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Sample records for 10-bis 2-naphthyl anthracene

  1. White organic light-emitting diodes with 9, 10-bis (2-naphthyl) anthracene

    NASA Astrophysics Data System (ADS)

    Guan, Yunxia; Niu, Lianbin

    2009-03-01

    White organic light-emitting diodes were fabricated by 9, 10-bis (2-naphthyl) anthracene (ADN) doped with Rubrene with a structure of ITO/copper phthalocyanine (CuPc) / NPB /ADN: Rubrene /Alq3 /CsF/Mg:Ag/Ag. Multilayer organic devices using AND and Rubrene as an emitting layer produced white emissions with good chromaticity and luminous efficiency as high as 5.93 cd/A. This performance can be explained by Förster energy transfer from the blue-emitting host to the orange-emitting dopant.

  2. Enhanced Translational Diffusion of 9,10-bis(phenylethynyl)anthracene (BPEA) in Polystyrene

    NASA Astrophysics Data System (ADS)

    Wang, Chia-Ying; Ediger, M. D.

    1997-03-01

    We have used a holographic fluorescence recovery after photobleaching (FRAP) techanique to measure translational diffusion coefficients of tracer levels of 9,10-bis(phenylethynyl)anthracene (BPEA) in polystyrene. Values for the diffusion coefficient DT ranged from 10-8 to 10-14 cm^2/sec over the temperature range T_g+90K to Tg (Tg = 373K). DT has a considerably weaker temperature dependence than matrix viscosity η. In contrast, the rotational correlation time τ c for BPEA has the same temperature dependence as η. At T_g, translational diffusion of BPEA is enhanced over rotation by 2.4 decades. These results support the idea that spatially heterogeneous dynamics are responsible for enhanced translation and are an important feature of dynamics at T_g.

  3. Improved efficiency for green and red emitting electroluminescent devices using the same cohost composed of 9,10-di(2-naphthyl) anthracene and tris-(8-hydroxyquinolinato) aluminum

    NASA Astrophysics Data System (ADS)

    Zhu, Jianzhuo; Li, Wenlian; Chu, Bei; Yang, Dongfang; Zhang, Guang; Liu, Huihui; Chen, Yiren; Su, Zisheng; Wang, Junbo; Wu, Shuanghong

    2009-12-01

    We demonstrate highly efficient green and red fluorescence dyes-doped electroluminescent devices using cohost strategy. The cohost system is composed of tris-(8-hydroxyquinolinato) aluminum (Alq) and 9,10-di(2-naphthyl) anthracene (ADN). The maximum current efficiencies are increased by 54% and 104% for green and red devices by optimizing the ratio between ADN and Alq in the cohost compared to the conventional Alq single-host devices, respectively. We attribute the improvement of efficiencies to balanced hole and electron injection into the emitting layer, the enlarged width of recombination region and the multiple emission processes.

  4. Improved efficiency in organic light-emitting devices with tris-(8-hydroxyquinoline) aluminium doped 9,10-di(2-naphthyl) anthracene emission layer

    NASA Astrophysics Data System (ADS)

    Yuan, Yongbo; Lian, Jiarong; Li, Shuang; Zhou, Xiang

    2008-11-01

    Organic light-emitting devices with tris-(8-hydroxyquinoline) aluminium (Alq3) doped 9,10-di(2-naphthyl) anthracene (ADN) as the emission layer (EML) have been fabricated. These devices exhibit efficient electroluminescence (EL) originated from the Alq3 as the mass ratio of Alq3 to ADN was varied from 1 to 50%. The devices with an optimal Alq3 mass ratio of 10 wt% showed a peak EL efficiency and an external quantum efficiency of 9.1 cd A-1 and 2.7% at a luminance of 1371 cd m-2, which is improved by a factor of 2.2 compared with 4.1 cd A-1 and 1.2% at a luminance of 3267 cd m-2 for conventional devices with the neat Alq3 as the EML.

  5. The role of charge-transfer integral in determining and engineering the carrier mobilities of 9,10-di(2-naphthyl)anthracene compounds

    NASA Astrophysics Data System (ADS)

    Tse, S. C.; So, S. K.; Yeung, M. Y.; Lo, C. F.; Wen, S. W.; Chen, C. H.

    2006-05-01

    The charge transporting properties of t-butylated 9,10-di(2-naphthyl)anthracene (ADN) compounds have been investigated experimentally and computationally in relation to their molecular structures. The ADN compounds are found to be ambipolar with both electron and hole mobilities in the range of 1-4 × 10 -7 cm 2 V -1 s -1 (electric field 0.5-0.8 MV/cm). As the degree of t-butylation increases, the carrier mobility decreases progressively. The mobility reduction was examined by Marcus theory of reorganization energies. All ADN compounds possess similar reorganization energies of ˜0.3 eV. The reduction of carrier mobilities with increasing t-butylation can be attributed to a decrease in the charge-transfer integral or the wavefunction overlap.

  6. Electronic states of the fluorophore 9,10-bis(phenylethynyl)anthracene (BPEA). A synchrotron radiation linear dichroism investigation

    NASA Astrophysics Data System (ADS)

    Thulstrup, Peter W.; Jones, Nykola C.; Hoffmann, Søren V.; Spanget-Larsen, Jens

    2013-02-01

    The electronic transitions of 9,10-bis(phenylethynyl)anthracene (BPEA) were investigated by synchrotron radiation linear dichroism (SRLD) spectroscopy in the range 20 000-58 000 cm-1 (500-170 nm) on molecular samples aligned in stretched polyethylene. The investigation was supported by variable temperature spectroscopy and by quantum chemical calculations in the LCOAO and TD-DFT models. The combined experimental and theoretical evidence leads to characterization of several previously unobserved transitions and provides a revised polarization analysis of the visible absorption band of BPEA.

  7. Highly Efficient and Stable Red Organic Light-Emitting Devices Using 9,10-Di(2-naphthyl)anthracene as the Host Material

    NASA Astrophysics Data System (ADS)

    Tang, Hao; Li, Ying; Wang, Xiuru; Wang, Wengen; Sun, Runguang

    2007-04-01

    We present red organic light-emitting devices (OLEDs) with high efficiency and stability based on a wide band gap host material 9,10-di(2-naphthyl)anthracene (ADN). In these devices, N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'-diamine (NPB) and tris(8-hydroxy-quinoline) aluminum (Alq) were used as hole and electron transport layers, respectively. Coumarin 6 (C6) and 4-(dicyano-methylene)-2-t-butyl-6-(1,1,7,7-tetramethyl-julolidyl-9-enyl)-4H-pyran (DCJTB) were co-doped into the ADN emitting layer. Utilizing the two-step energy transfer from ADN to C6 and then from C6 to DCJTB, we achieved pure red organic light-emitting devices, which showed improved optical and electrical characteristics. Compared with devices where the emitting layer is composed of Alq and DCJTB, the emission efficiency and stability of the co-doped ADN-based devices are greatly improved and the turn-on voltage is also decreased. The co-doping technique provides a promising way to utilize wide band gap materials as the host to make red OLEDs, which will be useful in improving the EL performance of devices and simplifying the process of fabricating full-color OLEDs.

  8. Solution-processed high-performance flexible 9, 10-bis(phenylethynyl)anthracene organic single-crystal transistor and ring oscillator

    NASA Astrophysics Data System (ADS)

    Cai, Xiaozhou; Ji, Deyang; Jiang, Lang; Zhao, Guangyao; Tan, Jiahui; Tian, Guofeng; Li, Jingze; Hu, Wenping

    2014-02-01

    Organic semiconductor of 9, 10-bis(phenylethynyl)anthracene (BPEA) single crystal ribbon with ultra-long length has been prepared by solution drop casting method, where the growth direction was controlled with the seed crystal. The BPEA single crystal ribbon based field-effect transistors show high hole mobility up to 3.2 cm2/V.s, and the inverters exhibited the highest gain of 92. The complex device such as 5-stage ring oscillator consisting of 10 transistors was also constructed on a single crystal ribbon. This straightforward methodology was applied to fabricate plastic transistors on the flexible substrate, showing high performance even after repeatedly bending of 300 times.

  9. Effects of Supramolecular Encapsulation on Photophysics and Photostability of a 9,10-Bis(arylethynyl)anthracene-Based Chromophore Revealed by Single-Molecule Fluorescence Spectroscopy.

    PubMed

    Mitsui, Masaaki; Higashi, Koji; Hirumi, Yohei; Kobayashi, Kenji

    2016-10-18

    The effects of supramolecular encapsulation on the photophysics and photostability of a highly fluorescent dimeric derivative of 2,6-diacetoxy-9,10-bis(arylethynyl)anthracene (G2) were investigated by single-molecule fluorescence spectroscopy (SMFS). The fluorescence properties of free-G2 and its self-assembled boronic ester encapsulation complex, G2@(Cap)2, were compared in solution and a glassy polymer film. The fluorescence spectral characteristics and theoretical calculations suggest that the environment affects the excited-state conformation and subsequent fluorescence emission of G2@(Cap)2. In particular, in the liquid and polymer environments, G2@(Cap)2 emits a fluorescence photon in the planar and twist conformation, respectively, whereas the fluorescence-emitting conformation of free-G2 is planar in both environments. The luminous conformation differences between free-G2 and G2@(Cap)2 in polymer are reflected in the intersystem crossing (ISC) parameters (the ISC quantum yield and triplet lifetime), as determined by fluorescence autocorrelation analysis. The photobleaching yield revealed a 3-fold enhancement in the photostability of encapsulated G2 (relative to free-G2). Under the SMFS measurement conditions, the photostability of the encapsulation complex was independent of the guest's photostability and appeared to be dominated by the thermal stability of the Cap host molecule.

  10. First steps in photophysics. I. Fluorescence yield and radiative rate coefficient of 9,10-bis(phenylethynyl)anthracene in paraffins.

    PubMed

    Demeter, Attila

    2014-10-30

    The fluorescence quantum yield of 9,10-bis(phenylethynyl)anthracene (BPEA) is almost unity in every examined solvent. Using different hydrocarbons, one can make a convenient and sufficiently accurate experimental test for determination of the extent of the refractive index correction needed in fluorescence quantum yield determination on a given fluorometer. By comparison of the measurements in n-pentane-cis-decaline or n-hexane-toluene solvent pairs, the requirement of the n(2) correction is confirmed for most of the fluorometers; however, for one of the examined pieces of equipment the necessary correction proved to be slightly lower. By excited state's lifetime measurements, the refractive index dependence of the fluorescence rate coefficient was reexamined. At 25 °C for BPEA the relationship is in agreement with Bakhshiev's prediction: the experimentally determined exponent of n in the rate coefficient deriving equation is around 1.32 using different paraffins as solvents. The negative temperature coefficient of the radiative rate in part originates from the temperature dependence of the refractive index, while also a small intrinsic contribution has been found.

  11. Relationship between molecular stacking and optical properties of 9,10-bis((4-N,N-dialkylamino)styryl) anthracene crystals: the cooperation of excitonic and dipolar coupling.

    PubMed

    Li, Feng; Gao, Na; Xu, Hai; Liu, Wei; Shang, Hui; Yang, Wenjun; Zhang, Ming

    2014-08-04

    Five 9,10-bis((4-N,N-dialkylamino)styryl) anthracene derivatives (DSA-C1-DSA-C7) with different length alkyl chains were synthesized. They showed the same color in dilute solutions but different colors in crystals. The absorption, photoluminescence, and fluorescence decay indicate that there exist both excitonic and dipolar coupling in crystals of DSA-C1-DSA-C7. X-ray crystallographic analysis revealed that all the crystals belong to the triclinic space group P1 with one molecule per unit cell and that the molecules in every crystal have the identical orientation. This offers ideal samples to investigate the impact of the molecular stacking on the optical properties of the crystals. For the first time, the cooperation of excitonic and dipolar coupling has been comprehensively studied, and the contribution to the spectral shift from the excitonic and dipolar couplings quantitatively obtained. The experiments of amplified spontaneous emission (ASE) together with measurements of the quantum efficiency further confirmed this interpretation. The results suggest that the excitonic and dipolar couplings between the adjacent molecules are both important and jointly induce the spectral shifts of the crystals.

  12. Studies of the degradation mechanism of organic light-emitting diodes based on tris(8-quinolinolate)aluminum Alq and 2-tert-butyl-9,10-di(2-naphthyl)anthracene TBADN

    NASA Astrophysics Data System (ADS)

    Jarikov, Viktor V.; Kondakov, Denis Y.

    2009-02-01

    Previously, radical cation of tris(8-quinolinolate)aluminum (Alq•+) has been associated with the instability of Alq films subjected to holes-only electrical current. Yet, the questions remain (i) whether Alq•+ is the primary source of the intrinsic degradation of bipolar organic light-emitting diodes (OLEDs) based on Alq, (ii) whether Alq•+ reactions result in deep charge traps in holes-only devices as found in bipolar counterparts, and (iii) whether radical cations can be a common source of degradation of OLEDs irrespective of materials. With regards to generality of hole-current-related degradation, it is interesting to examine the behavior of 9,10-diarylanthracenes (DAAs)—the practically important class of blue-fluorescing light-emitting-layer hosts. These questions prompted our comparative study of the effects of unipolar currents in Alq and 2-t-butyl-9,10-di(2-naphthyl)anthracene (TBADN), which was chosen as a representative material of the DAA class. First, we identified device structures allowing for rigorous and stable unipolar conduction. Interestingly, even in pristine holes-only devices, our voltammetric measurements indicated that Alq contains a substantial density of deep hole traps (far deeper than what can be explained by energetic disorder), which can be charged by passing holes-only current and seemingly discharged by exposure to white light. As for aged holes-only Alq devices, they exhibited symptoms qualitatively matching those of aged bipolar Alq devices, viz., photoluminescence (PL) loss, transition voltage (V0) rise, and drive voltage (Vd) rise. Notably, PL and V0 are linearly correlated in both holes-only and bipolar devices, which reinforces the supposed link between Alq•+ and the degradation in both types of devices. Yet, there are indications the Alq•+ instability may not be the only degradation pathway in bipolar devices. Even though our observations for holes-only Alq devices agree qualitatively with previously reported ones

  13. Self-Assembly of 9,10-Bis(phenylethynyl)anthracene (BPEA) Derivatives: Influence of pi-pi and Hydrogen Bonding Interactions on Aggregate Morphology and Self-Assembly Mechanism.

    PubMed

    Lübtow, Michael; Helmers, Ingo; Stepanenko, Vladimir; Albuquerque, Rodrigo Queiroz; Marder, Todd Benjamin; Fernandez, Gustavo

    2017-02-10

    9,10-Bis(phenylethynyl)anthracenes (BPEAs) are an important class of dyes with various applications including chemiluminescent emitters, materials for photon upconversion and for optoelectronic devices. Some of these applications require control over the packing modes of the active molecules within the active layer, which can be effected by bottom-up self-assembly. Studies aimed at controllling the molecular organization of BPEAs have primarily focused on bulk or liquid crystal materials, while in-depth investigations of BPEA-based assemblies in solution remain elusive. In this article, we report the self-assembly of two new BPEA derivatives with hydrophobic side chains, one of them featuring amide functional groups (2) and the other one lacking them (1). Comparison of the self-assembly behaviour in solution of both systems via spectroscopic (UV/Vis, fluorescence and NMR), microscopic (AFM) and theoretical (PM6) studies reveals the crucial role of the amide groups in controlling the self-assembly. While for both systems the formation of H-type face-to-face pi-stacks is proposed, the the interplay of pi-stacking and H-bonding is responsible of driving the formation of 1D stacks and increasing the binding constant almost three orders of magnitude. Our findings show that H-bonding is a prerequisite to create ordered BPEA assemblies in solution.

  14. Anthracene

    Integrated Risk Information System (IRIS)

    Anthracene ; CASRN 120 - 12 - 7 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Effect

  15. Electronic properties of anthracene derivatives for blue light emitting electroluminescent layers in organic light emitting diodes: a density functional theory study.

    PubMed

    Raghunath, P; Reddy, M Ananth; Gouri, C; Bhanuprakash, K; Rao, V Jayathirtha

    2006-01-26

    Molecular level parameters are investigated computationally to understand the factors that are responsible for the higher efficiency in derivatives of 9,10-bis(1-naphthyl)anthracene (alpha-ADN), 9,10-bis(2-naphthyl)anthracene (beta-ADN), their tetramethyl derivatives (alpha,beta-TMADN) and the t-Bu derivative (beta-TBADN) as blue light emitting electroluminescent (EL) layers in organic light emitting diodes (OLEDs). DFT studies at the B3LYP/6-31G(d,p) level have been carried out on the substituted anthracenes. The absorption spectra are simulated using time dependent DFT methods (TD-DFT) whereas the emission spectra are approximated by optimizing the excited state by HF/CI-Singles and then carrying out the vertical CI calculations by the TD-DFT method. The reorganization energy for estimating the hole and electron transport is calculated. The transfer integrals between parallely stacked molecules in the bulk state are estimated by calculating the electronic splitting. The substituted anthracenes are compared with unsubstituted anthracene and yet untested 9,10-dianthrylanthracene (TANTH). A larger and slower buildup of the electrons and holes in the EL layer, due to the higher reorganization energy and smaller electronic coupling between the adjacent molecules could lead to an increase in hole-electron recombination in the layer and thus increase the efficiency.

  16. Quantum yield in blue-emitting anthracene derivatives: vibronic coupling density and transition dipole moment density.

    PubMed

    Uejima, Motoyuki; Sato, Tohru; Yokoyama, Daisuke; Tanaka, Kazuyoshi; Park, Jong-Wook

    2014-07-21

    A theoretical design principle for enhancement of the quantum yield of light-emitting molecules is desired. For the establishment of the principle, we focused on the S1 states of blue-emitting anthracene derivatives: 2-methyl-9,10-di(2'-naphthyl)anthracene (MADN), 4,9,10-bis(3',5'-diphenylphenyl)anthracene (MAM), 9-(3',5'-diphenylphenyl)-10-(3'',5''-diphenylbiphenyl-4''-yl) anthracene (MAT), and 9,10-bis(3''',5'''-diphenylbiphenyl-4'-yl) anthracene (TAT) [Kim et al., J. Mater. Chem., 2008, 18, 3376]. The vibronic coupling constants and transition dipole moments were calculated and analyzed by using the concepts of vibronic coupling density (VCD) and transition dipole moment density (TDMD), respectively. It is found that the driving force of the internal conversions and vibrational relaxations originate mainly from the anthracenylene group. On the other hand, fluorescence enhancement results from the large torsional distortion of the side groups in the S1 state. The torsional distortion is caused by the diagonal vibronic coupling for the lowest-frequency mode in the Franck-Condon (FC) S1 state, which originates from a small portion of the electron density difference on the side groups. These findings lead to the following design principles for anthracene derivatives with a high quantum yield: (1) reduction in the electron density difference and overlap density between the S0 and S1 states in the anthracenylene group to suppress vibrational relaxation and radiationless transitions, respectively; (2) increase in the overlap density in the side group to enhance the fluorescence.

  17. Design, Conformation, and Crystallography of 2-Naphthyl Phenyl Ethers as Potent Anti-HIV Agents

    SciTech Connect

    Lee, Won-Gil; Chan, Albert H.; Spasov, Krasimir A.; Anderson, Karen S.; Jorgensen, William L.

    2016-12-08

    Catechol diethers that incorporate a 7-cyano-2-naphthyl substituent are reported as non-nucleoside inhibitors of HIV-1 reverse transcriptase (NNRTIs). Many of the compounds have 1–10 nM potencies toward wild-type HIV-1. An interesting conformational effect allows two unique conformers for the naphthyl group in complexes with HIV-RT. X-ray crystal structures for 4a and 4f illustrate the alternatives.

  18. Photoactivatable anthracenes.

    PubMed

    Thapaliya, Ek Raj; Captain, Burjor; Raymo, Françisco M

    2014-05-02

    Fifteen substituted maleimide cycloadducts of anthracene derivatives were synthesized in one or two steps from available precursors in yields ranging from 32 to 63%. They differ in the nature of the group on the maleimide nitrogen atom and of the substituents on the anthracene platform. In all instances, the introduction of a maleimide bridge across positions 9 and 10 of the anthracene skeleton isolates electronically its peripheral phenylene rings and suppresses its characteristic fluorescence. The cycloadducts with a 4-(dimethylamino)phenyl group on the maleimide nitrogen atom undergo retro-cycloaddition upon ultraviolet illumination with quantum yields ranging from 0.001 to 0.01. This structural transformation restores the aromatic character of the central ring of the oligoacene chromophore and activates its emission with fluorescence quantum yields ranging from 0.07 to 0.85. Thus, this particular choice of building blocks for the construction of photoresponsive compounds can translate into viable operating principles for fluorescence activation and, ultimately, lead to the realization of valuable photoactivatable fluorophores for imaging applications.

  19. Tetrahydro-2-naphthyl and 2-Indanyl Triazolopyrimidines Targeting Plasmodium falciparum Dihydroorotate Dehydrogenase Display Potent and Selective Antimalarial Activity

    PubMed Central

    2016-01-01

    Malaria persists as one of the most devastating global infectious diseases. The pyrimidine biosynthetic enzyme dihydroorotate dehydrogenase (DHODH) has been identified as a new malaria drug target, and a triazolopyrimidine-based DHODH inhibitor 1 (DSM265) is in clinical development. We sought to identify compounds with higher potency against Plasmodium DHODH while showing greater selectivity toward animal DHODHs. Herein we describe a series of novel triazolopyrimidines wherein the p-SF5-aniline was replaced with substituted 1,2,3,4-tetrahydro-2-naphthyl or 2-indanyl amines. These compounds showed strong species selectivity, and several highly potent tetrahydro-2-naphthyl derivatives were identified. Compounds with halogen substitutions displayed sustained plasma levels after oral dosing in rodents leading to efficacy in the P. falciparum SCID mouse malaria model. These data suggest that tetrahydro-2-naphthyl derivatives have the potential to be efficacious for the treatment of malaria, but due to higher metabolic clearance than 1, they most likely would need to be part of a multidose regimen. PMID:27127993

  20. Photophysical properties of 9,10-disubstituted anthracene derivatives in solution and films.

    PubMed

    Ribierre, J C; Ruseckas, A; Cavaye, H; Barcena, H S; Burn, P L; Samuel, I D W

    2011-07-07

    We have carried out absorption, time-resolved fluorescence, and fluorescence quantum yield measurements of four new soluble anthracene derivatives. They show natural radiative lifetimes in the range of 2.5-4.4 ns, which is 5-10 times shorter than those reported for unsubstituted anthracene. The 9,10-bis(phenylethynyl)anthracene (BPEA) derivatives show the largest fluorescence transition dipoles, which is attributed to extended π-conjugation between anthracene and phenyls through acetylene linkages. Spin-cast films of the BPEA derivatives show strong fluorescence quenching by weakly emitting low energy excitations, which is attributed to excimer-like traps. Quenching is significantly reduced when bulky dendrons are attached so that they give maximum coverage of the emitting chromophore and prevent their aggregation. The results show that anthracene derivatives can be developed into efficient solution-processable fluorescent emitters for the blue and green spectral regions.

  1. Synthesis and structure-activity relationships of N-{1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide derivatives as novel CCR3 antagonists.

    PubMed

    Sato, Ippei; Morihira, Koichiro; Inami, Hiroshi; Kubota, Hirokazu; Morokata, Tatsuaki; Suzuki, Keiko; Hamada, Noritaka; Iura, Yosuke; Nitta, Aiko; Imaoka, Takayuki; Takahashi, Toshiya; Takeuchi, Makoto; Ohta, Mitsuaki; Tsukamoto, Shin-ichi

    2008-01-01

    A novel class of potent CCR3 receptor antagonists were designed and synthesized starting from N-{1-[(6-fluoro-2-naphthyl)methyl]piperidin-4-yl}benzamide (1),which was found by subjecting our chemical library to high throughput screening (HTS). The CCR3 inhibitory activity of the synthesized compounds against eotaxin-induced Ca(2+) influx was evaluated using CCR3-expressing preB cells. Systematic chemical modifications of 1 revealed that the 6-fluoro-2-naphthylmethyl moiety was essential for CCR3 inhibitory activity in this new series of CCR3 antagonists. Further structural modifications of the benzamide and piperidine moieties of 1 led to the identification of exo-N-{8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3- yl}biphenyl-2-carboxamide [corrected] (31) as a potent CCR3 antagonist with an IC(50) value of 0.020 microM.

  2. Electron-rich anthracene semiconductors containing triarylamine for solution-processed small-molecule organic solar cells.

    PubMed

    Choi, Hyeju; Ko, Haye Min; Cho, Nara; Song, Kihyung; Lee, Jae Kwan; Ko, Jaejung

    2012-10-01

    New electron-rich anthracene derivatives containing triarylamine hole stabilizers, 2,6-bis[5,5'-bis(N,N'-diphenylaniline)-2,2'-bithiophen-5-yl]-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBT-TPA) and 2,6-bis(5,5'-bis{4-[bis(9,9-dimethyl-9H-fluoren-2-yl)amino]phenyl}-2,2'-bithiophen-5-yl)-9,10-bis-[(triisopropylsilyl)ethynyl]anthracene (TIPSAntBT-bisDMFA), linked with π-conjugated bithiophene bridges, were synthesized and their photovoltaic characteristics were investigated in solution-processed small-molecule organic solar cells (SMOSCs). These new materials exhibited superior intramolecular charge transfer from triarylamine to anthracene, leading to a more electron-rich anthracene core that facilitated electron transfer into phenyl-C(61)-butyric acid methyl ester. Compared with TIPSAntBT and triarylamine, these materials show a threefold improvement in hole-transporting properties and better photovoltaic performance in solution-processed SMOSCs, with the best power conversion efficiency being 2.96 % at a high open-circuit voltage of 0.85 V.

  3. Benz[a]anthracene

    Integrated Risk Information System (IRIS)

    Benz [ a ] anthracene ; CASRN 56 - 55 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinoge

  4. Antimicrobial screening and one-pot synthesis of 4-(substituted-anilinomethyl)-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives

    PubMed Central

    Goel, Neelima; Drabu, Sushma; Afzal, Obaid; Bawa, Sandhya

    2014-01-01

    Aim: Synthesis of series of 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a–4k) and their in vitro antifungal and antibacterial screening. Materials and Methods: A series of compounds (4a–4k) was synthesized through direct reductive amination of 3-(naphthalen-2-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde with various substituted aromatic amines using NaBH4 in the presence of I2 as reducing agent. The reaction was carried out in anhydrous methanol under neutral conditions at room temperature. The structures of synthesized compounds (4a–4k) were established on the basis of IR, 1H and 13C-NMR, and mass spectral data. Results: All 4-(substituted-anilinomethyl-3-(2-naphthyl)-1-phenyl-1H-pyrazole derivatives (4a–4k) were tested in vitro for antifungal and antibacterial activities against different fungal and bacterial strains. Most of the compounds exhibited considerable antifungal activity, but poor antibacterial activity against the test strains. Conclusion: In the series compound 4e, 4g, 4j, and 4k, showed excellent antifungal activity against the fungal strain Aspergillus niger (MTCC) 281 and Aspergillus flavus MTCC 277 (% inhibition in the range of 47.7–58.9). PMID:25400408

  5. Synthesis and characterization of an anthracene-based low band gap polymer for photovoltaic devices.

    PubMed

    Jung, In Hwan; Kim, Hoyeon; Lee, Wonho; Jung, Byung Jun; Woo, Han Young; Yoo, Seunghyup; Shim, Hong-Ku

    2014-08-01

    We have synthesized an anthracene-based conjugated polymer, poly[(9,10-bis(oct-1-ynyl)anthracene)-alt-(5,6-bis(octyloxy)-4,7-bis(thiophen-2-yl)benzo-[c][1,2,5]-thiadiazole)] (PANTBT), for application in organic photovoltaic devices. It exhibited a number average molecular weight of 14,300 g/mol and was fairly soluble in chlorinated organic solvents due to flexible octynyl- and octyloxy side chains on the anthracene and benzothiadiazole moieties. PANTBT showed absorption covering 300-660 nm. Through the bond alternation between the electron-sufficient anthracene (and thiophene) and electron-deficient benzothiadiazole units, a band gap of PANTBT was decreased to 1.89 eV, showing a deep HOMO level of -5.31 eV. As a result, PANTBT exhibited promising photovoltaic properties with a PCE value of 1.90% (VOC = 0.77 V, JSC = -6.50 mA/cm2, FF = 0.38) upon blending with PC71, BM under AM 1.5G.

  6. Photoluminescence behavior of europium (III) complexes containing 1-(4-tert-butylphenyl)-3-(2-naphthyl)-propane-1,3-dione ligand.

    PubMed

    Wang, Dunjia; Zheng, Chunyang; Fan, Ling; Hu, Yanjun; Zheng, Jing

    2014-01-03

    Three novel europium complexes with 1-(4-tert-butylphenyl)-3-(2-naphthyl)-propane-1,3-dione (TNPD) and 2,2-dipyridine (Bipy) or 1,10-phenan-throline (Phen) were synthesized and confirmed by FT-IR, (1)H NMR, UV-vis absorption and elemental analysis. Photoluminescence behavior of complexes Eu(TNPD)3, Eu(TNPD)3·Bipy and Eu(TNPD)3·Phen were investigated in detail. Their emission spectra exhibited the characteristic emission bands that arise from the (5)D0→(7)FJ (J=0-4) transitions of the europium ion in solid state. Meanwhile, the results of their lifetime decay curves indicated that only one chemical environment existed around the europium ion. The intrinsic luminescence quantum efficiency (η) and the experimental intensity parameters (Ωt) of europium complexes were determined according to the emission spectra and luminescence decay curves in solid state. The complex Eu(TNPD)3·Phen showed much longer lifetime (τ) and higher luminescence quantum efficiency (η) than complexes Eu(TNPD)3 and Eu(TNPD)3·Bipy.

  7. Design and synthesis of 6-fluoro-2-naphthyl derivatives as novel CCR3 antagonists with reduced CYP2D6 inhibition.

    PubMed

    Sato, Ippei; Morihira, Koichiro; Inami, Hiroshi; Kubota, Hirokazu; Morokata, Tatsuaki; Suzuki, Keiko; Iura, Yosuke; Nitta, Aiko; Imaoka, Takayuki; Takahashi, Toshiya; Takeuchi, Makoto; Ohta, Mitsuaki; Tsukamoto, Shin-Ichi

    2008-09-15

    In our previous study on discovering novel types of CCR3 antagonists, we found a fluoronaphthalene derivative (1) that exhibited potent CCR3 inhibitory activity with an IC(50) value of 20 nM. However, compound 1 also inhibited human cytochrome P450 2D6 (CYP2D6) with an IC(50) value of 400 nM. In order to reduce its CYP2D6 inhibitory activity, we performed further systematic structural modifications on 1. In particular, we focused on reducing the number of lipophilic moieties in the biphenyl part of 1, using ClogD(7.4) values as the reference index of lipophilicity. This research led to the identification of N-{(3-exo)-8-[(6-fluoro-2-naphthyl)methyl]-8-azabicyclo[3.2.1]oct-3-yl}-3-(piperidin-1-ylcarbonyl)isonicotinamide 1-oxide (30) which showed comparable CCR3 inhibitory activity (IC(50)=23 nM) with much reduced CYP2D6 inhibitory activity (IC(50)=29,000 nM) compared with 1.

  8. Evaluation of structure-reactivity descriptors and biological activity spectra of 4-(6-methoxy-2-naphthyl)-2-butanone using spectroscopic techniques

    NASA Astrophysics Data System (ADS)

    Agrawal, Megha; Deval, Vipin; Gupta, Archana; Sangala, Bagvanth Reddy; Prabhu, S. S.

    2016-10-01

    The structure and several spectroscopic features along with reactivity parameters of the compound 4-(6-methoxy-2-naphthyl)-2-butanone (Nabumetone) have been studied using experimental techniques and tools derived from quantum chemical calculations. Structure optimization is followed by force field calculations based on density functional theory (DFT) at the B3LYP/6-311++G(d,p) level of theory. The vibrational spectra have been interpreted with the aid of normal coordinate analysis. UV-visible spectrum and the effect of solvent have been discussed. The electronic properties such as HOMO and LUMO energies have been determined by TD-DFT approach. In order to understand various aspects of pharmacological sciences several new chemical reactivity descriptors - chemical potential, global hardness and electrophilicity have been evaluated. Local reactivity descriptors - Fukui functions and local softnesses have also been calculated to find out the reactive sites within molecule. Aqueous solubility and lipophilicity have been calculated which are crucial for estimating transport properties of organic molecules in drug development. Estimation of biological effects, toxic/side effects has been made on the basis of prediction of activity spectra for substances (PASS) prediction results and their analysis by Pharma Expert software. Using the THz-TDS technique, the frequency-dependent absorptions of NBM have been measured in the frequency range up to 3 THz.

  9. Detection of carbohydrates using new labeling reagent 1-(2-naphthyl)-3-methyl-5-pyrazolone by capillary zone electrophoresis with absorbance (UV).

    PubMed

    You, Jinmao; Sheng, Xiao; Ding, Chenxu; Sun, Zhiwei; Suo, Yourui; Wang, Honglun; Li, Yulin

    2008-02-18

    A novel labeling reagent 1-(2-naphthyl)-3-methyl-5-pyrazolone (NMP) coupled with capillary electrophoresis (CE) with DAD detection for the determination of carbohydrates has been developed. The chromophore in the 1-phenyl-3-methyl-5-pyrazolone (PMP) reagent is replaced by naphthyl functional group, which results in a reagent with very high molar absorptivity (epsilon251 nm = 5.58 x 10(4) L mol(-1) cm(-1)). This permits NMP-labeled carbohydrates to be detected with UV absorbance in standard 50-mum-i.d. fused silica capillaries by zone electrophoresis. In this mode, nanomolar concentrations of detection limits are obtained. The method for the derivatization of carbohydrates with NMP is simplified. The derivatization reaction is rapid and mild in the presence of ammonia catalyst without further transfer steps. Nine monosaccharide derivatives such as mannose, galacturonic acid, glucuronic acid, rhamnose, glucose, galactose, xylose, arabinose and fucose can successfully be detected in CE mode. Good reproducibility can be obtained with relative standard deviation (R.S.D.) values of the migration times and peak area, respectively, from 0.44 to 0.48 and from 3.2 to 4.8. Furthermore, the developed method has been successfully applied to the analysis of carbohydrates in the hydrolyzed rape bee pollen samples.

  10. Manganese(II)-azido/thiocyanato complexes of naphthylazoimidazoles: X-ray structures of Mn(β-NaiEt) 2(X) 2 (β-NaiEt = 1-ethyl-2-(naphthyl-β-azo)imidazole; X=N3-, NCS -)

    NASA Astrophysics Data System (ADS)

    Das, D.; Chand, B. G.; Wu, J. S.; Lu, T.-H.; Sinha, C.

    2007-10-01

    Manganese(II)-naphthylazoimidazole complexes using N3- and NCS - as counter ions are characterized as Mn(β-NaiR) 2(X) 2(β-NaiEt = 1-alkyl-2-(naphthyl-β-azo)imidazole; X=N3-, NCS -). The ligands are unsymmetric N(imidazole), N(azo) chelating agents. The microanalytical, spectral (FT-IR, UV-vis), magnetic (bulk moment and EPR) and electrochemical data establish the structure and composition of the complexes. The single crystal X-ray diffraction studies of Mn(β-NaiEt) 2(N 3) 2 and Mn(β-NaiEt) 2(NCS) 2(β-NaiEt = 1-ethyl-2-(naphthyl-β-azo)imidazole) have confirmed the three dimensional structure of the complexes. Cyclic voltammetry exhibits high potential Mn(III)/Mn(II) couple along with azo reductions. The EPR spectra show usual pattern.

  11. High-density functionalization and cross-linking of DNA: "click" and "bis-click" cycloadditions performed on alkynylated oligonucleotides with fluorogenic anthracene azides.

    PubMed

    Pujari, Suresh S; Ingale, Sachin A; Seela, Frank

    2014-10-15

    High density functionalization of DNA with ethynyl and octadiynyl side chains followed by CuAAC "click labeling" with 9-azidomethylanthracene was performed. Alkynyl DNA was also cross-linked with fluorogenic 9,10-bis-azidomethylanthracene employing the "bis-click" reaction. By this means the fluorescence of the anthracene moiety was imparted to the virtually nonfluorescent DNA. Phosphoramidites of 8-aza-7-deaza-2'-deoxyadenosine with short and long linker arms in a steric nondemanding 7-position were utilized in solid phase oligodeoxynucleotide synthesis. High density alkynylated DNA-without anthracene residues-was found to be of comparable stability with both long and short linker arms. High density anthracene functionalized DNA became less stable with the short linker compared to that with the long linker connectivity. Interstrand cross-linked homodimers constructed from alkynylated oligonucleotides with fluorogenic 9,10-bis-azidomethylanthracene were hybridized with complementary strands to form double helices. They are more stable when the linker was located at a terminus than in a central position. Short linker anthracene adducts were destabilizing compared to long linker adducts. The fluorogenic anthracene residues not only have a significant effect on the duplex stability, but also impart fluorescence to the species. Fluorescence of cross-linked double helices with long linker connectivity was quenched when the cross-link was in a terminal position and was dequenched when the linker was connecting the two double helices at the center of the molecule. The fluorescence of the anthracene cross-linked double helices was strongly increased (dequenched) when the correct base pair was formed, while no change occurred upon mismatch formation.

  12. 40 CFR 721.715 - Trisubstituted anthracene.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Trisubstituted anthracene. 721.715... Substances § 721.715 Trisubstituted anthracene. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as trisubstituted anthracene (PMN P-91-689)...

  13. Effect of the addition of a nonaqueous polar solvent (glycerol) on enzymatic catalysis in reverse micelles. Hydrolysis of 2-naphthyl acetate by alpha-chymotrypsin.

    PubMed

    Falcone, R Darío; Biasutti, M Alicia; Correa, N Mariano; Silber, Juana J; Lissi, Eduardo; Abuin, Elsa

    2004-07-06

    The kinetics of hydrolysis of 2-naphthyl acetate (2-NA) catalyzed by alpha-chymotrypsin (alpha-CT), in reverse micellar solutions formed by glycerol (GY)-water (38% v/v) mixture/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/n-heptane has been determined by spectroscopic measurements. To compare the efficiency of this reaction with that observed in micelles with water in the core, as well as in the corresponding homogeneous media, the reaction was also studied in water/AOT/n-heptane reverse micellar solutions and in both homogeneous media (water and GY-water, 38% v/v mixture). In every media, alpha-CT was characterized by the absorption and emission spectra, the fluorescence lifetimes, and the fluorescence anisotropy of its tryptophan residues. The effect of AOT concentration on the kinetic parameters obtained in the micellar systems was determined, at a constant molar ratio of the inner polar solvent and surfactant. Moreover, the data obtained allowed the evaluation of the 2-NA partition constant between the organic and the micellar pseudophase. It is shown that the addition of GY to the micelle interior results in an increase in the catalytic properties of alpha-CT. The fluorescence anisotropy studies in the different media show that the addition of GY increases the viscosity as compared with the aqueous systems. It seems that the GY addition to the reverse micellar aggregates results in a decrease of the conformational mobility of alpha-CT, which leads to an increase of the enzyme stability and activity.

  14. Cationic reverse micelles create water with super hydrogen-bond-donor capacity for enzymatic catalysis: hydrolysis of 2-naphthyl acetate by alpha-chymotrypsin.

    PubMed

    Moyano, Fernando; Falcone, R Dario; Mejuto, J C; Silber, Juana J; Correa, N Mariano

    2010-08-02

    Reverse micelles (RMs) are very good nanoreactors because they can create a unique microenvironment for carrying out a variety of chemical and biochemical reactions. The aim of the present work is to determine the influence of different RM interfaces on the hydrolysis of 2-naphthyl acetate (2-NA) by alpha-chymotrypsin (alpha-CT). The reaction was studied in water/benzyl-n-hexadecyldimethylammonium chloride (BHDC)/benzene RMs and, its efficiency compared with that observed in pure water and in sodium 1,4-bis-2-ethylhexylsulfosuccinate (AOT) RMs. Thus, the hydrolysis rates of 2-NA catalyzed by alpha-CT were determined by spectroscopic measurements. In addition, the method used allows the joint evaluation of the substrate partition constant K(p) between the organic and the micellar pseudophase and the kinetic parameters: catalytic rate constant k(cat), and the Michaelis constant K(M) of the enzymatic reaction. The effect of the surfactant concentration on the kinetics parameters was determined at constant W(0)=[H(2)O]/[surfactant], and the variation of W(0) with surfactant constant concentration was investigated. The results show that the classical Michaelis-Menten mechanism is valid for alpha-CT in all of the RMs systems studied and that the reaction takes place at both RM interfaces. Moreover, the catalytic efficiency values k(cat)/K(M) obtained in the RMs systems are higher than that reported in water. Furthermore, there is a remarkable increase in alpha-CT efficiency in the cationic RMs in comparison with the anionic system, presumably due to the unique water properties found in these confined media. The results show that in cationic RMs the hydrogen-bond donor capacity of water is enhanced due to its interaction with the cationic interface. Hence, entrapped water can be converted into "super-water" for the enzymatic reaction studied in this work.

  15. Development and validation of a simple and sensitive HPLC-UV method for the determination of captopril in human plasma using a new derivatizing reagent 2-naphthyl propiolate.

    PubMed

    Rastkari, Noushin; Khoobi, Mehdi; Shafiee, Abbas; Khoshayand, Mohammad Reza; Ahmadkhaniha, Reza

    2013-08-01

    In this study, a simple, sensitive and reliable HPLC-UV method applying rapid sample preparation technique for the determination of captopril in human plasma was developed and validated. The method is based on pre-column derivatization of captopril and 2-propene-1-thiol (internal standard) with a new reagent 2-naphthyl propiolate. Sample clean-up, derivatization and extraction were carried out in two steps, totally less than 30min. The extracts were chromatographed on a C18 column (5μm, 150mm×4.6mmi.d.). The mobile phase consisted of methanol (75%, v/v) and phosphate buffer (25%, pH=8, 0.01M). UV detection was performed at 290nm. To obtain the best reaction yield, the factors that could influence the derivatization process, including the concentration of derivatization reagent, pH of sample solution and temperature were investigated in detail and optimized using Box-Behnken response surface methodology. Under optimized conditions the average extraction recovery of captopril and internal standard were >86%. The achieved lower limit of quantification (LLOQ) was 3ng/mL; the assay exhibited a linear dynamic range of 3-2000ng/mL with correlation coefficient (r(2)) of ≥0.99. The precision was satisfactory in the whole calibration range with RSD of 5.9-12.4% (accuracy: from 97.5% to 93.6%) and of 6.4-12.8% (accuracy: from 97.3% to 95.2%) for intra- and inter-assay, respectively. The method stability was confirmed in a series of experiments including: freeze-thaw, short- and long-term stability testing. Lastly, the developed method was successfully applied to the bioequivalence study of captopril administrated as a single oral dose (50mg) to 12 healthy male volunteers.

  16. Photoluminescence in anthracene and it's derivatives

    NASA Astrophysics Data System (ADS)

    Vyas, Arpita; Mirgane, Nitin A.; Moharil, S. V.; Muley, Aarti Iyer

    2016-05-01

    The anthracene and it's derivative 9-chloro acridine and Anthracene-9-ylmethylacetate have prepared in Poly vinyl alcohol(PVOH). Their photoluminescence properties have studied. The pure anthracene has an emission at 424 and 443nm. The intense peak is observed at 465nm and shoulder at 407nm. The derivatives of anthracene Anthracene-9-ylmethylacetate shows an emission around 440nm for the excitation at 393nm and 9-chloro acridine shows emission around 360nm for the excitation at 290nm. The major problem of this organic material is the stability. The composites prepared in the medium of PVOH are more stable.

  17. Dibenz[a,h]anthracene

    Integrated Risk Information System (IRIS)

    Dibenz [ a , h ] anthracene ; CASRN 53 - 70 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncar

  18. Excellent deep-blue emitting materials based on anthracene derivatives for non-doped organic light-emitting diodes

    NASA Astrophysics Data System (ADS)

    Wang, Zhiqiang; Liu, Wei; Xu, Chen; Ji, Baoming; Zheng, Caijun; Zhang, Xiaohong

    2016-08-01

    Two deep-blue emitting materials 2-tert-butyl-9,10-bis(3,5-diphenylphenyl)anthracene (An-1) and 2-tert-butyl-9,10-bis(3,5-diphenylbiphenyl-4‧-yl)anthracene (An-2) were successfully synthesized by the Pd-catalyzed Suzuki coupling reaction. Both of these compounds have high thermal stabilities and show strong deep-blue emission as solid-state film as well as in n-hexane solution. Two non-doped electroluminescent devices employing An-1 and An-2 as emitting layers were fabricated by vacuum vapor deposition. These devices exhibited highly efficient and stable deep-blue emission with high color purity. The CIE coordinate and maximum EQE of An-1 based device are 4.2% and (0.16, 0.06), respectively. Device based on An-2 achieved a maximum EQE of 4.0% and a CIE coordinate of (0.16, 0.10).

  19. Two BN isosteres of anthracene: synthesis and characterization.

    PubMed

    Ishibashi, Jacob S A; Marshall, Jonathan L; Mazière, Audrey; Lovinger, Gabriel J; Li, Bo; Zakharov, Lev N; Dargelos, Alain; Graciaa, Alain; Chrostowska, Anna; Liu, Shih-Yuan

    2014-10-29

    The synthesis of two parental BN anthracenes, 1 and 2, was developed, and their electronic structure and reactivity behavior were characterized in direct comparison with all-carbon anthracene. Gas-phase UV-photoelecton spectroscopy studies revealed the following HOMO energy trend: anthracene, -7.4 eV; BN anthracene 1, -7.7 eV; bis-BN anthracene 2, -8.0 eV. The λmax of the lower energy band in the UV-vis absorption spectrum is as follows: anthracene, 356 nm; BN anthracene 1, 359 nm; bis-BN anthracene 2, 357 nm. Thus, although the HOMO is stabilized with increasing BN incorporation, the HOMO-LUMO band gap remains unchanged across the anthracene series. The emission λmax values for the three investigated anthracene compounds are at 403 nm. The pKa values of the N-H proton for BN anthracene 1 and bis-BN anthracene 2 were determined to be approximately 26. BN anthracenes 1 and 2 do not undergo heat- or light-induced cycloaddition reactions or Friedel-Crafts acylations. Electrophilic bromination of BN anthracene 1 with Br2, however, occurs regioselectively at the 9-position. The reactivity behavior and regioselectivity of bromination of BN anthracenes are consistent with the electronic structure of these compounds; i.e., (1) the lower HOMO energy levels for BN anthracenes stabilize the molecules against cycloaddition and Friedel-Crafts reactions, and (2) the HOMO orbital coefficients are consistent with the observed bromination regioselectivity. Overall, this work demonstrates that BN/CC isosterism can be used as a molecular design strategy to stabilize the HOMO of acene-type structures while the optical band gap is maintained.

  20. Design and application of anthracene derivative with aggregation-induced emission charateristics for visualization and monitoring of erythropoietin unfolding.

    PubMed

    Sun, Binjie; Yang, Xiaojun; Ma, Lin; Niu, Caixia; Wang, Fangfang; Na, Na; Wen, Jiying; Ouyang, Jin

    2013-02-12

    Erythropoietin (EPO) is an attractive protein-unfolding/folding model because of its high degree of unfolding and folding reversibility and intermediate size. Due to its function for regulating red blood cell production by stimulating late erythroid precursor cells, EPO presents obvious values to biological research. A nonemissive anthracene derivative, that is 9,10-bis[4-(3-sulfonatopropoxyl)-styryl]anthracene sodium salt (BSPSA), with aggregation-induced emission (AIE) charateristics shows a novel phenomenon of AIE when EPO is added. The AIE biosensor for EPO shows the limit of detection is 1 × 10(-9) M. Utilizing the AIE feature of BSPSA, the unfolding process of EPO using guanidine hydrochloride is monitored, which indicates three steps for the folding structures of EPO to transform to random coil. Computational modeling suggests that the BSPSA luminogens prefer docking in the hydrophobic cavity in the EPO folding structures, and the assembly of BSPSA in this cavity makes the AIE available, making the monitoring of unfolding of EPO possible.

  1. Photocycloaddition of anthracene to excited C-60

    SciTech Connect

    Gol`dshleger, N.F.; Denisov, N.N.; Lobach, A.S.

    1995-02-01

    The ability to participate in photochemical cycloaddition reactions is characteristic feature of chromophores with a carbon double bond. In this work, the authors demonstrate the formation of an adduct by cycloaddition of anthracene to the triplet-excited C-60 fullerene under anaerobic conditions, which provides a straight forward way to synthesize new derivatives of C-60 fullerenes. Reaction methods, conditions, and mechanisms are included along with the characterization of the fullerene derivative with IR, MS, and NMR methods.

  2. Microbial transformation and sorption of anthracene in liquid culture.

    PubMed

    Hadibarata, Tony; Zubir, Meor Mohd Fikri Ahmad; Rubiyatno; Chuang, Teh Zee

    2013-09-01

    Armillaria sp. F022, a white-rot fungus isolated from decayed wood in tropical rain forest was used to biodegrade anthracene in cultured medium. The percentage of anthracene removal by Armillaria sp. F022 reached 13 % after 7 days and at the end of the experiment, anthracene removal level was at 87 %. The anthracene removal through sorption and transformation was investigated. 69 % of eliminated anthracene was transformed by Armillaria sp. F022 to form other organic structure, while only 18 % was absorbed in the mycelia. In the kinetic experiment, anthracene dissipation will not stop even though the biomass had stopped growing. Anthracene removal by Armillaria sp. F022 was correlated with protein concentration (whole biomass) in the culture. The production of enzyme was affected by biomass production. Anthracene was transformed to two stable metabolic products. The metabolites were extracted in ethyl-acetate, isolated by column chromatography, and then identified using gas chromatography-mass spectrometry (GC-MS).

  3. An Unprecedented Photochemical Reaction for Anthracene-Containing Derivatives.

    PubMed

    Zhao, Jiang-Lin; Jiang, Xue-Kai; Wu, Chong; Wang, Chuan-Zeng; Zeng, Xi; Redshaw, Carl; Yamato, Takehiko

    2016-10-18

    A series of anthracene-containing derivatives have been synthesised and characterised. The photochemical behaviour of these derivatives have been investigated by (1) H NMR spectroscopy. An unprecedented photolysis reaction for anthracene-containing derivatives was observed in the case of anthracenes directly armed with a -CH2 O-R group upon UV irradiation. The photolysis reaction process has been demonstrated to occur in three steps. Firstly, the anthracene-containing derivatives are converted into the corresponding endoperoxide intermediate upon UV irradiation in the presence of air; then, the endoperoxide intermediate is decomposed to the corresponding starting compound and 9-anthraldehyde; finally, 9-anthraldehyde is further oxidised to anthraquinone. Additionally, the photolysis reaction of anthracene-containing derivatives is significantly promoted in the presence of a thiacalix[4]arene platform.

  4. Mesophase from anthracene oil-based pitches

    SciTech Connect

    P. Alvarez; J. Sutil; R. Santamaria; C. Blanco; R. Menendez; M. Granda

    2008-11-15

    This work deals with the preparation of the mesophase from two pitch-like materials obtained from anthracene oil by oxidative thermal condensation (AOP-1) and the subsequent thermal treatment and distillation of AOP-1 (AOP-2). The mesophase was obtained by the controlled pyrolysis (440-470{degree}C and different periods of residence times) and subsequent sedimentation of the samples. In the case of the pitch prepared by oxidative thermal condensation, a dynamic pressure of 5 bar was applied during the pyrolysis. The pressure was a critical parameter, and its influence was also investigated. The results show that AOP-1 requires higher temperatures and/or residence times to develop mesophase than AOP-2. After sedimentation, a sample consisting of mainly mesophase was produced in all of the cases. The characterization of the mesophases by means of techniques, such as elemental and thermogravimetric analysis and optical microscopy, showed that anthracene oil-based derivatives are appropriate precursors for producing QI-free mesophase with suitable properties for the fabrication of a wide range of carbon materials. 26 refs., 5 figs., 3 tabs.

  5. Homogeneous and heterogeneous reactions of anthracene with selected atmospheric oxidants.

    PubMed

    Zhang, Yang; Shu, Jinian; Zhang, Yuanxun; Yang, Bo

    2013-09-01

    The reactions of gas-phase anthracene and suspended anthracene particles with O3 and O3-NO were conducted in a 200-L reaction chamber, respectively. The secondary organic aerosol (SOA) formations from gas-phase reactions of anthracene with O3 and O3-NO were observed. Meanwhile, the size distributions and mass concentrations of SOA were monitored with a scanning mobility particle sizer (SMPS) during the formation processes. The rapid exponential growths of SOA reveal that the atmospheric lifetimes of gas-phase anthracene towards O3 and O3-NO are less than 20.5 and 4.34 hr, respectively. The particulate oxidation products from homogeneous and heterogeneous reactions were analyzed with a vacuum ultraviolet photoionization aerosol time-of-flight mass spectrometer (VUV-ATOFMS). Gas chromatograph/mass spectrometer (GC/MS) analyses of oxidation products of anthracene were carried out for assigning the time-of-flight (TOF) mass spectra of products from homogeneous and heterogeneous reactions. Anthrone, anthraquinone, 9,10-dihydroxyanthracene, and 1,9,10-trihydroxyanthracene were the ozonation products of anthracene, while anthrone, anthraquinone, 9-nitroanthracene, and 1,8-dihydroxyanthraquinone were the main products of anthracene with O3-NO.

  6. Identification of toxic products of anthracene photomodification in simulated sunlight.

    PubMed

    Brack, Werner; Altenburger, Rolf; Küster, Eberhard; Meissner, Bettina; Wenzel, Klaus-Dieter; Schüürmann, Gerrit

    2003-10-01

    Currently, the evidence of a rapid photomodification of anthracene under sunlight resulting in enhanced toxicity exists; however, the chemical causes of toxicity are still unknown. The present study aimed at filling this gap by irradiation of an anthracene suspension with simulated sunlight and subsequent effect-directed fractionation and analysis of toxic products with respect to the inhibition of bacterial energy metabolism of Vibrio fischeri, reproduction of the green algae Scenedesmus vacuolatus, and genotoxicity in the umuC test. Algal toxicity of anthracene was hardly modified by irradiation prior to testing and distributed over all fractions with emphasis on the fractions containing anthracene-9,10-dione and a photometabolite suggested to be 10-hydroxyanthrone. Bacterial toxicity and genotoxicity in contrast emerged only when anthracene was irradiated. Anthracene-1,4-dione, a so-far-unknown trace photometabolite, was identified as a very potent toxicant dominating the toxicity of photomodified anthracene to V. fischeri. In genotoxic fractions, 1-hydroxyanthracene-9,10-dione and 1,4-dihydroxyanthracene-9,10-dione were identified and confirmed as genotoxicants. The results stress the potential of effect-directed analysis approaches in contrast to mere chemical analysis in studies aiming at toxicologically relevant photomodified substances.

  7. Thermochemical and Vapor Pressure Behavior of Anthracene and Brominated Anthracene Mixtures.

    PubMed

    Fu, Jinxia; Suuberg, Eric M

    2013-03-25

    The present work concerns the thermochemical and vapor pressure behavior of the anthracene (1) + 2-bromoanthracene (2) and anthracene (1) + 9-bromoanthracene (3) systems. Solid-liquid equilibrium temperature and differential scanning calorimetry studies indicate the existence of a minimum melting solid state near an equilibrium temperature of 477.65 K at x1 = 0.74 for the (1) + (2) system. Additionally, solid-vapor equilibrium studies for the (1) + (2) system show that the vapor pressure of the mixtures depends on composition, but does not follow ideal Raoult's law behaviour. The (1) + (3) system behaves differently from the (1) + (2) system. The (1) + (3) system has a solid solution like phase diagram. The system consists of two phases, an anthracene like phase and a 9-bromoanthracene like phase, while (1) + (2) mixtures only form a single phase. Moreover, experimental studies of the two systems suggest that the (1) + (2) system is in a thermodynamically lower energy state than the (1) + (3) system.

  8. Thermochemical and Vapor Pressure Behavior of Anthracene and Brominated Anthracene Mixtures

    PubMed Central

    Suuberg, Eric M.

    2013-01-01

    The present work concerns the thermochemical and vapor pressure behavior of the anthracene (1) + 2-bromoanthracene (2) and anthracene (1) + 9-bromoanthracene (3) systems. Solid-liquid equilibrium temperature and differential scanning calorimetry studies indicate the existence of a minimum melting solid state near an equilibrium temperature of 477.65 K at x1 = 0.74 for the (1) + (2) system. Additionally, solid-vapor equilibrium studies for the (1) + (2) system show that the vapor pressure of the mixtures depends on composition, but does not follow ideal Raoult’s law behaviour. The (1) + (3) system behaves differently from the (1) + (2) system. The (1) + (3) system has a solid solution like phase diagram. The system consists of two phases, an anthracene like phase and a 9-bromoanthracene like phase, while (1) + (2) mixtures only form a single phase. Moreover, experimental studies of the two systems suggest that the (1) + (2) system is in a thermodynamically lower energy state than the (1) + (3) system. PMID:24319314

  9. Transformation of anthracene on various cation-modified clay minerals.

    PubMed

    Li, Li; Jia, Hanzhong; Li, Xiyou; Wang, Chuanyi

    2015-01-01

    In this study, anthracene was employed as a probe to explore the potential catalytic effect of clay minerals in soil environment. Clay minerals saturated with various exchangeable cations were tested. The rate of anthracene transformation follows the order: Fe-smectite > Cu-smectite > Al-smectite ≈ Ca-smectite ≈ Mg-smectite ≈ Na-smectite. This suggests that transition-metal ions such as Fe(III) play an important role in anthracene transformation. Among Fe(III)-saturated clays, Fe(III)-smectite exhibits the highest catalytic activity followed by Fe(III)-illite, Fe(III)-pyrophyllite, and Fe(III)-kaolinite, which is in agreement with the interlayer Fe(III) content. Moreover, effects by two common environmental factors, pH and relative humidity (RH), were evaluated. With an increase in pH or RH, the rate of anthracene transformation decreases rapidly at first and then is leveled off. GC-MS analysis identifies that the final product of anthracene transformation is 9,10-anthraquinone, a more bioavailable molecule compared to anthracene. The transformation process mainly involves cation-π bonding, electron transfer leading to cation radical, and further oxidation by chemisorbed O2. The present work provides valuable insights into the abiotic transformation and the fate of PAHs in the soil environment and the development of contaminated land remediation technologies.

  10. Fungal biodegradation of anthracene-polluted cork: A comparative study.

    PubMed

    Jové, Patrícia; Olivella, Maria À; Camarero, Susana; Caixach, Josep; Planas, Carles; Cano, Laura; De Las Heras, Francesc X

    2016-01-01

    The efficiency of cork waste in adsorbing aqueous polycyclic aromatic hydrocarbons (PAHs) has been previously reported. Biodegradation of contaminated cork using filamentous fungi could be a good alternative for detoxifying cork to facilitate its final processing. For this purpose, the degradation efficiency of anthracene by three ligninolytic white-rot fungi (Phanerochaete chrysosporium, Irpex lacteus and Pleurotus ostreatus) and three non-ligninolytic fungi which are found in the cork itself (Aspergillus niger, Penicillium simplicissimum and Mucor racemosus) are compared. Anthracene degradation by all fungi was examined in solid-phase cultures after 0, 16, 30 and 61 days. The degradation products of anthracene by P. simplicissimum and I. lacteus were also identified by GC-MS and a metabolic pathway was proposed for P. simplicissimum. Results show that all the fungi tested degraded anthracene. After 61 days of incubation, approximately 86%, 40%, and 38% of the initial concentration of anthracene (i.e., 100 µM) was degraded by P. simplicissimum, P. chrysosporium and I. lacteus, respectively. The rest of the fungi degraded anthracene to a lesser extent (<30%). As a final remark, the results obtained in this study indicate that P. simplicissimum, a non-ligninolytic fungi characteristic of cork itself, could be used as an efficient degrader of PAH-contaminated cork.

  11. Excited singlet states of covalently bound, cofacial dimers and trimers of perylene-3,4:9,10-bis(dicarboximide)s.

    PubMed

    Giaimo, Jovan M; Lockard, Jenny V; Sinks, Louise E; Scott, Amy M; Wilson, Thea M; Wasielewski, Michael R

    2008-03-20

    Perylene-3,4:9,10-bis(dicarboximide) (PDI) and its derivatives are robust organic dyes that strongly absorb visible light and display a strong tendency to self-assemble into ordered aggregates, having significant interest as photoactive materials in a wide variety of organic electronics. To better understand the nature of the electronics states produced by photoexcitation of such aggregates, the photophysics of a series of covalent, cofacially oriented, pi-stacked dimers and trimers of PDI and 1,7-bis(3',5'-di-t-butylphenoxy)perylene-3,4:9,10-bis(dicarboximide) (PPDI) were characterized using both time-resolved absorption and fluorescence spectroscopy. The covalent linkage between the chromophores was accomplished using 9,9-dimethylxanthene spacers. Placing n-octyl groups on the imide nitrogen atoms at the end of the PDI chromophores not attached to the xanthene spacer results in PDI dimers having near optimal pi-stacking, leading to formation of a low-energy excimer-like state, while substituting the more sterically demanding 12-tricosanyl group on the imides causes deviations from the optimum that result in slower formation of an excimer-like excited state having somewhat higher energy. By comparison, PPDI dimers having terminal n-octyl imide groups have two isomers, whose photophysical properties depend on the ability of the phenoxy groups at the 1,7-positions to modify the pi stacking of the PPDI molecules. In general, disruption of optimal pi-stacking by steric interactions of the phenoxy side groups results in excimer-like states that are higher in energy. The corresponding lowest excited singlet states of the PDI and PPDI trimers are dimer-like in nature and suggest that structural distortions that accompany formation of the trimers are sufficient to confine the electronic interaction on two chromophores within these systems. This further suggests that it may be useful to build into oligomeric PDI and PPDI systems some degree of flexibility that allows the

  12. Characterization and pyrolysis behavior of novel anthracene oil derivatives

    SciTech Connect

    P. Alvarez; M. Granda; J. Sutil; R. Menendez; J.J. Fernandez; J.A. Vina; T.J. Morgan; M. Millan; A.A. Herod; R. Kandiyoti

    2008-11-15

    The characterization and pyrolysis behavior of a set of pitches prepared from anthracene oil have been described. The pitches were obtained from four successive cycles of a sequential process that begins with blowing air through the heated anthracene oil, to bring about recombination reactions. Reaction products are distilled to give a pitch residue and a lighter fraction. Thermal treatment/distillation cycles of this reaction product yield a pitch and a distillate fraction (unreacted anthracene oil) during each subsequent stage. Products obtained during the process have been characterized by elemental analysis, Fourier transform infrared (FTIR) and ultraviolet (UV)-fluorescence spectroscopy, and size-exclusion chromatography (SEC). The pyrolytic behavior of the anthracene oil derivatives was examined using a thermogravimetric balance. Thermal treatment of the anthracene oil and its (distilled) reaction products at 440-460{degree}C under 5 bar pressure leads to a partially anisotropic pitch with the formation of a liquid crystal phase (mesophase). The formation and evolution of these mesophases were analyzed by optical microscopy. 25 refs., 9 figs., 3 tabs.

  13. Thermodynamic study of (anthracene + phenanthrene) solid state mixtures.

    PubMed

    Rice, James W; Fu, Jinxia; Sandström, Emma; Ditto, Jenna C; Suuberg, Eric M

    2015-11-01

    Polycyclic aromatic hydrocarbons (PAH) are common components of many materials, such as petroleum and various types of tars. They are generally present in mixtures, occurring both naturally and as byproducts of fuel processing operations. It is important to understand the thermodynamic properties of such mixtures in order to understand better and predict their behavior (i.e., fate and transport) in the environment and in industrial operations. To characterize better the thermodynamic behavior of PAH mixtures, the phase behavior of a binary (anthracene + phenanthrene) system was studied by differential scanning calorimetry, X-ray diffraction, and the Knudsen effusion technique. Mixtures of (anthracene + phenanthrene) exhibit non-ideal mixture behavior. They form a lower-melting, phenanthrene-rich phase with an initial melting temperature of 372 K (identical to the melting temperature of pure phenanthrene) and a vapor pressure of roughly lnP/Pa = -2.38. The phenanthrene-rich phase coexists with an anthracene-rich phase when the mole fraction of phenanthrene (xP) in the mixture is less than or equal to 0.80. Mixtures initially at xP = 0.90 consist entirely of the phenanthrene-rich phase and sublime at nearly constant vapor pressure and composition, consistent with azeotrope-like behavior. Quasi-azeotropy was also observed for very high-content anthracene mixtures (2.5 < xP < 5) indicating that anthracene may accommodate very low levels of phenanthrene in its crystal structure.

  14. Thermodynamic study of (anthracene + phenanthrene) solid state mixtures

    PubMed Central

    Rice, James W.; Fu, Jinxia; Sandström, Emma; Ditto, Jenna C.; Suuberg, Eric M.

    2015-01-01

    Polycyclic aromatic hydrocarbons (PAH) are common components of many materials, such as petroleum and various types of tars. They are generally present in mixtures, occurring both naturally and as byproducts of fuel processing operations. It is important to understand the thermodynamic properties of such mixtures in order to understand better and predict their behavior (i.e., fate and transport) in the environment and in industrial operations. To characterize better the thermodynamic behavior of PAH mixtures, the phase behavior of a binary (anthracene + phenanthrene) system was studied by differential scanning calorimetry, X-ray diffraction, and the Knudsen effusion technique. Mixtures of (anthracene + phenanthrene) exhibit non-ideal mixture behavior. They form a lower-melting, phenanthrene-rich phase with an initial melting temperature of 372 K (identical to the melting temperature of pure phenanthrene) and a vapor pressure of roughly lnP/Pa = −2.38. The phenanthrene-rich phase coexists with an anthracene-rich phase when the mole fraction of phenanthrene (xP) in the mixture is less than or equal to 0.80. Mixtures initially at xP = 0.90 consist entirely of the phenanthrene-rich phase and sublime at nearly constant vapor pressure and composition, consistent with azeotrope-like behavior. Quasi-azeotropy was also observed for very high-content anthracene mixtures (2.5 < xP < 5) indicating that anthracene may accommodate very low levels of phenanthrene in its crystal structure. PMID:26973354

  15. Plasmid-mediated mineralization of naphthalene, phenanthrene, and anthracene

    SciTech Connect

    Sanseverino, J. IT Corp., Knoxville, TN ); Applegate, B.M.; King, J.M.H.; Sayler, G.S. )

    1993-06-01

    The biochemistry and genetics of the naphthalene degradation pathway contained on plasmid NAH7 have been well characterized. However, not much is known about the substrate specificity of the enzymes of nah operons and whether the nah-encoded enzymes are capable of metabolizing higher polyaromatic hydrocarbons. This paper shows that NAH7 and NAH7-like plasmids can mediate metabolism of phenanthrene and anthracene as well as naphthalene. In addition, a mutant blocked in the nahG (salicylate hydroxylase) gene produced unidentified metabolites when it is grown in the presence of phenanthrene and anthracene. This implies that phenanthrene and anthracene are degraded through the nah plasmid-encoded system. 29 refs., 3 figs., 2 tabs.

  16. Enhanced biodegradation of anthracene in acidic soil by inoculated Burkholderia sp. VUN10013.

    PubMed

    Somtrakoon, Khanitta; Suanjit, Sudarat; Pokethitiyook, Prayad; Kruatrachue, Maleeya; Lee, Hung; Upatham, Suchart

    2008-08-01

    The ability of Burkholderia sp. VUN10013 to degrade anthracene in microcosms of two acidic Thai soils was studied. The addition of Burkholderia sp. VUN10013 (initial concentration of 10(5) cells g(-1) dry soil) to autoclaved soil collected from the Plew District, Chanthaburi Province, Thailand, supplemented with anthracene (50 mg kg(-1) dry soil) resulted in complete degradation of the added anthracene within 20 days. In contrast, under the same test conditions but using autoclaved soil collected from the Kitchagude District, Chanthaburi Province, Thailand, only approximately 46.3% of the added anthracene was degraded after 60 days of incubation. In nonautoclaved soils, without adding the VUN10013 inocula, 22.8 and 19.1% of the anthracene in Plew and Kitchagude soils, respectively, were degraded by indigenous bacteria after 60 days. In nonautoclaved soil inoculated with Burkholderia sp. VUN10013, the rate and extent of anthracene degradation were considerably better than those seen in autoclaved soils or in uninoculated nonautoclaved soils in that only 8.2 and 9.1% of anthracene remained in nonautoclaved Plew and Kitchagude soils, respectively, after 10 days of incubation. The results showed that the indigenous microorganisms in the pristine acidic soils have limited ability to degrade anthracene. Inoculation with the anthracene-degrading Burkholderia sp. VUN10013 significantly enhanced anthracene degradation in such acidic soils. The indigenous microorganisms greatly assisted the VUN10013 inoculum in anthracene degradation, especially in the more acidic Kitchagude soil.

  17. Anthracene Clusters and the Interstellar Infrared Emission Features

    NASA Astrophysics Data System (ADS)

    Roser, J. E.; Ricca, A.; Allamandola, L. J.

    2014-03-01

    The unidentified infrared bands are ubiquitous in the interstellar medium and typically attributed to emission from neutral and ionized polycyclic aromatic hydrocarbons (or PAHs). The contribution of neutral PAH clusters to these bands has been impossible to determine due to a paucity of infrared spectral data. Here we investigated neutral clusters of the three-ring PAH anthracene using FTIR absorption spectroscopy of anthracene matrix-isolated at varying concentrations in solid argon. In order to determine likely cluster structures of the embedded molecules, we also calculated theoretical absorption spectra for the anthracene monomer through hexamer using density functional theory with a dispersion correction (DFT-D). The DFT-D calculations have been calibrated for the anthracene dimer using the second-order Møller-Plesset approach. Because there is some support for the hypothesis that three or four-ring PAHs are present in the Red Rectangle nebula, we discuss the application of our results to this nebula in particular as well as to the interstellar infrared emission in general.

  18. Anthracene clusters and the interstellar infrared emission features

    SciTech Connect

    Roser, J. E.; Ricca, A.; Allamandola, L. J.

    2014-03-10

    The unidentified infrared bands are ubiquitous in the interstellar medium and typically attributed to emission from neutral and ionized polycyclic aromatic hydrocarbons (or PAHs). The contribution of neutral PAH clusters to these bands has been impossible to determine due to a paucity of infrared spectral data. Here we investigated neutral clusters of the three-ring PAH anthracene using FTIR absorption spectroscopy of anthracene matrix-isolated at varying concentrations in solid argon. In order to determine likely cluster structures of the embedded molecules, we also calculated theoretical absorption spectra for the anthracene monomer through hexamer using density functional theory with a dispersion correction (DFT-D). The DFT-D calculations have been calibrated for the anthracene dimer using the second-order Møller-Plesset approach. Because there is some support for the hypothesis that three or four-ring PAHs are present in the Red Rectangle nebula, we discuss the application of our results to this nebula in particular as well as to the interstellar infrared emission in general.

  19. Toxic photoproducts of phenanthrene and anthracene in sunlight

    SciTech Connect

    Duxbury, C.L.; McConkey, B.J.; Mallakin, A.; Dixon, D.G.; Greenberg, B.M.

    1995-12-31

    Phenanthrene and anthracene, two of the most prevalent PAHs, undergo significant increases in toxicity on exposure to sunlight. Over a period of several days exposure to light, the toxicity of an aqueous solution of phenanthrene or anthracene increased dramatically. This increase in toxicity is largely due to the primary products formed by these two PAHs due to light exposure. These compounds are more toxic than the parent compounds at equimolar concentrations. Although anthracene is a potent photosensitizer, phenanthrene did not exhibit a significant increase in toxicity due to photosensitization. Photo-oxidation was the principal cause of photoinduced toxicity, with 9,10-phenanthrenequinone being the primary product. This compound is more water soluble than phenanthrene increasing its bioavailability. In addition, mixtures of phenanthrene and 9,10-phenanthrenequinone exhibited toxicity similar to the quinone added alone. This was shown by joint toxicity testing using Lemna gibba and Daphnia magna. These two organisms are currently being used in the lab to further test individual oxidized products of anthracene and phenanthrene that occur as a result of exposure to sunlight.

  20. Carcinogenic Activity of Some Benz(a)Anthracene Derivatives in Newborn Mice

    PubMed Central

    Roe, F. J. C.; Dipple, A.; Mitchley, B. C. V.

    1972-01-01

    Equimolar doses of 7-methylbenz(a)anthracene and 3 of its derivatives were given to newborn male and female Swiss mice. All 4 substances tested increased the risk of tumour development compared with that seen in control mice given the vehicle, arachis oil, only. 7-Methylbenz(a)anthracene itself was the most actively tumorigenic of the compounds studied, giving rise to subcutaneous sarcomata at the site of injection, and multiple lung tumours and liver tumours. 7-Bromomethyl-12-methylbenz(a)-anthracene was similarly active in the lung and liver but evoked fewer subcutaneous sarcomata. 7-Bromomethylbenz(a)anthracene was seemingly slightly less active than either 7-methylbenz(a)anthracene or 7-bromomethyl-12-methylbenz(a)anthracene. 4-Chloro-7-bromomethylbenz(a)anthracene exhibited only marginal activity in that it slightly increased the risk of liver tumour development in male mice. PMID:4647396

  1. Substituent Effects on the Absorption and Fluorescence Properties of Anthracene.

    PubMed

    Abou-Hatab, Salsabil; Spata, Vincent A; Matsika, Spiridoula

    2017-02-16

    Substitution can be used to efficiently tune the photophysical properties of chromophores. In this study, we examine the effect of substituents on the absorption and fluorescence properties of anthracene. The effects of mono-, di-, and tetrasubstitution of electron-donating and -withdrawing functional groups were explored. In addition, the influence of a donor-acceptor substituent pair and the position of substitution were investigated. Eleven functional groups were varied on positions 1, 2, and 9 of anthracene, and on position 6 of 2-methoxyanthracene and 2-carboxyanthracene. Moreover, the donor-acceptor pair NH2/CO2H was added on different positions of anthracene for additional studies of doubly substituted anthracenes. Finally, we looked into quadruple substitutions on positions 1,4,5,8 and 2,3,6,7. Vertical excitation energies and oscillator strengths were computed using density functional theory with the hybrid CAM-B3LYP functional and 6-311G(d) basis set. Correlations between the excitation energies or oscillator strengths of the low-lying bright La state and the Hammett sigma parameter, σp(+), of the substituents were examined. The energy is red-shifted for all cases of substitution. Oscillator strengths increase when substituents are placed along the direction of the transition dipole moment of the bright La excited state. Substitution of long chain conjugated groups significantly increases the oscillator strength in comparison to the cases for other substituents. In addition, the results of quadruply substituted geometries reveal symmetric substitution at the 1,4,5,8 positions significantly increases the oscillator strength and can lower the band gap compared to that of the unsubstituted anthracene molecule by up to 0.5 eV.

  2. Comparing anthracene and fluorene degradation in anthracene and fluorene-contaminated soil by single and mixed plant cultivation.

    PubMed

    Somtrakoon, Khanitta; Chouychai, Waraporn; Lee, Hung

    2014-01-01

    The ability of three plant species (sweet corn, cucumber, and winged bean) to remediate soil spiked with 138.9 and 95.9 mg of anthracene and fluorene per kg of dry soil, respectively, by single and double plant co-cultivation was investigated. After 15 and 30 days of transplantation, plant elongation, plant weight, chlorophyll content, and the content of each PAH in soil and plant tissues were determined. Based on PAH removal and plant health, winged bean was the most effective plant for phytoremediation when grown alone; percentage of fluorene and anthracene remaining in the rhizospheric soil after 30 days were 7.8% and 24.2%, respectively. The most effective combination of plants for phytoremediation was corn and winged bean; on day 30, amounts of fluorene and anthracene remaining in the winged bean rhizospheric soil were 3.4% and 14.3%, respectively; amounts of fluorene and anthracene remaining in the sweet corn rhizospheric soil were 4.1% and 8.8%, respectively. Co-cultivation of sweet corn and cucumber could remove fluorene to a higher extent than anthracene from soil within 15 days, but these plants did not survive and died before day 30. The amounts of fluorene remaining in the rhizospheric soil of corn and cucumber were only 14% and 17.3%, respectively, on day 15. No PAHs were detected in plant tissues. This suggests that phytostimulation of microbial degradation in the rhizosphere was most likely the mechanism by which the PAHs were removed from the spiked soil. The results show that co-cultivation of plants has merit in the phytoremediation of PAH-spiked soil.

  3. Aggregation-controlled excimer emission from anthracene-containing polyamidoamine dendrimers.

    PubMed

    Lekha, P K; Prasad, Edamana

    2010-03-22

    Lower generations of polyamidoamine (PAMAM) dendrimers were peripherally modified with anthracene moieties, and excimer emission from anthracene chromophores was investigated in an acetonitrile-water mixture at acidic and basic pH values. Results from fluorescence spectroscopic experiments suggest that 1) the propensity of anthracene-modified PAMAM dendrimers to aggregate in acetonitrile is substantial in the presence of 15-20 vol % of water, and 2) aggregate formation in anthracene-modified PAMAM dendrimers leads to unique morphologies in the ground state, where the anthracene units are pre-arranged to form stable excimers upon photoexcitation. Three types of anthracene excimers are generated in the system, with face-to-face, angular, and T-shaped geometry. The formation of different types of anthracene excimers was confirmed by steady-state and time-resolved fluorescence spectroscopic experiments. Experimental results further suggest that it is feasible to alter the type of excimer formed by anthracene units attached to the PAMAM dendrimers through altering the propensity for ground-state aggregation. Most excitingly, increased pi conjugation in the molecular framework of anthracene-substituted PAMAM dendrimers leads to intense and exclusive excimer emission from anthracene at room temperature.

  4. Plasmid-mediated mineralization of naphthalene, phenanthrene, and anthracene.

    PubMed Central

    Sanseverino, J; Applegate, B M; King, J M; Sayler, G S

    1993-01-01

    The well-characterized plasmid-encoded naphthalene degradation pathway in Pseudomonas putida PpG7(NAH7) was used to investigate the role of the NAH plasmid-encoded pathway in mineralizing phenanthrene and anthracene. Three Pseudomonas strains, designated 5R, DFC49, and DFC50, were recovered from a polynuclear aromatic hydrocarbon-degrading inoculum developed from a manufactured gas plant soil slurry reactor. Plasmids pKA1, pKA2, and pKA3, approximately 100 kb in size, were isolated from these strains and characterized. These plasmids have homologous regions of upper and lower NAH7 plasmid catabolic genes. By conjugation experiments, these plasmids, including NAH7, have been shown to encode the genotype for mineralization of [9-14C]phenanthrene and [U-14C]anthracene, as well as [1-14C]naphthalene. One strain, Pseudomonas fluorescens 5RL, which has the complete lower pathway inactivated by transposon insertion in nahG, accumulated a metabolite from phenanthrene and anthracene degradation. This is the first direct evidence to indicate that the NAH plasmid-encoded catabolic genes are involved in degradation of polynuclear aromatic hydrocarbons other than naphthalene. Images PMID:8328809

  5. On the nature of the low lying singlet states of anthracene

    NASA Astrophysics Data System (ADS)

    Bree, A.; Leyderman, A.; Taliani, C.

    1986-03-01

    An analysis of the two-photon fluorescence excitation spectrum (TPES) of anthracene-h 10 and anthracene-d 10 in mixed crystal in the spectral range of 26000-31000 cm -1 at 4.2 K is presented. The two photon forbidden pure electronic origin of anthracene is particularly intense in fluorene mixed crystals because of the perturbation of the host matrix. In addition, a number of b lu vibrations give rise to a vibronic coupling with a second excited electronic state of total symmetry A g at about 29400 cm -1. The nature of this second excited state is discussed.

  6. Peculiarities of metabolism of anthracene and pyrene by laccase-producing fungus Pycnoporus sanguineus H1.

    PubMed

    Li, Xuanzhen; Wang, Yan; Wu, Shijin; Qiu, Lequan; Gu, Li; Li, Jingjing; Zhang, Bao; Zhong, Weihong

    2014-01-01

    The metabolic peculiarities of anthracene and pyrene by Pycnoporus sanguineus H1 were investigated. The fungus H1 could grow on potato dextrose agar plates with anthracene and anthraquinone as carbon sources. In liquid medium, the strain degraded 8.5% of anthracene as the sole carbon source, with no ligninolytic enzymes detected, indicating that intracellular catabolic enzymes might be responsible for the initial oxidation of anthracene. When bran was added to the medium, the degradation rate of anthracene and pyrene increased to 71.3% and 30.2%, respectively, and the laccase activities increased to a maximal value of 501.2 and 587.6 U/L, respectively. By gas chromatography-mass spectrometry analysis, anthraquinone was detected as the unique intermediate product of anthracene oxidation, with a yield molar ratio of 0.3. In vitro experiments showed that the extracellular culture fluid containing laccase transformed anthracene to anthraquinone with a yield molar ratio of 1.0, which was less than that of the in vivo experiment, indicating that anthraquinone could be further metabolized by the strain. Pyrene could not be oxidized by culture fluid. These results showed that both extracellular laccase and intracellular catabolic enzymes might play an important role in the initial oxidation of anthracene, whereas pyrene could be only oxidized by intracellular catabolic enzymes through cometabolism.

  7. Oxidation of anthracene using waste Mn oxide minerals: the importance of wetting and drying sequences.

    PubMed

    Clarke, Catherine; Tourney, Janette; Johnson, Karen

    2012-02-29

    PAHs are a common problem in contaminated urban soils due to their recalcitrance. This study presents results on the oxidation of anthracene on synthetic and natural Mn oxide surfaces. Evaporation of anthracene spiked Mn oxide slurries in air results in the oxidation of 30% of the anthracene to anthraquinone. Control minerals, quartz and calcite, also oxidised a small but significant proportion of the anthracene (4.5% and 14% conversion, respectively) when spiked mineral slurries were evaporated in air. However, only Mn oxide minerals showed significant anthracene oxidation (5-10%) when evaporation took place in the absence of oxygen (N2 atmosphere). In the fully hydrated systems where no drying took place, natural Mn oxides showed an increase in anthracene oxidation with decreasing pH, with a conversion of 75% anthracene at pH 4. These results show both acidification and drying favor the oxidation of anthracene on Mn oxide mineral surfaces. It has also been demonstrated that non-redox active mineral surfaces, such as calcite, may play a role in contaminant breakdown during wetting and drying sequences. Given that climate changes suggest that wetting and drying sequences are likely to become more significant these results have important implications for contaminated land remediation technologies.

  8. Interaction of higher plant (jute), electrofused bacteria and mycorrhiza on anthracene biodegradation.

    PubMed

    Cheung, K C; Zhang, J Y; Deng, H H; Ou, Y K; Leung, H M; Wu, S C; Wong, M H

    2008-05-01

    The interaction of bacteria, mycorrhiza and jute (Corchotus capsulari, a higher plant) to reduce anthracene in different concentrations of spiked soils was investigated. Dominant indigenous bacterium (Pseudomonas sp.) isolated in the rhizosphere of jute was electrofused with anthracene degraders (Sphingomonas paucimobilis and Pseudomonas aeruginosa) which were able to produce different types of biosurfactants. The highest population (56 x 10(5)CFU/g) was found in the planted soil with the inoculation of mixtures of electrofused anthracene degraders after 7 days. The growth of anthracene degraders in the spiked soil was improved by gene transfer from indigenous bacteria. After 35 days, enhanced anthracene removals were observed in inoculated soils planted with jute (65.5-75.2%) compared with unplanted soil without inoculation (12.5%). The interaction of jute and electrofused S. paucimobilis enabled the greatest reduction of soil anthracene with or without the addition of P. aeruginosa. Mycorrhizal colonization was not significantly inhibited by anthracene in soils up to 150 mg/kg. Inoculation of jute with Glomus mosseae and Glomus intraradices improved plant growth and enhanced anthracene removal in the presence of electrofused S. paucimobilis.

  9. Electron transmission through a class of anthracene aldehyde molecules

    NASA Astrophysics Data System (ADS)

    Petreska, Irina; Ohanesjan, Vladimir; Pejov, Ljupco; Kocarev, Ljupco

    2016-03-01

    Transmission of electrons via metal-molecule-metal junctions, involving rotor-stator anthracene aldehyde molecules is investigated. Two model barriers having input parameters evaluated from accurate ab initio calculations are proposed and the transmission coefficients are obtained by using the quasiclassical approximation. Transmission coefficients further enter in the integral for the net current, utilizing Simmons' method. Conformational dependence of the tunneling processes is evident and the presence of the side groups enhances the functionality of the future single-molecule based electronic devices.

  10. Cytochrome P450 monooxygenases involved in anthracene metabolism by the white-rot basidiomycete Phanerochaete chrysosporium.

    PubMed

    Chigu, Nomathemba Loice; Hirosue, Sinji; Nakamura, Chie; Teramoto, Hiroshi; Ichinose, Hirofumi; Wariishi, Hiroyuki

    2010-08-01

    Cytochrome P450 monooxygenases (P450s) involved in anthracene metabolism by the white-rot basidiomycete Phanerochaete chrysosporium were identified by comprehensive screening of both catalytic potentials and transcriptomic profiling. Functional screening of P. chrysosporium P450s (PcCYPs) revealed that 14 PcCYP species catalyze stepwise conversion of anthracene to anthraquinone via intermediate formation of anthrone. Moreover, transcriptomic profiling explored using a complementary DNA microarray system demonstrated that 12 PcCYPs are up-regulated in response to exogenous addition of anthracene. Among the up-regulated PcCYPs, five species showed catalytic activity against anthracene. Based upon both catalytic and transcriptional properties, these five species are most likely to play major roles in anthracene metabolic processes in vivo. Thus, the combination of functional screening and a microarray system may provide a novel strategy for obtaining a thorough understanding of the catalytic functions and biological impacts of PcCYPs.

  11. Alkyl chain length dependence of the field-effect mobility in novel anthracene derivatives.

    PubMed

    Back, Jang Yeol; An, Tae Kyu; Cheon, Ye Rim; Cha, Hyojung; Jang, Jaeyoung; Kim, Yebyeol; Baek, Yonghwa; Chung, Dae Sung; Kwon, Soon-Ki; Park, Chan Eon; Kim, Yun-Hi

    2015-01-14

    We report six asymmetric alkylated anthracene-based molecules with different alkyl side chain lengths for use in organic field-effect transistors (OFETs). Alkyl side chains can potentially improve the solubility and processability of anthracene derivatives. The crystallinity and charge mobility of the anthracene derivatives may be improved by optimizing the side chain length. The highest field-effect mobility of the devices prepared here was 0.55 cm(2)/(V s), for 2-(p-pentylphenylethynyl)anthracene (PPEA). The moderate side chain length appeared to be optimal for promoting self-organization among asymmetric anthracene derivatives in OFETs, and was certainly better than the short or long alkyl side chain lengths, as confirmed by X-ray diffraction measurements.

  12. Intramolecular triplet energy transfer in anthracene-based platinum acetylide oligomers.

    PubMed

    Li, Yongjun; Köse, Muhammet E; Schanze, Kirk S

    2013-08-01

    Platinum acetylide oligomers that contain an anthracene moiety have been synthesized and subjected to photophysical characterization. Spectroscopic measurement and DFT calculations reveal that both the singlet and triplet energy levels of the anthracene segment are lower than those of the platinum acetylide segment. Thus, the platinum acetylide segment acts as a sensitizer to populate the triplet state of the anthrancene segment via intramolecular triplet-triplet energy transfer. The objective of this work is to understand the mechanisms of energy-transfer dynamics in these systems. Fluorescence quenching and the dominant triplet absorption that arises from the anthracene segment in the transient absorption spectrum of Pt4An give clear evidence that energy transfer adopts an indirect mechanism, which begins with singlet-triplet energy transfer from the anthracene segment to the platinum acetylide segment followed by triplet-triplet energy transfer to the anthracene segment.

  13. Biodegradation of anthracene by a novel actinomycete, Microbacterium sp. isolated from tropical hydrocarbon-contaminated soil.

    PubMed

    Salam, Lateef B; Obayori, Oluwafemi S; Olatoye, Nojeem O

    2014-01-01

    A novel anthracene-degrading Gram-positive actinomycete, Microbacterium sp. strain SL10 was isolated from a hydrocarbon-contaminated soil at a mechanical engineering workshop in Lagos, Nigeria. The polluted soil had an unusually high total hydrocarbon content of 157 g/kg and presence of various heavy metals. The isolate tolerated salt concentration of more than 4%. It resisted cefotaxime, streptomycin and ciprofloxacin, but susceptible to meropenem, linezolid and vancomycin. The isolate exhibited growth rate and doubling time of 0.82 days(-1) and 0.84 days, respectively on anthracene. It degraded 57.5 and 90.12% of anthracene within 12 and 21 days, respectively while the rate of anthracene utilization by the isolate was 4.79 mg l(-1) d(-1). To the best of our knowledge, this is the first report of isolation and characterization of anthracene-degrading Microbacterium sp.

  14. Macrocrystals of Colloidal Quantum Dots in Anthracene: Exciton Transfer and Polarized Emission.

    PubMed

    Soran-Erdem, Zeliha; Erdem, Talha; Hernandez-Martinez, Pedro Ludwig; Akgul, Mehmet Zafer; Gaponik, Nikolai; Demir, Hilmi Volkan

    2015-05-07

    In this work, centimeter-scale macrocrystals of nonpolar colloidal quantum dots (QDs) incorporated into anthracene were grown for the first time. The exciton transfer from the anthracene host to acceptor QDs was systematically investigated, and anisotropic emission from the isotropic QDs in the anthracene macrocrystals was discovered. Results showed a decreasing photoluminescence lifetime of the donor anthracene, indicating a strengthening energy transfer with increasing QD concentration in the macrocrystals. With the anisotropy study, QDs inside the anthracene host acquired a polarization ratio of ~1.5 at 0° collection angle, and this increases to ~2.5 at the collection angle of 60°. A proof-of-concept application of these excitonic macrocrystals as tunable color converters on light-emitting diodes was also demonstrated.

  15. [Isolation of an anthracene-degrading strain Aspergillus fumigatus A10 and its degradation characteristics].

    PubMed

    Qiang, Jing; Yin, Hua; Peng, Hui; Ye, Jin-Shao; Qin, Hua-Ming; He, Bao-Yan; Zhang, Na

    2009-05-15

    An anthracene-degrading strain (A10) was isolated from contaminated environment and identified as Aspergillus fumigatus. The experimental results showed that the biodegradation rate of anthracene increased with the increasing time. Between 12-84 h interval, the biodegradation performed rapidly, while after this, the increase of biodegradation rate tended to become slow, and ultimately the biodegradation rate could achieve approximately 83%. The degradatinn rate of anthracene reached 79.37% within 5 days when the initial concentration of anthracene in mineral salts medium (MSM) was 10 mg/L, the inoculum dosage was 50 g/L (wet weight) and the cell age was 36 h. The concentration of anthracene had notable influence on degradation function of strain A10 and the highest degradation rate (92.17%) was achieved when anthracene concentration was 5 mg/L. The degradation rate could maintain about 60% with initial pH of MSM in the range of 5.0-7.5, and also, the anthracene could be better broken down when the temperature was 30 degrees C and dissolved oxygen was 4.30 mg/L. Certain amount of nutrition salts promoted the biodegradation of anthracene to some extent. Addition of lactose as co-metabolic substrate most favorably accelerated degradation of anthracene by about 37.15%. The mechanism research revealed that the biodegradation by strain A10 was a dynamic process in which extracellular sorption and intracellular degradation were included. FT-IR analysis exhibited that the structure of anthracene changed with the action of microbe, generating a series of metabolites, such as aromatic acid, aromatic ketone, aromatic aldehyde with one or two benzene rings, as well as saturated hydrocarbons.

  16. Infrared spectroscopy of fullerene C60/anthracene adducts

    NASA Astrophysics Data System (ADS)

    García-Hernández, D. A.; Cataldo, F.; Manchado, A.

    2013-09-01

    Recent Spitzer Space Telescope observations of several astrophysical environments such as planetary nebulae, reflection nebulae and R Coronae Borealis stars show the simultaneous presence of mid-infrared features attributed to neutral fullerene molecules (i.e. C60) and polycyclic aromatic hydrocarbons (PAHs). If C60 fullerenes and PAHs coexist in fullerene-rich space environments, then C60 may easily form adducts with a number of different PAH molecules, at least with catacondensed PAHs. Here we present the laboratory infrared spectra (˜2-25 μm) of C60 fullerene and anthracene Diels-Alder mono- and bis-adducts as produced by sonochemical synthesis. We find that C60/anthracene Diels-Alder adducts display spectral features strikingly similar to those from C60 (and C70) fullerenes and other unidentified infrared emission features. Thus, fullerene adducts - if formed under astrophysical conditions and are stable/abundant enough - may contribute to the infrared emission features observed in fullerene-containing circumstellar/interstellar environments.

  17. Complexation of pyrene and anthracene with human blood plasma

    NASA Astrophysics Data System (ADS)

    Saletskii, A. M.; Mel'Nikov, A. G.; Pravdin, A. B.; Kochubei, V. I.; Meln'ikov, G. V.

    2008-05-01

    We have studied the interaction between polycyclic aromatic hydrocarbons (pyrene and anthracene) with human serum albumin (HSA) and human blood plasma. We have shown that the increase in the fluorescence intensity and the decrease in the polarity index of pyrene on going from an aqueous solution to a pH 7.4 buffer solution of HSA suggests that polycyclic aromatic hydrocarbons are localized in the hydrophobic microphase of the proteins. The increase in the fluorescence intensity for anthracene and pyrene, and also the decrease in the polarity index of pyrene on going from HSA to blood plasma is connected with the fact that polycyclic aromatic hydrocarbons can bind both to plasma proteins and to plasma lipids. When sodium dodecyl sulfate (SDS) is added to the blood plasma in a concentration greater than the critical micelle concentration, we observe an increase in the fluorescence intensity and the polarity index of pyrene. We hypothesize that this is connected with localization of pyrene near the interface between the hydrophobic and hydrophilic phases of the protein-SDS system. We have established that SDS leads to a change in the structure of blood plasma proteins and promotes escape of polycyclic aromatic hydrocarbons from the protein globules.

  18. Approaching two-dimensional copolymers: photoirradiation of anthracene- and diaza-anthracene-bearing monomers in Langmuir monolayers.

    PubMed

    Payamyar, Payam; Servalli, Marco; Hungerland, Tim; Schütz, Andri P; Zheng, Zhikun; Borgschulte, Andreas; Schlüter, A Dieter

    2015-01-01

    By using structurally similar amphiphilic monomers, it is shown that compressed monolayers of varying amounts of such monomers at the air/water interface can be converted by photo-irradiation into the corresponding covalently connected monolayer sheets. Since one of the monomers carries three anthracene units and the other three 1,8-diaza-anthracene units, the growth reaction is proposed to take place through photochemically achieved [4+4]-cycloaddition between pairs of these units that are co-facially (face-to-face) arranged, to furnish the corresponding covalent dimers. While evidence for both homodimers is amply available, the existence of the heterodimer needs to be established with the help of a model reaction to support the conceptual aspect of this work, copolymerization in two dimensions. The sheet copolymers exhibit substantial robustness in that they can be spanned over 20 × 20 μm(2)-sized holes without rupturing under their own weight. X-ray photoelectron spectroscopy (XPS) studies reveal that the monomers are incorporated into the sheet copolymers according to feed. These results establish existence of the first covalent sheet copolymer, which is considered a step ahead towards novel 2D materials.

  19. Biodegradation of anthracene and benz[a]anthracene by two Fusarium solani strains isolated from mangrove sediments.

    PubMed

    Wu, Yi-Rui; Luo, Zhu-Hua; Vrijmoed, L L P

    2010-12-01

    An investigation was undertaken on the biodegradation of two kinds of polycyclic aromatic hydrocarbons (PAHs), anthracene (ANT) and benz[a]anthracene (BAA), by fungi isolated from PAH-contaminated mangrove sediments environment in Ma Wan, Hong Kong. ANT (50mg l(-1)) and BAA (20mg l(-1)), respectively, were added to mineral salt medium initially for screening of PAH-degrading fungi, and finally two fungal species capable of using ANT or BAA as the sole carbon source were isolated and identified as Fusariumsolani species. Removal of ANT and BAA reached 40% and 60% of the added amount, respectively, after 40 days of incubation. A total of six metabolites were isolated and characterized by solid phase microextraction (SPME) combined with gas chromatography-mass spectrometry (GC/MS), which indicate that F.solani degraded both ANT and BAA via their respective quinone molecules to generate phthalic acid. Free extracellular laccase was detected during the degradation process without detectable lignin peroxidase (LiP) and manganese-dependent peroxidase (MnP), suggesting that laccase might play an important role in the transformation of PAHs compounds.

  20. Mixing of an anthracene-contaminated soil: a simple but efficient remediation technique?

    PubMed

    Delgado-Balbuena, Laura; Aguilar-Chávez, Ángel R; Luna-Guido, Marco L; Dendooven, Luc

    2013-10-01

    Contamination of soils with polycyclic aromatic hydrocarbons (PAHs) is a serious problem in petroleum producing countries, such as México, and environment-friendly easy to apply techniques are required to accelerate the removal of the contaminants. Removal of anthracene was monitored in an arable and a pasture soil regularly mixed or amended with organic material, a non-ionic surfactant (Surfynol(®) 485) or earthworms (Eisenia fetida (Savigny, 1826)). In both soils the same results were obtained although the removal of anthracene was faster from the pasture than from the arable soil. The fastest removal of anthracene was obtained when the soil was mixed every 7 days and no contaminant was detected in both soils after 56 days. The second fastest removal of anthracene was obtained when earthworms were added to soil and no contaminant was detected in both soils after 112 days. Application of organic material that served as feed for the earthworms also accelerated the removal of the contaminant compared to the unamended soil, but application of the surfactant inhibited the dissipation of the contaminant. Only 37% of the spiked anthracene was removed from soil when surfactant was applied, while 62% was dissipated in the unamended soil after 112 days. It was found that simply mixing a soil removed anthracene faster than when earthworms were applied, while the application of the surfactant inhibited the removal of anthracene by the autochthonous soil microorganisms.

  1. Bioaccumulation and depuration of anthracene in Penaeus monodon (Fibricius) through food ingestion.

    PubMed

    Ong, Pei Thing; Yong, Jaw Chuen; Chin, Kam Yew; Hii, Yii Siang

    2011-07-01

    Understanding on the bioaccumulation and depuration of PAHs (polycyclic aromatic hydrocarbons) in Penaeus monodon is important in seafood safety because it is one of the most popular seafood consumed worldwide. In this study, we used anthracene as the precursor compound for PAHs accumulation and depuration in the shrimp. Commercial feed pellets spiked with anthracene were fed to P. monodon. At 20 mg kg(-1) anthracene, P. monodon accumulated 0.1% of the anthracene from the feed. P. monodon deputed the PAH two times faster than its accumulation. The shrimp reduced its feed consumption when anthracene content in the feed exceeded 20 mg kg(-1). At 100 mg kg(-1) anthracene, P. monodon started to have necrosis tissues on the posterior end of their thorax. The bioaccumulation factor (BAF), uptake rate constant (k(1)) and depuration rate constant (k(2)) of anthracene in P. monodon were 1.15×10(-3), 6.80×10(-4) d(-1) and 6.28×10(-1) d(-1), respectively. The depuration rate constant is about thousand times higher than the uptake rate constant and this indicated that this crustacean is efficient in depurating hydrocarbons from their tissue.

  2. Studies on organic semiconductors. 15: Effects of the substituents on the photoconductivities of substituted anthracenes

    NASA Technical Reports Server (NTRS)

    Sugimoto, A.; Kato, S.; Inoue, H.; Imoto, E.

    1985-01-01

    The photocurrents of the substituted anthracenes, 1,5-diacetylanthracene (2), 1-acetylanthracene (3), 9-acetylanthracene (4), 1,5-dichloroanthracene (5), 1,5-diethylanthracene (6), 1,5-dimethoxyanthracene (7), 9-cyanoanthracene (8), and anthracene (1) were measured by using their surface type cells in nitrogen. The compounds of (1), (5), (6), (7), and (8) showed the photocurrent spectra which corresponded to the absorption spectra of their evaporated films. In the cases of (2) and (3), however, the anomalous photocurrent appeared in the threshold region of their absorption spectra. The appearance of the anomalous photocurrent was characteristic of anthracenes having the acetyl group at 1- and/or 5-position. The magnitude of the photocurrents of the 1,5-disubstituted anthracenes was similar to that of (1). The photocurrents of the monosubstituted anthracenes were smaller than that of (1). Among the monosubstituted anthracenes, the compound (4) showed no photocurrent under the same conditions. Contrary to the results obtained in the cases of phenazines, the photoconductivities of the anthracene derivatives became better in air.

  3. Degradation and transformation of anthracene by white-rot fungus Armillaria sp. F022.

    PubMed

    Hadibarata, Tony; Zubir, Meor Mohd Fikri Ahmad; Rubiyatno; Chuang, Teh Zee; Yusoff, Abdull Rahim Mohd; Salim, Mohd Razman; Fulazzaky, Mohammad Ali; Seng, Bunrith; Nugroho, Agung Endro

    2013-09-01

    Characterization of anthracene metabolites produced by Armillaria sp. F022 was performed in the enzymatic system. The fungal culture was conducted in 100-mL Erlenmeyer flask containing mineral salt broth medium (20 mL) and incubated at 120 rpm for 5-30 days. The culture broth was then centrifuged at 10,000 rpm for 45 min to obtain the extract. Additionally, the effect of glucose consumption, laccase activity, and biomass production in degradation of anthracene were also investigated. Approximately, 92 % of the initial concentration of anthracene was degraded within 30 days of incubation. Dynamic pattern of the biomass production was affected the laccase activity during the experiment. The biomass of the fungus increased with the increasing of laccase activity. The isolation and characterization of four metabolites indicated that the structure of anthracene was transformed by Armillaria sp. F022 in two routes. First, anthracene was oxidized to form anthraquinone, benzoic acid, and second, converted into other products, 2-hydroxy-3-naphthoic acid and coumarin. Gas chromatography-mass spectrometry analysis also revealed that the molecular structure of anthracene was transformed by the action of the enzyme, generating a series of intermediate compounds such as anthraquinone by ring-cleavage reactions. The ligninolytic enzymes expecially free extracellular laccase played an important role in the transformation of anthracene during degradation period.

  4. A procedure for the joint evaluation of substrate partitioning and kinetic parameters for reactions catalyzed by enzymes in reverse micellar solutions. I. Hydrolysis of 2-naphthyl acetate catalyzed by lipase in sodium 1,4-bis(2-ethylhexyl) sulphosuccinate (AOT)/buffer/heptane.

    PubMed

    Aguilar, L F; Abuin, E; Lissi, E

    2001-04-15

    A simple method useful for the joint evaluation of substrate partitioning and kinetic parameters for reactions catalyzed by enzymes entrapped in reverse micelles is proposed. The method is applied to the hydrolysis of 2-naphthyl acetate (2-NA) catalyzed by lipase in sodium 1,4-bis(2-ethylhexyl) sulfosuccinate (AOT)/buffer/heptane reverse micellar solutions. In the presence of micelles, the relationship between the initial reaction rate and the analytical concentration of 2-NA was dependent on AOT concentration at a constant W ([water]/[AOT]) value. The dependence of the initial reaction rate profiles with [AOT] was analyzed according with the method proposed to obtain the partition constant of 2-NA between the micelles and the external solvent, Kp. A value of Kp = 2.7 L mol(-1) was obtained irrespective of the water content of the micelles (W from 5 to 20). The catalytic rate constant kcat in the micellar solutions was independent of [AOT] but slightly decreased with an increase in W from 2 x 10(-6) mol g(-1) s(-1) at W = 5 to 1.2 x 10(-6) mol g(-1) s(-1) at W = 20. The apparent Michaelis constant determined in terms of the analytical concentration of 2-NA increased with [AOT] at a given W and moderately decreased with W at a fixed [AOT]. The increase with [AOT] is accounted for by considering the partitioning of the substrate. After correction for the partitioning of 2-NA values of (Km)corr were obtained as 3.9 x 10(-3) mol L(-1) (W = 5), 4.6 x 10(-3) mol L(-1) (W = 10), 2.3 x 10(-3) mol L(-1) (W = 15), and 1.7 x 10(-3) mol L(-1) (W = 20). The rate parameters in the aqueous phase in the absence of micelles, were obtained as (kcat)aq = 7.9 x 10(-6) mol g(-1) s(-1) and (Km)aq = 2.5 x 10(-3) mol L(-1). In order to compare the efficiency of the enzyme in the micellar solution with that in aqueous phase, the values of (Km)corr were in turn corrected to take into account differences in the substrate activity, obtaining so a set of (Km)*corr values. The efficiency of the

  5. New anthracene-tetrathiafulvalene derivative-encapsulated SWNT nanocomposite and its application for biosensing.

    PubMed

    Song, Min; Wang, Xuemei; Liu, Wei; Zuo, Jinglin

    2010-03-01

    In this study, a novel anthracene-tetrathiafulvalene derivative has been synthesized and immobilized on single-walled carbon nanotubes through non-covalent sidewall functionalization. The new anthracene-tetrathiafulvalene (TTF) derivative-encapsulated SWNT nanocomposites were characterized using SEM, TEM, and Raman spectra and were utilized for biomolecular recognition. Our observations demonstrate that the new anthracene-TTF derivative-encapsulated SWNT nanocomposites can readily facilitate the biosensing and sensitive detection of DNA, which could be further explored for promising applications in bioelectronics and biosensors.

  6. Extraction of anthracene and benzo(a)pyrene from soil

    SciTech Connect

    Fowlie, P.J.A.; Bulman, T.L.

    1986-04-01

    Extraction of /sup 14/C labeled benzo(a)pyrene and anthracene from contaminated soil samples by Soxhlet and Polytron techniques was studied in a replicated 2/sup 4/ factorial experiment. Soxhlet extraction gave higher recoveries than Polytron extraction. Percent recoveries from both techniques were greater at a 50 /sup +/g/g contamination level than at 5/sup +/g/g. Pyrolysis of the extracted residue followed by trapping of /sup 14/CO/sub 2/ corroborated the extraction results. In addition, analysis of the residue showed a significant increase in /sup 14/C due to soil sterilization with HgCl/sub 2/ and an interaction effect between PAH and concentration. The effects of PAH, concentration, and HgCl/sub 2/ treatment on extraction and sorption were the same with both extraction methods. 6 references, 3 tables.

  7. Evaluation of natural anthracene-derived compounds as antimitotic agents.

    PubMed

    Badria, Farid A; Ibrahim, Ahmed S

    2013-04-01

    Plants that contain anthracene-derived compounds such as anthraquinones have been reported to act as anticancer besides their use for millennia to treat constipation, but the mechanism of action is still unfolding. Therefore we pursue this study to explore a new horizon in the anticancer property of these agents with relevance to mitotic arrest. To achieve this goal, the antimitotic activity of a series of naturally occurring anthracene-derived anthraquinones including anthrone, alizarin (1,2-dihydroxyanthraquinone), quinizarin (1,4-dihydroxyanthraquinone), rhein (4,5-dihydroxyanthraquinone-2-carboxylic acid), emodin (1,6,8-trihydroxy-3-methylanthraquinone), and aloe emodin (1,8-dihydroxy-3-hydroxymethylanthraquinone) were evaluated using Allium cepa root tips. Initial results revealed that the mitosis was inhibited after 3, 6, and 24 h, respectively, of incubation with 500, 250, and 125 ppm of each compound in a dose-dependent manner. Furthermore, alizarin at 500 ppm was proved to be the most active compound to arrest the mitosis after 24 h followed by emodin, aloe emodin, rhein, and finally quinizarin. Interestingly, this inhibition of mitosis was irreversible in root tips incubated with each compound at concentration of 500 ppm but not with 250 ppm or 125 ppm, where the roots regained their normal mitotic activity after 96 h post-incubation in water. This re-evaluation of an old remedy suggests that several bioactive anthraquinones possess promising anti-mitotic activity that may have the potential to be lead compounds for the development of a new class of multifaceted natural anticancer/antimitotic agents.

  8. Competition between singlet fission and charge separation in solution-processed blend films of 6,13-bis(triisopropylsilylethynyl)pentacene with sterically-encumbered perylene-3,4:9,10-bis(dicarboximide)s.

    PubMed

    Ramanan, Charusheela; Smeigh, Amanda L; Anthony, John E; Marks, Tobin J; Wasielewski, Michael R

    2012-01-11

    The photophysics and morphology of thin films of N,N-bis(2,6-diisopropylphenyl)perylene-3,4:9,10-bis(dicarboximide) (1) and the 1,7-diphenyl (2) and 1,7-bis(3,5-di-tert-butylphenyl) (3) derivatives blended with 6,13-bis(triisopropylsilylethynyl)pentacene (TIPS-Pn) were studied for their potential use as photoactive layers in organic photovoltaic (OPV) devices. Increasing the steric bulk of the 1,7-substituents of the perylene-3,4:9,10-bis(dicarboximide) (PDI) impedes aggregation in the solid state. Film characterization data using both atomic force microscopy and X-ray diffraction showed that decreasing the PDI aggregation by increasing the steric bulk in the order 1 < 2 < 3 correlates with a decrease in the density/size of crystalline TIPS-Pn domains. Transient absorption spectroscopy was performed on ~100 nm solution-processed TIPS-Pn:PDI blend films to characterize the charge separation dynamics. These results showed that selective excitation of the TIPS-Pn results in competition between ultrafast singlet fission ((1*)TIPS-Pn + TIPS-Pn → 2 (3*)TIPS-Pn) and charge transfer from (1*)TIPS-Pn to PDIs 1-3. As the blend films become more homogeneous across the series TIPS-Pn:PDI 1 → 2 → 3, charge separation becomes competitive with singlet fission. Ultrafast charge separation forms the geminate radical ion pair state (1)(TIPS-Pn(+•)-PDI(-•)) that undergoes radical pair intersystem crossing to form (3)(TIPS-Pn(+•)-PDI(-•)), which then undergoes charge recombination to yield either (3*)PDI or (3*)TIPS-Pn. Energy transfer from (3*)PDI to TIPS-Pn also yields (3*)TIPS-Pn. These results show that multiple pathways produce the (3*)TIPS-Pn state, so that OPV design strategies based on this system must utilize this triplet state for charge separation.

  9. Interface Engineering of Metal Oxides using Ammonium Anthracene in Inverted Organic Solar Cells.

    PubMed

    Jeon, Il; Zeljkovic, Sasa; Kondo, Kei; Yoshizawa, Michito; Matsuo, Yutaka

    2016-11-09

    In this work, by casting water-soluble ammonium anthracene on metal oxides, the organic surface modifier re-engineered the interface of the metal oxide to improve charge transport. The energy level of ammonium anthracene increased the work function of indium tin oxide (ITO), functioning as a hole-blocker (electron-transporter). Solar cells in which ITO was treated by the ammonium anthracene produced an average power conversion efficiency (PCE) of 5.8% without ZnO, the electron-transporting layer. When the ammonium anthracene was applied to ZnO, an average PCE of 8.1% was achieved, which is higher than the average PCE of 7.5% for nontreated ZnO-based devices.

  10. Combined Quenching Mechanism of Anthracene Fluorescence by Cetylpyridinium Chloride in Sodium Dodecyl Sulfate Micelles.

    PubMed

    Soemo, Angela R; Pemberton, Jeanne E

    2014-03-01

    The Stern-Volmer quenching constant (KSV) for quenching of anthracene fluorescence in sodium dodecyl sulfate (SDS) micelles by pyridinium chloride has been reported previously to be 520 M(-1) based on steady state fluorescence measurements. However, such measurements cannot distinguish static versus dynamic contributions to the overall quenching. In the work reported here, the quenching dynamics of anthracene in SDS micelles by cetylpyridinium chloride (CPC), an analogue of pyridinium chloride, were investigated using both steady state and time resolved fluorescence quenching. Concurrent measurement of the decrease in fluorescence intensity and lifetime of anthracene provide a quantitative evaluation of collision induced (i.e. dynamic) versus complex formation (i.e. static) quenching of the anthracene fluorophore. The results reveal that a combined quenching mechanism is operative with approximately equal constants of 249 ± 6 M(-1) and 225 ± 12 M(-1) for dynamic and static quenching, respectively.

  11. Biodegradation of naphthalene and anthracene by chemo-tactically active rhizobacteria of populus deltoides

    PubMed Central

    Bisht, Sandeep; Pandey, Piyush; Sood, Anchal; Sharma, Shivesh; Bisht, N. S.

    2010-01-01

    Several naphthalene and anthracene degrading bacteria were isolated from rhizosphere of Populus deltoides, which were growing in non-contaminated soil. Among these, four isolates, i.e. Kurthia sp., Micrococcus varians, Deinococcus radiodurans and Bacillus circulans utilized chrysene, benzene, toluene and xylene, in addition to anthracene and naphthalene. Kurthia sp and B. circulans showed positive chemotactic response for naphthalene and anthracene. The mean growth rate constant (K) of isolates were found to increase with successive increase in substrate concentration (0.5 to 1.0 mg/50ml). B. circulans SBA12 and Kurthia SBA4 degraded 87.5% and 86.6% of anthracene while, Kurthia sp. SBA4, B. circulans SBA12, and M. varians SBA8 degraded 85.3 %, 95.8 % and 86.8 % of naphthalene respectively after 6 days of incubation as determined by HPLC analysis. PMID:24031572

  12. Development of fluorescent lead II sensor based on an anthracene derived chalcone.

    PubMed

    Prabhu, J; Velmurugan, K; Nandhakumar, R

    2015-06-05

    A simple anthracene based chalcone as a fluorescent chemosensor 1, capable of detecting Pb(2+) in aqueous media, has been synthesized by the reaction between pyridine 2-carboxaldehyde and 9-acetyl anthracene. The Pb(2+) recognition processes follows a photo induced electron transfer (PET) mechanism and are scarcely influenced by other coexisting metal ions. In addition, determination of lead in a variety of samples was also determined.

  13. Biochemical response of anthracene and benzo [a] pyrene in milkfish Chanos chanos.

    PubMed

    Palanikumar, L; Kumaraguru, A K; Ramakritinan, C M; Anand, M

    2012-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are common toxic pollutants found in the aquatic environment, and the assessment of their impact on biota is of considerable concern. The aim of the present research was to study the acute toxicity, bioaccumulation and biochemical response of milkfish Chanos chanos (Forsskal) to two selected PAHs: anthracene and benzo [a] pyrene. Acute toxicity test results were evaluated by the Probit analysis method and 96h LC(50) values for C. chanos exposed to anthracene was 0.030mgl(-1) and 0.014mgl(-1) for benzo [a] pyrene. Bioaccumulation concentration of anthracene was high when compared to benzo [a] pyrene. Biomarkers indicative of neurotoxicity (acetylcholinesterase, AchE), oxidative stress (lipid peroxidation, LPO and catalase, CAT) and phase II biotransformation of xenobiotics (glutathione S transferase, GST and reduced glutathione, GSH) were measured to assess effects of selected PAHs. Anthracene and benzo [a] pyrene increase LPO and CAT level of C. chanos suggesting that these PAHs may induce oxidative stress. Both the PAHs inhibited AchE indicating that they have at least one mechanism of neurotoxicity in common: the disruption of cholinergic transmission by inhibition of AChE. An induction of C. chanos glutathione S-transferase (GST) activity was found in fish exposed to benzo [a] pyrene, while an inhibition was observed after exposure to anthracene. These results suggest that GST is involved in the detoxification of benzo [a] pyrene, but not of anthracene.

  14. Impact of moisture dynamic and sun light on anthracene removal from soil.

    PubMed

    Vázquez Núñez, Edgar; García Gaytán, Alejandro; Luna-Guido, M; Marsch, R; Dendooven, L

    2009-04-01

    In a previous study, remediation of anthracene from soil was faster in the top 0-2 cm layer than in the lower soil layers. It was not clear whether this faster decrease was due to biotic or abiotic processes. Anthracene-contaminated soil columns were covered with black or transparent perforated polyethylene so that aeration occurred but that fluctuations in water content were minimal and light could reach (LIGHT treatment) or not reach the soil surface (DARK treatment), or left uncovered so that soil water content fluctuate and light reached the soil surface (OPEN treatment). The amount of anthracene, microbial biomass C, and microbial activity as reflected by the amount of CO(2) produced within 3 days were determined in the 0-2 cm, 2-8 cm, and 8-15 cm layer after 0, 3, 7, 14, and 28 days. In the 0-2 cm layer of the OPEN treatment, 17% anthracene remained, 48% in the LIGHT treatment and 61% in the DARK treatment after 28 days. In the 2-8 cm and 8-15 cm layer, treatment had no significant effect on the dissipation of anthracene from soil after 14 and 28 days. It was found that light and fluctuations in water content stimulated the removal of anthracene from the top 0-2 cm soil layer, but not from the lower soil layers. It can be speculated that covering contaminated soil or piling it up will inhibit the dissipation of the contaminant.

  15. Breakdown products on metabolic pathway of degradation of benz[a]anthracene by a ligninolytic fungus.

    PubMed

    Cajthaml, Tomás; Erbanová, Pavla; Sasek, Václav; Moeder, Monika

    2006-07-01

    Cultures of the ligninolytic fungus Irpex lacteus incubated in a nutrient liquid medium degraded more than 70% of the initially applied benz[a]anthracene within 14 days. At the first step of metabolization, benz[a]anthracene was transformed via a typical pathway of ligninolytic fungi to benz[a]anthracene-7,12-dione (BaAQ). The product was further transformed by at least two ways, whereas one is complied with the anthracene metabolic pathway of I. lacteus. Benz[a]anthracene-7,12-dione was degraded to 1,2-naphthalenedicarboxylic acid and phthalic acid that was followed with production of 2-hydroxymethyl benzoic acid or monomethyl and dimethylesters of phthalic acid. Another degradation product of BaAQ was identified as 1-tetralone. Its transformation via 1,4-naphthalenedione, 1,4-naphthalenediol and 1,2,3,4-tetrahydro-1-hydroxynaphthalene resulted again in phthalic acid. None of the intermediates were identified as dead-end metabolites. Metabolites produced by ring cleavage of benz[a]anthracene using the ligninolytic fungus are firstly presented in this work.

  16. ZnO/anthracene based inorganic/organic nanowire heterostructure: Photoresponse and photoluminescence studies

    SciTech Connect

    Dhara, Soumen; Giri, P. K.

    2012-02-15

    The effects of surface modification of vertically aligned ZnO nanowires (NWs) with anthracene for the improved photocurrent, photoresponse, and UV photoluminescence have been investigated in this work. The formation of ZnO/anthracene based inorganic/organic NWs heterostructure by surface capping with anthracene solution was confirmed from the high resolution transmission electron microscopy and Fourier transport infrared spectroscopy analyses. After the anthracene capping of ZnO NWs, despite an increase in dark current, we obtained a significant improvement in the photocurrent and photoresponsivity. A sixfold improvement in the UV photocurrent-to-dark current ratio is obtained with capping. Compared to the uncapped NWs, the photoresponse is significantly faster for the ZnO/anthracene system with response and reset times of 1.5 and 1.6 s, respectively. The room temperature photoluminescence spectra show threefold enhanced UV emission with large enhancement in the ratio of UV to green emission intensities. The faster photoresponse and enhanced photocurrent from the ZnO/anthracene heterostructure are explained on the basis of modification of surface defects and interfacial charge transfer process.

  17. Syntheses and Chemosensory of Anthracene and Phenanthrene Bisimide Derivatives

    NASA Technical Reports Server (NTRS)

    Bogusz, Zachary A.

    2004-01-01

    As the present technology of biochemical weapons advances, it is essential for science to attempt to prepare our nation for such an occurrence. Various areas of current research are devoted to precautionary measures and potential antidotes for national security. A practical application of these precautions would be the development of a chemical capable of detecting harmful gas. The benefits of being capable to synthesis a chemical compound that would warn and identify potentially deadly gases would ensure a higher level of safety. The chemicals in question can be generalized as bisimide anthracene derivatives. The idea behind these compounds is that in the presence of certain nerve gases, the compound will actually fluoresce, giving an indication that there is a strong likelihood of the presence of a nerve gas and ensure the proper precautionary measures are taken. The fluorescence is due to the quenching of an electric proton transfer within the structure of the molecule. The system proves to be very unique on account of the fact that the fluorescence can be "turned off" by reducing the system. By utilizing the synthesis designed by Dr. Faysal Ilhan, four distinct compounds can be synthesized through photochemical reactions involving para- and ortho- diketones. The photochemistry involved is very modem and much research is being devoted to fully understanding the possibilities and alternative applications of such materials. and meta-nitro anthracene bisimide (ABI-NO2), the amine of each (ABI-NH2), a para- and meta-nitro phenanthrene bisimjde (PBI-NO2), and the amine of each (PBI-NH2). Upon synthesizing these distinct compounds, I must then purify and analyze them in order to obtain any relevant trends, behaviors, and characteristics. The chemical composition analyses that will be conducted are the procedures taken by Dr. Daniel Tyson on previous experiments. The results generated from the data will point further research in the correct direction and hopefully

  18. Long-term reproductive and behavioral toxicity of anthracene to fish in the presence of solar ultraviolet radiation

    SciTech Connect

    Hall, A.T.; Oris, J.T.

    1994-12-31

    The long-term, low-level effects of anthracene in the presence of solar ultraviolet radiation (SUVR) were examined in the fathead minnow (Pimephales promelas). Adult fish exposed to anthracene exhibited reduced egg laying capacity, with altered oocyte maturation as a potential mechanism of action. Eggs and larvae maternally exposed to anthracene exhibited reduced hatching success and severe developmental abnormalities when incubated under SUVR. The combination of reduced egg output and developmental effects resulted in an inhibition in reproductive capacity in the range of 70--100%. Maternal transfer of anthracene to eggs was efficient; the BCF was 717 for maternally exposed eggs. However, anthracene deputation from eggs after oviposition with only maternal PAH exposure was rapid; anthracene half-life from eggs equaled 1.3 days. Exposure to anthracene under SUVR altered locomotor activity patterns in fathead minnows by inducing hyperactivity or hypoactivity during the light or dark phases of the photoperiod, respectively. Altered activity patterns indicated potential effects of anthracene on the nervous system and/or pineal gland. These alterations disrupted normal activity patterns and reproductive behaviors, and thus have major implications on a fish`s ability to survive and reproduce. Anthracene, a model phototoxic PAH, has many potential sites of toxic action, and any organism exposed to such contaminants will be an considerable SUVR-enhanced risk in the environment.

  19. Effects of anthracene on development of an arbuscular mycorrhizal fungus and contribution of the symbiotic association to pollutant dissipation.

    PubMed

    Verdin, A; Lounès-Hadj Sahraoui, A; Fontaine, J; Grandmougin-Ferjani, A; Durand, R

    2006-09-01

    The influence of anthracene, a low molecular weight polycyclic aromatic hydrocarbon (PAH), on chicory root colonization by Glomus intraradices and the effect of the root colonization on PAH degradation were investigated in vitro. The fungus presented a reduced development of extraradical mycelium and a decrease in sporulation, root colonization, and spore germination when exposed to anthracene. Mycorrhization improved the growth of the roots in the medium supplemented containing 140 mg l(-1) anthracene, suggesting a positive contribution of G. intraradices to the PAH tolerance of roots. Anthracene disappearance from the culture medium was quantified; results suggested that nonmycorrhizal chicory roots growing in vitro were able to contribute to anthracene dissipation, and in addition, that mycorrhization significantly enhanced anthracene dissipation. These monoxenic experiments demonstrated a positive contribution of the symbiotic association to anthracene dissipation in the absence of other microorganisms. In addition to anthracene dissipation, intracellular accumulation of anthracene was detected in lipid bodies of plant cells and fungal hyphae, indicating intracellular storage capacity of the pollutant by the roots and the mycorrhizal fungus.

  20. Oxidation of anthracene by immobilized laccase from Trametes versicolor.

    PubMed

    Hu, Xiaoke; Wang, Peng; Hwang, Huey-min

    2009-11-01

    The laccase of Trametes versicolor was immobilized on the functionalized nanoparticles SBA-15 with the average diameter less than 10 nm. Laccase mediated oxidations of anthracene (ANT) were investigated in the presence of two mediators, 2,2'-azino-bis-(3-ethylbenzothiazoline-6-sulphonic acid) diammonium salt (ABTS) and 1-hydroxybenzotriazole (HBT). Oxidation of ANT was more efficiently enhanced by adding 1 mM of HBT than that by adding ABTS. After 48 h oxidation HBT group significantly oxidized ANT with residue 58% relative to 88% in the ABTS group. HPLC and GC/MS analyses indicated the main product of ANT oxidation was anthraquinone (ANQ). The fluorescein diacetate (FDA) uptake of two human cell lines was used to assess the cytotoxicity and genotoxicity of ANT and ANQ. Treatments with ANT and ANQ at 5 and 10 microM exhibited significant cytotoxicity to the HaCaT cells and the A3 lymphocytes and no significant genotoxicity was observed. The results illustrated that ANQ is less toxic than ANT as well.

  1. Modeling, Synthesis and Biological Evaluation of Potential Retinoid-X-Receptor (RXR) Selective Agonists: Novel Analogs of 4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethynyl]benzoic Acid (Bexarotene) and (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)-4-hydroxyphenyl)acrylic acid (CD3254)

    PubMed Central

    Jurutka, Peter W.; Kaneko, Ichiro; Yang, Joanna; Bhogal, Jaskaran S.; Swierski, Johnathon C.; Tabacaru, Christa R.; Montano, Luis A.; Huynh, Chanh C.; Jama, Rabia A.; Mahelona, Ryan D.; Sarnowski, Joseph T.; Marcus, Lisa M.; Quezada, Alexis; Lemming, Brittney; Tedesco, Maria A.; Fischer, Audra J.; Mohamed, Said A.; Ziller, Joseph W.; Ma, Ning; Gray, Geoffrey M.; van der Vaart, Arjan; Marshall, Pamela A.; Wagner, Carl E.

    2014-01-01

    Three unreported analogs of 4-[1-(3,5,5,8,8-pentamethyl-5-6-7-8-tetrahydro-2-naphthyl)ethynyl]benzoic acid (1), otherwise known as bexarotene, as well as four novel analogs of (E)-3-(3-(1,2,3,4-tetrahydro-1,1,4,4,6-pentamethylnaphthalen-7-yl)-4-hydroxyphenyl)acrylic acid (CD3254) are described, and evaluated for their retinoid-X-receptor (RXR)-selective agonism. Compound 1 has FDA approval as a treatment for cutaneous T-cell lymphoma (CTCL); though, treatment with 1 can elicit side-effects by disrupting other RXR-heterodimer receptor pathways. Of the 7 modeled novel compounds, all analogs stimulate RXR-regulated transcription in mammalian-2-hybrid and RXRE-mediated assays, possess comparable or elevated biological activity based on EC50 profiles, and retain similar or improved apoptotic activity in CTCL assays compared to 1. All novel compounds demonstrate selectivity for RXR and minimal crossover onto the retinoic-acid-receptor (RAR) compared to all-trans-retinoic acid, with select analogs also reducing inhibition of other RXR-dependent pathways (e.g., VDR-RXR). Our results demonstrate that further improvements in biological potency and selectivity of bexarotene can be achieved through rational drug design. PMID:24180745

  2. Preparation of low toxicity pitches by thermal oxidative condensation of anthracene oil.

    PubMed

    Alvarez, Patricia; Granda, Marcos; Sutil, Juan; Santamaría, Ricardo; Blanco, Clara; Menéndez, Rosa; José Fernández, Juan; Viña, José Antonio

    2009-11-01

    This article describes a novel industrial procedure for producing new pitches of low toxicity from anthracene oil, a byproduct of coal tar distillation. The procedure involves oxidative treatment in order to polymerize and condense the anthracene oil components followed by thermal treatment and distillation in order to obtain a pitch with the desired parameters. This sequence (oxidative treatment/thermal treatment/distillation) was repeated four times under reaction conditions of increasing severity in four cycles of anthracene oil processing to obtain the four pitches. The pitches had similar characteristics to those of standard binder coal tar pitches (e.g., softening point and wetting capacity). Because of the inherent composition of the parent anthracene oil, the pitches were found to be totally free of solid particles, i.e., primary quinoline insolubles and metals. The gas chromatography and gas chromatography/mass spectroscopy results revealed a consecutive decrease in toxicity with successive cycles of anthracene oil processing. Thus, the benzo[a]pyrene content decreased from 11.2 mg/g for the pitch in cycle one to 1.5 mg/g for the pitch with four processing cycles. The carcinogenicity of the pitches, evaluated on the basis of benzo[a]pyrene toxic equivalency factors, also followed the same tendency. The final carcinogenity values are nearly all lower than those of standard binder coal tar pitches.

  3. Influences of humic acid and fulvic acid on horizontal leaching behavior of anthracene in soil barriers.

    PubMed

    Yu, Sheng; Li, Bang-Yu; Chen, Yi-Hu

    2015-12-01

    The influences of humic acid (HA) and fulvic acid (FA) on horizontal leaching behaviors of anthracene in barriers were investigated. Soil colloids (≤1 μm) were of concern because of their abilities of colloid-facilitated transport for hydrophobic organic compounds with soluble and insoluble organic matters. Through freely out of the barriers in the presence of soil colloids with FA added, the higher concentrations of anthracene were from 320 μg L(-1) (D1 and D3) to 390 μg L(-1) (D2 and D4) with 1 to 20 cm in length. The contents of anthracene were distributed evenly at 25 ng g(-1) dry weight (DW) (D1 and D3) and 11 ng g(-1) DW (D2 and D4) in barriers. Therefore, anthracene leaching behaviors were mainly induced by soil colloids with soluble organic matters. The insoluble organic matters would facilitate anthracene onto soil colloids and enhance the movement in and through porous media of soil matrix.

  4. Biostimulation Reveals Functional Redundancy of Anthracene-Degrading Bacteria in Polycyclic Aromatic Hydrocarbon-Contaminated Soil.

    PubMed

    Dunlevy, Sage R; Singleton, David R; Aitken, Michael D

    2013-11-01

    Stable-isotope probing was previously used to identify bacterial anthracene-degraders in untreated soil from a former manufactured gas plant site. However, subsequent pyrosequence analyses of total bacterial communities and quantification of 16S rRNA genes indicated that relative abundances of the predominant anthracene-degrading bacteria (designated Anthracene Group 1) diminished as a result of biological treatment conditions in lab-scale, aerobic bioreactors. This study identified Alphaproteobacterial anthracene-degrading bacteria in bioreactor-treated soil which were dissimilar to those previously identified. The largest group of sequences was from the Alterythrobacter genus while other groups of sequences were associated with bacteria within the order Rhizobiales and the genus Bradyrhizobium. Conditions in the bioreactor enriched for organisms capable of degrading anthracene which were not the same as those identified as dominant degraders in the untreated soil. Further, these data suggest that identification of polycyclic aromatic hydrocarbon-degrading bacteria in contaminated but untreated soil may be a poor indicator of the most active degraders during biological treatment.

  5. Green synthesis and characterization of ZnO nanoparticles for photocatalytic degradation of anthracene

    NASA Astrophysics Data System (ADS)

    Hassan, Saad S. M.; El Azab, Waleed I. M.; Ali, Hager R.; Mansour, Mona S. M.

    2015-12-01

    Zinc oxide nanoparticles were prepared using corriandrum sativum leaf extract and zinc acetate dihydrate. It was utilized as a photocatalyst for the degradation of anthracene. The catalyst was characterized by x-ray diffraction, high-resolution transmission electron microscopy, scanning electron microscopy, dynamic scattering light, Raman spectrometry and UV-vis spectrophotometry. The catalyst was used in a bench-scale design for degradation of anthracene. The factors affecting the photocatalytic degradation efficiency, including irradiation time, loading catalyst doses, and initial concentration of anthracene were investigated. The results obtained showed that the photocatalytic degradation efficiency was increased with both the decrease of the initial anthracene concentration and the increase of the photocatalyst doses. The optimum photocatalytic degradation was obtained at pH 7, irradiation time of 240 min and loading catalyst dose of 1000 μg L-1. Under these conditions, the photocatalytic degradation percentage of anthracene was 96%. The byproduct was the much less toxic (9, 10-anthraquinone) and a small amount of phthalic acid as confirmed by gas mass spectrometry and high-pressure liquid chromatography. The kinetic studies revealed that the photocatalytic degradation process obeyed the Langmuir-Hinshelwood model and followed a pseudo-first-order rate expression.

  6. Ionic liquid crystals formed by self-assembly around an anionic anthracene core.

    PubMed

    Olivier, Jean-Hubert; Camerel, Franck; Barberá, Joaquín; Retailleau, Pascal; Ziessel, Raymond

    2009-08-17

    We have designed and synthesised a series of modular, mesogenic complexes based on anthracene-2,6-disulfonate and trialkoxybenzyl-functionalised imidazolium cations. Each complex contains a central, rigid, dianionic anthracene core and two flexible monocations bearing paraffin chains anchored on imidazolium rings. Anthracene-2,6-disulfonate can be crystallised with various simple alkylammonium ions and, in the case of +N(CH3)2(C16H33)2, a crystal structure determination has shown that the long paraffinic chains are intercalated between the anthracene moieties. The dianion forms columnar mesophases with trialkoxybenzylimidazolium cations, as identified by polarising optical microscopy and X-ray scattering measurements. Differential scanning calorimetry studies confirmed mesomorphic behaviour from room temperature to about 200 degrees C for alkyl chains containing 8, 12 and 16 carbon atoms. The strong luminescence of anthracene is maintained in the mesophase and fluorescence measurements confirmed the presence of J aggregates in all cases. The new functional materials described herein provide an easy access to stable and luminescent mesomorphic materials engineered by an ionic self-assembly process.

  7. Biostimulation Reveals Functional Redundancy of Anthracene-Degrading Bacteria in Polycyclic Aromatic Hydrocarbon-Contaminated Soil

    PubMed Central

    Dunlevy, Sage R.; Singleton, David R.; Aitken, Michael D.

    2013-01-01

    Abstract Stable-isotope probing was previously used to identify bacterial anthracene-degraders in untreated soil from a former manufactured gas plant site. However, subsequent pyrosequence analyses of total bacterial communities and quantification of 16S rRNA genes indicated that relative abundances of the predominant anthracene-degrading bacteria (designated Anthracene Group 1) diminished as a result of biological treatment conditions in lab-scale, aerobic bioreactors. This study identified Alphaproteobacterial anthracene-degrading bacteria in bioreactor-treated soil which were dissimilar to those previously identified. The largest group of sequences was from the Alterythrobacter genus while other groups of sequences were associated with bacteria within the order Rhizobiales and the genus Bradyrhizobium. Conditions in the bioreactor enriched for organisms capable of degrading anthracene which were not the same as those identified as dominant degraders in the untreated soil. Further, these data suggest that identification of polycyclic aromatic hydrocarbon-degrading bacteria in contaminated but untreated soil may be a poor indicator of the most active degraders during biological treatment. PMID:24302851

  8. Anthracene-organosiloxane spin-on antireflective coating for KrF lithography

    NASA Astrophysics Data System (ADS)

    Kennedy, Joseph T.; Baldwin-Hendricks, Teri; Hebert, Mello; Suedmeyer, Arlene

    2003-06-01

    A sacrificial, spin-on 248nm UV absorbing organosiloxane film has been developed to enable via first trench last (VFTL) dual-damascene patterning. Amongst other design objectives one key material requirement was that the film be SiO based to facilitate trench etch. Because our starting organosiloxane polymer is transparent a chromophores that absorbs at 248 nm had to be included. Anthracene was selected as it offered the largest amount of absorption per mole. Unfortunately, commercially available anthracene moieties with different functional groups when added directly to the organosiloxane polymer solution resulted in films of very marginal quality. The primary issue was the poor solubility and thermal stability of the anthracene compound within the organosiloxane matrix. To address this fundamental problem the chromophore was stabilized by chemically attaching it to ethyl-orthosilicate. The resulting molecule, 9-anthracene carboxy-methyl triethoxysilane (TESAC) was developed. By combining the appropriate amounts of TESAC, TEOS and other organo-TEOS monomers with the appropriate solvents and a catalyst a stable, 248nm light absorbing anthracene-organosiloxane polymer was developed. This work has led to the development of Duo248 organosiloxane based bottom antireflective coatings. Topics such as the development of TESAC, lithography, plasma etch and selective removal will be discussed.

  9. Homoleptic 2,2'-bipyridine metalates(-I) of iron and cobalt, one cocrystallized with an anthracene radical anion and the other with neutral anthracene.

    PubMed

    Brennessel, William W; Ellis, John E

    2014-08-01

    Homoleptic 2,2'-bipyridine (bipy) metalates of iron and cobalt have been synthesized directly from the corresponding homoleptic anthracene metalates. In the iron structure, bis[([2.2.2]cryptand)potassium(I)] tris(2,2'-bipyridine)ferrate(-I) anthracene(-I), [K(C18H36N2O6)]2[Fe(C10H8N2)3](C14H10), the asymmetric unit contains one potassium complex cation in a general position, the Fe center and one and a half bipy ligands of the ferrate complex on a crystallographic twofold axis that includes the Fe atom, and one half of an anthracene radical anion whose other half is generated by a crystallographic inversion center. The cations and anions are well separated and the geometry about the Fe center is essentially octahedral. In the cobalt structure, ([2.2.2]cryptand)potassium(I) bis(2,2'-bipyridine)cobaltate(-I) anthracene hemisolvate tetrahydrofuran (THF) disolvate, [K(C18H36N2O6)][Co(C10H8N2)2]·0.5C14H10·2C4H8O, the asymmetric unit contains the cation, anion, and both cocrystallized THF solvent molecules in general positions, and one half of a cocrystallized anthracene molecule whose other half is generated by a crystallographic inversion center. The cation and anion are well separated and the ligand planes in the cobaltate anion are periplanar. Each anthracene molecule is midway between and is oriented perpendicular to a pair of symmetry-related bipy ligands such that aromatic donor-acceptor interactions may play a role in the packing arrangement. The lengths of the bonds that connect the bipy rings support the assertion that the ligands are bipy radical anions in the iron structure. However, in the case of cobalt, these lengths are between the known ranges for a bipy radical anion and a bipy dianion, and therefore no conclusion can be made from the crystallography alone. One cocrystallized THF solvent molecule in the cobalt structure was modeled as disordered over three positions with appropriate geometric and thermal restraints, which resulted in a refined

  10. Multi-Electron Oxidation of Anthracene Derivatives by Nonheme Manganese(IV)-Oxo Complexes.

    PubMed

    Sharma, Namita; Jung, Jieun; Lee, Yong-Min; Seo, Mi Sook; Nam, Wonwoo; Fukuzumi, Shunichi

    2017-03-27

    Six-electron oxidation of anthracene to anthraquinone by a nonheme Mn(IV)-oxo complex, [(Bn-TPEN)MnIV(O)]2+, proceeds via the rate-determining electron transfer from anthracene to [(Bn-TPEN)MnIV(O)]2+, followed by subsequent fast oxidation reactions to give anthraquinone. The reduced Mn(II) complex ([(Bn-TPEN)MnII]2+) is oxidized by [(Bn-TPEN)MnIV(O)]2+ rapidly to produce the μ-oxo dimer ([(Bn-TPEN)MnIII-O-MnIII(Bn-TPEN)]4+). The oxygen atoms of the anthraquinone product were found to derive from the manganese-oxo species by the 18O labelling experiments. In the presence of Sc3+ ion, formation of anthracene radical cation was directly detected in electron transfer from anthracene to a Sc3+ ion-bound MnIV(O) com-plex, [(Bn-TPEN)MnIV(O)-(Sc(OTf)3)2]2+, followed by subsequent further oxidation to yield anthraquinone. When anthracene was replaced by 9,10-dimethylanthracene, elec-tron transfer from 9,10-dimethylanthracene to [(Bn-TPEN)MnIV(O)-(Sc(OTf)3)2]2+ occurred rapidly to produce stable 9,10-dimethylanthracene radical cation. The driving force dependence of the rate constants of electron transfer from anthracene derivatives to [(Bn-TPEN)MnIV(O)]2+ and [(Bn-TPEN)MnIV(O)-(Sc(OTf)3)2]2+ was well evaluated in light of the Marcus theory of electron transfer.

  11. Construction of energy transfer pathways self-assembled from DNA-templated stacks of anthracene.

    PubMed

    Iwaura, Rika; Yui, Hiroharu; Someya, Yuu; Ohnishi-Kameyama, Mayumi

    2014-01-05

    We describe optical properties of anthracene stacks formed from single-component self-assembly of thymidylic acid-appended anthracene 2,6-bis[5-(3'-thymidylic acid)pentyloxy] anthracene (TACT) and the binary self-assembly of TACT and complementary 20-meric oligoadenylic acid (TACT/dA20) in an aqueous buffer. UV-Vis and emission spectra for the single-component self-assembly of TACT and the binary self-assembly of TACT/dA20 were very consistent with stacked acene moieties in both self-assemblies. Interestingly, time-resolved fluorescence spectra from anthracene stacks exhibited very different features of the single-component and binary self-assemblies. In the single-component self-assembly of TACT, a dynamic Stokes shift (DSS) and relatively short fluorescence lifetime (τ=0.35ns) observed at around 450nm suggested that the anthracene moieties were flexible. Moreover, a broad emission at 530nm suggested the formation of an excited dimer (excimer). In the binary self-assembly of TACT/dA20, we detected a broad, red-shifted emission component at 534nm with a lifetime (τ=0.4ns) shorter than that observed in the TACT single-component self-assembly. Combining these results with the emission spectrum of the binary self-assembly of TACT/5'-HEX dA20, we concluded that the energy transfer pathway was constructed by columnar anthracene stacks formed from the DNA-templated self-assembly of TACT.

  12. Formation of bound residues during microbial degradation of [{sup 14}C]anthracene in soil

    SciTech Connect

    Kaestner, M.; Streibich, S.; Beyrer, M.; Fritsche, W.; Richnow, H.H.

    1999-05-01

    Carbon partitioning and residue formation during microbial degradation of polycyclic aromatic hydrocarbons (PAH) in soil and soil-compost mixtures were examined by using [{sup 14}C]anthracenes labeled at different positions. In native soil 43.8% of [9-{sup 14}C]anthracene was mineralized by the autochthonous microflora and 45.4% was transformed into bound residues within 176 days. Addition of compost increased the metabolism and decreased the residue formation (20.7% of the anthracene was transformed). Thus, the higher organic carbon content after compost was added did not increase the level of residue formation. [{sup 14}C]anthracene labeled at position 1,2,3,4,4a,5a was metabolized more rapidly and resulted in formation of higher levels of residues (28.5%) by the soil-compost mixture than [{sup 14}C]anthracene radiolabeled at position C-9 (20.7%). Two phases of residue formation were observed in the experiments. In the first phase the original compound was sequestered in the soil, as indicated by its limited extractability. In the second phase metabolites were incorporated into humic substances after microbial degradation of the PAH (biogenic residue formation). PAH metabolites undergo oxidative coupling to phenolic compounds to form nonhydrolyzable humic substance-like macromolecules. The authors found indications that monomeric educts are coupled by C-C- or either bonds. Hydrolyzable ester bonds or sorption of the parent compounds plays a minor role in residue formation. Moreover, experiments performed with {sup 14}CO{sub 2} revealed that residues may arise from CO{sub 2} in the soil in amounts typical for anthracene biodegradation. The extent of residue formation depends on the metabolic capacity of the soil microflora and the characteristics of the soil. The position of the {sup 14}C label is another important factor which controls mineralization and residue formation from metabolized compounds.

  13. Interaction of atomic hydrogen with anthracene and polyacene from density functional theory

    NASA Astrophysics Data System (ADS)

    Ferullo, Ricardo M.; Castellani, Norberto J.; Belelli, Patricia G.

    2016-03-01

    The interaction of atomic hydrogen with two linear polycyclic aromatic hydrocarbons (PAHs), anthracene and polyacene (the polymer of benzene), was studied within the density functional theory (DFT). Using a proper dispersion-corrected method (DFT-D) the preferential physisorption sites were explored. The activation barrier for the bond formation between a peripheral C and the incoming H was calculated to be 58.5 and 34.1 meV with pure DFT on anthracene and polyacene at its antiferromagnetic ground state, respectively. DFT-D, although improves the description of the physisorbed state, tends to underestimate the chemisorption barriers due an artifact arising from the dispersion correction.

  14. Changes in the Bacterial Community Structure of Remediated Anthracene-Contaminated Soils.

    PubMed

    Delgado-Balbuena, Laura; Bello-López, Juan M; Navarro-Noya, Yendi E; Rodríguez-Valentín, Analine; Luna-Guido, Marco L; Dendooven, Luc

    2016-01-01

    Mixing soil or adding earthworms (Eisenia fetida (Savigny, 1826)) accelerated the removal of anthracene, a polycyclic aromatic hydrocarbon, from a pasture and an arable soil, while a non-ionic surfactant (Surfynol® 485) inhibited the removal of the contaminant compared to the untreated soil. It was unclear if the treatments affected the soil bacterial community and consequently the removal of anthracene. Therefore, the bacterial community structure was monitored by means of 454 pyrosequencing of the 16S rRNA gene in the pasture and arable soil mixed weekly, amended with Surfynol® 485, E. fetida or organic material that served as food for the earthworms for 56 days. In both soils, the removal of anthracene was in the order: mixing soil weekly (100%) > earthworms applied (92%) > organic material applied (77%) > untreated soil (57%) > surfactant applied (34%) after 56 days. There was no clear link between removal of anthracene from soil and changes in the bacterial community structure. On the one hand, application of earthworms removed most of the contaminant from the arable soil and had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of the Acidobacteria, Chloroflexi and Gemmatimonadetes, and an increase in that of the Proteobacteria compared to the unamended soil. Mixing the soil weekly removed all anthracene from the arable soil, but had little or no effect on the bacterial community structure. On the other hand, application of the surfactant inhibited the removal of anthracene from the arable soil compared to the untreated soil, but had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of Cytophagia (Bacteroidetes), Chloroflexi, Gemmatimonadetes and Planctomycetes and an increase in that of the Flavobacteria (Bacteroidetes) and Proteobacteria. Additionally, the removal of anthracene was similar in the different treatments of both the arable and pasture soil, but the

  15. Synthesis, crystal structures and photoluminescence of anthracen- and pyrene-based coumarin derivatives.

    PubMed

    Zhang, Hui; Tong, Hao; Zhao, Yuling; Yu, Tianzhi; Zhang, Peng; Li, Jianfeng; Fan, Duowang

    2015-11-05

    Two new anthracen- and pyrene-based coumarin derivatives, 3-(4-(anthracen-10-yl)phenyl)coumarin (4) and 3-(4-(pyrene-1-yl)phenyl)coumarin (5), were synthesized and characterized by FT-IR, (1)H NMR, element analysis and single crystal X-ray crystallography. The UV-vis absorption and photoluminescence spectra of these coumarin derivatives were investigated. The results show that compound 4 and 5 exhibit blue and blue-green emissions, respectively, under ultraviolet light excitation. Compared with the compound 4, the emission peak of compound 5 was bathochromically shifted by about 80 nm due to the more planar structure and larger π-conjugation.

  16. Changes in the Bacterial Community Structure of Remediated Anthracene-Contaminated Soils

    PubMed Central

    Delgado-Balbuena, Laura; Bello-López, Juan M.; Navarro-Noya, Yendi E.; Rodríguez-Valentín, Analine; Luna-Guido, Marco L.; Dendooven, Luc

    2016-01-01

    Mixing soil or adding earthworms (Eisenia fetida (Savigny, 1826)) accelerated the removal of anthracene, a polycyclic aromatic hydrocarbon, from a pasture and an arable soil, while a non-ionic surfactant (Surfynol® 485) inhibited the removal of the contaminant compared to the untreated soil. It was unclear if the treatments affected the soil bacterial community and consequently the removal of anthracene. Therefore, the bacterial community structure was monitored by means of 454 pyrosequencing of the 16S rRNA gene in the pasture and arable soil mixed weekly, amended with Surfynol® 485, E. fetida or organic material that served as food for the earthworms for 56 days. In both soils, the removal of anthracene was in the order: mixing soil weekly (100%) > earthworms applied (92%) > organic material applied (77%) > untreated soil (57%) > surfactant applied (34%) after 56 days. There was no clear link between removal of anthracene from soil and changes in the bacterial community structure. On the one hand, application of earthworms removed most of the contaminant from the arable soil and had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of the Acidobacteria, Chloroflexi and Gemmatimonadetes, and an increase in that of the Proteobacteria compared to the unamended soil. Mixing the soil weekly removed all anthracene from the arable soil, but had little or no effect on the bacterial community structure. On the other hand, application of the surfactant inhibited the removal of anthracene from the arable soil compared to the untreated soil, but had a strong effect on the bacterial community structure, i.e. a decrease in the relative abundance of Cytophagia (Bacteroidetes), Chloroflexi, Gemmatimonadetes and Planctomycetes and an increase in that of the Flavobacteria (Bacteroidetes) and Proteobacteria. Additionally, the removal of anthracene was similar in the different treatments of both the arable and pasture soil, but the

  17. Growth of optical-quality anthracene crystals doped with dibenzoterrylene for controlled single photon production

    SciTech Connect

    Major, Kyle D. Lien, Yu-Hung; Polisseni, Claudio; Grandi, Samuele; Kho, Kiang Wei; Clark, Alex S.; Hwang, J.; Hinds, E. A.

    2015-08-15

    Dibenzoterrylene (DBT) molecules within a crystalline anthracene matrix show promise as quantum emitters for controlled, single photon production. We present the design and construction of a chamber in which we reproducibly grow doped anthracene crystals of optical quality that are several mm across and a few μm thick. We demonstrate control of the DBT concentration over the range 6–300 parts per trillion and show that these DBT molecules are stable single-photon emitters. We interpret our data with a simple model that provides some information on the vapour pressure of DBT.

  18. Dibenz[a,c]anthracene: a potent inhibitor of skin-tumor initiation by 7,12-dimethylbenz[a]anthracene.

    PubMed

    Slaga, T J; Viaje, A; Buty, S G; Bracken, W M

    1978-03-01

    The mechanism by which the weak tumor initiator dibenz[a,c]anthracene (DB[a,c]A) inhibits the skin-tumor-initiating activity of 7,12-dimethylbenz[a]anthracene (DMBA) was investigated. DB[a,c]A was found to be a potent inhibitor of DMBA initiation when given either 5 min, or 1, 12, or 36 hours before DMBA. Pretreatment of mice with unlabeled DB[a,c]A at either 1, 12, or 36 hours before killing increased the in vitro epidermally mediated covalent binding of [3H]DMBA to DNA more than pretreatment with unlabeled DMBA at comparable times. Only when the tumor experiments were mimicked did a decrease in DMBA covalent binding to DNA in vitro occur. The results suggests that some competition at the level of polycyclic hydrocarbon metabolism or at the genome level may exist between metabolites of the weak carcinogen and those of the strong carcinogen.

  19. Comparison of mutagenesis and malignant transformation by dihydrodiols from benz[a]anthracene and 7,12-dimethylbenz[a]anthracene.

    PubMed Central

    Marquardt, H.; Baker, S.; Tierney, B.; Grover, P. L.; Sims, P.

    1979-01-01

    Five dihydrodiols derived from benz[a]anthracene (BA) and 4 dihydrodiols derived from 7,12-dimethylbenz[a]anthracene (DMBA) have been tested, together with the parent hydrocarbons, for their abilities to induce mutations to 8-azaguanine resistance in V79 (Chinese hamster cells and malignant transformation in M2 mouse fibroblasts. The syn- and anti-isomers of benz[a]anthracene 8,9-diol 10,11-oxide were also tested for biological activity in these two systems. The non-K-region 1,2- and 3,4-dihydrodiols of BA induced mutations but the non-K-region 8,9-dihydrodiol and the K-region 5,6-dihydrodiol were inactive as mutagens; none of these BA diols transformed M2 mouse fibroblasts. The 3,4- and the 8,9-dihydrodiols derived from 7,12-dimethylbenz[a]anthracene induced mutations in V79 cells and malignant transformation in M2 mouse fibroblasts and both were more active than the hydrocarbon itself. The K-region 5,6-dihydrodiol and the non-K-region 10,11-dihydrodiol of DMBA were inactive in both test systems. The results are not inconsistent with other data suggesting that the metabolic activation of both BA and DMBA occurs through conversion of the respective 3,4-dihydrodiols into the related vicinal diol-epoxides, although other dihydrodiols may also be involved in vivo. Both the BA diol-epoxides tested were mutagenic, but although the anti-isomer transformed M2 fibroblasts, the syn-isomer was inactive. PMID:114201

  20. Coherent electronic energy transfer and nonlinear polariton effects in anthracene-doped naphthalene crystals

    SciTech Connect

    Connolly, M.A.

    1987-01-01

    The nature of electronic energy transfer in strain-free mounted anthracene-doped naphthalene single crystals at frequencies near that of the (0.0) a-exciton in naphthalene was probed using sensitized resonant two-photon fluorescence excitation (TPE) and second harmonic generation (SHG) spectroscopies. The naphthalene-to-anthracene TPE intensity ratios were found to be 1.2 and 1.6, for excitation of the zero-phonon transition at 1.6 K and 20 K, respectively. This result is consistent with coherent exciton-polariton electronic energy transfer at liquid helium temperatures, and incoherent transfer at high temperatures. Energy transfer for the pure and the anthracene-doped naphthalene systems under investigation was determined to be in the capture limited regime. The polariton trapping event is discussed in terms of scattering off a trap with subsequent trapping (i.e., capture) and scattering off a trap without subsequent trapping (i.e., trap scattering). Thermal broadening and temperature dependences of the TPE and SHG signal intensities for both naphthalene and anthracene are presented and are discussed in terms of the polariton fusion model. The experimental data do not agree with the theoretical predictions; this discrepancy is discussed in terms of the anomalous crystal habit (diamond plates) observed in the present investigation. The first report of a longitudinal exciton in a doped organic molecular system also is reported.

  1. [Isolation, charcaterization of an anthracene degrading bacterium Martelella sp. AD-3 and cloning of dioxygenase gene].

    PubMed

    Cui, Chang-Zheng; Feng, Tian-Cai; Yu, Ya-Qi; Dong, Fei; Yang, Xin-Mei; Feng, Yao-Yu; Liu, Yong-Di; Lin, Han-Ping

    2012-11-01

    Anthracene, among the 16 US EPA polycyclic aromatic hydrocarbons (PAHs), is a typical low molecular weight environmental contaminant, which gains concern on its biodegradation under hypersaline condition. In this study, an anthracene-degrading bacterial strain was isolated from highly saline petroleum-contaminated soil. Based on its physiological, biochemical characteristics and 16S rDNA sequence analysis, the bacteria was preliminary identified and named as Martelella sp. AD-3. The strain was able to utilize anthracene as sole carbon source for growth and the degradation occurred under broad salinities (0.1% to 10%) and varying pHs (6.0 to 10.0). The optimized degradation conditions were initial concentration 25 mg x L(-1), culture temperature 30 degrees C, pH 9.0 and salinity 3%. And 94.6% of anthracene was degraded by strain AD-3 under the optimal conditions within 6 days. Degenerate primers design was performed with a reported dioxygenase alpha subunit homologous gene. A length of 307 bp fragment of the partial dioxygenase gene sequences (GenBank accession: JF823991.1) was amplified by nested PCR. The clones amino acid sequence from strain AD-3 showed 95% identity to that of the partial naphthalene dioxygenase large-subunit from Marinobacter sp. NCE312 (AF295033). The results lay a foundation for the further study of molecular mechanism involved in the PAHs biodegradation by strain AD-3.

  2. Fate of carbamazepine and anthracene in soils watered with UV-LED treated wastewaters.

    PubMed

    Chevremont, A-C; Boudenne, J-L; Coulomb, B; Farnet, A-M

    2013-11-01

    Water disinfection technologies based on ultraviolet (UV) radiations emitted by Light-Emitting Diodes (LED), as a wastewater tertiary treatment, have been shown to be promising for water reuse. Here, we assessed the fate of two ubiquitous pollutants, carbamazepine and anthracene, in soil watered with either UV-LED treated wastewaters or irrigation water. After 3 months, anthracene and carbamazepine were transformed two and three times faster respectively, in soils watered with UV-LED wastewater than in soils watered with tap water (probably because of the addition of organic matter by the effluent). Laccase activity was induced in the presence of the pollutants and anthraquinone was found as anthracene product of oxidation by laccases. Moreover, the addition of these pollutants into soil did not affect the functional diversity of autochthonous microbial communities assessed by Ecolog plates. Cellulase, protease and urease activities increased in soils watered with UV-LED treated wastewaters (UV-LED WW), showing transformation of organic matter from the effluent and lipase activity increased by anthracene addition, confirming the potential role of these enzymes as indicators of hydrocarbon contamination.

  3. Two-photon excitation into low-energy singlet states of anthracene in mixed crystals

    NASA Astrophysics Data System (ADS)

    Bree, A.; Leyderman, A.; Taliani, C.

    1985-08-01

    The two-photon excitation spectrum of the first excited state of anthracene in fluorene and biphenyl at 4.2 K has been measured. Intensity is induced into the origin by the static dipole moment of fluorene, and into b 1u vibrons through coupling to an A g state near 29400 cm -1; the nature of this A g state is discussed.

  4. Assessment of anthracene toxicity toward environmental eukaryotic microorganisms: Tetrahymena pyriformis and selected micromycetes.

    PubMed

    Bonnet, J L; Guiraud, P; Dusser, M; Kadri, M; Laffosse, J; Steiman, R; Bohatier, J

    2005-01-01

    The toxicity of anthracene, a nonmutagenic, noncarcinogenic, low-molecular-weight polycyclic aromatic hydrocarbon present in the environment, was assessed using a ciliated protozoan, Tetrahymena pyriformis, and a selection of 10 micromycetes from different taxonomic groups living in two environmental compartments, namely aquatic and soil ecosystems. With T. pyriformis, a concentration-dependent inhibitory effect was shown on the cell proliferation rate, IC(50) = 33.40+/-4.84 mg/L (kinetic method). Phagocytosis of nonsoluble anthracene was confirmed by the presence of digestive vacuoles with photon microscopy. In fungi, anthracene did not exhibit a fungicide effect but showed a fungistatic action. Except for Absidia fusca and Cladosporium herbarum, the micromycetes showed a concentration-dependent decrease in growth. From IC(50) values determined by endpoint or kinetic methods, Rhodotorula glutinis and all of the Ascomycotina (except for Penicillium chrysogenum) were the most sensitive species, while Phanerochaete chrysosporium, P. chrysogenum, and the two Deuteromycotina were more resistant to anthracene. Our discussion focuses on the evaluation of toxicity by the two methods used for the calculation of the IC(50) values (endpoint and kinetic), the advantages of studying growth by a kinetic method (the dynamic aspect), and a comparison of toxicity to T. pyriformis and the different micromycetes.

  5. Efficient light harvesters based on the 10-(1,3-dithiol-2-ylidene)anthracene core.

    PubMed

    Bouit, Pierre-Antoine; Infantes, Lourdes; Calbo, Joaquín; Viruela, Rafael; Ortí, Enrique; Delgado, Juan Luis; Martín, Nazario

    2013-08-16

    Three new push-pull chromophores based on the 10-(1,3-dithiol-2-ylidene)anthracene core were synthesized and fully characterized. The new chromophores display broad absorption spectra, nearly covering the whole visible region, with high extinction coefficients. Electrochemistry and theoretical calculations allowed the understanding of these singular electronic properties. The molecular structures were unambiguously confirmed by X-ray diffraction.

  6. Synthesis and electroluminescent properties of anthracene derivatives containing electron-withdrawing oxide moieties

    SciTech Connect

    Yoon, Jhin-yeong; Na, Eun Jae; Park, Soo Na; Lee, Seok Jae; Kim, Young Kwan; Yoon, Seung Soo

    2014-10-15

    Highlights: • Blue fluorescent material is important for application in full-color displays. • We have synthesized emitters based on anthracene connected with oxide moieties. • 1C shows a highly efficient blue EL emission due to electron-injection property. - Abstract: A series of new blue-emitting materials: (4-(10-(naphthalen-2-yl)anthracen-9-yl)phenyl)(phenyl)methanone (1); 9-(naphthalen-2-yl)-10-(4-((diphenyl)phosphine oxide)phenyl)anthracene (2); 9-(naphthalen-2-yl)-10-(4-(phenylsulfonyl)phenyl)anthracene (3) were designed and synthesized via Suzuki cross-coupling reaction. Multilayer OLEDs were fabricated in the following sequence: ITO (180 nm)/NPB (50 nm)/blue materials 1–3 (30 nm)/TPBi (15 nm)/Liq (2 nm)/Al (100 nm). All devices showed the efficient blue EL emissions. In particular, the device using 1 as an emitter exhibited efficient blue electroluminescent properties with a maximum luminous, power, external quantum efficiency and CIE coordinates of 0.36 cd/A, 0.90 lm/W, 0.55% at 20 mA/cm{sup 2} and (x = 0.16, y = 0.20) at 10.0 V, respectively.

  7. Electron attachment to anthracene. A FALP measurement of the rate coefficient at room temperature

    NASA Astrophysics Data System (ADS)

    Canosa, A.; Parent, D. C.; Pasquerault, D.; Au; Gomet, J. C.; Laubé, S.; Rowe, B. R.

    1994-09-01

    The rate coefficient β for electron attachment to anthracene has been measured at room temperature using a flowing afterglow Langmuir probe mass spectrometer. A value of 1 × 10 -9 cm 3 s -1 (30% uncertainty) was found, indicating that an activation energy barrier might exist.

  8. Enhancement of fluorescence in anthracene by chlorination: Vibronic coupling and transition dipole moment density analysis

    NASA Astrophysics Data System (ADS)

    Uejima, Motoyuki; Sato, Tohru; Tanaka, Kazuyoshi; Kaji, Hironori

    2014-02-01

    The vibronic coupling constants and transition dipole moments for the Franck-Condon and adiabatic S1 states of anthracene, 9-chloroanthracene, and 9,10-dichloroanthracene were calculated and analyzed by using the concept of vibronic coupling density (VCD). The transition dipole moments are also analyzed on the basis of the transition dipole moment density (TDMD). The VCD analyses indicate that the vibronic couplings in the Franck-Condon S1 state come from the side rings of anthracene, and introduction of chlorine atoms reduces the vibronic couplings in the side regions and the reorganization energy. The TDMD analyses indicate that the chlorination enhances the transition dipole moment and that the contribution of the chlorine atom to the transition dipole moment is the largest. Finally, we derived a design principle for anthracene derivatives with a high quantum yield: the same long acceptors should be introduced into the two central carbon atoms in the anthracene's central ring for the derivative to keep the point group to be D2h.

  9. Selective Two-Photon-Absorption-Induced Reactions of Anthracene-2-Carboxylic Acid on Tunable Plasmonic Substrate with Incoherent Light Source.

    PubMed

    Pincella, Francesca; Isozaki, Katsuhiro; Taguchi, Tomoya; Song, Yeji; Miki, Kazushi

    2015-02-01

    In this research, we report the development, characterization and application of various plasmonic substrates (with localized surface plasmon resonance wavelength tunable by gold nanoparticle size) for two-photon absorption (TPA)-induced photodimerization of an anthracene derivative, anthracene carboxylic acid, in both surface and solution phase under incoherent visible light irradiation. Despite the efficient photoreaction property of anthracene derivatives and the huge number of publications about them, there has never been a report of a multiphoton photoreaction involving an anthracene derivative with the exception of a reverse photoconversion of anthracene photodimer to monomer with three-photon absorption. We examined the progress of the TPA-induced photoreaction by means of surface-enhanced Raman scattering, taking advantage of the ability of our plasmonic substrate to enhance and localize both incident light for photoreaction and Raman scattering signal for analysis of photoreaction products. The TPA-induced photoreaction in the case of anthracene carboxylic acid coated 2D array of gold nanoparticles gave different results according to the properties of the plasmonic substrate, such as the size of the gold nanoparticle and also its resultant optical properties. In particular, a stringent requirement to achieve TPA-induced photodimerization was found to be the matching between irradiation wavelength, localized surface plasmon resonance of the 2D array, and twice the wavelength of the molecular excitation of the target material (in this case, anthracene carboxylic acid). These results will be useful for the future development of efficient plasmonic substrates for TPA-induced photoreactions with various materials.

  10. Bioremediation of anthracene contaminated soil in bio-slurry phase reactor operated in periodic discontinuous batch mode.

    PubMed

    Prasanna, D; Venkata Mohan, S; Purushotham Reddy, B; Sarma, P N

    2008-05-01

    Bioremediation of soil-bound anthracene was studied in a series of bio-slurry phase reactors operated in periodic discontinuous/sequencing batch mode under anoxic-aerobic-anoxic microenvironment using native soil microflora. Five reactors were operated for a total cycle period of 144 h (6 days) at soil loading rate of 16.66 kg soil/m(3)/day at 30 +/- 2 degrees C temperature. The performance of the bioreactors was studied at various substrate loading rates (volumetric substrate loading rate (SLR), 0.1, 0.2 and 0.3g anthracene/kg soil/day) with and without bioaugmentation (domestic sewage inoculum; 2 x 10(6) CFU/g of soil). Control reactor (without microflora) showed negligible degradation of anthracene due to the absence of biological activity. The performance of the bio-slurry system with respect to anthracene degradation was found to depend on both substrate loading rate and bioaugmentation. Application of bioaugmentation showed positive influence on the rate of degradation of anthracene. Anthracene degradation data was analysed using different kinetic models to understand the mechanism of bioremediation process in the bio-slurry phase system. Variation in pH/oxidation-reduction potential (ORP), soil microflora and oxygen consumption rate correlated well with the substrate degradation pattern observed during soil slurry phase anthracene degradation.

  11. Flocculant in wastewater affects dynamics of inorganic N and accelerates removal of phenanthrene and anthracene in soil.

    PubMed

    Fernandez-Luqueno, F; Thalasso, F; Luna-Guido, M L; Ceballos-Ramírez, J M; Ordoñez-Ruiz, I M; Dendooven, L

    2009-06-01

    Recycling of municipal wastewater requires treatment with flocculants, such as polyacrylamide. It is unknown how polyacrylamide in sludge affects removal of polycyclic aromatic hydrocarbons (PAH) from soil. An alkaline-saline soil and an agricultural soil were contaminated with phenanthrene and anthracene. Sludge with or without polyacrylamide was added while emission of CO(2) and concentrations of NH(4)(+), NO(3)(-), NO(2)(-), phenanthrene and anthracene were monitored in an aerobic incubation experiment. Polyacrylamide in the sludge had no effect on the production of CO(2), but it reduced the concentration of NH(4)(+), increased the concentration of NO(3)(-) in the Acolman soil and NO(2)(-) in the Texcoco soil, and increased N mineralization compared to the soil amended with sludge without polyacrylamide. After 112d, polyacrylamide accelerated the removal of anthracene from both soils and that of phenanthrene in the Acolman soil. It was found that polyacrylamide accelerated removal of phenanthrene and anthracene from soil.

  12. Tethered anthracene pair as molecular tweezers for post-production separation of single-walled carbon nanotubes

    NASA Astrophysics Data System (ADS)

    Anderson, Ankoma; Yang, Fengchun; Cao, Li; Li, Huaping; Meziani, Mohammed J.; Sun, Ya-Ping

    2016-07-01

    As-produced single-walled carbon nanotubes (SWNTs) are metallic and semiconducting mixtures. An anthracene mono-derivative with a long alkyl tail and a molecule with a tethered pair of anthracene species (bis-anthracene) in a ;molecular tweezers;-like configuration were synthesized and evaluated for the separation of SWNTs. While the mono-derivative was incapable of the noncovalent functionalization-solubilization, the bis-anthracene was found to be very effective. The results suggest that molecular tweezers of a tethered pair of planar aromatic species can be coupled with the selection of a suitable solvent or solvent mixture for effective and efficient post-production separation of metallic and semiconducting SWNTs.

  13. Quinoline-Substituted 10-(naphthalene-7-yl)anthracene Derivatives for Blue Fluorescent Organic Light-Emitting Diodes.

    PubMed

    Kim, Chanwoo; Park, Soo Na; Lee, Seul Bee; Kim, Young Seok; Lee, Ho Won; Kim, Young Kwan; Yoon, Seung Soo

    2016-02-01

    In this study, we have designed and synthesized blue emitters based on quinoline-substituted 10-(naphthalene-7-yl)anthracene. Particularly, a material exhibited highly efficient blue electroluminescence with CIE coordinates of (0.15, 0.18).

  14. Thermal-delayed fluorescence of pyromellitic dianhydride—anthracene trap in charge-transfer pyromellitic dianhyride—phenanthrene host crystal

    NASA Astrophysics Data System (ADS)

    Kozankiewicz, B.

    1990-10-01

    The fluorescence, phosphorescence and delayed fluorescence in an anthracene-doped pyromellitic dianhydride—phenanthrene crystal is studied within the temperature range 200-330 K. The dominating long-lived emission for temperatures above 250 K is thermal-delayed fluorescence, originating from the singlet trap created by thermal promotion of the triplet trap. The trap is formed on the pyromellitic dianhydride—anthracene complex unit. The activation energy of thermal promotions is ≈ 2500 cm -1.

  15. The use of anthracene as a model compound in a comparative study of hydrous pyrolysis methods for industrial waste remediation.

    PubMed

    Nkansah, Marian Asantewah; Christy, Alfred A; Barth, Tanja

    2011-07-01

    Polycyclic aromatic hydrocarbons are very stable compounds and tend to bioaccumulate in the environment due to their high degree of conjugation and aromaticity. Hydrous pyrolysis is explored as a technique for the treatment of industrial water containing PAH, using anthracene as a model compound. The reactivity of anthracene under a range of temperatures and durations are studied in this paper. Aliquots of 1.0-10.0mg of anthracene in a range of 1.0-5.0 mL of H(2)O are subjected to hydrous pyrolysis under varied conditions of temperature, reagents and duration. The conditions include oxidising systems comprising distilled water, hydrogen peroxide and Nafion-SiO(2) solid catalyst in water; and reducing systems of formic acid and formic acid/Nafion-SiO(2)/Pd-C catalysts to assess a range of redox reaction conditions. Oxygen in air played a role in some of the reaction conditions. Pyrolysed products were identified and quantified by the use of Gas Chromatography-Mass Spectrometry (GC-MS). The major products were anthrone, anthraquinone, xanthone from oxidation; and multiple hydro-anthracene derivatives from reductive hydogenation. The nature of reaction conditions influenced the extent of anthracene degradation. The products formed are more reactive (less stable) as compared to anthracene the starting material and will therefore be less persistent in the environment.

  16. Molecular dynamics of dibenz[a,h]anthracene and its metabolite interacting with lung surfactant phospholipid bilayers.

    PubMed

    Padilla-Chavarría, Helmut I; Guizado, Teobaldo R C; Pimentel, Andre S

    2015-08-28

    The interaction of dibenz[a,h]anthracene and its ultimate carcinogenic 3,4-diol-1,2-epoxide with lung surfactant phospholipid bilayers was successfully performed using molecular dynamics. The DPPC/DPPG/cholesterol bilayer (64 : 64 : 2) was used as the lung surfactant phospholipid bilayer model and compared with the DPPC bilayer as a reference. Dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide were inserted in water and lipid phases in order to investigate their interactions with the lung surfactant phospholipid bilayers. The radial distribution function between two P atoms in polar heads shows that the 3,4-diol-1,2-epoxide affects the order between the P atoms in the DPPC/DPPG/cholesterol model more than dibenz[a,h]anthracene, which is a consequence of its preference for the polar heads and dibenz[a,h]anthracene prefers to be located in the hydrocarbon chain of the phospholipid bilayers. Dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide may form aggregates in water and lipid phases, and in the water-lipid interface. The implications for the possible effect of dibenz[a,h]anthracene and its 3,4-diol-1,2-epoxide in the lung surfactant phospholipid bilayers are discussed.

  17. Synthesis and Luminescent Property of Poly(9-(3-vinyl-phenyl)-anthracene).

    PubMed

    Lee, Sunmi; Shin, Hwangyu; Park, Beom-Soo Michael; Lee, Jaehyun; Park, Jongwook

    2015-07-01

    Polymer light-emitting diodes (PLEDs) have attracted much attention from academia and industry field because of their various applications such as large area flat-panel displays and lightings. In this paper, we suggest new blue emitting polymer based on anthracene, Poly(9-(3-Vinyl-phenyl)-anthracene) (PVPA). From NMR data, vinyl group protons were disappeared and aromatic protons showed broad proton peaks because of polymer characteristics. PVPA had film property well and it exhibited vivid PL maximum values of 431, 455, 482 nm and broad PL spectrum. Three dopants for green, red, yellow were used to PVPA, all energy transfer was happened well. By using rubrene dopant of yellow emission, doped film provided white PL.

  18. Nonvolatile liquid anthracenes for facile full-colour luminescence tuning at single blue-light excitation

    PubMed Central

    Babu, Sukumaran Santhosh; Hollamby, Martin J.; Aimi, Junko; Ozawa, Hiroaki; Saeki, Akinori; Seki, Shu; Kobayashi, Kenji; Hagiwara, Keita; Yoshizawa, Michito; Möhwald, Helmuth; Nakanishi, Takashi

    2013-01-01

    Nonvolatile room-temperature luminescent molecular liquids are a new generation of organic soft materials. They possess high stability, versatile optical properties, solvent-free fluid behaviour and can effectively accommodate dopant dye molecules. Here we introduce an approach to optimize anthracene-based liquid materials, focussing on enhanced stability, fluorescence quantum yield, colour tunability and processability, with a view to flexible electronic applications. Enveloping the anthracene core in low-viscosity branched aliphatic chains results in stable, nonvolatile, emissive liquid materials. Up to 96% efficient energy-transfer-assisted tunable emission is achieved by doping a minute amount of acceptor dye in the solvent-free state. Furthermore, we use a thermoresponsive dopant to impart thermally controllable luminescence colours. The introduced strategy leading to diverse luminescence colours at a single blue-light excitation can be an innovative replacement for currently used luminescent materials, providing useful continuous emissive layers in developing foldable devices. PMID:23736114

  19. Semiempirical molecular orbital estimation of the relative stability of bianthryls produced by anthracene pyrolysis

    SciTech Connect

    Mulholland, J.A.; Mukherjee, J.; Wornat, M.J.; Sarofim, A.F.; Rutledge, G.C. . Dept. of Chemical Engineering)

    1993-08-01

    The pyrolysis of pure anthracene at temperatures between 1,200 and 1,500 K produced all six bianthryl isomers whose relative yields appear to be related to steric factors. To evaluate the hypothesis that thermodynamic factors govern the product distribution of bianthryls in this system, the relative enthalpies and entropies of biaryl isomers were estimated by molecular orbital modeling, using the semiempirical AM1 (Austin Model 1). Computational analysis of several isomer sets demonstrates that the relative stabilities of a large number of biaryl isomers are determined largely by steric interactions caused by structural features defined as bays, coves, and fjords. These steric factors affect both the degree of biaryl twist in the preferred conformation and the freedom of internal rotation. Molecular orbital modeling supports the hypothesis that a thermodynamic distribution of bianthryl isomers is produced by anthracene pyrolysis.

  20. Inhibiting the photosensitized oxidation of anthracene and tryptophan by means of natural antioxidants

    NASA Astrophysics Data System (ADS)

    Aksenova, N. A.; Vyzhlova, E. N.; Malinovskaya, V. V.; Parfenov, V. V.; Solov'eva, A. B.; Timashev, P. S.

    2013-08-01

    It is shown that model reactions of photosensitized oxidation of anthracene and tryptophan can be used for evaluation and comparison of antioxidant activity of various classes of compounds. Inhibition of the oxidation of substrates in the presence of the familiar antioxidants tocopherol (vitamin E), ascorbic acid (vitamin C), and mixtures of these vitamins with methionine, and in the presence of reputed antioxidants dihydroquercetin and taurine, are considered. It is concluded that all of the above compounds except for taurine have antioxidant properties; i.e., they reduce the rate constants of the photosensitized oxidation of anthracene and tryptophan. It is found that the inhibition of oxidation is associated with the interaction between antioxidants and singlet oxygen. Analysis of the kinetic dependences of the photosensitized oxidation of substrates in the presence of antioxidants reveals that a mixture of vitamins inhibits the process most efficiently, and inhibition occurs at the initial stages due to more active interaction between singlet oxygen and vitamin C

  1. A molecular dynamics study on slow ion interactions with the polycyclic aromatic hydrocarbon molecule anthracene

    SciTech Connect

    Postma, J.; Hoekstra, R.; Schlathölter, T.; Tielens, A. G. G. M.

    2014-03-01

    Atomic collisions with polycyclic aromatic hydrocarbon (PAH) molecules are astrophysically particularly relevant for collision energies of less than 1 keV. In this regime, the interaction dynamics are dominated by elastic interactions. We have employed a molecular dynamics simulation based on analytical interaction potentials to model the interaction of low energy hydrogen and helium projectiles with isolated anthracene (C{sub 14}H{sub 10}) molecules. This approach allows for a very detailed investigation of the elastic interaction dynamics on an event by event basis. From the simulation data the threshold projectile kinetic energies above which direct C atom knock out sets in were determined. Anthracene differential energy transfer cross sections and total (dissociation) cross sections were computed for a wide range of projectile kinetic energies. The obtained results are interpreted in the context of PAH destruction in astrophysical environments.

  2. The response of Hyalella azteca to artificial sediments spiked with cadmium, zinc, and anthracene

    SciTech Connect

    Sawyer, L.N.; Burton, G.A. Jr.

    1995-12-31

    Two artificial sediment recipes with differing organic content have been found that give > 80%. control survival with Hyalella azteca in standard toxicity assays. To further explore the usefulness of these sediments, both were spiked with cadmium, zinc, and anthracene. Toxicity assays (96 hr.) were run at intervals up to 4 weeks post-spike. Consistent LC50 results were obtained for both sediments and both metals. Responses with the PAH were similar to the metals, but each test was placed under UV light to assess photo-induced toxicity. GC analysis on porewater indicates that anthracene either binds tightly to the sediment or is absorbed directly by Hyalella azteca. Toxicity decreased over time, perhaps due to this binding. Both sediments appear to be adequate as routine control sediments.

  3. Dansyl-anthracene dyads for ratiometric fluorescence recognition of Cu2+.

    PubMed

    Kaur, Kuljit; Kumar, Subodh

    2011-03-21

    Dansyl-anthracene dyads 1 and 2 in CH(3)CN-H(2)O (7:3) selectively recognize Cu(2+) ions amongst alkali, alkaline earth and other heavy metal ions using both absorbance and fluorescence spectroscopy. In absorbance, the addition of Cu(2+) to the solution of dyads 1 or 2 results in appearance of broad absorption band from 200 nm to 725 nm for dyad 1 and from 200 nm to 520 nm for dyad 2. This is associated with color change from colorless to blue (for 1) and fluorescent green (for 2). This bathochromic shift of the spectrum could be assigned to internal charge transfer from sulfonamide nitrogen to anthracene moiety. In fluorescence, under similar conditions dyads 1 and 2 on addition of Cu(2+) selectively quench fluorescence due to dansyl moiety between 520-570 nm (for 1)/555-650 nm (for 2) with simultaneous fluorescence enhancement at 470 nm and 505 nm for dyads 1 and 2, respectively. Hence these dyads provide opportunity for ratiometric analysis of 1-50 μM Cu(2+). The other metal ions viz. Fe(3+), Co(2+), Ni(2+), Cd(2+), Zn(2+), Hg(2+), Ag(+), Pb(2+), Li(+), Na(+), K(+), Mg(2+), Ca(2+), Ba(2+) do not interfere in the estimation of Cu(2+) except Cr(3+) in case of dyad 1. The coordination of dimethylamino group of dansyl unit with Cu(2+) causes quenching of fluorescence due to dansyl moiety between 520-600 nm and also restricts the photoinduced electron transfer from dimethylamino to anthracene moiety to release fluorescence between 450-510 nm. This simultaneous quenching and release of fluorescence respectively due to dansyl and anthracene moieties emulates into Cu(2+) induced ratiometric change.

  4. Effect of PEG and mPEG-anthracene on tRNA aggregation and particle formation.

    PubMed

    Froehlich, E; Mandeville, J S; Arnold, D; Kreplak, L; Tajmir-Riahi, H A

    2012-01-09

    Poly(ethylene glycol) (PEG) and its derivatives are synthetic polymers with major applications in gene and drug delivery systems. Synthetic polymers are also used to transport miRNA and siRNA in vitro. We studied the interaction of tRNA with several PEGs of different compositions, such as PEG 3350, PEG 6000, and mPEG-anthracene under physiological conditions. FTIR, UV-visible, CD, and fluorescence spectroscopic methods as well as atomic force microscopy (AFM) were used to analyze the PEG binding mode, the binding constant, and the effects of polymer complexation on tRNA stability, aggregation, and particle formation. Structural analysis showed that PEG-tRNA interaction occurs via RNA bases and the backbone phosphate group with both hydrophilic and hydrophobic contacts. The overall binding constants of K(PEG 3350-tRNA)= 1.9 (±0.5) × 10(4) M(-1), K(PEG 6000-tRNA) = 8.9 (±1) × 10(4) M(-1), and K(mPEG-anthracene)= 1.2 (±0.40) × 10(3) M(-1) show stronger polymer-RNA complexation by PEG 6000 and by PEG 3350 than the mPEG-anthracene. AFM imaging showed that PEG complexes contain on average one tRNA with PEG 3350, five tRNA with PEG 6000, and ten tRNA molecules with mPEG-anthracene. tRNA aggregation and particle formation occurred at high polymer concentrations, whereas it remains in A-family structure.

  5. (E)-4-[(4-nitrophenyl)diazenyl]phenyl anthracene-9-carboxylate.

    SciTech Connect

    Vance, Andrew L.; Zifer, Thomas; Nichol, Jessica L.; Rodriguez, Mark Andrew; Leonard, Francois Leonard; Wong, Bryan Matthew

    2008-10-01

    In the title compound, C{sub 27}H{sub 17}N{sub 3}O{sub 4}, the azo group displays a trans conformation and the dihedral angles between the central benzene ring and the pendant anthracene and nitrobenzene rings are 82.94 (7) and 7.30 (9){sup o}, respectively. In the crystal structure, weak C-H...O hydrogen bonds, likely associated with a dipole moment present on the molecule, help to consolidate the packing.

  6. Biodegradation of anthracene in the roots and growth substrate of poplar cuttings.

    PubMed

    Ballach, Hans-Joachim; Kuhn, Achim; Wittig, Rüdiger

    2003-01-01

    Following their exposure to anthracene, the roots of Populus nigra L. Loenen showed traces of 9 substances classed as products of biodegradation. The main substances detected were phthalic acid and 9,10-anthraquinone, followed by hydroxyanthracene and methoxyanthracene and five other compounds which could not be identified. Due to the relatively low concentration of degradation products found in the roots, further degradation to lower molecular compounds are discussed. The presence of 9,10-anthraquinone as the main product of the degradation of anthracene was also evident in the control tests with unplanted sandy substrate, although the content was higher in the planted series of tests. As a non-sterile approach was chosen, it may be assumed that a microbial degradation for 9,10-anthraquinone took place in the control series. However, it is difficult to differentiate clearly between a microbial degradation of anthracene in the substrate and metabolization in the roots due in part to the absence of specific degradation products in the various reaction areas.

  7. Coherent electronic energy transfer and nonlinear polariton effects in anthracene-doped naphthalene crystals

    SciTech Connect

    Connolly, M.A.

    1987-06-01

    The electronic energy transfer in strain-free mounted anthracene-doped naphthalene single crystals at frequencies near that of the (0,0) a-exciton in naphthalene was probed using sensitized resonant two-photon fluorescence excitation (TPE) and second harmonic generation (SHG) spectroscopies. The naphthalene-to-anthracene TPE intensity ratios were 1.2 and 1.6, for excitation of the zero-phonon transition at 1.6 and 20/sup 0/K, respectively. Energy transfer for the pure and the anthracene-doped naphthalene systems was in the capture limited regime, that is, the trapping event occurs on a timescale long compared to the migration of the excitation to the trap. The polariton trapping event is discussed in terms of scattering off a trap with subsequent trapping (i.e., capture) and scattering off a trap without subsequent trapping (i.e., trap scattering). The branching ratio for the trap scattering frequency to the capture frequency, was calculated to be 5 to 1 for the doped system. The branching ratio was used to determine the individual scattering frequencies. The lower bound for the coherent trapping or trap scattering radius was 100 A. Thermal broadening and temperature dependences of TPE and SHG signal intensities are discussed in terms of the polariton fusion model. The first report of a longitudinal exciton in a doped organic molecular system also is reported.

  8. Dual photochemistry of anthracene-9,10-endoperoxide studied by femtosecond spectroscopy.

    PubMed

    Lauer, Alexandra; Dobryakov, Alexander L; Kovalenko, Sergey A; Fidder, Henk; Heyne, Karsten

    2011-05-21

    The dual photochemistry of anthracene-9,10-endoperoxide (APO) was investigated in a fs UV pump-supercontinuum probe experiment, along with anthracene (AC) and anthraquinone (AQ) for comparison. Excitation of APO at 282 nm leads to 100% product formation by two competing photoreaction channels. Cycloreversion generates with a ∼25% quantum yield (QY) (1)O(2) and AC vibrationally excited in the singlet electronic ground state (hot AC). 1-2% of the AC is generated in the lowest triplet state, but no AC is generated in electronically excited singlet states. Generation and cooling of hot AC are modeled using solution phase and broadened gas-phase AC absorption spectra at various temperatures. Results indicate ultrafast generation of hot AC within 3 ps, much faster than reported before for derivatives of anthracene endoperoxide, and subsequent cooling with an 18 ps time constant. The homolytic O-O cleavage pathway generates a biradical, which converts into electronically excited diepoxide (DE). Our data indicate a 1.5 ps time constant that we tentatively assign to the biradical decay and DE formation. Cooling of DE in this electronically excited state takes place with a ∼21 ps time constant. Excitation of AQ at 266 nm is followed by an ultrafast population of the T(1)(nπ*) triplet state of AQ with a time constant of (160 ± 60) fs.

  9. Threshold photoelectron study of naphthalene, anthracene, pyrene, 1,2-dihydronaphthalene, and 9,10-dihydroanthracene

    NASA Astrophysics Data System (ADS)

    Mayer, Paul M.; Blanchet, Valerie; Joblin, Christine

    2011-06-01

    Threshold photoelectron spectra (TPESs) were obtained for naphthalene, anthracene, pyrene, 1,2-dihydronaphthalene, and 9,10-dihydroanthracene using imaging photoelectron photoion coincidence spectroscopy, from threshold to a photon energy of ˜20 eV. Outer valence Green's function calculations at the OVGF/cc-pVTZ level of theory were used to assign molecular orbitals to the observed TPES features. There is generally good agreement between the predicted and observed bands. Threshold regions for each molecule exhibit vibrational structure which is readily assigned based on previous PES studies. While the measured adiabatic ionization energies (IEa) for naphthalene, anthracene, and pyrene are in good agreement with previous works, new values are reported for the two dihydro species (1,2-dihydronaphthalene, 8.010 ± 0.010 eV and 9,10-dihydroanthracene, 8.335 ± 0.010 eV). A comparison is also made with the G3//B3LYP composite method, which consistently overestimates the IE values by 0.06-0.09 eV. The double ionization energies for anthracene and pyrene have been measured to be 19.3 ± 0.2 and 19.8 ± 0.2 eV, respectively.

  10. 1,8-Bis(phenylethynyl)anthracene - gas and solid phase structures.

    PubMed

    Lamm, Jan-Hendrik; Horstmann, Jan; Stammler, Hans-Georg; Mitzel, Norbert W; Zhabanov, Yuriy A; Tverdova, Natalya V; Otlyotov, Arseniy A; Giricheva, Nina I; Girichev, Georgiy V

    2015-09-07

    1,8-Bis(phenylethynyl)anthracene (1,8-BPEA) was synthesized by a twofold Kumada cross-coupling reaction. The molecular structure of 1,8-BPEA was determined using a combination of gas-phase electron diffraction (GED), mass spectrometry (MS), quantum chemical calculations (QC) and single-crystal X-ray diffraction (XRD). Five rotamers of the molecule with different orientations of phenylethynyl groups were investigated by DFT calculations. According to these, molecules of C2 symmetry with co-directional rotation of the phenylethynyl groups are predicted to exist in the gas phase at 498 K. This was confirmed by a GED/MS experiment at this temperature. The bonding of this conformer was studied and described in terms of an NBO-analysis. Dispersion interactions in the solid state structure and in the free molecule are discussed. In the solid this symmetry is broken; the asymmetric unit of the single crystal contains 3.5 molecules and a herringbone packing motif of π-stacked dimers and trimers. The π-stacking in the dimers is between the anthracene units, and the trimers are linked by π-stacking between phenyl and anthracene units. The interaction between these stacks can be described in terms of σ(C-H)π interactions.

  11. Degradation and mineralization of the polycyclic aromatic hydrocarbons anthracene and naphthalene in intertidal marine sediments

    SciTech Connect

    Bauer, J.E.; Capone, D.G.

    1985-07-01

    The degradation of the polynuclear aromatic hydrocarbons (PAHs) anthracene and naphthalene by the microbiota of intertidal sediments was investigated in laboratory studies. No mineralization of either PAH was observed in the absence of oxygen. Both rates and total amounts of PAH mineralization were strongly controlled by oxygen content and temperature of the incubations. Inorganic nitrogen and glucose amendments had minimal effects on PAH mineralization. The rates and total amounts of PAH mineralized were directly related to compound concentration, pre-exposure time, and concentration. Maximum mineralization was observed at the higher concentrations (5 to 100 ..mu..g/g (ppm)) of both PAHs. Optimal acclimation to anthracene and naphthalene (through pre-exposures to the compounds) occurred at the highest acclimation concentration (1,000 ppm). However, acclimation to a single concentration (100 ppm) resulted in initial relative mineralization rates over a range of re-exposure concentrations (1 to 1,000 ppm) being nearly identical. Maximum mineralization of both PAHs occurred after intermediate periods (1 to 2 weeks) of pre-exposure. The fraction of the total heterotrophic population capable of utilizing anthracene or naphthalene as sole carbon source was also greatest after 2 weeks.

  12. The effects of ultraviolet radiation and the polycyclic aromatic hydrocarbon, anthracene, on algae

    SciTech Connect

    Gala, W.R.

    1989-01-01

    The direct effects of ultraviolet (UV) radiation and the photoinduced toxicity of polycyclic aromatic hydrocarbons (PAH) to algae have been assessed. The penetration of solar UV radiation into offshore Lake Michigan was characterized. The direct effects of solar UV radiation to the primary production of natural phytoplankton assemblages in Lake Michigan was determined utilizing in situ incubations in chambers which selectively removed portions of the solar UV spectrum. A predictive hazard assessment model to estimate the impact of current and potential UV intensities on total lake productivity was developed. The photo-induced toxicity of the linear 3-ring PAH, anthracene, to the green alga, Selenastrum capricornutum, was characterized. The dose-response relationships among anthracene concentration, UV radiation intensity, and algal growth rate, {sup 14}C-bicarbonate incorporation, and flow cytometric endpoints were determined. The potential environmental hazard of PAH contamination to algal communities was assessed. Fluridone, a carotenoid biosynthesis inhibiting herbicide, was utilized to investigate possible sites and modes of toxic action and the protection provided by carotenoids in algal cells to the photo-induced toxicity of anthracene. It was concluded that solar UV radiation at current UV intensities can have considerable impact on natural algal communities through the direct effects of UV radiation and indirectly due to the photo-induced toxicity of PAH. However, stratospheric ozone depletion and the concomitant increase in solar UV radiation which is currently predicted will have negligible effects on primary production of phytoplankton assemblages in the Great Lakes.

  13. Impacts of bioremediation schemes for the mitigation of a low-dose anthracene contamination on free-living marine benthic nematodes.

    PubMed

    Louati, Hela; Ben Said, Olfa; Soltani, Amel; Cravo-Laureau, Cristiana; Preud'Homme, Hugues; Duran, Robert; Aissa, Patricia; Mahmoudi, Ezzeddine; Pringault, Olivier

    2014-03-01

    A microcosm experiment was used to examine (1) the effects of different bioremediation schemes on degradation of anthracene and the structure of free-living marine nematodes in a lightly contaminated (4.5 μg g(-1)) sediment from Bizerte lagoon and (2) the responses of the nematode community upon an artificial spiking of a low dose anthracene (1 μg g(-1)). For that purpose sediment microcosms were incubated in laboratory for 40 days. Bioremediation techniques decreased the anthracene contamination, and interestingly, biodegradation were more efficient when anthracene was artificial supplied into the sediment suggesting that the addition of bioavailable anthracene stimulated the bacterial community to adjust towards a PAH-degrading community. Spiking with this low dose of anthracene provoked significant changes in the nematode community structure and abundance, with the elimination of specific species such as Mesacanthion diplechma, the decrease of the dominant species Oncholaimus campylocercoides and the increase in abundance of opportunistic species such as Spirinia parasitifera. This would suggest a low tolerance of the nematode community despite the presence of a weak anthracene contamination in the sediment that could have allow dominance of an anthracene tolerant nematode species. Anthracene toxicity was alleviated in biostimulation treatments, leading to a strong increase in nematode abundance, concomitantly with changes in the nematode community structure; Prochromadorella neapolitana became the most abundant species.

  14. Benz[a]anthracene biotransformation and production of ring fission products by Sphingobium sp. strain KK22.

    PubMed

    Kunihiro, Marie; Ozeki, Yasuhiro; Nogi, Yuichi; Hamamura, Natsuko; Kanaly, Robert A

    2013-07-01

    A soil bacterium, designated strain KK22, was isolated from a phenanthrene enrichment culture of a bacterial consortium that grew on diesel fuel, and it was found to biotransform the persistent environmental pollutant and high-molecular-weight polycyclic aromatic hydrocarbon (PAH) benz[a]anthracene. Nearly complete sequencing of the 16S rRNA gene of strain KK22 and phylogenetic analysis revealed that this organism is a new member of the genus Sphingobium. An 8-day time course study that consisted of whole-culture extractions followed by high-performance liquid chromatography (HPLC) analyses with fluorescence detection showed that 80 to 90% biodegradation of 2.5 mg liter(-1) benz[a]anthracene had occurred. Biodegradation assays where benz[a]anthracene was supplied in crystalline form (100 mg liter(-1)) confirmed biodegradation and showed that strain KK22 cells precultured on glucose were equally capable of benz[a]anthracene biotransformation when precultured on glucose plus phenanthrene. Analyses of organic extracts from benz[a]anthracene biodegradation by liquid chromatography negative electrospray ionization tandem mass spectrometry [LC/ESI(-)-MS/MS] revealed 10 products, including two o-hydroxypolyaromatic acids and two hydroxy-naphthoic acids. 1-Hydroxy-2- and 2-hydroxy-3-naphthoic acids were unambiguously identified, and this indicated that oxidation of the benz[a]anthracene molecule occurred via both the linear kata and angular kata ends of the molecule. Other two- and single-aromatic-ring metabolites were also documented, including 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid and salicylic acid, and the proposed pathways for benz[a]anthracene biotransformation by a bacterium were extended.

  15. Benz[a]anthracene Biotransformation and Production of Ring Fission Products by Sphingobium sp. Strain KK22

    PubMed Central

    Kunihiro, Marie; Ozeki, Yasuhiro; Nogi, Yuichi; Hamamura, Natsuko

    2013-01-01

    A soil bacterium, designated strain KK22, was isolated from a phenanthrene enrichment culture of a bacterial consortium that grew on diesel fuel, and it was found to biotransform the persistent environmental pollutant and high-molecular-weight polycyclic aromatic hydrocarbon (PAH) benz[a]anthracene. Nearly complete sequencing of the 16S rRNA gene of strain KK22 and phylogenetic analysis revealed that this organism is a new member of the genus Sphingobium. An 8-day time course study that consisted of whole-culture extractions followed by high-performance liquid chromatography (HPLC) analyses with fluorescence detection showed that 80 to 90% biodegradation of 2.5 mg liter−1 benz[a]anthracene had occurred. Biodegradation assays where benz[a]anthracene was supplied in crystalline form (100 mg liter−1) confirmed biodegradation and showed that strain KK22 cells precultured on glucose were equally capable of benz[a]anthracene biotransformation when precultured on glucose plus phenanthrene. Analyses of organic extracts from benz[a]anthracene biodegradation by liquid chromatography negative electrospray ionization tandem mass spectrometry [LC/ESI(−)-MS/MS] revealed 10 products, including two o-hydroxypolyaromatic acids and two hydroxy-naphthoic acids. 1-Hydroxy-2- and 2-hydroxy-3-naphthoic acids were unambiguously identified, and this indicated that oxidation of the benz[a]anthracene molecule occurred via both the linear kata and angular kata ends of the molecule. Other two- and single-aromatic-ring metabolites were also documented, including 3-(2-carboxyvinyl)naphthalene-2-carboxylic acid and salicylic acid, and the proposed pathways for benz[a]anthracene biotransformation by a bacterium were extended. PMID:23686261

  16. Control of the intermolecular photodimerization of anthracene derivatives by hydrogen bonding of urea groups in dilute solution.

    PubMed

    Matsumoto, Hisato; Nishimura, Yoshinobu; Arai, Tatsuo

    2016-08-04

    The photodimerization reaction of anthracene derivatives was performed by capitalizing on intermolecular hydrogen bonds. Anthracene derivatives that can control the dimerization reaction depending on the substitution site were designed by using two anthryl moieties and one urea group, referred to as N,N'-dianthracen-n-ylurea, nDAU (n = 1, 2 and 9), which are symmetrically substituted by 1-anthryl, 2-anthryl and 9-anthryl groups, respectively. We investigated the excimer emission and photodimerization reaction of these anthracene-urea derivatives using absorption, emission, and (1)H NMR spectroscopy along with fluorescence decay measurements. All derivatives showed a concentration dependence of their fluorescence spectra and multiple fluorescence lifetime components even at 10(-6) M. Significantly, 9DAU resulted in an intermolecular photodimerization reaction. These differences in photoreactivity of nDAU may depend on variations in the overlap of the intermolecularly associated anthracene rings of nDAU by hydrogen bonding between intermolecular urea moieties. Furthermore, the dimerization quantum yield of 9DAU was reduced by the addition of tetrabutylammonium acetate (TBAAc). Consequently, we revealed that the substitution site and the addition of TBAAc affected the dimerization reaction of anthracene-urea derivatives.

  17. Data on synthesis and thermo-mechanical properties of stimuli-responsive rubber materials bearing pendant anthracene groups.

    PubMed

    Manhart, Jakob; Ayalur-Karunakaran, Santhosh; Radl, Simone; Oesterreicher, Andreas; Moser, Andreas; Ganser, Christian; Teichert, Christian; Pinter, Gerald; Kern, Wolfgang; Griesser, Thomas; Schlögl, Sandra

    2016-12-01

    The photo-reversible [4πs+4πs] cycloaddition reaction of pendant anthracene moieties represents a convenient strategy to impart wavelength dependent properties into hydrogenated carboxylated nitrile butadiene rubber (HXNBR) networks. The present article provides the (1)H NMR data on the reaction kinetics of the side chain functionalization of HXNBR. 2-(Anthracene-9-yl)oxirane with reactive epoxy groups is covalently attached to the polymer side chain of HXNBR via ring opening reaction between the epoxy and the carboxylic groups. Along with the identification, (1)H NMR data on the quantification of the attached functional groups are shown in dependence on reaction time and concentration of 2-(anthracene-9-yl)oxirane. Changes in the modification yield are reflected in the mechanical properties and DMA data of photo-responsive elastomers are illustrated in dependence on the number of attached anthracene groups. DMA curves over repeated cycles of UV induced crosslinking (λ>300 nm) and UV induced cleavage (λ=254 nm) are further depicted, demonstrating the photo-reversibility of the thermo-mechanical properties. Interpretation and discussion of the data are provided in "Design and application of photo-reversible elastomer networks by using the [4πs+4πs] cycloaddition reaction of pendant anthracene groups" (Manhart et al., 2016) [1].

  18. Identification of various laccases induced by anthracene and contribution to its degradation in a Mediterranean coastal pine litter.

    PubMed

    Qasemian, Leila; Guiral, Daniel; Belghazi, Maya; Ferré, Elisée; Gros, Raphaël; Farnet, Anne-Marie

    2011-09-01

    Mediterranean coastal ecosystems are known to be highly subject to natural and anthropic environmental stress. In this study, we examine the effects of anthracene as a common pollutant on the total microbial communities from a Pinus halepensis litter of a typical Mediterranean coastal site (Les Calanques, Marseille). The main objective was to identify the microbial factors leading the resilience of this ecosystem. Two questions were addressed: (i) how lignin-degrading enzymes (Laccase, Lignin-peroxidase and Mn-peroxidase) are affected by the presence of this molecule, (ii) whether the indigenous consortia are involved in its degradation in mesocosms under favorable incubation conditions (25 °C, 60% WHC) and after different time intervals (1 and 3 month(s)). We found a strong increase in laccase production in the presence of anthracene after 3 months, together with anthracene degradation (28%±5). Moreover 9,10-anthraquinone is detected as the product of anthracene oxidation after 3 months. However neither lignin-peroxidase activity nor Mn-peroxidase activity is detected. Laccase proteins directly extracted from litter were sequenced via Nano-LC-MS/MS and reveal twelve different peptide sequences induced by the presence of anthracene in the mesocoms. Our study confirms the major detoxification role of this enzymatic system and highlights the high degradation potential of fungal species inhabiting P. halepensis litter, a factor in the resilience of Mediterranean ecosystems.

  19. An integrated biomarker response index for the mussel Mytilus edulis based on laboratory exposure to anthracene and field transplantation experiments

    NASA Astrophysics Data System (ADS)

    Yuan, Mengqi; Wang, You; Zhou, Bin; Jian, Xiaoyang; Dong, Wenlong; Tang, Xuexi

    2016-10-01

    Organic pollution is a serious environmental problem in coastal areas and it is important to establish quantitative methods for monitoring this pollution. This study screened a series of sensitive biomarkers to construct an integrated biomarker response (IBR) index using Mytilus edulis. Mussels were exposed to the polycyclic aromatic hydrocarbon anthracene under controlled laboratory conditions and the activities of components of the glutathione antioxidant system, and the concentrations of oxidative-damage markers, were measured in the gills and digestive glands. Anthracene exposure resulted in increased levels of malondialdehyde (MDA) and superoxide radicals (O{2/-}•), indicating that oxidative damage had occurred. Correspondingly, anthracene exposure induced increased activities of glutathione S -transferase (GST), glutathione peroxidase (GPx) and reduced glutathione (GSH) in digestive glands, and GPx and glutathione reductase (GR) in gills, consistent with stimulation of the antioxidant system. A field experiment was set up, in which mussels from a relatively clean area were transplanted to a contaminated site. One month later, the activities of GST, GPx and GR had increased in several tissues, particularly in the digestive glands. Based on the laboratory experiment, an IBR, which showed a positive relationship with anthracene exposure, was constructed. The IBR is suggested to be a potentially useful tool for assessing anthracene pollution.

  20. Iptycene synthesis: A new method for attaching a 2,3-anthracene moiety to the 9,10-positions of another anthracene moiety - Exceptional conditions for a Lewis acid catalyzed Diels-Alder reaction

    NASA Technical Reports Server (NTRS)

    Chen, Yong-Shing; Hart, Harold

    1989-01-01

    An efficient three-step method for appending a 2,3-anthracene moiety to the 9,10-positions of an existing anthracene moiety is described. The first step uses excess 1,4-anthraquinone (3 equiv) and aluminum chloride (6 equiv) to obtain the anthracene-quinone cycloadduct (omission of the AlCl3 resulted in no adduct). The resulting diketone was reduced to the corresponding diol (excess LiAlH4), which was dehydrated to the arene with phosphorus oxychloride and pyridine. Specific examples include the preparation of heptipycene 8 from pentiptycene 6 (66 percent overall yield) and a similar conversion of 8 to the noniptycene 13 (75 percent overall yield). The methodology led to a markedly improved synthesis of tritriptycene 9 and the first synthesis of undecaiptycene 14.

  1. The combined effect of anthracene and cadmium on photosynthetic activity of three Desmodesmus (Chlorophyta) species.

    PubMed

    Pokora, Wojciech; Tukaj, Zbigniew

    2010-09-01

    Individual toxicity of heavy metals (HM) and polycyclic aromatic hydrocarbons (PAH) to plants living in water bodies is well-documented. In view of frequent joint occurrence of these compounds in the environment, plants are subjected to damage from their combined action. Cadmium and anthracene can generate production of reactive oxygen species (ROS). We have recently detected elevated activity of Fe- and Mn-SOD isoforms, indicating chloroplast and mitochondrion as the main sites of combined toxicity of HM and PAH. In the present paper, short-term (1-24 h) experiments on the mechanism of combined toxicity of anthracene and cadmium to the photosynthesis of three Desmodesmus species are reported. Inhibition, stimulation or no effect on the oxygen evolution was observed following the treatment with the contaminants when applied either separately or jointly. The response pattern was both strongly species- and time-dependent. In contrast, the photosynthetic activity of cells, expressed by chlorophyll fluorescence parameters, was substantially unaffected, since no effect or, in several cases, a slight stimulation of PS II quantum efficiency (Phi PS II) were noted. A characteristic relationship between the SOD activity and the qN values was observed. The treatment of Desmodesmus cells with anthracene or cadmium had either no effect or slightly enhanced either the SOD activity or the qN value, whereas the mixture of the contaminants resulted in a multifold increase in both the SOD activity and the qN values. The results suggest that chloroplasts of algae are well protected against the combined action of the two contaminants the toxicity of which should be attributed to nucleocytoplasmic compartments and reproductive processes of the cell cycle.

  2. Novel method for determination of anthracene by coupling dispersive liquid-liquid extraction to first-derivative synchronous spectrofluorimetry.

    PubMed

    Abdel-Aziz, Omar; El Kosasy, A M; El-Sayed Okeil, Sherif Mahmoud

    2014-05-01

    A novel method could be adopted successfully for determination of anthracene in environmental samples, utilizing dispersive liquid-liquid extraction followed by first-derivative synchronous fluorimetry at a constant wavelength difference Δλ = 165 nm, where a linear calibration curve was obtained in a concentration range of 0.5-100 ng mL(-1) at 244 nm. The detection limit was 0.1 ng mL(-1). The method can be easily adopted for determination of anthracene in aqueous media including tap water and river water. The recoveries obtained were 85.40-108.02%. The proposed method was validated according to International Conference of Harmonization (ICH) guide lines and successfully applied to determine anthracene in pure form and in water samples including real life water samples from different sources. All the results obtained were compared with those of published method, where no a significant difference was observed.

  3. Removal of Anthracene and Fluoranthene by Waxy Corn, Long Bean and Okra in Lead-Contaminated Soil.

    PubMed

    Somtrakoon, Khanitta; Chouychai, Waraporn; Lee, Hung

    2015-09-01

    The ability of waxy corn, long bean and okra to remove two polycyclic aromatic hydrocarbons (PAHs) from soil containing 0.63 mg Pb kg(-1) dry soil was assessed. The presence of Pb did not reduce the ability of these plants to remove the PAHs from soil. About 49 % of anthracene and 77 % of fluoranthene were removed from Pb-spiked or non-spiked soil, respectively, after 30 days. Among the plants, okra was the most efficient at removing anthracene and fluoranthene in the presence or absence of Pb in soil after 30 days. Pb did not affect fluoranthene removal, but stimulated the removal of anthracene, by long bean, waxy corn and okra. However, growth of long bean and waxy corn was poor in Pb-spiked soil and waxy corn plants died around 22 days after transplantation. The results show some promise in using plants to remove PAHs from soil which is also co-contaminated with Pb.

  4. Kinetics and selectivity of oxidation of saturated hydrocarbons in sulphuric acid media containing anthracene and cyclohexane oligomers

    SciTech Connect

    Rudakov, Ye.S.; Lutsyk, A.I.; Suikov, S.Yu.; Tishchenko, N.A.

    1983-01-01

    Solutions of anthracene and cyclohexene in 93% sulphuric acid are sources of fairly stable species, which oxidize tertiary and secondary C-H bonds of saturated hydrocarbons at 90/sup 0/C. A study was made of kinetics and selectivity of the first stage of oxidation of paraffins in these systems. The selectivity, isotope effect and kinetics of oxidation of the anthraceneH/sub 2/SO/sub 4/ system and oligomers of cyclohexene-H/sub 2/SO/sub 4/ are similar and approximate to the oxidizing agent-sulphuric acid systems, previously examined. Based on this analogy a mechanism is proposed for the oxidative homolysis of C-H bonds for the first stage of oxidation of saturated hydrocarbons in anthracene-sulphuric acid and cyclohexene-sulphuric acid systems.

  5. Intersystem Crossing Mechanisms and Single Molecule Fluorescence: Terrylene in Anthracene Crystals

    SciTech Connect

    Kol'chenko, M.A.; Nicolet, A.; Orrit, M.; Kozankiewicz, B.

    2005-05-15

    Single molecule spectroscopy requires molecules with low triplet yields and/or short triplet lifetimes. The intersystem crossing (ISC) rate may be dramatically enhanced by the host matrix. Comparing the fluorescence intensity of single terrylene molecules in para-terphenyl, naphthalene, and anthracene crystals, we found a reduction of the saturation intensity by three orders of magnitude in the latter case. The fluorescence autocorrelation function indicates that the bottleneck state is the terrylene triplet. We propose a ping-pong mechanism between host and guest. This intermolecular ISC mechanism, which can open whenever the host triplet lies lower than the guest singlet, was overlooked in previous single molecule investigations.

  6. Intramolecular vibrational energy redistribution in bridged azulene-anthracene compounds: Ballistic energy transport through molecular chains

    NASA Astrophysics Data System (ADS)

    Schwarzer, D.; Kutne, P.; Schröder, C.; Troe, J.

    2004-07-01

    Intramolecular vibrational energy flow in excited bridged azulene-anthracene compounds is investigated by time-resolved pump-probe laser spectroscopy. The bridges consist of molecular chains and are of the type (CH2)m with m up to 6 as well as (CH2OCH2)n (n=1,2) and CH2SCH2. After light absorption into the azulene S1 band and subsequent fast internal conversion, excited molecules are formed where the vibrational energy is localized at the azulene side. The vibrational energy transfer through the molecular bridge to the anthracene side and, finally, to the surrounding medium is followed by probing the red edge of the azulene S3 absorption band at 300 nm and/or the anthracene S1 absorption band at 400 nm. In order to separate the time scales for intramolecular and intermolecular energy transfer, most of the experiments were performed in supercritical xenon where vibrational energy transfer to the bath is comparably slow. The intramolecular equilibration proceeds in two steps. About 15%-20% of the excitation energy leaves the azulene side within a short period of 300 fs. This component accompanies the intramolecular vibrational energy redistribution (IVR) within the azulene chromophore and it is caused by dephasing of normal modes contributing to the initial local excitation of the azulene side and extending over large parts of the molecule. Later, IVR in the whole molecule takes place transferring vibrational energy from the azulene through the bridge to the anthracene side and thereby leading to microcanonical equilibrium. The corresponding time constants τIVR for short bridges increase with the chain length. For longer bridges consisting of more than three elements, however, τIVR is constant at around 4-5 ps. Comparison with molecular dynamics simulations suggests that the coupling of these chains to the two chromophores limits the rate of intramolecular vibrational energy transfer. Inside the bridges the energy transport is essentially ballistic and, therefore

  7. Lowest optical excitations in molecular crystals: bound excitons versus free electron-hole pairs in anthracene.

    PubMed

    Hummer, Kerstin; Puschnig, Peter; Ambrosch-Draxl, Claudia

    2004-04-09

    By solving the Bethe-Salpeter equation for the electron-hole Green function for crystalline anthracene we find the lowest absorption peak generated by strongly bound excitons or by a free electron-hole pair, depending on the polarization direction being parallel to the short or the long molecular axis, respectively. Both excitations are shifted to lower energies by pressure. The physical difference of these excitations is apparent from the electron-hole wave functions. Our findings are a major contribution to solve the long-standing puzzle about the nature of the lowest optical excitations in organic materials.

  8. Free Volume and Gas Permeation in Anthracene Maleimide-Based Polymers of Intrinsic Microporosity

    PubMed Central

    Khan, Muntazim Munir; Filiz, Volkan; Emmler, Thomas; Abetz, Volker; Koschine, Toenjes; Rätzke, Klaus; Faupel, Franz; Egger, Werner; Ravelli, Luca

    2015-01-01

    High free-volume copolymers were prepared via polycondensation with 2,3,5,6,-tetrafluoroterephthalonitrile (TFTPN) in which a portion of the 3,3,3',3'-tetramethyl-1,1'-spirobisindane (TTSBI) of PIM-1 was replaced with dibutyl anthracene maleimide (4bIII). An investigation of free volume using positron annihilation lifetime spectroscopy (PALS), and gas permeation measurements was carried out for the thin film composite copolymer membranes and compared to PIM-1. The average free volume hole size and the gas permeance of the copolymer membranes increased with decreasing TTSBI content in the copolymer. PMID:26030881

  9. Synthesis, characterization, optical and electrical properties of bis(phenylvinyl)anthracene-based polymers

    NASA Astrophysics Data System (ADS)

    Mansour, Nadia; Hriz, Khaled; Jaballah, Nejmeddine; Kreher, David; Majdoub, Mustapha

    2016-08-01

    A series of bis(phenylvinyl)anthracene-based polymers containing different lengths of polar ethylene glycol groups in the main chain (P1-3) were efficiently synthesized by Wittig polycondensation. These polymers are fully soluble in volatile solvents, which helped a lot to obtain high quality films. Moreover, these semi-conducting materials exhibited semi-crystalline morphology with relatively high glass transition temperature. In this article, the UV-visible absorption and fluorescence properties of P1-3 were studied consequently both in solution and as thin solid film: tan absorption-onset at 433 nm was observed and all these bis(phenylvinyl)anthracene-based polymers (P1-3) show a blue emission in solution, fluorescence quantum efficiencies being respectively 52% for P1, 75% for P2 and 67% for P3. In addition, the HOMO/LUMO energy levels were evaluated by cyclic voltammetry measurements and indicate a p-type semi-conducting materials. Finally, the electrical properties of P1-3 were investigated by recording current-tension characteristics and these experimental results were modeled by the current space-charge-limited (SCLC) mechanism.

  10. Triplet states in isotopically mixed anthracene crystals: High resolution optical spectroscopy

    NASA Astrophysics Data System (ADS)

    Port, H.; Rund, D.; Wolf, H. C.

    1981-08-01

    The triplet O,O transitions of guest and host in isotopically mixed anthracene crystals of various compositions (A- h10, 13C-monosubstituted A- h10, A- d1h9, A- d2hg in A- d10 and A- d10 in A- h10) have been investigated using high resolution laser excitation spectroscopy. The guest aggregate spectra have been studied in polarized light as a function of guest concentration up to 15%. The analyses allow us to identify the monomer, dimer and trimer lines. From the dimer splittings the dominant resonance pair interactions are dedu The comparison of different mixed crystal systems with guest levels below and above the host exciton band reveals that quasiresonance and superexchange corrections are of minor importance. The experimental resonance pair interactions are used to calculate the triplet exciton band structure of anthracen and the observed guest polarization behaviour is interpreted quantitatively by the Rashba effect. Finally, the lower Davydov component of the host is s and broadened with increasing guest concentration. The shift is discussed using a theoretical model of Lifshitz.

  11. Synthesis, magnetic properties and dynamic behavior of cobalt complexes with an anthracene-containing dioxolene ligand.

    PubMed

    Katayama, Koichi; Hirotsu, Masakazu; Kinoshita, Isamu; Teki, Yoshio

    2014-09-21

    The anthracene-functionalized cobalt complexes [Co(L)(TPA)]PF6 (1) and [Co(L)(Me(n)TPA)]PF6 (2, n = 1; 3, n = 2; 4, n = 3) were synthesized by the combination of 9-(3,4-dihydroxyphenyl)anthracene (H2L) and tris(2-pyridylmethyl)amine (TPA) or its derivatives (Me(n)TPA, n = 1, 2, 3). Characterization of complexes 1-4 was performed by UV-vis absorption, IR, (1)H NMR, and magnetic susceptibility measurements. In the solid state, the variable-temperature magnetic susceptibility data showed that complex 1 is low-spin cobalt(III) catecholate (Co(III)(LS)-Cat), while complex 4 is high-spin cobalt(II) semiquinonate (Co(II)(HS)-SQ) in the range 4.5-400 K. The susceptibility data of complexes 2 and 3 suggested valence tautomerism between the Co(III)(LS)-Cat and Co(II)(HS)-SQ forms. Light-induced valence tautomerism was observed in complexes 2 and 3 at 5 K by photo-irradiation. In solution, the temperature dependence of (1)H NMR spectra of 1 and 2 showed an equilibrium between their geometrical isomers.

  12. On an electron diffraction study of the structures of anthraquinone and anthracene

    NASA Astrophysics Data System (ADS)

    Ketker, S. N.; Kelley, M.; Fink, M.; Ivey, R. Charles

    1981-11-01

    The molecular structures of gaseous anthraquinone and anthracene have been studied by electron diffraction at nozzle tip temperatures of about 160°C and 135°C, respectively. Each molecule has D 2h symmetry to within experimental error. Anthraquinone resembles two benzene rings linked by ketone bridges with the bond distances ( ra) and bond angle given by r(CH) = 1.087(4) Å, r(CO) = 1.220(2) Å, r(C 9C 11)= 1.499(2) A, r(C 1C 11) = r(C 1 C 2) = r(C 2C 3) = r(C 11C 12)= 1.400(2) Å, ∠C 12C 10C 13 = 117.4(4)°, ∠C1C11C12= 120.1(2)°. For anthracene the bond lengths (r a) and the bond angles are r(CH) = 1.085 A (assumed), r(C 9C 11) = 1.392(6) Å, r(C 11C 1) = 1.437(4) Å, r(C 1C 2) = 1.397(4) Å, r(C 2C 3) = 1.422(16) Å, r(C 11C 12.)= 1.437(4) Å, ∠C 12.C 10C 13= 112(1)°, ∠C 1, C 11C 12 = 118.8(6)°.

  13. Stereoselective metabolism of anthracene and phenanthrene by the fungus Cunninghamella elegans

    SciTech Connect

    Cerniglia, C.E.; Yang, S.K.

    1984-01-01

    The fungus Cunninghamella elegans oxidized anthracene and phenanthrene to form predominately transdihydrodiols. The metabolites were isolated by reversed-phase high-pressure liquid chromatography for structural and conformational analyses. Comparison of the circular dichroism spectrum of the fungal trans-1,2-dihydroxy-1,2-dihydroanthracene to that formed by rat liver microsomes indicated that the major enantiomer of the trans-1,2-dihydroxy-1,2-dihydroanthracene formed by C. elegans had an S,S absolute stereochemistry, which is opposite to the predominately 1R,2R dihydrodiol formed by rat liver microsomes. C. elegans oxidized phenanthrene primarily in the 1,2-positions to form trans-1,2-dihydroxy-1,2-dihydrophenanthrene. In addition, a minor amount of trans-3,4-dihydroxy-3,4-dihydrophenanthrene was detected. Metabolism at the K-region (9,10-positions) of phenanthrene was not detected. Comparison of the circular dichroism spectra of the phenanthrene trans-1,2- and trans-3,4-dihydrodiols formed by C. elegans to those formed by mammalian enzymes indicated that each of the dihydrodiols formed by C. elegans had an S,S absolute configuration. The results indicate that there are differences in both the regio- and stereoselective metabolism of anthracene and phenanthrene between the fungus C. elegans and rat liver microsomes. 26 references.

  14. Estimation of transport and degradation parameters for naphthalene and anthracene: influence of mass transfer on kinetics.

    PubMed

    Owabor, Chiedu N; Ogbeide, Samuel E; Susu, Alfred A

    2010-10-01

    The method of temporal moment solutions (MOM) for one-dimensional convective-dispersive solute transport involving linear equilibrium sorption and first-order degradation for time pulse sources has been applied to analyze experimental data from a soil microcosm reactor. Estimation of the pore water velocity V for a nonreactive solute was aided by the use of only the first normalized moment while the dispersion coefficient D, first-order degradation rate constant lambda, and the retardation factor R were estimated using both first and second normalized moments. These transport and degradation parameters were compared to those obtained by a transport model using a nonlinear least square curve-fitting program CXTFIT (version 2.0). Results obtained showed that the MOM fits the breakthrough curve with tailing better than the CXTFIT. The initial estimates of these parameters aided the reduction of the dimensionality of the search process of the non- steady-state model. A residual concentration of 1.12E-5 and 1.48 mg/l for naphthalene and 7.67E-4 and 1.61 mg/l for anthracene, in the axial and radial directions, respectively, suggests the preference of naphthalene during the biodegradation process. The surface concentration as depicted using three-dimensional plots showed that there is occlusion of the aromatics (naphthalene and anthracene) within the soil micropores, thereby limiting their bioavailability and in the long run increasing their toxicity.

  15. An optically and thermally switchable electronic structure based on an anthracene-BODIPY conjugate.

    PubMed

    Aotake, Tatsuya; Suzuki, Mitsuharu; Tahara, Kazuaki; Kuzuhara, Daiki; Aratani, Naoki; Tamai, Naoto; Yamada, Hiroko

    2015-03-23

    An optically and thermally responsive boron dipyrromethene (BODIPY) dye, namely, meso-2-(9,10-dihydro-9,10-ethanoanthracene-11,12-dione) (DK)-linked, bicyclo[2.2.2]octadiene (BCOD)-fused BODIPY (BCOD-DK), was synthesized. The weakly luminous structure of BCOD-DK can be changed quantitatively to that of the strongly fluorescent BODIPY BCOD-Ant by optical excitation at the DK unit, which induces double decarbonylation of the DK unit to give an anthracene unit. The solvent effect on the fluorescence properties of BCOD-DK suggests that the dramatic change in fluorescence intensity is controlled by intramolecular electron transfer from the BODIPY moiety to the meso-DK substituent. BCOD-DK is converted to meso-DK benzene-fused BODIPY (Benzo-DK) by heating at 220 °C with 64-70 nm redshift of absorption and fluorescence peaks without changing the fluorescence quantum yield of ΦF =0.08 in dichloromethane. Benzo-DK can be converted to strongly fluorescent meso-anthracene benzene-fused BODIPY Benzo-Ant by optical excitation. Thus, BCOD-DK can show four different optical performances simply by irradiation and heating, and hence may be applicable for optical data storage and security data encryption.

  16. Direct effects of 9-anthracene compounds on cystic fibrosis transmembrane conductance regulator gating

    PubMed Central

    Ai, T.; Bompadre, S. G.; Sohma, Y.; Wang, X.; Li, M.; Sohma, Y.; Ai, T.

    2005-01-01

    Anthracene-9-carboxylic acid (9-AC) has been reported to show both potentiation and inhibitory effects on guinea-pig cardiac cAMP-activated chloride channels via two different binding sites, and inhibition of Mg2+-sensitive protein phosphatases has been proposed for the mechanism of 9-AC potentiation effect. In this study, we examined the effects of 9-AC on wild-type and mutant human cystic fibrosis transmembrane conductance regulator (CFTR) chloride channels expressed in NIH3T3 or CHO cells. 9-AC inhibits whole-cell CFTR current in a voltage-dependent manner, whereas the potentiation effect is not affected by membrane potentials. Anthracene-9-methanol, an electro-neutral 9-AC analog, fails to block CFTR, but shows a nearly identical potentiation effect, corroborating the idea that two chemically distinct sites are responsible, respectively, for potentiation and inhibitory actions of 9-AC. 9-AC also enhances the activity of ΔR-CFTR, a constitutively active CFTR mutant whose R-domain is removed. In excised inside-out patches, 9-AC increases Po by prolonging the mean burst durations and shortening the interburst durations. We therefore conclude that two different 9-AC binding sites for potentiation and inhibitory effects on CFTR channels are located outside of the R-domain. We also speculate that 9-AC potentiates CFTR activity by directly affecting CFTR gating. PMID:15290302

  17. Cooling of isolated anthracene cations probed with photons of different wavelengths in the Mini-Ring

    NASA Astrophysics Data System (ADS)

    Ji, M.; Bernard, J.; Chen, L.; Brédy, R.; Ortéga, C.; Joblin, C.; Cassimi, A.; Martin, S.

    2017-01-01

    We report on a direct measurement of the Internal Energy Distribution (IED) shift rate of an initially hot polycyclic aromatic hydrocarbon (PAH) molecular ensemble, anthracene cations (C14H10 +) . The ions were produced in an electron cyclotron resonance (ECR) ion source and stored in an electrostatic ion storage ring, the Mini-Ring. Laser pulses of two wavelengths were sent successively to merge the stored ion bunch at different storage times to enhance the neutral fragment yield due to fast laser induced dissociation. Using this technique, we have been able to determine directly the energy shift rate of the IED, without involving any theoretical simulation or any assumption on dissociation rates, cooling rates, or the initial IED. Theoretical energy shift rates have been estimated from the evolution of simulated IEDs by taking into account the effects of the unimolecular dissociation and two radiative decay mechanisms: the Poincaré fluorescence and the infrared vibrational emission. The comparison between the experimental results and the model provides new evidence of the important role of the Poincaré fluorescence in the overall cooling process of anthracene cations. Although in the short time range the commonly accepted intuition says that the cooling would result mostly from the dissociation of the hottest ions (depletion cooling), we demonstrate that the Poincaré fluorescence is the dominant contribution (about 85%) to the net cooling effect.

  18. Oxidative metabolism of phenanthrene and anthracene by soil pseudomonads. The ring-fission mechanism

    PubMed Central

    Evans, W. C.; Fernley, H. N.; Griffiths, E.

    1965-01-01

    1. Phenanthrene is oxidatively metabolized by soil pseudomonads through trans-3,4-dihydro-3,4-dihydroxyphenanthrene to 3,4-dihydroxyphenanthrene, which then undergoes cleavage. 2. Some properties of the ring-fission product, cis-4-(1-hydroxynaphth-2-yl)-2-oxobut-3-enoic acid, are described. The Fe2+-dependent oxygenase therefore disrupts the bond between C-4 and the angular C of the phenanthrene nucleus. 3. An enzyme of the aldolase type converts the fission product into 1-hydroxy-2-naphthaldehyde (2-formyl-1-hydroxynaphthalene). An NAD-specific dehydrogenase is also present in the cell-free extract, which oxidizes the aldehyde to 1-hydroxy-2-naphthoic acid. This is then oxidatively decarboxylated to 1,2-dihydroxynaphthalene, thus allowing continuation of metabolism via the naphthalene pathway. 4. Anthracene is similarly metabolized, through 1,2-dihydro-1,2-dihydroxyanthracene to 1,2-dihydroxyanthracene, in which ring-fission occurs to give cis-4-(2-hydroxynaphth-3-yl)-2-oxobut-3-enoic acid. The position of cleavage is again at the bond between the angular C and C-1 of the anthracene nucleus. 5. Enzymes that convert the fission product through 2-hydroxy-3-naphthaldehyde into 2-hydroxy-3-naphthoic acid were demonstrated. The further metabolism of this acid is discussed. 6. The Fe2+-dependent oxygenase responsible for cleavage of all the o-dihydroxyphenol derivatives appears to be catechol 2,3-oxygenase, and is a constitutive enzyme in the Pseudomonas strains used. PMID:14342521

  19. New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties

    NASA Astrophysics Data System (ADS)

    Sek, Danuta; Siwy, Mariola; Grucela, Marzena; Małecki, Grzegorz; Nowak, Elżbieta M.; Lewinska, Gabriela; Santera, Jerzy; Laba, Katarzyna; Lapkowski, Mieczyslaw; Kotowicz, Sonia; Schab-Balcerzak, Ewa

    2017-03-01

    The new Schiff bases bearing anthracene unit were synthesized from 2-aminoanthracene and various aldehydes such as: benzaldehyde, 4-(diphenylamino)benzaldehyde, 9-phenanthrenecarboxaldehyde, 9-anthracenecarboxaldehyde, and biphenyl-4-carboxaldehyde, 2-naphthaldehyde. Resulted azomethines were characterized by IR, NMR (1H and 13C), elemental analysis and UV-vis spectroscopy. The imine consists of anthracene and biphenyl moieties exhibited liquid crystal properties and their nematic phase showed Schlieren texture. The photoluminescence measurements carried out in solution and in solid state as blend with PMMA revealed the ability of the imines to emission of the blue light with quantum yield efficiency in the range of 2.18-6.03% in blend. Based on the electrochemical experiment they showed value of energy gap (Eg) in the range of 2.5-2.7 eV. Additionally, density functional theory (DFT) was applied for calculations of both electronic structure and spectroscopic properties of synthesized Schiff bases. Moreover, the results obtained from preliminary tests of application of the azomethines in organic photovoltaic (OPV) devices confirmed their electron acceptor character.

  20. New anthracene-based Schiff bases: Theoretical and experimental investigations of photophysical and electrochemical properties.

    PubMed

    Sek, Danuta; Siwy, Mariola; Grucela, Marzena; Małecki, Grzegorz; Nowak, Elżbieta M; Lewinska, Gabriela; Santera, Jerzy; Laba, Katarzyna; Lapkowski, Mieczyslaw; Kotowicz, Sonia; Schab-Balcerzak, Ewa

    2017-03-15

    The new Schiff bases bearing anthracene unit were synthesized from 2-aminoanthracene and various aldehydes such as: benzaldehyde, 4-(diphenylamino)benzaldehyde, 9-phenanthrenecarboxaldehyde, 9-anthracenecarboxaldehyde, and biphenyl-4-carboxaldehyde, 2-naphthaldehyde. Resulted azomethines were characterized by IR, NMR ((1)H and (13)C), elemental analysis and UV-vis spectroscopy. The imine consists of anthracene and biphenyl moieties exhibited liquid crystal properties and their nematic phase showed Schlieren texture. The photoluminescence measurements carried out in solution and in solid state as blend with PMMA revealed the ability of the imines to emission of the blue light with quantum yield efficiency in the range of 2.18-6.03% in blend. Based on the electrochemical experiment they showed value of energy gap (Eg) in the range of 2.5-2.7eV. Additionally, density functional theory (DFT) was applied for calculations of both electronic structure and spectroscopic properties of synthesized Schiff bases. Moreover, the results obtained from preliminary tests of application of the azomethines in organic photovoltaic (OPV) devices confirmed their electron acceptor character.

  1. The role of the van der Waals interactions in the adsorption of anthracene and pentacene on the Ag(111) surface.

    PubMed

    Morbec, Juliana M; Kratzer, Peter

    2017-01-21

    Using first-principles calculations based on density-functional theory (DFT), we investigated the effects of the van der Waals (vdW) interactions on the structural and electronic properties of anthracene and pentacene adsorbed on the Ag(111) surface. We found that the inclusion of vdW corrections strongly affects the binding of both anthracene/Ag(111) and pentacene/Ag(111), yielding adsorption heights and energies more consistent with the experimental results than standard DFT calculations with generalized gradient approximation (GGA). For anthracene/Ag(111) the effect of the vdW interactions is even more dramatic: we found that "pure" DFT-GGA calculations (without including vdW corrections) result in preference for a tilted configuration, in contrast to the experimental observations of flat-lying adsorption; including vdW corrections, on the other hand, alters the binding geometry of anthracene/Ag(111), favoring the flat configuration. The electronic structure obtained using a self-consistent vdW scheme was found to be nearly indistinguishable from the conventional DFT electronic structure once the correct vdW geometry is employed for these physisorbed systems. Moreover, we show that a vdW correction scheme based on a hybrid functional DFT calculation (HSE) results in an improved description of the highest occupied molecular level of the adsorbed molecules.

  2. Estrogenic status modulates the effect of soy on hepatic responses to 7,12-dimethylbenz(a)anthracene (DMBA)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We examined the influence of estradiol (E2) status and soy protein isolate (SPI) intake on the hepatic responses altered by 7,12-dimethylbenz(a)anthracene (DMBA, a polycyclic aromatic hydrocarbon [PAH]). Sprague–Dawley rats were ovariectomized (OVX) at PND50 and infused with E2 or vehicle for 14 d a...

  3. The role of the van der Waals interactions in the adsorption of anthracene and pentacene on the Ag(111) surface

    NASA Astrophysics Data System (ADS)

    Morbec, Juliana M.; Kratzer, Peter

    2017-01-01

    Using first-principles calculations based on density-functional theory (DFT), we investigated the effects of the van der Waals (vdW) interactions on the structural and electronic properties of anthracene and pentacene adsorbed on the Ag(111) surface. We found that the inclusion of vdW corrections strongly affects the binding of both anthracene/Ag(111) and pentacene/Ag(111), yielding adsorption heights and energies more consistent with the experimental results than standard DFT calculations with generalized gradient approximation (GGA). For anthracene/Ag(111) the effect of the vdW interactions is even more dramatic: we found that "pure" DFT-GGA calculations (without including vdW corrections) result in preference for a tilted configuration, in contrast to the experimental observations of flat-lying adsorption; including vdW corrections, on the other hand, alters the binding geometry of anthracene/Ag(111), favoring the flat configuration. The electronic structure obtained using a self-consistent vdW scheme was found to be nearly indistinguishable from the conventional DFT electronic structure once the correct vdW geometry is employed for these physisorbed systems. Moreover, we show that a vdW correction scheme based on a hybrid functional DFT calculation (HSE) results in an improved description of the highest occupied molecular level of the adsorbed molecules.

  4. Formation and Stabilization of Environmentally Persistent Free Radicals Induced by the Interaction of Anthracene with Fe(III)-Modified Clays.

    PubMed

    Jia, Hanzhong; Nulaji, Gulimire; Gao, Hongwei; Wang, Fu; Zhu, Yunqing; Wang, Chuanyi

    2016-06-21

    Environmentally persistent free radicals (EPFRs) are occasionally detected in Superfund sites but the formation of EPFRs induced by polycyclic aromatic hydrocarbons (PAHs) is not well understood. In the present work, the formation of EPFRs on anthracene-contaminated clay minerals was quantitatively monitored via electron paramagnetic resonance (EPR) spectroscopy, and surface/interface-related environmental influential factors were systematically explored. The obtained results suggest that EPFRs are more readily formed on anthracene-contaminated Fe(III)-montmorillonite than in other tested systems. Depending on the reaction condition, more than one type of organic radicals including anthracene-based radical cations with g-factors of 2.0028-2.0030 and oxygenic carbon-centered radicals featured by g-factors of 2.0032-2.0038 were identified. The formed EPFRs are stabilized by their interaction with interlayer surfaces, and such surface-bound EPFRs exhibit slow decay with 1/e-lifetime of 38.46 days. Transformation pathway and possible mechanism are proposed on the basis of experimental results and quantum mechanical simulations. Overall, the formation of EPFRs involves single-electron-transfer from anthracene to Fe(III) initially, followed by H2O addition on formed aromatic radical cation. Because of their potential exposure in soil and atmosphere, such clay surface-associated EPFRs might induce more serious toxicity than PAHs and exerts significant impacts on human health.

  5. Estrogenic status modulates the effect of soy on hepatic responses to 7,12- dimethylbenz(a)anthracene

    Technology Transfer Automated Retrieval System (TEKTRAN)

    We examined the influence of estradiol (E2) status and soy protein isolate (SPI) intake on the hepatic responses altered by 7,12-dimethylbenz(a)anthracene (DMBA, a polycyclic aromatic hydrocarbon [PAH]). Sprague-Dawley rats were ovariectomized (OVX) at PND50 and infused with E2 or vehicle for 14d an...

  6. Molecular self-healing mechanisms between C60-fullerene and anthracene unveiled by Raman and two-dimensional correlation spectroscopy.

    PubMed

    Geitner, R; Kötteritzsch, J; Siegmann, M; Fritzsch, R; Bocklitz, T W; Hager, M D; Schubert, U S; Gräfe, S; Dietzek, B; Schmitt, M; Popp, J

    2016-07-21

    The self-healing polymer P(LMA-co-MeAMMA) crosslinked with C60-fullerene has been studied by FT-Raman spectroscopy in combination with two-dimensional (2D) correlation analysis and density functional theory calculations. To unveil the molecular changes during the self-healing process mediated by the Diels-Alder equilibrium between 10-methyl-9-anthracenyl groups and C60-fullerene different anthracene-C60-fullerene adducts have been synthesized and characterized by time-, concentration- and temperature-dependent FT-Raman measurements. The self-healing process could be monitored via the C60-fullerene vibrations at 270, 432 and 1469 cm(-1). Furthermore, the detailed analysis of the concentration-dependent FT-Raman spectra point towards the formation of anthracene-C60-fullerene adducts with an unusual high amount of anthracene bound to C60-fullerene in the polymer film, while the 2D correlation analysis of the temperature-dependent Raman spectra suggests a stepwise dissociation of anthracene-C60-fullerene adducts, which are responsible for the self-healing of the polymer.

  7. Coordination Complexes as Catalysts: The Oxidation of Anthracene by Hydrogen Peroxide in the Presence of VO(acac)[subscript 2

    ERIC Educational Resources Information Center

    Charleton, Kimberly D. M.; Prokopchuk, Ernest M.

    2011-01-01

    A laboratory experiment aimed at students who are studying coordination chemistry of transition-metal complexes is described. A simple vanadyl acetylacetonate complex can be used as a catalyst in the hydrogen peroxide oxidation of anthracene to produce anthraquinone. The reaction can be performed under a variety of reaction conditions, ideally by…

  8. ATRAZINE INCREASES DIMETHYLBENZ[A]ANTHRACENE-INDUCED MAMMARY TUMOR INCIDENCE IN LONG EVANS OFFSPRING EXPOSED IN UTERO

    EPA Science Inventory

    ATRAZINE INCREASES DIMETHYLBENZ[A]ANTHRACENE-INDUCED MAMMARY TUMOR INCIDENCE IN LONG EVANS OFFSPRING EXPOSED IN UTERO.

    SE Fenton and CC Davis

    Reproductive Toxicology Division, NHEERL, ORD, USEPA, Durham, NC, USA

    Recently, we found that ATR exposure during ma...

  9. Multiple DNA extractions coupled with stable-isotope probing of anthracene-degrading bacteria in contaminated soil.

    PubMed

    Jones, Maiysha D; Singleton, David R; Sun, Wei; Aitken, Michael D

    2011-05-01

    In many of the DNA-based stable-isotope probing (SIP) studies published to date in which soil communities were investigated, a single DNA extraction was performed on the soil sample, usually using a commercial DNA extraction kit, prior to recovering the (13)C-labeled (heavy) DNA by density-gradient ultracentrifugation. Recent evidence suggests, however, that a single extraction of a soil sample may not lead to representative recovery of DNA from all of the organisms in the sample. To determine whether multiple DNA extractions would affect the DNA yield, the eubacterial 16S rRNA gene copy number, or the identification of anthracene-degrading bacteria, we performed seven successive DNA extractions on the same aliquot of contaminated soil either untreated or enriched with [U-(13)C]anthracene. Multiple extractions were necessary to maximize the DNA yield and 16S rRNA gene copy number from both untreated and anthracene-enriched soil samples. Sequences within the order Sphingomonadales, but unrelated to any previously described genus, dominated the 16S rRNA gene clone libraries derived from (13)C-enriched DNA and were designated "anthracene group 1." Sequences clustering with Variovorax spp., which were also highly represented, and sequences related to the genus Pigmentiphaga were newly associated with anthracene degradation. The bacterial groups collectively identified across all seven extracts were all recovered in the first extract, although quantitative PCR analysis of SIP-identified groups revealed quantitative differences in extraction patterns. These results suggest that performing multiple DNA extractions on soil samples improves the extractable DNA yield and the number of quantifiable eubacterial 16S rRNA gene copies but have little qualitative effect on the identification of the bacterial groups associated with the degradation of a given carbon source by SIP.

  10. Multiple DNA Extractions Coupled with Stable-Isotope Probing of Anthracene-Degrading Bacteria in Contaminated Soil▿†

    PubMed Central

    Jones, Maiysha D.; Singleton, David R.; Sun, Wei; Aitken, Michael D.

    2011-01-01

    In many of the DNA-based stable-isotope probing (SIP) studies published to date in which soil communities were investigated, a single DNA extraction was performed on the soil sample, usually using a commercial DNA extraction kit, prior to recovering the 13C-labeled (heavy) DNA by density-gradient ultracentrifugation. Recent evidence suggests, however, that a single extraction of a soil sample may not lead to representative recovery of DNA from all of the organisms in the sample. To determine whether multiple DNA extractions would affect the DNA yield, the eubacterial 16S rRNA gene copy number, or the identification of anthracene-degrading bacteria, we performed seven successive DNA extractions on the same aliquot of contaminated soil either untreated or enriched with [U-13C]anthracene. Multiple extractions were necessary to maximize the DNA yield and 16S rRNA gene copy number from both untreated and anthracene-enriched soil samples. Sequences within the order Sphingomonadales, but unrelated to any previously described genus, dominated the 16S rRNA gene clone libraries derived from 13C-enriched DNA and were designated “anthracene group 1.” Sequences clustering with Variovorax spp., which were also highly represented, and sequences related to the genus Pigmentiphaga were newly associated with anthracene degradation. The bacterial groups collectively identified across all seven extracts were all recovered in the first extract, although quantitative PCR analysis of SIP-identified groups revealed quantitative differences in extraction patterns. These results suggest that performing multiple DNA extractions on soil samples improves the extractable DNA yield and the number of quantifiable eubacterial 16S rRNA gene copies but have little qualitative effect on the identification of the bacterial groups associated with the degradation of a given carbon source by SIP. PMID:21398486

  11. Azomethine diimides end-capped with anthracene moieties: Experimental and theoretical investigations

    NASA Astrophysics Data System (ADS)

    Schab-Balcerzak, Ewa; Grucela, Marzena; Malecki, Grzegorz; Kotowicz, Sonia; Siwy, Mariola; Janeczek, Henryk; Golba, Sylwia; Praski, Aleksander

    2017-01-01

    New arylene bisimide derivatives containing imine linkages and anthracene units were synthesized. Azomethine diimides were prepared via condensation reaction of 9-anthracenecarboxaldehyde and diamines with phthalic diimide or naphthalene diimide core and Schiff base linkers. They were characterized by FTIR spectroscopy, elemental analysis and mass spectrometry (MALDI-TOF-MS). The synthesized compounds exhibited high resistance against thermal decomposition up to 400 °C. Investigated compounds are electrochemically active and undergo reversible electrochemical reduction and irreversible oxidation processes as was found in cyclic voltammetry studies. The photoluminescence measurements of synthesized compounds in solid state as thin film on glass substrate revealed their ability to emission of the blue light with quantum yield efficiency about 2%. The electronic structure and spectroscopic properties of prepared azomethine diimides were also calculated by the density functional theory (DFT). The electrical properties of the diimide derivatives were preliminary investigated by current-voltage measurements.

  12. Electronic and vibrational spectra of matrix isolated anthracene radical cations - Experimental and theoretical aspects

    NASA Technical Reports Server (NTRS)

    Szczepanski, Jan; Vala, Martin; Talbi, Dahbia; Parisel, Olivier; Ellinger, Yves

    1993-01-01

    The IR vibrational and visible/UV electronic absorption spectra of the anthracene cation, An(+), were studied experimentally, in argon matrices at 12 K, as well as theoretically, using ab initio calculations for the vibrational modes and enhanced semiempirical methods with configuration interaction for the electronic spectra. It was found that both approaches predicted well the observed photoelectron spectrum. The theoretical IR intensities showed some remarkable differences between neutral and ionized species (for example, the CH in-plane bending modes and CC in-plane stretching vibrations were predicted to increase by several orders of magnitude upon ionization). Likewise, estimated experimental IR intensities showed a significant increase in the cation band intensities over the neutrals. The implication of these findings for the hypothesis that polycyclic aromatic hydrocarbon cations are responsible for the unidentified IR emission bands from interstellar space is discussed.

  13. Polymorphism in Self-Assembled Structures of 9-Anthracene Carboxylic Acid on Ag(111)

    PubMed Central

    Lu, Chao; Wei, Yinying; Zhu, Erkuang; Reutt-Robey, Janice E.; Xu, Bo

    2012-01-01

    Surface self-assembly process of 9-anthracene carboxylic acid (AnCA) on Ag(111) was investigated using STM. Depending on the molecular surface density, four spontaneously formed and one annealed AnCA ordered phases were observed, namely a straight belt phase, a zigzag double-belt phase, two simpler dimer phases, and a kagome phase. The two high-density belt phases possess large unit cells on the scale length of 10 nm, which are seldom observed in molecular self-assembled structures. This structural diversity stems from a complicated competition of different interactions of AnCA molecules on metal surface, including intermolecular and molecular-substrate interactions, as well as the steric demand from high molecular surface density. PMID:22837666

  14. Growth of large naphthalene and anthracene single-crystal sheets at the liquid–air interface

    SciTech Connect

    Postnikov, V. A.; Chertopalov, S. V.

    2015-07-15

    The growth of organic single crystals of naphthalene (C{sub 10}H{sub 8}) and anthracene (C{sub 14}H{sub 10}) at the liquid‒air interface from a mixture of solvents has been investigated. The growth technique used in the study makes it possible to obtain single-crystal sheets up to 10 mm in size for 24 h. The surface morphology and structure of the crystals have been analyzed by optical microscopy and X-ray diffraction. C{sub 10}H{sub 8} and C{sub 14}H{sub 10} single crystals grow coplanarly along the (001) plane. A thermodynamic model of the flat-crystal nucleus formation at the liquid‒air interface, based on the analysis of the change in the free Gibbs energy, is considered.

  15. Reaction of anthracene with atomic ions of interstellar interest. A FALP measurement at room temperature

    NASA Astrophysics Data System (ADS)

    Canosa, A.; Laubé, S.; Rebrion, C.; Pasquerault, D.; Gomet, J. C.; Rowe, B. R.

    1995-11-01

    We present the results obtained on studying the reaction of anthracene with some atomic ions of interstellar interest (He + and C +) and with Ar +. Rate coefficients have been measured at room temperature (293 K) in afterglow experiments using flowing afterglow Langmuir probe-mass spectrometer apparatus. Reactions proceed with rate coefficients of respectively 5.2 × 10 -9, 3 × 10 -9, 1 × 10 -9 cm 3 s -1 for He +, C + and Ar +. The results were obtained with an uncertainty of about 30% and were found to be close to the Langevin rate. The nature of the products has also been investigated. More particularly, the evidence for carbon accretion and for the production of doubly charged species is discussed.

  16. Intramolecular Charge-Transfer Interaction of Donor-Acceptor-Donor Arrays Based on Anthracene Bisimide.

    PubMed

    Iwanaga, Tetsuo; Ogawa, Marina; Yamauchi, Tomokazu; Toyota, Shinji

    2016-05-20

    We designed anthracene bisimide (ABI) derivatives having two triphenylamine (TPA) groups as donor units at the 9,10-positions to form a novel π-conjugated donor-acceptor system. These compounds and their analogues with ethynylene linkers were synthesized by Suzuki-Miyaura and Sonogashira coupling reactions, respectively. In UV-vis spectra, the linker-free derivatives showed broad absorption bands arising from intramolecular charge-transfer interactions. Introducing ethynylene linkers resulted in a considerable red shift of the absorption bands. In fluorescence spectra, the ethynylene derivatives showed intense emission bands at 600-650 nm. Their photophysical and electrochemical properties were compared with those of the corresponding mono TPA derivatives on the basis of theoretical calculations and cyclic voltammetry to evaluate the intramolecular electronic interactions between the donor and acceptor units.

  17. Post-shock chemical and ESR analysis of acrylamide and selected anthracene derivatives. [9-cyanoanthracene

    SciTech Connect

    Dodson, B.W.; Arnold, C. Jr.; Venturini, E.L.; Lenahan, P.M.

    1983-01-01

    We report on a series of impact recovery experiments performed on organic samples. Acrylamide was loaded to peak stresses of 4.8 and 6.7 GPa in a copper capsule using an air-driven projectile. No polyacrylamide was formed in these impact experiments. ESR studies reveal approx. 1 ppM free radicals, which are stable in the acrylamide lattice. Upon solution in tetrahydrofuran (THF), these radicals become mobile, resulting in polymer formation, a reaction not seen in unshocked acrylamide and 9-cyanoanthracene (9-CA) in the stress range 1.8 to 4.0 GPa. The residual radical density in the 9-CA was roughly 10 times that in the anthracene. A systematic relation between peak stress and formation of specific radicals were observed. 3 figures.

  18. Monolayer anthracene and anthraquinone modified electrodes as platforms for Trametes hirsuta laccase immobilisation.

    PubMed

    Sosna, Maciej; Chrétien, Jean-Mathieu; Kilburn, Jeremy D; Bartlett, Philip N

    2010-09-14

    Surface modification techniques are essential to the construction of enzyme based elements of biofuel cells and biosensors. In this article we report on the preparation and characterisation of modified carbon electrodes which were used as supports for the immobilisation of laccase from Trametes hirsuta. The electrodes were electrochemically modified with diamine or diazonium linkers followed by attachment of either anthracene or anthraquinone head groups using solid phase chemical methodology. These well defined surfaces were found to effectively bind laccase and to provide direct electrical contact to the enzyme active site, as evidenced by XPS, EIS and voltammetry, respectively. The influence of the type of linker and head group on enzyme binding and bioelectrocatalytic activity are evaluated.

  19. NAH plasmid-mediated catabolism of anthracene and phenanthrene to naphthoic acids.

    PubMed Central

    Menn, F M; Applegate, B M; Sayler, G S

    1993-01-01

    Pseudomonas fluorescens 5R contains an NAH7-like plasmid (pKA1), and P. fluorescens 5R mutant 5RL contains a bioluminescent reporter plasmid (pUTK21) which was constructed by transposon mutagenesis. Polymerase chain reaction mapping confirmed the localization of lux transposon Tn4431 300 bp downstream from the start of the nahG gene. Two degradation products, 2-hydroxy-3-naphthoic acid and 1-hydroxy-2-naphthoic acid, were recovered and identified from P. fluorescens 5RL as biochemical metabolites from the biotransformation of anthracene and phenanthrene, respectively. This is the first report which provides direct biochemical evidence that the naphthalene plasmid degradative enzyme system is involved in the degradation of higher-molecular-weight polycyclic aromatic hydrocarbons other than naphthalene. Images PMID:8328810

  20. Ionization of 4,4'-bis(phenylethynyl) anthracene by electron impact.

    PubMed

    Kukhta, A V; Kukhta, I N; Zavilopulo, A N; Agafonova, A S; Shpenik, O B

    2009-01-01

    Ionization of a 4,4'-bis(phenylethynyl)anthracene (C(30)H(18), BPEA) molecule is studied for the first time at different energies of bombarding electrons in crossed electron and molecular beams. The relative cross-section of single ionization of a BPEA molecule in the energy range of 5-55 eV is measured. The ionization potential, E(I) = 7.62 +/- 0.2 eV, is determined using the threshold region of C(30)H(18)(+) ion yield energy dependence. A scheme of the BPEA molecule fragmentation is proposed. Experimental results are in reasonable accordance with calculations made in the framework of the density functional theory.

  1. Direct, Electrocatalytic Oxygen Reduction by Laccase on Anthracene-2-methanethiol Modified Gold.

    PubMed

    Thorum, Matthew S; Anderson, Cyrus A; Hatch, Jeremy J; Campbell, Andrew S; Marshall, Nicholas M; Zimmerman, Steven C; Lu, Yi; Gewirth, Andrew A

    2010-08-01

    Laccase, a multicopper oxidase, catalyses the four electron reduction of oxygen to water. Upon adsorption to an electrode surface, laccase is known to reduce oxygen at overpotentials lower than the best noble metal electrocatalysts usually employed. While the electrocatalytic activity of laccase is well established on carbon electrodes, laccase does not typically adsorb to better defined noble metal surfaces in an orientation that allows for efficient electrocatalysis. In this work, we utilized anthracene-2-methanethiol (AMT) to modify the surface of Au electrodes and examined the electrocatalytic activity of adsorbed laccase. AMT facilitated the adsorption of laccase, and the onset of electrocatalytic oxygen reduction was observed as high as 1.13 V(RHE). We observed linear Tafel behavior with a 144 mV/dec slope, consistent with an outer sphere single electron transfer from the electrode to a Cu site in the enzyme as the rate determining step of the oxygen reduction mechanism.

  2. Anthracene-terpyridine metal complexes as new G-quadruplex DNA binders.

    PubMed

    Gama, Sofia; Rodrigues, Inês; Mendes, Filipa; Santos, Isabel C; Gabano, Elisabetta; Klejevskaja, Beata; Gonzalez-Garcia, Jorge; Ravera, Mauro; Vilar, Ramon; Paulo, António

    2016-07-01

    The formation of quadruple-stranded DNA induced by planar metal complexes has particular interest in the development of novel anticancer drugs. This is especially relevant for the inhibition of telomerase, which plays an essential role in cancer cell immortalization and is overexpressed in ca. 85-90% of cancer cells. Moreover, G-quadruplexes also exist in other locations in the human genome, namely oncogene promoter regions, and it has been hypothesized that they play a regulatory role in gene transcription. Herein we report a series of new anthracene-containing terpyridine ligands and the corresponding Cu(II) and Pt(II) complexes, with different linkers between the anthracenyl moiety and the terpyridine chelating unit. The interaction of these ligands and metal complexes with different topologies of DNA was studied by several biophysical techniques. The Pt(II) and Cu(II) complexes tested showed affinity for quadruplex-forming sequences with a good selectivity over duplex DNA. Importantly, the free ligands do not have significant affinity for any of the DNA sequences used, which shows that the presence of the metal is essential for high affinity (and selectivity). This effect is more evident in the case of the Pt(II) complexes. Moreover, the presence of a longer linker between the chelating terpyridine unit and the anthracene moiety enhances the interaction with G-quadruplex-forming sequences. We further evaluated the ability of the Cu(II) complexes to interact with, and stabilize G-quadruplex containing regions in oncogene promoters via a polymerase stop assay. These studies indicated that the metal complexes are able to induce G-quadruplex formation and stop polymerase activity.

  3. Raman and surface enhanced Raman scattering study of the orientation of cruciform 9,10-anthracene thiophene and furan derivatives deposited on a gold colloidal surface

    NASA Astrophysics Data System (ADS)

    Muñoz-Pérez, J.; Leyton, P.; Paipa, C.; Soto, J. P.; Brunet, J.; Gómez-Jeria, J. S.; Campos-Vallette, M. M.

    2016-10-01

    The 9,10-di(thiophen-2-yl)anthracene (TAT), 9,10-di(furan-2-yl)anthracene (FAF) and 2-[(10-(thiophen-2-yl)anthracen-9-yl)]furan (TAF) cruciform molecular systems were synthesized using one-step coupling reactions and structurally characterized via Raman, infrared, 1H NMR, 13C NMR and mass spectroscopies. The orientation of the analytes on a gold colloidal surface was inferred from a surface-enhanced Raman scattering (SERS) study. The metal surface interaction was driven by the S and O atoms of the thiophene and furan α-substituents, and the plane of the anthracene fragment remained parallel to the surface. Theoretical calculations based on a simplified molecular model for the analyte-surface interaction provide a good representation of the experimental data.

  4. Design of Poly(L-lactide)-Poly(ethylene glycol) Copolymer with Light-Induced Shape-Memory Effect Triggered by Pendant Anthracene Groups.

    PubMed

    Xie, Hui; He, Man-jie; Deng, Xiao-Ying; Du, Lan; Fan, Cheng-Jie; Yang, Ke-Ke; Wang, Yu-Zhong

    2016-04-13

    A novel light-induced shape-memory material based on poly(l-lactide)-poly(ethylene glycol) copolymer is developed successfully by dangling the photoresponsive anthracene group on the PEG soft segment selectively. For synthesis strategy, the preprepared photoresponsive monomer N,N-bis(2-hydroxyethyl)-9-anthracene-methanamine (BHEAA) is first embedded into PEG chains; then, we couple this anthracene-functionalized PEG precursor with PLA precursor to result in PLA-PEG-A copolymer. The composition of target product can be well-defined by simply adjusting the feed ratio. The chemical structures of intermediate and final products are confirmed by (1)H NMR. Differential scanning calorimetry analysis of material reveals that the PEG soft segment became noncrystallizable when 4% or more BHEAA is introduced, and this feature is beneficial to the mobility of anthracene groups in polymer matrix. The static tensile tests show that the samples exhibit rubberlike mechanical properties except for the PLA-dominant one. The reversibility of [4 + 4] cycloaddition reaction between pendant anthracene groups in PLA-PEG-A film is demonstrated by UV-vis. Eventually, the light-induced shape-memory effect (LSME) is successfully realized in PLA-PEG-A. The results of cyclic photomechanical tests also reveal that the content of PLA hard segment as well as photosensitive anthracene moieties plays a crucial role in LSME.

  5. Anthraphane: An Anthracene-Based, Propeller-Shaped D(3h)-Symmetric Hydrocarbon Cyclophane and Its Layered Single Crystal Structures.

    PubMed

    Servalli, Marco; Trapp, Nils; Wörle, Michael; Klärner, Frank-Gerrit

    2016-03-18

    The novel hydrocarbon propeller-shaped D3h-symmetric cyclophane (3), "anthraphane", was prepared through a revisited and optimized gram-scale synthesis of the key building block anthracene-1,8-ditriflate 7. Anthraphane has a high tendency to crystallize and single crystals in size ranges of 100-200 μm are easily obtained from different solvents. The crystallization behavior of 3 was extensively studied to unravel packing motifs and determine whether the packing can be steered into a desired direction, so to allow topochemical photopolymerization. SC-XRD shows that anthraphane packs in layers irrespective of the solvent used for crystallization. However, within the layers, intermolecular arrangements and π-π interactions of the anthracene units vary strongly. Four interaction motifs for the anthracene moieties are observed and discussed in detail: two types of exclusively edge-to-face (etf), a mixture of edge-to-face and face-to-face (ftf), and no anthracene-anthracene interaction at all. To elucidate why an exclusive ftf stacking was not observed, electrostatic potential surface (EPS) calculations with the semiempirical PM3 method were performed. They show qualitatively that the anthracene faces bear a strong negative surface potential, which may be the cause for this cyclophane to avoid ftf interactions. This combined crystallographic and computational study provides valuable insights on how to create all-ftf packings.

  6. Structure-property relationships: asymmetric alkylphenyl-substituted anthracene molecules for use in small-molecule solar cells.

    PubMed

    Kim, Yu Jin; Ahn, Eun Soo; Jang, Sang Hun; An, Tae Kyu; Kwon, Soon-Ki; Chung, Dae Sung; Kim, Yun-Hi; Park, Chan Eon

    2015-05-11

    Two asymmetric anthracene-based organic molecules, NDHPEA and TNDHPEA, were prepared without or with a thiophene spacer between the anthracene and naphthalene units. These asymmetric oligomers displayed different degrees of coplanarity, as evidenced by differences in the dihedral angles calculated by using DFT. Differential scanning calorimetry and XRD studies were used to probe the crystallization characteristics and molecular packing structures in the active layers. The coplanarity of the molecules in the asymmetric structure significantly affected the crystallization behavior and the formation of crystalline domains in the solid state. The small-molecule crystalline properties were correlated with the device physics by determining the J-V characteristics and hole mobilities of the devices.

  7. Catalytic synthesis of high-value chemicals from coal-derived liquids. Conversion of phenanthrene derivatives into anthracene derivatives

    SciTech Connect

    Song, C.; Lai, W.C.

    1998-12-31

    It is known that phenanthrene and its derivatives are abundant in coal-derived liquids from coal carbonization, pyrolysis, and liquefaction; however, they have found little use in industry. On the other hand, anthracene and its derivatives are more useful materials for industrial applications. Thus, it is highly desirable to convert phenanthrene derivatives to anthracene derivatives. The authors have found that some chemically modified mordenites and Y-zeolites can selectively promote the transformation of sym-octahydrophenanthrene (sym-OHP) into sym-octahydroanthracene (sym-OHA) at lower temperatures. In this work, the effects of zeolite catalysts and reaction conditions on the ring-shift isomerization of sym-OHP into sym-OHA were studied through experiments at 200--300 C under an initial pressure of 0.79 MPa N{sub 2} or H{sub 2}. They also explored the simultaneous hydrogenation-ring-shift isomerization of phenanthrene using zeolite-supported metal catalysts.

  8. Pathway-Dependent Post-assembly Modification of an Anthracene-Edged M(II)4L6 Tetrahedron.

    PubMed

    Ronson, Tanya K; Pilgrim, Ben S; Nitschke, Jonathan R

    2016-08-24

    Fe(II)4L6 tetrahedral cage 1 undergoes post-assembly modification (PAM) via a Diels-Alder cycloaddition of the anthracene panels of the cage with tetracyanoethylene (TCNE). The modified cage 2 possesses an enclosed cavity suitable for encapsulation of the fullerene C60, whereas original cage 1 forms a unique covalent adduct through a Diels-Alder cycloaddition of three of its anthracene ligands with C60. This adduct undergoes further PAM via reaction of the remaining three ligands with TCNE, enabling the isolation of two distinct products depending on the order of addition of C60 and TCNE. Modified cage 2 was also able to bind an anionic guest, [Co(C2B9H11)2](-), which was not encapsulated by the original cage, demonstrating the potential of PAM for tuning the binding properties of supramolecular hosts.

  9. New diagnostic ratios based on phenanthrenes and anthracenes for effective distinguishing heavy fuel oils from crude oils.

    PubMed

    Zhang, Haijiang; Wang, Chuanyuan; Zhao, Ruxiang; Yin, Xiaonan; Zhou, Hongyang; Tan, Liju; Wang, Jiangtao

    2016-05-15

    The heavy fuel oils (HFOs) and crude oils are the main oil types in the marine oil spill accidents in China. It is usually a challenge to distinguish the HFOs from crude oils due to the highly similar physicochemical characteristics. In this paper, the distributions of phenanthrene (Phe), anthracene (Ant), methyl-phenanthrene (MP) and methyl-anthracene (MA) in hundreds of HFOs and crude oils samples which were collected from all over the world were characterized. Nine new diagnostic indexes, such as Ant/(Ant+Phe) and other eight diagnostic ratios based on the MP isomers and MA, were developed for effective distinguishing HFOs from crude oils. The histogram with normal fit plots, the double ratio plots and Bayes discriminant analysis (BDA) method were employed to illustrate the effectiveness of the new diagnostic indexes. BDA model based on nine new diagnostic indexes demonstrated high precision with discriminant ratio which lay between 93.92% and 99.32%.

  10. A Star-shaped Oligo(phenylenevinylene) Liquid Crystal Host with an Anthracene Guest-A Double Nanosegregating Supermesogen.

    PubMed

    Maier, Philipp; Grüne, Matthias; Lehmann, Matthias

    2017-01-23

    Hexasubstituted C3 -symmetric benzenes with three elongated shape-persistent oligo(phenylenevinylene) arms and three pyridyl hydrogen-bond acceptors have been synthesized. These mesogens assemble in a double-helical columnar liquid crystal (LC) structure, owing to the compensation of free spaces between conjugated arms by dimer formation. The void is filled also by up to three anthracene carboxylic acids as guests forming hydrogen bonded supermesogens assembling in columnar LC and soft-crystal phases. Thin film fluorescence and solid-state NMR spectroscopy imply a transition from a disordered columnar LC to an unexpected double nanosegregated morphology of a filled soft columnar crystal phase. An additional intracolumnar separation of anthracene and oligo(phenylenevinylene) chromophores occurs, separate to the general segregation of aliphatic and aromatic building blocks in LC structures. The new type of supermesogens will enable the rational design of host-guest double cables with a wide range of different conjugated building blocks.

  11. Novel blue emitters based on anthracene derivatives with naphthalene and phenylquinoline moieties for organic light-emtting diodes

    NASA Astrophysics Data System (ADS)

    Park, Soo Na; Bee Lee, Seul; Kim, Chanwoo; Lee, Ho Won; Kim, Young Kwan; Yoon, Seung Soo

    2015-06-01

    In this study, we have designed three blue emitters based on anthracene derivatives with electron withdrawing phenylquinoline moieties. To explore the electroluminescence properties of these materials as blue materials, multilayer blue organic light-emtting diodes (OLEDs) were fabricated in the following device structure: indium-tin-oxide (ITO)/4,4‧-bis[N-(1-naphthyl)-N-phenylamino]biphenyl (NPB)/blue emitters (30 nm) bathophenanthroline (Bphen) (35 nm)/lithium quinolate (Liq) (2 nm)/Al. Among those, a device using 4-{4-[10-(naphthalen-2-yl)anthracen-9-yl]phenyl}-2-phenylquinoline exhibited efficient blue emission with a luminous and power efficiency of 1.59 cd/A and 0.89 lm/W at 20 mA/cm2, respectively. The commission internationale de l’éclairage (CIE) coordinates of this device were (x = 0.17, y = 0.21) at 7.5 V.

  12. Unusual transformation of the diarylmethanol derivative into an unknown 1,2,3,6,7,10-hexahydroxylated anthracene system.

    PubMed

    Bałczewski, Piotr; Koprowski, Marek; Bodzioch, Agnieszka; Marciniak, Bernard; Rózycka-Sokołowska, Ewa

    2006-03-31

    10-Benzyloxy-1,2,3-trimethoxy-6,7-(methylene-1,3-dioxy)anthracene as a potential material for molecular electronics was synthesized from the O-benzyl-protected diarylmethanol derivative containing the 1,3-dioxyethylene acetal function via a one-pot procedure under acidic conditions (1 N HCl, methanol, 60 h) in 60% yield. The replacement of methanol for benzene resulted in hydrolysis of the acetal function in 96% yield.

  13. Anthracene based compounds as new L-type Ca2+ channel blockers: design, synthesis, and full biological profile.

    PubMed

    Bova, Sergio; Saponara, Simona; Rampa, Angela; Gobbi, Silvia; Cima, Lorenzo; Fusi, Fabio; Sgaragli, Giampietro; Cavalli, Maurizio; de los Rios, Cristobal; Striessnig, Jörg; Bisi, Alessandra

    2009-03-12

    L-Type Ca(2+) channels (LTCCs) play a key role in the regulation of vascular smooth muscle contraction, and substances that interfere with their function (Ca(2+) channel blockers) are widely used in the therapy of hypertension. Here, we report anthracene-maleimide derivatives as new LTCC blockers. Among these, 3, lacking intracellular effects, was investigated in more detail. The results show that 3 binds preferentially to inactivated LTCCs, directly interacting with the pore-forming subunit of the channel.

  14. Crystal structure of [(1,2,3,4,11,12-η)-anthracene]tris-(tri-methyl-stann-yl)cobalt(III).

    PubMed

    Brennessel, William W; Ellis, John E

    2014-11-01

    The asymmetric unit of the title structure, [Co(η(6)-C14H10){Sn(CH3)3}3], contains two independent mol-ecules. Each anthracene ligand is η(6)-coordinating to a Co(III) cation and is nearly planar [fold angles of 5.4 (3) and 9.7 (3)°], as would be expected for its behaving almost entirely as a donor to a high-oxidation-state metal center. The slight fold in each anthracene ligand gives rise to slightly longer Co-C bond lengths to the ring junction carbon atoms than to the other four. Each Co(III) cation is further coordinated by three Sn(CH3)3 ligands, giving each mol-ecule a three-legged piano-stool geometry. In each of the two independent mol-ecules, the trio of SnMe3 ligands are modeled as disordered over two positions, rotated by approximately 30%, such that the C atoms nearly overlap. In one mol-ecule, the disorder ratio refined to 0.9365 (8):0.0635 (8), while that for the other refined to 0.9686 (8):0.0314 (8). The mol-ecules are well separated, and thus no significant inter-molecular inter-actions are observed. The compound is of inter-est as the first structure report of an η(6)-anthracene cobalt(III) complex.

  15. Changes of benthic bacteria and meiofauna assemblages during bio-treatments of anthracene-contaminated sediments from Bizerta lagoon (Tunisia).

    PubMed

    Ben Said, Olfa; Louati, Hela; Soltani, Amel; Preud'homme, Hugues; Cravo-Laureau, Cristiana; Got, Patrice; Pringault, Olivier; Aissa, Patricia; Duran, Robert

    2015-10-01

    Sediments from Bizerta lagoon were used in an experimental microcosm setup involving three scenarios for the bioremediation of anthracene-polluted sediments, namely bioaugmentation, biostimulation, and a combination of both bioaugmentation and biostimulation. In order to investigate the effect of the biotreatments on the benthic biosphere, 16S rRNA gene-based T-RFLP bacterial community structure and the abundance and diversity of the meiofauna were determined throughout the experiment period. Addition of fresh anthracene drastically reduced the benthic bacterial and meiofaunal abundances. The treatment combining biostimulation and bioaugmentation was most efficient in eliminating anthracene, resulting in a less toxic sedimentary environment, which restored meiofaunal abundance and diversity. Furthermore, canonical correspondence analysis showed that the biostimulation treatment promoted a bacterial community favorable to the development of nematodes while the treatment combining biostimulation and bioaugmentation resulted in a bacterial community that advantaged the development of the other meiofauna taxa (copepods, oligochaetes, polychaetes, and other) restoring thus the meiofaunal structure. The results highlight the importance to take into account the bacteria/meiofauna interactions during the implementation of bioremediation treatment.

  16. Vibrational properties of organic donor-acceptor molecular crystals: Anthracene-pyromellitic-dianhydride (PMDA) as a case study.

    PubMed

    Fonari, A; Corbin, N S; Vermeulen, D; Goetz, K P; Jurchescu, O D; McNeil, L E; Bredas, J L; Coropceanu, V

    2015-12-14

    We establish a reliable quantum-mechanical approach to evaluate the vibrational properties of donor-acceptor molecular crystals. The anthracene-PMDA (PMDA = pyromellitic dianhydride) crystal, where anthracene acts as the electron donor and PMDA as the electron acceptor, is taken as a representative system for which experimental non-resonance Raman spectra are also reported. We first investigate the impact that the amount of nonlocal Hartree-Fock exchange (HFE) included in a hybrid density functional has on the geometry, normal vibrational modes, electronic coupling, and electron-vibrational (phonon) couplings. The comparison between experimental and theoretical Raman spectra indicates that the results based on the αPBE functional with 25%-35% HFE are in better agreement with the experimental results compared to those obtained with the pure PBE functional. Then, taking αPBE with 25% HFE, we assign the vibrational modes and examine their contributions to the relaxation energy related to the nonlocal electron-vibration interactions. The results show that the largest contribution (about 90%) is due to electron interactions with low-frequency vibrational modes. The relaxation energy in anthracene-PMDA is found to be about five times smaller than the electronic coupling.

  17. Vibrational properties of organic donor-acceptor molecular crystals: Anthracene-pyromellitic-dianhydride (PMDA) as a case study

    SciTech Connect

    Fonari, A.; Corbin, N. S.; Coropceanu, V. E-mail: coropceanu@gatech.edu; Vermeulen, D.; McNeil, L. E.; Goetz, K. P.; Jurchescu, O. D.; Bredas, J. L. E-mail: coropceanu@gatech.edu

    2015-12-14

    We establish a reliable quantum-mechanical approach to evaluate the vibrational properties of donor-acceptor molecular crystals. The anthracene-PMDA (PMDA = pyromellitic dianhydride) crystal, where anthracene acts as the electron donor and PMDA as the electron acceptor, is taken as a representative system for which experimental non-resonance Raman spectra are also reported. We first investigate the impact that the amount of nonlocal Hartree-Fock exchange (HFE) included in a hybrid density functional has on the geometry, normal vibrational modes, electronic coupling, and electron-vibrational (phonon) couplings. The comparison between experimental and theoretical Raman spectra indicates that the results based on the αPBE functional with 25%-35% HFE are in better agreement with the experimental results compared to those obtained with the pure PBE functional. Then, taking αPBE with 25% HFE, we assign the vibrational modes and examine their contributions to the relaxation energy related to the nonlocal electron-vibration interactions. The results show that the largest contribution (about 90%) is due to electron interactions with low-frequency vibrational modes. The relaxation energy in anthracene-PMDA is found to be about five times smaller than the electronic coupling.

  18. 4,4′-(Anthracene-9,10-di­yl)dibenzoic acid dimethyl­formamide disolvate

    PubMed Central

    Li, Hong; Wang, Zhi-Qiang; Yang, Liu-Zhi; Liu, Yan-Qi; Mao, Duo-Bin

    2009-01-01

    In the title compound, C28H18O4·2C3H7NO, the dihedral angle between the benzene rings and the anthracene system is 74.05 (12)°. A crystallographic inversion centre is located in the middle of the anthracene unit. The dimethyl­formamide solvent mol­ecules are partially disordered over two positions of approximately equal occupancy [0.529 (6):0.471 (6)]. Inter­molecular O—H⋯O hydrogen bonds with the major occupancy formamide O atom as acceptor result in the formation of 2:1 solvate–complex aggregates, which are alternately linked to shorter solvate units via weak inter­molecular C—H⋯O contacts generated from the rotational disorder of the formamide O atom (minor occupancy component). Weak C—H⋯π inter­actions between the solvent mol­ecules as the donor and the outer anthracene rings support these contacts in the crystal structure for both disorder components. PMID:21583091

  19. Enhanced bioremediation of anthracene contaminated soil by bioaugmentation and application of non-ionic surfactant -- Fuelbuster{reg_sign}

    SciTech Connect

    Pattanayek, M.; Cobb, G.P.

    1995-12-31

    Surfactants enable the mass transfer of hydrophobic compounds to more hydrophilic phases, thereby increasing bioavailability to microorganisms for degradation. Indigenous soil bacteria was enriched over three months to selectively degrade anthracene. Enhanced soil remediation was determined using radiolabeled anthracene and comparing the end product 14-CO{sub 2} from different treatment and control groups. Bioreactors were engineered, fitted with inflow of air and CO{sub 2} trapping devices. The two treatment groups included were, (1) sterile soil seeded with enriched microorganisms and (2) sterile soil seeded with microorganisms and Fuelbuster{reg_sign} at concentrations below its critical micellar concentrations (determined by surface tension method). The control group had only sterile soil to account for any abiotic degradation. Remediation was monitored over 91 days and the end product was analyzed by liquid scintillation counting. On day 50 of remediation the relative CO{sub 2} evolution was 0.086 : 0.22 : 0.69 for control: Treatment 1: Treatment 2. On day 50 additional Fuelbuster{reg_sign} was injected into Treatment 2, which resulted in a 30% increase in CO{sub 2} evolution when the study was terminated. Binding effect of soil on the bioavailability of anthracene is currently being studied using the same experimental setup, excluding soil from all treatment groups.

  20. High-efficiency and long-lifetime fluorescent blue organic-emitting device

    NASA Astrophysics Data System (ADS)

    Ho, Yu-Hsuan; Lin, Tien-Chun; Wu, Chia-Fang; Lee, Jiun-Haw

    2006-08-01

    In this paper, We have demonstrated a blue fluorescent organic light-emitting device (OLED) with a current efficiency of 19.2 cd/A at 100 cd/m2, an estimated half-lifetime of 15611 hours at an initial luminance of 1000 cd/m2, and a voltage of 4.9 V at 20 mA/cm2 with a high electron mobility electron transport layer (ETL) material and high efficiency dopant material. The external quantum efficiency (EQE) in this optimized OLED is 8.32%, which is very close to the theoretical limit. Carrier balance condition is achieved due to the incorporation of the high mobility ETL, bis(10- hydroxyben-zo[h]quinolinato)beryllium (Bebq2), which can not only effectively increase the current efficiency and elongate the operation lifetime, but also reduce the driving voltage and increase the power efficiency. The EML consisted of 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) as the blue dopant and 9,10-bis(2'- naphthyl) anthracene (ADN) as the matrix. We found that the dopant concentration of DPAVBi did not affect the mobility value of the EML which is consistent with the J-V characteristics. Besides, although it is believed the bulk ADN is a kind of HTL materials, we found the electron mobility of ADN is one order of magnitude higher than its hole mobility in our blue OLEDs.

  1. High-efficient and brightness white organic light-emitting diodes operated at low bias voltage

    NASA Astrophysics Data System (ADS)

    Zhang, Lei; Yu, Junsheng; Yuan, Kai; Jian, Yadong

    2010-10-01

    White organic light-emitting diodes (OLEDs) used for display application and lighting need to possess high efficiency, high brightness, and low driving voltage. In this work, white OLEDs consisted of ambipolar 9,10-bis 2-naphthyl anthracene (ADN) as a host of blue light-emitting layer (EML) doped with tetrabutyleperlene (TBPe) and a thin codoped layer consisted of N, N'-bis(naphthalen-1-yl)-N,N'-bis(phenyl)-benzidine (NPB) as a host of yellow light-emitting layer doped with 4-(dicyanomethylene)-2-tert-butyl-6-(1,1,7,7-tetramethyljulolidin-4-yl-vinyl)-4H-pyran (DCJTB) were investigated. With appropriate tuning in the film thickness, position, and dopant concentration of the co-doped layer, a white OLED with a luminance yield of 10.02 cd/A with the CIE coordinates of (0.29, 0.33) has been achieved at a bias voltage of 9 V and a luminance level of over 10,000 cd/m2. By introducing the PIN structure with both HIL and bis(10- hydroxybenzo-quinolinato)-beryllium (BeBq2) ETL, the power efficiency of white OLED was improved.

  2. Highly efficient blue organic light-emitting diodes using dual emissive layers with host-dopant system

    NASA Astrophysics Data System (ADS)

    Lee, Bo Mi; Yu, Hyeong Hwa; Kim, You Hyun; Kim, Nam Ho; Yoon, Ju An; Mascher, Peter; Kim, Woo Young

    2012-10-01

    In this study, we fabricated highly efficient blue organic light-emitting diodes by designing different emitting layer structures with fluorescent host and dopant materials of 4,4-bis(2,2-diphenylyinyl)-1,10-biphenyl (DPVBi) and 9,10- bis(2-naphthyl) anthracene (ADN) as host materials and 4,4'-bis(9-ethyl-3-carbazovinylene)-1,1'biphenyl (BCzVBi) as a dopant material to demonstrate electrical and optical improvements. Best enhancement in luminance and luminous efficiency were achieved by a quantum well structure and energy transfer between host and dopant materials in device F as of 8668cd/m2 at 8V and 5.16 Cd/A at 103.20 mA/cm2 respectively. Among the blue OLED devices doped by BCzVBi, device B emits the deepest blue emission with Commission Internationale de l'É clairage (CIExy) coordinates of (0.157, 0.117) at 8V.

  3. Exciplex-Sensitized Triplet-Triplet Annihilation in Heterojunction Organic Thin-Film.

    PubMed

    Lin, Bo-Yen; Easley, Connor J; Chen, Chia-Hsun; Tseng, Po-Chen; Lee, Ming-Zer; Sher, Pin-Hao; Wang, Juen-Kai; Chiu, Tien-Lung; Lin, Chi-Feng; Bardeen, Christopher J; Lee, Jiun-Haw

    2017-03-29

    A new concept for organic light-emitting diodes (OLEDs) is presented, which is called exciplex-sensitized triplet-triplet annihilation (ESTTA). The exciplex formed at the organic heterojunction interface of 4,4',4″-tris(N-3-methyphenyl-N-phenyl-amino) triphenylamine and 9,10-bis(2'-naphthyl) anthracene (ADN) is used to sensitize the triplet-triplet annihilation (TTA) process on the ADN molecules. This results in a turn-on voltage (2.2 V) of the blue emission from the OLED below the bandgap (2.9 eV). From the transient electroluminescence measurement, blue emission totally came from the TTA process without direct recombination on the ADN molecules. The blue singlet exciton from the TTA process can be quenched by energy transfer to the exciplex, as revealed by transient photoluminescence measurements. This can be prevented by blocking the energy transfer path and improving the radiative recombination rate of blue emission. With the insertion of the "triplet diffusion and singlet blocking (TDSB)" layer and the incorporation of the dopant material, an ESTTA-OLED with external quantum efficiency of 5.1% was achieved, which consists of yellow and blue emission coming from the exciplex and ESTTA process, respectively.

  4. Encapsulation of biogenic and synthetic polyamines by nanoparticles PEG and mPEG-anthracene.

    PubMed

    Sanyakamdhorn, S; Chanphai, P; Tajmir-Riahi, H A

    2014-01-05

    Synthetic polymers play a major role in drug delivery in vitro and in vivo. We report the bindings of biogenic polyamines, spermine (spm), and spermidine (spmd), and their synthetic analogues, 3,7,11,15-tetrazaheptadecane⋅4HCl (BE-333) and 3,7,11,15,19-pentazahenicosane⋅5HCl (BE-3333) with poly(ethylene glycol) PEG-3000, PEG-8000 and methoxy poly(ethylene glycol) anthracene (PEG-anthracene). Fourier transform infrared (FTIR), UV-visible and fluorescence spectroscopic were used to analyze polyamine binding mode, the binding constant and the effect of PEG compositions on polyamine-polymer interaction. Structural analysis showed that polyamines bind PEG through hydrophobic and hydrophilic contacts with overall binding constants of Kspm-PEG-3000=3.1×10(4)M(-1), Kspmd-PEG-3000=5.5×10(4)M(-1), KBE-333-PEG-3000=2.5×10(4)M(-1), KBE-3333-PEG-3000=1.5×10(5)M(-1), Kspm-PEG-8000=4.1×10(5)M(-1), Kspmd-PEG-8000=7.5×10(5)M(-1), KBE-333-PEG-8000=4.5×10(4)M(-1), KBE-3333-PEG-8000=2.2×10(5)M(-1), Kspm-mPEG-ant=6.5×10(5)M(-1), Kspmd-mPEG-ant=1.1×10(6)M(-1), KBE-333-mPEG-ant=2.2×10(5)M(-1) and KBE-3333-mPEG-ant=6.9×10(4)M(-1). The number of binding sites (n) occupied by polyamines were from 0.2 to 0.5. Biogenic polyamines showed stronger affinity toward polymer complexation than synthetic polyamines, while weaker interaction was observed as polyamine cationic charges increased. Our results suggest that PEG and its derivative can act as carriers for delivering antitumor polyamine analogues to target tissues.

  5. Bioavailability and dissipation of anthracene from soil with different alkalinity and salinity.

    PubMed

    Castro-Silva, Carolina; Ruiz-Valdiviezo, Víctor Manuel; Rivas-Rivera, Sandra Gabriela; Sosa-Trinidad, Alma Rosa; Luna-Guido, Marco; Delgado-Balbuena, Laura; Marsch, Rodolfo; Dendooven, Luc

    2015-01-01

    Bioavailability of contaminants, such as anthracene (Anthra), a polycyclic aromatic hydrocarbon (PAHs), and their removal from soil has been related to their extractability with non-exhaustive techniques, such as hydroxypropyl-beta-cyclodextrin (HPCD) or n-butanol. Anthra was extracted with HPCD, n-butanol and by exhaustive ultrasonic extraction method from sterilized and unsterilized alkaline soil of the former lake Texcoco, having pH ranging from pH 8.2 to 10.1 and electrolytic conductivity varying from 1.2 dS m(-1) to 95.2 dS m(-1), respectively. About 24.4 and 37.6% of Anthra was removed biologically from soil as estimated by exhaustive technique after 56 days. The percentage of Anthra that was removed from soil by exhaustive technique was not related to the amount thatwas extractable with HPCD or n-butanol. It was found that the Anthra extractable with n-butanol or HPCD did not correlate well with the removal of the contaminant from soil. In this study, the removal of Anthra from soil could not be predicted by the amount of Anthra that was extracted with n-butanol or HPCD .

  6. Investigating the Anisotropic Scintillation Response in Anthracene through Neutron, Gamma-Ray, and Muon Measurements

    NASA Astrophysics Data System (ADS)

    Schuster, Patricia; Brubaker, Erik

    2016-06-01

    This paper reports a series of measurements that characterize the directional dependence of the scintillation response of crystalline anthracene to incident DT neutrons, DD neutrons, Cs-137 gamma rays, and, for the first time, cosmic ray muons. The neutron measurements give the amplitude and pulse shape dependence on the proton recoil direction over one hemisphere of the crystal, confirming and extending previous results in the literature. In similar measurements using incident gamma rays, no directional effect is evident, and any anisotropy with respect to the electron recoil direction is constrained to have a magnitude of less than a tenth of that present in the proton recoil events. Cosmic muons are measured at two directions, and no anisotropy is observed. This set of observations indicates that high dE/dx is necessary for an anisotropy to be present for a given type of scintillation event, which in turn could be used to discriminate among different hypotheses for the underlying causes of the anisotropy, which are not well understood.

  7. Anthracene and pyrene photolysis kinetics in aqueous, organic, and mixed aqueous-organic phases

    NASA Astrophysics Data System (ADS)

    Grossman, Jarod N.; Stern, Adam P.; Kirich, Makena L.; Kahan, Tara F.

    2016-03-01

    Condensed phases in the atmosphere, such as cloud droplets and aerosols, often contain both water and organic matter (OM). Reactivity can differ significantly between aqueous and organic phases. We have measured photolysis kinetics of the polycyclic aromatic hydrocarbons (PAHs) anthracene and pyrene in several organic solvents and in water, as well as in miscible and phase-separated aqueous-organic mixtures at atmospherically-relevant wavelengths. Photolysis rate constants generally increased with increasing solvent polarity; photolysis of both PAHs was more than ten times faster in water than in octanol. Local polarity had a much greater effect on PAH photolysis kinetics than changes in PAH absorptivity or singlet oxygen concentrations. Photolysis kinetics in homogeneous aqueous-organic mixtures varied monotonically with2 OM volume fraction. Kinetics in immiscible (phase-separated) solutions were more complex, with different dependences on OM content observed in stagnant and turbulent solutions. Our results suggest that OM could greatly affect the photochemical lifetimes of PAHs in atmospheric condensed phases such as aerosols, even if the OM does not itself absorb photons.

  8. Assessment of phytotoxicity of anthracene in soybean (Glycine max) with a quick method of chlorophyll fluorescence.

    PubMed

    Tomar, R S; Sharma, A; Jajoo, A

    2015-07-01

    A decrease in photosynthetic efficiency may indicate the toxic effects of environmental pollutants on higher plants. Measurement of chlorophyll (Chl) a fluorescence to assess the performance of photosystem II (PSII) was used as an bioindicator of toxicity of the polycyclic aromatic hydrocarbon (PAH) anthracene (ANT) in soybean plants. The results revealed that ANT treatment caused a reduction in quantum yield of PSII, damage to the oxygen evolving complex, as well as a significant reduction in performance index of PSII. However, change in performance index was more prominent, and it seems that the performance index is a more sensitive parameter to environmental contaminants. Moreover, a change in heterogeneity of PSII was also observed. The number of active reaction centres decreased with increasing concentration of ANT, as secondary plastoquinone reducing centres were converted into non-reducing centres, and PSIIα centres were converted into PSIIβ and PSIIγ centres. The influence of ANT on PSII heterogeneity could be an important reason for reductions in the PSII performance.

  9. Dietary rosemary suppresses 7,12-dimethylbenz(a)anthracene binding to rat mammary cell DNA.

    PubMed

    Amagase, H; Sakamoto, K; Segal, E R; Milner, J A

    1996-05-01

    Commercially available ground rosemary powder was examined for its ability to modify the in vivo binding of 7,12-dimethylbenz(a)anthracene (DMBA) metabolites to mammary cell DNA in 55-d-old rats fed diets containing varying quantities and types of lipids. Supplementing a casein-based diet containing 20% corn oil with 1 % rosemary for 2 wk reduced by 76% the occurrence of DMBA-induced DNA adducts occurring 24 h after treatment with 50 mg DMBA/kg body weight. A comparable reduction in DNA adducts (66%) occurred when 0.5% rosemary was added to a diet containing 20% corn oil, and the quantity of DMBA given was reduced to 25 mg/kg body weight. The reduction in the occurrence of adducts occurring 24 h after DMBA treatment caused by 0.5% dietary rosemary was greater (P < 0.05) when added to a diet containing 20% corn oil than when added to a diet containing 5% corn oil and 15% coconut oil. Rosemary, 1% but not 0.5%, reduced DMBA-induced DNA adducts when the diet contained 5% corn oil. These studies demonstrate that rosemary is effective in reducing the binding of DMBA metabolites to rat mammary cell DNA. Furthermore, the present studies demonstrate that the benefits of rosemary are dependent on the source and concentration of dietary lipids.

  10. Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals.

    PubMed

    Rudebusch, Gabriel E; Zafra, José L; Jorner, Kjell; Fukuda, Kotaro; Marshall, Jonathan L; Arrechea-Marcos, Iratxe; Espejo, Guzmán L; Ponce Ortiz, Rocío; Gómez-García, Carlos J; Zakharov, Lev N; Nakano, Masayoshi; Ottosson, Henrik; Casado, Juan; Haley, Michael M

    2016-08-01

    The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air- and temperature-stable biradical compound.

  11. Cell metabolic changes of porphyrins and superoxide anions by anthracene and benzo(a)pyrene.

    PubMed

    Uribe-Hernández, Raúl; Pérez-Zapata, Aura J; Vega-Barrita, María L; Ramón-Gallegos, Eva; Amezcua-Allieri, Myriam A

    2008-09-01

    The aim of this work was to evaluate the induction of protoporphyrins IX (PpIX) activity and superoxide anions (SO) in human leukocytes exposed to anthracene (ANT) and benzo(a)pyrene (B(a)P). The leukocyte LC(50)s for both hydrocarbons and the PpIX accumulation and SO overproduction were measured. The LC(50)s were 0.35 and 3.23μM for ANT and B(a)P, respectively. A linear relationship (r=0.97, p<0.01) between PpIX and ANT concentration was obtained. The induced accumulation of PpIX was proportional (r=0.63, p<0.01) to B(a)P concentration. SO overproduction showed a linear relationship (r=0.83, p<0.05) with ANT concentrations. The linear regression analysis of the effect of B(a)P on the superoxide anion overproduction showed a good coefficient (r=0.97, p<0.01), showed that ANT and B(a)P exposure induces PpIX accumulation, probably by disruption of the haem biosynthesis. ANT and B(a)P induce SO overproduction, perhaps through a process of redox cycling.

  12. Taurine Attenuates Dimethylbenz[a]anthracene-induced Breast Tumorigenesis in Rats: A Plasma Metabolomic Study.

    PubMed

    He, Y U; Li, Qingdi Quentin; Guo, Song Chao

    2016-02-01

    Breast cancer is the most common malignancy and the leading cause of cancer-related mortality in women worldwide. Taurine, the most abundant free amino acid, plays a role in several biological processes in humans and has been shown to have activity against breast cancer and other tumors. To investigate the role and mechanism of taurine action in breast cancer, we used dimethylbenz[a]anthracene (DMBA)-induced breast carcinogenesis in rats as a model of breast cancer. The administration of taurine significantly reduced the DMBA-induced breast cancer rate from 80% to 40% in rats (p<0.05). Metabolomic studies using time-of-flight gas chromatography-mass spectrometry identified 23 differential metabolites in the plasma of taurine-administered rats. Bioinformatic analysis further revealed that these metabolites are involved in multiple metabolic pathways, including energy, glucose, amino acid, and nucleic acid metabolism, suggesting that the antitumor activity of taurine in rats is mediated through altered metabolism of breast cancer cells. We propose that these differential metabolites may be potential biomarkers for monitoring cancer therapy and prognosis in the clinic. This study provides a scientific basis for further investigations of the antitumor mechanism of taurine and the development of novel therapeutic strategies to treat breast cancer.

  13. Large-scale correlated study of excited state absorptions in naphthalene and anthracene.

    PubMed

    Sony, Priya; Shukla, Alok

    2009-07-07

    In this paper, we report theoretical calculations of the photoinduced absorption (PA) spectrum of naphthalene and anthracene, with the aim of understanding those excited states, which are invisible in the linear optical absorption. The excited state absorption spectra are computed from the 1B(2u)(+) and the 1B(3u)(+) states and a detailed analysis of the many-body character of the states contributing to various peaks in the spectra is presented. The calculations are performed using the Pariser-Parr-Pople (PPP) Hamiltonian, along with the full configuration interaction technique. The role of Coulomb parameters used in the PPP Hamiltonian is examined by considering standard Ohno parameters, as well as a screened set of parameters. The results of our calculations are extensively compared with the experimental data where available and very good agreement has been obtained. Moreover, our calculations predict the presence of high intensity features which, to the best of our knowledge, have not been explored earlier. We also present concrete predictions on the polarization properties of the PA spectrum, which can be verified in experiments performed on oriented samples.

  14. Investigating the anisotropic scintillation response in anthracene through neutron, gamma-ray, and muon measurements

    SciTech Connect

    Schuster, Patricia; Brubaker, Erik

    2016-05-05

    Our paper reports a series of measurements that characterize the directional dependence of the scintillation response of crystalline anthracene to incident DT neutrons, DD neutrons, 137Cs gamma rays, and, for the first time, cosmic ray muons. Moreover, the neutron measurements give the amplitude and pulse shape dependence on the proton recoil direction over one hemisphere of the crystal, confirming and extending previous results in the literature. In similar measurements using incident gamma rays, no directional effect is evident, and any anisotropy with respect to the electron recoil direction is constrained to have a magnitude of less than a tenth of that present in the proton recoil events. Cosmic muons are measured at two directions, and no anisotropy is observed. Our set of observations indicates that high dE/dx is necessary for an anisotropy to be present for a given type of scintillation event, which in turn could be used to discriminate among different hypotheses for the underlying causes of the anisotropy, which are not well understood.

  15. High temperature polyimide containing anthracene moiety and its structure, interface, and nonvolatile memory behavior.

    PubMed

    Park, Samdae; Kim, Kyungtae; Kim, Dong Min; Kwon, Wonsang; Choi, Junman; Ree, Moonhor

    2011-03-01

    A high temperature polyimide bearing anthracene moieties, poly(3,3'-di(9-anthracenemethoxy)-4,4'-biphenylene hexafluoroisopropylidenediphthalimide) (6F-HAB-AM PI) was synthesized. The polymer exhibits excellent thermal stability up to around 410 °C. This polymer is amorphous but orients preferentially in the plane of nanoscale thin films. In device fabrications of its nanoscale thin films with metal top and bottom electrodes, no diffusion of the metal atoms or ions between the polymer and electrodes was found; however, the aluminum bottom electrode had somewhat undergone oxide layer (about 1.2 nm thick) formation at the surface during the post polymer layer formation process, which was confirmed to have no significant influence on the device performance. The polymer thin film exhibited excellent unipolar and bipolar switching behaviors over a very small voltage range, less than ±2 V. Further, the PI films show repeatable writing, reading, and erasing ability with long reliability and high ON/OFF current ratio (up to 10(7)) in air ambient conditions as well as even at temperatures up to 200 °C.

  16. Investigating the anisotropic scintillation response in anthracene through neutron, gamma-ray, and muon measurements

    DOE PAGES

    Schuster, Patricia; Brubaker, Erik

    2016-05-05

    Our paper reports a series of measurements that characterize the directional dependence of the scintillation response of crystalline anthracene to incident DT neutrons, DD neutrons, 137Cs gamma rays, and, for the first time, cosmic ray muons. Moreover, the neutron measurements give the amplitude and pulse shape dependence on the proton recoil direction over one hemisphere of the crystal, confirming and extending previous results in the literature. In similar measurements using incident gamma rays, no directional effect is evident, and any anisotropy with respect to the electron recoil direction is constrained to have a magnitude of less than a tenth ofmore » that present in the proton recoil events. Cosmic muons are measured at two directions, and no anisotropy is observed. Our set of observations indicates that high dE/dx is necessary for an anisotropy to be present for a given type of scintillation event, which in turn could be used to discriminate among different hypotheses for the underlying causes of the anisotropy, which are not well understood.« less

  17. Crystal induced phosphorescence from Benz(a)anthracene microcrystals at room temperature.

    PubMed

    Maity, Samir; Mazumdar, Prativa; Shyamal, Milan; Sahoo, Gobinda Prasad; Misra, Ajay

    2016-03-15

    Pure organic compounds that are also phosphorescent at room temperature are very rare in literature. Here, we report efficient phosphorescence emission from aggregated hydrosol of Benz(a)anthracene (BaA) at room temperature. Aggregated hydrosol of BaA has been synthesized by re-precipitation method and SDS is used as morphology directing agent. Morphology of the particles is characterized using optical and scanning electronic microcopy (SEM). Photophysical properties of the aggregated hydrosol are carried out using UV-vis, steady state and time resolved fluorescence study. The large stoke shifted structured emission from aggregated hydrosol of BaA has been explained due to phosphorescence emission of BaA at room temperature. In the crystalline state, the restricted intermolecular motions (RIM) such as rotations and vibrations are activated by crystal lattice. This rigidification effect makes the chromophore phosphorescent at room temperature. The possible stacking arrangement of the neighboring BaA within the aggregates has been substantiated by computing second order Fukui parameter as local reactivity descriptors. Computational study also reveals that the neighboring BaA molecules are present in parallel slipped conformation in its aggregated crystalline form.

  18. Crystal induced phosphorescence from Benz(a)anthracene microcrystals at room temperature

    NASA Astrophysics Data System (ADS)

    Maity, Samir; Mazumdar, Prativa; Shyamal, Milan; Sahoo, Gobinda Prasad; Misra, Ajay

    2016-03-01

    Pure organic compounds that are also phosphorescent at room temperature are very rare in literature. Here, we report efficient phosphorescence emission from aggregated hydrosol of Benz(a)anthracene (BaA) at room temperature. Aggregated hydrosol of BaA has been synthesized by re-precipitation method and SDS is used as morphology directing agent. Morphology of the particles is characterized using optical and scanning electronic microcopy (SEM). Photophysical properties of the aggregated hydrosol are carried out using UV-vis, steady state and time resolved fluorescence study. The large stoke shifted structured emission from aggregated hydrosol of BaA has been explained due to phosphorescence emission of BaA at room temperature. In the crystalline state, the restricted intermolecular motions (RIM) such as rotations and vibrations are activated by crystal lattice. This rigidification effect makes the chromophore phosphorescent at room temperature. The possible stacking arrangement of the neighboring BaA within the aggregates has been substantiated by computing second order Fukui parameter as local reactivity descriptors. Computational study also reveals that the neighboring BaA molecules are present in parallel slipped conformation in its aggregated crystalline form.

  19. Diindeno-fusion of an anthracene as a design strategy for stable organic biradicals

    NASA Astrophysics Data System (ADS)

    Rudebusch, Gabriel E.; Zafra, José L.; Jorner, Kjell; Fukuda, Kotaro; Marshall, Jonathan L.; Arrechea-Marcos, Iratxe; Espejo, Guzmán L.; Ponce Ortiz, Rocío; Gómez-García, Carlos J.; Zakharov, Lev N.; Nakano, Masayoshi; Ottosson, Henrik; Casado, Juan; Haley, Michael M.

    2016-08-01

    The consequence of unpaired electrons in organic molecules has fascinated and confounded chemists for over a century. The study of open-shell molecules has been rekindled in recent years as new synthetic methods, improved spectroscopic techniques and powerful computational tools have been brought to bear on this field. Nonetheless, it is the intrinsic instability of the biradical species that limits the practicality of this research. Here we report the synthesis and characterization of a molecule based on the diindeno[b,i]anthracene framework that exhibits pronounced open-shell character yet possesses remarkable stability. The synthetic route is rapid, efficient and possible on the gram scale. The molecular structure was confirmed through single-crystal X-ray diffraction. From variable-temperature Raman spectroscopy and magnetic susceptibility measurements a thermally accessible triplet excited state was found. Organic field-effect transistor device data show an ambipolar performance with balanced electron and hole mobilities. Our results demonstrate the rational design and synthesis of an air- and temperature-stable biradical compound.

  20. The anharmonic quartic force field infrared spectra of three polycyclic aromatic hydrocarbons: Naphthalene, anthracene, and tetracene

    SciTech Connect

    Mackie, Cameron J. Candian, Alessandra; Tielens, Alexander G. G. M.; Huang, Xinchuan; Maltseva, Elena; Buma, Wybren Jan; Petrignani, Annemieke; Oomens, Jos; Lee, Timothy J.

    2015-12-14

    Current efforts to characterize and study interstellar polycyclic aromatic hydrocarbons (PAHs) rely heavily on theoretically predicted infrared (IR) spectra. Generally, such studies use the scaled harmonic frequencies for band positions and double harmonic approximation for intensities of species, and then compare these calculated spectra with experimental spectra obtained under matrix isolation conditions. High-resolution gas-phase experimental spectroscopic studies have recently revealed that the double harmonic approximation is not sufficient for reliable spectra prediction. In this paper, we present the anharmonic theoretical spectra of three PAHs: naphthalene, anthracene, and tetracene, computed with a locally modified version of the SPECTRO program using Cartesian derivatives transformed from Gaussian 09 normal coordinate force constants. Proper treatments of Fermi resonances lead to an impressive improvement on the agreement between the observed and theoretical spectra, especially in the C–H stretching region. All major IR absorption features in the full-scale matrix-isolated spectra, the high-temperature gas-phase spectra, and the most recent high-resolution gas-phase spectra obtained under supersonically cooled molecular beam conditions in the CH-stretching region are assigned.

  1. Helium induced fine structure in the electronic spectra of anthracene derivatives doped into superfluid helium nanodroplets

    SciTech Connect

    Pentlehner, D.; Slenczka, A.

    2015-01-07

    Electronic spectra of organic molecules doped into superfluid helium nanodroplets show characteristic features induced by the helium environment. Besides a solvent induced shift of the electronic transition frequency, in many cases, a spectral fine structure can be resolved for electronic and vibronic transitions which goes beyond the expected feature of a zero phonon line accompanied by a phonon wing as known from matrix isolation spectroscopy. The spectral shape of the zero phonon line and the helium induced phonon wing depends strongly on the dopant species. Phonon wings, for example, are reported ranging from single or multiple sharp transitions to broad (Δν > 100 cm{sup −1}) diffuse signals. Despite the large number of example spectra in the literature, a quantitative understanding of the helium induced fine structure of the zero phonon line and the phonon wing is missing. Our approach is a systematic investigation of related molecular compounds, which may help to shed light on this key feature of microsolvation in superfluid helium droplets. This paper is part of a comparative study of the helium induced fine structure observed in electronic spectra of anthracene derivatives with particular emphasis on a spectrally sharp multiplet splitting at the electronic origin. In addition to previously discussed species, 9-cyanoanthracene and 9-chloroanthracene will be presented in this study for the first time.

  2. Solubility of anthracene and pyrene in binary alcohol + alcohol solvent mixtures

    SciTech Connect

    Zvaigzne, A.I.; McHale, M.E.R.; Powell, J.R.; Kauppila, A.S.M.; Acree, W.E. Jr.

    1995-11-01

    Solid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the petroleum industry, particularly in light of present trends toward heavier feedstocks and known carcinogenicity/mutagenicity of many of the larger polycyclic aromatic compounds. Experimental solubilities are reported for anthracene dissolved in binary 1-octanol + 2-propanol, 2-butanol + 1-butanol, 1-octanol + 1-butanol, 3-methyl-1-butanol + 1-propanol, and 2-methyl-1-propanol + 1-butanol mixtures at 25 C, and for pyrene dissolved in binary solvent mixtures containing 2-ethyl-1-hexanol with 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-octanol, 2-methyl-1-propanol, and 3-methyl-1-butanol at 26 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the 12 systems studied, the combined NIBS/Redlich-Kister equation was found to provide an accurate mathematical representation of the experimental data, with an overall average absolute deviation between measured and calculated values being on the order of 0.4%. Slightly larger deviations were noted in the case of the modified Wilson equation.

  3. Direct observation of the photodegradation of anthracene and pyrene adsorbed onto mangrove leaves.

    PubMed

    Wang, Ping; Wu, Tun-Hua; Zhang, Yong

    2014-01-01

    An established synchronous fluorimetry method was used for in situ investigation of the photodegradation of pyrene (PYR) and anthracene (ANT) adsorbed onto fresh leaves of the seedlings of two mangrove species, Aegiceras corniculatum (L.) Blanco (Ac) and Kandelia obovata (Ko) in multicomponent mixtures (mixture of the ANT and PYR). Experimental results indicated that photodegradation was the main transformation pathway for both ANT and PYR in multicomponent mixtures. The amount of the PAHs volatilizing from the leaf surfaces and entering the inner leaf tissues was negligible. Over a certain period of irradiation time, the photodegradation of both PYR and ANT adsorbed onto the leaves of Ac and Ko followed first-order kinetics, with faster rates being observed on Ac leaves. In addition, the photodegradation rate of PYR on the leaves of the mangrove species in multicomponent mixtures was much slower than that of adsorbed ANT. Compared with the PAHs adsorbed as single component, the photodegradation rate of ANT adsorbed in multicomponent mixtures was slower, while that of PYR was faster. Moreover, the photodegradation of PYR and ANT dissolved in water in multicomponent mixtures was investigated for comparison. The photodegradation rate on leaves was much slower than in water. Therefore, the physical-chemical properties of the substrate may strongly influence the photodegradation rate of adsorbed PAHs.

  4. Direct Observation of the Photodegradation of Anthracene and Pyrene Adsorbed onto Mangrove Leaves

    PubMed Central

    Wang, Ping; Wu, Tun-Hua; Zhang, Yong

    2014-01-01

    An established synchronous fluorimetry method was used for in situ investigation of the photodegradation of pyrene (PYR) and anthracene (ANT) adsorbed onto fresh leaves of the seedlings of two mangrove species, Aegiceras corniculatum (L.) Blanco (Ac) and Kandelia obovata (Ko) in multicomponent mixtures (mixture of the ANT and PYR). Experimental results indicated that photodegradation was the main transformation pathway for both ANT and PYR in multicomponent mixtures. The amount of the PAHs volatilizing from the leaf surfaces and entering the inner leaf tissues was negligible. Over a certain period of irradiation time, the photodegradation of both PYR and ANT adsorbed onto the leaves of Ac and Ko followed first-order kinetics, with faster rates being observed on Ac leaves. In addition, the photodegradation rate of PYR on the leaves of the mangrove species in multicomponent mixtures was much slower than that of adsorbed ANT. Compared with the PAHs adsorbed as single component, the photodegradation rate of ANT adsorbed in multicomponent mixtures was slower, while that of PYR was faster. Moreover, the photodegradation of PYR and ANT dissolved in water in multicomponent mixtures was investigated for comparison. The photodegradation rate on leaves was much slower than in water. Therefore, the physical-chemical properties of the substrate may strongly influence the photodegradation rate of adsorbed PAHs. PMID:25144741

  5. Obtaining the lattice energy of the anthracene crystal by modern yet affordable first-principles methods.

    PubMed

    Sancho-García, J C; Aragó, J; Ortí, E; Olivier, Y

    2013-05-28

    The non-covalent interactions in organic molecules are known to drive their self-assembly to form molecular crystals. We compare, in the case of anthracene and against experimental (electronic-only) sublimation energy, how modern quantum-chemical methods are able to calculate this cohesive energy taking into account all the interactions between occurring dimers in both first-and second-shells. These include both O(N(6))- and O(N(5))-scaling methods, Local Pair Natural Orbital-parameterized Coupled-Cluster Single and Double, and Spin-Component-Scaled-Møller-Plesset perturbation theory at second-order, respectively, as well as the most modern family of conceived density functionals: double-hybrid expressions in several variants (B2-PLYP, mPW2-PLYP, PWPB95) with customized dispersion corrections (-D3 and -NL). All-in-all, it is shown that these methods behave very accurately producing errors in the 1-2 kJ/mol range with respect to the experimental value taken into account the experimental uncertainty. These methods are thus confirmed as excellent tools for studying all kinds of interactions in chemical systems.

  6. TD-DFT study on the excited-state proton transfer in the fluoride sensing of a turn-off type fluorescent chemosensor based on anthracene derivatives.

    PubMed

    Song, Ping; Ding, Jun-Xia; Chu, Tian-Shu

    2012-11-01

    The sensing mechanism for fluoride chemosensor based on anthracene structure has been investigated by DFT and TDDFT methods. The results show that the similar geometries in S(0) and S(1) states in the absence of the fluoride anion induce the local excited (LE) state over the anthracene moiety, which is responsible for the strong fluorescence. The fluorescence quenching phenomenon for F-coordinated complex can be explained by the photoinduced electron transfer (PET) process from benzylic amide to anthracene moiety. Moreover, the strong electronegativity for fluoride anion in the F-complex constructs the intermolecular hydrogen bond of N-H…F in the ground state. In contrast, the upper proton in the urea group close to phenyl group prefers to bind fluoride anion in S(1) state of the F-complex, and it presents excited-state proton transfer (ESPT) to form another hydrogen bond like N…H-F, which has been confirmed by natural bond orbital (NBO) analysis and the potential energy curve of S(1) state for the function of N-H bond. In this novel and efficient fluoride fluorescent chemosensor based on anthracene, the anthracene moiety is regarded as not only the fluorescent source, but the template for introducing the binding sites for fluoride anion.

  7. Catalase-like activity of bovine met-hemoglobin: interaction with the pseudo-catalytic peroxidation of anthracene traces in aqueous medium.

    PubMed

    Paco, Laveille; Galarneau, Anne; Drone, Jullien; Fajula, François; Bailly, Carole; Pulvin, Sylviane; Thomas, Daniel

    2009-10-01

    Hemoglobin is a member of the hemoprotein superfamily whose main role is to transport O(2) in vertebrate organisms. It has two known promiscuous enzymatic activities, peroxidase and oxygenase. Here we show for the first time that bovine hemoglobin also presents a catalase-like activity characterized by a V(max )of 344 microM/min, a K(M )of 24 mM and a k(cat) equal to 115/min. For high anthracene and hemoglobin concentrations and low hydrogen peroxide concentrations, this activity inhibits the expected oxidation of anthracene, which occurs through a peroxidase-like mechanism. Anthracene belongs to the polycyclic aromatic hydrocarbon (PAH) family whose members are carcinogenic and persistent pollutants found in industrial waste waters. Our results show that anthracene oxidation by hemoglobin and hydrogen peroxide follows a typical bi-bi ping-pong mechanism with a V(max) equal to 0.250 microM/min, K(M(H2O2) )of 80 microM, K(M(ANT)) of 1.1 microM and k(cat) of 0.17/min. The oxidation of anthracene is shown to be pseudo-catalytic because an excess of hemoglobin and hydrogen peroxide is required to make PAH completely disappear. Thus, bovine hemoglobin presents, in different degrees, all the catalytic activities of the hemoprotein group, which makes it a very interesting protein for biotechnological processes and one with which structure-activity relationships can be studied.

  8. Synthesis, characterization and properties of yellow-light-emitting polyethers containing bis(styryl)anthracene units

    NASA Astrophysics Data System (ADS)

    Gioti, M.; Pitsalidis, C.; Andreopoulou, A. K.; Mparmpoutsis, E.; Tzounis, L.; Kallitsis, J. K.; Logothetidis, S.

    2015-02-01

    Aromatic aliphatic polyethers containing bis(styryl)anthracene units in the main chain separated by flexible spacer of 11 (AND52) or 12 (AND53) methylene units, were synthesized and characterized aiming to be applied as emitting materials in polymer light emitting diode (PLED) devices. The polymers are soluble in common organic solvents and have average molecular weight of about 15kDa. Differentiations owing to an odd-even number of methylene units (χ=11 vs χ=12) are observed in their optical properties in solid state. Thin films as well as PLED devices were fabricated via conventional spin-coating process. Initially, various parameters have been investigated concerning the solubility of the polymers, the effect of film thickness on the electrical properties, and their thermal stability. The optical properties of the two polymers were investigated by NIR-Vis-far UV spectroscopic ellipsometry (SE). The accurate determination of the thickness and the optical constants (refractive index and dielectric function as a function of wavelength) were derived. These provide substantial insights into the final design of the optimum final multi-layer structure of the PLEDs, if we take into account that the external quantum efficiency (EQE) of electroluminescence (EL) strongly depends on the optical interference of the beams of emitted light that have been multiply reflected from the layer interfaces. The morphological characterization of the AND52 and AND53 polymeric thin films was carried out using atomic force microscopy (AFM), while current density-voltage (J-V) characteristics of the devices were studied by electrical measurements. The single PLED devices were switched on at relatively low operation voltages, showing the potential as backplanes for active matrix PLED applications. In this perspective, it can be assumed that further studies of the presented materials will enable the development of flexible PLEDs with the possibility to scale up their dimensions for bigger

  9. A search for interstellar anthracene towards the Perseus anomalous microwave emission region

    NASA Astrophysics Data System (ADS)

    Iglesias-Groth, S.; Manchado, A.; Rebolo, R.; González Hernández, J. I.; García-Hernández, D. A.; Lambert, D. L.

    2010-10-01

    We report the discovery of a new broad interstellar (or circumstellar) band at 7088.8 +/- 2.0 Å coincident to within the measurement uncertainties with the strongest band of the anthracene cation (C14H10+) as measured in gas-phase laboratory spectroscopy at low temperatures. The band is detected in the line of sight of star Cernis 52, a likely member of the very young star cluster IC 348, and is probably associated with cold absorbing material in an intervening molecular cloud of the Perseus star-forming region where various experiments have recently detected anomalous microwave emission. From the measured intensity and available oscillator strength we find a column density of implying that ~0.008 per cent of the carbon in the cloud could be in the form of C14H10+. A similar abundance has been recently claimed for the naphthalene cation in this cloud. This is the first location outside the Solar system where specific polycyclic aromatic hydrocarbons (PAHs) are identified. We report observations of interstellar lines of CH and CH+ that support a rather high column density for these species and for molecular hydrogen. The strength ratio of the two prominent diffuse interstellar bands at 5780 and 5797 Å suggests the presence of a `zeta'-type cloud in the line of sight (consistent with steep far-ultraviolet extinction and high molecular content). The presence of PAH cations and other related hydrogenated carbon molecules which are likely to occur in this type of clouds reinforces the suggestion that electric dipole radiation from fast-spinning PAHs is responsible of the anomalous microwave emission detected towards Perseus.

  10. Piezochromism and structural and electronic properties of benz[a]anthracene under pressure.

    PubMed

    Cai, Weizhao; Zhang, Rong; Yao, Yansun; Deemyad, Shanti

    2017-02-22

    We report a combined experimental and theoretical study of the high pressure behavior of a herringbone-type hydrocarbon benz[a]anthracene (BaA) using fluorescence spectroscopy, X-ray diffraction, optical absorption, photoconductivity measurements, and first-principles density functional theory (DFT) calculations. The ambient-pressure molecular solid phase of BaA was found to be stable up to ∼15.0 GPa. Increasing the external pressure within this region would induce a reversible piezochromic colour change in the sample, from yellow-green to light brown. The reversibility of the colour change was confirmed by both optical observations and fluorescence measurements. Further compression beyond 15 GPa leads to polymerization of the sample and formation of an amorphous hydrogenated carbon. The low pressure crystalline phase is not recoverable when the sample is decompressed from pressure above 15 GPa. DFT investigation of the structures at zero temperature suggests that the formation of a crystalline polymeric phase can take place between 30 and 117 GPa, however the kinetic barriers hinder the process at low pressure regions. The phase transition is therefore suggested to proceed along a gradual transition path to an amorphous phase at a lower reaction threshold, activated by finite temperature effects. Optical absorption measurements reveal that the band gap of BaA decreases at high pressure, from 2.4 eV at 0.5 GPa to 1.0 eV at 50.6 GPa. The DFT calculations further suggest that the band gap of BaA in the molecular phase could reduce to ∼0.1 eV at 117 GPa. Photoconductivity measurements show a continuous increase of photocurrent in the molecular phase region, which most likely originated from the increase of carrier mobility under pressure.

  11. Synthesis, characterization and properties of yellow-light-emitting polyethers containing bis(styryl)anthracene units

    SciTech Connect

    Gioti, M. Pitsalidis, C. Tzounis, L.; Logothetidis, S.; Andreopoulou, A. K.; Kallitsis, J. K.; Mparmpoutsis, E.

    2015-02-17

    Aromatic aliphatic polyethers containing bis(styryl)anthracene units in the main chain separated by flexible spacer of 11 (AND52) or 12 (AND53) methylene units, were synthesized and characterized aiming to be applied as emitting materials in polymer light emitting diode (PLED) devices. The polymers are soluble in common organic solvents and have average molecular weight of about 15kDa. Differentiations owing to an odd-even number of methylene units (χ=11 vs χ=12) are observed in their optical properties in solid state. Thin films as well as PLED devices were fabricated via conventional spin-coating process. Initially, various parameters have been investigated concerning the solubility of the polymers, the effect of film thickness on the electrical properties, and their thermal stability. The optical properties of the two polymers were investigated by NIR-Vis-far UV spectroscopic ellipsometry (SE). The accurate determination of the thickness and the optical constants (refractive index and dielectric function as a function of wavelength) were derived. These provide substantial insights into the final design of the optimum final multi-layer structure of the PLEDs, if we take into account that the external quantum efficiency (EQE) of electroluminescence (EL) strongly depends on the optical interference of the beams of emitted light that have been multiply reflected from the layer interfaces. The morphological characterization of the AND52 and AND53 polymeric thin films was carried out using atomic force microscopy (AFM), while current density-voltage (J-V) characteristics of the devices were studied by electrical measurements. The single PLED devices were switched on at relatively low operation voltages, showing the potential as backplanes for active matrix PLED applications. In this perspective, it can be assumed that further studies of the presented materials will enable the development of flexible PLEDs with the possibility to scale up their dimensions for bigger

  12. Temperature-modulated carcinogenicity of 7,12-dimethylbenz[a]anthracene in rainbow trout.

    PubMed

    El-Zahr, Camille R; Zhang, Quan; Hendricks, Jerry D; Curtis, Lawrence R

    2002-06-14

    Temperature-modulated hepatic disposition, covalent binding of radiolabeled genotoxin to hepatic DNA, and cancer incidence in rainbow trout (Oncorhyncus mykiss) were assessed after a single exposure to 7,12-dimethylbenz[a]anthracene (DMBA). Fish (2 g) were acclimated at 10, 14, or 18 degrees C for 1 mo and then exposed to 1 ppm DMBA in their water for 20 h. Exposures were at respective acclimation temperatures, or 10 and 18 degrees C acclimated fish were shifted to 14 degrees C for DMBA exposures. After 4 but not 20 h of exposure, hepatic [(3)H]DMBA equivalents increased with temperature for fish exposed at their respective acclimation temperatures (10 or 18 degrees C). Covalent binding of [(3)H]DMBA to hepatic DNA was similar after 3 d in fish exposed at their respective acclimation temperatures. However, in fish exposed at 14 degrees C, after 3 d the concentration of [(3)H]DMBA covalently bound to hepatic DNA was higher in 10 degrees C than 18 degrees C acclimated fish. After 21 d, covalent binding of [(3)H]DMBA to hepatic DNA was less persistent in 18 degrees C than 10 degrees C acclimated, exposed, and reared fish. There were no differences between temperature-shifted groups at that time. Temperature effects on tumor incidence were assessed 9 mo after DMBA waterborne exposures in fish that were reared at (1) their respective acclimation and exposure temperatures, (2) 14 degrees C after exposure at their respective acclimation temperature, and (3) 14 degrees C after 14 degrees C exposures. Incidence of stomach, liver, and swimbladder cancer increased dramatically with rearing temperature. Differences in tumor incidence were less marked in fish reared at the same temperature (14 degrees C). A strong negative correlation between liver tumor incidence and persistence of [(3)H]DMBA equivalents covalently bound to hepatic DNA suggested increased error-prone DNA repair at warmer temperature played an important role in increased tumor incidence.

  13. Frequencies and Normal Modes of Vibration of Benz[a]anthracene Radical Ions

    NASA Astrophysics Data System (ADS)

    Kubba, Rehab M.; Al-ani, Raghida I.; Shanshal, Muthana

    2005-03-01

    MINDO/3-FORCES calculations were carried out for the radical ions of benz[a]anthracene. Both ions exhibit Cs symmetry with C-C bond alternation in all four rings. The obtained equilibrium geometry was applied for the calculation of all 3N - 6 vibration frequencies of each ion, and for the analysis of their normal coordinates. The so calculated frequencies of the radical cation were close to the experimental frequencies and those of the ab initio calculations. They fall in the ranges νCHstr. (3034 - 3087 cm-1), νCCstr. (1237 - 1609 cm-1), δCH (1142 - 1216 cm-1). Interesting correlations could be obtained for the frequencies of similar vibrations, e. g. νsymCHstr. >νasymCHstr. Exception is the frequency of vibration of CHα in ring A for the radical cation and the same bond in ring D for the radical anion. The vibration frequencies for the CH bonds depend on the σ -electron densities of the corresponding carbon atoms, i. e. νCH.+str. >νCHstr. >νCH.-str., where σ -ρĊ+ >σ -ρC >σ -ρĊ- . For the C-C stretching vibrations the relation ν(C-C)str. >ν(C-C).-str. >ν(C-C).+str. holds, with the exception of the Cβ -Cβ bond, for which the relation ν(C-C)str. >ν(C-C).+str. >ν(C-C).-str. is found. As for the in-plane and out of-plane deformations, the following general correlations δ (CH) >δ (CH).- >δ (CH).+ and γ (CC) >γ (CC).- >γ (CC).+.

  14. Persistence and fate of anthracene and benzo(a)pyrene in municipal sludge treated soil

    SciTech Connect

    Goodin, J.D.; Webber, M.D.

    1995-03-01

    Greenhouse studies using pots and microcosms were conducted to investigate the persistence and fate of nonlabeled and {sup 14}C-labeled anthracene (ANT) and benzo(a)Pyrene (B(a)P) in sludge treated soil. Results indicated that ANT degraded rapidly (t{sub {1/2}} {approx} 3 wk) from the experimental systems, but that B(a)P was persistent. Cropping did not affect the persistence of either compound. On completion of the experiments {le} 10% of the ANT added to soil was recovered intact, whereas 78% of the B(a)P added to soil was recovered intact. Most ({ge}85%) of the {sup 14}C added to soil as labeled ANT and B(a)P was accounted for. Recoveries of {sup 14}CO{sub 2} indicated significant mineralization of ANT, but not of B(a)P. Trivial amounts ({le}0.2%) of {sup 14}C were recovered as volatile organics and in plant materials, but large amounts were recovered from soil. A considerable proportion of the ANT derived {sup 14}C in soil was not extracted with acetone/hexane, which indicated that it had been converted to bound residue. a much smaller proportion of B(a)P than of ANT derived {sup 14}C in soil was converted to bound residue. No evidence was obtained for uptake of intact ANT or B(a)P by ryegrass (lolium multiflorum Lam.), soybean [Glycinemax (L.) Merr.], and cabbage (Brassica oleracea var. capitata L.). 25 refs., 3 figs., 6 tabs.

  15. Determination of anthracene on Ag-Au alloy nanoparticles/overoxidized-polypyrrole composite modified glassy carbon electrodes.

    PubMed

    Mailu, Stephen N; Waryo, Tesfaye T; Ndangili, Peter M; Ngece, Fanelwa R; Baleg, Abd A; Baker, Priscilla G; Iwuoha, Emmanuel I

    2010-01-01

    A novel electrochemical sensor for the detection of anthracene was prepared by modifying a glassy carbon electrode (GCE) with over-oxidized polypyrrole (PPyox) and Ag-Au (1:3) bimetallic nanoparticles (Ag-AuNPs). The composite electrode (PPyox/Ag-AuNPs/GCE) was prepared by potentiodynamic polymerization of pyrrole on GCE followed by its overoxidation in 0.1 M NaOH. Ag-Au bimetallic nanoparticles were chemically prepared by the reduction of AgNO(3) and HAuCl(4) using C(6)H(5)O(7)Na(3) as the reducing agent as well as the capping agent and then immobilized on the surface of the PPyox/GCE. The nanoparticles were characterized by UV-visible spectroscopy technique which confirmed the homogeneous formation of the bimetallic alloy nanoparticles. Transmission electron microscopy showed that the synthesized bimetallic nanoparticles were in the range of 20-50 nm. The electrochemical behaviour of anthracene at the PPyox/Ag-AuNPs/GCE with Ag: Au atomic ratio 25:75 (1:3) exhibited a higher electrocatalytic effect compared to that observed when GCE was modified with each constituent of the composite (i.e., PPyox, Ag-AuNPs) and bare GCE. A linear relationship between anodic current and anthracene concentration was attained over the range of 3.0 × 10(-6) to 3.56 × 10(-4) M with a detection limit of 1.69 × 10(-7) M. The proposed method was simple, less time consuming and showed a high sensitivity.

  16. Toxicity, feeding rate and growth rate response to sub-lethal concentrations of anthracene and benzo [a] pyrene in milkfish Chanos chanos (Forskkal).

    PubMed

    Palanikumar, L; Kumaraguru, A K; Ramakritinan, C M; Anand, M

    2013-01-01

    The feeding rate, growth rate and gross conversion efficiency were studied in milkfish Chanos chanos for 28 days of exposure to sub-lethal concentrations of anthracene (1.00, 2.00, 3.00, 6.00 and 12.0 μg l(-1)) and benzo [a] pyrene (0.30, 0.70, 1.40, 2.80 and 5.60 μg l(-1)) under continuous flow through bioassays. Based on survival and growth data, No Observed Effect Concentration; Lowest Observed Effect Concentration were estimated after 28 days, the values for anthracene were 2.03 and 3.09 μg l(-1), and the values for benzo [a] pyrene were 0.82 and 1.46 μg l(-1), respectively. Anthracene and benzo [a] pyrene exposure caused reduction in feeding and growth rate.

  17. Ecofriendly in-line process monitoring: a case study. Anthracene photodegradation in the presence of refuse-derived soluble bio-organics.

    PubMed

    Bianco Prevot, A; Avetta, P; Fabbri, D; Montoneri, E; Morales-Rubio, A; de la Guardia, M

    2012-08-01

    Photodegradation of anthracene has been studied in aqueous solutions containing soluble bio-organic substances isolated from urban refuse. To perform a preliminary rapid feasibility study of this process while reducing the amount of analytical effort and reagents, an experimental set-up was developed comprising a Teflon coil surrounding a UV-lamp and coupled with an in-line spectrofluorimeter. In this fashion only few millilitres of solution are needed to study the degradation process. Furthermore, the in-line spectroscopic approach enables monitoring of the process without consumption of reagents. Additional studies by liquid chromatography and use of toxicity tests clearly indicated that the apparent inhibition effect of bio-organic compounds on anthracene degradation is not relevant. The results imply that urban refuse may be used as an auxiliary in the recovery of polycyclic aromatic hydrocarbons from contaminated soil by washing, without deleterious effects on the photodegradation of anthracene and other aromatic pollutants.

  18. Linear acene derivatives - New routes to pentacene and naphthacene and the first synthesis of a triptycene with two anthracene moieties

    NASA Technical Reports Server (NTRS)

    Luo, Jihmei; Hart, Harold

    1987-01-01

    The cycloaddition of o-xylylene to arene 1,4-endoxides was used to construct linear arene derivatives. An analogous sequence but with naphthalene 1,4-endoxides gave naphthacenes. Dehydration of the di adducts from 4 and anthracene 1,4:5,8-diendoxides gave a mixture of 5,9,14,18- and 5,8,15,18-tetrahydroheptacenes 3 and 9. The previously unknown triptycene 2 was synthesized from 5,14-dihydropentacene, an intermediate in the new pentacene synthesis, in three steps and 29 percent overall yield.

  19. Facile synthesis of single-crystalline microwires based on anthracene derivative and their efficient optical waveguides and linearly polarized emission

    NASA Astrophysics Data System (ADS)

    Peng, Hong-Dan; Wang, Juan-Ye; Liu, Zheng-Hui; Pan, Ge-Bo

    2016-05-01

    The well-defined single-crystalline microwires of a solid-emissive organic functional molecule, 2-(anthracen-9-yl)-4, 5-diphenyl-1H-imidozole (ADPI) were successfully prepared by a facile solution process without the use of surfactant or additional templates. In addition, the optical loss coefficient is as low as 0.1 dB μm-1 for the as-prepared ADPI microwires, which is lower than most previous reported organic optical waveguides. Meanwhile, these microwires also show optically uniaxial properties as demonstrated by the linearly polarized emission, providing potentially orientation-sensitive applications as optical waveguides with low optical loss.

  20. Mono- and Dinuclear Manganese Carbonyls Supported by 1,8-Disubstituted (L = Py, SMe, SH) Anthracene Ligand Scaffolds.

    PubMed

    Manes, Taylor A; Rose, Michael J

    2016-06-06

    Presented herein is a synthetic scheme to generate symmetric and asymmetric ligands based on a 1,8-disubstituted anthracene scaffold. The metal-binding scaffolds were prepared by aryl chloride activation of 1,8-dichloroanthracene using Suzuki-type couplings facilitated by [Pd(dba)2] as a Pd source; the choice of cocatalyst (XPhos or SPhos) yielded symmetrically or asymmetrically substituted scaffolds (respectively): namely, Anth-SMe2 (3), Anth-N2 (4), and Anth-NSMe (6). The ligands exhibit a nonplanar geometry in the solid state (X-ray), owing to steric hindrance between the anthracene scaffold and the coupled aryl units. To determine the flexibility and binding characteristics of the anthracene-based ligands, the symmetric scaffolds were complexed with [Mn(CO)5Br] to afford the mononuclear species [(Anth-SMe2)Mn(CO)3Br] (8) and [(Anth-N2)Mn(CO)3Br] (9), in which the donor moieties chelate the Mn center in a cis fashion. The asymmetric ligand Anth-NSMe (6) binds preferentially through the py moieties, affording the bis-ligated complex [(Anth-NSMe)2Mn(CO)3Br] (10), wherein the thioether-S donors remain unbound. Alternatively, deprotection of the thioether in 6 affords the free thiol ligand Anth-NSH (7), which more readily binds the Mn center. Complexation of 7 ultimately affords the mixed-valence Mn(I)/Mn(II) dimer of formula [(Anth-NS)3Mn2(CO)3] (11), which exhibits a fac-{Mn(CO)3} unit supported by a triad of bridging thiolates, which are in turn ligated to a supporting Mn(II) center (EPR: |D| = 0.053 cm(-1), E/|D| = 0.3, Aiso = -150 MHz). All of the metal complexes have been characterized by single-crystal X-ray diffraction, IR spectroscopy and NMR/EPR measurements-all of which demonstrate that the meta-linked, anthracene-based ligand scaffold is a viable approach for the coordination of metal carbonyls.

  1. Light-dependent toxicity of α-terthienyl and anthracene toward late embryonic stages ofRana pipiens.

    PubMed

    Kagan, J; Kagan, P A; Buhse, H E

    1984-07-01

    Alpha-terthienyl is toxic to late embryonic stages ofRana pipiens in the presence of sunlight. Neither α-terthienyl alone in the dark nor a previously photolyzed solution of α-terthienyl has comparable activity. The LC50 was 0.11 ppm with 30 min of exposure and 0.018 ppm with 2 hr of exposure to sunlight. Anthracene, a representative example of polycyclic aromatic hydrocarbons widely distributed in the environment, also showed similar phototoxicity, with an LC50 of 0.065 ppm after 30 min of exposure and 0.025 ppm after 5 hr.

  2. Mutagenicity and tumorigenicity of the four enantiopure bay-region 3,4-diol-1,2-epoxide isomers of dibenz[a,h]anthracene.

    PubMed

    Chang, Richard L; Wood, Alexander W; Huang, Mou Tuan; Xie, Jian Guo; Cui, Xiao Xing; Reuhl, Kenneth R; Boyd, D R; Lin, Yong; Shih, Weichung Joe; Balani, Suresh K; Yagi, Haruhiko; Jerina, Donald M; Conney, Allan H

    2013-09-01

    Each enantiomer of the diastereomeric pair of bay-region dibenz[a,h]anthracene 3,4-diol-1,2-epoxides in which the benzylic 4-hydroxyl group and epoxide oxygen are either cis (isomer 1) or trans (isomer 2) were evaluated for mutagenic activity. In strains TA 98 and TA 100 of Salmonella typhimurium, the diol epoxide with (1S,2R,3S,4R) absolute configuration [(-)-diol epoxide-1] had the highest mutagenic activity. In Chinese hamster V-79 cells, the diol epoxide with (1R,2S,3S,4R) absolute configuration [(+)-diol epoxide-2] had the highest mutagenic activity. The (1R,2S,3R,4S) diol epoxide [(+)-diol epoxide-1] also had appreciable activity, whereas the other two bay-region diol epoxide enantiomers had very low activity. In tumor studies, the (1R,2S,3S,4R) enantiomer was the only diol epoxide isomer tested that had strong activity as a tumor initiator on mouse skin and in causing lung and liver tumors when injected into newborn mice. This stereoisomer was about one-third as active as the parent hydrocarbon, dibenz[a,h]anthracene as a tumor initiator on mouse skin; it was several-fold more active than dibenz[a,h]anthracene as a lung and liver carcinogen when injected into newborn mice. (-)-(3R,4R)-3β,4α-dihydroxy-3,4-dihydro-dibenz[a,h]anthracene [(-)-3,4-dihydrodiol] was slightly more active than dibenz[a,h]anthracene as a tumor initiator on mouse skin, whereas (+)-(3S,4S)-3α,4β-dihydroxy-3,4-dihydro-dibenz[a,h]anthracene [(+)-3,4-dihydrodiol] had only very weak activity. The present investigation and previous studies with the corresponding four possible enantiopure bay-region diol epoxide enantiomers/diastereomers of benzo[a]pyrene, benz[a]anthracene, chrysene, benzo[c]phenanthrene, dibenz[c,h]acridine, dibenz[a,h]acridine and dibenz[a,h]anthracene indicate that the bay-region diol epoxide enantiomer with [R,S,S,R] absolute stereochemistry has high tumorigenic activity on mouse skin and in newborn mice.

  3. Synthesis and Luminescent Chemosensory Behavior of N,N'-bis(p-aminophenyl)-1,5-bis(p-(tetraethyleneglycoloxy)phenyl)anthracene-2,3,6,7-tetracarboxyl bisimide

    NASA Technical Reports Server (NTRS)

    Ilhan, Faysal; Tyson, Daniel S.; Meador, Michael A.

    2004-01-01

    We have utilized the photoenolization reaction of a dibenzoyl-p-xylene derivative to synthesize two new, highly substituted anthracene-based molecules. ABI-NO2 and ABI-NH2 maintained photostability with longer wavelength absorption and emission spectra as compared to unsubstituted anthracene. Conversion of the periphery nitro groups to amines created an internal photoinduced electron transfer scenario that quenched the luminescence of ABI-NH2. Reversible or irreversible reaction of the attached amines resulted in fluorescence recovery. Sensitivity, of ABI-NH2 and other potential derivatives, to toxic chemicals may prove useful for early detection systems.

  4. Hybrid light-emitting diodes from anthracene-contained polymer and CdSe/ZnS core/shell quantum dots

    PubMed Central

    2014-01-01

    In this paper, we added CdSe/ZnS core/shell quantum dots (QDs) into anthracene-contained polymer. The photoluminescent (PL) characteristic of polymer/QD composite film could identify the energy transitions of anthracene-contained polymer and QDs. Furthermore, the electroluminescent (EL) characteristic of hybrid LED also identifies emission peaks of blue polymer and QDs. The maximum luminescence of the device is 970 cd/m2 with 9.1 wt.% QD hybrid emitter. The maximum luminous efficiency is 2.08 cd/A for the same device. PMID:25419194

  5. Chemical insight from density functional modeling of molecular adsorption: Tracking the bonding and diffusion of anthracene derivatives on Cu(111) with molecular orbitals

    SciTech Connect

    Wyrick, Jonathan; Bartels, Ludwig; Einstein, T. L.

    2015-03-14

    We present a method of analyzing the results of density functional modeling of molecular adsorption in terms of an analogue of molecular orbitals. This approach permits intuitive chemical insight into the adsorption process. Applied to a set of anthracene derivates (anthracene, 9,10-anthraquinone, 9,10-dithioanthracene, and 9,10-diselenonanthracene), we follow the electronic states of the molecules that are involved in the bonding process and correlate them to both the molecular adsorption geometry and the species’ diffusive behavior. We additionally provide computational code to easily repeat this analysis on any system.

  6. Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Hydrocarbon Cations. 3. The Polyacenes Anthracene, Tetracene, and Pentacene

    NASA Technical Reports Server (NTRS)

    Hudgins, D. M.; Allamandola, L. J.

    1995-01-01

    Gaseous, ionized Polycyclic Aromatic Hydrocarbons (PAH's) are thought to be responsible for a very common family of interstellar infrared emission bands. Unfortunately, very little infrared spectroscopic data are available on ionized PAH's. Here we present the near- and mid-infrared spectra of the polyacene cations anthracene, tetracene, and pentacene. We also report the vibrational frequencies and relative intensities of the pentacene anion. The cation bands corresponding to the CC modes are typically about 10-20 times more intense than those of the CH out-of-plane bending vibrations. For the cations the CC stretching and CH in-plane bending modes give rise to bands which are an order of magnitude stronger than for the neutral species, and the CH out-of-plane bends produce bands which are 3-20 times weaker than in the neutral species. This behavior is similar to that found for most other PAH cations. The most intense PAH cation bands fall within the envelopes of the most intense interstellar features. The strongest absorptions in the polyacenes anthracene, tetracene, and pentacene tend to group around 1400 / cm (between about 1340 and 1500 / cm) and near 1180 /cm, regions of only moderate interstellar emission. These very strong polyacene bands tend to fall in gaps in the spectra of the other PAH cations studied to date suggesting that while PAHs with polyacene structures may contribute to specific regions of the interstellar emission spectra, they are not dominant members of the interstellar PAH family.

  7. Infrared Spectroscopy of Matrix-Isolated Polycyclic Aromatic Hydrocarbon Cations. 3; The Polyacenes Anthracene, Tetracence, and Pentacene

    NASA Technical Reports Server (NTRS)

    Hudgins, D. M.; Allamandola, L. J.

    1995-01-01

    Gaseous, ionized polycyclic aromatic hydrocarbons (PAHS) are thought to be responsible for a very common family of interstellar infrared emission bands. Unfortunately, very little infrared spectroscopic data are available on ionized PAHS. Here we present the near- and mid-infrared spectra of the polyacene cations anthracene, tetracene, and pentacene. We also report the vibrational frequencies and relative intensities of the pentacene anion. The cation bands corresponding to the CC modes are typically about 10-20 times more intense than those of the CH out-of-plane bending vibrations. For the cations the CC stretching and CH in-plane bending modes give rise to bands which are an order of magnitude stronger than for the neutral species, and the CH out-of-plane bends produce bands which are 3-20 times weaker than in the neutral species. This behavior is similar to that found for most other PAH cations. The most intense PAH cation bands fall within the envelopes of the most intense interstellar features. The strongest absorptions in the polyacenes anthracene, tetracene, and pentacene tend to group around 1400/cm (between about 1340 and 1500/cm) and near 1180/cm, regions of only moderate interstellar emission. These very strong polyacene bands tend to fall in gaps in the spectra of the other PAH cations studied to date suggesting that while PAHs with polyacene structures may contribute to specific regions of the interstellar emission spectra, they are not dominant members of the interstellar PAH family.

  8. Effects of anthracene on filtration rates, antioxidant defense system, and redox proteomics in the Mediterranean clam Ruditapes decussatus (Mollusca: Bivalvia).

    PubMed

    Sellami, Badreddine; Khazri, Abdelhafidh; Louati, Héla; Dellali, Mohamed; Driss, Mouhamed Ridha; Aïssa, Patricia; Mahmoudi, Ezzeddine; Hamouda, Beyrem; Coelho, Ana Varela; Sheehan, David

    2015-07-01

    This study aimed at analyzing the impact of a toxic polyaromatic hydrocarbon (PAH), anthracene (ANT), on Ruditapes decussatus collected from a Tunisian coastal lagoon (Bizerte Lagoon). Filtration rates, several antioxidant enzymes--superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), glutathione reductase (GR), and glutathione transferase (GST)--as well as indices of protein oxidation status were determined in various tissues of this bivalve. Specimens were exposed to 100 μg/L of ANT for 2 days. ANT levels were evaluated using HPLC and were detected in the gill and digestive gland at different amounts. ANT exposure altered the behavior of bivalves by changing the siphon movement and decreasing filtration rate significantly. The enzymatic results indicated that ANT exposure affected the oxidative stress status of the gills of R. decussatus. In addition, modification of proteins was detected in the gills using redox proteomics after ANT treatment. Three protein spots were successfully identified by matrix-assisted laser desorption/ionization tandem time-of-flight mass spectrometry (MALDI-TOF-MS). These proteins can be roughly related to muscle contraction function. In contrast, no significant modification of enzymatic and protein responses was detected in the digestive gland after ANT treatment. These data demonstrate that combined behavioral and biochemical analyses are a powerful tool to provide valuable insights into possible mechanisms of toxicity of anthracene in R. decussatus. Additionally, the results highlight the potential of the gill as a valuable candidate for investigating PAH toxicity.

  9. Theoretical studies on electronic structures and photophysical properties of anthracene derivatives as hole-transporting materials for OLEDs.

    PubMed

    Chitpakdee, Chirawat; Namuangruk, Supawadee; Khongpracha, Pipat; Jungsuttiwong, Siriporn; Tarsang, Ruangchai; Sudyoadsuk, Taweesak; Promarak, Vinich

    2014-05-05

    The electronic structures and photophysical properties of anthracene derivatives as hole-transporting materials (HTM) in OLEDs have been studied by DFT and TD-DFT methods. Thiophene and triphenylamine (TPA) moieties are used as substituents in anthracene based HTMs providing FATn and FAPn compounds (n=1-2), respectively. The calculated electronic levels by B3LYP show proper energy matching of FAPn and hole-injecting layer (HIL), indicating that the hole-transports of the FAPn compounds are better than the FATn compounds. The photophysical properties calculated by TD-B3LYP elucidate that TPA in FAPn compounds acts as electron donating group and induces charge transfer character in the absorptions. Furthermore, the calculated ionization potential (IP), electron affinity (EA) and reorganization energies also revealed that the extended FAP2 compound has the highest charge-transporting ability among the studied compounds. The calculated results are consistent to our experimental observations showing that FAP2 exhibits bright fluorescence with highest quantum yield in electroluminescent devices. Understanding of these properties is useful for further design of new HTMs of desired properties, such as high efficiency and stability.

  10. Oxidative DNA damage induced by benz[a]anthracene dihydrodiols in the presence of dihydrodiol dehydrogenase.

    PubMed

    Seike, Kazuharu; Murata, Mariko; Hirakawa, Kazutaka; Deyashiki, Yoshihiro; Kawanishi, Shosuke

    2004-11-01

    Tobacco smoke and polluted air are risk factors for lung cancer and contain many kinds of polycyclic aromatic hydrocarbons (PAHs) including benzo[a]pyrene (B[a]P) and benz[a]anthracene (BA). BA, as well as B[a]P, is assessed as probably carcinogenic to humans (IARC group 2A). BA is metabolized to several dihydrodiols. Dihydrodiol dehydrogenase (DD), a member of the aldo-keto reductase superfamily, catalyzes NAD(P)+-linked oxidation of dihydrodiols of aromatic hydrocarbons to corresponding catechols. To clarify the role of DD on PAH carcinogenesis, we examined oxidative DNA damage induced by trans-dihydrodiols of BA and B[a]P treated with DD using 32P-5'-end-labeled DNA fragments obtained from the human p53 tumor suppressor gene. In addition, we investigated the formation of 8-oxo-7,8-dihydro-2'-deoxyguanosine (8-oxodG), an indicator of oxidative DNA damage, in calf thymus DNA by using HPLC with an electrochemical detector. DD-catalyzed BA-1,2-dihydrodiol caused Cu(II)-mediated DNA damage including 8-oxodG formation in the presence of NAD+. BA-1,2-dihydrodiol induced a Fpg sensitive and piperidine labile G lesion at the 5'-ACG-3' sequence complementary to codon 273 of the human p53 tumor suppressor gene, which is known as a hotspot. DNA damage was inhibited by catalase and bathocuproine, suggesting the involvement of H2O2 and Cu(I). The observation of NADH production by UV-visible spectroscopy suggested that DD catalyzed BA-1,2-dihydrodiol most efficiently to the corresponding catechol among the PAH-dihydrodiols tested. A time-of-flight mass spectroscopic study showed that the catechol form of BA-1,2-dihydrodiol formed after DD treatment. In conclusion, BA-1,2-dihydrodiol can induce DNA damage more efficiently than B[a]P-7,8-dihydrodiol and other BA-dihydrodiols in the presence of DD. The reaction mechanism on oxidative DNA damage may be explained by theoretical calculations with an enthalpy change of dihydrodiols and oxidation potential of their catechol forms. DD

  11. DFT study of the formation mechanism of anthraquinone from the reaction of NO2 and anthracene on NaCl clusters: the role of NaNO3.

    PubMed

    Luo, Chao; Yu, Qiming; Wang, Hongming

    2016-12-08

    Polycyclic aromatic hydrocarbons (PAHs) and oxygenated-PAHs are globally worrisome air pollutants because of their highly direct-acting mutagenicity and carcinogenicity. The formation of oxygenated-PAHs is of crucial importance for the prevention of their atmospheric pollution successfully. In this paper, the formation mechanism of oxygenated-PAHs from the heterogeneous reaction of NO2 with anthracene on the surface of NaCl was studied by density functional theory (DFT) calculations. At first, the various adsorption configurations of NO2 and N2O4 on NaCl were investigated. The chemical conversion mechanisms among these configurations were also investigated. It is found that these structures can easily interconvert due to their low energy barriers. NaNO3 was found to be the main product of the reaction of NO2/N2O4 on NaCl. Then the oxidation mechanism of anthracene by NO2 on the NaCl surface showed that NaNO3 is able to oxidize anthracene and plays a catalytic role in the reaction process. This means that the formation of NaNO3 is very important to promote the formation of 9,10-anthraquinone from the heterogeneous reaction of NO2 with anthracene. Our calculations also showed that the introduction of water can greatly accelerate this reaction process.

  12. Does anthracene affect microbial activities and organic matter decomposition? A comparative study in Pinus halepensis litters from Mediterranean coastal and inland areas.

    PubMed

    Qasemian, Leila; Guiral, Daniel; Ziarelli, Fabio; Ruaudel, Florence; Farnet, Anne-Marie

    2012-10-01

    The widespread concern about pollution caused by Polycyclic Aromatic Hydrocarbons (PAHs) raises the question of how they affect soil microbial communities which are potentially involved in the transformation of these pollutants. Using microcosms, we describe the effect of anthracene, a model PAH, on microbial communities inhabiting a Pinus halepensis litter from both coastal (COS) and inland (INL) Mediterranean sites. The microcosms were incubated over 3 months (25°C, 60% WHC) and the effects of anthracene on microbial activities of both litters were monitored. Different enzyme activities (laccase, cellulase, β-glucosidase and acid phosphatase) and microbial respiration were measured and variations in litter chemical composition over incubation were determined using (13)C Nuclear Magnetic Resonance (NMR) from both sites. Our results show that lignocellulolytic enzymes increased markedly after a 3-month incubation in COS microcosms, especially in the presence of anthracene, whereas INL microcosms were not similarly affected. These results show that anthracene not only has no toxic effect on the microbial activities tested but actually enhances the lignocellulolytic activities of the fungal communities from coastal litters, demonstrating the detoxification potential and resistance of stressed Mediterranean coastal ecosystems.

  13. DIELDRIN INDUCES CYTOSOLIC 7,12-[3H-]DIMETHYLBENZ[A]ANTHRACENE BINDING BUT NOT MULTIDRUG RESISTANCE PROTEINS IN RAINBOW TROUT LIVER.

    EPA Science Inventory

    Previously it was demonstrated that biliary excretion of a single dose of [14C]dieldrin or [3H]7,12-dimethylbenz[a]anthracene (DMBA) was stimulated up to 700% and 300%, respectively, in rainbow trout fed 0.3-0.4 mg dieldrin/kg/d for 9-12 wk. This was not explained by increased ac...

  14. Rhodium-Catalyzed Oxidative Benzannulation of N-Adamantyl-1-naphthylamines with Internal Alkynes via Dual C-H Bond Activation: Synthesis of Substituted Anthracenes.

    PubMed

    Zhang, Xuan; Yu, Xiaoqiang; Ji, Dingwei; Yamamoto, Yoshinori; Almansour, Abdulrahman I; Arumugam, Natarajan; Kumar, Raju Suresh; Bao, Ming

    2016-09-02

    Rhodium-catalyzed oxidative benzannulation of N-adamantyl-1-naphthylamines with internal alkynes to produce highly substituted anthracenes in satisfactory to good yields was developed. The annulation reaction proceeded smoothly under mild conditions in the presence of [Cp*RhCl2]2 as the precatalyst and Cu(OAc)2 as the oxidant.

  15. Bacteria capable of degrading anthracene, phenanthrene, and fluoranthene as revealed by DNA based stable-isotope probing in a forest soil.

    PubMed

    Song, Mengke; Jiang, Longfei; Zhang, Dayi; Luo, Chunling; Wang, Yan; Yu, Zhiqiang; Yin, Hua; Zhang, Gan

    2016-05-05

    Information on microorganisms possessing the ability to metabolize different polycyclic aromatic hydrocarbons (PAHs) in complex environments helps in understanding PAHs behavior in natural environment and developing bioremediation strategies. In the present study, stable-isotope probing (SIP) was applied to investigate degraders of PAHs in a forest soil with the addition of individually (13)C-labeled phenanthrene, anthracene, and fluoranthene. Three distinct phylotypes were identified as the active phenanthrene-, anthracene- and fluoranthene-degrading bacteria. The putative phenanthrene degraders were classified as belonging to the genus Sphingomona. For anthracene, bacteria of the genus Rhodanobacter were the putative degraders, and in the microcosm amended with fluoranthene, the putative degraders were identified as belonging to the phylum Acidobacteria. Our results from DNA-SIP are the first to directly link Rhodanobacter- and Acidobacteria-related bacteria with anthracene and fluoranthene degradation, respectively. The results also illustrate the specificity and diversity of three- and four-ring PAHs degraders in forest soil, contributes to our understanding on natural PAHs biodegradation processes, and also proves the feasibility and practicality of DNA-based SIP for linking functions with identity especially uncultured microorganisms in complex microbial biota.

  16. Identification of four trans-3,4-dihydrodiol metabolites of 7,12-dimethylbenz[a]anthracene and their in vitro DNA-binding activities upon further metabolism.

    PubMed Central

    Chou, M W; Yang, S K

    1978-01-01

    Trans-3,4-dihydrodiols of 7,12-dimethylbenz[a]anthracene (7,12-Me2BA), 7-methyl-12-hydroxymethylbenz[a]anthracene (7-Me-12-OHMeBA), 7-hydroxymethyl-12-methylbenz[a]anthracene (7-OHMe-12-MeBA), and 7,12-di(hydroxymethyl)benz[a]anthracene [7,12-(OHMe)2BA] have been identified as metabolites of the potent carcinogenic and adrenocorticolytic agent 7,12-MeBA. The four trans-3,4-dihydrodiols were identified by their (i) ultraviolet-visible absorption and fluorescence properties, (ii) different retention times on both reversed-phase and normal-phase high-pressure liquid chromatography, (iii) mass spectral analysis, and (iv) inability to form vicinal cis-acetonides. Upon further metabolism by liver microsomes, the trans-3,4-dihydrodiols of 7,12-Me2BA, 7-Me-12OHMeBA, and 7-OHMe-12-MeBA were found to give rise to products that bind more strongly to DNA in vitro than do the products of 7,12-Me2BA. The evidence suggests that one or more of the four trans-3,4-dihydrodiols may be the proximate carcinogenic and adrenocorticolytic metabolites. PMID:103094

  17. Improving Photovoltaic Performance of the Linear A-Ar-A-type Small Molecules with Diketopyrropyrrole Arms by Tuning the Linkage Position of the Anthracene Core.

    PubMed

    Duan, Xiongwei; Xiao, Manjun; Chen, Jianhua; Wang, Xiangdong; Peng, Wenhong; Duan, Linrui; Tan, Hua; Lei, Gangtie; Yang, Renqiang; Zhu, Weiguo

    2015-08-26

    Two isomeric A-Ar-A-type small molecules of DPP2An(9,10) and DPP2An(2,6), were synthesized with two acceptor arms of diketopyrropyrroles (DPP) and a planar aryl hydrocarbon core of the different substituted anthracene (An), respectively. Their thermal stability, crystallinity, optoelectronic, and photovoltaic performances were investigated. Significantly red-shifted absorption profile and higher HOMO level were observed for the DPP2An(2,6) with 2,6-substituted anthracene relative to the DPP2An(9,10) with 9,10-substituted anthracene, as the former exhibited better planarity and a larger conjugate system. As a result, the solution-processing solar cells based on DPP2An(2,6) and PC71BM (w/w,1:1) displayed remarkably increased power conversion efficiency of 5.44% and short-circuit current density (Jsc) of 11.90 mA/cm(2) under 1% 1,8-diiodooctane additive. The PCE and Jsc values were 3.7 and 2.9 times those of the optimized DPP2An(9,10)-based cells, respectively. This work demonstrates that changing the linkage position of the anthracene core in the A-Ar-A-type SMs can strongly improve the photovoltaic properties in organic solar cells.

  18. INDUCTION OF DNA ADDUCTS, TUMORS, AND KI-RAS ONCOGENE MUTATIONS IN STRAIN A/J MOUSE LUNG BY IP. ADMINISTRATION OF DIBENZ[A,H]ANTHRACENE

    EPA Science Inventory

    Induction of DNA adducts, tumors, and Ki-ras oncogene mutations in strain AlJ mouse lung by ip. administration of dibenz[a,h]anthracene

    Previous studies of polycyclic aromatic hydrocarbon (P AH) induced lung tumors in the strain NJ mouse model system have demonstrated qua...

  19. Lanthanide(III) complexes of 4,10-bis(phosphonomethyl)-1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (trans-H6do2a2p) in solution and in the solid state: structural studies along the series.

    PubMed

    Campello, M Paula C; Lacerda, Sara; Santos, Isabel C; Pereira, Giovannia A; Geraldes, Carlos F G C; Kotek, Jan; Hermann, Petr; Vanek, Jakub; Lubal, Premysl; Kubícek, Vojtech; Tóth, Eva; Santos, Isabel

    2010-07-26

    Complexes of 4,10-bis(phosphonomethyl)-1,4,7,10-tetraazacyclododecane-1,7-diacetic acid (trans-H(6)do2a2p, H(6)L) with transition metal and lanthanide(III) ions were investigated. The stability constant values of the divalent and trivalent metal-ion complexes are between the corresponding values of H(4)dota and H(8)dotp complexes, as a consequence of the ligand basicity. The solid-state structures of the ligand and of nine lanthanide(III) complexes were determined by X-ray diffraction. All the complexes are present as twisted-square-antiprismatic isomers and their structures can be divided into two series. The first one involves nona-coordinated complexes of the large lanthanide(III) ions (Ce, Nd, Sm) with a coordinated water molecule. In the series of Sm, Eu, Tb, Dy, Er, Yb, the complexes are octa-coordinated only by the ligand donor atoms and their coordination cages are more irregular. The formation kinetics and the acid-assisted dissociation of several Ln(III)-H(6)L complexes were investigated at different temperatures and compared with analogous data for complexes of other dota-like ligands. The [Ce(L)(H(2)O)](3-) complex is the most kinetically inert among complexes of the investigated lanthanide(III) ions (Ce, Eu, Gd, Yb). Among mixed phosphonate-acetate dota analogues, kinetic inertness of the cerium(III) complexes is increased with a higher number of phosphonate arms in the ligand, whereas the opposite is true for europium(III) complexes. According to the (1)H NMR spectroscopic pseudo-contact shifts for the Ce-Eu and Tb-Yb series, the solution structures of the complexes reflect the structures of the [Ce(HL)(H(2)O)](2-) and [Yb(HL)](2-) anions, respectively, found in the solid state. However, these solution NMR spectroscopic studies showed that there is no unambiguous relation between (31)P/(1)H lanthanide-induced shift (LIS) values and coordination of water in the complexes; the values rather express a relative position of the central ions between the N(4

  20. Photocontrol over the disorder-to-order transition in thin films of polystyrene-block-poly(methyl methacrylate) block copolymers containing photodimerizable anthracene functionality.

    PubMed

    Chen, Wei; Wang, Jia-Yu; Zhao, Wei; Li, Le; Wei, Xinyu; Balazs, Anna C; Matyjaszewski, Krzysztof; Russell, Thomas P

    2011-11-02

    Reversible photocontrol over the ordering transition of block copolymers (BCPs) from a disordered state to an ordered state, namely the disorder-to-order transition (DOT), can be used to create long-range ordered nanostructures in self-assembled BCPs over macroscopic distances by photocombing, similar to the classic zone refining used to produce highly pure, large single crystals. Here, we have designed and synthesized an anthracene-functionalized tri-BCP containing deuterated polystyrene (d(8)-PS) and poly(methyl methacrylate) (PMMA) blocks, as well as a short middle block of poly(2-hydroxyethyl methacrylates) (PHEMA) that is randomly functionalized by anthracene. This tri-BCP maintains the order-to-disorder transition-type phase behavior of its parent d(8)-PS-b-PMMA di-BCPs. Under 365 nm UV irradiation, the junction between d(8)-PS and PMMA blocks is photocoupled through the anthracene photodimers, leading to a significant increase in the total molecular weight of the tri-BCP. As a consequence, when the tri-BCP is phase-mixed but close to the boundary of the ordering transition, it undergoes the DOT, as evidenced by small-angle neutron scattering and transmission electron microscopy. The tri-BCP could be reversibly brought through the DOT in thin films by taking advantage of photodimerization and thermal dissociation of anthracene. Currently, anthracene-functionalized d(8)-PS-b-PMMA BCP is one of the most promising candidates for the photocombing process to promote long-range laterally ordered nanostructures over macroscopic distances in a noninvasive manner.

  1. Acute effects of Benzo[a]pyrene, anthracene and a fuel oil on biomarkers of the common goby Pomatoschistus microps (Teleostei, Gobiidae).

    PubMed

    Vieira, L R; Sousa, A; Frasco, M F; Lima, I; Morgado, F; Guilhermino, L

    2008-06-01

    The objective of this study was to investigate the effects of two different PAHs and a complex petrochemical mixture on the common goby, Pomatoschistus microps, using selected biomarkers as effect criteria. Benzo[a]pyrene (BaP) and anthracene were used as reference substances, while the water accommodated fraction of #4 fuel-oil (#4 WAF) was used as an example of a petrochemical mixture. P. microps was used since it is both a suitable bioindicator and a good test organism. Groups of fish were exposed to different concentrations of each of the test substances for 96 h and the activities of several enzymes commonly used as biomarkers were determined at the end of the bioassays. All the substances inhibited P. microps acetylcholinesterase (AChE) indicating that they have at least one mechanism of neurotoxicity in common: the disruption of cholinergic transmission by inhibition of AChE. An induction of lactate dehydrogenase (LDH) activity was found in fish exposed to BaP or to anthracene, suggesting an increase of the anaerobic pathway of energy production. On the contrary, inhibition of LDH was found in fish exposed to #4 WAF, suggesting a distinct effect of the mixture. An induction of P. microps glutathione S-transferase (GST) activity was found in fish exposed to BaP or to #4 WAF, while an inhibition was observed after exposure to anthracene. These results suggest that GST is involved in the detoxification of BaP and #4 WAF, but not of anthracene. All the substances increased catalase activity and isolated PAHs also increased superoxide dismutase, glutathione reductase and glutathione peroxidase activities, while #4 WAF did not cause significant alterations on these enzymes. These results suggest that all the substances may induce oxidative stress on P. microps, with BaP and anthracene apparently having more oxidative stress potential than #4 WAF.

  2. Chemistry of anthracene-acetylene oligomers XXV: on-surface chirality of a self-assembled molecular network of a fan-blade-shaped anthracene-acetylene macrocycle with a long alkyl chain.

    PubMed

    Tsuya, Takuya; Iritani, Kohei; Tahara, Kazukuni; Tobe, Yoshito; Iwanaga, Tetsuo; Toyota, Shinji

    2015-03-27

    An anthracene cyclic dimer with two different linkers and a dodecyl group was synthesized by means of coupling reactions. The calculated structure had a planar macrocyclic π core and a linear alkyl chain. Scanning tunneling microscopy observations at the 1-phenyloctane/graphite interface revealed that the molecules formed a self-assembled monolayer that consisted of linear striped bright and dark bands. In each domain, the molecular network consisted of either Re or Si molecules that differed in the two-dimensional chirality about the macrocyclic faces, which led to a unique conglomerate-type self-assembly. The molecular packing mode and the conformation of the alkyl chains are discussed in terms of the intermolecular interactions and the interactions between the molecules and the graphite surface with the aid of MM3 simulations of a model system.

  3. Effect of arginine on the carcinogenicity of 7,12-dimethylbenz[a]-anthracene and N-methyl-N-nitrosourea.

    PubMed

    Burns, R A; Milner, J A

    1984-12-01

    The effects of supplementing a 14% casein diet with 5% L-arginine on rat mammary tumors induced by 7,12-dimethylbenz[a]anthracene (DMBA) and N-methyl-N-nitrosourea (MNU) were investigated. Dietary arginine supplementation had no significant effect on food intake or growth. In rats treated with either DMBA or MNU, tumor incidence was not significantly affected, but the number of new tumors appearing each week and the cumulative tumor weight per rat were significantly decreased in rats fed 5% arginine diets. In vitro experiments indicated that arginine had no effect on the enzymatic conversion of DMBA to electrophilic DNA-binding metabolites. The decreased tumorigenicity of both MNU and DMBA in rats given supplemental arginine suggests that this amino acid has an inhibitory effect on stage(s) of chemical carcinogenesis other than bioactivation of procarcinogens.

  4. Isolation of novel benzo[a]anthracene-degrading microorganisms and continuous bioremediation in an expanded-bed bioreactor.

    PubMed

    Rosales, E; Pérez-Paz, A; Vázquez, X; Pazos, M; Sanromán, M A

    2012-06-01

    In the present work, several samples from lab waste containers polluted with polycyclic aromatic hydrocarbons (PAHs) and heavy metals were investigated as potential sources of PAH-degrading microorganisms. After isolating, two fungal strains were selected as the best degrading microorganisms. Genetic identification by sequencing was carried out and they were identified as Trichoderma longibrachiatum and Byssochlamys spectabilis. Their degradation ability was determined in liquid cultures with 100 μM of benzo[a]anthracene. T. longibrachiatum cultures showed highest degradation values (around 97%) after 9 days, furthermore in a second batch the time was reduced to 6 days. To analyse the viability of industrial application, a continuous treatment in an expanded-bed bioreactor was developed operating at different residence times with T. longibrachiatum immobilised on cubes of nylon sponge. It is noticeable that the bioreactor working in continuous mode was able to operate without operational problems and attaining high degradation levels depending on the residence time.

  5. Morphological characterization of cellular and extracellular components of 7,12 dimethylbenz[a]anthracene induced melanoma tumours.

    PubMed Central

    Persky, B.; Huerta, C. C.; Hendrix, M. J.

    1987-01-01

    Subcutaneous tumours were induced in castrated golden Syrian hamsters by 7,12 dimethylbenz[a]anthracene (DMBA), an agent known to produce papillomas and carcinomas. The morphological characteristics of the cellular and extracellular constituents of the chemically-induced tumours were indicative of melanoma. Tumours were induced by three injections of DMBA into the jugular vein over a 3 month period. Dermal tumour development within the dorsal integument and groin region ultimately projected into the epidermis and occurred during the 3 month period subsequent to the last DMBA injection. Suspect melanoma tumours were excised and processed for light microscopic (LM) and transmission electron microscopic (TEM) studies. Histochemical staining methods facilitated the characterization of the differentiated tumour components in this hamster melanoma model. The model presented could allow observations from initial melanoma transformation events through advanced stages of metastasis within a window of 7 months. Images Fig. 1 Fig. 2 Fig. 3 Fig. 4 PMID:3115285

  6. New anthracene glycosides from Rhodomyrtus tomentosa stimulate osteoblastic differentiation of MC3T3-E1 cells.

    PubMed

    Tung, Nguyen Huu; Ding, Yan; Choi, Eun Mi; Van Kiem, Phan; Van Minh, Chau; Kim, Young Ho

    2009-04-01

    Two new anthracene glycosides (1, 2) were isolated from aerial parts of Rhodomyrtus tomentosa, along with three known compounds (3-5). The structures of two new compounds were established to be 4,8,9,10-tetrahydroxy-2,3,7-trimethoxyanthracene-6-O-beta-D-glucopyranoside (1) and 2,4,7,8,9,10-hexahydroxy-3-methoxyanthracene-6-O-alpha-L-rhamnopyranoside (2) based on spectroscopic and chemical methods. Among them, compound 1, 2, and 5 significantly (P<0.05) increased the alkaline phosphatase activity, collagen synthesis, and mineralization of the nodules of MC3T3-E1 osteoblastic cells compared to those of the control, respectively.

  7. Effect of milk on the 7,12-dimethylbenz[a]-anthracene-induced mammary tumor model in rat.

    PubMed

    Zhou, Hong; Qin, Li-Qiang; Tang, Fu-Lei; Ma, De-Fu; Wang, Pei-Yu; Wang, Yan

    2007-10-01

    Milk may be one of the risk factors in the development of breast cancer from epidemiological investigations. Our study investigated the hormones and main ingredients in milk and assessed the effects of milk on the development of 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary tumors in rats by comparing differences among three groups: commercial milk (C), traditional milk (T) or water (W). During the 20-weeks experiment the C and T groups showed higher incidences of mammary tumors than the W group. After excluding potential confounding factors including fat and calcium, the C group was found to score higher than the T group in the indices of tumorigenesis. These findings suggested that DMBA-induced mammary tumors are more prevalent in milk-fed groups due in part to the contribution of estrogen and progesterone in milk.

  8. Dietary glucarate as anti-promoter of 7,12-dimethylbenz[a]anthracene-induced mammary tumorigenesis.

    PubMed

    Walaszek, Z; Hanausek-Walaszek, M; Minton, J P; Webb, T E

    1986-09-01

    Using as a criterion the inhibition of serum beta-glucuronidase activity, dietary calcium D-glucarate is shown to serve as an efficient slow-release source in vivo of D-glucaro-1,4-lactone, the potent endogenous inhibitor of this enzyme. Using the 7,12-dimethylbenz[a]anthracene model of mammary tumor induction in rats it is shown for the first time that feeding the rats calcium D-glucarate-supplemented diet after treatment with the carcinogen, inhibits tumor development by over 70%. Supportive evidence is presented for the theory that calcium D-glucarate inhibits or delays the promotion phase of mammary carcinogenesis by lowering endogenous levels of estradiol and precursors of 17-ketosteroids. Therefore, dietary glucarate can be used to lower blood and tissue levels of beta-glucuronidase, and in turn of those carcinogens and promoting agents which are excreted, at least in part, as glucuronide conjugates.

  9. Multiple effects of anthracene-9-carboxylic acid on the TMEM16B/anoctamin2 calcium-activated chloride channel.

    PubMed

    Cherian, O Lijo; Menini, Anna; Boccaccio, Anna

    2015-04-01

    Ca(2+)-activated Cl(-) currents (CaCCs) play important roles in many physiological processes. Recent studies have shown that TMEM16A/anoctamin1 and TMEM16B/anoctamin2 constitute CaCCs in several cell types. Here we have investigated for the first time the extracellular effects of the Cl(-) channel blocker anthracene-9-carboxylic acid (A9C) and of its non-charged analogue anthracene-9-methanol (A9M) on TMEM16B expressed in HEK 293T cells, using the whole-cell patch-clamp technique. A9C caused a voltage-dependent block of outward currents and inhibited a larger fraction of the current as depolarization increased, whereas the non-charged A9M produced a small, not voltage dependent block of outward currents. A similar voltage-dependent block by A9C was measured both when TMEM16B was activated by 1.5 and 13μM Ca(2+). However, in the presence of 1.5μM Ca(2+) (but not in 13μM Ca(2+)), A9C also induced a strong potentiation of tail currents measured at -100mV after depolarizing voltages, as well as a prolongation of the deactivation kinetics. On the contrary, A9M did not produce potentiation of tail currents, showing that the negative charge is required for potentiation. Our results provide the first evidence that A9C has multiple effects on TMEM16B and that the negative charge of A9C is necessary both for voltage-dependent block and for potentiation. Future studies are required to identify the molecular mechanisms underlying these complex effects of A9C on TMEM16B. Understanding these mechanisms will contribute to the elucidation of the structure and functional properties of TMEM16B channels.

  10. Individual and combined effect of anthracene, cadmium, and chloridazone on growth and activity of SOD izoformes in three Scenedesmus species.

    PubMed

    Zbigniew, Tukaj; Wojciech, Pokora

    2006-11-01

    Short-term (12-48 h) experiments were carried out to examine the effect of anthracene (three-ring aromatic hydrocarbon), cadmium (CdCl(2)), and chloridazone (triazine herbicide), individually and in combination, on growth and SOD activity of three green algae Scenedesmus: S. subspicatus, S. obliquus, and S. microspina, grown in a batch-culture system. The relative toxicity of chemicals to algae was anthracene > chloridazone > cadmium. The species revealed similar growth sensitivity to individual chemicals after 24 h of exposure but there were differences between them when exposed to their combinations. Two methods were used to determine the modes of interaction effects of the chemical combinations; both led to the same results, with two exceptions of all 36 variants examined. In general, mixtures of two and three chemicals behaved toward algal growth mainly in an antagonistic manner (20 cases), whereas additive and synergistic interaction occurred 13 and 3 times, respectively. Antagonism was the most frequently observed to growth of S. obliquus; antagonistic interaction and additive effect was noted in relation to S. subspicatus, while response of S. microspina depended markedly on applied combination. There is a relationship between SOD activity and growth response to stress. The markedly higher level of SOD isoforms activities was noticed in cells (especially S. microspina and S. obliquus) exposed to 12 h to combined chemicals, as compared to individually treated and control cells. SOD activities in cells of three Scenedesmus grown 24 h were similar in all experimental variants and after 48 h of exposure significantly decreased in almost all cases (especially in S. subspicatus). There were no differences observed between SOD profiles obtained for all variants examined. Chloroplasts seems to be the main target site of interaction effects of dissimilarly acting chemicals.

  11. Photophysical and Photochemical Studies of Poly-cyclic Aromatic Hydrocarbons in Solutions Containing Tetrachloromethane. I. Fluorescence Quenching of Anthracene by Tetrachloromethane and its Complexes with Benzene, p-Xylene and Mesitylene

    NASA Astrophysics Data System (ADS)

    Wiczk, Wiesław M.; Latowski, Tadeusz

    1986-05-01

    Fluorescence quenching of anthracene has been studied in two-component mixtures of CCl4 with cyclohexane, benzene, p-xylene and mesitylene. Non-typical quenching curves have been found in mixtures containing benzene and its derivatives.

  12. Theoretical study of electronically excited radical cations of naphthalene and anthracene as archetypal models for astrophysical observations. Part I. Static aspects.

    PubMed

    Ghanta, S; Reddy, V Sivaranjana; Mahapatra, S

    2011-08-28

    Motivated by the recent discovery of new diffuse interstellar bands and results from laboratory experiments, ab initio quantum chemistry calculations are carried out for the lowest six electronic states of naphthalene and anthracene radical cations. The calculated adiabatic electronic energies are utilized to construct suitable diabatic electronic Hamiltonians in order to perform nuclear dynamics studies in Part II. Complex entanglement of the electronic states is established for both the radical cations and the coupling surfaces among them are also derived in accordance with the symmetry selection rules. Critical examination of the coupling parameters of the Hamiltonian suggests that 29 (out of 48) and 31 (out of 66) vibrational modes are relevant in the nuclear dynamics in the six lowest electronic states of naphthalene and anthracene radical cations, respectively.

  13. The presence of the mutagenic polycyclic aromatic hydrocarbons benzo[a]pyrene and benz[a]anthracene in creosote P1.

    PubMed

    Bos, R P; Theuws, J L; Leijdekkers, C M; Henderson, P T

    1984-06-01

    Several fractions of creosote P1 separated by TLC showed mutagenicity towards Salmonella typhimurium TA98. Thus mutagenicity is probably caused by the presence of mutagenic aromatic hydrocarbons. The mutagenic polycyclic aromatic hydrocarbons, benzo[a]pyrene and benz[a]anthracene, were detected in concentrations of 0.18 and 1.1% respectively. Because these compounds are probably not essential for the wood-preserving properties of creosote , a more selective composition of the product should be considered.

  14. Reduced energy intake and moderate exercise reduce mammary tumor incidence in virgin female BALB/c mice treated with 7,12-dimethylbenz(a)anthracene

    NASA Technical Reports Server (NTRS)

    Lane, Helen W.; Teer, Patricia; Keith, Robert E.; White, Marguerite T.; Strahan, Susan

    1991-01-01

    The concurrent effects of diet (standard AIN-76A, restricted AIN-76A and high-fat diet) and moderate rotating-drum treadmill exercise on the incidence of 7,12-dimethylbenz(a)anthracene-induced mammary carcinomas in virgin female BALB/cMed mice free of murine mammary tumor virus are evaluated. Analyses show that, although energy intake was related to mammary tumor incidence, neither body weight nor dietary fat predicted tumor incidence.

  15. Ant 4,4, a polyamine-anthracene conjugate, induces cell death and recovery in human promyelogenous leukemia cells (HL-60).

    PubMed

    Traquete, Rui; Ghani, Radiah A; Phanstiel, Otto; Wallace, Heather M

    2013-04-01

    One of the major problems in cancer therapy is the lack of specificity of chemotherapeutic agents towards cancer cells, resulting in adverse side effects. One means to counter this is to selectively deliver the drug to the cancer cell. Cancer cells accumulate increased concentrations of polyamines compared to normal cells, mainly through an increased uptake of preformed polyamines via the polyamine transport system (PTS). Furthermore, the non-stringent structural requirements of the PTS enable the transport of a range of polyamine-based molecules. Thus, the PTS can be used to transport compounds linked to polyamines selectively to cancer cells. In our laboratory, polyamine-anthracene conjugates have shown potent anti-tumour activity towards HL-60 cells. The aim of this study was to determine the cytotoxicity of Ant-4,4, a homospermidine-anthracene conjugate, and assess the long-term effects by determining whether cancer cells were able to recover from treatment. During exposure, Ant-4,4 was an effective growth-inhibitory agent in HL-60 cells decreasing viable cell number, protein and polyamine content. Evidence indicates concomitant cell-cycle arrest and increased apoptosis. Once the drug was removed, HL-60 cells recovered gradually over time. Increasing cell number, protein content and polyamine content, as well as diminished effects on cell-cycle and apoptotic stimuli were observed over time. These data suggest that, despite being an effective way of delivering anthracene, these polyamine conjugates do not exert long-lasting effects on HL-60 cells.

  16. Hexose uptake in 7,12-dimethylbenz(a)anthracene-preexposed rat tracheal epithelial cells during the progression of neoplasia

    SciTech Connect

    Wasilenko, W.J.; Marchok, A.C.

    1984-07-01

    Hexose uptake during the progression of neoplasia in rat tracheal epithelial cells was studied by measuring the uptake of 2-deoxy(/sup 3/H)glucose (2-dGlc) in nontumorigenic (C-18) and tumorigenic (T-8, 1000-WT) rat tracheal epithelial cell lines with varying degrees of cell association as well as in: (a) normal primary cell cultures (NPC) derived from explants of nonexposed tracheas; (b) selected primary cell cultures (SPC) generated from explants of 7,12-dimethylbenz(a)anthracene-treated tracheal implants; and (c) primary tumor cell cultures (TPC) derived from explants of 7,12-dimethylbenz(a)anthracene-induced tracheal carcinomas. The latter two groups represented cells from earlier and late states in the progression of neoplasia, respectively, and each displayed an in vitro growth advantage that allowed for their survival and growth in medium devoid of supplements of pyruvate and insulin. This property was used in this study to select the carcinogen-altered cells from neighboring normal cells. Uptake of 2-dGlc per ..mu..g of DNA was similar in subconfluent cultures of all cell lines. At confluency, uptake per ..mu..g of DNA was reduced markedly (>3-fold) in C-18 cells but it was reduced only 1.3-fold in T-8 cells and 1.6-fold in 1000-WT cells. Hexose uptake was further reduced in T-8 and 1000-WT cell cultures generated as outgrowths from explants of denuded tracheas bearing a reestablished epithelium from each cell line. Under these conditions, T-8 cells retained higher 2-dGlc uptake than did C-18, but uptake by 1000-WT was lower, indicating that tissue-like cell associations have a profound effect on hexose uptake in these epithelial cells. Results were generally similar when uptake was expressed per mg of protein although, in several instances, the interpretation of uptake data was affected by differences in the protein content between cultures. 46 references, 1 figure, 7 tables.

  17. Evaluation of chlorinated benz[a]anthracene on hepatic toxicity in rats and mutagenic activity in Salmonella typhimurium.

    PubMed

    Kido, T; Sakakibara, H; Ohura, T; Guruge, K S; Kojima, M; Hasegawa, J; Iwamura, T; Yamanaka, N; Masuda, S; Sakaguchi, M; Amagai, T; Shimoi, K

    2013-01-01

    Chlorinated benz[a]anthracenes (Cl-BaA) are halogenated aromatic compounds (typified by dioxins) found in the environment at relatively high concentrations. Fischer 344 rats were intragastrically administered 0, 1, or 10 mg of Cl-BaA or its parent compound benz[a]anthracene (BaA) per kg of body weight for 14 consecutive days. Both chemicals at 10 mg/kg/day inhibited the gain in body weight, and consequent increase in relative liver weight. Hepatic gene expression of cytochrome P450 (CYP) 1A1, 1A2, and 1B1 was significantly stimulated by administration of BaA (10 mg/kg/day) compared with the control. After administration of Cl-BaA, only the CYP1A2 gene was significantly induced, even at the lower dosage; CYP1A1 and 1B1 mRNA levels remained unchanged in Cl-BaA-treated rats compared with controls. To elucidate the role of such Cl-BaA exposure and induced CYPs at toxicity onset, we investigated the mutagenicity of BaA and Cl-BaA using Salmonella typhimurium TA98 and TA100. BaA and Cl-BaA at 10 μg/plate produced positive results in both strains in the presence of rat S-9. Incubation of Cl-BaA with recombinant rat CYP1A2 produced a significantly higher number of revertant colonies in TA98 and TA100 than in controls, but no such change was observed for BaA. In conclusion, BaA changes its own physiological and toxicological actions by its chlorination; (1) daily exposure to Cl-BaA selectively induces hepatic CYP1A2 in rats and (2) Cl-BaA induces frameshift mutations in the presence of CYP1A2, although BaA does not exert mutagenicity. This indicates that CYP1A2 may metabolize Cl-BaA to active forms.

  18. Unraveling the electronic structures of low-valent naphthalene and anthracene iron complexes: X-ray, spectroscopic, and density functional theory studies.

    PubMed

    Schnöckelborg, Eva-Maria; Khusniyarov, Marat M; de Bruin, Bas; Hartl, František; Langer, Thorsten; Eul, Matthias; Schulz, Stephen; Pöttgen, Rainer; Wolf, Robert

    2012-06-18

    Naphthalene and anthracene transition metalates are potent reagents, but their electronic structures have remained poorly explored. A study of four Cp*-substituted iron complexes (Cp* = pentamethylcyclopentadienyl) now gives rare insight into the bonding features of such species. The highly oxygen- and water-sensitive compounds [K(18-crown-6){Cp*Fe(η(4)-C(10)H(8))}] (K1), [K(18-crown-6){Cp*Fe(η(4)-C(14)H(10))}] (K2), [Cp*Fe(η(4)-C(10)H(8))] (1), and [Cp*Fe(η(4)-C(14)H(10))] (2) were synthesized and characterized by NMR, UV-vis, and (57)Fe Mössbauer spectroscopy. The paramagnetic complexes 1 and 2 were additionally characterized by electron paramagnetic resonance (EPR) spectroscopy and magnetic susceptibility measurements. The molecular structures of complexes K1, K2, and 2 were determined by single-crystal X-ray crystallography. Cyclic voltammetry of 1 and 2 and spectroelectrochemical experiments revealed the redox properties of these complexes, which are reversibly reduced to the monoanions [Cp*Fe(η(4)-C(10)H(8))](-) (1(-)) and [Cp*Fe(η(4)-C(14)H(10))](-) (2(-)) and reversibly oxidized to the cations [Cp*Fe(η(6)-C(10)H(8))](+) (1(+)) and [Cp*Fe(η(6)-C(14)H(10))](+) (2(+)). Reduced orbital charges and spin densities of the naphthalene complexes 1(-/0/+) and the anthracene derivatives 2(-/0/+) were obtained by density functional theory (DFT) methods. Analysis of these data suggests that the electronic structures of the anions 1(-) and 2(-) are best represented by low-spin Fe(II) ions coordinated by anionic Cp* and dianionic naphthalene and anthracene ligands. The electronic structures of the neutral complexes 1 and 2 may be described by a superposition of two resonance configurations which, on the one hand, involve a low-spin Fe(I) ion coordinated by the neutral naphthalene or anthracene ligand L, and, on the other hand, a low-spin Fe(II) ion coordinated to a ligand radical L(•-). Our study thus reveals the redox noninnocent character of the naphthalene

  19. Using acetone as solvent to study removal of anthracene in soil inhibits microbial activity and alters nitrogen dynamics.

    PubMed

    Núñez, Edgar Vázquez; Rodríguez, Viviana; Gaytán, Alejandro García; Luna-Guido, Marco; Betancur-Galvis, Liliana A; Marsch, Rodolfo; Dendooven, Luc

    2009-08-01

    Acetone is often used as a carrier to contaminate soil with polycyclic aromatic hydrocarbons (PAHs) and then to study the factors that control their removal. Acetone is an organic solvent that might affect soil processes. An alkaline saline (Texcoco soil) and an agricultural soil (Acolman soil) were amended with or without acetone, nitrogen + phosphorus (NP), and contaminated with anthracene at 520 mg/kg soil while emissions of CO2 and N2O and concentrations of NH4+, NO2(-) and NO3(-) were monitored. The CO2 emission rate decreased greater than 10 times in the soils amended with acetone. Emission of N2O decreased 70 times in the Acolman soil amended with acetone and NP and 5 times in the Texcoco soil. The concentration of NH4+ decreased in the unamended Acolman and Texcoco soil but increased when acetone was added in the first and remained constant in the latter. Acetone inhibited the increase in the amount of NO3(-) in the Acolman soil but not in the Texcoco soil. It was found that microbial activity as evidenced by the emission of CO2, nitrification, and production of N2O were inhibited by acetone. The amount of acetone used as solvent should thus be kept to a minimum, but it can be assumed that its effect on soil processes will be temporary, as microorganisms are known to repopulate soil quickly.

  20. Polyvinyl pyrrolidone capped fluorescent anthracene nanoparticles for sensing fluorescein sodium in aqueous solution and analytical application for ophthalmic samples.

    PubMed

    Bhopate, Dhanaji P; Mahajan, Prasad G; Garadkar, Kalyanrao M; Kolekar, Govind B; Patil, Shivajirao R

    2015-11-01

    Based on the known complexation ability between polyvinyl pyrrolidone (PVP) and fluorescein sodium (FL Na(+)), fluorescent PVP capped anthracene nanoparticles (PVP-ANPs) were prepared using a reprecipitation method for detection of fluorescein in aqueous solution using the fluorescence resonance energy transfer (FRET) approach. A dynamic light scattering histogram of PVP-ANPs showed narrower particle size distribution and the average particle size was 15 nm. The aggregation-induced enhanced emission (AIEE) of PVP-ANPs was red shifted from its monomer by 1087.22 cm(-1). The maximum emission was seen to occur at 420 nm. The presence of FL Na(+) in the vicinity of PVP-ANPs quenched the fluorescence of PVP-ANPs because of its adsorption on the surface of PVP-ANPs in aqueous suspension. The FL Na(+) and PVP-ANPs were brought close enough, typically to 7.89 nm, which was less than the distance of 10 nm that is required between the energy donor-acceptor molecule for efficient FRET. The quenching results fit into the Stern-Volmer relationship even at temperatures greater than ambient temperatures. The thermodynamic parameters determined from FRET results helped to propose binding mechanisms involving hydrophobic and electrostatic molecular interaction. The fluorescence quenching results were used further to develop an analytical method for estimation of fluorescein sodium from ophthalmic samples available commercially in the market.

  1. Protection Against Dimethylbenz[a] Anthracene-Induced Breast Cancer in Female Rats by α-Lactalbumin

    PubMed Central

    Roy, Somdutta Sinha; Mukherjee, Shyamali; Ballard, Billy R; Das, Salil K

    2016-01-01

    Consumption of α-lactalbumin as dietary protein offers a beneficial effect on breast cancer development. Breast cancer was developed by gavage administration of single dose of dimethylbenz(a)anthracene (DMBA) in female rats, maintained on AIN-76A diet with either 20% casein or α-lactalbumin (a component of whey protein). All tumors were detected by palpation. After approximately 130 days of DMBA administration, the animals were euthanized. There was a delay in the development of breast tumor in the α-lactalbumin group in comparison to the casein group. The number of tumors per rat was less in the α-lactalbumin group than that in the casein group at any time point up to 130 days after DMBA administration. Also the incidence of tumors and tumor volume was less in the α-lactalbumin group than those in the casein group. The casein group had a mixture of grade I, grade II and grade III tumors whereas the α-lactalbumin group had mostly grade I tumor. Furthermore, the proliferative index was significantly lower in the α-lactalbumin group than that in the casein group. PMID:27517093

  2. Antioxidant potential of black tea against 7,12-dimethylbenz(a)anthracene- induced oxidative stress in Swiss albino mice.

    PubMed

    Kalra, Neetu; Prasad, Sahdeo; Shukla, Yogeshwer

    2005-01-01

    Oxygen free radicals and related reactive species have been implicated in the etiology of many diseases, such as atherosclerosis, neurodegenerative disorders, and cancer. Antioxidant enzymes exist in cells to protect against the effects of these free radicals and other oxygen-derived species, which are produced during the oxidative stress. Tea (Camellia sinensis) is the most commonly consumed beverage worldwide. Both green and black tea are known to possess many pharmacological properties, including antioxidant, antipyretic, antibacterial, and antineoplastic effects. In the present study, the preventive effects of black tea extract (BTE) was evaluated in Swiss albino mice against 7,12-dimethyl benz(a)anthracene (DMBA)-induced oxidative stress. The animals were given 0.5%, 1%, and 1.5% BTE as the sole source of drinking solution for 1 week prior to the administration of DMBA, which was given orally as a single dose of 50 mg/kg body weight. At the end of the study period, the liver, kidney, and prostate tissues were dissected out for the determination of antioxidant enzyme levels (catalase, superoxide dismutase, glutathione reductase, glutathione-S-transferase), and lipid peroxidation. A dose-dependent protective effect of BTE against DMBA-induced depletion in enzymes activity was observed in all three tissues examined. Similarly, a significant dose-dependent inhibition of the lipid peroxidation caused by DMBA was observed in the BTE-administered animals in all three tissues examined. Our results revealed that BTE provides protection against oxidative damage induced by xenobiotics.

  3. Photolysis rates of selected polynuclear aromatic hydrocarbons in aqueous coal-oil systems. [Fluoranthene, benzo(a)anthracene

    SciTech Connect

    Picel, K.C.; Stamoudis, V.C.; Simmons, M.S.

    1983-01-01

    Four polynuclear aromatic hydrocarbons (PAH) from the neutral fraction of synfuels materials - fluoranthene (FLA), pyrene (PY), benzo(a)anthracene (BaA), and benzo(a)pyrene (BaP) - were selected as representative test compounds based on toxicity, abundance, and chemical characteristics. BaA and BaP are established carcinogens, and FLA is a suspected cocarcinogen. Pyrene, which is not thought to be carcinogenic, was included for comparison to FLA, which has the same molecular weight but different structural properties. The synthetic fuel material used in this study was CRM-1, a coal-oil comparative research material obtained from Oak Ridge National Laboratory. For PY, BaA, and BaP in aqueous systems, initial photolysis rates are six to nine times lower in coal-oil (CRM-1) saturated water than in pure water. However, the photolysis rate of FLA is not significantly different under the same conditions. It is possible that the photochemical mechanisms inhibited in the photoreactive PAH are not operational in FLA. Since the calculated light attenuation can account only partially for the observed reduction of the photolysis rates of PY, BaA, and BaP, it is likely that other factors - especially the presence of phenols - are affecting the photodegradation process of these PAH. Further studies are needed to investigate the individual effects on PAH photolysis rates of the various classes of compounds that make up the coal-oil matrix. 20 references, 2 figures, 4 tables.

  4. Taurine Regulates Mitochondrial Function During 7,12-Dimethyl Benz[a]anthracene Induced Experimental Mammary Carcinogenesis

    PubMed Central

    Vanitha, Manickam Kalappan; Priya, Kalpana Deepa; Baskaran, Kuppusamy; Periyasamy, Kuppusamy; Saravanan, Dhravidamani; Venkateswari, Ramachandran; Mani, Balasundaram Revathi; Ilakkia, Aruldass; Selvaraj, Sundaramoorthy; Menaka, Rajendran; Geetha, Mahendran; Rashanthy, Nadarajah; Anandakumar, Pandi; Sakthisekaran, Dhanapal

    2015-01-01

    Objectives: The present study was undertaken to determine the modulatory effect of taurine on the liver mitochondrial enzyme system with reference to mitochondrial lipid peroxidation (LPO), antioxidants, major tricarboxylic acid cycle enzymes, and electron transport chain enzymes during 7,12-dimethyl benz[a]anthracene (DMBA) induced breast cancer in Sprague-Dawley rats. Methods: Animals in which breast cancer had been induced by using DMBA (25 mg/kg body weight) showed an increase in mitochondrial LPO together with decreases in enzymic antioxidants (superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx), glutathione reductase (GR) and glutathione-S-transferase (GST)), non-enzymic antioxidants (reduced glutathione (GSH), vitamin C, and vitamin E), in citric acid cycle enzymes (isocitrate dehydrogenase (ICDH), alpha ketoglutarate dehydrogenase (alpha KDH), succinate dehydrogenase (SDH) and malate dehydrogenase (MDH)), and in electron transport chain (ETC) complexes. Results: Taurine (100 mg/kg body weight) treatment decreased liver mitochondrial LPO and augmented the activities/levels of enzymic, and non-enzymic antioxidants, tricarboxylic acid cycle enzymes and ETC complexes. Conclusion: The results of our present study demonstrated the chemotherapeutic efficacy of taurine treatment for DMBA-induced breast carcinomas. PMID:26389003

  5. Solubility of anthracene in binary alcohol + 2-methyl-1-propanol and alcohol + 3-methyl-1-butanol solvent mixtures

    SciTech Connect

    Zvaigzne, A.I.; Acree, W.E. Jr.

    1995-07-01

    Solid-liquid equilibrium data of organic nonelectrolyte systems are becoming increasingly important in the petroleum industry, particularly in light of present rends toward heavier feedstocks and known carcinogenicity/mutagenicity of many of the larger polycyclic aromatic compounds. Experimental solubilities are reported for anthracene dissolved in binary 2-propanol + 3-methyl-1-butanol, 2-propanol + 2-methyl-1-propanol, 1-propanol + 2-methyl-1-propanol, 1-octanol + 2-methyl-1-propanol, 1-butanol + 3-methyl-1-butanol, 2-butanol + 3-methyl-1-butanol, 2-butanol + 2-methyl-1-propanol, 1-octanol + 3-methyl-1-butanol, and 2-methyl-1-propanol + 3-methyl-1-butanol solvent mixtures at 25 C. Results of these measurements are used to test two mathematical representations based upon the combined nearly ideal binary solvent (NIBS)/Redlich-Kister equation and modified Wilson model. For the systems studied, the combined NIBS/Redlich-Kister and modified Wilson equations were found to provide very reasonable mathematical representations, with most deviations between experimental and back-calculated values being on the order of {+-} 1.0% or less.

  6. Microemulsions of N-alkylimidazolium ionic liquid and their performance as microreactors for the photocycloaddition of 9-substituted anthracenes.

    PubMed

    Li, Xin-Wei; Zhang, Jin; Zheng, Li-Qiang; Chen, Bin; Wu, Li-Zhu; Lv, Feng-Feng; Dong, Bin; Tung, Chen-Ho

    2009-05-19

    The phase behavior of the ternary system consisting of an ionic liquid (1-tetradecyl-3-methylimidazolium bromide [C14mim]Br), p-xylene, and water were investigated. Depending on the composition of the ternary system, formation of hexagonal and lamellar liquid crystals as well as microemulsions was observed. 1H NMR spectroscopy study, 2D ROESY spectroscopic analysis, and rheological measurements of the microemulsions indicated that p-xylene is preferably located in the hydrophobic core and the palisade shells of the microemulsions. The sizes of the microemulsion droplets for the samples with water/[C14mim]Br ratio of 78:22 are measured by both dynamic light scattering (DLS) and transmission electron microscopy with the freeze-fracture technique (FF-TEM). Upon change of the mole ratio of the solubilized xylene to [C14mim]Br from 0 to 2.4, the diameters of the microemulsion droplets increase from ca. 20 to 90 nm and size distribution gets broad. These microemulsions can solubilize and preorientate anthracene derivatives with a polar 9-substituent, and thus may enhance the head-to-head cyclomers in the photocyclization of these substrates.

  7. Terahertz spectroscopy and solid-state density functional theory calculation of anthracene: effect of dispersion force on the vibrational modes.

    PubMed

    Zhang, Feng; Hayashi, Michitoshi; Wang, Houng-Wei; Tominaga, Keisuke; Kambara, Ohki; Nishizawa, Jun-ichi; Sasaki, Tetsuo

    2014-05-07

    The phonon modes of molecular crystals in the terahertz frequency region often feature delicately coupled inter- and intra-molecular vibrations. Recent advances in density functional theory such as DFT-D(*) have enabled accurate frequency calculation. However, the nature of normal modes has not been quantitatively discussed against experimental criteria such as isotope shift (IS) and correlation field splitting (CFS). Here, we report an analytical mode-decoupling method that allows for the decomposition of a normal mode of interest into intermolecular translation, libration, and intramolecular vibrational motions. We show an application of this method using the crystalline anthracene system as an example. The relationship between the experimentally obtained IS and the IS obtained by PBE-D(*) simulation indicates that two distinctive regions exist. Region I is associated with a pure intermolecular translation, whereas region II features coupled intramolecular vibrations that are further coupled by a weak intermolecular translation. We find that the PBE-D(*) data show excellent agreement with the experimental data in terms of IS and CFS in region II; however, PBE-D(*) produces significant deviations in IS in region I where strong coupling between inter- and intra-molecular vibrations contributes to normal modes. The result of this analysis is expected to facilitate future improvement of DFT-D(*).

  8. Terahertz spectroscopy and solid-state density functional theory calculation of anthracene: Effect of dispersion force on the vibrational modes

    NASA Astrophysics Data System (ADS)

    Zhang, Feng; Hayashi, Michitoshi; Wang, Houng-Wei; Tominaga, Keisuke; Kambara, Ohki; Nishizawa, Jun-ichi; Sasaki, Tetsuo

    2014-05-01

    The phonon modes of molecular crystals in the terahertz frequency region often feature delicately coupled inter- and intra-molecular vibrations. Recent advances in density functional theory such as DFT-D* have enabled accurate frequency calculation. However, the nature of normal modes has not been quantitatively discussed against experimental criteria such as isotope shift (IS) and correlation field splitting (CFS). Here, we report an analytical mode-decoupling method that allows for the decomposition of a normal mode of interest into intermolecular translation, libration, and intramolecular vibrational motions. We show an application of this method using the crystalline anthracene system as an example. The relationship between the experimentally obtained IS and the IS obtained by PBE-D* simulation indicates that two distinctive regions exist. Region I is associated with a pure intermolecular translation, whereas region II features coupled intramolecular vibrations that are further coupled by a weak intermolecular translation. We find that the PBE-D* data show excellent agreement with the experimental data in terms of IS and CFS in region II; however, PBE-D* produces significant deviations in IS in region I where strong coupling between inter- and intra-molecular vibrations contributes to normal modes. The result of this analysis is expected to facilitate future improvement of DFT-D*.

  9. Inhibitory effects of chlorophyllin on 7,12-dimethylbenz[a]anthracene-induced bacterial mutagenesis and mouse skin carcinogenesis.

    PubMed

    Chung, W Y; Lee, J M; Park, M Y; Yook, J I; Kim, J; Chung, A S; Surh, Y J; Park, K K

    1999-10-18

    Chlorophyllin (CHL), a water-soluble derivative of chlorophyll, has been used for the treatment of several abnormal human conditions without apparent toxicity. Recent studies have revealed that CHL has the excellent chemopreventive potential. In the present investigation, we have found the inhibitory activities of CHL against 7,12-dimethylbenz[a]anthracene (DMBA)-induced mutagenesis in Salmonella typhimurium TA100 and also on DMBA-initiated and 12-O-tetradecanoyl-phorbol-13-acetate (TPA)-promoted mouse skin tumor formation. The incidence and the multiplicity of skin tumors were not significantly decreased in mice by a single topical application of CHL prior to the DMBA treatment, but there was a marked suppression of papillomagenesis in mice treated with CHL during the promotional stage. Furthermore, the formation of DMBA-induced papillomagenesis was reduced in all mice that had received CHL for 6 weeks following treatment with TPA for 6, 18 and 24 weeks. These results indicate that CHL can inhibit both tumor promotion and the progression of papillomagenesis in the two-stage mouse skin carcinogenesis induced by DMBA and TPA.

  10. Initiation of cell proliferation in livers of the viviparous fish Poeciliopsis lucida with 7,12-dimethylbenz(a)anthracene

    SciTech Connect

    Schultz, M.E.; Kaplan, L.A.E.; Schultz, R.J. )

    1989-04-01

    Stimulation of liver cell proliferation by sublethal exposures to 7,12-dimethylbenz(a)anthracene (DMBA) is examined in the small, viviparous fish Poeciliopsis lucida. Poeciliopsis is susceptible to induction of liver tumors by repeated short-term exposures, under 24 hr, to waterborne DMBA at 5 ppm. Exposures to 5 ppm for 24 hr was lethal to fish under 1 month old and resulted in 60% mortality of adult females 20-25 mm in length. Response to 16-, 20-, and 22-hr exposures of 5 ppm DMBA, as measured by mitotic index, was similar in females of two size classes, 20-25 mm and 26-30 mm. Differences were observed in the onset of mitosis in livers of fish exposed for 16 hr vs 20 or 22 hr. Hepatocyte proliferation did not begin until 10-11 days after the 16-hr exposure and lasted for only 3 days. When exposure was increased to 20 or 22 hr, mitotic activity was observed earlier, 2 days following treatment, and continued for 6-8 days. The peak period of cell proliferation also varied, occurring 12 days after a 16-hr exposure, 4 days after a 20-hr exposure, and at least 10 days after a 22-hr exposure. The mitotic index was the highest on the final day specimens of the 22-hr treatment were collected. These results suggest that the toxic properties of DMBA in stimulating cell proliferation may function as an important cofactor in hepatocarcinogenesis.

  11. Anthracene-containing wide-band-gap conjugated polymers for high-open-circuit-voltage polymer solar cells.

    PubMed

    Gong, Xue; Li, Cuihong; Lu, Zhen; Li, Guangwu; Mei, Qiang; Fang, Tao; Bo, Zhishan

    2013-07-25

    The synthesis, characterization, and photophysical and photovoltaic properties of two anthracene-containing wide-band-gap donor and acceptor (D-A) alternating conjugated polymers (P1 and P2) are described. These two polymers absorb in the range of 300-600 nm with a band gap of about 2.12 eV. Polymer solar cells with P1:PC71 BM as the active layer demonstrate a power conversion efficiency (PCE) of 2.23% with a high Voc of 0.96 V, a Jsc of 4.4 mA cm(-2) , and a comparable fill factor (FF) of 0.53 under simulated solar illumination of AM 1.5 G (100 mW cm(-2) ). In addition, P2:PC71 BM blend-based solar cells exhibit a PCE of 1.42% with a comparable Voc of 0.89 V, a Jsc of 3.0 mA cm(-2) , and an FF of 0.53.

  12. erbB expression changes in ethanol and 7, 12- dimethylbenz (a) anthracene-induced oral carcinogenesis

    PubMed Central

    Jacinto-Alemán, Luis F.; García-Carrancá, Alejandro; Leyba-Huerta, Elba R.; Zenteno-Galindo, Edgar; Jiménez-Farfán, María D.

    2013-01-01

    Objetive: The aim of this study was to determine erbB expression in normal mucosa, oral dysplasia, and invasive carcinomas developed in the hamster’s buccal pouch chemical carcinogenesis model. Study design: Fifty Syrian golden hamsters were equally divided in five groups (A-E); two controls and three experimental group exposed to alcohol, DMBA, or both for 14 weeks. Number of tumors per cheek, volume, histological condition, erbB expression were determined and results were analyzed by the Mann–Whitney U and Dunn’s test. Results: Control groups and those exposed to alcohol (A, B and C respectively) only presented clinical and histological normal mucosa; while those exposed to DMBA or DMBA plus alcohol (D and E groups) developed dysplasia and invasive carcinomas. erbB2, erbB3, and erbB4 increased their expression in alcohol-exposed mucosa, dysplasia, and invasive carcinomas. We observed a similar expression level for erbB2 in dysplasia and carcinomas; while, erbB3 and erbB4 were similar only in carcinomas. Conclusion: The DMBA and alcohol can be considered as carcinogen and promoter for oral carcinogenesis. The erbB expression is different according to their histological condition, suggesting differential participation of the erbB family in oral carcinogenesis induced by alcohol and DMBA. Key words:erbB, 7,12- dimethylbenz(a)anthracene, oral squamous cell carcinoma. PMID:23229248

  13. Chemopreventive efficacy of Moringa oleifera pods against 7, 12-dimethylbenz[a]anthracene induced hepatic carcinogenesis in mice.

    PubMed

    Sharma, Veena; Paliwal, Ritu; Janmeda, Pracheta; Sharma, Shatruhan

    2012-01-01

    Oxidative stress is a common mechanism contributing to initiation and progression of hepatic damage in a variety of liver disorders. Hence there is a great demand for the development of agents with potent antioxidant effect. The aim of the present investigation is to evaluate the efficacy of Moringa oleifera as a hepatoprotective and an antioxidant against 7, 12-dimethylbenz[a]anthracene induced hepatocellular damage. Single oral administration of DMBA (15 mg/kg) to mice resulted in significantly (p<0.001) depleted levels of xenobiotic enzymes like, cytochrome P450 and b5. DMBA induced oxidative stress was confirmed by decreased levels of reduced glutathione (GSH) and glutathione-S-transferase (GST) in the liver tissue. The status of hepatic aspartate transaminase (AST), alanine transaminase (ALT), and alkaline phosphatase (ALP) which is indicative of hepatocellular damage were also found to be decreased in DMBA administered mice. Pretreatment with the Moringa oleifera (200 and 400 mg/kg) orally for 14 days significantly reversed the DMBA induced alterations in the liver tissue and offered almost complete protection. The results from the present study indicate that Moringa oleifera exhibits good hepatoprotective and antioxidant potential against DMBA induced hepatocellular damage in mice that might be due to decreased free radical generation.

  14. Fluorescent mixed ligand copper(II) complexes of anthracene-appended Schiff bases: studies on DNA binding, nuclease activity and cytotoxicity.

    PubMed

    Jaividhya, Paramasivam; Ganeshpandian, Mani; Dhivya, Rajkumar; Akbarsha, Mohammad Abdulkadher; Palaniandavar, Mallayan

    2015-07-14

    A series of mixed ligand copper(ii) complexes of the type [Cu(L)(phen)(ACN)](ClO4)21-5, where L is a bidentate Schiff base ligand (N(1)-(anthracen-10-ylmethylene)-N(2)-methylethane-1,2-diamine (L1), N(1)-(anthracen-10-ylmethylene)-N(2),N(2)-dimethylethane-1,2-diamine (L2), N(1)-(anthracen-10-yl-methylene)-N(2)-ethylethane-1,2-diamine (L3), N(1)-(anthracen-10-ylmethylene)-N(2),N(2)-diethylethane-1,2-diamine (L4) and N(1)-(anthracen-10-ylmethylene)-N(3)-methylpropane-1,3-diamine (L5)) and phen is 1,10-phenanthroline, have been synthesized and characterized by spectral and analytical methods. The X-ray crystal structure of 5 reveals that the coordination geometry around Cu(ii) is square pyramidal distorted trigonal bipyramidal (τ, 0.76). The corners of the trigonal plane of the geometry are occupied by the N2 nitrogen atom of phen, the N4 nitrogen atom of L5 and the N5 nitrogen of acetonitrile while the N1 nitrogen of phen and the N3 nitrogen of L5 occupy the axial positions with an N1-Cu1-N3 bond angle of 176.0(3)°. All the complexes display a ligand field band (600-705 nm) and three less intense anthracene-based bands (345-395 nm) in solution. The Kb values calculated from absorption spectral titration of the complexes (π→π*, 250-265 nm) with Calf Thymus (CT) DNA vary in the order 5 > 4 > 3 > 2 > 1. The fluorescence intensity of the complexes (520-525 nm) decreases upon incremental addition of CT DNA, which reveals the involvement of phen rather than the appended anthracene ring in partial DNA intercalation with the DNA base stack. The extent of quenching is in agreement with the DNA binding affinities and the relative increase in the viscosity of DNA upon binding to the complexes as well. Thus 5 interacts with DNA more strongly than 4 on account of the stronger involvement in hydrophobic DNA interaction of the anthracenyl moiety, which is facilitated by the propylene ligand backbone with chair conformation. The ability of complexes (100 μM) to cleave DNA (p

  15. Driving voltage reduction in white organic light-emitting devices from selectively doping in ambipolar blue-emitting layer

    NASA Astrophysics Data System (ADS)

    Hsiao, Chih-Hung; Lin, Chi-Feng; Lee, Jiun-Haw

    2007-11-01

    White organic light-emitting devices (OLEDs) consisting of ambipolar 9,10-bis(2'-naphthyl) anthracene (ADN) as a host of blue-emitting layer (EML) were investigated. A thin codoped layer of yellow 5,6,11,12-Tetraphenylnaphthacene (rubrene) served as a probe for detecting the position of maximum recombination rate in the 4,4'-bis[2-(4-(N,N-diphenylamino)phenyl)vinyl]biphenyl (DPAVBi) doped-ADN EML. Due to the energy barrier and bipolar carrier transport, the maximum recombination rate was found to be close to but not exactly at the interface of the hole-transporting layer and the EML. With appropriate tuning in the thickness, position, and dopant concentrations of the codoped layer (rubrene:DPAVBi:ADN) in the EML, the device driving voltage decreased by 21.7%, nearly 2 V in reduction, due to the increased recombination current from the faster exciton relaxation induced by the yellow dopants. Among the advantages of introducing the codoped layer over conventional single-doped layers are the elimination of the trapping effect to avoid increasing the device driving voltage, the alleviation of the dependence of the recombination zone on the applied voltage for improving color stability, and the utilization of excitons in a more efficient way to enhance device efficiency. Without using any electrically conductive layers such as the p-i-n structure, we were able to successfully generate 112 cd/m2 at 4 V from our white OLED simply by engineering the structure of the EML.

  16. Enhanced susceptibility of ovaries from obese mice to 7,12-dimethylbenz[a]anthracene-induced DNA damage

    PubMed Central

    Ganesan, Shanthi; Nteeba, Jackson; Keating, Aileen F.

    2014-01-01

    7,12-dimethylbenz[a]anthracene (DMBA) depletes ovarian follicles and induces DNA damage in extra-ovarian tissues, thus, we investigated ovarian DMBA-induced DNA damage. Additionally, since obesity is associated with increased offspring birth defect incidence, we hypothesized that a DMBA-induced DNA damage response (DDR) is compromised in ovaries from obese females. Wild type (lean) non agouti (a/a) and KK.Cg-Ay/J heterozygote (obese) mice were dosed with sesame oil or DMBA (1mg/kg; intraperitoneal injection) at 18 wks of age, for 14 days. Total ovarian RNA and protein were isolated and abundance of Ataxia telangiectasia mutated (Atm), X-ray repair complementing defective repair in chinese hamster cells 6 (Xrcc6), Breast cancer type 1 (Brca1), Rad 51 homolog (Rad51), Poly [ADP-ribose] polymerase 1 (Parp1) and Protein kinase, DNA-activated, catalytic polypeptide (Prkdc) were quantified by RT-PCR or Western blot. Phosphorylated histone H2AX (γH2AX) level was determined by Western blotting. Obesity decreased (P < 0.05) basal protein abundance of PRKDC and BRCA1 proteins but increased (P < 0.05) γH2AX and PARP1 proteins. Ovarian ATM, XRCC6, PRKDC, RAD51 and PARP1 proteins were increased (P < 0.05) by DMBA exposure in lean mice. A blunted DMBA-induced increase (P < 0.05) in XRCC6, PRKDC, RAD51 and BRCA1 was observed in ovaries from obese mice, relative to lean counterparts. Taken together, DMBA exposure induced γH2AX as well as the ovarian DDR, supporting that DMBA causes ovarian DNA damage. Additionally, ovarian DDR was partially attenuated in obese females raising concern that obesity may be an additive factor during chemical-induced ovotoxicity. PMID:25448685

  17. Trianthema portulacastrum Linn. exerts chemoprevention of 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis in rats.

    PubMed

    Bishayee, Anupam; Mandal, Animesh

    2014-10-01

    Due to limited treatment options for advanced-stage metastatic breast cancer, a high priority should be given to develop non-toxic chemopreventive drugs. The value of various natural and dietary agents to reduce the risk of developing breast cancer is well established. Trianthema portulacastrum Linn. (Aizoaceae), a dietary and medicinal plant, has been found to exert antihepatotoxic and antihepatocarcinogenic properties in rodents. This study was initiated to investigate mechanism-based chemopreventive potential of an ethanolic extract of T. portulacastrum (TPE) against 7,12-dimethylbenz(a)anthracene (DMBA)-initiated rat mammary gland carcinogenesis, an experimental tumor model that closely resembles human breast cancer. Rats had access to a basal diet supplemented with TPE to yield three dietary doses of the extract, i.e., 50, 100 and 200 mg/kg body weight. Following two weeks of TPE treatment, mammary tumorigenesis was initiated by oral administration of DMBA (50 mg/kg body weight). At the end of the study (16 weeks after DMBA exposure), TPE exhibited a striking reduction of DMBA-induced mammary tumor incidence, total tumor burden and average tumor weight and reversed intratumor histopathological alterations. TPE dose-dependently suppressed proliferating cell nuclear antigen and cyclin D1 expression, induced apoptosis, upregulated proapoptotic protein Bax, downregulated antiapoptotic protein Bcl-2 and diminished the expression of nuclear and cytosolic β-catenin in mammary tumors. Our results clearly provide the first experimental evidence that TPE exerts chemopreventive effect in the classical DMBA model of breast cancer by suppressing abnormal cell proliferation and inducing apoptosis mediated through alteration of Bax/Bcl-2 ratio. Mechanistically, TPE is capable of diminishing activated canonical Wnt/β-catenin signaling to exhibit antiproliferative, proapoptotic and oncostatic effects during an early-stage breast cancer. These results may encourage further

  18. Adduct formation of 7,12-dimethylbenz(a)anthracene in the embryo of the Japanese medaka (Oryzias latipes)

    SciTech Connect

    Liu, H.; Cooper, K.R.

    1995-12-31

    DNA adduct formation of 7,1 2-dimethylbenz(a)anthracene (DMBA) in vivo in the Japanese medaka embryo were investigated using {sup 32}P-postlabeling analysis. 1-compounds (endogenous adducts) were not observed in the Japanese medaka embryo on days 4 (prior to liver formation), 6 (liver/swim bladder) or 10 (prior to hatch) of development. The level of DMBA:DNA adducts were concentration-dependent over the range of 0.625 ppm (Total Adducts 0.05707 pmol/mg of DNA) to 2.50 ppm (0.43341 pmol/mg of DNA) and decreased at 5.00 ppm (0.25338 pmol/mg of DNA) after medaka embryos were exposed to DMBA for 6 days from the day of fertilization. The decrease in DMBA:DNA adducts at 5.00 ppm was probably due to embryo toxicity (78% death). The level of DMBA:DNA adducts formed from the embryos exposed to DMBA for 24 hr decreased as the stage of development increased: day 4 > day 6 > day 10; 0.0262, 0.0179, 0.0129 pmol/mg of DNA, respectively. The level of DMBA:DNA adducts increased as the length of exposure increased: 4 day < 6 day < 10 day; 0.0233, 0.0614, 0.1502, respectively. There was both a time and dose dependence to the number of adducts detected. The data presented demonstrated the development of DM BA-DNA adducts in the developing Japanese medaka (Oryzias latipes) and the lack of I-compounds.

  19. Effects of selenium on 7,12-dimethylbenz(a)anthracene-induced mammary carcinogenesis and DNA adduct formation

    SciTech Connect

    Ip, C.; Daniel, F.B.

    1985-01-01

    The purpose of the present investigation was to determine the effects of dietary selenium deficiency or excess on 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary neoplasia in rats and to delineate whether selenium-mediated modification of mammary carcinogenesis was associated with changes in carcinogen:DNA adduct formation and activities of liver microsomal enzymes that are involved in xenobiotic metabolism. Female Sprague-Dawley rats were divided into three groups from weaning and were maintained on one of three synthetic diets designated as follows: selenium deficient (less than 0.02 ppm); selenium adequate (0.2 ppm); or selenium excess (2.5 ppm). For the DMBA binding and DNA adduct studies, rats were given a dose of (/sup 3/H)DMBA p.o. after 1 month on their respective diets. Results from the liver and the mammary gland indicated that neither selenium deficiency nor excess had any significant effect on the binding levels, which were calculated on the basis of total radioactivity isolated with the purified DNA. Furthermore, it was found that dietary selenium intake did not seem to affect quantitatively or qualitatively the formation of DMBA:DNA adducts in the liver. Similarly, in a parallel group of rats that did not receive DMBA, the activities of aniline hydroxylase, aminopyrine N-demethylase, and cytochrome c reductase were not significantly altered by dietary selenium levels. Concurrent with the above experiments, the effect of dietary selenium intake on carcinogenesis was also monitored. Results of this experiment indicated that selenium deficiency enhanced mammary carcinogenesis only when this nutritional condition was maintained in the postinitiation phase. Likewise, an excess of selenium intake inhibited neoplastic development only when this regimen was continued after DMBA administration.

  20. Thermal and Optical Modulation of the Carrier Mobility in OTFTs Based on an Azo-anthracene Liquid Crystal Organic Semiconductor.

    PubMed

    Chen, Yantong; Li, Chao; Xu, Xiuru; Liu, Ming; He, Yaowu; Murtaza, Imran; Zhang, Dongwei; Yao, Chao; Wang, Yongfeng; Meng, Hong

    2017-03-01

    One of the most striking features of organic semiconductors compared with their corresponding inorganic counterparts is their molecular diversity. The major challenge in organic semiconductor material technology is creating molecular structural motifs to develop multifunctional materials in order to achieve the desired functionalities yet to optimize the specific device performance. Azo-compounds, because of their special photoresponsive property, have attracted extensive interest in photonic and optoelectronic applications; if incorporated wisely in the organic semiconductor groups, they can be innovatively utilized in advanced smart electronic applications, where thermal and photo modulation is applied to tune the electronic properties. On the basis of this aspiration, a novel azo-functionalized liquid crystal semiconductor material, (E)-1-(4-(anthracen-2-yl)phenyl)-2-(4-(decyloxy)phenyl)diazene (APDPD), is designed and synthesized for application in organic thin-film transistors (OTFTs). The UV-vis spectra of APDPD exhibit reversible photoisomerizaton upon photoexcitation, and the thin films of APDPD show a long-range orientational order based on its liquid crystal phase. The performance of OTFTs based on this material as well as the effects of thermal treatment and UV-irradiation on mobility are investigated. The molecular structure, stability of the material, and morphology of the thin films are characterized by thermal gravimetric analysis (TGA), polarizing optical microscopy (POM), (differential scanning calorimetry (DSC), UV-vis spectroscopy, atomic force microscopy (AFM), and scanning tunneling microscopy (STM). This study reveals that our new material has the potential to be applied in optical sensors, memories, logic circuits, and functional switches.

  1. Enhanced susceptibility of ovaries from obese mice to 7,12-dimethylbenz[a]anthracene-induced DNA damage

    SciTech Connect

    Ganesan, Shanthi Nteeba, Jackson Keating, Aileen F.

    2014-12-01

    7,12-Dimethylbenz[a]anthracene (DMBA) depletes ovarian follicles and induces DNA damage in extra-ovarian tissues, thus, we investigated ovarian DMBA-induced DNA damage. Additionally, since obesity is associated with increased offspring birth defect incidence, we hypothesized that a DMBA-induced DNA damage response (DDR) is compromised in ovaries from obese females. Wild type (lean) non agouti (a/a) and KK.Cg-Ay/J heterozygote (obese) mice were dosed with sesame oil or DMBA (1 mg/kg; intraperitoneal injection) at 18 weeks of age, for 14 days. Total ovarian RNA and protein were isolated and abundance of Ataxia telangiectasia mutated (Atm), X-ray repair complementing defective repair in Chinese hamster cells 6 (Xrcc6), breast cancer type 1 (Brca1), Rad 51 homolog (Rad51), poly [ADP-ribose] polymerase 1 (Parp1) and protein kinase, DNA-activated, catalytic polypeptide (Prkdc) were quantified by RT-PCR or Western blot. Phosphorylated histone H2AX (γH2AX) level was determined by Western blotting. Obesity decreased (P < 0.05) basal protein abundance of PRKDC and BRCA1 proteins but increased (P < 0.05) γH2AX and PARP1 proteins. Ovarian ATM, XRCC6, PRKDC, RAD51 and PARP1 proteins were increased (P < 0.05) by DMBA exposure in lean mice. A blunted DMBA-induced increase (P < 0.05) in XRCC6, PRKDC, RAD51 and BRCA1 was observed in ovaries from obese mice, relative to lean counterparts. Taken together, DMBA exposure induced γH2AX as well as the ovarian DDR, supporting that DMBA causes ovarian DNA damage. Additionally, ovarian DDR was partially attenuated in obese females raising concern that obesity may be an additive factor during chemical-induced ovotoxicity. - Highlights: • DMBA induces markers of ovarian DNA damage. • Obesity induces low level ovarian DNA damage. • DMBA-induced DNA repair response is altered by obesity.

  2. Stereoselective metabolism of dibenz(a,h)anthracene to trans-dihydrodiols and their activation to bacterial mutagens.

    PubMed Central

    Platt, K L; Schollmeier, M; Frank, H; Oesch, F

    1990-01-01

    Dibenz(a,h)anthracene (DBA), a carcinogenic, polycyclic aromatic hydrocarbon ubiquitous in the environment, is metabolized by the hepatic microsomal fraction of immature Sprague-Dawley rats pretreated with Aroclor 1254 to 27 ethyl acetate-extractable metabolites. More than half of these metabolites (51%) consisted of trans-1,2-; -3,4-; and -5,6-dihydrodiols including their identified secondary metabolites. The three trans-dihydrodiols (4.9, 15.8, and 0.6% of total metabolic conversion) were highly enriched in their R,R enantiomers (85, 71, and 98%) as determined by high performance liquid chromatography on suitable chiral stationary phases. This is explained on the basis of the stereoselective epoxidation of DBA by cytochrome P-450c (induced by Aroclor 1254) followed by regioselective hydration catalyzed by microsomal epoxide hydrolase. Determination of the bacterial mutagenicity by measuring the reversion rate of histidine-dependent Salmonella typhimurium TA100 to histidine prototrophy revealed marked differences in the mutagenicity of the enantiomers of the trans-dihydrodiols of DBA when activated by the same metabolizing system as used in the metabolism studies. In the case of trans-1,2- and -5,6-dihydrodiol, the S,S enantiomers were converted to more mutagenic metabolites than their corresponding optical antipodes, whereas in the case of trans-3,4-dihydrodiol it was the R,R enantiomer that produced the stronger mutagens. Therefore, both regio- and stereoselectivity of the metabolizing enzymes attribute to the dominant role of trans-3,4-dihydrodiol in the mutagenicity of DBA. PMID:2272331

  3. Caribbean yellow band disease compromises the activity of catalase and glutathione S-transferase in the reef-building coral Orbicella faveolata exposed to anthracene.

    PubMed

    Montilla, Luis Miguel; Ramos, Ruth; García, Elia; Cróquer, Aldo

    2016-05-03

    Healthy and diseased corals are threatened by different anthropogenic sources, such as pollution, a problem expected to become more severe in the near future. Despite the fact that coastal pollution and coral diseases might represent a serious threat to coral reef health, there is a paucity of controlled experiments showing whether the response of diseased and healthy corals to xenobiotics differs. In this study, we exposed healthy and Caribbean yellow band disease (CYBD)-affected Orbicella faveolata colonies to 3 sublethal concentrations of anthracene to test if enzymatic responses to this hydrocarbon were compromised in CYBD-affected tissues. For this, a 2-factorial fully orthogonal design was used in a controlled laboratory bioassay, using tissue condition (2 levels: apparently healthy and diseased) and pollutant concentration (4 levels: experimental control, 10, 30 and 100 ppb concentration) as fixed factors. A permutation-based ANOVA (PERMANOVA) was used to test the effects of condition and concentration on the specific activity of 3 enzymatic biomarkers: catalase, glutathione S-transferase, and glutathione peroxidase. We found a significant interaction between the concentration of anthracene and the colony condition for catalase (Pseudo-F = 3.84, df = 3, p < 0.05) and glutathione S-transferase (Pseudo-F = 3.29, df = 3, p < 0.05). Moreover, our results indicated that the enzymatic response to anthracene in CYBD-affected tissues was compromised, as the activity of these enzymes decreased 3- to 4-fold compared to healthy tissues. These results suggest that under a potential scenario of increasing hydrocarbon coastal pollution, colonies of O. faveolata affected with CYBD might become more vulnerable to the deleterious effects of chemical pollution.

  4. Recyclable nanoscale zero-valent iron-based magnetic polydopamine coated nanomaterials for the adsorption and removal of phenanthrene and anthracene

    PubMed Central

    Li, Jing; Zhou, Qingxiang; Liu, Yongli; Lei, Man

    2017-01-01

    Abstract In this study, nanoscale zero-valent iron nanoparticles (NZVIs) were coated with silica and polydopamine using a two-step process. The coated nanoparticles were applied as adsorbents for removal of two common polycyclic aromatic hydrocarbons pollutants, phenanthrene (PHE) and anthracene (ANT) from aqueous system. Adsorption kinetics followed a pseudo-second-order model. Isotherms and thermodynamics were investigated and the results indicated that the adsorption process fit best to the Freundlich model and exhibited the characteristics of an exothermal physical adsorption process. Owing to their superparamagnetic characteristics and stability, these adsorbents could be easily collected and recycled for reuse. PMID:28179954

  5. Hormone dependency of chromosome aberrations induced by 7,12-dimethylbenz(a)anthracene in rat bone marrow cells: site-specific increase by erythropoietin

    SciTech Connect

    Ueda, N.; Suglyama, T.; Chattopadhyay, S.C.; Goto-Mimura, K.; Maeda, S.

    1981-08-01

    The frequency of chromosome aberrations (CA) 6 hours after iv injection of 50 mg 7,12-dimethylbenz(a)anthracene (DMBA0/kg was studied in bone marrow cells of the noninbred Long-Evans rat under various hematopoietic conditions. The percentage of metaphase cells with CA was enhanced by anemia and suppressed by polycythemia. The low incidence of CA in polycythemic rats was reversed by 6 U of sheep erythropoietin (EP) injected at the time of DMBA treatment. The interchromosomal and intrachromosomal distribution of CA indicated that hematopoietic stimuli, more specifically EP, greatly enhanced DMBA-induced CA in specific chromosomal regions.

  6. Supramolecular Self-Assembly of Histidine-Capped-Dialkoxy-Anthracene: A Visible-Light-Triggered Platform for Facile siRNA Delivery.

    PubMed

    Patil, Sachin P; Moosa, Basem A; Alsaiari, Shahad; Alamoudi, Kholod; Alshamsan, Aws; AlMalik, Abdulaziz; Adil, Karim; Eddaoudi, Mohamed; Khashab, Niveen M

    2016-09-19

    Supramolecular self-assembly of histidine-capped-dialkoxy-anthracene (HDA) results in the formation of light-responsive nanostructures. Single-crystal X-ray diffraction analysis of HDA shows two types of hydrogen bonding. The first hydrogen bond is established between the imidazole moieties while the second involves the oxygen atom of one amide group and the hydrogen atom of a second amide group. When protonated in acidic aqueous media, HDA successfully complexes siRNA yielding spherical nanostructures. This biocompatible platform controllably delivers siRNA with high efficacy upon visible-light irradiation leading up to 90 % of gene silencing in live cells.

  7. Theoretical study of the electronically excited radical cations of naphthalene and anthracene as archetypal models for astrophysical observations. Part II. Dynamics consequences.

    PubMed

    Ghanta, S; Reddy, V Sivaranjana; Mahapatra, S

    2011-08-28

    Nuclear dynamics is investigated theoretically from first principles by employing the ab initio vibronic models of the prototypical naphthalene and anthracene radical cations developed in Part I. This Part is primarily aimed at corroborating a large amount of available experimental data with a specific final goal to establish an unambiguous link with the current observations in astrophysics and astronomy. The detailed analyses presented here perhaps establish that these two prototypical polycyclic aromatic hydrocarbon radical cations are indeed potential carriers of the observed diffuse interstellar bands.

  8. [Suppressor activity of bone marrow and spleen cells in C57Bl/6 mice during carcinogenesis induced by 7,12-dimethylbenz(a)anthracene].

    PubMed

    Kusmartsev, S A; Ogreba, V I

    1989-01-01

    The nonspecific suppressor activity of bone marrow cells (BMC) and spleen cells (SC) of C57B1/6 mice was studied at 7,12-dimethylbenz(a)anthracene-induced carcinogenesis. It is established that in the latent period of the tumour development and with its appearance the suppressor activity of BMC decreases, while SC-increases. The activity of the BMC suppressor factor which is determined by the inhibition of proliferation of mastocytoma P-815 cells in vitro did not change significantly.

  9. Carcinogen 7,12-dimethylbenz[a]anthracene-induced mammary tumorigenesis is accelerated in Smad3 heterozygous mice compared to Smad3 wild type mice

    PubMed Central

    Liu, Zhengxue; Kundu-Roy, Tanima; Matsuura, Isao; Wang, Guannan; Lin, Yong; Lou, You-Rong; Barnard, Nicola J.; Wang, Xiao-Fan; Huang, Mou-Tuan; Suh, Nanjoo; Liu, Fang

    2016-01-01

    Previous studies based on cell culture and xenograft animal models suggest that Smad3 has tumor suppressor function for breast cancer during early stages of tumorigenesis. In this report, we show that DMBA (7,12-dimethylbenz[a]anthracene), a chemical carcinogen, induces mammary tumor formation at a significantly higher frequency in the Smad3 heterozygous mice than in the Smad3 wild type mice. This is the first genetic evidence showing that Smad3 inhibits mammary tumor formation in a mouse model. Our findings support the notion that Smad3 has important tumor suppressor function for breast cancer. PMID:27588495

  10. Haloalkalitolerant Actinobacteria with capacity for anthracene degradation isolated from soils close to areas with oil activity in the State of Veracruz, Mexico.

    PubMed

    Lara-Severino, Reyna Del C; Camacho-López, Miguel A; Casanova-González, Edgar; Gómez-Oliván, Leobardo M; Sandoval-Trujillo, Ángel H; Isaac-Olivé, Keila; Ramírez-Durán, Ninfa

    2016-03-01

    The use of native strains of microorganisms from soils is an excellent option for bioremediation. To our knowledge, until now there has been no other group working on the isolation of Actinobacteria from contaminated soils in Mexico. In this study, samples of soils close to areas with oil activity in the State of Veracruz, Mexico, were inoculated for the isolation of Actinobacteria. The strains isolated were characterized morphologically, and the concentrations of NaCl and pH were determined for optimal growth. Strain selection was performed by the detection of a phylogenetic marker for Actinobacteria located at the 23S rRNA gene, followed by species identification by sequencing the 16S rRNA gene. Several haloalkalitolerant Actinobacteria were isolated and identified as: Kocuria rosea, K. palustris, Microbacterium testaceum, Nocardia farcinica and Cellulomonas denverensis. Except for C. denverensis, the biomass of all strains increased in the presence of anthracene. The strains capacity to metabolize anthracene (at 48 h), determined by fluorescence emission, was in the range of 46-54%. During this time, dihydroxy aromatic compounds formed, characterized by attenuated total reflectance Fourier transform infrared spectroscopy bands of 1205 cm-1 and 1217 cm-1. Those Actinobacteria are potentially useful for the bioremediation of saline and alkaline environments contaminated with polycyclic aromatic hydrocarbon compounds. [Int Microbiol 2016; 19(1):15-26].

  11. Full-dimensional multilayer multiconfigurational time-dependent Hartree study of electron transfer dynamics in the anthracene/C60 complex.

    PubMed

    Xie, Yu; Zheng, Jie; Lan, Zhenggang

    2015-02-28

    Electron transfer at the donor-acceptor heterojunctions plays a critical role in the photoinduced process during the solar energy conversion in organic photovoltaic materials. We theoretically investigate the electron transfer process in the anthracene/C60 donor-acceptor complex by using quantum dynamics calculations. The electron-transfer model Hamiltonian with full dimensionality was built by quantum-chemical calculations. The quantum dynamics calculations were performed using the multiconfigurational time-dependent Hartree (MCTDH) theory and multilayer (ML) MCTDH methods. The latter approach (ML-MCTDH) allows us to conduct the comprehensive study on the quantum evolution of the full-dimensional electron-transfer model including 4 electronic states and 246 vibrational degrees of freedom. Our quantum dynamics calculations exhibit the ultrafast anthracene → C60 charge transfer process because of the strong coupling between excitonic and charge transfer states. This work demonstrates that the ML-MCTDH is a very powerful method to treat the quantum evolution of complex systems.

  12. Determination of the Residual Anthracene Concentration in Cultures of Haloalkalitolerant Actinomycetes by Excitation Fluorescence, Emission Fluorescence, and Synchronous Fluorescence: Comparative Study.

    PubMed

    Lara-Severino, Reyna Del Carmen; Camacho-López, Miguel Ángel; García-Macedo, Jessica Marlene; Gómez-Oliván, Leobardo M; Sandoval-Trujillo, Ángel H; Isaac-Olive, Keila; Ramírez-Durán, Ninfa

    2016-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are compounds that can be quantified by fluorescence due to their high quantum yield. Haloalkalitolerant bacteria tolerate wide concentration ranges of NaCl and pH. They are potentially useful in the PAHs bioremediation of saline environments. However, it is known that salinity of the sample affects fluorescence signal regardless of the method. The objective of this work was to carry out a comparative study based on the sensitivity, linearity, and detection limits of the excitation, emission, and synchronous fluorescence methods, during the quantification of the residual anthracene concentration from the following haloalkalitolerant actinomycetes cultures Kocuria rosea, Kocuria palustris, Microbacterium testaceum, and 4 strains of Nocardia farcinica, in order to establish the proper fluorescence method to study the PAHs biodegrading capacity of haloalkalitolerant actinobacteria. The study demonstrated statistical differences among the strains and among the fluorescence methods regarding the anthracene residual concentration. The results showed that excitation and emission fluorescence methods performed very similarly but sensitivity in excitation fluorescence is slightly higher. Synchronous fluorescence using Δλ = 150 nm is not the most convenient method. Therefore we propose the excitation fluorescence as the fluorescence method to be used in the study of the PAHs biodegrading capacity of haloalkalitolerant actinomycetes.

  13. Determination of the Residual Anthracene Concentration in Cultures of Haloalkalitolerant Actinomycetes by Excitation Fluorescence, Emission Fluorescence, and Synchronous Fluorescence: Comparative Study

    PubMed Central

    Lara-Severino, Reyna del Carmen; Camacho-López, Miguel Ángel; García-Macedo, Jessica Marlene; Gómez-Oliván, Leobardo M.; Sandoval-Trujillo, Ángel H.; Isaac-Olive, Keila; Ramírez-Durán, Ninfa

    2016-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are compounds that can be quantified by fluorescence due to their high quantum yield. Haloalkalitolerant bacteria tolerate wide concentration ranges of NaCl and pH. They are potentially useful in the PAHs bioremediation of saline environments. However, it is known that salinity of the sample affects fluorescence signal regardless of the method. The objective of this work was to carry out a comparative study based on the sensitivity, linearity, and detection limits of the excitation, emission, and synchronous fluorescence methods, during the quantification of the residual anthracene concentration from the following haloalkalitolerant actinomycetes cultures Kocuria rosea, Kocuria palustris, Microbacterium testaceum, and 4 strains of Nocardia farcinica, in order to establish the proper fluorescence method to study the PAHs biodegrading capacity of haloalkalitolerant actinobacteria. The study demonstrated statistical differences among the strains and among the fluorescence methods regarding the anthracene residual concentration. The results showed that excitation and emission fluorescence methods performed very similarly but sensitivity in excitation fluorescence is slightly higher. Synchronous fluorescence using Δλ = 150 nm is not the most convenient method. Therefore we propose the excitation fluorescence as the fluorescence method to be used in the study of the PAHs biodegrading capacity of haloalkalitolerant actinomycetes. PMID:26925294

  14. Novel fluorescent anthracene-bodipy dyads displaying sensitivity to pH and turn-on behaviour towards Cu(ii) ions.

    PubMed

    Vanessa Saura, A; Isabel Burguete, M; Galindo, Francisco; Luis, Santiago V

    2017-04-05

    Three bichromophoric compounds containing anthracene and bodipy moieties connected by different spacers have been synthesized and fully characterized. The set of spacers comprises a variety of bridges (short and flexible 1,2-diaminoethane in compound 1a, long and flexible 1,8-diaminooctane in compound 1b and short and rigid piperazine in compound 1c). The new compounds show interchromophoric communication via Electronic Energy Transfer (EET). When anthracene is excited, the energy is efficiently transferred to the bodipy moiety. The emission of the acceptor is partially quenched in dyad 1a but remarkably not in 1b and 1c. In an aqueous environment, the fluorescence of the new compounds display sensitivity to pH (emissive at acidic values and non-emissive at neutral ones), a typical behaviour of photoinduced electron-transfer (PET) probes, but with remarkable differences in the pKa of each compound, attributable to the nature of the linker. Additionally, the behaviour in the presence of several metallic cations (Cu(2+), Ni(2+), Cd(2+), Zn(2+)) has been studied, and a turn-on response towards Cu(2+) in water at neutral pH has been found.

  15. 7,12-Dimethylbenz[a]anthracene exposure induces the DNA repair response in neonatal rat ovaries

    SciTech Connect

    Ganesan, Shanthi Bhattacharya, Poulomi Keating, Aileen F.

    2013-11-01

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all stages of development. This study investigated DMBA-induced DNA double strand break (DSB) formation with subsequent activation of the ovarian DNA repair response in models of pre-antral or pre-ovulatory follicle loss. Postnatal day (PND) 4 Fisher 344 (F344) rat ovaries were cultured for 4 days followed by single exposures of vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and maintained in culture for 4 or 8 days. Alternately, PND4 F344 rat ovaries were exposed to 1 μM DMBA at the start of culture for 2 days. Total RNA or protein was isolated, followed by qPCR or Western blotting to quantify mRNA or protein level, respectively. γH2AX and phosphorylated ATM were localized and quantified using immunofluorescence staining. DMBA exposure increased caspase 3 and γH2AX protein. Additionally, DMBA (12.5 nM and 1 μM) increased levels of mRNA encoding Atm, Xrcc6, Brca1 and Rad51. In contrast, Parp1 mRNA was decreased on d4 and increased on d8 of DMBA exposure, while PARP1 protein increased after 8 days of DMBA exposure. Total ATM increased in a concentration-dependent temporal pattern (75 nM d4; 12.5 nM d8), while pATM was localized in large primary and secondary follicles and increased after 8 days of 75 nM DMBA exposure compared to both control and 12.5 nM DMBA. These findings support that, despite some concentration effects, DMBA induces ovarian DNA damage and that DNA repair mechanisms are induced as a potential mechanism to prevent follicle loss. - Highlights: • DMBA exposure increases ovarian caspase-3 protein expression. • DMBA exposure increases the γH2AX protein in oocytes. • DMBA exposure activates a DNA repair response in the ovary.

  16. Protective role for ovarian glutathione S-transferase isoform pi during 7,12-dimethylbenz[a]anthracene-induced ovotoxicity

    SciTech Connect

    Bhattacharya, Poulomi Keating, Aileen F.

    2012-04-15

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles at all developmental stages. This study investigated a role for the glutathione S-transferase (Gst) isoforms alpha (a), mu (m) and pi (p) and the transcription factors, Ahr and Nrf2, during DMBA-induced ovotoxicity, and their regulation by phosphatidylinositol-3 kinase (PI3K) signaling. Negative regulation of JNK by GSTP during DMBA exposure was also studied. Post-natal day (PND) 4 Fischer 344 rat ovaries were exposed to vehicle control (1% DMSO) ± DMBA (1 μM) or vehicle control (1% DMSO) ± LY294002 (PI3K inhibitor; 20 μM) for 1, 2, 4, or 6 days. Total RNA or protein was isolated, followed by RT-PCR or Western blotting to determine mRNA or protein level, respectively. Immunoprecipitation using an anti-GSTP antibody was performed to determine interaction between GSTP and JNK, followed by Western blotting to determine JNK and p-c-Jun protein level. DMBA had no impact on Gsta, Gstm or Nrf2 mRNA level, but increased Gstp mRNA and protein after 2 days. Ahr mRNA and protein increased after 2 and 4 days of DMBA exposure, respectively and DMBA increased NRF2 protein level after 4 days. JNK bound to GSTP was increased during DMBA exposure, with a concomitant decrease in unbound JNK and p-c-Jun. Ahr and Gstp mRNA were decreased (2 days) and increased (4 days) by PI3K inhibition, while Gstm mRNA increased (P < 0.05) after both time points, and there was no effect on Nrf2 mRNA. PI3K inhibition increased AHR, NRF2 and GSTP protein level. These findings support involvement of ovarian GSTP during DMBA exposure, and indicate a regulatory role for the PI3K signaling pathway on ovarian xenobiotic metabolism gene expression. -- Highlights: ► Ovarian GSTP is activated in response to DMBA exposure. ► AhR and Nrf2 transcription factors are up-regulated by DMBA. ► PI3K signaling regulates Ahr, Nrf2 and Gstp expression. ► GSTP negatively regulates ovarian JNK in response to DMBA exposure.

  17. Impact of 7,12-dimethylbenz[a]anthracene exposure on connexin gap junction proteins in cultured rat ovaries

    SciTech Connect

    Ganesan, Shanthi Keating, Aileen F.

    2014-01-15

    7,12-Dimethylbenz[a]anthracene (DMBA) destroys ovarian follicles in a concentration-dependent manner. The impact of DMBA on connexin (CX) proteins that mediate communication between follicular cell types along with pro-apoptotic factors p53 and Bax were investigated. Postnatal day (PND) 4 Fisher 344 rat ovaries were cultured for 4 days in vehicle medium (1% DMSO) followed by a single exposure to vehicle control (1% DMSO) or DMBA (12.5 nM or 75 nM) and cultured for 4 or 8 days. RT-PCR was performed to quantify Cx37, Cx43, p53 and Bax mRNA level. Western blotting and immunofluorescence staining were performed to determine CX37 or CX43 level and/or localization. Cx37 mRNA and protein increased (P < 0.05) at 4 days of 12.5 nM DMBA exposure. Relative to vehicle control-treated ovaries, mRNA encoding Cx43 decreased (P < 0.05) but CX43 protein increased (P < 0.05) at 4 days by both DMBA exposures. mRNA expression of pro-apoptotic p53 was decreased (P < 0.05) but no changes in Bax expression were observed after 4 days of DMBA exposures. In contrast, after 8 days, DMBA decreased Cx37 and Cx43 mRNA and protein but increased both p53 and Bax mRNA levels. CX43 protein was located between granulosa cells, while CX37 was located at the oocyte cell surface of all follicle stages. These findings support that DMBA exposure impacts ovarian Cx37 and Cx43 mRNA and protein prior to both observed changes in pro-apoptotic p53 and Bax and follicle loss. It is possible that such interference in follicular cell communication is detrimental to follicle viability, and may play a role in DMBA-induced follicular atresia. - Highlights: • DMBA increases Cx37 and Cx43 expression prior to follicle loss. • During follicle loss both Cx37 and Cx43 expressions are reduced. • CX43 protein is absent in follicle remnants lacking an oocyte.

  18. Crystal structure of (E)-N 1-[(anthracen-9-yl)methyl­idene]-N 4-phenyl­benzene-1,4-di­amine

    PubMed Central

    Ahmad, Musheer; Golenya, Irina A.

    2017-01-01

    The title compound, C27H20N2, a Schiff base synthesized via a condensation reaction between anthracene-9-carbaldehyde and N-phenyl-p-phenyl­enedi­amine, crystallizes with three independent mol­ecules in the asymmetric unit. The three mol­ecules have slightly varying overall conformations, all having trans conformations with respect to the C=N bond. In the crystal, the packing features N—H⋯N hydrogen bonds, which connect mol­ecules into chains extending along the c-axis direction, inter­linked by C—H⋯π inter­actions (minimum H⋯Cg = 2.65 Å) into sheets lying parallel to (001). PMID:28217328

  19. Anthracene/phenothiazine π-conjugated sensitizers for dye-sensitized solar cells using redox mediator in organic and water-based solvents.

    PubMed

    Lin, Ryan Yeh-Yung; Chuang, Tzu-Man; Wu, Feng-Ling; Chen, Pei-Yu; Chu, Te-Chun; Ni, Jen-Shyang; Fan, Miao-Syuan; Lo, Yih-Hsing; Ho, Kuo-Chuan; Lin, Jiann T

    2015-01-01

    Metal-free dyes (MD1 to MD5) containing an anthracene/phenothiazine unit in the spacer have been synthesized. The conversion efficiency (7.13 %) of the dye-sensitized solar cell using MD3 as the sensitizer reached approximately 85 % of the N719-based standard cell (8.47 %). The cell efficiency (8.42 %) of MD3-based dye-sensitized solar cells (DSSCs) with addition of chenodeoxycholic acid is comparable with that of N719-based standard cell. The MD3 water-based DSSCs using a dual-TEMPO (2,2,6,6-tetramethylpiperidine-N-oxyl)/iodide electrolyte exhibited very promising cell performance of 4.96 % with an excellent Voc of 0.77 V.

  20. Effect of Cuscuta chinensis water extract on 7,12-dimethylbenz[a]anthracene-induced skin papillomas and carcinomas in mice.

    PubMed

    Nisa, M; Akbar, S; Tariq, M; Hussain, Z

    1986-10-01

    Cuscuta chinensis, known as Aftimun, is reputed to have antitumour activity in the Unani system of medicine in India. The effect of a hot water extract of C. chinensis on 7,12-dimethylbenz[a]anthracene (DMBA)-induced skin papillomas and carcinomas in Swiss albino mice was studied. Oral administration of the extract (1 g/kg body wt) thrice a week in 22 mice, started on the tenth day after the first application of DMBA to the 252nd day, markedly delayed the appearance and retarded the growth of papillomas and the incidence of carcinoma, relative to a control group with 28 mice, in a two-stage system of tumorigenesis. Its prophylactic effect was found to be statistically significant.

  1. Electron momentum distribution and singlet-singlet annihilation in the organic anthracene molecular crystals using positron 2D-ACAR and fluorescence spectroscopy.

    PubMed

    Selvakumar, Sellaiyan; Sivaji, Krishnan; Arulchakkaravarthi, Arjunan; Sankar, Sambasivam

    2014-08-14

    We present the mapping of electron momentum distribution (EMD) in a single crystal of anthracene by two-dimensional angular correlation of positron annihilation radiation (2D-ACAR). The projected EMD is explained on the basis of the crystallographic features of the material. The EMD spectra provide information about the positron states and their behavior and also about the hindrance of the positronium (Ps) formation in this material. The EMD has exhibited evidence for the absence of free volume defects. The characteristic EMD features regarding the delocalized electronic states are explained. Further, scintillation characteristics such as fluorescence and time-correlated single photon counting have also been studied. The emission peaks are attributed to vibrational bands of fluorescence emission from the singlet excitons and lifetime components are observed to be due to singlet fission and the singlet-singlet excitons annihilation.

  2. Analysis of the near-edge X-ray-absorption fine-structure of anthracene: A combined theoretical and experimental study

    SciTech Connect

    Klues, Michael; Witte, Gregor; Hermann, Klaus

    2014-01-07

    The near-edge fine structure of the carbon K-edge absorption spectrum of anthracene was measured and theoretically analyzed by density functional theory calculations implemented in the StoBe code. It is demonstrated that the consideration of electronic relaxation of excited states around localized core holes yields a significant improvement of the calculated excitation energies and reproduces the experimentally observed fine structure well. The detailed analysis of excitation spectra calculated for each symmetry inequivalent excitation center allows in particular to examine the influence of chemical shifts and core hole effects on the excitation energies. Moreover, the visualization of final states explains the large variations in the oscillator strength of various transitions as well as the nature of Rydberg-states that exhibit a notable density of states below the ionization potentials.

  3. Effect of Side Chains on Molecular Conformation of Anthracene-Ethynylene-Phenylene-Vinylene Oligomers: A Comparative Density Functional Study With and Without Dispersion Interaction.

    PubMed

    Dong, Chuanding; Hoppe, Harald; Beenken, Wichard J D

    2016-06-02

    Using density functional calculations with and without dispersion interaction, we studied the effects of linear octyl and branched 2-ethylhexyl side chains on the oligomer conformation of the conjugated copolymer poly(p-anthracene-ethynylene)-alt-poly(p-phenylene-vinylene). With dispersion included, the branched side chains can cause significant bending of the oligomer backbone, while without dispersion they induce mainly torsional disorder. The oligomers with mainly linear side chains keep good planarity when optimized with and without dispersion. Despite their dramatically different conformations, the calculated absorption spectra of the oligomers with various side chain combinations are very similar, indicating that the conformation of the copolymer is not the main reason for the experimentally observed different spectra of ordered and disordered phases.

  4. Anthracene-9, 10-dione derivatives induced apoptosis in human cervical cancer cell line (CaSki) by interfering with HPV E6 expression.

    PubMed

    Sangthong, Supranee; Sangphech, Naunpun; Palaga, Tanapat; Ngamrojanavanich, Nattaya; Puthong, Songchan; Vilaivan, Tirayut; Muangsin, Nongnuj

    2014-04-22

    A new series of anthracene-9, 10-dione derivatives have been synthesized to increase cytotoxic activity against human papillomavirus (HPV) positive cancer cell line, CaSki. The highest cytotoxicity was achieved by 4-(benzylamino)-9,10-dioxo-4a,9,9a,10-tetrahydroanthracen-1-yl 4-ethylbenzenesulfonate (5) with the inhibitory concentration 50 (IC50) of 0.3 μM which is 20 times lower than that of cisplatin (CDDP; IC50 = 8.0 μM). The toxicity against non-cancerous cell line, WI-38, was low with the IC50 > 10 μM. Treatment with this compound resulted in decreasing HPV E6 expression. Furthermore, increasing p53 and decreasing Bcl-2 expression were noted. Cell cycle profiles revealed an accumulation of cells in the G2/M phase.

  5. A new fluorescent enhanced probe based on (E)-9-(2-nitrovinyl)-anthracene for the detection of bisulfite anions and its practical application

    NASA Astrophysics Data System (ADS)

    Chao, Jianbin; Liu, Yuhong; Zhang, Yan; Zhang, Yongbin; Huo, Fangjun; Yin, Caixia; Wang, Yu; Qin, Liping

    2015-07-01

    A new fluorescent enhanced probe based on (E)-9-(2-nitrovinyl)-anthracene is developed, which shows high selectivity and sensitivity for the detection of bisulfite anions at Na2HPO4 citric acid buffer solutions (pH 5.0). When addition of HSO3-, the fluorescence intensity is significantly enhanced and the probe displays apparent fluorescence color changes from non-fluorescence to blue under a UV lamp illumination, the solution color also changes from yellow to colorless. The detection limit is determined to be as low as 6.30 μM. This offers another specific colorimetric and fluorescent probe for bisulfite anions detection, furthermore it is applied in detecting the level of bisulfite in sugar samples.

  6. High-efficiency blue electroluminescence based on coumarin derivative 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin.

    PubMed

    Zhang, Hui; Chai, Haifang; Yu, Tianzhi; Zhao, Yuling; Fan, Duowang

    2012-11-01

    The electroluminescent (EL) properties of a new coumarin derivative, 3-(4-(anthracen-10-yl)phenyl)-benzo[5,6]coumarin (APBC), were investigated. The results show that the EL devices comprised of vacuum vapor-deposited films using the derivative as dopant exhibited blue emission that is identical to the photoluminescence of the thin film. The electroluminescence device of ITO/2-TNATA (5 nm)/NPB (40 nm)/CBP : APBC (1.0 wt%, 30 nm)/PBD (30 nm)/LiF (1 nm)/Al (100 nm) gives a maximum luminous efficiency of 2.3 cd/A at the current density of 20 mA/cm(2), and maximum luminance of 5169 cd/m(2) at 16 V. The external quantum efficiency of the device is 1.85 %.

  7. Antiproliferative and Apoptotic Effects of Shemamruthaa, a Herbal Preparation, in 7,12-Dimethylbenz(a)Anthracene-Induced Breast Cancer Rats.

    PubMed

    Purushothaman, Ayyakkannu; Nandhakumar, Elumalai; Shanthi, Palanivelu; Sachidanandam, Thiruvaiyaru Panchanatham

    2015-10-01

    A herbal preparation, Shemamruthaa (SM), was formulated to investigate the molecular mechanism by which it exhibits anticancer effects in mammary carcinoma bearing rats. Female Sprague-Dawley rats were used for the study, and mammary carcinoma was induced by administration of 7,12-dimethylbenz(a)anthracene, intragastrically. After 3 months of induction period, the rats were treated with SM (400 mg/kg body weight) for 14 days. Our study shows that SM-treated mammary carcinoma rats showed regression in tumor volume with concomitant increase in p(53), Bax, caspase-3, and caspase-9 mRNA and protein levels compared with mammary carcinoma-induced rats. Proliferating cell nuclear antigen and anti-apoptotic Bcl-2 were markedly increased in mammary carcinoma-induced rats, whereas the SM treatment significantly decreased the expression of these proteins. The expression pattern of apoptotic signaling molecules analyzed in the present study signifies the therapeutic efficacy of SM against breast cancer.

  8. Vertical and adiabatic excitations in anthracene from quantum Monte Carlo: Constrained energy minimization for structural and electronic excited-state properties in the JAGP ansatz.

    PubMed

    Dupuy, Nicolas; Bouaouli, Samira; Mauri, Francesco; Sorella, Sandro; Casula, Michele

    2015-06-07

    We study the ionization energy, electron affinity, and the π → π(∗) ((1)La) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed on molecular orbitals (MOs). The MO-based JAGP ansatz allows one to rigorously treat electron transitions, such as the HOMO → LUMO one, which underlies the (1)La excited state. We present a QMC optimization scheme able to preserve the rank of the antisymmetrized geminal power matrix, thanks to a constrained minimization with projectors built upon symmetry selected MOs. We show that this approach leads to stable energy minimization and geometry relaxation of both ground and excited states, performed consistently within the correlated QMC framework. Geometry optimization of excited states is needed to make a reliable and direct comparison with experimental adiabatic excitation energies. This is particularly important in π-conjugated and polycyclic aromatic hydrocarbons, where there is a strong interplay between low-lying energy excitations and structural modifications, playing a functional role in many photochemical processes. Anthracene is an ideal benchmark to test these effects. Its geometry relaxation energies upon electron excitation are of up to 0.3 eV in the neutral (1)La excited state, while they are of the order of 0.1 eV in electron addition and removal processes. Significant modifications of the ground state bond length alternation are revealed in the QMC excited state geometry optimizations. Our QMC study yields benchmark results for both geometries and energies, with values below chemical accuracy if compared to experiments, once zero point energy effects are taken into account.

  9. Vertical and adiabatic excitations in anthracene from quantum Monte Carlo: Constrained energy minimization for structural and electronic excited-state properties in the JAGP ansatz

    SciTech Connect

    Dupuy, Nicolas; Bouaouli, Samira; Mauri, Francesco Casula, Michele; Sorella, Sandro

    2015-06-07

    We study the ionization energy, electron affinity, and the π → π{sup ∗} ({sup 1}L{sub a}) excitation energy of the anthracene molecule, by means of variational quantum Monte Carlo (QMC) methods based on a Jastrow correlated antisymmetrized geminal power (JAGP) wave function, developed on molecular orbitals (MOs). The MO-based JAGP ansatz allows one to rigorously treat electron transitions, such as the HOMO → LUMO one, which underlies the {sup 1}L{sub a} excited state. We present a QMC optimization scheme able to preserve the rank of the antisymmetrized geminal power matrix, thanks to a constrained minimization with projectors built upon symmetry selected MOs. We show that this approach leads to stable energy minimization and geometry relaxation of both ground and excited states, performed consistently within the correlated QMC framework. Geometry optimization of excited states is needed to make a reliable and direct comparison with experimental adiabatic excitation energies. This is particularly important in π-conjugated and polycyclic aromatic hydrocarbons, where there is a strong interplay between low-lying energy excitations and structural modifications, playing a functional role in many photochemical processes. Anthracene is an ideal benchmark to test these effects. Its geometry relaxation energies upon electron excitation are of up to 0.3 eV in the neutral {sup 1}L{sub a} excited state, while they are of the order of 0.1 eV in electron addition and removal processes. Significant modifications of the ground state bond length alternation are revealed in the QMC excited state geometry optimizations. Our QMC study yields benchmark results for both geometries and energies, with values below chemical accuracy if compared to experiments, once zero point energy effects are taken into account.

  10. Organ-specific distribution of 7-chlorinated benz[a]anthracene and regulation of selected cytochrome P450 genes in rats.

    PubMed

    Sakakibara, Hiroyuki; Ohura, Takashi; Kido, Taketoshi; Yamanaka, Noriko; Tanimura, Nobuhiko; Shimoi, Kayoko; Guruge, Keerthi S

    2013-02-01

    We previously reported that 14-day exposure to 7-chlorinated benz[a]anthracene (7-Cl-BaA), a new environmental pollutant, selectively induced hepatic cytochrome P450 (CYP)1A2 in rats, although treatment with its parent, benz[a]anthracene (BaA), induced CYP1A1, CYP1A2, and CYP1B1. In this study, to better understand the relative contribution of chlorination to the toxicity of polycyclic aromatic hydrocarbons (PAHs), we investigated the organ-specific distributions of 7-Cl-BaA and BaA in F334 rats. After 14 days of oral administration of 7-Cl-BaA or BaA at a concentration of 1 or 10 mg/kg body weight/day, both chemicals were detected in their plasma, which was collected 24 hr after the last administration, even at the lower dosage. Dose-dependent accumulation patterns were observed in the liver, muscle, kidney, spleen, heart, and lung. The 7-Cl-BaA concentrations in the organs were higher than those of the BaA. Furthermore, at the end of the exposure, 7-Cl-BaA specifically regulated several CYP genes in the heart more so than in other organs, although these inductions were not significant in the BaA treatment. 7-Cl-BaA might also stimulate the metabolic pathways of chemicals other than AhR-mediated metabolism, which is specific to normal PAHs, because of the alterations of CYP2J4, CYP4B1, and CYP17A1 expression in rats. In conclusion, our results imply that the chlorination of PAHs may change their organ-specific distribution and consequently alter their toxicological impacts compared to their parent PAHs.

  11. Bright white organic light-emitting diodes based on two blue emitters with similar molecular structures

    NASA Astrophysics Data System (ADS)

    Wang, Liduo; Lei, Gangtie; Qiu, Yong

    2005-06-01

    We show that highly efficient and chromatically stable white organic electroluminescent devices can be obtained, based on two blue emitters with similar structures: 9,10-di-(2-naphthyl)-anthracene (ADN) and 9,10-di-(2-naphthyl)-2-terbutyl-anthracene doped with yellow-orange emitting 5,6,11,12-tetraphenylnaphthacene (rubrene) at ultralow doping concentrations (0.01%-0.05%). The relative intensity of the blue and orange-yellow emissions could be fine-tuned by varying the doping concentrations of rubrene in the host to achieve pure white emission. The energy-transfer mechanism of ADN and rubrene with ultralow doping concentrations is discussed in terms of the long exciton diffusion distance of ADN.

  12. The effect of diet, exercise, and 7,12-dimethylbenz(a)anthracene on food intake, body composition, and carcass energy levels in virgin female BALB/c mice

    NASA Technical Reports Server (NTRS)

    Lane, Helen W.; Keith, Robert E.; Strahan, Susan; White, Marguerite T.

    1991-01-01

    The effects of diet, exercise, and 7,12-dimethylbenz(a)anthracene (DMBA), a mammary-tumor carcinogen, on food intake, energy consumption, body weight, and body composition in virgin female BALB/c mice are investigated. Diet, exercise, and DMBA all had pronounced effects on energy consumption, which in turn affected body composition. These treatments may influence manifestations of breast cancer via their effects on body composition.

  13. Time-dependent changes in antioxidative enzyme expression and photosynthetic activity of Chlamydomonas reinhardtii cells under acute exposure to cadmium and anthracene.

    PubMed

    Aksmann, Anna; Pokora, Wojciech; Baścik-Remisiewicz, Agnieszka; Dettlaff-Pokora, Agnieszka; Wielgomas, Bartosz; Dziadziuszko, Małgorzata; Tukaj, Zbigniew

    2014-12-01

    Heavy metals (HM) and polycyclic aromatic hydrocarbons (PAHs) are present in the freshwater environment at concentrations that can be hazardous to the biota. Among HMs and PAHs, cadmium (Cd) and anthracene (ANT) are the most prevalent and toxic ones. The response of Chlamydomonas cells to Cd and ANT at concentrations that markedly reduced the growth of algal population was investigated in this study. At such concentrations, both cadmium and anthracene were recognized as oxidative stress inducers, since high concentration of H2O2 in treated cultures was observed. Therefore, as a part of the "molecular phase" of the cell response to this stress, we examined the time-dependent expression of genes encoding the main antioxidative enzymes: superoxide dismutase (SOD), catalase (CAT) and ascorbate peroxidase (APX), as well as the activity of these enzymes in cells, with special attention paid to chloroplastic and mitochondrial isoforms of SOD. To characterize the cell response at the "physiological level", we examined the photosynthetic activity of stressed cells via analysis of chlorophyll a fluorescence in vivo. In contrast to standard ecotoxicity studies in which the growth end-points are usually determined, herein we present time-dependent changes in algal cell response to Cd- and ANT-induced stress. The most significant effect(s) of the toxicants on photosynthetic activity was observed in the 6th hour, when strong depression of PI parameter value, an over 50 percent reduction of the active reaction center fraction (RC0) and a 3-fold increase in non-photochemical energy dissipation (DI0/RC) were noted. At the same time, the increase (up to 2.5-fold) in mRNA transcript of SOD and CAT genes, followed by the enhancement in the enzyme activity was observed. The high expression of the Msd 3 gene in treated Chlamydomonas cells probably complements the partial loss of chloroplast Fe-SOD and APX activity, while catalase and Mn-SOD 5 seem to be the major enzymes responsible for

  14. Comparative DNA binding of 7,12-dimethylbenz[a]anthracene and some of its metabolites in mouse epidermis in vivo as revealed by the 32P-postlabeling technique.

    PubMed

    Schoepe, K B; Friesel, H; Schurdak, M E; Randerath, K; Hecker, E

    1986-04-01

    The binding of some mouse skin metabolites and related derivatives of the tumor initiator 7,12-dimethylbenz[a]anthracene (DMBA) was investigated by 32P-postlabeling analysis after its topical administration. DMBA and trans-3,4-dihydro-3,4-dihydroxy-DMBA (DMBA-3,4-dihydrodiol) both led to the formation of four DNA adducts, which showed a very similar pattern of spots on thin-layer chromatograms. With trans-8,9-dihydro-8,9-dihydroxy-7,12-dimethylbenz[a]anthracene (DMBA-8,9-dihydrodiol) one major adduct was obtained which was chromatographically indistinguishable from one of the DMBA adducts. In contrast, 7-hydroxymethyl-12-methylbenz[a]anthracene (7-OHM-12-MBA) gave rise to two major adducts which were separable from DMBA adducts. 3-hydroxy-7,12-dimethylbenz[a]anthracene (3-OH-DMBA) and 7,12-dimethylbenz[a]anthracene-7,12-epoxide (DMBA-O2) did not lead to detectable amounts of adducts. Quantitative determination of DNA binding showed that an initiating dose (i = 100 nmol) of DMBA yielded approximately 12 adducts/10(7) normal nucleotides. Adduct formation with the same dose of DMBA-3,4-dihydrodiol was 7-8 times higher. At a 4-fold higher dose level, DMBA-8,9-dihydrodiol exhibited a 3- to 6-times weaker binding and 7-OHM-12-MBA a slightly stronger binding than DMBA. Chromatography of the DMBA and DMBA-3,4-dihydrodiol adducts with a solvent containing borate showed a decreased mobility of two out of four adducts in each case. These adducts were also sensitive to oxidation by periodate. The results suggest that two DMBA adducts carried vicinal cis-hydroxyl groups and thus were probably derived from the anti-3,4-dihydrodiol-1,2-oxide(s) of DMBA. The other two adducts were probably derived from the syn-stereoisomer(s). When the DNA-modifying capabilities and initiating activities of the more prominent mouse-skin metabolites are considered in relation to DMBA, DMBA-3,4-dihydrodiol is postulated to be a proximate and DMBA-3,4-dihydrodiol-1,2-oxide(s) to be ultimate

  15. Carcinogenicity and DNA binding of benzo(a)pyrene and 7,12-dimethylbenz(a)anthracene in rainbow trout by controlled laboratory exposure

    SciTech Connect

    Fong, A.T.; Hendricks, J.D.; Bailey, G.S. )

    1988-09-01

    Polycyclic aromatic hydrocarbons (PAH) recently have been implicated as etiological agents responsible for observed neoplasia in some feral fish populations. However, establishing a direct causal relationship has not been possible in part because only a few PAH have been tested for carcinogenicity in fish models. The present studies were undertaken to characterize the carcinogenicity and DNA binding of benzo(a)pyrene (BP) and 7,12-dimethylbenz(a)anthracene (DMBA) in the rainbow trout by controlled laboratory exposure. Two parameters which may influence tumor response to PAH were examined, route of exposure and life stage at exposure. Although rainbow trout seldom inhibit polluted environments where fish tumor epizootics occur, this extensively studied fish species provides a useful model for examining the carcinogenic effects of environmental contamination because they have been shown to be highly sensitive to the carcinogenic effects of aflatoxin B{sub 1} and over 20 other carcinogens. The results of these studies show that the trout is sensitive to the carcinogenic effects of PAH at the embryo, fry, and juvenile life stages, and that tumor response and site of tumor formation depend on the particular PAH used, the dose of PAH, and the route of administration.

  16. Differential composition of bacterial communities as influenced by phenanthrene and dibenzo[a,h]anthracene in the rhizosphere of ryegrass (Lolium perenne L.).

    PubMed

    Corgié, S C; Beguiristain, T; Leyval, C

    2006-12-01

    Bioremediation technologies of Polycyclic Aromatic Hydrocarbons (PAH) are often limited by the recalcitrance to biodegradation of high molecular weight (HMW) PAH. Rhizosphere is known to increase the biodegradation of PAH but little is known about the biodegradability of these HMW compounds by rhizosphere bacteria. This study compared the effects of a 3 and a 5-ring PAH, phenanthrene (PHE) and dibenzo[a,h]anthracene (dBA) respectively, on the composition of bacterial community, the bacterial density and the biodegradation activity. Compartmentalized devices were designed to harvest three consecutive sections of the rhizosphere. Rhizosphere and non-rhizosphere compartments were filled with PHE or dBA spiked or unspiked sand and inoculated with a soil bacterial inoculum. Different bacterial communities and degradation values were found 5 weeks after spiking with PHE (41-76% biodegradation) and dBA (12-51% biodegradation). In sections closer to the root surface, bacterial populations differed as a function of the distance to roots and the PAH added, whereas in further rhizosphere sections, communities were closer to those of the non-planted treatments. Biodegradation of PHE was also a function of the distance to roots, and decreased from 76 to 42% within 9 mm from the roots. However, biodegradation of dBA was significantly higher in the middle section (3-6 mm from roots) than the others. Rhizosphere degradation of PAH varies with the nature of the PAH, and C fluxes from roots could limit the degradation of dBA.

  17. Influence of mode of exposure and the presence of a tubiculous polychaete on the fate of benz(a)anthracene in the benthos

    SciTech Connect

    McElroy, A.E.; Farrington, J.W.; Teal, J.M. )

    1990-11-01

    The distribution and metabolism of ({sup 14}C-12)benz(a)-anthracene (BA) was followed in benthic microcosms in the presence and absence of the polychaete Nereis virens for periods of 4-25 days to simultaneously assess the effects of mode of introduction and the presence of large burrowing organisms on the fate of polycyclic aromatic hydrocarbons (PAH) and their metabolites in the benthos. Radiolabeled BA was added to the chambers in three ways: already sorbed to the entire sediment reservoir, directly into the water column, or incorporated into food for the worms. BA added to the water column was more available for uptake and metabolism by worms and microbial mineralization to CO{sub 2} than BA previously sorbed to the entire sediment reservoir. In experiments with the sediment reservoir uniformly labeled with BA, worms increased flux of BA from the sediment, and with time, their presence led to increased rates of microbial mineralization of BA to CO{sub 2}. Dietary BA was most rapidly metabolized by Nereis.

  18. Combination between Taxol-Encapsulated Liposomes and Eruca sativa Seed Extract Suppresses Mammary Tumors in Female Rats Induced by 7,12 Dimethylbenz(α)anthracene.

    PubMed

    Shaban, Nadia; Abdel-Rahman, Salah; Haggag, Amany; Awad, Doaa; Bassiouny, Ahmad; Talaat, Iman

    2016-01-01

    Taxol (paclitaxel) is a powerful anti-cancer drug widely used against several types of malignant tumors. Because Taxol may exert several side effects, a variety of formulations have been developed. One of these features liposomes, regarded as one of the most promising drug carriers, biocompatible and best able to reduce drug toxicity without changing efficacy against tumor cells. Eruca sativa seed extract (SE) is considered a promising natural product from cruciferous vegetables against breast cancer, increasing chemotherapeutic and eliminating harmful side effects. The effects of Taxol-encapsulated liposomes (T) alone and in combination between Eruca sativa seed extract on nuclear factor kappa B (NF-κB), cyclooxygenase-2 (COX-2) and B-cell lymphoma-2 (Bcl-2) gene expression levels were investigated in rat mammary gland carcinogenesis induced by 7,12 dimethylbenz(α) anthracene (DMBA) using qRT-PCR. The results showed that DMBA increased NF-κB, COX-2 and Bcl-2 gene expression levels and lipid peroxidation (LP), while decreasing glutathione-S-transferase (GST) and superoxide dismutase (SOD) activities and total antioxidant concentration (TAC) compared to the control group. T and T-SE treatment reduced NF-κB, COX-2 and Bcl-2 gene expression levels and LP. Hence, T and T-SE treatment appeared to reduce inflammation and cell proliferation, while increasing apoptosis, GST and SOD activities and TAC.

  19. Effect of permethrin, anthracene and mixture exposure on shell components, enzymatic activities and proteins status in the Mediterranean clam Venerupis decussata.

    PubMed

    Sellami, Badreddine; Khazri, Abdelhafidh; Mezni, Amine; Louati, Héla; Dellali, Mohamed; Aissa, Patricia; Mahmoudi, Ezzeddine; Beyrem, Hamouda; Sheehan, David

    2015-01-01

    Anthracene (ANT) and permethrin (PER) are two of the more toxic compounds reaching the marine environment. This study aimed to determine the impact of these molecules on Venerupis decussata, an economically important species cultured on the Tunisian coast. Shell structure and its possible transformation upon exposure to the two contaminants were studied by X-ray diffraction and gravimetric analyses. Results revealed a phase transition in shell composition from aragonite to calcite after PER exposure, to a mixture of PER and ANT (Mix) but not for ANT alone. Catalase (CAT), superoxide dismutase (SOD) and glutathione transferase (GST) activities were determined in digestive gland and gills after exposure to ANT, PER and Mix to assess the impact of the contamination on the oxidative status of V. decussata. Enzyme activities increased in the digestive gland after PER treatment and in the gills after ANT treatment. PER exposure significantly reduced the levels of free thiols and increased levels of carbonylated proteins in the digestive gland, as compared to controls. In contrast, ANT exposure significantly reduced free thiols and increased the number of carbonylated proteins in the gills. Mix induced additive effects as measured by both enzymatic and proteomic approaches. The present study suggests that PER has a strong effect on shell structure; that PER and ANT exposure generate compound-dependent oxidative stress in the tissues of V. decussata and that a mixture of the two compounds has synergistic effects on biochemical response.

  20. Oral artemisinin prevents and delays the development of 7,12-dimethylbenz[a]anthracene (DMBA)-induced breast cancer in the rat.

    PubMed

    Lai, Henry; Singh, Narendra P

    2006-01-08

    Artemisinin, a compound isolated from the sweet wormwood Artemisia annua L., has previously been shown to have selective toxicity towards cancer cells in vitro. In the present experiment, we studied the potential of artemisinin to prevent breast cancer development in rats treated with a single oral dose (50mg/kg) of 7,12-dimethylbenz[a]anthracene (DMBA), known to induce multiple breast tumors. Starting from the day immediately after DMBA treatment, one group of rats was provided with a powdered rat-chow containing 0.02% artemisinin, whereas a control group was provided with plain powdered food. For 40 weeks, both groups of rats were monitored for breast tumors. Oral artemisinin significantly delayed (P<.002) and in some animals prevented (57% of artemisinin-fed versus 96% of the controls developed tumors, P<.01) breast cancer development in the monitoring period. In addition, breast tumors in artemisinin-fed rats were significantly fewer (P<.002) and smaller in size (P<.05) when compared with controls. Since artemisinin is a relatively safe compound that causes no known side effects even at high oral doses, the present data indicate that artemisinin may be a potent cancer-chemoprevention agent.

  1. Tangeretin ameliorates oxidative stress in the renal tissues of rats with experimental breast cancer induced by 7,12-dimethylbenz[a]anthracene.

    PubMed

    Lakshmi, Arivazhagan; Subramanian, Sorimuthu Pillai

    2014-09-02

    Tangeretin, a citrus polymethoxyflavone, is an antioxidant modulator which has been shown to exhibit a surfeit of pharmacological properties. The present study was hypothesized to explore the therapeutic activity of tangeretin against 7,12-dimethylbenz[a]anthracene (DMBA) induced kidney injury in mammary tumor bearing rats. Recently, we have reported the chemotherapeutic effect of tangeretin in the breast tissue of DMBA induced rats. Breast cancer was induced by "air pouch technique" with a single dose of 25mg/kg of DMBA. Tangeretin (50mg/kg/day) was administered orally for four weeks. The renoprotective nature of tangeretin was assessed by analyzing the markers of oxidative stress, proinflammatory cytokines and antioxidant competence in DMBA induced rats. Tangeretin treatment revealed a significant decline in the levels of lipid peroxides, inflammatory cytokines and markers of DNA damage, and a significant improvement in the levels of enzymatic and non-enzymatic antioxidants in the kidney tissue. Similarly, mRNA, protein and immunohistochemical analysis substantiated that tangeretin treatment notably normalizes the renal expression of Nrf2/Keap1, its downstream regulatory proteins and the inflammatory cytokines in the DMBA induced rats. Histological and ultrastructural observations also evidenced that the treatment with tangeretin effectively protects the kidney from DMBA-mediated oxidative damage, hence, proving its nephroprotective nature.

  2. The anharmonic quartic force field infrared spectra of five non-linear polycyclic aromatic hydrocarbons: Benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene

    NASA Astrophysics Data System (ADS)

    Mackie, Cameron J.; Candian, Alessandra; Huang, Xinchuan; Maltseva, Elena; Petrignani, Annemieke; Oomens, Jos; Mattioda, Andrew L.; Buma, Wybren Jan; Lee, Timothy J.; Tielens, Alexander G. G. M.

    2016-08-01

    The study of interstellar polycyclic aromatic hydrocarbons (PAHs) relies heavily on theoretically predicted infrared spectra. Most earlier studies use scaled harmonic frequencies for band positions and the double harmonic approximation for intensities. However, recent high-resolution gas-phase experimental spectroscopic studies have shown that the harmonic approximation is not sufficient to reproduce experimental results. In our previous work, we presented the anharmonic theoretical spectra of three linear PAHs, showing the importance of including anharmonicities into the theoretical calculations. In this paper, we continue this work by extending the study to include five non-linear PAHs (benz[a]anthracene, chrysene, phenanthrene, pyrene, and triphenylene), thereby allowing us to make a full assessment of how edge structure, symmetry, and size influence the effects of anharmonicities. The theoretical anharmonic spectra are compared to spectra obtained under matrix isolation low-temperature conditions, low-resolution, high-temperature gas-phase conditions, and high-resolution, low-temperature gas-phase conditions. Overall, excellent agreement is observed between the theoretical and experimental spectra although the experimental spectra show subtle but significant differences.

  3. Effect of mangrove black tea extract from Ceriops decandra (Griff.) on hematology and biochemical changes in dimethyl benz[a]anthracene-induced hamster buccal pouch carcinogenesis.

    PubMed

    Sithranga Boopathy, N; Kathiresan, K; Jeon, Y J

    2011-09-01

    Effect of the black tea extracted from a mangrove plant species, Ceriops decandra (Griff.) was studied on dimethyl benz[a]anthracene (DMBA)-induced changes in blood hematology and plasma non-enzymatic antioxidants in male hamsters. Hamsters were painted with 0.5% solution of DMBA in liquid paraffin on the right buccal pouch three times in a week up to 14 weeks. Each application treated with 0.4mg of DMBA. The mangrove black tea extract (MBTE) was administrated orally with 5mgkg(-1) twice a day and then with DMBA on alternate days. Results showed that the DMBA caused a significant (P<0.05) decline in the levels of reduced glutathione (GSH), vitamin-C, -E, red blood cells, hemoglobin, mean corpuscular volume and hematocrit; and increase in the levels of WBC, platelets, lymphocytes and neutrophils. The MBTE prevented the DMBA-induced adverse changes significantly in blood and biochemical parameters of the male hamsters. This work concluded that the black tea extracted from the coastal mangrove species C. decandra prevented the DMBA-induced buccal pouch carcinogenesis in hamsters.

  4. Effect of gamma-linolenic acid and dihomo-gamma-linolenic acid 7,12-dimethylbenz(a)anthracene-induced mammary tumorigenesis

    SciTech Connect

    Ramchurren, N.; Karmali, R.A. )

    1991-03-15

    Gamma-linolenic acid (GLA) and its sequential metabolite, dihomogamma-linolenic acid (DHLA) have been reported to influence growth of neoplastic cells in culture. The pure forms of these fatty acids have not been tested in vivo. The authors have studied the effect of GLA and DHLA on mammary tumors induced by 7,12-dimethylbenz(a) anthracene (DMBA) (7.5 mg/rat) in female Sprague-Dawley rats. Rats received either 0.15 g of GLA or DHLA or corn oil (CO) orally, twice weekly for a period of 12 weeks. All three groups of rats were maintained on a diet containing 5% (w/w) corn oil as fat. Tumor incidence and multiplicity were recorded. The group receiving 0.15 g Co had higher tumor yields than those receiving GLA or DHLA. At the end of the experiment, tumor incidence was the lowest in the group receiving DHLA. Tumor multiplicity was consistently lowest with GLA. Fatty acid composition of mammary tissue and liver reflected that of fatty acid treatment. These results suggest that oral administration of GLA or DHLA retards the development of DMBA-induced mammary tumors in rats receiving a diet containing 5% (w/w) corn oil.

  5. Paternal selenium deficiency but not supplementation during preconception alters mammary gland development and 7,12-dimethylbenz[a]anthracene-induced mammary carcinogenesis in female rat offspring.

    PubMed

    Guido, Luiza N; Fontelles, Camile C; Rosim, Mariana P; Pires, Vanessa C; Cozzolino, Silvia M F; Castro, Inar A; Bolaños-Jiménez, Francisco; Barbisan, Luis F; Ong, Thomas P

    2016-10-15

    Breast cancer is a global public health problem and accumulating evidence indicates early-life exposures as relevant factors in the disease risk determination. Recent studies have shown that paternal nutrition can influence offspring health including breast cancer risk. Selenium is a micronutrient with essential role in central aspects of embryogenesis, male fertility and cancer and that has been extensively studied as a chemopreventive agent in several breast cancer experimental models. Thus, we designed an animal study to evaluate whether paternal selenium deficiency or supplementation during preconception could affect the female offspring mammary gland development and breast cancer susceptibility. Male Sprague-Dawley rats were fed AIN93-G diet containing 0.15 ppm (control diet), 0.05 ppm (deficient diet) or 1 ppm (supplemented diet) of selenium for 9 weeks and mated with control female rats. Mammary carcinogenesis was induced with 7,12-dimethylbenz[a]anthracene (DMBA) in their female offspring. Paternal selenium deficiency increased the number of terminal end buds, epithelial elongation and cell proliferation in the mammary gland of the female rat offspring and these effects were associated with higher susceptibility to DMBA-induced mammary tumors (increased incidence and higher grade tumors). On the other hand, paternal selenium supplementation did not influence any of these parameters. These results highlight the importance of father's nutrition including selenium status as a relevant factor affecting daughter's breast cancer risk and paternal preconception as a potential developmental stage to start disease preventive strategies.

  6. Environmental concentrations of benz[a]anthracene induce developmental defects and DNA damage and impair photomotor response in Japanese medaka larvae.

    PubMed

    Le Bihanic, Florane; Sommard, Vivien; Perrine, de Lansalut; Pichon, Anaïk; Grasset, Julie; Berrada, Saadia; Budzinski, Hélène; Cousin, Xavier; Morin, Bénédicte; Cachot, Jérôme

    2015-03-01

    Benz[a]anthracene (BaA) is a ubiquitous polycyclic aromatic hydrocarbon found in numerous aquatic ecosystems. However, ecotoxicological data in aquatic organisms are scarce. To remedy this lack of data, Japanese medaka (Oryzias latipes) embryos were exposed to BaA and toxic effects were investigated at multiple toxicological endpoints. Japanese medaka embryos were incubated onto BaA-spiked artificial sediment for 9 days at low or moderate environmental concentrations ranging from 0.9 to 12 µgg(-1) dw. BaA-exposed embryos exhibited significant tachycardia. BaA exposure was also shown to increase CYP1A activity in the hepato-biliary tissue as well as craniofacial deformities and DNA damage in pro-larvae. The photomotor response of BaA-exposed larvae was reduced in comparison to the control group. According to this set of tests, the lowest tested and observed effect concentration (LOEC) for Japanese medaka early life stages was equivalent to 0.92 µgg(-1) dw of BaA. This concentration fall into the range of concentrations frequently encountered in sediments of polluted aquatic ecosystems. Taking into consideration these results, BaA represents a threat for fish early life stages in particular those developing onto or into contaminated sediments.

  7. Ontogeny of the major xenobiotic-metabolizing enzymes expression and the dietary lipids modulatory effect in the rat dimethylbenz(a)anthracene-induced breast cancer model.

    PubMed

    Manzanares, Miguel Ángel; Solanas, Montserrat; Moral, Raquel; Escrich, Raquel; Vela, Elena; Escrich, Eduard

    2014-12-01

    Breast cancer is the most common malignancy in women worldwide. Environmental factors such as xenobiotic exposure and lifestyle and nutrition play a key role in its etiology. This study was designed to evaluate the age-related changes in the expression of major xenobiotic-metabolizing enzymes (XMEs) in the rat liver and the mammary gland in the dimethylbenz(a)anthracene-induced breast cancer model. The influence of dietary lipids on the ontogeny of XMEs was also evaluated. mRNA and protein levels of phase I (CYP1A1, CYP1A2, and CYP1B1) and phase II (NAD(P)H:quinone acceptor oxidoreductase 1 and GSTP1) enzymes were analyzed, as well as their regulation by AhR and Nrf2, respectively. Results showed differences in the phase I enzymes expression, whereas little changes were obtained in phase II. High corn oil and olive oil diets differentially influenced the expression of age-related changes, suggesting that the different susceptibility to xenobiotic exposure depending upon the age may be modulated by dietary factors.

  8. Use of the Integrated Biomarker Response to Measure the Effect of Short-term Exposure to Dibenz[a,h]anthracene in Common carp (Cyprinus carpio).

    PubMed

    Kim, Ja-Hyun; Kim, Woo-Keun

    2016-04-01

    Dibenz[a,h]anthracene (DbA) is a polycyclic aromatic hydrocarbon that is released into the environment through incomplete combustion of gasoline, cigarettes, and coal tar. The effects of short-term (10 days) exposure of common carp (Cyprinus carpio) to DbA (0-50 µg L(-1)) were evaluated using the following four biomarkers: DNA damage, 7-ethoxyresorufin-O-deethylase (EROD) activity, acetylcholinesterase (AChE) activity, and vitellogenin (VTG) levels. An integrated biomarker response (IBR) was calculated for exposure to DbA, and the results were compared with those in our previous study of two other PAHs, benzo[k]fluoranthene (BkF) and benzo[a]pyrene (BaP). DbA exposure resulted in a significant (p < 0.05) increase in DNA damage, EROD activity, and VTG levels relative to the control. By contrast, DbA did not affect AChE activity. The IBR increased as the concentration of DbA increased. Based on the IBR values, the order of toxicity for the PAHs was BkF > BaP > DbA. Our results suggest that the IBR can be used as a quantitative tool for evaluating the responses of multiple biomarkers to PAH exposure.

  9. The effect of diet and exercise on incidence of 7,12 dimethylbenz(a)anthracene-induced mammary tumors in virgin BALB/c mice

    SciTech Connect

    White, M.T.; Lane, H.W.; Teer, P.; Keith, R.E.; Strahan, S. NASA, Houston, TX )

    1991-03-15

    The effects of rotating-drum treadmill exercise and diet on 7,12 dimethylbenz(a)anthracene (DMBA)-induced mammary tumors were investigated in virgin female BALB/c mice. The animals were fed one of three diets: AIN 76 (SD), high-fat diet (HFD), or a restricted calorie diet (RCD). All diets were begun at 6 weeks of age and fed ad libitum except for the restricted diet which was fed at 70% of the SD. At 8 weeks of age all animals received the first of 6 consecutive DMBA doses via gastric tube. Each diet had an exercise and no exercise subgroup. Exercise began at 10 wks of age (6 m/min for 60 min, 5 d/wk) and continued throughout the 9.5 mo. study. Exercise reduced feed consumption in SD and HFD groups. Body weight was similar in all groups with HFDEx having the lowest body wt. Calorie restriction had no effect on body wt. but reduced mammary tumor incidence in the SD groups; however, exercise did affect mammary tumor incidence in the other groups as follows: RCD = 28%, RCDEx = 13%; HFD = 31%, HFDEx = 19%. Caloric consumption appeared to be related to mammary tumor incidence rather than body wt. or dietary fat.

  10. Chemopreventive efficacy and anti-lipid peroxidative potential of Jasminum grandiflorum Linn. on 7,12-dimethylbenz(a)anthracene-induced rat mammary carcinogenesis.

    PubMed

    Kolanjiappan, K; Manoharan, S

    2005-12-01

    The aim of this study was to investigate the chemopreventive efficacy and anti-lipid peroxidative potential of Jasminum grandiflorum Linn. on 7,12-dimethylbenz(a)anthracene (DMBA)-induced rat mammary carcinogenesis. Mammary tumors were developed by a single subcutaneous injection of 25 mg DMBA in 1 mL emulsion of sunflower oil and physiological saline. The tumor incidence and tumor volume that formed in the breast were determined. Oral administration of ethanolic extract of J. grandiflorum flowers (JgEt) at a dose of 300 mg/kg body weight for 14 weeks to DMBA-injected animals completely prevented the formation of tumors in the pre-initiation period. JgEt also exerted significant anti-lipid peroxidative effect and improved the antioxidant defense system in DMBA-treated rats. The results of this study clearly indicate that JgEt has potent chemopreventive efficacy in experimental mammary carcinogenesis and further studies are warranted to isolate and characterize the bioactive principle from JgEt.

  11. Chokeberry (Aronia melanocarpa) juice modulates 7,12-dimethylbenz[a]anthracene induced hepatic but not mammary gland phase I and II enzymes in female rats.

    PubMed

    Szaefer, Hanna; Krajka-Kuźniak, Violetta; Ignatowicz, Ewa; Adamska, Teresa; Baer-Dubowska, Wanda

    2011-03-01

    Chokeberry is a rich source of procyanidins known to have several types of biological activity including anticarcinogenic potential in experimental models. In this study we examined the effect of chokeberry juice on the hepatic and mammary gland carcinogen metabolizing enzyme expression altered by the polycyclic aromatic hydrocarbon, 7,12-dimethylbenz[a]anthracene (DMBA). Sprague-Dawley rats were gavaged with chokeberry juice (8 ml/kg b.w.) for 28 consecutive days. DMBA was administered i.p. on the 27th and the 28th days. Pretreatment with chokeberry juice reduced the activity of CYP1A1 and increased that of CYP2B involved in metabolic activation/detoxication of DMBA in rat liver, as well as expression and activity of phase II enzymes. Chokeberry juice had no effect on these parameters in the mammary gland and DMBA induced DNA damage in rat blood cells. These results together with our earlier observations indicate that metabolic alterations induced by chokeberry feeding are tissue specific and depend on the class of carcinogen.

  12. Effects of anthracene, pyrene and benzo[a]pyrene spiking and sewage sludge compost amendment on soil ecotoxicity during a bioremediation process.

    PubMed

    Hamdi, Helmi; Manusadzianas, Levonas; Aoyama, Isao; Jedidi, Naceur

    2006-11-01

    The fate of spiked anthracene, pyrene and benzo[a]pyrene in soil with or without sewage sludge compost was assessed during a 6-month bioremediation process simulating landfarming. Bioassays and physico-chemical analyses were employed to monitor toxicity change in soil samples and elutriates through ten sampling campaigns. Pearson product-moment correlation coefficient was determined to measure the strength of relationship between bioassays and physico-chemical analyses. The PAH dissipation in soil was enhanced after the first water addition, and the remaining amounts at the end of the experiment were positively correlated to the number of benzene rings and the presence of sewage sludge compost. Toxicity of soil elutriates to Daphnia magna was evident at early stages, originating exclusively from sewage sludge compost amendment. The lettuce root elongation was continuously inhibited by elutriates for all the treatments including control soil, probably due to high salinity or to unaddressed leachable phytotoxic compounds that were present in the experimental soil. The newly developed direct solid-phase chronic toxicity test using ostracod (Heterocypris incongruens) succeeded in evaluating the soil-bound PAH toxicity, as PAHs could not be detected in elutriates.

  13. Interfacial approach to polyaromatic hydrocarbon toxicity: phosphoglyceride and cholesterol monolayer response to phenantrene, anthracene, pyrene, chrysene, and benzo[a]pyrene.

    PubMed

    Korchowiec, Beata; Corvis, Yohann; Viitala, Tapani; Feidt, Cyril; Guiavarch, Yann; Corbier, Catherine; Rogalska, Ewa

    2008-10-30

    Interactions of phenantrene, anthracene, pyrene, chrysene, and benzo[a]pyrene (polyaromatic hydrocarbons) with model phospholipid membranes were probed using the Langmuir technique. The lipid monolayers were prepared using 1,2-dipalmitoyl-sn-glycero-3-phosphocholine, 1,2-dipalmitoyl-sn-glycero-3-phosphoethanolamine, 1,2-dipalmitoyl-sn-glycero-3-phosphoglycerol, 1,2-dipalmitoyl-sn-glycero-3-phosphoserine, 1,2-myristoyl-sn-glycero-3-phosphoethanolamine, 1,2-dilauroyl-sn-glycero-3-phosphocholine, and cholesterol. Surface pressure and electrical surface potential were measured on mixed phospholipid/PAH monolayers spread on a pure water subphase. The morphology of the mixed monolayers was followed with Brewster angle microscopy. Polarization-modulation infrared reflection-absorption spectroscopy spectra obtained on DPPE/benzo[a]pyrene showed that the latter interacts with the carbonyl groups of the phospholipid. On the other hand, the activity of phospholipase A2 toward DLPC used as a probe to locate benzo[a]pyrene in the monolayers indicates that the polyaromatic hydrocarbons are not accessible to the enzyme. The results obtained show that all PAHs studied affect the properties of the pure lipid, albeit in different ways. The most notable effects, namely, film fluidization and morphology changes, were observed with benzo[a]pyrene. In contrast, the complexity of mixed lipid monolayers makes the effect of PAHs difficult to detect. It can be assumed that the differences observed between PAHs in monolayers correlate with their toxicity.

  14. Protective effects of hemin and tetrakis(4-benzoic acid)porphyrin on bacterial mutagenesis and mouse skin carcinogenesis induced by 7, 12-dimethylbenz[a]anthracene.

    PubMed

    Chung, W Y; Lee, J M; Lee, W Y; Surh, Y J; Park, K K

    2000-12-20

    Porphyrins which are widespread in nature can interfere with the actions of certain carcinogens and mutagens, and have also been used clinically in photodynamic therapy (PDT) of tumors. Porphyrins such as chlorophyll, chlorophyllin (CHL) and hemin are known to inactivate various mutagens by forming complexes with them. Tetrakis(4-benzoic acid)porphyrin (TBAP) has been developed as a photosensitizer for PDT and its metal complex, MnTBAP has been shown to be efficacious in a variety of in vitro and in vivo oxidative stress models of human diseases. In the present study, we have found that TBAP and hemin exert concentration-related inhibition of his(+) reversion in Salmonella typhimurium TA100 induced by 7, 12-dimethylbenz[a]anthracene (DMBA), and significantly reduced both incidence and multiplicity of skin tumors when topically applied prior to treatment of 12-O-tetradecanoylphorbol-13-acetate in female ICR mice. Covalent DNA binding of DMBA in mouse skin was also significantly inhibited by topical application of TBAP or hemin as well as CHL. These results suggest the chemopreventive potential of compounds containing a porphyrin nucleus.

  15. Effects of 4-n-octylphenol on the induction of mammary tumors induced by 7,12-dimethylbenz[a]anthracene in rats.

    PubMed

    Kawaguchi, H; Umekita, Y; Yoshida, H

    2009-03-01

    We previously reported that a neonatal administration of diethylstilbestrol or 17beta-estradiol affected the mammary carcinogenesis induced by 7,12-dimethylbenz[a]anthracene (DMBA) in rats. The aim of this present study was to investigate the effects of 4-n-octylphenol (OP), a weak estrogenic disruptor, on the induction of mammary carcinomas (MC) and benign proliferative lesions (PL) induced by DMBA in rats. All female rats were administered at 0, 0.1, 10, 100, and 1,000 microg OP once at birth, given 10 mg DMBA at 50 days after birth, and thereafter underwent necropsy at 351 days after birth. All male rats were given 10 mg DMBA at 28, 42, and 56 days after birth, and 0, 10, 100, and 1,000 ppm OP fed from day 70-153; they underwent necropsy at 153 days after birth. Neonatal single administration of OP in female rats showed no effects such as persistent estrus, anovulatory ovaries, or PL. A slight increase in numbers of rats with MC occurred at the highest dosage. Feeding a large dose of OP for a long period in male rats induced atrophy of testes and slightly increased numbers of affected MC but not increased numbers of males while it showed no effects on PL. These results suggested that administration of a large dose of OP for a long period may have had a minimal effect on mammary carcinogenesis in male rats.

  16. Hesperidin a citrus bioflavonoid modulates hepatic biotransformation enzymes and enhances intrinsic antioxidants in experimental breast cancer rats challenged with 7, 12-dimethylbenz (a) anthracene.

    PubMed

    Nandakumar, Natarajan; Balasubramanian, Maruthaiveeran Periyasamy

    2012-01-01

    DMBA is a major class of potent genotoxic chemical carcinogen present in the environment and it may increase breast cancer risk. Flavonoids have been shown to have interesting biological activities in many experimental investigations. Hesperidin is one of the citrus flavonoid shown to be active against various oxidative stress mediated diseases. The aim of the present study was to investigate the beneficial impact of a natural citrus flavonoglycoside hesperidin against 7, 12-Dimethylbenz [a] anthracene challenged experimental breast carcinogenesis with reference to drug metabolizing enzymes and intrinsic antioxidant status. The female Sprague-Dawley rats were orally administered with single dose of 7, 12-DMBA to induce breast cancer and were treated with hesperidin [30mg/kg/body weight] for a consecutive 45 days. The results revealed that there was a significant reduction in the status of antioxidants levels and also significant alterations in the drug metabolizing enzymes were found in genotoxin DMBA exposed animals. Interestingly these, altered levels were significantly revered back to near normal in hesperidin administered animals via enhancing the intrinsic antioxidant levels and induction in Phase II enzymes and modulation in Phase I enzyme levels. Thus the antigenotoxic activity of hesperidin may be due to the modulatory effect in biotransformation enzymes and excellent antioxidant potentials which paving a way to consider hesperidin against the genotoxin involved oxidative stress mediated diseases.

  17. Stark effect of intrinsic and extrinsic charge-transfer excitons in a linear donor-acceptor stack: anthracene-pyromellitic dianhydride.

    PubMed

    Weiser, Gerhard; Elschner, Andreas

    2009-06-25

    Anthracene-PMDA single crystals display at 2K about 70 meV below a well-known intrinsic charge-transfer exciton three narrow absorption lines, which are attributed to CT excitons bound to defects of a few 10(-5) concentration. All excitons respond very sensitively to electric fields along the molecular stack because of the large dipole moment, about 2 eA, of an ionized donor-acceptor pair, but only intrinsic excitons observe an optical selection rule. Although the triclinic unit cell contains only one pair of molecules, excitons appear in field-modulated spectra as near-degenerate doublets of different parity with very small splitting. The line shape of the EA spectra and selection rules with respect to the polarization of light and orientation of the field are consistent with the inversion symmetry of the lattice and the molecules. The simple crystal structure enables identification of the defects that are responsible for extrinsic excitons. Symmetry consideration based on translation invariance lead to a new interpretation of intrinsic excitons as true crystal states with charge transfer from the donor to the acceptor sublattice.

  18. Inhibition by an extract of Ocimum sanctum of DNA-binding activity of 7,12-dimethylbenz[a]anthracene in rat hepatocytes in vitro.

    PubMed

    Prashar, R; Kumar, A; Hewer, A; Cole, K J; Davis, W; Phillips, D H

    1998-06-19

    Ocimum sanctum is a traditional medicinal plant. Previous studies have shown that extracts of O. sanctum inhibit the induction of skin papillomas in mice by 7,12-dimethylbenz[a]anthracene (DMBA). In the present study, primary cultures of rat hepatocytes were treated with 0-500 microg of O. sanctum extract for 24 h and then with DMBA (10 or 50 microg) for 18 h. Cells were then harvested and their DNA was isolated and analyzed by 32P-postlabelling. A significant reduction in the levels of DMBA-DNA adducts was observed in all cultures pretreated with O. sanctum extract. This effect was more pronounced at the lower dose of DMBA (10 microg). Hepatocytes which were treated with the highest dose of extract (500 microg) showed a maximum reduction of 93% in the mean values of DMBA-DNA adducts. The viability of the cells was not adversely affected by pretreatment with extract. Our findings suggest that O. sanctum leaf extract blocks or suppresses the events associated with chemical carcinogenesis by inhibiting metabolic activation of the carcinogen.

  19. Uptake and phytotoxicity of anthracene and benzo[k]fluoranthene applied to the leaves of celery plants (Apium graveolens var. secalinum L.).

    PubMed

    Wieczorek, Jolanta; Sienkiewicz, Stanisław; Pietrzak, Monika; Wieczorek, Zbigniew

    2015-05-01

    The above-ground parts of celery plants were exposed to two polycyclic aromatic hydrocarbons (PAHs): 3-ring anthracene (ANT) and 5-ring benzo[k]fluoranthene (BkF), and the combination of ANT and BkF. After 43 days of exposure (overall dose of 1325µg/plant), celery plants retained only 1.4% of the total dose of ANT and 17.5% of the total dose of BkF. After exposure to a combination of ANT and BkF (1325µg of each compound per plant), the average ANT concentrations were more than twofold higher in/on leaf blades, whereas BkF levels were insignificantly higher. Under natural photoperiod conditions equivalent to a normal day, the combined application of ANT and BkF to the above-ground parts of celery plants slowed down physicochemical transformations of ANT. A similar effect was observed when PAHs were applied to glass surfaces. The combination of both PAHs probably led to stacking interactions, which decreased volatilization, in particular of ANT. Phytotoxicity of ANT and BkF could not be unambiguously established based on the results of this study. In all analyzed treatments, the chlorophyll content of leaf blades remained unchanged. Foliar application of ANT reduced ascorbic acid levels in all analyzed plant parts and increased the total acidity of celery leaves. In all experimental treatments, the total phenolic content of leaves increased up to 15%. Interestingly, ANT and BkF did not produce cumulative effects when applied in combination (when total PAH concentrations per plant were twofold higher).

  20. Chemopreventive effect of selenium-enriched Japanese radish sprout against breast cancer induced by 7,12-dimethylbenz[a]anthracene in rats.

    PubMed

    Yamanoshita, Osamu; Ichihara, Shu; Hama, Hidetoshi; Ichihara, Gaku; Chiba, Momoko; Kamijima, Michihiro; Takeda, Iwao; Nakajima, Tamie

    2007-06-01

    Breast cancer is one of the major cancers in women, and dietary intake must be controlled to prevent it. Selenium (Se), especially Se compound in vegetables, is thought to be a promising chemopreventive dietary ingredient for preventing breast cancer. In this study, we developed Se-enriched Japanese radish sprout using a special Se-additional fertilizer, and identified the Se chemical forms. The newly developed Se-enriched sprout is produced within a week by the tank forming method, and the major chemical form was identified as Se-methylselenocysteine (MeSeCys) (80%). Then, the chemopreventive effects of the Se-enriched sprout were investigated using Sprague-Dawley female rats with mammary cancer, induced by a single oral dose of 10 mg or 14 mg of 7, 12-dimethylbenz[a]anthracene (DMBA). Mammary tumors were found in 11, 16 and 2 rats treated with DMBA and thereafter fed the basal (n = 34), sprout-added basal (n = 30) and Se-enriched sprout-added test diets (n = 30), respectively. The incidence of mammary tumors was significantly lower in the Se-enriched sprout-added test diet group (7%) than in the basal diet group (32%) or sprout-added basal diet group (53%). In contrast, no significant difference was detected in the numbers and incidence of the tumor between the basal diet group and Se-enriched sprout-added test diet group before DMBA-dosing. These results suggest that the diet supplement of Se-enriched sprout after DMBA-dosing provides a significant chemoprevention against chemical-induced mammary cancer. Thus, Se-enriched sprout may be a useful dietary ingredient for preventing breast cancer.

  1. Tumor suppressor p16INK4A/Cdkn2a alterations in 7, 12-dimethylbenz(a)anthracene (DMBA)-induced hamster cheek pouch tumors

    PubMed Central

    Li, Junan; Warner, Blake; Casto, Bruce C.; Knobloch, Thomas J.; Weghorst, Christopher M.

    2014-01-01

    The prevalence of p16INK4A/CDKN2A genetic alterations in human oral cancers indicates that the p16 gene could be a potent and appropriate target for novel intervention. Chemically induced hamster cheek pouch (HCP) tumors are highly similar to human oral cancers in both histology and genetics and may be a good choice as a surrogate model for human oral cancers. Nevertheless, little is known about the genetic events in the p16 gene in the HCP tumor model. The purpose of this study was to evaluate chemically induced HCP tumor specimens for potential inactivating p16 alterations. HCP tumors were induced with 7, 12-dimethylbenz(a)anthracene (DMBA), and DNA extracted from 34 such specimens were analyzed for homozygous/hemizygous deletions, aberrant methylation of 5’ CpG islands, and point mutations using real-time multiplex PCR, methylation-specific PCR, and direct sequencing/cold single strand conformation polymorphism (SSCP), respectively. Homozygous deletions, hemizygous deletions, aberrant methylation of 5’-CpG islands, and point mutation were identified in 11, 4, 9, and 1 of 34 specimens, respectively. While the overall incidence of p16 alterations was 70.6% (24 of 34 specimens), the majority of inactivating events (67.6%) stemmed from deletion or methylation, which is consistent with the observations that in human oral SCC, the significant p16-inactivating events have been reported to be deletion and methylation. Our results strongly support the use of DMBA-induced HCP tumor model in evaluating novel p16-targeted therapy and prevention of human oral SCC. PMID:18247379

  2. Hepatic dysfunction induced by 7, 12-dimethylbenz(α)anthracene and its obviation with erucin using enzymatic and histological changes as indicators.

    PubMed

    Arora, Rohit; Bhushan, Sakshi; Kumar, Rakesh; Mannan, Rahul; Kaur, Pardeep; Singh, Amrit Pal; Singh, Bikram; Vig, Adarsh P; Sharma, Deepika; Arora, Saroj

    2014-01-01

    The toxicity induced by 7, 12-dimethylbenz(α)anthracene (DMBA) has been widely delineated by a number of researchers. This potent chemical damages many internal organs including liver, by inducing the production of reactive oxygen species, DNA-adduct formation and affecting the activities of phase I, II, antioxidant and serum enzymes. Glucosinolate hydrolytic products like isothiocyanates (ITCs) are well known for inhibiting the DNA-adduct formation and modulating phase I, II enzymes. Sulforaphane is ITC, currently under phase trials, is readily metabolized and inter-converted into erucin upon ingestion. We isolated erucin from Eruca sativa (Mill.) Thell. evaluated its hepatoprotective role in DMBA induced toxicity in male wistar rats. The rats were subjected to hepatic damage by five day regular intraperitoneal doses of DMBA. At the end of the protocol, the rats were euthanized, their blood was collected and livers were processed. The liver homogenate was analyzed for phase I (NADPH-cytochrome P450 reductase, NADH-cytochrome b5 reductase, cytochrome P450, cytochrome P420 and cytochrome b5), phase II (DT diaphorase, glutathione-S-transferase and γ-glutamyl transpeptidase) and antioxidant enzymes (superoxide dismutase, catalase, guaiacol peroxidise, ascorbate peroxidise, glutathione reductase and lactate dehydrogenase). The level of thiobarbituric acid reactive substances, lipid hydroperoxides, conjugated dienes and reduced glutathione in the liver homogenate was also analyzed. The serum was also analyzed for markers indicating hepatic damage (alkaline phosphatase, serum glutamic oxaloacetic transaminase, serum glutamic pyruvic transaminase, direct bilirubin and total bilirubin). Erucin provided significant protection against DMBA induced damage by modulating the phase I, II and antioxidant enzymes. The histological evaluation of liver tissue was also conducted, which showed the hepatoprotective role of erucin.

  3. Degradation of pyrene, benz[a]anthracene, and benzo[a]pyrene by Mycobacterium sp. strain RJGII-135, isolated from a former coal gasification site.

    PubMed

    Schneider, J; Grosser, R; Jayasimhulu, K; Xue, W; Warshawsky, D

    1996-01-01

    The degradation of three polycyclic aromatic hydrocarbons (PAH), pyrene (PYR), benz[a]anthracene (BAA), and benzo[a]pyrene (BaP), by Mycobacterium sp. strain RJGII-135 was studied. The bacterium was isolated from an abandoned coal gasification site soil by analog enrichment techniques and found to mineralize [14C]PYR. Further degradation studies with PYR showed three metabolites formed by Mycobacterium sp. strain RJGII-135, including 4,5-phenanthrene-dicarboxylic acid not previously isolated, 4-phenanthrene-carboxylic acid, and 4,5-pyrene-dihydrodiol. At least two dihydrodiols, 5,6-BAA-dihydrodiol and 10,11-BAA-dihydrodiol, were confirmed by high-resolution mass spectral and fluorescence analyses as products of the biodegradation of BAA by Mycobacterium sp. strain RJGII-135. Additionally, a cleavage product of BAA was also isolated. Mass spectra and fluorescence data support two different routes for the degradation of BaP by Mycobacterium sp. strain RJGII-135. The 7,8-BaP-dihydrodiol and three cleavage products of BaP, including 4,5-chrysene-dicarboxylic acid and a dihydro-pyrene-carboxylic acid metabolite, have been isolated and identified as degradation products formed by Mycobacterium sp. strain RJGII-135. These latter results represent the first example of the isolation of BaP ring fission products formed by a bacterial isolate. We propose that while this bacterium appears to attack only one site of the PYR molecule, it is capable of degrading different sites of the BAA and BaP molecules, and although the sites of attack may be different, the ability of this bacterium to degrade these PAH is well supported. The proposed pathways for biodegradation of these compounds by this Mycobacterium sp. strain RJGII-135 support the dioxygenase enzymatic processes reported previously for other bacteria. Microorganisms like Mycobacterium sp. strain RJGII-135 will be invaluable in attaining the goal of remediation of sites containing mixtures of these PAH.

  4. Chemotherapeutic effect of tangeretin, a polymethoxylated flavone studied in 7, 12-dimethylbenz(a)anthracene induced mammary carcinoma in experimental rats.

    PubMed

    Lakshmi, A; Subramanian, S

    2014-04-01

    Globally, breast cancer is the second most prevalent cancer among women and its incidence is amplifying alarmingly. Since genetics is believed to account for only 10% of the reported cases, the environmental factors including diet are thought to play a significant role in predisposing breast cancer. Many bioactive compounds of plant origin have been reported for their anticancer potential. Tangeretin, a pentamethoxy flavone, is a naturally occurring phytoconstituent found to be present in significant amounts in the peel of citrus fruits. Tangeretin possess a wide array of pharmacological activities such as cytostatic, anti-proliferative and antioxidant properties. In the absence of systemic studies in the literature, the present study was aimed to evaluate the chemotherapeutic potential of tangeretin in 7, 12-dimethyl benz(a)anthracene (DMBA) induced mammary carcinoma in rats. Oral treatment of tangeretin (50 mg/kg BW) to breast tumor bearing rats daily for four weeks was found to be effective against DMBA induced mammary gland carcinogenesis in female Wistar rats. The increased activities of AST, ALT, ALP, ACP, 5'-ND, γ-GT and LDH in serum of control and experimental breast cancer rats were significantly (p < 0.05) decreased to near normal levels. Further, the levels of lipid peroxide (TBARS), enzymatic antioxidants such as SOD, CAT, GPx and non-enzymatic antioxidants such as GSH, Vitamin C, Vitamin E and Phase I (cytochrome P450, cytochrome b5, EROD, MROD and PROD) and Phase II detoxification (glutathione S-transferase (GST), quinone reductase (QR)) were decreased significantly by administration of tangeretin. Immunohistochemical and western blotting studies for estrogen receptor, progesterone receptor and HER2/neu status exemplified the chemotherapeutic effect of tangeretin. Further, the histological and ultrastructural analysis of breast tissues evidenced the anti-tumorigenic nature of tangeretin. Thus, the results of the present study clearly indicate that

  5. Relative induction potency of benzo(a)pyrene and dibenzo(a,h) anthracene in environmental samples using the H4IIE cell bioassay

    SciTech Connect

    Willett, K.; Gardinali, P.; Sericano, J.; Wade, T.; Safe, S.

    1995-12-31

    The induction of ethoxyresorufin O-deethylase (EROD) activity in H4IIE cells has proven to be a useful assay for assessing the toxic equivalents of complex mixtures of halogenated aromatic hydrocarbons and related compounds in environmental samples. However, there is often a discrepancy between bioassay induction results and toxic equivalents calculated from chemical analysis of samples; the former yielding higher I-TEQs (induction/toxic equivalents). Polynuclear aromatic hydrocarbons (PAHs) are a class of chemicals which can significantly contribute to I-TEQ estimates. Benzo(a)pyrene (BAP) and dibenzo(a,h)anthracene (DBA) are both carcinogenic PAHs found in environmental samples, specifically oysters (Crassostrea virginica) collected from Galveston Bay. Dose-response studies were conducted with H4IIE cells to determine the relative induction potency of these two PAHs relative to 2,3,7,8-TCDD. Using probit analysis, the I-TEFs were 0.00144 and 0.0095 for BAP and DBA, respectively. Reconstituted PAH mixtures (744 to 4,466 ng/g total PAHs) with constant percentages of BAP (4.5%) and DEA (3.5%) yielded bioassay derived I-TEQs which ranged from 0.52 to 1.44 ng/g. Oysters treated with the same PAH mix for 30 days differentially accumulated the DBA and BAP over the time course. The bioassay derived I-TEQs of extracts from these oysters ranged from 0.99 to 6.14 ng/g whereas the calculated values using only the I-TEQs of BAP and BDA ranged from 0.04 to 0.57 accounting for only 5--10% of the observed induction response. These results indicate that presence of other PAHs in the treated oyster extracts are highly active as inducers of EROD activity in the H4IIE bioassay.

  6. Protective effect of Operculina turpethum against 7,12-dimethyl benz(a)anthracene induced oxidative stress with reference to breast cancer in experimental rats.

    PubMed

    Anbuselvam, C; Vijayavel, K; Balasubramanian, M P

    2007-07-20

    Reactive oxygen species (ROS) directly or indirectly involves in multistage process of carcinogenesis. Antioxidant activity of methanolic extract of Operculina turpethum stems (MEOT) on 7,12 dimethylbenz(a)anthracene (DMBA) induced breast cancer was investigated in female Sprague-Dawley rats. Changes in the levels of lipid peroxidation and antioxidants system was evaluated in addition to tumour development. Twenty four female rats were divided into four groups: control, DMBA, DMBA+MEOT and MEOT. In the DMBA group, rats were intragastrically administered with 20 mg of DMBA using corn oil as vehicle. Animals of DMBA+MEOT group received a single dose of 20 mg of DMBA dissolved in corn oil intragastrically followed by O. turpethum extract (100 mg/kg body weight), while MEOT group received O. turpethum extract (100 mg/kg body weight) intragastrically daily for a period of 45 days. After the experimental period of 45 days, oxidative stress parameters were assessed in serum, liver and breast of both control and experimental groups. In addition to this, tumour weight of breast was also assessed. A significant increase in lipid peroxidation levels were observed in the tested samples of cancer induced rats while the activities of enzymic antioxidants such as superoxide dismutase (SOD), catalase (CAT), glutathione peroxidase (GPx) and non-enzymic antioxidants like glutathione (GSH), ascorbic acid (Vitamin C) and alpha-tocopherol (Vitamin E) were decreased in cancer-bearing animals when compared to control animals. A significant (P<0.05) increase in the tumour weight was observed in the breast of DMBA group and the breast tumour weight decreased significantly (P<0.05) in the DMBA+MEOT groups. Oral administration of MEOT remarkably reduced the lipid peroxidation activity and increased the antioxidants level in drug treated animals and decreased the tumour weight significantly (P<0.05). This result suggests that MEOT shows antioxidant activity and play a protective role against

  7. Synthesis, characterization and properties of novel blue light emitting discrete π-functional polymer consisting of carbazole and anthracene units and their applications in polymer light emitting diodes

    NASA Astrophysics Data System (ADS)

    Gopal, Ram; Huang, Yi-Chiang; Lee, Hsu-Feng; Chang, Ming-Sien; Huang, Wen-Yao

    2017-03-01

    A new novel blue light emitting polymer containing carbazole and anthracene derivatives has been successfully synthesized via polycondensation chemical reaction of diol and difluoro monomers. An effort has been made to raise the band gap of blue light emitter by lowering the conjugation extent in the backbone. The synthesized blue polymer exhibits decent solubility, good process ability, high thermal stability, high glass transition temperature (272 °C) and the decomposition temperature of 358 °C. The UV-vis absorption spectra and photoluminescence spectra depict that the light emission lies in blue region. The solid state photoluminescence (PL) spectra of the polymer (λPL=456 nm) shows red shift (Δλ = 37 nm) as compared with the corresponding solution PL spectra, presumably due to lower intermolecular distance in solid state. The multi-layered polymer light emitting diode was fabricated, using blue polymer with ITO/PEDOT: PSS/BP/LiF/Al architecture. The luminance-voltage (L-V) and current density-voltage (J-V) curves show a maximum luminance of 7544 cd m-2, a maximum emission efficiency of 4.2 cd A-1, a maximum current density of 453 mA cm-2 at a turn-on voltage of 4.5 V. Moreover, the PLED instigate pure blue EL emission, stable at 436 nm with outstanding CIE coordinates of (x = 0.15, y = 0.08), which is close to the pure NTSC blue coordinates of (0.14, 0.08). [Figure not available: see fulltext.

  8. Synthesis and structure of dimeric anthracene-9-carboxylato bridged dinuclear erbium(III) complex, [Er(2)(9-AC)(6)(DMF)(2)(H(2)O)(2)].

    PubMed

    Kusrini, Eny; Adnan, Rohana; Saleh, Muhammad I; Yan, Lim-Kong; Fun, Hoong-Kun

    2009-05-01

    We study the influence of the bulky aromatic rings, e.g. anthracence-9-carboxylic acid (9-ACA) with a large conjugated pi-system on the structure and spectroscopic properties of [Er(2)(9-AC)(6)(DMF)(2)(H(2)O)(2)] complex where 9-AC=anthracence-9-carboxylato and DMF=N,N'-dimethylformamide. The complex has been prepared from the erbium chloride and 9-ACA in the mixture of H(2)O:DMF solution (4:1, v/v) followed by pH adjustment to 6. The complex is crystallized in a monoclinic system with space group P2(1)/n. The two Er(III) ions are double bridged by the deprotonated carboxyl groups of two 9-AC anions (O1 and O1A), forming an eight-coordination number. The chelating bidentate (O,O), chelating-bridging tridentate (O,O,O') and monodentate of 9-AC anions are observed in the dinuclear [Er(2)(9-AC)(6)(DMF)(2)(H(2)O)(2)] complex. The Er-Er distance is 4.015A in the dimeric unit. Intramolecular O-Hcdots, three dots, centeredO and C-Hcdots, three dots, centeredO hydrogen bonds as well as numerous of intermolecular C-Hcdots, three dots, centeredpi interactions between the anthracene rings by edge-to-face interactions linked the dinuclear dimeric units into two-dimensional supramolecular network in a propeller-arrangement. Electronic absorption spectra of the Er(III) complex and its salt were measured. The emission spectrum of the complex is composed of a broad band due to the emission of intraligand pi*-->pi transition from the 9-AC anions and a shoulder peak originating from the 4f-4f emission transition of the Er(III) ions. The complex has a high thermal stability which can be attributed to the effectively increase the rigidity of the 9-AC anions.

  9. Inhibition of the binding of 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene to DNA in mouse skin epidermis by 1-ethynylpyrene.

    PubMed

    Viaje, A; Lu, J Y; Hopkins, N E; Nettikumara, A N; DiGiovanni, J; Alworth, W L; Slaga, T J

    1990-07-01

    The effects of 1-ethynylpyrene (EP), 1-vinylpyrene (VP) and 2-ethynlnaphthalene (EN) on the covalent binding of 7,12-dimethylbenz[a]anthracene (DMBA) and of benzo[a]-pyrene (B[a]P) to the epidermal DNA in mouse skin were investigated. When applied topically, 5 min before an initiating dose of 10 nmol DMBA or of 200 nmol B[a]P, EP was an effective inhibitor of the formation of the covalent complexes of these procarcinogenic polycyclic aromatic hydrocarbons (PAHs) with the epidermal DNA. VP, applied under the same conditions, was a significantly less effective inhibitor of the binding of DMBA to DNA and showed even weaker inhibition of the binding of B[a]P. EN was ineffective as an inhibitor of the binding of either DMBA or B[a]P. These results establish that both the pyrene nucleus and the ethynyl substituent of EP contribute to the effective inhibition of the binding of DMBA and B[a]P to the epidermal DNA of mouse skin. No significant changes in the ratios of the anti- to the syndiol epoxide-DNA adducts of DMBA or of B[a]P were produced by doses of EP that produced inhibitions of the binding to DNA. At doses of VP that inhibited covalent binding of both DMBA and B[a]P, no changes in DMBA-DNA adduct distributions were observed but changes in the relative proportions of several B[a]P-DNA adducts were noted. These data are discussed in terms of the potential of aryl acetylenes to act as suicide inhibitors (mechanism-based inactivators) of cytochrome P450-dependent monooxygenase isozymes.

  10. Effect of phosphatidylinositol-3 kinase inhibition on ovotoxicity caused by 4-vinylcyclohexene diepoxide and 7, 12-dimethylbenz[a]anthracene in neonatal rat ovaries

    SciTech Connect

    Keating, Aileen F.; Mark, Connie J.; Sen, Nivedita; Sipes, I. Glenn; Hoyer, Patricia B.

    2009-12-01

    4-vinylcyclohexene diepoxide (VCD) is an ovotoxicant that specifically destroys primordial and small primary follicles in the ovaries of mice and rats. In contrast, 7,12-dimethylbenz[a]anthracene (DMBA) is ovotoxic to all ovarian follicle classes. This study investigated phosphatidylinositol-3 kinase signaling involvement in VCD- and DMBA-induced ovotoxicity. Postnatal day (PND) 4 Fischer 344 (F344) rat whole ovaries were cultured for 2-12 days in vehicle control, VCD (30 muM), or DMBA (1 muM), +- PI3 kinase inhibitor LY294002 (20 muM) or its inactive analog LY303511 (20 muM). Following culture, ovaries were histologically evaluated, and healthy follicles were classified and counted. PI3 kinase inhibition had no effect on primordial follicle number, but reduced (P < 0.05) small primary and larger follicles beginning on day 4. VCD caused primordial and small primary follicle loss (P < 0.05) beginning on day 6. With PI3 kinase inhibition, VCD did not affect primordial follicles (P > 0.05) at any time, but did cause loss (P < 0.05) of small primary follicles. DMBA exposure caused primordial and small primary follicle loss (P < 0.05) on day 6. Further, DMBA-induced primordial and small primary follicle loss was greater with PI3 kinase inhibition (P < 0.05) than with DMBA alone. These results support that (1) PI3 kinase mediates primordial to small primary follicle recruitment, (2) VCD, but not DMBA, enhances ovotoxicity by increasing primordial to small primary follicle recruitment, and (3) in addition to xenobiotic-induced ovotoxicity, VCD is also a useful model chemical with which to elucidate signaling mechanisms involved in primordial follicle recruitment.

  11. Growth inhibition of fungus Phycomyces blakesleeanus by anion channel inhibitors anthracene-9-carboxylic and niflumic acid attained through decrease in cellular respiration and energy metabolites.

    PubMed

    Stanić, Marina; Križak, Strahinja; Jovanović, Mirna; Pajić, Tanja; Ćirić, Ana; Žižić, Milan; Zakrzewska, Joanna; Cvetić Antić, Tijana; Todorović, Nataša; Živić, Miroslav

    2017-01-18

    Increasing resistance of fungal strains to known fungicides has prompted identification of new candidates for fungicides among substances previously used for other purposes. We have tested the effects of known anion channel inhibitors anthracene-9-carboxylic (A9C) and niflumic acid (NFA) on growth, energy metabolism and anionic current of mycelium of fungus Phycomyces blakesleeanus. Both inhibitors significantly decreased growth and respiration of mycelium, but complete inhibition was only achieved by 100 or 500 µM NFA, for growth and respiration, respectively. A9C had no effect on respiration of human NCI-H460 cell line, and very little effect on cucumber root sprout clippings, which nominates this inhibitor for further investigation as a potential new fungicide. Effects of A9C and NFA on respiration of isolated mitochondria of P. blakesleeanus were significantly smaller, which indicates that their inhibitory effect on respiration of mycelium is indirect. NMR spectroscopy showed that both A9C and NFA decrease the levels of ATP and polyphosphates in the mycelium of P. blakesleanus, but only A9C caused intracellular acidification. Outwardly rectifying, fast inactivating instantaneous anionic current (ORIC) was also reduced to 33±5% and 21±3% of its pre-treatment size by A9C and NFA, respectively, but only in the absence of ATP. It can be assumed from our results that the regulation of ORIC is tightly linked to cellular energy metabolism in P. blakesleeanus, and the decrease in ATP and polyphosphate levels could be a direct cause of growth inhibition.

  12. Synthesis and photochemical properties of 1,3-di-9-anthryl-2-propanol, 1,3-di-9-anthrylacetone, and related propano-linked anthracenes

    SciTech Connect

    Becker, H.D.; Amin, K.A. )

    1989-06-23

    9-anthryllithium reacts with epichlorohydrin to give 1,3-di-9-anthryl-2-propanol via 3-(9-anthryl)-1-chloro-2-hydroxypropane and 3-(9-anthryl)-1,2-epoxypropane. Oxidation of dianthryl-2-propanol with Dess-Martin reagent gave 1,3-di-9-anthrylacetone. Various other 1,3-bichromophoric anthracenes were synthesized by way of C-methylation of dianthrylacetone, 1,3-di-9-anthryl-1-propanone, and 1,3-di-9-anthrylpropenone. 9-Anthrylacetone, formed as byproduct in the reaction of anthryllithium with epichlorohydrin, was prepared from 9-anthrylacetaldehyde by Grignard reaction with methylmagnesium iodide and subsequent oxidation. The excited-state properties of dianthryl-2-propanol, dianthrylacetone, 1,3-di-9-anthryl-2-methyl-1-propanone, 1,3-di-9-anthryl-2-methyl-2-propanol, diastereomeric 1,3-di-9-anthryl-1-butanols, 1,3-di-9-anthryl-2-butanone, 1,3-di-9-anthryl-1-butanone, and diastereomeric 1,3-di-9-anthryl-2-methyl-1-butanones have been evaluated by fluorescence quantum yields, and by quantum yields for the isomerization by intramolecular 4{pi} + 4{pi} cycloaddition. Dianthryl-2-propanol, 1,3-di-9-antrhyl-2-methyl-2-propanol, dianthrylacetone, diastereomeric 1,3-di-9-anthryl-1-butanols, and 1,3-di-9-anthryl-2-butanone isomerize in their excited singlet state with quantum yields of 0.046, 0.021, 0.25, 0.23, and 0.22, respectively. The photochemical isomerization of those 1,3-bichromophoric anthrancenes which are characterized by a 9-anthroyl chromophore involves the excited triplet state, and the cyclization quantum yield may be as high as 0.72.

  13. Proteomic analysis of the murine liver in response to a combined exposure to psychological stress and 7,12-dimethylbenz(a)anthracene.

    PubMed

    Flint, Melanie S; Hood, Brian L; Sun, Mai; Stewart, Nicolas A; Jones-Laughner, Jacqueline; Conrads, Thomas P

    2010-01-01

    Polycyclic aromatic hydrocarbons (PAHs) are environmental carcinogens implicated to underlie development of several types of cancers. Cytochrome P450 (CYP) enzymes play key roles in the conversion of PAHs to highly potent carcinogens, namely diol epoxides. 7,12-Dimethylbenz(a)anthracene (DMBA), a PAH, is highly carcinogenic, where in mouse models it is known to be responsible for initiating tumor formation in many organs including mammary tissues, ovaries, and skin. Psychological stress, via release of biochemical mediators, can greatly impact carcinogenesis. The present investigation examined the hypothesis that psychological stress modulates metabolism and carcinogenicity of DMBA through alteration of key drug metabolizing enzyme abundance levels in the liver utilizing mass spectrometry-based proteomics. To test this hypothesis, four groups of mice were treated as follows: nonstressed, stressed, nonstressed/DMBA-exposed, and stressed/DMBA-exposed, where the stressor was a well-accepted model of restraint. Liver proteins were extracted, resolved by one-dimensional gel electrophoresis, digested in-gel with trypsin, and analyzed by liquid chromatography-tandem mass spectrometry. This investigation resulted in the unique identification of 59 isoforms of CYP enzymes. Changes in protein abundances derived from spectral counting indicates that stress alone results in increases in the abundance of proteins responsive to oxidative stress, along with Phase I and II metabolizing enzymes, such as CYP2J5 and UDP glucoronytransferases. The proteomic results further indicate that exposure to DMBA induces increases in the abundance of CYP1A2 and serine protease inhibitors and decreases the abundance of CYP4 V3. Finally, significant changes in the abundance of proteins such as CYP1A2, CYP3A11, and Topoisomerase-2 were found between nonstressed and stressed/DMBA-treated mice. These data support the hypothesis that psychological stress modulates DMBA-induced regulation of drug

  14. The enzymatic conjugation of glutathione with bay-region diol-epoxides of benzo[a]pyrene, benz[a]anthracene and chrysene.

    PubMed

    Robertson, I G; Jernström, B

    1986-10-01

    The kinetics of the enzymatic conjugation of glutathione (GSH) with the anti-diastereoisomers of trans-7,8-dihydroxy-9,10-epoxy-7,8,9,10- tetrahydrobenzo[a]pyrene (BPDE), trans-3,4-dihydroxy-1,2-epoxy-1,2,3, 4-tetrahydrobenz[a]anthracene (BADE) and trans-1,2- dihydroxy-3,4-epoxy-1,2,3,4-tetrahydrochrysene (CDE) catalyzed by transferase 4-4 from rat liver have been compared. When the concentration of these diol-epoxides was varied (using 2 mM GSH) the apparent Vmax values were 560, 2100 and 1500 nmol/mg/min for (+/-)-anti-BPDE, (+/-)-anti-BADE and (+/-)-anti-CDE, respectively, with corresponding apparent Km values of 11, 125 and 105 microM. The catalytic efficiency of transferase 4-4 in the GSH conjugation of (+/-)-anti-BADE and (+/-)-anti-CDE is thus approximately one-third of (+/-)-anti-BPDE (0.014 and 0.012 s-1 microM-1 respectively versus 0.042 s-1 microM-1). Similar non-linear Lineweaver-Burk plots were obtained with each diol-epoxide when the concentration of GSH was varied, and two apparent Km values of 0.02-0.04 and 0.4-0.9 mM GSH were estimated. The GSH-conjugates formed with the individual enantiomers of the racemic substrates used were resolved by h.p.l.c. The data indicate that with each diol-epoxide transferase 4-4 is highly selective (greater than or equal to 95%) towards the biologically most active (+)-enantiomer.

  15. Histopathological alterations during breast carcinogenesis in a rat model induced by 7,12-Dimethylbenz (a) anthracene and estrogen-progestogen combinations

    PubMed Central

    Feng, Man; Feng, Chang; Yu, Zhigang; Fu, Qinye; Ma, Zhongbing; Wang, Feng; Wang, Fei; Yu, Lixiang

    2015-01-01

    Studies have shown that the development of breast cancer (BC) is a multi-step process that occurs sequentially from normal to usual hyperplasia, atypical hyperplasia, carcinoma in situ, and finally the invasive stages of carcinoma. Our study investigated the histopathological alterations in breast tissue in a Sprague-Dawley (SD) rat model induced by 7,12-Dimethylbenz (a) anthracene (DMBA) and estrogen-progestogen (E-P). Fifty rats were randomly divided into five groups (n = 10 each) and administered the E-P/DMBA combination. After the induction of BC, breast tissue samples were obtained from the rats and stained with hematoxylin-eosin (HE). Breast tissues from 10 rats and 10 human patients were obtained for comparison. The expression of P63, CK5/6 and CK34βE12 was observed and analyzed using the SPSS 17.0 software. The HE results showed ductal epithelial hyperplasia with forming a second lumen or papillary structure, atypical hyperplasia with atypical proliferative cells, forming a cross-bridge or cribriform structure in breast tissues from the rats samples. The IHC results showed that the expression of P63 was not significantly different between rat and human breast tissue (P > 0.05), but its expression in rat and human tissue was significantly different between UDH, ADH, DCIS and IDC (P < 0.01). A similar trend was observed for the expression of CK5/6 and CK34βE12 too. Thus, the findings in this model may reflect the histopathological changes that occur during the progression of human BC. Therefore, this model could be used for the establishment of BC models to investigate the prevention and treatment of BC. PMID:25785005

  16. Hepatic Dysfunction Induced by 7, 12-Dimethylbenz(α)anthracene and Its Obviation with Erucin Using Enzymatic and Histological Changes as Indicators

    PubMed Central

    Arora, Rohit; Bhushan, Sakshi; Kumar, Rakesh; Mannan, Rahul; Kaur, Pardeep; Singh, Amrit Pal; Singh, Bikram; Vig, Adarsh P.; Sharma, Deepika; Arora, Saroj

    2014-01-01

    The toxicity induced by 7, 12-dimethylbenz(α)anthracene (DMBA) has been widely delineated by a number of researchers. This potent chemical damages many internal organs including liver, by inducing the production of reactive oxygen species, DNA-adduct formation and affecting the activities of phase I, II, antioxidant and serum enzymes. Glucosinolate hydrolytic products like isothiocyanates (ITCs) are well known for inhibiting the DNA-adduct formation and modulating phase I, II enzymes. Sulforaphane is ITC, currently under phase trials, is readily metabolized and inter-converted into erucin upon ingestion. We isolated erucin from Eruca sativa (Mill.) Thell. evaluated its hepatoprotective role in DMBA induced toxicity in male wistar rats. The rats were subjected to hepatic damage by five day regular intraperitoneal doses of DMBA. At the end of the protocol, the rats were euthanized, their blood was collected and livers were processed. The liver homogenate was analyzed for phase I (NADPH-cytochrome P450 reductase, NADH-cytochrome b5 reductase, cytochrome P450, cytochrome P420 and cytochrome b5), phase II (DT diaphorase, glutathione-S-transferase and γ-glutamyl transpeptidase) and antioxidant enzymes (superoxide dismutase, catalase, guaiacol peroxidise, ascorbate peroxidise, glutathione reductase and lactate dehydrogenase). The level of thiobarbituric acid reactive substances, lipid hydroperoxides, conjugated dienes and reduced glutathione in the liver homogenate was also analyzed. The serum was also analyzed for markers indicating hepatic damage (alkaline phosphatase, serum glutamic oxaloacetic transaminase, serum glutamic pyruvic transaminase, direct bilirubin and total bilirubin). Erucin provided significant protection against DMBA induced damage by modulating the phase I, II and antioxidant enzymes. The histological evaluation of liver tissue was also conducted, which showed the hepatoprotective role of erucin. PMID:25390337

  17. Derivation of transplantable 7,12-dimethylbenz(a)anthracene-induced chicken fibrosarcoma lines: differences in metastasizing properties and organ specificity

    SciTech Connect

    Galton, J.E.; Xue, B.; Hochwald, G.M.; Thorbecke, G.J.

    1982-08-01

    Transplantable 7,12-dimethylbenz(a)anthracene-induced SC chicken fibrosarcoma (CHCT-NYU) lines were studied for their ability to grow in internal organs after iv injection (artificial metastases) into 1- to 3-week-old chickens. Some tumor lines were recently derived, whereas others were studied after many serial subcutaneous transplantations. Artificial metastases were seen in the stomach, pancreas, lungs, heart, and muscle, and occasionally in the kidneys and liver. Agammaglobulinemic recipients showed more extensive organ involvement than normal recipients of the same age. Whole-body ..gamma..-irradiation enhanced the incidence of artificial metastases, particularly in lungs. Antibody from the serum of a primary tumor-bearing host reduced the growth of the corresponding tumor in many organs. The metastatic pattern of line CHCT-NYU4 was a relatively stable property. However, intravenous transplantation of tumor cells from line CHCT-NYU4 taken from the liver, lungs, and pancreas of a single recipient established sublines with changes in organ specificity. After a few such serial transplants of liver-derived tumor, a line was derived that grew virtually in the liver alone. A subline with preference for growth in lungs was also obtained, but its ability to grow in the pancreas persisted. A pancreas-derived tumor line also grew in the liver and lungs. Subcutaneous transplants of tissue fragments of the lung-derived tumor line caused the appearance of spontaneous metastases in lungs. The incidence of spontaneous metastases with the lung-derived line was much greater than that with the liver-derived line or with the original CHCT-NYU4 line.

  18. Target cells for cytochrome p450-catalysed irreversible binding of 7,12-dimethylbenz[a]anthracene (DMBA) in rodent adrenal glands.

    PubMed

    Lindhe, Orjan; Granberg, Lizette; Brandt, Ingvar

    2002-08-01

    7,12-Dimethylbenz[a]anthracene (DMBA) is an adrenocorticolytic agent that causes apoplexy (haemorrhage) and massive necrosis in the adrenal cortex in rat. Several explanations regarding the origin of toxicity have been proposed. Huggins and Morii (J Exp Med 114:741-60, 1961) suggested that the cells of the inner adrenal cortex are the primary target, whereas Horváth and Kovács (Pathol Eur 8:43-59, 1973) suggested the vascular endothelium as being the origin of toxicity. In the present study, cultured precision-cut tissue slices were used to localize target cells for irreversible [(3)H]DMBA binding in rat and mouse adrenal cortex. The sites of binding were confirmed by autoradiography in vivo. Irreversible [(3)H]DMBA binding was confined to zona fasciculata/reticularis cells in rat (but not in mouse) adrenal cortex. Pronounced binding was observed in clusters of cells (focal binding), localized predominantly in zona reticularis of rat. [(3)H]DMBA binding in zona fasciculata/reticularis cells was inhibited by the cytochrome p450 1A/B (CYP1A/B) inhibitors ellipticine, alpha-naphthoflavone, and 1-ethynylpyrene. The CYP11B1-inhibitor metyrapone did not reduce [(3)H]DMBA binding. In CYP1-induced (PCB 126-treated) rats and mice, intense irreversible [(3)H]DMBA binding was found also in endothelial cells of the adrenal cortex. The endothelial binding was abolished by the CYP1 inhibitors but remained unaffected by metyrapone. We conclude that the metabolic activation in adrenal parenchymal cells is presumably catalysed by CYP1B1, whereas CYP1A1 presumably catalyses the activation in endothelial cells. We suggest that the adrenocorticolytic effect of DMBA is the result of a dual mode of action, targeting both endothelial and parenchymal cells in the rat adrenal cortex.

  19. Biochemical modulation of cell energy by 2-deoxyglucose and malonate in 7,12-dimethylbenz(a)anthracene-induced carcinogenesis in rats.

    PubMed

    Moselhy, Said S; Kumosani, T A; Al-Malki, A L; Naif, Almalki A

    2015-04-01

    The goal of this study was to explore the impact of 2-deoxglucose or malonate individually or in combination on the level of cell energy (adenosine-5'-triphosphate) and oxidative stress in 7,12-dimethylbenz(a)anthracene (DMBA)-induced mammary proliferation in rats. A total of 60 adult female Sprague Dawley rats were randomly divided into five groups (12 rats each): group I serves as the control group. Rats in groups (II-V) were administrated intragastrically a single dose of 50 mg/kg body weight (bw) of DMBA. A day after DMBA administration, rats in group III were injected intraperitoneally (ip) with 100 mg 2-deoxyglucose (2-DG)/kg bw daily. Rats in group IV were injected ip with 10 mg sodium malonate/kg bw daily. Rats in group V were injected ip with 100 mg 2-DG/kg bw and 10 mg sodium malonate/kg bw (treatment for 90 days). The results obtained showed that DMBA induced oxidative stress by decreasing the activities of glutathione reductase (GRase) and superoxide dismutase (SOD), glutathione peroxidase (GPx) and elevating the levels of malondialdehyde (MDA) and nitric oxide (NO) in mammary tissues when compared with control. The combined treatment protected against the previous deleterious changes by a significant elevation in the activities of GRase and SOD, GPx and lowering the levels of MDA and NO more potentially when compared with individual treatment. Apoptosis, as indicated by a significant release of cytochrome c from mitochondria into the cytosol, observed in DMBA-injected rats was positively significantly correlated with the elevation of the level of NO. These data explained the possible additive effect of 2-DG and malonate by depleting the cell energy by their protective effects against the earlier stages of carcinogenesis.

  20. Chemopreventive effects of Furan-2-yl-3-pyridin-2-yl-propenone against 7,12-dimethylbenz[a]anthracene-inducible genotoxicity

    SciTech Connect

    Hwang, Yong Pil; Han, Eun Hee; Choi, Jae Ho; Kim, Hyung Gyun; Lee, Kyung Jin; Jeong, Tae Cheon; Lee, Eung Seok; Jeong, Hye Gwang

    2008-05-01

    1-Furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) is an anti-inflammatory agent with a propenone moiety and chemically synthesized recently. In this study, we examined the chemopreventive effect of FPP-3 on 7,12-dimethylbenz[a]anthracene (DMBA)-induced genotoxicity in MCF-7 cells. FPP-3 reduced the formation of the DMBA-DNA adduct. DMBA-induced CYP1A1 and CYP1B1 gene expression and enzyme activity were inhibited by FPP-3. It inhibited DMBA-induced aryl hydrocarbon receptor (AhR) transactivation and DMBA-inducible nuclear localization of the AhR. Induction of detoxifying phase II genes by chemopreventive agents represents a coordinated protective response against oxidative stress and neoplastic effects of carcinogens. Transcription factor NF-E2 related factor 2 (Nrf2) regulates antioxidant response element (ARE) of phase II detoxifying and antioxidant enzymes, such as glutathione S-transferase (GST) and NAD(P)H:quinone oxidoreductase (QR). FPP-3 increased the expression and enzymatic activity of GST and QR. Moreover, FPP-3 increased transcriptional activity of GST and QR. GST and QR induction and Nrf2 translocation by FPP-3 were blocked by the PKC inhibitor Goe6983, and the p38 inhibitor SB203580. These results reflected a partial role of PKC{delta} and p38 signaling in FPP-3-mediated GSTA and QR induction through nuclear translocation of Nrf2. Classically, chemopreventive agents either inhibit CYP metabolizing enzyme or induce phase II detoxifying enzymes. These results suggest that FPP-3 has a potent protective effect against DMBA-induced genotoxicity through modulating phase I and II enzymes and that it has potential as a chemopreventive agent.

  1. Involvement of retrotransposition of long interspersed nucleotide element-1 in skin tumorigenesis induced by 7,12-dimethylbenz[a]anthracene and 12-O-tetradecanoylphorbol-13-acetate.

    PubMed

    Okudaira, Noriyuki; Goto, Motohito; Yanobu-Takanashi, Rieko; Tamura, Masato; An, Akihiro; Abe, Yukiko; Kano, Shigeyuki; Hagiwara, Shotaro; Ishizaka, Yukihito; Okamura, Tadashi

    2011-11-01

    Tumor development induced by 7,12-dimethylbenz[a]anthracene (DMBA) plus 12-O-tetradecanoylphorbol-13-acetate (TPA) is a well-characterized model of multistep carcinogenesis. DMBA mutates the Ha-ras gene, whereas TPA promotes the growth of transformed cells by activating cellular signaling molecules. It remains to be clarified how repeated TPA treatment endows transformed cells with autonomous cell growth. Long interspersed nucleotide element-1 (L1) is an endogenous retroelement, and 80-100 copies of L1 function as autonomous mobile elements. Although the L1 retrotransposition (RTP) has been found in various human tumors, implying the possible mobility of L1 during carcinogenesis, little is known about how L1-RTP arises in tumor cells, owing to a lack of experimental models. To dissect the mechanism of L1-RTP during carcinogenesis, we established a line of transgenic mice carrying human L1 and enhanced green fluorescent protein (hL1-EGFP mice) and subjected them to DMBA/TPA-induced skin tumorigenesis. Of 15 skin tumors examined, 13 were positive for L1-RTP; L1-RTP was not detected in normal skin tissues adjacent to the tumors. Moreover, nine L1-RTP-positive tumors were positive for activated Ha-ras, and immunohistochemical analysis revealed cells positive for both L1-RTP and phosphorylated Stat3, a marker of tumor cells. Additional in vivo experiments suggested that L1-RTP occurred during tumor promotion by TPA. This is the first report on the involvement of L1-RTP in chemical carcinogenesis. We propose hL1-EGFP mice as a versatile system for investigating the mode of L1-RTP in tumor development and discuss the possible role of L1-RTP in tumorigenesis.

  2. Embryotoxic effects of benzo[a]pyrene, chrysene and 7,12-dimethylbenz[a]-anthracene in petroleum hydrocarbon mixtures in mallard ducks

    USGS Publications Warehouse

    Hoffman, D.J.; Gay, M.L.

    1981-01-01

    Studies with different avian species have revealed that surface applications of microliter amounts of some crude and fuel oils that coat less than 70% of the egg surface result in considerable reduction in hatching with teratogenicity and stunted growth. Other stUdies have shown that the embryo toxicity is dependent on the aromatic hydrocarbon content, further suggesting that the toxicity is due to causes other than asphyxia. In the present study the effects of three polycyclic aromatic hydrocarbons identified in petroleum were examined on mallard (Anas platyrhynchos) embryo development. Addition of benzo[a]pyrene (BaP), chrysene, or 7,7 2-dimethylbenz[ a]anthracene (DMBA) to a synthetic petroleum hydrocarbon mixture of known composition and relatively low embryotoxicity resulted in embryo toxicity that was enhanced or equal to that of crude oil when 10 :I was applied externally to eggs at 72 h of development. The order of ability to enhance embryo toxicity was DMBA > BaP > chrysene. The temporal pattern of embryonic death was similar to that reported after exposure to crude oil, with additional mortality occurring after outgrowth of the chorioallantois. Retarded growth, as reflected by embryonic body weight, crown-rump length, and bill length, was accompanied by teratogenicity. Abnormal embryos exhibited extreme stunting; eye, brain, and bill defects; and incomplete ossification. Gas chromatographic-mass spectral analysis of externally treated eggs showed the passage of aromatic hydrocarbons including chrysene through the shell and shell membranes to the developing embryos. These findings suggest that the presence of polycyclic aromatic hydrocarbons in petroleum, including BaP, chrysene, and DMBA, significantly enhances the overall embryotoxicity in avian species.

  3. Impact of obesity on 7,12-dimethylbenz[a]anthracene-induced altered ovarian connexin gap junction proteins in female mice

    SciTech Connect

    Ganesan, Shanthi Nteeba, Jackson Keating, Aileen F.

    2015-01-01

    The ovarian gap junction proteins alpha 4 (GJA4 or connexin 37; CX37), alpha 1 (GJA1 or connexin 43; CX43) and gamma 1 (GJC1 or connexin 45; CX45) are involved in cell communication and folliculogenesis. 7,12-dimethylbenz[a]anthracene (DMBA) alters Cx37 and Cx43 expression in cultured neonatal rat ovaries. Additionally, obesity has an additive effect on DMBA-induced ovarian cell death and follicle depletion, thus, we investigated in vivo impacts of obesity and DMBA on CX protein levels. Ovaries were collected from lean and obese mice aged 6, 12, 18, or 24 wks. A subset of 18 wk old mice (lean and obese) were dosed with sesame oil or DMBA (1 mg/kg; ip) for 14 days and ovaries collected 3 days thereafter. Cx43 and Cx45 mRNA and protein levels decreased (P < 0.05) after 18 wks while Cx37 mRNA and protein levels decreased (P < 0.05) after 24 wks in obese ovaries. Cx37 mRNA and antral follicle protein staining intensity were reduced (P < 0.05) by obesity while total CX37 protein was reduced (P < 0.05) in DMBA exposed obese ovaries. Cx43 mRNA and total protein levels were decreased (P < 0.05) by DMBA in both lean and obese ovaries while basal protein staining intensity was reduced (P < 0.05) in obese controls. Cx45 mRNA, total protein and protein staining intensity level were decreased (P < 0.05) by obesity. These data support that obesity temporally alters gap junction protein expression and that DMBA-induced ovotoxicity may involve reduced gap junction protein function. - Highlights: • Ovarian gap junction proteins are affected by ovarian aging and obesity. • DMBA exposure negatively impacts gap junction proteins. • Altered gap junction proteins may contribute to infertility.

  4. Do nonbonded H--H interactions in phenanthrene stabilize it relative to anthracene? A possible resolution to this question and its implications for ligands such as 2,2'-bipyridyl.

    PubMed

    Hancock, Robert D; Nikolayenko, Igor V

    2012-08-23

    The problem of whether interactions between the hydrogen atoms at the 1,10-positions in the "cleft" of the "bent" phenanthrene stabilize the latter molecule thermodynamically relative to "linear" anthracene, or whether the higher stability of phenanthrene is due to a more energetically favorable π-system, is considered. DFT calculations at the X3LYP/cc-pVTZ(-f)++ level of the ground state energies (E) of anthracene, phenanthrene, and the set of five benzoquinolines are reported. In the gas phase, "bent" phenanthrene was computed to be thermodynamically more stable than "linear" anthracene by -28.5 kJ mol(-1). This fact was attributed predominantly to the phenomenon of higher aromatic stabilization of the π-system of phenanthrene relative to anthracene, and not to the stabilizing influence of the nonbonding H--H interactions in its cleft. In fact, these interactions in phenanthrene were shown to be destabilizing. Similar calculations for five benzoquinolines (bzq) indicate that ΔE values vary as: 6,7-bzq (linear) ≤ 2,3-bzq (linear) < 5,6-bzq (bent) ≤ 3,4-bzq (bent) < 7,8-bzq (bent, no H--H nonbonding interactions in cleft), supporting the idea that it is a more stable π-system that favors 7,8-bzq over 2,3-bzq and 6,7-bzq, and that the H--H interactions in the clefts of 3,4-bzq and 5,6-bzq are destabilizing. Intramolecular hydrogen bonding in the cleft of 7,8-bzq plays a secondary role in its stabilization relative 6,7-bzq. The question of whether H--H nonbonded interactions between H atoms at the 3 and 3' positions of 2,2'-bipyridyl (bpy) coordinated to metal ions are stabilizing or destabilizing is then considered. The energy of bpy is scanned as a function of N-C-C-N torsion angle (χ) in the gas-phase, and it is found that the trans form is 32.8 kJ mol(-1) more stable than the cis conformer. A relaxed coordinate scan of energy of bpy in aqueous solution as a function of χ is modeled using the PBF approach, and it is found that the trans conformer is

  5. Oxalate Ester Chemiluminescence, Improved Low Temperature Formulations.

    DTIC Science & Technology

    1985-05-01

    phenylethynyl)anthracene ( BPEA ) and 1-chloro-9,10-bis- (phenylethynyl)anthracene (C1BPEA) were purchased from the American Cyanamid Company. 2-Ethyl...results of Figure 2 also suggest an electronic effect in the fluorescer reaction rate: the electron-donating methyl and ethyl sub- stituents on BPEA ...show increased rates, while the electron-withdrawing chloro group slows the reaction. BPEA , itself, was not included in the study due to poor solubility

  6. 1-[(Anthracen-9-yl)carbon-yl]-2,7-di-meth-oxy-naphthalene: a chain-like structure composed of face-to-face type dimeric mol-ecular aggregates.

    PubMed

    Siqingaowa; Tsumuki, Takehiro; Ogata, Kazuki; Yonezawa, Noriyuki; Okamoto, Akiko

    2016-12-01

    The asymmetric unit of the title compound, C27H20O3, contains two independent mol-ecules (A and B). The anthracene ring system is connected to the 2,7-di-meth-oxy-naphthalene core in a twisted manner, with dihedral angles of 86.38 (5) and 79.36 (8)°, respectively, for conformers A and B. In the crystal, face-to-face type dimeric mol-ecular aggregates of each conformer are observed. The dimer of conformer A is formed by two pairs of C-H⋯π inter-actions, and that of conformer B by a pair of (sp(2))C-H⋯O hydrogen bonds. The dimers of conformer A are linked to each other via a π-π stacking inter-action between the anthracene rings to form a chain along the b axis and the chains are aligned along the c axis, forming a sheet structure. The dimers of conformer B are connected to each other via a couple of C-H⋯π inter-actions to form a chain along the b axis. The chains are aligned along the c axis through (sp(2))C-H⋯O=C hydrogen bonds, forming a sheet parallel to the bc plane. The sheets of conformers A and B are alternately stacked along the a axis via two kinds of inter-molecular (sp(2))C-H⋯O=C hydrogen bonds.

  7. A femtosecond study of the anomaly in electron injection for dye-sensitized solar cells: the influence of isomerization employing Ru(II) sensitizers with anthracene and phenanthrene ancillary ligands.

    PubMed

    Cheema, Hammad; Younts, Robert; Ogbose, Louis; Gautam, Bhoj; Gundogdu, Kenan; El-Shafei, Ahmed

    2015-01-28

    In this study, an intriguing difference caused by structural isomerization based on anthracene and phenanthrene stilbazole type ancillary ligands in Ru(ii) sensitizers for dye sensitized solar cells (DSCs) has been investigated using femtosecond transient absorption spectroscopy. Both anthracene and phenanthrene based sensitizers HD-7 and HD-8, respectively, resulted in a similar extinction coefficient, photophysical and thermodynamic free energy of electron injection and dye regeneration as measured by UV-Vis, excited state lifetime and cyclic voltammetry measurements, respectively. However, TiO2 adsorbed HD-7 resulted in up to 45% less photocurrent density than HD-8 although photovoltage was similar owing to comparable thermodynamic characteristics. It was obvious from the measurement of incident photon to current conversion efficiency (IPCE) that excited electrons in HD-7 are prone to internal energy loss before injection into the TiO2 conduction band. Analysis of photo-induced spectral features measured by femtosecond transient absorption spectroscopy showed that excited electrons in HD-7 are prone to ISC (intersystem crossing) much more than HD-8 and those triplet electrons are not injected into TiO2 efficiently. Interestingly, from impedance measurements, HD-7 showed higher recombination resistance than HD-8 and N719, but a shorter lifetime for electrons injected into the TiO2 conduction band.

  8. Acute 7,12-dimethylbenz[a]anthracene exposure causes differential concentration-dependent follicle depletion and gene expression in neonatal rat ovaries

    SciTech Connect

    Madden, Jill A.; Hoyer, Patricia B.; Devine, Patrick J.; Keating, Aileen F.

    2014-05-01

    Chronic exposure to the polycyclic aromatic hydrocarbon 7,12-dimethylbenz[a]anthracene (DMBA), generated during combustion of organic matter including cigarette smoke, depletes all ovarian follicle types in the mouse and rat, and in vitro models mimic this effect. To investigate the mechanisms involved in follicular depletion during acute DMBA exposure, two concentrations of DMBA at which follicle depletion has (75 nM) and has not (12.5 nM) been observed were investigated. Postnatal day four F344 rat ovaries were maintained in culture for four days before a single exposure to vehicle control (1% DMSO; CT) or DMBA (12 nM; low-concentration or 75 nM; high-concentration). After four or eight additional days of culture, DMBA-induced follicle depletion was evaluated via follicle enumeration. Relative to control, DMBA did not affect follicle numbers after 4 days of exposure, but induced large primary follicle loss at both concentrations after 8 days; while, the low-concentration DMBA also caused secondary follicle depletion. Neither concentration affected primordial or small primary follicle number. RNA was isolated and quantitative RT-PCR performed prior to follicle loss to measure mRNA levels of genes involved in xenobiotic metabolism (Cyp2e1, Gstmu, Gstpi, Ephx1), autophagy (Atg7, Becn1), oxidative stress response (Sod1, Sod2) and the phosphatidylinositol 3-kinase (PI3K) pathway (Kitlg, cKit, Akt1) 1, 2 and 4 days after exposure. With the exception of Atg7 and cKit, DMBA increased (P < 0.05) expression of all genes investigated. Also, BECN1 and pAKT{sup Thr308} protein levels were increased while cKIT was decreased by DMBA exposure. Taken together, these results suggest an increase in DMBA bioactivation, add to the mechanistic understanding of DMBA-induced ovotoxicity and raise concern regarding female low concentration DMBA exposures. - Highlights: • Acute DMBA exposures induce large primary and/or secondary follicle loss. • Acute DMBA exposure did not impact

  9. Inhibitory effects of combination of lycopene and genistein on 7,12- dimethyl benz(a)anthracene-induced breast cancer in rats.

    PubMed

    Sahin, Kazim; Tuzcu, Mehmet; Sahin, Nurhan; Akdemir, Fatih; Ozercan, Ibrahim; Bayraktar, Soley; Kucuk, Omer

    2011-11-01

    Breast cancer is one of the most common cancers in women. Carotenoids and soy isoflavones have been postulated to have breast cancer preventive effects. We investigated the potential preventive effects of lycopene and genistein, alone and in combination, on breast cancer development in female Wistar rats treated with 7,12-dimethylbenz[a]anthracene (DMBA), a carcinogen known to induce breast tumors. Mammary carcinogenesis was initiated by a single, oral gavage of DMBA (80 mg/kg body weight) at 55 days of animal age. Fifty female Wistar rats were divided into 5 experimental groups having 10 animals per group: Group 1 (normal control), Group 2 (DMBA control), Group 3 (DMBA + lycopene), Group 4 (DMBA + genistein), and Group 5 (DMBA + lycopene and genistein). Rats were fed either lycopene (20 mg /kg bw) or genistein (2 mg /kg bw) by oral gavage (3 times per week) starting 2 wk prior to DMBA injection. Treatment was continued for 20 wk. Rats treated with DMBA developed mammary tumors with 100% tumor incidence during the 20-wk study. Inhibition of mammary cancer incidence by lycopene (70%), genistein (60%) and their combination (40%) was observed. Tumor weight decreased by 48%, 61%, and 67%, and mean tumor volume decreased by 18%, 35%, and 65% with lycopene, genistein, and lycopene + genistein, respectively (P < 0.01 for the combination). The proportions of adenocarcinoma masses decreased with lycopene and genistein combination (P < 0.05). Administration of lycopene and genistein combination suppressed breast cancer development and was associated with a decrease in MDA, 8-isoprostane, and 8-OhdG levels and with an increase in serum lycopene and genistein levels. Animals administered DMBA developed breast cancer, which was associated with increased expression of Bcl-2 and decreased expression of Bax, caspase 3, and caspase 9 in mammary tissues. Administration of genistein and lycopene in combination was more effective in inhibiting DMBA-induced breast tumors and modulating

  10. Degradation of pyrene, benz[a]anthracene, and benzo[a]pyrene by Mycobacterium sp. strain RJGII-135, isolated from a former coal gasification site.

    PubMed Central

    Schneider, J; Grosser, R; Jayasimhulu, K; Xue, W; Warshawsky, D

    1996-01-01

    The degradation of three polycyclic aromatic hydrocarbons (PAH), pyrene (PYR), benz[a]anthracene (BAA), and benzo[a]pyrene (BaP), by Mycobacterium sp. strain RJGII-135 was studied. The bacterium was isolated from an abandoned coal gasification site soil by analog enrichment techniques and found to mineralize [14C]PYR. Further degradation studies with PYR showed three metabolites formed by Mycobacterium sp. strain RJGII-135, including 4,5-phenanthrene-dicarboxylic acid not previously isolated, 4-phenanthrene-carboxylic acid, and 4,5-pyrene-dihydrodiol. At least two dihydrodiols, 5,6-BAA-dihydrodiol and 10,11-BAA-dihydrodiol, were confirmed by high-resolution mass spectral and fluorescence analyses as products of the biodegradation of BAA by Mycobacterium sp. strain RJGII-135. Additionally, a cleavage product of BAA was also isolated. Mass spectra and fluorescence data support two different routes for the degradation of BaP by Mycobacterium sp. strain RJGII-135. The 7,8-BaP-dihydrodiol and three cleavage products of BaP, including 4,5-chrysene-dicarboxylic acid and a dihydro-pyrene-carboxylic acid metabolite, have been isolated and identified as degradation products formed by Mycobacterium sp. strain RJGII-135. These latter results represent the first example of the isolation of BaP ring fission products formed by a bacterial isolate. We propose that while this bacterium appears to attack only one site of the PYR molecule, it is capable of degrading different sites of the BAA and BaP molecules, and although the sites of attack may be different, the ability of this bacterium to degrade these PAH is well supported. The proposed pathways for biodegradation of these compounds by this Mycobacterium sp. strain RJGII-135 support the dioxygenase enzymatic processes reported previously for other bacteria. Microorganisms like Mycobacterium sp. strain RJGII-135 will be invaluable in attaining the goal of remediation of sites containing mixtures of these PAH. PMID:8572690

  11. Potent inhibitory effects of suicide inhibitors of P450 isozymes on 7,12-dimethylbenz[a]anthracene and benzo[a]pyrene initiated skin tumors.

    PubMed

    Alworth, W L; Viaje, A; Sandoval, A; Warren, B S; Slaga, T J

    1991-07-01

    A single dose of 1-ethynylpyrene (EP), 1-vinylpyrene (VP) or 2-ethynylnaphthalene (EN) was applied to the skin of SENCAR mice 5 min before an initiating dose of 7,12-dimethylbenz[a]anthracene (DMBA) or benzo[a]pyrene (B[a]P) and the development of skin tumors then promoted with biweekly topical applications of 12-O-tetradecanoylphorbol-13-acetate (TPA). The application of EP strongly inhibited the formation of skin tumors initiated by either DMBA or B[a]P in a dose-dependent manner. Application of 44 pmol of EP inhibited tumor initiation by 10 nmol of DMBA approximately 25%; application of 440 nmol of EP inhibited tumor initiation by 200 nmol of B[a]P approximately 51%. A high single dose of EP (4.4-44 mumol) nearly eliminated skin tumor initiation by either 10 nmol of DMBA or 200 nmol of B[a]P. Application of VP also inhibited the formation of skin tumors initiated by either DMBA or B[a]P in a dose-dependent manner, but higher doses of VP than of EP were required to produce comparable inhibitions. Application of 44 nmol of VP inhibited tumor initiation by 10 nmol of DMBA approximately 30%; application of 4.4 mumol of VP inhibited tumor initiation by 200 nmol of B[a]P approximately 56%. Application of EN yielded contrasting results. EN inhibited the formation of skin tumors initiated by 10 nmol of DMBA, but the observed dose-dependence was minimal; tumors were decreased about 40% by 3.3 mumol of EN and only about 65% by 132 mumol of EN. A high single dose of EN (132 mumol) increased both the mean number of tumors per mouse and the percentage of mice that developed tumors after initiation by 200 nmol of B[a]P. Topical application of 4.4 mumol of EP, 22 mumol of VP or 33 mumol of EN to the skin of SENCAR mice 5 min before a single initiation dose of 2.5 mumol of N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) had a minimal inhibitory effect (14-28%) on the development of skin tumors produced by subsequent biweekly promotion with TPA. A single dose of 44 mumol of EP or

  12. 9-Anthracene carboxylic acid is more suitable than DIDS for characterization of calcium-activated chloride current during canine ventricular action potential.

    PubMed

    Váczi, Krisztina; Hegyi, Bence; Ruzsnavszky, Ferenc; Kistamás, Kornél; Horváth, Balázs; Bányász, Tamás; Nánási, Péter P; Szentandrássy, Norbert; Magyar, János

    2015-01-01

    Understanding the role of ionic currents in shaping the cardiac action potential (AP) has great importance as channel malfunctions can lead to sudden cardiac death by inducing arrhythmias. Therefore, researchers frequently use inhibitors to selectively block a certain ion channel like 4,4'-diisothiocyanostilbene-2,2'-disulfonic acid (DIDS) and 9-anthracene carboxylic acid (9-AC) for calcium-activated chloride current (ICl(Ca)). This study aims to explore which blocker is preferable to study ICl(Ca). Whole-cell voltage-clamp technique was used to record ICa,L, IKs, IKr and IK1, while action potentials were measured using sharp microelectrodes. DIDS- (0.2 mM) and 9-AC-sensitive (0.5 mM) currents were identical in voltage-clamp conditions, regardless of intracellular Ca(2+) buffering. DIDS-sensitive current amplitude was larger with the increase of stimulation rate and correlated well with the rate-induced increase of calcium transients. Both drugs increased action potential duration (APD) to the same extent, but the elevation of the plateau potential was more pronounced with 9-AC at fast stimulation rates. On the contrary, 9-AC did not influence either the AP amplitude or the maximal rate of depolarization (V max), but DIDS caused marked reduction of V max. Both inhibitors reduced the magnitude of phase-1, but, at slow stimulation rates, this effect of DIDS was larger. All of these actions on APs were reversible upon washout of the drugs. Increasing concentrations of 9-AC between 0.1 and 0.5 mM in a cumulative manner gradually reduced phase-1 and increased APD. 9-AC at 1 mM had no additional actions upon perfusion after 0.5 mM. The half-effective concentration of 9-AC was approximately 160 μM with a Hill coefficient of 2. The amplitudes of ICa,L, IKs, IKr and IK1 were not changed by 0.5 mM 9-AC. These results suggest that DIDS is equally useful to study ICl(Ca) during voltage-clamp but 9-AC is superior in AP measurements for studying the physiological role of

  13. Evaluation of ovotoxicity induced by 7, 12-dimethylbenz[a]anthracene and its 3,4-diol metabolite utilizing a rat in vitro ovarian culture system

    SciTech Connect

    Igawa, Yoshiyuki; Keating, Aileen F. Rajapaksa, Kathila S.; Sipes, I. Glenn; Hoyer, Patricia B.

    2009-02-01

    The polycyclic aromatic hydrocarbon 7, 12-dimethylbenz[a]anthracene, (DMBA), targets and destroys all follicle types in rat and mouse ovaries. DMBA requires bioactivation to DMBA-3,4-diol-1,2-epoxide for ovotoxicity via formation of the intermediate, DMBA-3,4-diol (catalyzed by microsomal epoxide hydrolase; mEH). mEH was shown to be involved in DMBA bioactivation for ovotoxicity induction in B6C3F{sub 1} mouse ovaries. The current study compared DMBA and DMBA-3,4-diol mediated ovotoxicity, and investigated mEH involvement in DMBA-3,4-diol bioactivation in Fischer 344 (F344) rat ovary. F344 postnatal day (PND) 4 rat ovaries were cultured in vehicle control or media containing 1) DMBA or DMBA-3,4-diol (12.5 nM - 1 {mu}M; 15 days); 2) DMBA (1 {mu}M; 6 h - 15 days); and 3) DMBA (1 {mu}M) or DMBA-3,4-diol (75 nM) {+-} the mEH activity inhibitor cyclohexene oxide (CHO; 2 mM; 4 days). Ovaries were histologically evaluated and mEH mRNA and protein were measured by reverse transcriptase PCR or Western blotting, respectively. Ovotoxicity following 15 days of culture occurred (P < 0.05) at lower concentrations of DMBA-3,4-diol (12.5 nM - primordial; 75 nM - primary) than DMBA (75 nM - primordial; 375 nM - primary). The temporal pattern of mEH expression following DMBA exposure showed mRNA up-regulation (P < 0.05) on day 2, with increased protein (P < 0.05) on day 4, the earliest time of observed follicle loss (P < 0.05). mEH inhibition prevented DMBA-induced, but not DMBA-3,4-diol-induced ovotoxicity. These results demonstrate a conserved response in mice and rats for ovarian mEH involvement in DMBA bioactivation to its ovotoxic, 3,4-diol-1,2-epoxide form.

  14. Oral administration of the citrus coumarin, isopimpinellin, blocks DNA adduct formation and skin tumor initiation by 7,12-dimethylbenz[a]anthracene in SENCAR mice.

    PubMed

    Kleiner, Heather E; Vulimiri, Suryanarayana V; Starost, Matthew F; Reed, Melissa J; DiGiovanni, John

    2002-10-01

    The current study was designed to evaluate the effects of oral administration of the citrus coumarin, isopimpinellin, on skin tumor initiation by topically applied benzo[a]pyrene (B[a]P) and 7,12-dimethylbenz[a]anthracene (DMBA). To evaluate the effects of orally administered isopimpinellin on skin tumor initiation by B[a]P and DMBA, its effects on DNA adduct formation were first evaluated. Female SENCAR mice were pre-treated twice with corn oil, or isopimpinellin (70 mg/kg body wt per os) at 24 h and 2 h prior to topical treatment with B[a]P or DMBA. Another citrus coumarin, imperatorin, was also included in these experiments for comparison. Orally administered isopimpinellin and imperatorin significantly inhibited B[a]P-DNA adduct formation by 37 and 26%, respectively. Imperatorin also blocked DMBA-DNA adduct formation by 43%. In a second dose-response study, orally administered isopimpinellin (35, 70 and 150 mg/kg) blocked DMBA-DNA adduct formation by 23, 56 and 69%, respectively. For the tumor study, mice were pretreated orally with corn oil or isopimpinellin at 24 and 2 h prior to initiation with DMBA, and 2 weeks later promotion began with 12-O-tetradecanoylphorbol-13-acetate (TPA). Isopimpinellin significantly reduced the mean number of papillomas per mouse by 49, 73 and 78% compared to corn oil controls at 30, 70 and 150 mg/kg body wt, respectively. Orally administered isopimpinellin also significantly reduced the percentage of mice with papillomas at the highest dose tested (150 mg/kg). The effectiveness of isopimpinellin given topically over a broad dose range against DMBA tumor initiation was also evaluated for comparison. As part of this study, several parameters of systemic toxicity were evaluated following oral dosing with isopimpinellin and imperatorin. Mice were treated orally with corn oil, isopimpinellin or imperatorin (35, 70 and 150 mg/kg body wt per os) once daily for four consecutive days, killed at 24 h after the last dose, and livers, lungs

  15. Anisotropy in amorphous films of cross-shaped molecules with an accompanying effect on carrier mobility: Ellipsometric and sum-frequency vibrational spectroscopic studies

    NASA Astrophysics Data System (ADS)

    Oh-e, Masahito; Ogata, Hidenori; Fujita, Yoshimasa; Koden, Mitsuhiro

    2013-03-01

    Variable angle spectroscopic ellipsometry and sum-frequency vibrational spectroscopy have been used to study molecular orientations in thin films used in an organic light-emitting-diode. The films consist of sterically bulky and cross-shaped molecules that have small anisotropy in shape, 2-methyl-9,10-di(2-naphthyl)anthracene (MADN). As a result, anisotropic molecular orientation in the amorphous films has been observed with respect to the surface normal. The short axis of anthracene in MADN molecules, more or less, slightly tilts from the surface plane but preferentially close to the surface with a certain orientational distribution, while the long axis of anthracene is, on average, oriented close to the magic angle from the surface normal. This anisotropic molecular orientation gives rise to better carrier transportation properties than the isotropic orientation.

  16. Bifunctional Zn(II)Ln(III) dinuclear complexes combining field induced SMM behavior and luminescence: enhanced NIR lanthanide emission by 9-anthracene carboxylate bridging ligands.

    PubMed

    Palacios, María A; Titos-Padilla, Silvia; Ruiz, José; Herrera, Juan Manuel; Pope, Simon J A; Brechin, Euan K; Colacio, Enrique

    2014-02-03

    There were new dinuclear Zn(II)-Ln(III) complexes of general formulas [Zn(μ-L)(μ-OAc)Ln(NO3)2] (Ln(III) = Tb (1), Dy (2), Er (3), and Yb (4)), [Zn(μ-L)(μ-NO3)Er(NO3)2] (5), [Zn(H2O)(μ-L)Nd(NO3)3]·2CH3OH (6), [Zn(μ-L)(μ-9-An)Ln(NO3)2]·2CH3CN (Ln(III) = Tb (7), Dy (8), Er (9), Yb(10)), [Zn(μ-L)(μ-9-An)Yb(9-An)(NO3)3]·3CH3CN (11), [Zn(μ-L)(μ-9-An)Nd(9-An)(NO3)3]·2CH3CN·3H2O (12), and [Zn(μ-L)(μ-9-An)Nd(CH3OH)2(NO3)]ClO4·2CH3OH (13) prepared from the reaction of the compartmental ligand N,N',N″-trimethyl-N,N″-bis(2-hydroxy-3-methoxy-5-methylbenzyl)diethylenetriamine (H2L), with ZnX2·nH2O (X = NO3(-) or OAc(-)) salts, Ln(NO3)3·nH2O, and, in some instances, 9-anthracenecarboxylate anion (9-An). In all these complexes, the Zn(II) ions invariably occupy the internal N3O2 site whereas the Ln(III) ions show preference for the O4 external site, giving rise to a Zn(μ-diphenoxo)Ln bridging fragment. Depending on the Zn(II) salt and solvent used in the reaction, a third bridge can connect the Zn(II) and Ln(III) metal ions, giving rise to triple-bridged diphenoxoacetate in complexes 1-4, diphenoxonitrate in complex 5, and diphenoxo(9-anthracenecarboxylate) in complexes 8-13. Dy(III) and Er(III) complexes 2, 8 and 3, 5, respectively, exhibit field induced single molecule magnet (SMM) behavior, with Ueff values ranging from 11.7 (3) to 41(2) K. Additionally, the solid-state photophysical properties of these complexes are presented showing that ligand L(2-) is able to sensitize Tb(III)- and Dy(III)-based luminescence in the visible region through an energy transfer process (antenna effect). The efficiency of this process is much lower when NIR emitters such as Er(III), Nd(III), and Yb(III) are considered. When the luminophore 9-anthracene carboxylate is incorporated into these complexes, the NIR luminescence is enhanced which proves the efficiency of this bridging ligand to act as antenna group. Complexes 2, 3, 5, and 8 can be considered as dual materials

  17. Effects of dietary linseed, evening primrose or fish oils on fatty acid and prostaglandin E2 contents in the rat livers and 7,12-dimethylbenz[a]anthracene-induced tumours.

    PubMed

    Jelińska, Małgorzata; Tokarz, Andrzej; Oledzka, Regina; Czorniuk-Sliwa, Alicja

    2003-04-17

    We examined the influence of diets supplemented with fish and vegetable oils on fatty acid and prostaglandin E2 (PGE2) contents in livers of non-7,12-dimethylbenz[a]anthracene (DMBA)- and DMBA-treated rats, and in DMBA-induced tumours. Decreased concentrations of saturated fatty acids and increased unsaturated fatty acid levels were observed in liver phospholipids of rats fed these oils. There was a marked difference in the concentrations of fatty acids found in the tumours and those present in liver lipids. Oleic acid was the main unsaturated fatty acid found in the tumour tissue. Both liver and tumour PGE2 contents were clearly correlated to the diet. The PGE2 concentrations were decreased in livers and tumours of rats fed fish (FO) and linseed oils (LO).

  18. Vibrational spectroscopic (FT-IR, FT-Raman, SERS) and quantum chemical calculations of 3-(10,10-dimethyl-anthracen-9-ylidene)-N,N,N-trimethylpropanaminiium chloride (Melitracenium chloride).

    PubMed

    Mary, Y Shyma; Jojo, P J; Van Alsenoy, Christian; Kaur, Manpreet; Siddegowda, M S; Yathirajan, H S; Nogueira, Helena I S; Cruz, Sandra M A

    2014-01-01

    FT-IR, FT-Raman spectra of Melitracenium chloride were recorded and analyzed. SERS spectrum was recorded in silver colloid. The vibrational wavenumbers were computed using DFT quantum chemical calculations. The data obtained from wavenumber calculations are used to assign vibrational bands obtained in infrared and Raman spectra as well as in SERS of the studied molecule. Potential energy distribution was done using GAR2PED program. The geometrical parameters (SDD) of the title compound are in agreement with the XRD results. The presence anthracene ring modes in the SERS spectrum suggest a tilted orientation with respect to the metal surface. The methyl groups in the title molecule are also close to the metal surface. The first hyperpolarizability, NBO analysis and molecular electrostatic potential results are also reported.

  19. 1-[(Anthracen-9-yl)carbon­yl]-2,7-di­meth­oxy­naphthalene: a chain-like structure composed of face-to-face type dimeric mol­ecular aggregates

    PubMed Central

    Siqingaowa; Tsumuki, Takehiro; Ogata, Kazuki; Yonezawa, Noriyuki; Okamoto, Akiko

    2016-01-01

    The asymmetric unit of the title compound, C27H20O3, contains two independent mol­ecules (A and B). The anthracene ring system is connected to the 2,7-di­meth­oxy­naphthalene core in a twisted manner, with dihedral angles of 86.38 (5) and 79.36 (8)°, respectively, for conformers A and B. In the crystal, face-to-face type dimeric mol­ecular aggregates of each conformer are observed. The dimer of conformer A is formed by two pairs of C—H⋯π inter­actions, and that of conformer B by a pair of (sp 2)C—H⋯O hydrogen bonds. The dimers of conformer A are linked to each other via a π–π stacking inter­action between the anthracene rings to form a chain along the b axis and the chains are aligned along the c axis, forming a sheet structure. The dimers of conformer B are connected to each other via a couple of C—H⋯π inter­actions to form a chain along the b axis. The chains are aligned along the c axis through (sp 2)C—H⋯O=C hydrogen bonds, forming a sheet parallel to the bc plane. The sheets of conformers A and B are alternately stacked along the a axis via two kinds of inter­molecular (sp 2)C—H⋯O=C hydrogen bonds. PMID:27980839

  20. A high performance fluorescent white organic light-emitting device and its optimization for full-colour display

    NASA Astrophysics Data System (ADS)

    Li, Jiang; Duan, Yu; Zhao, Yi; Li, Xinhong; Li, Chuannan; Hou, Jingying; Liu, Shiyong

    2006-02-01

    A white organic light emitting diode (OLED) was fabricated in which blue emission host 9,10-di(2-naphthyl)anthracene (ADN) doped with an orange emission dye (rubrene) was used to generate bright, high efficiency white light. A large amount of work was done to study the emission mechanism of a rubrene-doped device. Finally, to get optimized EL spectra, we introduced a green light which is emitted from tris(8-hydroxy-quinoline) aluminium (Alq3), the electron transport material, into the emission of white light.

  1. Investigation of three-terminal organic-based devices with memory effect and negative differential resistance

    NASA Astrophysics Data System (ADS)

    Yu, Li-Zhen; Lee, Ching-Ting

    2009-09-01

    The current-voltage characteristics of the gate-controlled three-terminal organic-based devices with memory effect and negative differential resistances (NDR) were studied. Gold and 9,10-di(2-naphthyl)anthracene (ADN) were used as the metal electrode and active channel layer of the devices, respectively. By using various gate-source voltages, the memory and NDR characteristics of the devices can be modulated. The memory and NDR characteristics of the devices were attributed to the formation of trapping sites in the interface between Au electrode and ADN active layer caused by the defects, when Au metal deposited on the ADN active layer.

  2. Improved performances of organic light-emitting diodes with mixed layer and metal oxide as anode buffer

    NASA Astrophysics Data System (ADS)

    Xue, Qin; Liu, Shouyin; Zhang, Shiming; Chen, Ping; Zhao, Yi; Liu, Shiyong

    2013-01-01

    We fabricated organic light-emitting devices (OLEDs) employing 2-methyl-9,10-di(2-naphthyl)-anthracene (MADN) as hole-transport material (HTM) instead of commonly used N,N'-bis-(1-naphthyl)-N,N'-diphenyl,1,1'-biphenyl-4,4'-diamine (NPB). After inserting a 0.9 nm thick molybdenum oxide (MoOx) layer at the indium tin oxide (ITO)/MADN interface and a 5 nm thick mixed layer at the organic/organic heterojunction interface, the power conversion efficiency of the device can be increased by 4-fold.

  3. Efficient deep-blue organic light-emitting diodes using double-emitting layer.

    PubMed

    Seo, Ji Hoon; Seo, Bo Min; Lee, Seok Jae; Lee, Kum Hee; Yoon, Seung Soo; Kim, Young Kwan

    2012-04-01

    Efficient deep-blue organic light-emitting diodes were demonstrated using 1,4-tetranaphthalene doped in double-emitting layers (D-EMLs) consisting of 2-methyl-9,10-di(2-naphthyl)anthracene and 4'-(dinaphthalen-2-yl)-1,1'-binaphthyl as blue hosts. The device with D-EML exhibits good confinement of holes and electrons, as well as a broad recombination zone. The optimized device showed a peak current efficiency of 3.67 cd/A, a peak external quantum efficiency of 3.97%, and Commission Internationale de L'Eclairage coordinates of (0.16, 0.10).

  4. Anion-exchange and anthracene-encapsulation within copper(II) and manganese(II)-triazole metal-organic confined space in a single crystal-to-single crystal transformation fashion.

    PubMed

    Liu, Ju-Yan; Wang, Qian; Zhang, Li-Jun; Yuan, Bin; Xu, Yao-Yao; Zhang, Xin; Zhao, Cong-Ying; Wang, Dan; Yuan, Yue; Wang, Ying; Ding, Bin; Zhao, Xiao-Jun; Yue, Min Min

    2014-06-16

    A new multidentate ligand 1-(9-(1H-1,2,4-triazol-1-yl)anthracen-10-yl)-1H-1,2,4-triazole (tatrz) was designed and synthesized. Using tatrz as a building block, three novel coordination frameworks, namely, {[Cu(tatrz)2(NO3)2]·(CH3OH)·4H2O}n (1), {[Cu(tatrz)2(H2O)2](BF4)2}n (2), and [Mn(tatrz)2(SCN)2(CH3OH)]·2H2O (3) can be isolated. Anion-exchange experiment indicates that NO3(-) anions in the two-dimensional (2D) copper framework of 1 can be completely exchanged by ClO4(-) in an irreversible single crystal-to-single crystal (SC-SC) transformation fashion, as evidenced by the anion-exchange products of {[Cu(tatrz)2(H2O)2](ClO4)2·4CH3OH} (1a). Further, if 1a was employed as a precursor in N,N-dimethylformamide (DMF), an isomorphic solvate of {[Cu(tatrz)2(DMF)2](ClO4)2·2H2O}n (1b) can be generated during the reversible dynamic transformation process. When 1 was immersed in CH3OH, a distinct 2D layer {[Cu(tatrz)2(NO3)2]·4.4CH3OH·0.6H2O}n (1c) was isolated. Interestingly, the solvent-exchange conversion is also invertible between 1 and 1c, which exhibits spongelike dynamic behavior with retention of crystalline integrity. If the 2-fold interpenetrating three-dimensional (3D) framework 2 is selected, it can be transformed into another 2-fold interpenetrating 3D framework {[Cu(tatrz)2(H2O)2](ClO4)2·5.56H2O}n (2a) in a reversible SC-SC transformation fashion. However, when the light yellow crystals of mononuclear complex 3 were exposed to trichloromethane containing aromatic organic anthracene (atan), through our careful observation, the crystals of 3 were dissolved and reassembled into dark brown crystals of 2D crystalline coordination framework {[Mn(tatrz)2(SCN)2]·(atan)}n (3a). X-ray diffraction revealed that in 3a, atan acting as an organic template was encapsulated in the confined space of the 2D grid. Luminescent measurements illustrate that 3a is the first report of multidimensional polymers based on triazole derivatives as luminescent probes of Mg(2+).

  5. Cu(I) and Ag(I) complexes of 7,10-bis-N-heterocycle-diazafluoranthenes: programmed molecular grids?

    PubMed

    Rahanyan, Nelli; Duttwyler, Simon; Linden, Anthony; Baldridge, Kim K; Siegel, Jay S

    2014-07-28

    Reactions of 7,10-disubstituted diazafluoranthene derivatives with three different silver(I) salts AgX (X = [PF6](-), [SbF6](-), [CB11HCl11](-)) and [Cu(CH3CN)4]PF6 afforded complexes exhibiting five different motifs. The crystal structures of the free ligands and nine new complexes from this series of reactions are reported. The use of 2,5-di-tert-butyl-7,10-di(pyridin-2-yl)-8,9-diazafluoranthene as a ligand leads to the formation of the tetranuclear compounds [Ag4(C32H30N4)4][PF6]4·3C6H6·4MeCN, [Ag4(C32H30N4)4][SbF6]4·4C5H12 and [Cu4(C32H30N4)4][PF6]4·8C3H6O, which exhibit "propeller" and saddle-type geometry, respectively, as well as a dinuclear complex [Ag2(C32H30N4)2][CHB11Cl11]2·4C6H4Cl2·CH2Cl2. The reactions involving the less sterically hindered 2,5-di-tert-butyl-7,10-di-(pyrimidin-2-yl)-8,9-diazafluoranthene and 2,5-di-tert-butyl-7,10-di(thiazol-2-yl)-8,9-diazafluoranthene afforded crystals of the dinuclear complexes [Ag2(C30H28N6)2][PF6]2·0.5CH2Cl2·0.5C6H5Cl·0.5C6H12, [Ag2(C30H28N6)2][SbF6]2·C3H6O·0.5C6H14·0.5C6H6, the polymeric species [Ag2(C28H26N4S2)2]n·2n[PF6]n·nC3H6O and the tetranuclear compounds [Cu4(C26H25N4S2)4][PF6]4·2CHCl3·2C3H6O and [Cu4(C30H28N6)4][PF6]4·2.17H2O, which possess saddle and grid-like architectures, respectively. Conformational analysis of the free ligands showed that they exhibit N-C-C-N torsion angles ranging from syn clinal (58°) to fully anti-periplanar conformations; the syn clinal conformation dominates in the complexes. The relative energies of the possible structural conformations of the synthesized ligands, as well as of oxazole disubstituted diazafluoranthenes, were calculated using density functional theory at the B97D/Def2-TZVPP level of theory.

  6. Modulatory Effect of Taurine on 7,12-Dimethylbenz(a)Anthracene-Induced Alterations in Detoxification Enzyme System, Membrane Bound Enzymes, Glycoprotein Profile and Proliferative Cell Nuclear Antigen in Rat Breast Tissue.

    PubMed

    Vanitha, Manickam Kalappan; Baskaran, Kuppusamy; Periyasamy, Kuppusamy; Selvaraj, Sundaramoorthy; Ilakkia, Aruldoss; Saravanan, Dhiravidamani; Venkateswari, Ramachandran; Revathi Mani, Balasundaram; Anandakumar, Pandi; Sakthisekaran, Dhanapal

    2016-08-01

    The modulatory effect of taurine on 7,12-dimethylbenz(a)anthracene (DMBA)-induced breast cancer in rats was studied. DMBA (25 mg/kg body weight) was administered to induce breast cancer in rats. Protein carbonyl levels, activities of membrane bound enzymes (Na(+) /K(+) ATPase, Ca(2+) ATPase, and Mg(2+) ATPase), phase I drug metabolizing enzymes (cytochrome P450, cytochrome b5, NADPH cytochrome c reductase), phase II drug metabolizing enzymes (glutathione-S-transferase and UDP-glucuronyl transferase), glycoprotein levels, and proliferative cell nuclear antigen (PCNA) were studied. DMBA-induced breast tumor bearing rats showed abnormal alterations in the levels of protein carbonyls, activities of membrane bound enzymes, drug metabolizing enzymes, glycoprotein levels, and PCNA protein expression levels. Taurine treatment (100 mg/kg body weight) appreciably counteracted all the above changes induced by DMBA. Histological examination of breast tissue further supported our biochemical findings. The results of the present study clearly demonstrated the chemotherapeutic effect of taurine in DMBA-induced breast cancer.

  7. Anticancer activity of fungal taxol derived from Botryodiplodia theobromae Pat., an endophytic fungus, against 7, 12 dimethyl benz(a)anthracene (DMBA)-induced mammary gland carcinogenesis in Sprague Dawley rats.

    PubMed

    Pandi, M; Manikandan, R; Muthumary, J

    2010-01-01

    Breast cancer is the second most prevalent cancer worldwide and their incidence increases gradually. Taxol (paclitaxel), a potent anticancer drug, is naturally isolated from the bark of the Pacific yew. Taxol is widely used in the treatment of ovarian, lung and breast cancer. The increased demand for taxol, coupled with its limited availability from the protected Pacific yew, has had researchers scrambling for alternate sources. The purpose of the present study is to investigate chemopreventive effect of fungal taxol derived from a novel endophytic fungus Botryodiplodia theobromae Pat., isolated from a medicinal plant Morinda citrifolia Linn. The fungal taxol is found to be active against the 7, 12 dimethyl benz(a)anthracene (DMBA)-induced mammary gland carcinogenesis in Sprague dawley rats. The enzymic and non-enzymic antioxidants i.e. superoxide dismutase (SOD), catalase (CAT), glutatione peroxidase (GPx), glutatione-S-transferase (GST), reduced glutathione (GSH), vitamin C and vitamin E were evaluated in control and experimental groups. Lipid peroxides levels (LPO) were also tested. Histological analysis of breast tissue was analyzed by haematoxylin and eosin staining to assess the cytoprotective role of fungal taxol active against breast cancer. Immunohistochemical analyses were also performed to evaluate the effect of fungal taxol on the inflammatory marker such as Cyclooxygenase-2 (COX-2) in control and experimental groups. The results showed that the fungal taxol significantly suppresses the DMBA-induced breast cancer in Sprague dawley rats.

  8. Evaluation of Mammary Cancer in 7,12-Dimethylbenz(a)anthracene-Induced Wister Rats by Asymmetrical Temperature Distribution Analysis Using Thermography: A Comparison with Serum CEA Levels and Histopathology

    PubMed Central

    Angeline Kirubha, S. P.; Anburajan, M.; Venkataraman, B.; Akila, R.; Sharath, D.; Raj, Baldev

    2012-01-01

    Animal surface temperature profile captured using infrared camera is helpful for the assessment of physiological responses associated with the regulation of body temperature. Diagnosing breast cancer in early stage itself has a greater effect on the prognosis. In this work, asymmetrical temperature distribution analysis of chemical carcinogen 7,12-dimethyl benz(a)anthracene-induced in the lower right flank region of Wistar rats (n = 6) was carried out to test the potential of thermography in diagnosing mammary cancer and tumor growth over a period of nine weeks in comparison with histopathology results as standard. Temperature difference between the tumor induced lower right and left side of flank region was significant (with P value <0.001), whereas in the abdomen and shoulder there was no significant difference in temperature between right and left sides. Percentage of asymmetrical temperature difference in the tumor induced lower flank region was 0.5 to 2%, whereas in the other regions it was <0.5%. Green pixel distribution in RGB color histogram was asymmetrical in the tumor induced lower flank region. Temperature reduction was observed in the tumor induced region after the seventh day of carcinogen induction. Asymmetrical thermogram analysis is the best method of diagnosing mammary cancer and for studying tumor development. PMID:23093865

  9. Lack of chemopreventive effects of alpha-eleostearic acid on 7,12-dimethylbenz[a]anthracene (DMBA) and 1,2-dimethylhydrazine (DMH)-induced mammary and colon carcinogenesis in female Sprague-Dawley rats.

    PubMed

    Kitamura, Y; Yamagishi, M; Okazaki, K; Umemura, T; Imazawa, T; Nishikawa, A; Matsumoto, W; Hirose, M

    2006-02-01

    alpha-Eleostearic acid is one of the conjugated linolenic acids from tung oil, which is obtained from the seeds of Aleurites fordii. The effects of dietary alpha-eleostearic acid (18:3, n-5) on the post-initiation period of 7,12-dimethylbenz[a]anthracene (DMBA) and 1,2-dimethylhydrazine (DMH)-induced mammary and colon carcinogenesis were examined using female Sprague-Dawley (SD) rats. For initiation, rats were given subcutaneous injections of 40mg/kg body weight (5 times) and 20mg/kg body weight (3 times) of DMH during the age of 6-8 weeks and a single intragastric administration of 50mg/kg body weight of DMBA at 9 weeks. Then, the animals were treated with 0%, 0.01%, 0.1% or 1.0% alpha-eleostearic acid for 34 weeks. Control rats received the basal diet alone or 1.0% alpha-eleostearic acid without prior initiation treatment. All surviving animals were killed at week 37 of the experiment. There were no statistically significant alterations in any of the parameters for either mammary or colon tumors. These results thus indicate that alpha-eleostearic acid does not exert clear modification effects on DMBA and DMH-induced mammary and colon carcinogenesis, at least under the present experimental conditions.

  10. Combinatorial chemopreventive effect of butyric acid, nicotinamide and calcium glucarate against the 7,12-dimethylbenz(a)anthracene induced mouse skin tumorigenesis attained by enhancing the induction of intrinsic apoptotic events.

    PubMed

    Tiwari, Prakash; Sahay, Satya; Pandey, Manuraj; Qadri, Syed S Y H; Gupta, Krishna P

    2015-01-25

    We explored the basis of the combinatorial chemopreventive effect of butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) on mouse skin exposed to 7,12-dimethylbenz(a)anthracene (DMBA). We studied the effects of topical application of DMBA in the presence or absence of BA, NA and CAG on the regulators of apoptosis. DMBA treatment suppressed Bax, Bax/Bcl-2 ratio, release of cyt c, Apaf1, caspase-9, -3 mediated apoptosis. Downregulation of p21 and upregulation of Bcl-2, mut p53 were also observed in only DMBA treated mice. Simultaneous application of BA, NA and CAG induced a mitochondria-mediated apoptosis, characterized by a rise in the Bax, Bax/Bcl-2 ratio, release of cyt c, upregulation of Apaf1 with down-stream activation of caspase-9, -3. Furthermore treatment with BA, NA and CAG demonstrated an upregulation of p21 and downregulation of Bcl-2, mut p53. But this effect was enhanced in the presence of all the three compounds together in combination. Chemoprevention by a combination of BA, NA and CAG by inducing the apoptosis, the natural cell death, suggest the importance of the potential combinational strategies capable of preventing skin tumor development.

  11. Dose response study of conjugated fatty acid derived from safflower oil on mammary and colon carcinogenesis pretreated with 7,12-dimethylbenz[a]anthracene (DMBA) and 1,2-dimethylhydrazine (DMH) in female Sprague-Dawley rats.

    PubMed

    Cheng, Jing Lei; Futakuchi, Mitsuru; Ogawa, Kumiko; Iwata, Toshio; Kasai, Masaaki; Tokudome, Shinkan; Hirose, Masao; Shirai, Tomoyuki

    2003-07-10

    To clarify the chemopreventive effects of conjugated fatty acid derived from safflower oil (CFA-S), rich in conjugated linoleic acid (CLA), on mammary and colon carcinogenesis, 6 week old female Sprague-Dawley (SD) rats received diet containing 0.01, 0.05, 0.1, 1, or 2% CFA-S subsequent to five times subcutaneous injections of 1,2-dimethyl-hydrazine (DMH) at a dose of 40 mg/kg b.w. and a single 50 mg/kg b.w. intragastric application of 7,12-dimethylbenz[a]anthracene (DMBA) during the first 11 days. The experiment was terminated at week 36. Numbers of mammary tumors, colon aberrant crypt foci (ACF), and proliferative indices of mammary tumors, and colon epithelium were analyzed. The 1% dose was found to be optimal for suppression of carcinogenesis in both target organs, a good correlation being noted with between data for cell proliferation. These results suggest that a diet containing appropriate levels of CFA-S may be useful for prevention of mammary and colon cancer.

  12. Evaluation of mammary cancer in 7,12-dimethylbenz(a)anthracene-induced Wister rats by asymmetrical temperature distribution analysis using thermography: a comparison with serum CEA levels and histopathology.

    PubMed

    Angeline Kirubha, S P; Anburajan, M; Venkataraman, B; Akila, R; Sharath, D; Raj, Baldev

    2012-01-01

    Animal surface temperature profile captured using infrared camera is helpful for the assessment of physiological responses associated with the regulation of body temperature. Diagnosing breast cancer in early stage itself has a greater effect on the prognosis. In this work, asymmetrical temperature distribution analysis of chemical carcinogen 7,12-dimethyl benz(a)anthracene-induced in the lower right flank region of Wistar rats (n = 6) was carried out to test the potential of thermography in diagnosing mammary cancer and tumor growth over a period of nine weeks in comparison with histopathology results as standard. Temperature difference between the tumor induced lower right and left side of flank region was significant (with P value <0.001), whereas in the abdomen and shoulder there was no significant difference in temperature between right and left sides. Percentage of asymmetrical temperature difference in the tumor induced lower flank region was 0.5 to 2%, whereas in the other regions it was <0.5%. Green pixel distribution in RGB color histogram was asymmetrical in the tumor induced lower flank region. Temperature reduction was observed in the tumor induced region after the seventh day of carcinogen induction. Asymmetrical thermogram analysis is the best method of diagnosing mammary cancer and for studying tumor development.

  13. Putative metabolites derived from dietary combinations of calcium glucarate and N-(4-hydroxyphenyl) retinamide act synergistically to inhibit the induction of rat mammary tumors by 7,12-dimethylbenz(. alpha. )anthracene

    SciTech Connect

    Abou-Issa, H.M.; Duruibe, V.A.; Minton, J.P.; Larroya, S.; Dwivedi, D.; Webb, T.E. )

    1988-06-01

    Calcium glucarate and N-(4-hydroxyphenyl)-retinamide were calculated individually and in combination int he diet as preventative chemical agents, by using the induction of rat mammary tumors by 7,12-dimethylbenz({alpha})anthracene as the test system. When tested separately over 18 weeks, optimal doses of calcium glucarate or N-(4-hydroxyphenyl)retinamide administered daily inhibited tumor incidence by 50% or 57% and tumor multiplicity by 50% or 65%, respectively. Suboptimal doses of calcium glucarate and of N-(4-hydroxyphenyl)-retinamide inhibited tumor incidence by 15% and 5% but had no inhibitory effect on tumor multiplicity. In contrast, the combination of calcium glucarate and N-(4-hydroxyphenyl)retinamide inhibited tumor incidence and tumor multiplicity by 50%. Similar synergism was observed with the combination of calcium glucarate and N-(4-hydroxyphenyl)retinamide, the inhibition being 55-60%. HPLC analysis of the bile of female rats injected intraperitoneally with a single dose of the retinamide showed that the excretion of the retinamide and its glucuronide were markedly suppressed by pretreatment with an oral dose of calcium glucarate.

  14. Endogenous estrogen status, but not genistein supplementation, modulates 7,12-dimethylbenz[a]anthracene-induced mutation in the liver cII gene of transgenic big blue rats.

    PubMed

    Chen, Tao; Hutts, Robert C; Mei, Nan; Liu, Xiaoli; Bishop, Michelle E; Shelton, Sharon; Manjanatha, Mugimane G; Aidoo, Anane

    2005-06-01

    A growing number of studies suggest that isoflavones found in soybeans have estrogenic activity and may safely alleviate the symptoms of menopause. One of these isoflavones, genistein, is commonly used by postmenopausal women as an alternative to hormone replacement therapy. Although sex hormones have been implicated as an important risk factor for the development of hepatocellular carcinoma, there are limited data on the potential effects of the estrogens, including phytoestrogens, on chemical mutagenesis in liver. Because of the association between mutation induction and the carcinogenesis process, we investigated whether endogenous estrogen and supplemental genistein affect 7,12-dimethylbenz[a]anthracene (DMBA)-induced mutagenesis in rat liver. Intact and ovariectomized female Big Blue rats were treated with 80 mg DMBA/kg body weight. Some of the rats also received a supplement of 1,000 ppm genistein. Sixteen weeks after the carcinogen treatment, the rats were sacrificed, their livers were removed, and mutant frequencies (MFs) and types of mutations were determined in the liver cII gene. DMBA significantly increased the MFs in liver for both the intact and ovariectomized rats. While there was no significant difference in MF between the ovariectomized and intact control animals, the mutation induction by DMBA in the ovariectomized groups was significantly higher than that in the intact groups. Dietary genistein did not alter these responses. Molecular analysis of the mutants showed that DMBA induced chemical-specific types of mutations in the liver cII gene. These results suggest that endogenous ovarian hormones have an inhibitory effect on liver mutagenesis by DMBA, whereas dietary genistein does not modulate spontaneous or DMBA-induced mutagenesis in either intact or ovariectomized rats.

  15. Both (+/-)syn- and (+/-)anti-7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxides initiate tumors in mouse skin that possess -CAA- to -CTA- mutations at Codon 61 of c-H-ras.

    PubMed

    Tang, M S; Vulimiri, S V; Viaje, A; Chen, J X; Bilolikar, D S; Morris, R J; Harvey, R G; Slaga, T J; DiGiovanni, J

    2000-10-15

    We have determined the tumor-initiating activity of (+/-)syn- and (+/-)anti-7,12-dimethylbenz[a]anthracene-3,4-diol-1,2-epoxide (syn- and anti-DMBADE), the two metabolically formed bay-region diol epoxides of DMBA, and we have also analyzed mutations in the H-ras gene from tumors induced by these compounds. Using a two-stage, initiation-promotion protocol for tumorigenesis in mouse skin, we have found that both syn- and anti-DMBADE are active tumor initiators, and that the occurrence of papillomas is carcinogen dose dependent. All of the papillomas induced by syn-DMBADE (a total of 40 mice), 96% of those induced by anti-DMBADE (a total of 25 mice), and 94% of those induced by DMBA (a total of 16 mice) possessed a -CAA- to -CTA- mutation at codon 61 of H-ras. No mutations in codons 12 or 13 were detected in any tumor. Topical application of syn- and anti-DMBADE produced stable adducts in mouse epidermal DNA, most of which comigrated with stable DNA adducts formed after topical application of DMBA. Further analysis of the data showed that levels of the major syn- and anti-DMBADE-deoxyadenosine adducts formed after topical application of DMBA are sufficient to account for the tumor-initiating activity of this carcinogen on mouse skin. Previously, we showed that both the syn- and anti-DMBADE bind to the adenine (A182) at codon 61 of H-ras. Collectively, these results indicate that the adenine adducts induced by both bay-region diol epoxides of DMBA lead to the mutation at codon 61 of H-ras and, consequently, initiate tumorigenesis in mouse skin.

  16. On-line SPE chromatography with spectrophotometric diode array detection as a simple and advantageous choice for the selective trace analysis of benzo(a)anthracene degradation products from microalgae.

    PubMed

    García de Llasera, Martha Patricia; García-Cicourel, Alan Rodrigo

    2017-04-01

    In this work, a methodology based on on-line solid phase extraction (SPE) chromatography with spectrophotometric diode array detection was optimized and validated for the trace analysis of benzo(a)anthracene dihydrodiol degradation products from microalgae cultures 5,6-dihydrodiol, 8,9-dihydrodiol and 10,11-dihydrodiol. The two on-line methods for the constituents of the culture, an SPE/on-line SPE chromatographic method for liquid medium and a matrix solid phase dispersion (MSPD)/on-line SPE chromatographic method for biomass presented good linearity in the ranges of 0.5-47ngmL(-1) and 2-80ngmg(-1) of samples, respectively, with correlation coefficients r>0.99. The percent relative standard deviation (RSD%) values were ≤4.9%. For the liquid medium and biomass methods, the global recoveries were between 84% and 90% and between 67% and 78%, and the limit of detection LODs were ≤0.3ngmL(-1) and ≤0.8ngmg(-1) respectively. The methodology was applied to exposure bioassays, and for the first time the three metabolites were detected and quantified individually by their appearance in the biomass and when they were excreted into the liquid medium. The metabolite formed in the greatest amount was 10,11-dihydrodiol, and the maximum production of all metabolites was at 6h of exposure. This work contributes to the study of the degradation route of BaA, which has not been elucidated for microalgae until now.

  17. Preventive effects of butyric acid, nicotinamide, calcium glucarate alone or in combination during the 7, 12-dimethylbenz (a) anthracene induced mouse skin tumorigenesis via modulation of K-Ras-PI3K-AKTpathway and associated micro RNAs.

    PubMed

    Tiwari, Prakash; Sahay, Satya; Pandey, Manuraj; Qadri, Syed S Y H; Gupta, Krishna P

    2016-02-01

    Skin cancer is among the most common cancers worldwide and identifiable molecular changes for early and late stage of skin tumorigenesis can suggest the better targets for its control. In this study, we investigated the status of K-Ras-PI3K-AKTpathway followed by NF-κB, cyclin D1, MMP-9 and regulatory micro RNA during 7, 12-dimethylbenz[a]anthracene (DMBA) induced mouse skin tumorigenesis and its prevention by butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG), individually or in combination with respect to time. DMBA upregulated the K-Ras, PI3K, Akt, NF-κB, cyclin D1 and MMP-9, but downregulated the PTEN in a time dependent manner. DMBA also reduced the levels of micoRNA let-7a but induced the levels of miR-21 and miR-20a as a function of time. BA, NA and CAG were found to prevent DMBA induced changes, but they were most effective when used together in a combination. Reduced let-7a and miR-211 were correlated with the overexpression of K-Ras and MMP-9. Overexpression of miR-21 and miR-20a was correlated with the down regulation of PTEN and overexpression of Cyclin D1. Collectively, the enhanced chemopreventive potential of natural compound in combination via regulation of K-Ras-PI3K-AKTpathway along with regulatory micro RNAs provide a newer and effective mean for cancer management.

  18. Modulation of miR-203 and its regulators as a function of time during the development of 7, 12 dimethylbenz [a] anthracene induced mouse skin tumors in presence or absence of the antitumor agents

    SciTech Connect

    Tiwari, Prakash; Gupta, Krishna P.

    2014-07-15

    We investigated the chemopreventive effects of naturally occurring compounds like butyric acid (BA), nicotinamide (NA) and calcium glucarate (CAG) individually or in combination in 7, 12-dimethylbenz [a] anthracene (DMBA) treated mouse skin at 4 and 16 weeks, the time before and after the tumor development. DMBA application did not show any skin tumors at 4 weeks but well defined tumors appeared at 16 weeks. BA, NA or CAG prevented the tumor development significantly but the protection was highly enhanced when all these compounds were given together. In order to see the molecular changes progressing with tumors, we showed the downregulation of tumor suppressor miR-203 at 16 weeks and upregulation of histone deacetylases (HDAC), DNA methyltransferase, promoter methylation of miR-203 at 4 or 16 weeks. Regulators of micro RNA biogenesis such as DICER1 and Ago2 were also deregulated by DMBA. Proto-oncogene c-myc and BMI1 were upregulated and tumor suppressor gene p16 was downregulated by DMBA as a function of time. Effects of BA, NA or CAG were more pronounced after 16 weeks as compared to 4 weeks in preventing the tumor development and altered gene expression. Concomitant administration of BA, NA and CAG tried to prevent these alterations more effectively than that of individual compound possibly by regulating miR-203 status through epigenetic or biogenetic modulations before and after the tumor development. Study provides a rationale for chemoprevention by combination of different compounds targeting miR-203. - Highlights: • DMBA modulates miR-203 and its regulator before and after the onset of tumors. • Suppression of miR-203 and p16 could be the result of gene promoter methylation. • BA, NA or CAG prevents the effects of DMBA. • Combination of BA, NA or CAG is more effective in preventing the DMBA modulations.

  19. Diminution of Hepatic Response to 7, 12-dimethylbenz(α)anthracene by Ethyl Acetate Fraction of Acacia catechu Willd. through Modulation of Xenobiotic and Anti-Oxidative Enzymes in Rats

    PubMed Central

    Kumar, Rakesh; Kaur, Rajbir; Singh, Amrit Pal; Arora, Saroj

    2014-01-01

    Background Liver is the primary metabolizing site of body and is prone to damage by exogenous as well as endogenous intoxicants. Polycyclic aromatic hydrocarbons such as 7, 12- dimethylbenz(α)anthracene (DMBA) is an exogenous hepatotoxin, which is well known for modulating phase I, II and anti-oxidative enzymes of liver. Plants contain plethora of polyphenolic compounds which can reverse the damaging effect of various xenobiotics. The present study investigated protective role of the ethyl acetate fraction of Acacia catechu Willd. (EAF) against DMBA induced alteration in hepatic metabolizing and anti-oxidative enzymes in rats. Methodology and Principal Findings The rats were subjected to hepatic damage by treating with DMBA for 7 weeks on alternative days and treatment schedule was terminated at the end of 14 weeks. The rats were euthanized at the end of protocol and livers were homogenized. The liver homogenates were used to analyse phase I (NADPH-cytochrome P450 reducatse, NADH-cytochrome b5 reductase, cytochrome P420, cytochrome b5), phase II (glutathione-S-transferase, DT diaphorase and γ-Glutamyl transpeptidase) and antioxidative enzymes (catalase, superoxide dismutase, ascorbate peroxidase, glutathione reductase, guiacol peroxidase and lactate dehydrogenase). Furthermore, other oxidative stress parameters (thiobarbituric acid reactive substances, lipid hydroperoxides and conjugated dienes and reduced glutathione) and liver marker enzymes (serum glutamic oxaloacetic transaminase, serum glutamic pyruvic transaminase and alkaline phosphatase) were also studied. The DMBA induced significant changes in activity of hepatic enzymes that was reversed by treatment with three dose levels of EAF. Conclusion It is concluded that EAF affords hepato-protection against DMBA in rats through modulation of phase I, II and anti-oxidative enzymes. PMID:24587216

  20. Tangeretin, a citrus pentamethoxyflavone, exerts cytostatic effect via p53/p21 up-regulation and suppresses metastasis in 7,12-dimethylbenz(α)anthracene-induced rat mammary carcinoma.

    PubMed

    Arivazhagan, Lakshmi; Sorimuthu Pillai, Subramanian

    2014-11-01

    Breast cancer is the most commonly diagnosed cancer among women worldwide, which is characterized by unregulated cell growth and metastasis. Many bioactive compounds of plant origin such as tangeretin have been shown to possess potent antioxidant and anticancerous properties. In the present study we have investigated the chemotherapeutic effect of tangeretin against 7,12-dimethylbenz(α)anthracene (DMBA)-induced rat mammary carcinogenesis and studied its underlying mechanism of action. Breast cancer was induced by "air pouch technique" with a single dose of 25mg/kg of DMBA. Tangeretin (50 mg/kg) was administered orally for four weeks. Remarkably, tangeretin treatment controlled the growth of cancer cells which was clearly evidenced by morphological and histological analysis. Also, serum levels of estradiol, progesterone and prolactin; lipid bound sialic acid and total sialic acid and the tissue levels of nitric oxide and protein carbonyls of cancer induced animals were decreased upon tangeretin treatment. Staining of breast tissues for nucleolar organizer regions, mast cells, glycoproteins, lipids and collagen showed that tangeretin treatment to breast cancer induced rats significantly reduced tumorigenesis. Oral tangeretin treatment also effectively reduced the tumor cell proliferation markers such as PCNA, COX-2 and Ki-67. Further, tangeretin treatment arrested the cancer cell division at the G1/S phase via p53/p21 up-regulation and inhibited metastasis by suppressing matrix metalloproteinase (MMP)-2, MMP-9 and vascular endothelial growth factor. Taken together, the data provides new evidence on the mechanism of action of tangeretin in breast cancer and hence extends the hypothesis supporting its potential use in chemotherapy.

  1. PTEN/PIK3CA genes are frequently mutated in spontaneous and medroxyprogesterone acetate-accelerated 7,12-dimethylbenz(a)anthracene-induced mammary tumours of tree shrews.

    PubMed

    Xia, Hou-Jun; He, Bao-Li; Wang, Chun-Yan; Zhang, Hai-Lin; Ge, Guang-Zhe; Zhang, Yuan-Xu; Lv, Long-Bao; Jiao, Jian-Lin; Chen, Ceshi

    2014-12-01

    Tree shrew has increasingly become an attractive experimental animal model for human diseases, particularly for breast cancer due to spontaneous breast tumours and their close relationship to primates and by extension to humans. However, neither normal mammary glands nor breast tumours have been well characterised in the Chinese tree shrew (Tupaia belangeri chinensis). In this study, normal mammary glands from four different developmental stages and 18 spontaneous breast tumours were analysed. Haematoxylin and eosin (H&E) staining and immunohistochemistry (IHC) showed that normal mammary gland morphology and structures of tree shrews were quite similar to those found in humans. Spontaneous breast tumours of tree shrews were identified as being intraductal papilloma, papillary carcinoma, and invasive ductal carcinoma with or without lung metastasis. To further analyse breast cancer tumours among tree shrews, 40 3-4 month-old female tree shrews were orally administrated 20 mg 7,12-dimethylbenz(a)anthracene (DMBA) or peanut oil thrice, and then, 15 of these DMBA administrated tree shrews were implanted with medroxyprogesterone acetate (MPA) pellets. DMBA was shown to induce breast tumours (12%) while the addition of MPA increased the tumour incidence (50%). Of these, three induced breast tumours were intraductal papillary carcinomas and one was invasive ductal carcinoma (IDC). The PTEN/PIK3CA (phosphatase and tensin homologue/phosphatidylinositol-4,5-bisphosphate 3-kinase catalytic subunit alpha), but not TP53 and GATA3, genes are frequently mutated in breast tumours, and the PTEN/PIK3CA gene mutation status correlated with the expression of pAKT in tree shrew breast tumours. These results suggest that tree shrews may be a promising animal model for a subset of human breast cancers with PTEN/PIK3CA gene mutations.

  2. Enrichment of maternal diet with conjugated linoleic acids influences desaturases activity and fatty acids profile in livers and hepatic microsomes of the offspring with 7,12-dimethylbenz[a]anthracene-induced mammary tumors.

    PubMed

    Białek, Agnieszka; Stawarska, Agnieszka; Tokarz, Andrzej; Czuba, Katarzyna; Konarska, Anna; Mazurkiewicz, Magdalena

    2014-01-01

    The aim of this study was to assess the influence of diet supplementation of pregnant and breast-feeding female Sprague-Dawley rats with conjugated linoleic acids (CLA) on the Δ6- and Δ5-desaturase activity in hepatic microsomes as well as on fatty acids profile and lipids peroxidation in liver and hepatic microsomes of the progeny with chemically induced mammary tumors. Rats were divided into two groups with different diet supplementation (vegetable oil (which did not contain CLA) or CLA). Their female offspring was divided within these groups into two subgroups: (1)--fed the same diet as mothers (K1 - oil, 01 - CLA), and (2)--fed the standard fodder (K2, O2). At 50th day of life, the progeny obtained carcinogenic agent (7,12-dimethylbenz[a]anthracene). Higher supply of CLA in diet of mothers resulted in lower susceptibility to chemically induced mammary tumors in their offspring (p = 0.0322). It also influenced the fatty acids profile in livers and in hepatic microsomes, especially polyunsaturated n3 and n6 fatty acids. CLA inhibited the activity of the desaturases, which confirmed that CLA can reduce the level of arachidonic acid directly, reducing linoleic acid content in membranes, or indirectly, through the regulation of its metabolism. We were unable to confirm or deny the antioxidative properties of CLA. Our results indicate that the higher supply of CLA in mothers' diet during pregnancy and breastfeeding causes their incorporation into tissues of children, changes the efficiency of fatty acids metabolism and exerts health-promoting effect in their adult life reducing the breast cancer risk.

  3. Regression of progestin-accelerated 7,12-dimethylbenz[a]anthracene-induced mammary tumors in Sprague-Dawley rats by p53 reactivation and induction of massive apoptosis: a pilot study.

    PubMed

    Benakanakere, Indira; Besch-Williford, Cynthia; Ellersieck, Mark R; Hyder, Salman M

    2009-03-01

    p53 Reactivation and induction of massive apoptosis (PRIMA-1) is a small-molecule compound that reactivates mutant p53, restoring its normal tumor suppressor function. PRIMA-1 effectively suppresses the growth of homogeneous p53-deficient tumor xenografts in immunosuppressed mice; however, the ability of PRIMA-1 to suppress the growth of mammary tumors in rodents and other species is not well characterized. Here, we examined the ability of PRIMA-1 to suppress the growth of 7,12-dimethylbenz[a]anthracene (DMBA)-induced and progestin-accelerated DMBA-induced mammary tumors in Sprague-Dawley rats. Mammary tumors were induced in female rats with DMBA or DMBA plus progestin treatment. After tumors had reached 5-25 mm(2) in size, PRIMA-1 was administered twice a day for 3 days via tail vein injection (20 or 50 mg/kg). Tumor size was monitored every day following PRIMA-1 for at least 15 days prior to killing. PRIMA-1 caused regression of approximately 40% of progestin-accelerated DMBA-induced mammary tumors, but did not induce regression of native non-progestin-accelerated DMBA-induced tumors. Importantly, PRIMA-1 also suppressed the emergence of any new progestin-accelerated tumors in this model. Immunological studies with an antibody that selectively reacts with mutant p53 suggested that none of the native DMBA-induced tumors expressed mutant p53. By contrast, six out of eight progestin-accelerated DMBA-induced tumors stained for mutant p53 protein. In PRIMA-1-treated tumor-bearing rats, tumor regression correlated with conversion of mutant to wild-type p53 conformation, reduced expression of vascular endothelial growth factor and estrogen receptor, lack of blood vessel perfusion, increased expression of p21, and massively increased expression of anti-angiogenic protein, secreted protein acidic and rich in cysteine. These pre-clinical results suggest that PRIMA-1, as a single agent or in combination with other anti-cancer compounds, has potential as a novel

  4. Metformin inhibits 7,12-dimethylbenz[a]anthracene-induced breast carcinogenesis and adduct formation in human breast cells by inhibiting the cytochrome P4501A1/aryl hydrocarbon receptor signaling pathway

    SciTech Connect

    Maayah, Zaid H.; Ghebeh, Hazem; Alhaider, Abdulqader A.; El-Kadi, Ayman O.S.; Soshilov, Anatoly A.; Denison, Michael S.; Ansari, Mushtaq Ahmad; Korashy, Hesham M.

    2015-04-15

    Recent studies have established that metformin (MET), an oral anti-diabetic drug, possesses antioxidant activity and is effective against different types of cancer in several carcinogen-induced animal models and cell lines. However, whether MET can protect against breast cancer has not been reported before. Therefore, the overall objectives of the present study are to elucidate the potential chemopreventive effect of MET in non-cancerous human breast MCF10A cells and explore the underlying mechanism involved, specifically the role of cytochrome P4501A1 (CYP1A1)/aryl hydrocarbon receptor (AhR) pathway. Transformation of the MCF10A cells into initiated breast cancer cells with DNA adduct formation was conducted using 7,12-dimethylbenz[a]anthracene (DMBA), an AhR ligand. The chemopreventive effect of MET against DMBA-induced breast carcinogenesis was evidenced by the capability of MET to restore the induction of the mRNA levels of basic excision repair genes, 8-oxoguanine DNA glycosylase (OGG1) and apurinic/apyrimidinic endonuclease1 (APE1), and the level of 8-hydroxy-2-deoxyguanosine (8-OHdG). Interestingly, the inhibition of DMBA-induced DNA adduct formation was associated with proportional decrease in CYP1A1 and in NAD(P)H:quinone oxidoreductase 1 (NQO1) gene expression. Mechanistically, the involvements of AhR and nuclear factor erythroid 2-related factor-2 (Nrf2) in the MET-mediated inhibition of DMBA-induced CYP1A1 and NQO1 gene expression were evidenced by the ability of MET to inhibit DMBA-induced xenobiotic responsive element and antioxidant responsive element luciferase reporter gene expression which suggests an AhR- and Nrf2-dependent transcriptional control. However, the inability of MET to bind to AhR suggests that MET is not an AhR ligand. In conclusion, the present work shows a strong evidence that MET inhibits the DMBA-mediated carcinogenicity and adduct formation by inhibiting the expression of CYP1A1 through an AhR ligand-independent mechanism

  5. Voltammetric studies on the potent carcinogen, 7,12-dimethylbenz[a]anthracene: Adsorptive stripping voltammetric determination in bulk aqueous forms and human urine samples and detection of DNA interaction on pencil graphite electrode.

    PubMed

    Yardim, Y; Keskin, E; Levent, A; Ozsöz, M; Sentürk, Z

    2010-01-15

    7,12-Dimethylbenz[a]anthracene (DMBA), is a widely studied polycyclic aromatic hydrocarbon that has long been recognized as a very potent carcinogen. Initially, the electrochemical oxidation of DMBA at the glassy carbon and pencil graphite electrodes in non-aqueous media (dimethylsulphoxide with lithium perchlorate) was studied by cyclic voltammetry. DMBA was irreversibly oxidized in two steps at high positive potentials, resulting in the ill-resolved formation of a couple with a reduction and re-oxidation wave at much lower potentials. Special attention was given to the use of adsorptive stripping voltammetry together with a medium exchange procedure on disposable pencil graphite electrode in aqueous solutions over the pH range of 3.0-9.0. The response was characterized with respect to pH of the supporting electrolyte, pre-concentration time and accumulation potential. Using square-wave stripping mode, the compound yielded a well-defined voltammetric response in acetate buffer, pH 4.8 at +1.15V (vs. Ag/AgCl) (a pre-concentration step being carried out at a fixed potential of +0.60V for 360s). The process could be used to determine DMBA concentrations in the range 2-10nM, with an extremely low detection limit of 0.194nM (49.7ngL(-1)). The applicability to assay of spiked human urine samples was also illustrated. Finally, the interaction of DMBA with fish sperm double-stranded DNA based on decreasing of the oxidation signal of adenine base was studied electrochemically by using differential pulse voltammetry with a pencil graphite electrode at the surface and also in solution. The favorable signal-to-noise characteristics of biosensor resulted in low detection limit (ca. 46nM) following a 300-s interaction. These results displayed that the electrochemical DNA-based biosensor could be used for the sensitive, rapid, simple and cost effective detection of DMBA-DNA interaction.

  6. Influence of Na+ on DNA reactions with aromatic epoxides and diol epoxides: evidence that DNA catalyzes the formation of benzo[a]pyrene and benz[a]anthracene adducts at intercalation sites.

    PubMed

    Fernando, H; Huang, C R; Milliman, A; Shu, L; LeBreton, P R

    1996-12-01

    Reactions of the benzo[a]pyrene (BP) and benz[a]anthracene (BA) metabolites, (+/-)-trans-7 8-dihydroxy-anti-9, 10-epoxy-7, 8, 9, 10-tetrahydro-BP (BPDE), (+/-)-trans-3, 4-dihydroxy-anti- 1,2-epoxy-1,2,3,4-tetrahydro-BA (BADE), (+/-)-BP-4,5-oxide (BPO), and (+/-)-BA-5, 6-oxide (BAO), were examined under pseudo-first-order conditions at varying Na+ (2.0-100 Mm) and native calf thymus DNA (ctDNA) concentrations. In 0.2 mM ctDNA and 2.0 mM Na+, at a pH of 7.3 most BPDE, BADE, BPO, and BAO (87-95%) undergo DNA catalyzed hydrolysis or rearrangement. For BPDE and BPO, overall, pseudo-first-order rate constants, k, in 2.0 mM Na+ and 0.2 mM ctDNA are 21-72 times larger than values obtained without DNA. For BADE and BAO, the rate constants are less strongly influenced by DNA; k values in 0.2 mM ctDNA are only 9-12 times larger than values obtained without DNA. Kinetic data for BPDE, BPO, BADE, and BAO and DNA intercalation association constants (KA) for BP and BA diols which are model compounds indicate that KA values for BPDE and BPO in 2.0 mM Na+ are 6.6-59 times larger than those of BADE and BAO. The greater DNA enhancement of rate constants for BPDE and BPO, versus BADE and BAO, correlates with the larger KA values of the BP metabolites. DNA adducts, which account for less than 10% of the yields, also form. For BPDE in 0.20 mM ctDNA, k decreases 5.1 times as the Na+ concentration increases from 2.0 to 100 mM. Nevertheless, the DNA adduct level remains constant over the range of Na+ concentrations examined. These results provide evidence that, for BPDE in 0.20 mM DNA and 2.0 mM Na+, ctDNA adduct formation follows a mechanism which is similar to that for DNA catalyzed hydrolysis. The pseudo-first-order rate constant for adduct formation, kAd, given approximately by kAd approximately equal to (kcat,AdKA[DNA])/(1 + KA[DNA]), where kcat,Ad is a catalytic rate constant. for BADE, BPO, and BAO, the influence of varying DNA and Na+ concentrations on k values is similar to that

  7. NTP Toxicology and Carcinogenesis Studies of o-Phenylphenol (CAS No. 90-43-7) Alone and with 7,12-Dimethylbenz(a)anthracene (CAS No. 57-97-6) in Swiss CD-1 Mice (Dermal Studies).

    PubMed

    1986-03-01

    o-Phenylphenol is used primarily as a germicide and fungicide for citrus fruits and vegetables and was selected for carcinogenesis studies because of the potential for human exposure. Four-week studies were conducted in which groups of 10 male and 10 female Swiss Webster mice were given dermal applications to the dorsal interscapular region of 0, 6, 11, 21, 36, or 56 mg of o-phenylphenol in 0.1 ml of acetone. Doses were administered 3 days per week for 4 weeks, and animals were monitored for clinical changes. Reductions in body weights of acetone vehicle control were observed, but no compound-related changes in weight or survival occurred in male or female mice administered o-phenylphenol. o-Phenylphenol caused dose-related ulcerative lesions at the site of application. The severity of these lesions was judged not to be life threatening. Carcinogenesis studies were conducted to determine whether o-phenylphenol was a complete carcinogen for skin or a promoter in a two-stage initiation/promotion skin paint model. Groups of 50 Swiss CD-1 mice of each sex were used for up to 102 weeks. Five dose groups were used: an acetone vehicle control group; a positive control group initiated with 7,12-dimethylbenz(a)- anthracene (DMBA) and promoted with 12-O-tetradecanoylphorbol-13-acetate (TPA); an initiator control group that received DMBA plus acetone; a group that received repeated applications of o-phenylphenol. The following doses were applied dermally to a clipped area on the dorsal interscapular region 3 days per week: o-phenylphenol - 55.5 mg/0.1 ml acetone; or TPA - 0.005 mg/0.1 ml acetone. DMBA was administered as a single dose at a concentration of 0.05 mg/0.1 ml acetone to the dorsal interscapular region. In the 2-year studies, mean body weights of the o-phenylphenol, DMBA/o-phenylphenol, and DMBA/TPA groups were not markedly different from those of mice that received DMBA/acetone. Similarly, there were no significant group differences in survival except for a

  8. Unexpected chemistry from the reaction of naphthyl and acetylene at combustion-like temperatures.

    PubMed

    Parker, Dorian S N; Kaiser, Ralf I; Bandyopadhyay, Biswajit; Kostko, Oleg; Troy, Tyler P; Ahmed, Musahid

    2015-04-27

    The hydrogen abstraction/acetylene addition (HACA) mechanism has long been viewed as a key route to aromatic ring growth of polycyclic aromatic hydrocarbons (PAHs) in combustion systems. However, doubt has been drawn on the ubiquity of the mechanism by recent electronic structure calculations which predict that the HACA mechanism starting from the naphthyl radical preferentially forms acenaphthylene, thereby blocking cyclization to a third six-membered ring. Here, by probing the products formed in the reaction of 1- and 2-naphthyl radicals in excess acetylene under combustion-like conditions with the help of photoionization mass spectrometry, we provide experimental evidence that this reaction produces 1- and 2-ethynylnaphthalenes (C12 H8 ), acenaphthylene (C12 H8 ) and diethynylnaphthalenes (C14 H8 ). Importantly, neither phenanthrene nor anthracene (C14 H10 ) was found, which indicates that the HACA mechanism does not lead to cyclization of the third aromatic ring as expected but rather undergoes ethynyl substitution reactions instead.

  9. Characteristics of blue organic light emitting diodes with different thick emitting layers

    NASA Astrophysics Data System (ADS)

    Li, Chong; Tsuboi, Taiju; Huang, Wei

    2014-08-01

    We fabricated blue organic light emitting diodes (called blue OLEDs) with emitting layer (EML) of diphenylanthracene derivative 9,10-di(2-naphthyl)anthracene (ADN) doped with blue-emitting DSA-ph (1-4-di-[4-(N,N-di-phenyl)amino]styryl-benzene) to investigate how the thickness of EML and hole injection layer (HIL) influences the electroluminescence characteristics. The driving voltage was observed to increase with increasing EML thickness from 15 nm to 70 nm. The maximum external quantum efficiency of 6.2% and the maximum current efficiency of 14 cd/A were obtained from the OLED with 35 nm thick EML and 75 nm thick HIL. High luminance of 120,000 cd/m2 was obtained at 7.5 V from OLED with 15 nm thick EML.

  10. Memory bistable mechanisms of organic memory devices

    NASA Astrophysics Data System (ADS)

    Lee, Ching-Ting; Yu, Li-Zhen; Chen, Hung-Chun

    2010-07-01

    To investigate the memory bistable mechanisms of organic memory devices, the structure of [top Au anode/9,10-di(2-naphthyl)anthracene (ADN) active layer/bottom Au cathode] was deposited using a thermal deposition system. The Au atoms migrated into the ADN active layer was observed from the secondary ion mass spectrometry. The density of 9.6×1016 cm-3 and energy level of 0.553 eV of the induced trapping centers caused by the migrated Au atoms in the ADN active layer were calculated. The induced trapping centers did not influence the carrier injection barrier height between Au and ADN active layer. Therefore, the memory bistable behaviors of the organic memory devices were attributed to the induced trapping centers. The energy diagram was established to verify the mechanisms.

  11. Optical and morphological characteristics of organic thin films for optoelectronic devices

    NASA Astrophysics Data System (ADS)

    Zhong, Zhiyou; Sun, Fenglou

    2007-12-01

    Organic semiconductor thin films of tri-(8-hydroxyquinoline)-aluminum (Alq), 9,10-di-(2-naphthyl)-anthracene (ADN), and N,N'bis(naphthalen-1-yl)-N,N'bis(phenyl)-benzidine (NPB) for optoelectronic devices were deposited onto glass substrates by vacuum sublimation technique. The surface morphology and roughness of the thin film were characterized by means of atomic force microscopy (AFM). Experimental results indicate that all thin films present similar granular topography but different surface roughness. In addition, the optical transmittance spectra of thin films were measured by a double beam spectrophotometer and their corresponding optical properties were investigated. The complex refractive index and the optical band gap of thin films were obtained, respectively. Meanwhile, the dispersion behavior of the refractive index was studied in terms of Wemple-DiDomenico single oscillator model, and the oscillator parameters were achieved.

  12. White organic light-emitting diodes based on incomplete energy transfer from perylene to rubrene

    NASA Astrophysics Data System (ADS)

    Ding, Bangdong; Zhu, Wenqing; Jiang, Xueyin; Zhang, Zhilin

    2008-11-01

    This paper presents organic light-emitting diodes which generate white emission based on both perylene and rubrene doped in 9,10-di(2-naphthyl)anthracene (ADN). In this doping system, the blue dopant perylene not only emitted but also assisted the energy transfer from ADN to rubrene, which contributes to a lower doping concentration of rubrene. The optimal configuration of the device is ITO/TPD(50 nm)/ADN:0.5 wt% perylene:0.006 wt% rubrene(40 nm)/Bphen(25 nm)/LiF(1 nm)/Al. The maximum luminance of 11 665 cd/m 2 at 14 V according to a luminance efficiency of 2.9 cd/A was obtained. A CIE color coordinate of (0.30, 0.37) at 4 mA/cm 2 was also achieved.

  13. Localized operator partitioning method for electronic excitation energies in the time-dependent density functional formalism.

    PubMed

    Nagesh, Jayashree; Frisch, Michael J; Brumer, Paul; Izmaylov, Artur F

    2016-12-28

    We extend the localized operator partitioning method (LOPM) [J. Nagesh, A. F. Izmaylov, and P. Brumer, J. Chem. Phys. 142, 084114 (2015)] to the time-dependent density functional theory framework to partition molecular electronic energies of excited states in a rigorous manner. A molecular fragment is defined as a collection of atoms using Becke's atomic partitioning. A numerically efficient scheme for evaluating the fragment excitation energy is derived employing a resolution of the identity to preserve standard one- and two-electron integrals in the final expressions. The utility of this partitioning approach is demonstrated by examining several excited states of two bichromophoric compounds: 9-((1- naphthyl)- methyl)- anthracene and 4-((2- naphthyl)- methyl)- benzaldehyde. The LOPM is found to provide nontrivial insights into the nature of electronic energy localization that is not accessible using a simple density difference analysis.

  14. Identification and determination of carboxylic acids in food samples using 2-(2-(anthracen-10-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)ethyl 4-methylbenzenesulfonate (APIETS) as labeling reagent by HPLC with FLD and APCI/MS.

    PubMed

    Sun, Zhiwei; You, Jinmao; Song, Cuihua; Xia, Lian

    2011-08-15

    A new labeling reagent for carboxylic acids, 2-(2-(anthracen-10-yl)-1H-phenanthro[9,10-d]imidazol-1-yl)ethyl 4-methylbenzenesulfonate (APIETS) has been designed and synthesized. It was used to label eight fatty acids (lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid, oleic acid, linoleic acid and linolenic acid) and four hydroxy pentacyclic triterpene acids (oleanolic acid, ursolic acid, betulinic acid and maslinic acid), successfully. APIETS could easily and quickly label carboxylic acids in the presence of K(2)CO(3) catalyst at 85°C for 35 min in N,N-dimethylformamide solvent. The carboxylic acids derivatives were separated on a C(8) reversed-phase column with gradient elution and fluorescence detection at λ(ex)/λ(em)=315/435 nm. Identification of these derivatives was carried out by online mass spectrometry with atmospheric pressure chemical ionization in positive ion mode. The detection limits obtained were 13.37-30.26fmol (signal-to-noise ratio of 3). The proposed method has been applied to the quantification of carboxylic acids in sultana raisin (Thompson seedless), hawthorn flake (Crataegus pinnatifida Bge.), Lycium barbarum seed oil and Microula sikkimensis seed oil with recoveries over 95.3%. It has been demonstrated that APIETS is a prominent labeling reagent for determining carboxylic acids with high performance liquid chromatography.

  15. Highly Twisted Triarylamines for Photoinduced Intramoleculer ChargeTransfer

    SciTech Connect

    Chudomel, J. M.; Yang, B. Q.; Barnes, M. D.; Achermann, M.; Mague, J. T.; Lahti, P. M.

    2011-08-04

    9-(N,N-Dianisylamino)anthracene (9DAAA), 9-(N,N-dianisylamino)dinaphth([1,2-a:2'-1'-j]-anthracene (9DAAH), and 9,10-bis(N,N-dianisylamino)anthracene (910BAA) were synthesized as highly twisted triarylamines with potential for photoexcited internal charge transfer. Crystallography of 9DAAA shows its dianisylamino group to be twisted nearly perpendicular to its anthracene unit, similar to a report for 910BAA. The solution fluorescence spectra show strong bathochromic shifts for each of the three molecular systems with strongly decreased quantum efficiency in higher polarity solvents. Solution-phase (ensemble) time-resolved photoluminescence measurements show up to 4-fold decreases in fluorescence lifetime in acetonitrile compared to hexane. The combined results are consistent with photoinduced, transient intramolecular charge-transfer from the bis-anisylamine unit to the polycyclic aromatic unit. Computational modeling is in accord with intramolecular transfer of electron density from the bis-anisylamino unit to the anthracene, based on in comparisons of HOMO and LUMO.

  16. Single-displacement controlled spontaneous electrolysis towards CuTCNQ microribbon electrodes in organic single-crystal transistors.

    PubMed

    He, Liangfu; Ji, Zhuoyu; Zhen, Yonggang; Liu, Jie; Yang, Fangxu; Zhao, Qiang; Dong, Huanli; Hu, Wenping

    2015-10-28

    Using single-displacement controlled spontaneous electrolysis solution-prepared CuTCNQ microribbons as the source/drain electrodes, we have fabricated 9,10-bis(2-phenylethynyl)anthracene (BEPA) based organic single crystal top-contact field-effect transistors. The interfacial energetic match between organic semiconductors and CuTCNQ electrodes with the low contact resistance accounts for the compelling improvement in electrical characteristics relative to the copper electrode, even comparable to gold counterparts. Furthermore, we have estimated the contact resistance of single-crystal transistors by the transfer line method (TLM).

  17. Voltage-Dependent Luminescence Properties of Molecularly Doped Polymer System

    NASA Astrophysics Data System (ADS)

    Mingliang, Wang; Junxiang, Zhang; Juzheng, Liu; Chunxiang, Xu

    2001-05-01

    Single-layer light-emitting diodes (LEDs) are fabricated using a mixture of a blue-emitting polymer and green-emitting 9, 10-bis(phenylethynyl)anthracene as emitting layer. The blend device with these two components in the emitting layer exhibits voltage-induced evolution of the electroluminescence. But when polystyrene is also blended into the emitting layer, the EL spectra show emission bands from both ether-PPV and BPEA in proportion to concentrations of the two materials, and the spectra exhibit no change with applied voltage. This implies that doping inert polymer is helpful in suppressing voltage-induced evolution of electroluminescence in LED blends.

  18. The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye: A Discovery-Oriented Capstone Project for the Second-Year Organic Laboratory

    ERIC Educational Resources Information Center

    Mascarenhas, Cheryl M.

    2008-01-01

    In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR, under basic conditions. The three naphthyl acetate derivatives used in this study are 2-naphthyl acetate (1a), 6-bromo-2-naphthyl acetate (1b) and 1,6-dibromo-2-naphthyl acetate (1c). The two-step, one-pot…

  19. Solvatochromism, Reversible Chromism and Self-Assembly Effects of Heteroatom-Assisted Aggregation-Induced Enhanced Emission (AIEE) Compounds.

    PubMed

    Niu, Caixia; You, Ying; Zhao, Liu; He, Dacheng; Na, Na; Ouyang, Jin

    2015-09-28

    Two compounds, 9,10-bis[2-(quinolyl)vinyl]anthracene (BQVA) and 9,10-bis[2-(naphthalen-2-yl)vinyl]anthracene (BNVA), have been synthesised and investigated. Both of them have aggregation-induced enhanced emission (AIEE) properties. Heteroatom-assisted BQVA shows solvatochromism, reversible chromism properties and self-assembly effects. When increasing the solvent polarities, the green solution of BQVA turns to orange with a redshift of the fluorescence emission wavelengths from λ=527 to 565 nm. Notably, BQVA exhibits reversible chromism properties, including mechano- and thermochromism. The as-prepared BQVA powders show green fluorescence (λem=525 nm) and the colour can turn into orange (λem=573 nm) after grinding. Interestingly, the orange colour can return at high temperature. Based on these reversible chromism properties, a simple and convenient erasable board has been designed. Different from BQVA, non-heteroatom-assisted BNVA has no clear chromic processes. The results obtained from XRD, differential scanning calorimetry, single-crystal analysis and theoretical calculations indicate that the chromic processes depend on the heteroatoms in BQVA. Additionally, BQVA also exhibits excellent self-assembly effects in different solvents. Homogeneous nanospheres are formed in mixtures of tetrahydrofuran and water, which are then doped into silica nanoparticles and treated with 3-aminopropyltriethoxysilane to give amino-functionalised nanoparticles (BQVA-AFNPs). The BQVAAFNPs could be used to stain protein markers in polyacrylamide gel electrophoresis.

  20. Investigation of Förster-type energy transfer in organic light-emitting devices with 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethy ljulolidin-4-yl-vinyl)-4H-pyran doped cohost emitting layer

    NASA Astrophysics Data System (ADS)

    Yu, Li-Zhen; Jiang, Xue-Yin; Zhang, Zhi-Lin; Lou, Li-Ren; Lee, Ching-Ting

    2009-01-01

    Organic light-emitting devices (OLEDs) with cohosted emitter, which is composed of 9,10-di(2-naphthyl)anthracene (ADN) and tris(8-hydroxy-quinolinato) aluminum (Alq3) and doped with 4-(dicyanomethylene)-2-t-butyl-6-(1,1,7,7-tetramethy ljulolidin-4-yl-vinyl)-4H-pyran (DCJTB), were fabricated and studied. The efficiency of OLEDs with a cohost emitter was higher than that with a single host emitter. For the cohost emitter with ADN/Alq3 weight ratio of 75:25, the 3.4 cd/A efficiency of the resulted OLEDs was obtained. It is found that the absorption spectra of DCJTB and the emission spectra of Alq3 changed with the composition of the emitter. This phenomenon is attributed to the polarization effect. On the basis of the Förster's theory, the resulted overlap integral exhibits the highest value for this cohost emitter. The experimental results reveal that the cascade energy transfer plays an important role in the luminance efficiency enhancement of the cohost emitter in OLEDs.

  1. Improvement of efficiency and stability utilizing a wide band gap material as the host for red organic light-emitting diodes

    NASA Astrophysics Data System (ADS)

    Tang, Hao; Li, Ying; Wang, Xiuru; Wang, Wengen; Sun, Runguang

    2007-03-01

    We present red organic light-emitting diodes (OLEDs) with high efficiency and stability based on a wide band gap host material 9,10-di (2-naphthyl) anthracene (ADN). In these diodes, N,N'-bis(1-naphthyl)-N,N'-diphenyl-1, 1'-biphenyl-4,4'diamine(NPB) and tris-(8- ydroxy-quinoline) aluminium (Alq) are used as hole and electron transport layers, respectively. 2,3,6,7-tetrahydro-1,1,7,7,-tetramethyl- 1H,5H,11H-10-(2-benzothiazolyl) quinolizino-[9,9a,1gh] coumarin (C545T) and 4-(dicyano-methylene)-2- t-butyl-6-(1,1,7,7-tetramethyl-julolidyl-9-enyl)-4H-pyran (DCJTB) are co-doped into the ADN emitting layer. Utilizing the two-step energy transfer from ADN to C545T and then from C545T to DCJTB, we achieved pure red organic light-emitting devices, which showed improved optical and electrical characteristics. Compared with devices where the emitting layer is made of Alq and DCJTB, the emission efficiency and stability of the ADN-based devices are greatly improved and the turn-on voltage is also decreased. The co-doping technique provides a promising way of utilizing wide band gap materials as the host to make red OLEDs, which will be useful in improving the electroluminesent performance of devices and simplifying the process of fabricating full colour OLEDs.

  2. Localized surface plasmon effects of two dimensional lattice of metal nanoislands

    NASA Astrophysics Data System (ADS)

    Oda, Yukari; Shimada, Ryoko; Japan Women's University Team

    2015-03-01

    Localized surface plasmon (LSP) of metal nanoparticles results from non-propagating excitation of their conduction electrons coupled to the electromagnetic field. LSP localizes the electric field and enhances light emission from fluorescent materials. In this study, a two dimensional (2D) lattice of silver (Ag) nanoislands was fabricated by nanosphere lithography (NSL) method utilizing self-assembled, close-packed hexagonal structures of polystyrene spheres as the etching mask. This 2D lattice was subjected to the electric field for investigating a role of the periodicity of metal islands in the LSP effect. 9,10-di(2-naphthyl) anthracene (ADN), a well-known blue-emitting material in the field of electroluminescence, was used for the study of the enhancement of emission due to the LSP effect. Hybrid thin films of poly(methyl methacrylate) containing ADN were prepared with spin-casting onto the 2D lattice of Ag nanoislands. Transmission and photoluminescence measurements were conducted for these hybrid thin films at room temperature. Detailed results will be presented on site.

  3. Measurement of Small Molecule Diffusion in Carbon Dioxide Swollen Polymers using Fluorescence Nonradiative Energy Transfer

    NASA Astrophysics Data System (ADS)

    Watkins, James; Gupta, Ravi; Ramachandrarao, Vijay

    2001-03-01

    Diffusion coefficients of molecular probes in CO2-swollen polystyrene films were measured in situ using high-pressure fluorescence nonradiative energy transfer (NRET). Specifically, the diffusivities of decacyclene and BPEA (9,10- bis phenyl ethnyl Anthracene), relatively large fluorescence acceptor probes, were determined in real time using pyrene-labeled polystyrene as the corresponding energy donor in carbon dioxide-plasticized films. Decacyclene diffusivities were measured at 65 and 80 C and carbon dioxide pressures ranging from 62 to 144 bar, conditions near and well above the previously reported, solvent-depressed glass transition of polystyrene. Decacyclene diffusivity shows an increase of over 5 orders of magnitude upon CO2 sorption relative to the PS glass at ambient pressure and equivalent temperatures. BPEA exhibits similar behavior but diffuses about an order of magnitude faster than decacyclene in CO2 plasticized polystyrene under similar conditions.

  4. Multiphoton absorption in graphene and metal-organic frameworks

    NASA Astrophysics Data System (ADS)

    Weiqiang, Chen

    ) anthracene (An2Py))] (MOF 1a); (2) [Zn2(trans,trans -4,4 stilbenedicarboxylic acid (SDC))2(trans, trans-9, 10-bis (4-pyridylethenyl) anthracene (An2Py))]˙perylene (MOF 2) and (3) [Zn2(trans,trans-4,4 stilbenedicarboxylic acid (SDC))2(trans, trans-9, 10-bis (4-pyridylethenyl) anthracene (An2Py))]˙anthracene (MOF 3). We select the nonlinear optically active ligand (An2Py) based on well-established guiding principles in the architecting of chromophores with relatively large nonlinear optical properties to synthesize MOF 1a. Subsequently, two high quantum yielding chromophores are encapsulated into the pore spaces of MOF 1a to obtain MOFs 2 and 3. MEPL measurements show the crucial role of two-, three- and four-photon absorption in the excited PL from both the ligand and the MOFs in the solid-state form. Our experimental results reveal that MOF 1a exhibits largely enhanced MEPL compared to that of its ligand. This is induced by the rigidifying of the chromophore in the MOF framework which minimizes the aggregation-caused quenching. Further enhancement on the MEPL is achieved in MOFs 2 and 3. The Forster resonance energy transfer (FRET) between the host MOF and the guest molecules leads to such an enhancement. Our experimental finding provides possible solutions to aggregation-caused quenching in the MEPL of organic molecules in the solid-state form and discloses a fresh route for producing photonic materials and devices in the solid-state form.

  5. Screening of pi-basic naphthalene and anthracene amplifiers for pi-acidic synthetic pore sensors.

    PubMed

    Hagihara, Shinya; Gremaud, Ludovic; Bollot, Guillaume; Mareda, Jiri; Matile, Stefan

    2008-04-02

    Synthetic ion channels and pores attract current attention as multicomponent sensors in complex matrixes. This application requires the availability of reactive signal amplifiers that covalently capture analytes and drag them into the pore. pi-Basic 1,5-dialkoxynaphthalenes (1,5-DAN) are attractive amplifiers because aromatic electron donor-acceptor (AEDA) interactions account for their recognition within pi-acidic naphthalenediimide (NDI) rich synthetic pores. Focusing on amplifier design, we report here the synthesis of a complete collection of DAN and dialkoxyanthracene amplifiers, determine their oxidation potentials by cyclic voltammetry, and calculate their quadrupole moments. Blockage experiments reveal that subtle structural changes in regioisomeric DAN amplifiers can be registered within NDI pores. Frontier orbital overlap in AEDA complexes, oxidation potentials, and, to a lesser extent, quadrupole moments are shown to contribute to isomer recognition by synthetic pores. Particularly important with regard to practical applications of synthetic pores as multianalyte sensors, we further demonstrate that application of the lessons learned with DAN regioisomers to the expansion to dialkoxyanthracenes provides access to privileged amplifiers with submicromolar activity.

  6. The "anthracene problem": closed-form conjugated-circuit models of ring currents in linear polyacenes.

    PubMed

    Fowler, Patrick W; Myrvold, Wendy

    2011-11-17

    Conjugated-circuit models for induced π ring currents differ in the types of circuit that they include and the weights attached to them. Choice of circuits for general π systems can be expressed compactly in terms of matchings of the circuit-deleted molecular graph. Variants of the conjugated-circuit model for induced π currents are shown to have simple closed-form solutions for linear polyacenes. Despite differing assumptions about the effect of cycle area, all the models predict the most intense perimeter current in the central rings, in general agreement with ab initio current-density maps. All tend to overestimate the rate of increase with N of the central ring current for the [N]polyacene, in comparison with molecular-orbital treatments using ipsocentric ab initio, pseudo-π, and Hückel-London approaches.

  7. Rate Acceleration of the Retro Diels-Alder Reaction of Anthracene Cycloadducts by Polysiloxy Substituents

    DTIC Science & Technology

    1988-01-01

    Lindsey 13 yielded 9, 1O-dimethyl-2,3,6,7-tetramethoxyanthracene (13) by condensing veratrole (12) and acetaldehyde in the presence of sulfuric acid...combination of those cited by Boldt12 and Lindsey.13 To an ice cooled solution of veratrole (32 mL, 250 mmol) in acetic acid (125 mL) was slowly added...solution of veratrole (32 mL, 250 mmol) in acetic acid (125 mL) was slowly added an ice cooled solution of benzaldehyde ( 25 mL, 246 mmol) in methanol

  8. Optical nuclear polarization via hyperfine relaxation. Polarization mechanism in anthracene/tetracyanobenzene charge-transfer crystals

    NASA Astrophysics Data System (ADS)

    Allgeier, J.; Macho, V.; Stehlik, D.; Vieth, H. M.; Auch, W.; Von Schütz, J. U.

    1982-03-01

    The large optical nuclear polarization (ONP) found in A/TCNB crystals is due to relaxation caused by the mobility of triplet excitons. The ONP field dependence gives an excitonic hopping rate of 3 × 10 9 s -1 (at 300 K). Exclusion of ONP by static hyperfine interaction (LAC ONP) is based on results of rf ONP experiments which allow an unambiguous distinction between the two processes.

  9. Preparation, characterization, physical properties, and photoconducting behaviour of anthracene derivative nanowires

    NASA Astrophysics Data System (ADS)

    Xiao, Jinchong; Yin, Zongyou; Yang, Bo; Liu, Yi; Ji, Li; Guo, Jun; Huang, Ling; Liu, Xuewei; Yan, Qingyu; Zhang, Hua; Zhang, Qichun

    2011-11-01

    Organic nanowires of 9,10-dibromoanthracene (DBA) and 9,10-dicyanoanthracene (DCNA) were obtained by adding the THF solution of DBA/DCNA into water containing P123 surfactants. The as-prepared nanowires were characterized by UV-vis, fluorescence spectra, Field Emission Scanning Electron Microscopy (FESEM), and Transmission Electron Microscopy (TEM). We found that DBA and DCNA nanowires emitted green light rather than blue light for molecules in THF solution. The red-shift UV and fluorescent spectra of DBA and DCNA nanowires implied that these nanowires were formed through J-aggregation. The photoconducting study of DBA/DCNA nanowire-based network on rGO/SiO2/Si shows different photocurrent behaviors upon irradiation, which displayed that electron transfer from DCNA nanowire to rGO was stronger than that of DBA nanowires to rGO.Organic nanowires of 9,10-dibromoanthracene (DBA) and 9,10-dicyanoanthracene (DCNA) were obtained by adding the THF solution of DBA/DCNA into water containing P123 surfactants. The as-prepared nanowires were characterized by UV-vis, fluorescence spectra, Field Emission Scanning Electron Microscopy (FESEM), and Transmission Electron Microscopy (TEM). We found that DBA and DCNA nanowires emitted green light rather than blue light for molecules in THF solution. The red-shift UV and fluorescent spectra of DBA and DCNA nanowires implied that these nanowires were formed through J-aggregation. The photoconducting study of DBA/DCNA nanowire-based network on rGO/SiO2/Si shows different photocurrent behaviors upon irradiation, which displayed that electron transfer from DCNA nanowire to rGO was stronger than that of DBA nanowires to rGO. Electronic supplementary information (ESI) available: XRD patterns and simulations, and FT-IR spectra. CCDC reference numbers 840471. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c1nr10655d

  10. Temperature Dependence of D.C. and Pulsed Electroluminescence in Anthracene Crystals,

    DTIC Science & Technology

    appears. The spectral distribution of the electroluminescence is independent of the second electrode material, though differences in the time dependence ...shown in the different current and temperature dependence of the intensity of the major vibrational progression of the emission. Included argon

  11. Oxidation of anthracene and benzo[a]pyrene by laccases from Trametes versicolor

    SciTech Connect

    Collins, P.J.; Dobson, A.D.W.; Kotterman, M.J.J.; Field, J.A.

    1996-12-01

    Polycyclic aromatic hydrocarbons, particularly benzene homologs, are highly toxic organic pollutants. One of the three major groups of extracellular oxidative enzymes involved in the white rot fungal lignin degradative process are laccases. This study presents evidence indicating that laccase has a role in PAH oxidation by white rot fungi. 36 refs., 5 figs., 1 tab.

  12. Anthracene-based fluorescent nanoprobes for singlet oxygen detection in biological media.

    PubMed

    Bresolí-Obach, Roger; Nos, Jaume; Mora, Margarita; Sagristà, Maria Lluïsa; Ruiz-González, Rubén; Nonell, Santi

    2016-10-15

    We have developed a novel singlet oxygen nanoprobe based on 9,10-anthracenedipropionic acid covalently bound to mesoporous silica nanoparticles. The nanoparticle protects the probe from interactions with proteins, which detract from its ability to detect singlet oxygen. In vitro studies show that the nanoprobe is internalized by cells and is distributed throughout the cytoplasm, thus being capable of detecting intracellularly-generated singlet oxygen.

  13. Red organic light-emitting diodes based on wide band gap emitting material as the host utilizing two-step energy transfer

    NASA Astrophysics Data System (ADS)

    Haq, Khizar-ul; Shan-peng, Liu; Khan, M. A.; Jiang, X. Y.; Zhang, Z. L.; Zhu, W. Q.

    2008-03-01

    We demonstrated efficient red organic light-emitting diodes based on a host emitting system of 9,10-di(2-naphthyl)anthracene (ADN) co-doped with 4-(dicyano-methylene)-2-t-butyle-6- (1,1,7,7-tetramethyl-julolidyl-9-enyl)-4H-pyran (DCJTB) as a red dopant and 2,3,6,7- tetrahydro-1,1,7,7-tetramethyl-1H,5H,1 1H-10(2-benzothiazolyl)-quinolizine-[9,9a,1gh] coumarin (C545T) as an assistant dopant. The typical device structure was glass substrate/ITO/4,4',4''-tris(N-3-methylphenyl-N-phenylamino) triphenylamine(m-MTDATA)/N,N'-bis-(naphthalene-1-yl)-N,N'-diphenylbenzidine(NPB)/[ADN: DCJTB: C545T/Alq3/LiF/Al]. It was found that C545T dopant did not emit by itself but did assist the energy transfer from the host (ADN) to the red emitting dopant. The red OLEDs realized by this approach not only enhanced the emission color, but also significantly improved the EL efficiency. The EL efficiency reached 3.5 cd A-1 at a current density of 20 mA cm-2, which is enhanced by three times compared with devices where the emissive layer is composed of the DCJTB doped ADN. The saturated red emission was obtained with CIE coordinates (x = 0.618, y = 0.373) at 621 nm, and the device driving voltage is decreased as much as 38%. We attribute these improvements to the assistant dopant (C545T), which leads to the more efficient energy transfer from ADN to DCJTB. These results indicate that the co-doped system is a promising method for obtaining high-efficiency red OLEDs.

  14. Efficiency and Color Coordinate Improvement Using Codopants in Blue Organic Light-Emitting Diode

    NASA Astrophysics Data System (ADS)

    Wang, Xiu Ru; Chen, Jiang Shan; You, Han; Ma, Dong Ge; Sun, Run Guang

    2005-12-01

    The codoping method is applied to fabricate efficient blue organic light-emitting diodes (OLEDs). With the same structure of indium-tin oxide (ITO)/N,N'-bis(1-naphthyl)-N,N'-diphenyl-1,1'-biphenyl-4,4'diamine (NPB)(80 nm)/light-emitting layer (30 nm)/tris-(8-hydroxy-quinoline)aluminum (Alq3) (20 nm)/LiF (1 nm)/Al (120 nm), a set of three devices was manufactured for comparison. For Devices 1, 2, and 3, the light-emitting layers are 9,10-di(2-naphthyl)anthracene (ADN):4,4'-(1,4-phenylenedi-2,1-ethene diyl)bis[N,N-bis(4-methylphenyl)-benzenamine] (DPAVB) (1 wt %), ADN:2,5,8,11-tetra-(t-butyl)-perylene (TBPE) (1 wt %), and ADN:DPAVB (0.3 wt %):TBPE (0.7 wt %), respectively. It is found that the codoped Device 3 has the highest maximum luminance, Electroluminescence (EL) quantum efficiency and color saturation. Further study on the effect of the codopants was through a relative photoluminescence (PL) quantum efficiency measurement. The result shows that the relative PL efficiencies of Devices 1, 2, and 3 are 15.6, 19.3, and 24%, respectively, as determined using an integrating sphere system excited at 375 nm. The codoping method improves the EL efficiency intrinsically. Codopants of the heterogeneous light-emitting molecules may decrease the possibility of self-quenching from the interaction of the homogenous molecules at the same total doping concentration. Furthermore, the decrease in the interaction of homogenous molecules suppresses the light emission from the aggregations thus narrowing the emission spectrum, and results in saturated blue light emission.

  15. Color-stable, reduced efficiency roll-off hybrid white organic light emitting diodes with ultra high brightness

    NASA Astrophysics Data System (ADS)

    Liu, Bai-Quan; Tao, Hong; Su, Yue-Ju; Gao, Dong-Yu; Lan, Lin-Feng; Zou, Jian-Hua; Peng, Jun-Biao

    2013-07-01

    High-brightness and color-stable two-wavelength hybrid white organic light emitting diodes (HWOLEDs) with the configuration of indium tin oxide (ITO)/ N, N, N', N'-tetrakis(4-methoxyphenyl)-benzidine (MeO-TPD): tetrafluoro-tetracyanoqino dimethane (F4-TCNQ)/N,N'-di(naphthalene-1-yl)-N,N'-diphenyl-benzidine (NPB)/4,4-N,N-dicarbazolebiphenyl (CBP): iridium (III) diazine complexes (MPPZ)2Ir(acac)/NPB/2-methyl-9,10-di(2-naphthyl)anthracene (MADN): p-bis(p-N,N-di-phenyl-aminostyryl)benzene (DSA-ph)/ bis(10-hydroxybenzo[h] quinolinato)beryllium complex (Bebq2)/LiF/Al have been fabricated and characterized. The optimal brightness of the device is 69932 cd/m2 at a voltage of 13 V, and the Commission Internationale de l'Eclairage (CIE) chromaticity coordinates are almost constant during a large voltage change of 6-12 V. Furthermore, a current efficiency of 15.3 cd/A at an illumination-relevant brightness of 1000 cd/m2 is obtained, which rolls off slightly to 13.0 cd/A at an ultra high brightness of 50000 cd/m2 . We attribute this great performance to wisely selecting an appropriate spacer together with effectively utilizing the combinations of exciton-harvested orange-phosphorescence/ blue-fluorescence in the device. Undoubtedly, this is one of the most exciting results in two-wavelength HWOLEDs up to now.

  16. Synthesis, potentiometric, kinetic, and NMR Studies of 1,4,7,10-tetraazacyclododecane-1,7-bis(acetic acid)-4,10-bis(methylenephosphonic acid) (DO2A2P) and its complexes with Ca(II), Cu(II), Zn(II) and lanthanide(III) ions.

    PubMed

    Kálmán, Ferenc K; Baranyai, Zsolt; Tóth, Imre; Bányai, István; Király, Róbert; Brücher, Ernö; Aime, Silvio; Sun, Xiankai; Sherry, A Dean; Kovács, Zoltán

    2008-05-05

    A cyclen-based ligand containing trans-acetate and trans-methylenephosphonate pendant groups, H 6DO2A2P, was synthesized and its protonation constants (12.6, 11.43, 5.95, 6.15, 2.88, and 2.77) were determined by pH-potentiometry and (1)H NMR spectroscopy. The first two protonations were shown to occur at the two macrocyclic ring N-CH 2-PO 3 (2-) nitrogens while the third and fourth protonations occur at the two phosphonate groups. In parallel with protonation of the two -PO 3 (2-) groups, the protons from the NH (+)-CH 2-PO 3 (2-) are transferred to the N-CH 2-COO (-) nitrogens. The stability constants of the Ca (2+), Cu (2+), and Zn (2+) (ML, MHL, MH 2L, and M 2L) complexes were determined by direct pH-potentiometry. Lanthanide(III) ions (Ln (3+)) form similar species, but the formation of complexes is slow; so, "out-of-cell" pH-potentiometry (La (3+), Eu (3+), Gd (3+), Y (3+)) and competitive spectrophotometry with Cu(II) ion (Lu (3+)) were used to determine the stability constants. By comparing the log K ML values with those of the corresponding DOTA (H 4DOTA = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid) and DOTP (H 8DOTP = 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetramethylenephosphonic acid) complexes, the order DOTA < DO2A2P < DOTP was found for all the metal ion complexes examined here with the exception of the Ca (2+) complexes, for which the order is reversed. The relaxivity of Gd(DO2A2P) decreases between pH 2 and 7 but remains constant in the pH range of 7 < pH < 12 ( r 1 = 3.6 mM (-1) s (-1)). The linewiths of the (17)O NMR signals of water in the absence and presence of Gd(DO2A2P) (at pH = 3.45 and 8.5) between 274 and 350 K are practically the same, characteristic of a q = 0 complex. Detailed kinetic studies of the Ce (3+) and Gd (3+) complexes with DO2A2P showed that complex formation is slow and involves a high stability diprotonated intermediate Ln(H 2DO2A2P)*. Rearrangement of the diprotonated intermediate into the final complex is an OH (-) assisted process but, unlike formation of Ln(DOTA) complexes, rearrangement of Ln(H 2DO2A2P)* also takes place spontaneously likely as a result of transfer of one of the protons from a ring nitrogen to a phosphonate group. The order of the OH (-) assisted formation rates of complexes is DOTA > DO2A2P > DOTP while the order of the proton assisted dissociation rates of the Gd (3+) complexes is reversed, DOTP > DO2A2P > DOTA. (1)H and (13)C NMR spectra of Eu(DO2A2P) and Lu(DO2A2P) were assigned using two-dimensional correlation spectroscopy (2D COSY), heteronuclear multiple quantum coherence (HMQC), heteronuclear chemical shift correlation (HETCOR), and exchange spectroscopy (EXSY) NMR methods. Two sets of (1)H NMR signals were observed for Eu(DO2A2P) characteristic of the presence of two coordination isomers in solution, a twisted square antiprism (TSAP) and a square antiprism (SAP), in the ratio of ~93% and ~7%, respectively. Line shape analysis of the (1)H NMR spectra of Lu(DO2A2P) gave lower activation parameters compared to La(DOTP) for interconversion between coordination isomers. This indicates that the Ln(DO2A2P) complexes are less rigid probably due to the different size and spatial requirements of the carboxylate and phosphonate groups.

  17. Host-guest complexation of cucurbit[8]uril with two enantiomers

    NASA Astrophysics Data System (ADS)

    Gao, Zhong-Zheng; Lin, Rui-Lian; Bai, Dong; Tao, Zhu; Liu, Jing-Xin; Xiao, Xin

    2017-03-01

    Host-guest complexation of cucurbit[8]uril (Q[8]) with two enantiomers, D-3-(2-naphthyl)-alanine (D-NA) and L-3-(2-naphthyl)-alanine (L-NA), has been fully investigated. Experimental data indicate that double guests reside within the cavity of Q[8] in both aqueous solution and solid state, generating highly stable homoternary complexes D-NA2@Q[8] and L-NA2@Q[8].

  18. Host-guest complexation of cucurbit[8]uril with two enantiomers

    PubMed Central

    Gao, Zhong-Zheng; Lin, Rui-Lian; Bai, Dong; Tao, Zhu; Liu, Jing-Xin; Xiao, Xin

    2017-01-01

    Host-guest complexation of cucurbit[8]uril (Q[8]) with two enantiomers, D-3-(2-naphthyl)-alanine (D-NA) and L-3-(2-naphthyl)-alanine (L-NA), has been fully investigated. Experimental data indicate that double guests reside within the cavity of Q[8] in both aqueous solution and solid state, generating highly stable homoternary complexes D-NA2@Q[8] and L-NA2@Q[8]. PMID:28300189

  19. Bromelain nanoparticles protect against 7,12-dimethylbenz[a]anthracene induced skin carcinogenesis in mouse model.

    PubMed

    Bhatnagar, Priyanka; Pant, Aditya B; Shukla, Yogeshwer; Chaudhari, Bhushan; Kumar, Pradeep; Gupta, Kailash C

    2015-04-01

    Conventional cancer chemotherapy leads to severe side effects, which limits its use. Nanoparticles (NPs) based delivery systems offer an effective alternative. Several evidences highlight the importance of Bromelain (BL), a proteolytic enzyme, as an anti-tumor agent which however has been limited due to the requirement of high doses at the tumor site. Therefore, we illustrate the development of BL loaded poly (lactic-co-glycolic acid) NPs that show enhanced anti-tumor effects compared to free BL. The formulated NPs with a mean particle size of 130.4 ± 8.81 nm exhibited sustained release of BL. Subsequent investigation revealed enhanced anti-tumor ability of NPs in 2-stage skin tumorigenesis mice model. Reduction in average number of tumors (∼ 2.3 folds), delay in tumorigenesis (∼ 2 weeks), percent tumorigenesis (∼ 4 folds), and percent mortality rate as well as a reduction in the average tumor volume (∼ 2.5 folds) in mice as compared to free BL were observed. The NPs were found to be superior in exerting chemopreventive effects over chemotherapeutic effects at 10 fold reduced dose than free BL, validated by the enhanced ability of NPs (∼ 1.8 folds) to protect the DNA from induced damage. The effects were also supported by histopathological evaluations. NPs were also capable of modulating the expression of pro-apoptotic (P53, Bax) and anti-apoptotic (Bcl2) proteins. Therefore, our findings demonstrate that developed NPs formulation could be used to improve the efficacy of chemotherapy by exerting chemo-preventive effects against induced carcinogenesis at lower dosages.

  20. ANTHRACENE PHOTOINDUCED TOXICITY TO PLHC-1 CELL LINE (POECILIOPSIS LUCIDA) AND THE ROLE OF LIPID PEROXIDATION IN TOXICITY. (R823873)

    EPA Science Inventory

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  1. Decreased adrenal medullary tyrosine hydroxylase mRNA in DMBA (7,12-dimethylbenz(a)anthracene)-induced mammary carcinoma

    SciTech Connect

    Bunce, O.R.; Badary, O.A.; Abou El-Ela, S.; Hartle, D.K. )

    1991-03-15

    Adrenal cortical hormones suppress initiation and promotion of DMBA-induced mammary tumorigenesis. The authors found a positive correlation between presence of DMBA-induced adrenal cortical necrosis and mammary tumor incidence. Because they find adrenal medullary as well as cortical lesions in tumor bearing (TB) DMBA-treated rats, they evaluated medullary function by quantitating hybridized cDNA- TH-S{sup 35} with in situ TH-mRNA u sing computer assisted quantitative autoradiographic technique. Virgin female Sprague-Dawley rats were given a 10 mg i.g. dose of DMBA. Three wks later, rats were placed on 20% polyunsaturated (PUFA) fat diets containing omega-6 and omega-3 fatty acids. All were killed 15 wks post-DMBA. TH-mRNA levels in adrenal medullae of TB animals were decreased compared to non-TB rats. Histopathology indicated a high incidence of medullary necrosis in TB rats, whereas, adrenal necrosis did not occur in non-TB animals. Adrenal necrosis correlated positively with tumor burden, but no correlation was found between incidence of adrenal lesions and type of PUFA in the diet. The authors suggest that DMBA adrenal necrosis may reduce TH-mRNA in the medulla, compromise its catecholamine synthetic capability, and thereby contribute to the overall metabolic stress condition of TB rats.

  2. Induction of apoptosis by calcium D-glucarate in 7,12-dimethyl benz [a] anthracene-exposed mouse skin.

    PubMed

    Singh, Jaya; Gupta, Krishna P

    2007-01-01

    Calcium glucarate (Cag), a naturally occurring nontoxic compound, suppresses the DMBA-induced tumor development in mouse skin. In the process of understanding the mechanisms of tumor suppression by Cag, we investigated the effect of topical application of Cag on selective and critical events of apoptotic pathway in DMBA-exposed mouse epidermis. Varied doses of DMBA or Cag were used for the study. DMBA had an inhibitory effect on proteases in general and on caspases in particular. Cag tried to reverse the inhibitory effect of DMBA on 3, 8, or 9 caspase in a dose-dependent manner. Cag inhibited activity of Poly ADP-ribose polymerase enzyme, a substrate of caspses, after DMBA exposure. As indicated by western blotting, Cag treatment also inhibited PARP expression induced by DMBA at the level of protein. Cag induced the DMBA-inhibited Ca++/Mg++-dependent endonuclease, an enzyme responsible for the DNA fragmentation during apoptosis. DMBA induced the expression of mutant-p53 and Bcl-2. This induced expression of proteins was reversed when Cag was given along with DMBA. Cag showed a dose-dependent inhibition of DMBA-induced mutant-p53 expression. Similarly Bcl-2 overexpression by DMBA was also inhibited by topical treatment of Cag when given along with DMBA. Inhibition of mutant-p53 and Bcl-2 expression by Cag in DMBA-exposed mouse skin might contribute to the apoptogenic effect possibly exerted by Cag while suppressing the tumor development. The study indicates that Cag induces apoptosis in mouse epidermis, a possible mechanism for tumor suppression, and thus could be considered a promising anticancer agent.

  3. Exploring the Intrinsic Piezofluorochromic Mechanism of TPE-An by STS Technique.

    PubMed

    Jin, Shunyu; Tian, Yan; Liu, Fei; Deng, Shaozhi; Chen, Jun; Xu, Ningsheng

    2015-12-01

    9,10-bis(4-(1,2,2-triphenylvinyl)styryl)anthracene (TPE-An) materials have attracted considerable attention in recent years because they have high luminescence efficiency and excellent piezofluorochromic properties, which have potential applications in organic light-emitting display (OLED) area. Scanning tunneling spectroscopy (STS) technique was used to study the piezofluorochromic mechanism of aggregation-induced emission (AIE) materials for the first time. Photoluminescence (PL) experiments revealed that the emission peak of TPE-An is observed to exhibit a red-shift with the increase of the grinding time. A theoretical calculation was carried out to find the relationship between the bandgap of TPE-An and the external force by combination of the classical tunneling theory and STS results. It is found that when the pressure variation on the surface of TPE-An film was increased to be over 4.38 × 10(4) Pa, the shrink of the highest occupied molecular orbital (HOMO)-lowest unoccupied molecular orbital (LUMO) gap can arrive at 1.1 eV. It is concluded that the piezofluorochromic behaviors of TPE-An should originate from the shrinking effect of the bandgap under external force. Moreover, this research method may shed light on comprehending and adjusting the piezofluorochromic characters of other AIE materials.

  4. Quick Fabrication of Large-area Organic Semiconductor Single Crystal Arrays with a Rapid Annealing Self-Solution-Shearing Method

    PubMed Central

    Li, Yunze; Ji, Deyang; Liu, Jie; Yao, Yifan; Fu, Xiaolong; Zhu, Weigang; Xu, Chunhui; Dong, Huanli; Li, Jingze; Hu, Wenping

    2015-01-01

    In this paper, we developed a new method to produce large-area single crystal arrays by using the organic semiconductor 9, 10-bis (phenylethynyl) anthracene (BPEA). This method involves an easy operation, is efficient, meets the demands of being low-cost and is independent of the substrate for large-area arrays fabrication. Based on these single crystal arrays, the organic field effect transistors exhibit the superior performance with the average mobility extracting from the saturation region of 0.2 cm2 V−1s−1 (the highest 0.47 cm2 V−1s−1) and on/off ratio exceeding 105. In addition, our single crystal arrays also show a very high photoswitch performance with an on/off current ratio up to 4.1 × 105, which is one of the highest values reported for organic materials. It is believed that this method provides a new way to fabricate single crystal arrays and has the potential for application to large area organic electronics. PMID:26282460

  5. Cadmium coordination polymers based on flexible bis(imidazole) ligands: A rare example for doublet of doublet cadmium polyhedron arrangements

    NASA Astrophysics Data System (ADS)

    Babu, Chatla Naga; Suresh, Paladugu; Sampath, Natarajan; Prabusankar, Ganesan

    2014-10-01

    Two one-dimensional (1D) coordination polymers, [{LCd(O2NO)2(DMF)2}2{(LCd(O2NO)2(DMF))(DMF)}2]n (1) and [L‧Cd(O2NO)(ONO2)(DMF)2]n (2), having an aryl chromophoric unit and a flexible bis(imidazole) tail, 9,10-bis{(benzimidazol)methyl}anthracene (L) and 1,4-bis{(imidazol)methyl}benzene (L‧), with various coordination modes have been obtained. Molecule 1 represents the first structurally characterized one dimensional coordination polymer consisting of both hepta- and octa-coordinated cadmium centers. In 1, two distorted pentagonal bipyramidal Cd(II) centers and two distorted triangular dodecahedral Cd(II) centers are alternately arranged via bridging bidentate N,N-chelating ligand, L. Whereas, a distorted pentagonal bipyramidal Cd(II) center is formed in 2 where the sterically less crowded L‧ serves as a bridging bidentate N,N-chelating ligand. Furthermore, 1 and 2 have been characterized by elemental analysis, FT-IR, 1H NMR, UV-vis and fluorescent techniques.

  6. Quick Fabrication of Large-area Organic Semiconductor Single Crystal Arrays with a Rapid Annealing Self-Solution-Shearing Method

    NASA Astrophysics Data System (ADS)

    Li, Yunze; Ji, Deyang; Liu, Jie; Yao, Yifan; Fu, Xiaolong; Zhu, Weigang; Xu, Chunhui; Dong, Huanli; Li, Jingze; Hu, Wenping

    2015-08-01

    In this paper, we developed a new method to produce large-area single crystal arrays by using the organic semiconductor 9, 10-bis (phenylethynyl) anthracene (BPEA). This method involves an easy operation, is efficient, meets the demands of being low-cost and is independent of the substrate for large-area arrays fabrication. Based on these single crystal arrays, the organic field effect transistors exhibit the superior performance with the average mobility extracting from the saturation region of 0.2 cm2 V-1s-1 (the highest 0.47 cm2 V-1s-1) and on/off ratio exceeding 105. In addition, our single crystal arrays also show a very high photoswitch performance with an on/off current ratio up to 4.1 × 105, which is one of the highest values reported for organic materials. It is believed that this method provides a new way to fabricate single crystal arrays and has the potential for application to large area organic electronics.

  7. A microfluidic system for evaluation of antioxidant capacity based on a peroxyoxalate chemiluminescence assay.

    PubMed

    Amatatongchai, Maliwan; Hofmann, Oliver; Nacapricha, Duangjai; Chailapakul, Orawon; deMello, Andrew J

    2007-01-01

    A microfluidic system incorporating chemiluminescence detection is reported as a new tool for measuring antioxidant capacity. The detection is based on a peroxyoxalate chemiluminescence (PO-CL) assay with 9,10-bis-(phenylethynyl)anthracene (BPEA) as the fluorescent probe and hydrogen peroxide as the oxidant. Antioxidant plugs injected into the hydrogen peroxide stream result in inhibition of the CL emission which can be quantified and correlated with antioxidant capacity. The PO-CL assay is performed in 800-microm-wide and 800-microm-deep microchannels on a poly(dimethylsiloxane) (PDMS) microchip. Controlled injection of the antioxidant plugs is performed through an injection valve. Of the plant-food based antioxidants tested, beta-carotene was found to be the most efficient hydrogen peroxide scavenger (SAHP of 3.27x10(-3) micromol-1 L), followed by alpha-tocopherol (SAHP of 2.36x10(-3) micromol-1 L) and quercetin (SAHP of 0.31x10(-3) micromol-1 L). Although the method is inherently simple and rapid, excellent analytical performance is afforded in terms of sensitivity, dynamic range, and precision, with RSD values typically below 1.5%. We expect our microfluidic devices to be used for in-the-field antioxidant capacity screening of plant-sourced food and pharmaceutical supplements.

  8. Quick Fabrication of Large-area Organic Semiconductor Single Crystal Arrays with a Rapid Annealing Self-Solution-Shearing Method.

    PubMed

    Li, Yunze; Ji, Deyang; Liu, Jie; Yao, Yifan; Fu, Xiaolong; Zhu, Weigang; Xu, Chunhui; Dong, Huanli; Li, Jingze; Hu, Wenping

    2015-08-18

    In this paper, we developed a new method to produce large-area single crystal arrays by using the organic semiconductor 9, 10-bis (phenylethynyl) anthracene (BPEA). This method involves an easy operation, is efficient, meets the demands of being low-cost and is independent of the substrate for large-area arrays fabrication. Based on these single crystal arrays, the organic field effect transistors exhibit the superior performance with the average mobility extracting from the saturation region of 0.2 cm(2) V(-1)s(-1) (the highest 0.47 cm(2) V(-1)s(-1)) and on/off ratio exceeding 10(5). In addition, our single crystal arrays also show a very high photoswitch performance with an on/off current ratio up to 4.1 × 10(5), which is one of the highest values reported for organic materials. It is believed that this method provides a new way to fabricate single crystal arrays and has the potential for application to large area organic electronics.

  9. The effect of chemical structure on the stability of physical vapor deposited glasses of 1,3,5-triarylbenzene

    NASA Astrophysics Data System (ADS)

    Liu, Tianyi; Cheng, Kevin; Salami-Ranjbaran, Elmira; Gao, Feng; Li, Chen; Tong, Xiao; Lin, Yi-Chih; Zhang, Yue; Zhang, William; Klinge, Lindsey; Walsh, Patrick J.; Fakhraai, Zahra

    2015-08-01

    We detail the formation and properties associated with stable glasses (SG) formed by a series of structural analogues of 1,3-bis(1-naphthyl)-5-(2-naphthyl)benzene (α,α,β-TNB), a well-studied SG former. Five compounds with similar structural properties were synthesized and physical vapor-deposited with a constant deposition rate at various substrate temperatures (Tdep) in the range between 0.73 Tg and 0.96 Tg. These molecules include α,α,β-TNB, 3,5-di(naphthalen-1-yl)-1-phenylbenzene (α,α-P), 9-(3,5-di(naphthalen-1-yl)phenyl)anthracene (α,α-A), 9,9'-(5-(naphthalen-2-yl)-1,3-phenylene)dianthracene (β-AA), and 3,3',5,5'-tetra(naphthalen-1-yl)-1,1'-biphenyl (α,α,α,α-TNBP). Ellipsometry was used to study the transformations from the as-deposited glasses into ordinary glasses (OG). The stability of each film was evaluated by measuring the fictive temperature (Tf) and density difference between the as-deposited glass and OG. It is demonstrated that all five molecules can form SGs upon vapor deposition in this temperature range. In-depth studies on the dependence of the stability of as-deposited glasses upon Tdep were performed with three molecules, α,α,β-TNB, α,α-P, and α,α-A. The general trends of stability were comparable at the same Tdep/Tg for these three compounds. Similar to previous studies on α,α,β-TNB, vapor-deposited glasses of α,α-P and α,α-A formed the most stable structures around Tdep = 0.8-0.85 Tg. The most stable glass of each molecule showed the lowest thermal expansion coefficient compared to OG and a positive optical birefringence. However, the SGs of α,α-A were less stable compared to α,α-P and α,α,β-TNB at the relative Tdep/Tg. Based on Arrhenius extrapolation of the aging time, as a measure of stability, the most stable α,α-A glass was only aged for a few years as opposed to hundreds or thousands of years for other glasses. We hypothesize that the reduced stability is due to slower mobility at the free surface of

  10. White organic light-emitting devices with high color purity and stability

    NASA Astrophysics Data System (ADS)

    Bai, Yajie; Liu, Su; Li, Hairong; Liu, Chunjuan; Wang, Jinshun; Chang, Jinxian

    2014-04-01

    A white organic light-emitting device (WOLED) with dual-emitting layers was presented, in which the blue fluorescent dye 2,5,8,11-terta-tertbutylperylene (TBPe) was doped in 2-methyl-9, 10-di(2-naphthyl)-anthracene (MADN) as a blue-emitting layer, while 5,6,11,12-tetraphenylnaphthacene (rubrene, Rb) was doped in the above-mentioned materials as a yellow-emitting layer. The fabricated monochromatic devices using the blue- and yellow-emitting layer have demonstrated that the direct charge trapping mechanism is the dominant emission mechanism in the yellow OLED. Studies on the WOLEDs with dual-emitting layers have shown that the performances of these devices are strongly susceptible to the thickness of the emitting layer and the stack order of two emitting layers. Structure of ITO(160 nm)/NPB(30 nm)/MADN: 5 wt%TBPe: 3 wt%Rb(10 nm)/MADN: 5 wt%TBPe(20 nm)/BCP (10 nm)/Alq3(20 nm)/Al(100 nm) was determined to be the most favorable WOLED. The maximum luminance of 16 000 cd cm-2 at the applied voltage of 13.4 V and Commission International de 1‧Eclairage (CIE) coordinates of (0.3263, 0.3437) which is closer to the standard white light (CIE (0.33, 0.33)) than the most recent reported WOLEDs were obtained. Moreover, there is just slight variation of CIE coordinates (ΔCIEx, y = 0.0171, 0.0167; corresponding Δu‧v‧ = 0.0119) when the current density increases from 10 to 100 mA cm-2. It reveals that the emissive dopant Rb acts as charge traps to improve electron-hole balance, provides sites for electron-hole recombination and thus makes carriers distribute more evenly in the dual-emitting layers which broaden the recombination zone and improve the stability of the CIE coordinates.

  11. Red-light-controllable liquid-crystal soft actuators via low-power excited upconversion based on triplet-triplet annihilation.

    PubMed

    Jiang, Zhen; Xu, Ming; Li, Fuyou; Yu, Yanlei

    2013-11-06

    A red-light-controllable soft actuator has been achieved, driven by low-power excited triplet-triplet annihilation-based upconversion luminescence (TTA-UCL). First, a red-to-blue TTA-based upconversion system with a high absolute quantum yield of 9.3 ± 0.5% was prepared by utilizing platinum(II) tetraphenyltetrabenzoporphyrin (PtTPBP) as the sensitizer and 9,10-bis(diphenylphosphoryl)anthracene (BDPPA) as the annihilator. In order to be employed as a highly effective phototrigger of photodeformable cross-linked liquid-crystal polymers (CLCPs), the PtTPBP&BDPPA system was incorporated into a rubbery polyurethane film and then assembled with an azotolane-containing CLCP film. The generating assembly film bent toward the light source when irradiated with a 635 nm laser at low power density of 200 mW cm(-2) because the TTA-UCL was effectively utilized by the azotolane moieties in the CLCP film, inducing their trans-cis photoisomerization and an alignment change of the mesogens via an emission-reabsorption process. It is the first example of a soft actuator in which the TTA-UCL is trapped and utilized to create photomechanical effect. Such advantages of using this novel red-light-controllable soft actuator in potential biological applications have also been demonstrated as negligible thermal effect and its excellent penetration ability into tissues. This work not only provides a novel photomanipulated soft actuation material system based on the TTA-UCL technology but also introduces a new technological application of the TTA-based upconversion system in photonic devices.

  12. Vertical Single-Crystalline Organic Nanowires on Graphene: Solution-Phase Epitaxy and Optical Microcavities.

    PubMed

    Zheng, Jian-Yao; Xu, Hongjun; Wang, Jing Jing; Winters, Sinéad; Motta, Carlo; Karademir, Ertuğrul; Zhu, Weigang; Varrla, Eswaraiah; Duesberg, Georg S; Sanvito, Stefano; Hu, Wenping; Donegan, John F

    2016-08-10

    Vertically aligned nanowires (NWs) of single crystal semiconductors have attracted a great deal of interest in the past few years. They have strong potential to be used in device structures with high density and with intriguing optoelectronic properties. However, fabricating such nanowire structures using organic semiconducting materials remains technically challenging. Here we report a simple procedure for the synthesis of crystalline 9,10-bis(phenylethynyl) anthracene (BPEA) NWs on a graphene surface utilizing a solution-phase van der Waals (vdW) epitaxial strategy. The wires are found to grow preferentially in a vertical direction on the surface of graphene. Structural characterization and first-principles ab initio simulations were performed to investigate the epitaxial growth and the molecular orientation of the BPEA molecules on graphene was studied, revealing the role of interactions at the graphene-BPEA interface in determining the molecular orientation. These free-standing NWs showed not only efficient optical waveguiding with low loss along the NW but also confinement of light between the two end facets of the NW forming a microcavity Fabry-Pérot resonator. From an analysis of the optical dispersion within such NW microcavities, we observed strong slowing of the waveguided light with a group velocity reduced to one-tenth the speed of light. Applications of the vertical single-crystalline organic NWs grown on graphene will benefit from a combination of the unique electronic properties and flexibility of graphene and the tunable optical and electronic properties of organic NWs. Therefore, these vertical organic NW arrays on graphene offer the potential for realizing future on-chip light sources.

  13. Protective effect of Ocimum sanctum on 3-methylcholanthrene, 7,12-dimethylbenz(a)anthracene and aflatoxin B1 induced skin tumorigenesis in mice

    SciTech Connect

    Rastogi, Shipra; Shukla, Yogeshwer; Paul, Bhola N.; Chowdhuri, D. Kar; Khanna, Subhash K.; Das, Mukul

    2007-11-01

    A study on the protective effect of alcoholic extract of the leaves of Ocimum sanctum on 3-mthylcholanthrene (MCA), 7,12-dimethylbenzanthracene (DMBA) and aflatoxin B{sub 1} (AFB{sub 1}) induced skin tumorigenesis in a mouse model has been investigated. The study involved pretreatment of mice with the leaf extract prior to either MCA application or tetradecanoyl phorbol acetate (TPA) treatment in a two-stage tumor protocol viz a viz, DMBA/TPA and AFB1/TPA. The results of the present study indicate that the pretreatment with alcoholic extract of the leaves of O. sanctum decreased the number of tumors in MCA, DMBA/TPA and AFB1/TPA treated mice. The skin tumor induced animals pretreated with alcoholic extract led to a decrease in the expression of cutaneous {gamma}-glutamyl transpeptidase (GGT) and glutathione-S-transferase-P (GST-P) protein. The histopathological examination of skin tumors treated with leaf extract showed increased infiltration of polymorphonuclear, mononuclear and lymphocytic cells, decreased ornithine decarboxylase activity with concomitant enhancement of interleukin-1{beta} (IL-1{beta}) and tumor necrosis factor-{alpha} (TNF-{alpha}) in the serum, implying the in vivo antiproliferative and immunomodulatory activity of leaf extract. The decrease in cutaneous phase I enzymes and elevation of phase II enzymes in response to topical application of leaf extract prior to MCA, AFB1, DMBA/TPA and AFB1/TPA treatment indicate the possibility of impairment in reactive metabolite(s) formation and thereby reducing skin carcinogenicity. Furthermore, pretreatment of leaf extract in the carcinogen induced animals resulted in elevation of glutathione levels and decrease in lipid peroxidation along with heat shock protein expression, indicating a scavenging or antioxidant potential of the extract during chemical carcinogenesis. Thus it can be concluded that leaf extract of O. sanctum provides protection against chemical carcinogenesis in one or more of the following mechanisms: (i) by acting as an antioxidant; (ii) by modulating phase I and II enzymes; (iii) by exhibiting antiproliferative activity.

  14. EVIDENCE OF OXIDATIVE STRESS IN BLUEGILL SUNFISH (LEPOMIS MACROCHIRUS) LIVER MICROSOMES SIMULTANEOUSLY EXPOSURE TO SOLAR ULTRAVIOLET RADIATION AND ANTHRACENE. (R823873)

    EPA Science Inventory

    The perspectives, information and conclusions conveyed in research project abstracts, progress reports, final reports, journal abstracts and journal publications convey the viewpoints of the principal investigator and may not represent the views and policies of ORD and EPA. Concl...

  15. The effect of the aromatase inhibitor, 4-(phenylthio)-4-androstene-3,17-dione, on dimethylbenz(A)anthracene-induced rat mammary tumors.

    PubMed

    Abul-Hajj, Y J

    1989-01-01

    4-(Phenylthio)-4-androstene-3,17-dione (4-PTAD), a known inhibitor of human placental aromatase, was examined as a growth inhibitor of DMBA-induced rat mammary tumors. Subcutaneous administration of 4-PTAD at dose levels of 25 or 50 mg/kg/day caused a significant decrease in hormone-dependent tumor growth. Resumption of tumor growth occurred when either the administration of inhibitor was stopped or when inhibitor was coadministered with estradiol indicating that suppression of tumor growth was due to inhibition of estrogen biosynthesis. Additionally, plasma levels of estradiol were found to be lower in the animals treated with 4-PTAD. The major metabolite of 4-PTAD in vitro was identified as 4-(phenylthio)-4-androstene-17 beta-ol-3-one and was found to have 60% of the aromatase inhibitory activity of 4-PTAD.

  16. Degradation of Pyrene, Benz[a]anthracene, and Benzo[a]pyrene by Mycobacterium sp. Strain RJGII-135, Isolated from a Former Coal Gasification Site.

    PubMed

    Schneider, J; Grosser, R; Jayasimhulu, K; Xue, W; Warshawsky, D

    1996-04-01

    Volume 62, no. 1, p. 14, column 1, line 20: "250 (mu)g each of yeast extract, peptone, and soluble starch ml(sup-1)" should read "250 (mu)g each of yeast extract, peptone, and soluble starch liter(sup-1)." [This corrects the article on p. 13 in vol. 62.].

  17. Evaluation of the effects of ellagic acid (EA) on 7,12-dimethylbenz(α) anthracene (DMBA) induced micronuclei in mammalian cells in vitro and in vivo.

    PubMed

    Grossi, Maria Rosaria; Berni, Andrea; Pepe, Gaetano; Filippi, Silvia; Meschini, Roberta; Papeschi, Cristiano; Natarajan, Adayapalam T; Palitti, Fabrizio

    2014-01-13

    We evaluated the protective effects of EA, a promising dietary constituent against degenerative diseases, on the clastogenic action of the model carcinogen DMBA in vitro on human hepatoma cells (HepG2) and in vivo on bone marrow of mice, using the frequencies of induced micronuclei as the end poin