designed drug molecules are lipophilic in nature and often encounter erratic absorption and low bioavailability after oral administration. Finding ways to enhance the absorption and bioavailability of these lipophilic drugs is one of the major challenges that face pharmaceutical industry nowadays. In view of that, the purpose of this review is to shed some light on <span class="hlt">a</span> novel particulate self-assembling system named "beads" than can act as <span class="hlt">a</span> safe carrier for delivering lipophilic drugs. The beads are prepared simply by mixing oils with <span class="hlt">cyclodextrin</span> (CD) aqueous solution in mild conditions. <span class="hlt">A</span> unique interaction between oil components and CD molecules occurs to form in situ surface-active complexes which are prerequisites for beads formation. This review mainly focuses on the fundamentals of beads preparation through reviewing present, yet scarce, literature. The key methods used for beads characterization are discussed in details. Also, the potential mechanisms by which beads increase the bioavailability of lipophilic drugs are illustrated. Finally, the related research areas that needs to be addressed in future for optimizing this promising delivery system are briefly outlined.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28962762','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28962762"><span>Construction of 6-thioguanine and 6-mercaptopurine carriers based on β<span class="hlt">cyclodextrins</span> and gold nanoparticles.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sierpe, R; Noyong, Michael; Simon, Ulrich; Aguayo, D; Huerta, J; Kogan, Marcelo J; Yutronic, N</p> <p>2017-12-01</p> <p>As <span class="hlt">a</span> novel strategy to overcome some of the therapeutic disadvantages of 6-thioguanine (TG) and 6-mercaptopurine (MP), we propose the <span class="hlt">inclusion</span> of these drugs in β<span class="hlt">cyclodextrin</span> (βCD) to form the complexes βCD-TG and βCD-MP, followed by subsequent interaction with gold nanoparticles (AuNPs), generating the ternary systems: βCD-TG-AuNPs and βCD-MP-AuNPs. This modification increased their solubility and improved their stability, betting by <span class="hlt">a</span> site-specific transport due to their nanometric dimensions, among other advantages. The formation of the complexes was confirmed using powder X-ray diffraction, thermogravimetric analysis and one and two-dimensional NMR. <span class="hlt">A</span> theoretical study using DFT and molecular modelling was conducted to obtain the more stable tautomeric species of TG and MP in solution and confirm the proposed <span class="hlt">inclusion</span> geometries. The deposition of AuNPs onto βCD-TG and βCD-MP via sputtering was confirmed by UV-vis spectroscopy. Subsequently, the ternary systems were characterized by TEM, FE-SEM and EDX to directly observe the deposited AuNPs and evaluate their sizes, size dispersion, and composition. Finally, the in vitro permeability of the ternary systems was studied using parallel artificial membrane permeability assay (PAMPA). Copyright © 2017 Elsevier Ltd. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/26410753','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/26410753"><span>Interest of <span class="hlt">cyclodextrins</span> in spray-dried microparticles formulation for sustained pulmonary delivery of budesonide.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Dufour, Gilles; Bigazzi, William; Wong, Nelson; Boschini, Frederic; de Tullio, Pascal; Piel, Geraldine; Cataldo, Didier; Evrard, Brigitte</p> <p>2015-11-30</p> <p>To achieve an efficient lung delivery and efficacy, both active ingredient aerosolisation properties and permeability through the lung need to be optimized. To overcome these challenges, the present studies aim to develop <span class="hlt">cyclodextrin</span>-based spray-dried microparticles containing <span class="hlt">a</span> therapeutic corticosteroid (budesonide) that could be used to control airway inflammation associated with asthma. The complexation between budesonide and hydroxypropyl-β-<span class="hlt">cyclodextrin</span> (HPBCD) has been investigated. Production of inhalation powders was carried out using <span class="hlt">a</span> bi-fluid nozzle spray dryer and was optimized based on <span class="hlt">a</span> design of experiments. Spray-dried microparticles display <span class="hlt">a</span> specific "deflated-ball like shape" associated with an appropriate size for inhalation. Aerodynamic assessment show that the fine particle fraction was increased compared to <span class="hlt">a</span> classical lactose-based budesonide formulation (44.05 vs 26.24%). Moreover, the budesonide permeability out of the lung was shown to be reduced in the presence of <span class="hlt">cyclodextrin</span> complexes. The interest of this sustained budesonide release was evaluated in <span class="hlt">a</span> mouse model of asthma. The anti-inflammatory effect was compared to <span class="hlt">a</span> non-complexed budesonide formulation at the same concentration and attests the higher anti-inflammatory activity reach with the <span class="hlt">cyclodextrin</span>-based formulation. This strategy could therefore be of particular interest for improving lung targeting while decreasing systemic side effects associated with high doses of corticosteroids. In conclusion, this works reports that <span class="hlt">cyclodextrins</span> could be used in powder for inhalation, both for their abilities to improve active ingredient aerosolisation properties and further to their dissolution in lung fluid, to decrease permeability out of the lungs leading to an optimized activity profile. Copyright © 2015 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/28171725','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/28171725"><span>Fluorinated Chaperone-β-<span class="hlt">Cyclodextrin</span> Formulations for β-Glucocerebrosidase Activity Enhancement in Neuronopathic Gaucher Disease.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>García-Moreno, M Isabel; de la Mata, Mario; Sánchez-Fernández, Elena M; Benito, Juan M; Díaz-Quintana, Antonio; Fustero, Santos; Nanba, Eiji; Higaki, Katsumi; Sánchez-Alcázar, José A; García Fernández, José M; Ortiz Mellet, Carmen</p> <p>2017-03-09</p> <p>Amphiphilic glycomimetics encompassing <span class="hlt">a</span> rigid, undistortable nortropane skeleton based on 1,6-anhydro-l-idonojirimycin and <span class="hlt">a</span> polyfluorinated antenna, when formulated as the corresponding <span class="hlt">inclusion</span> complexes with β-<span class="hlt">cyclodextrin</span> (βCD), have been shown to behave as pharmacological chaperones (PCs) that efficiently rescue lysosomal β-glucocerebrosidase mutants associated with the neuronopathic variants of Gaucher disease (GD), including the highly refractory L444P/L444P and L444P/P415R single nucleotide polymorphs, in patient fibroblasts. The body of work here presented includes the design criteria for the PC prototype, the synthesis of <span class="hlt">a</span> series of candidates, the characterization of the PC:βCD complexes, the determination of the selectivity profiles toward <span class="hlt">a</span> panel of commercial and human lysosomal glycosidases, the evaluation of the chaperoning activity in type 1 (non-neuronopathic), type 2 (acute neuronopathic), and type 3 (adult neuronopathic) GD fibroblasts, the confirmation of the rescuing mechanism by immunolabeling, and the analysis of the PC:GCase binding mode by docking experiments.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/27334416','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/27334416"><span>Enantioresolution in electrokinetic chromatography-complete filling technique using sulfated gamma-<span class="hlt">cyclodextrin</span>. Software-free topological anticipation.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Escuder-Gilabert, Laura; Martín-Biosca, Yolanda; Medina-Hernández, María José; Sagrado, Salvador</p> <p>2016-10-07</p> <p>Few papers have tried to predict the resolution ability of chiral selectors in capillary electrophoresis for the separation of the enantiomers of chiral <span class="hlt">compounds</span>. In <span class="hlt">a</span> previous work, we have used molecular information available on-line to establish enantioresolution levels of basic <span class="hlt">compounds</span> using highly sulfated β-CD (HS-β-CD) as chiral selector in electrokinetic chromatography-complete filling technique (EKC-CFT). The present study is <span class="hlt">a</span> continuation of this previous work, introducing some novelties. In this work, the ability of sulfated γ-<span class="hlt">cyclodextrin</span> (S-γ-CD) as chiral selector in EKC-CFT is modelled for the first time. Thirty-three structurally unrelated cationic and neutral <span class="hlt">compounds</span> (drugs and pesticides) are studied. Categorical enantioresolution levels (RsC, 0 or 1) are assigned from experimental enantioresolution values obtained at different S-γ-CD concentrations. Novel topological parameters connected to the chiral carbon (C * -parameters) are introduced. Four C * -parameters and <span class="hlt">a</span> topological parameter of the whole molecule (aromatic atom count) are the most important variables according to <span class="hlt">a</span> discriminant partial least squares-variable selection process. It suggests the preponderance of the topology adjacent to the chiral carbon to anticipate the RsC levels. <span class="hlt">A</span> software-free anticipation protocol for new molecules is proposed. Over the current set of molecules evaluated, 100% of correct anticipations (resolved and non-resolved <span class="hlt">compounds</span>) are obtained, while anticipation of some <span class="hlt">compounds</span> remains undetermined. <span class="hlt">A</span> criterion is introduced to alert on <span class="hlt">compounds</span> which should not be anticipated. Copyright © 2016 Elsevier B.V. All rights reserved.</p> </li> <li> <p><a target="_blank" onclick="trackOutboundLink('https://www.ncbi.nlm.nih.gov/pubmed/17393288','PUBMED'); return false;" href="https://www.ncbi.nlm.nih.gov/pubmed/17393288"><span>Hydroxypropyl-beta-<span class="hlt">cyclodextrin</span> enhanced determination for the Vitamin B12 by fluorescence quenching method.</span></a></p> <p><a target="_blank" href="https://www.ncbi.nlm.nih.gov/entrez/query.fcgi?DB=pubmed">PubMed</a></p> <p>Sun, Jing; Zhu, Xiashi; Wu, Ming</p> <p>2007-05-01</p> <p><span class="hlt">A</span> novel fluorescence quenching method for the determination of Vitamin B12(VB12) had been developed. It was based on that the fluorescence intensity of erythrosine sodium(ES) could be enhanced by Hydroxypropyl-beta-<span class="hlt">cyclodextrin</span>(HP-beta-CD) due to the formation of <span class="hlt">inclusion</span> complex (HP-beta-CD-ES), while the fluorescence intensity of HP-beta-CD-ES was diminished after adding VB12 into the system, and there was <span class="hlt">a</span> linear relationship between the fluorescence quenching value of the system (DeltaF) and the concentration of VB12 (c). The mechanism of the determination of VB12 was discussed. The results showed that under the optimal conditions, the linear range of calibration curve for the determination of VB12 was 0.0 approximately 2.1 x 10(-5) mol/L, and the detection limit was 1.8 x 10(-7) mol/ L. It could be satisfactorily applied to the determination of VB12 in injections.</p> </li> </ol> <div class="pull-right"> <ul class="pagination"> <li><a href="#" onclick='return showDiv("page_1");'>«</a></li> <li><a href="#" onclick='return showDiv("page_21");'>21</a></li> <li><a href="#" onclick='return showDiv("page_22");'>22</a></li> <li><a href="#" onclick='return showDiv("page_23");'>23</a></li> <li><a href="#" onclick='return showDiv("page_24");'>24</a></li> <li class="active"><span>25</span></li> <li><a href="#" onclick='return showDiv("page_25");'>»</a></li> </ul> </div> </div><!-- col-sm-12 --> </div><!-- row --> </div><!-- page_25 --> <div class="footer-extlink text-muted" style="margin-bottom:1rem; text-align:center;">Some links on this page may take you to non-federal websites. 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