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Sample records for benzoylation

  1. Benzoyl Peroxide Topical

    MedlinePlus

    Clear By Design® ... and nose.Do not use benzoyl peroxide on children less than 12 years of age without talking ... in, tightly closed, and out of reach of children. Store it at room temperature and away from ...

  2. Benzoyl peroxide and epidermal wound healing.

    PubMed

    Alvarez, O M; Mertz, P M; Eaglstein, W H

    1983-03-01

    The effectiveness of 10%, 20%, and 50% benzoyl peroxide in a lotion, 20% benzoyl peroxide in a gel, and the effect of the vehicles alone on wound reepithelialization were evaluated in young domestic pigs. Twenty percent benzoyl peroxide suspension in a lotion base substantially increased the rate of reepithelialization by 33% over a seven-day evaluation period. Twenty percent benzoyl peroxide suspension in a gel base and 10% benzoyl peroxide suspension in a lotion base slightly enhanced epidermal resurfacing, while 50% benzoyl peroxide suspension in a lotion base and the vehicle gel retarded healing. Variations in the rate of reepithelialization were observed when different lots of 20% benzoyl peroxide lotions were compared. Chemical analysis of each of the 20% benzoyl peroxide preparations tested disclosed great differences in zinc, magnesium, and sodium content.

  3. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the Food... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2,...

  4. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the Food... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2,...

  5. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the Food... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2,...

  6. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... chloride, sodium hydroxide, and hydrogen peroxide. (b) The ingredient meets the specifications of the Food... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... Specific Substances Affirmed as GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2,...

  7. 21 CFR 184.1157 - Benzoyl peroxide.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... hydrogen peroxide. (b) The ingredient meets the specifications of the Food Chemicals Codex, 3d Ed. (1981... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Benzoyl peroxide. 184.1157 Section 184.1157 Food... GRAS § 184.1157 Benzoyl peroxide. (a) Benzoyl peroxide ((C6H5CO)2O2, CAS Reg. No. 94-36-0) is...

  8. Benzoyl peroxide lotion (20 percent) in acne.

    PubMed

    Smith, E B; Padilla, R S; McCabe, J M; Becker, L E

    1980-01-01

    A double-blind, controlled study was performed to determine the effectiveness of 20 percent benzoyl peroxide lotion in the mangement of mild to moderate acne vulgaris. The results of our study have shown that this new, higher concentration formulation of benzoyl peroxide is effective in reducing the lesions of acne and is relatively nonirritating.

  9. Acne vulgaris: treatment with topical benzoyl peroxide acetone gel.

    PubMed

    Montes, L F

    1977-05-01

    The topical effect on acne of a benzoyl peroxide acetone gel was studied over an eight week period and simultaneously compared with the effect of a benzoyl peroxide lotion and a vitamin A acid cream. The three formulations produced a significant reduction in the number of comedones. The two benzoyl peroxide formulations substantially reduced the number of papules, but this effect was not observed to a significant degree with the vitamin A acid. Burning sensation following application, a common problem with the benzoyl peroxide alcohol gels, was not reported by patients using the benzoyl peroxide acetone gel.

  10. Treatment of pyoderma gangrenosum with benzoyl peroxide.

    PubMed

    Nguyen, L Q; Weiner, J

    1977-06-01

    A fifty-three year old woman presented with pyoderma gangrenosum on the right buttock. She had associated intestinal symptoms, but repeated roentgenologic studies revealed no abnormalities. Local treatment with benzoyl peroxide (20 percent) lotion produced clearing of the cutaneous lesion in about six weeks.

  11. Treatment of cutaneous ulcers with benzoyl peroxide.

    PubMed Central

    Pace, W. E.

    1976-01-01

    Benzoyl peroxide, a powerful organic oxidizing agent, was applied topically according to a carefully developed technique to cutaneous ulcers of different types. The healing time was shortened greatly by the rapid development of healthy granulation tissue and the quick ingrowth of epithelium. Exceptionally large pressure ulcers with deep cavities, undercut edges and sinus tracts were sucessfully treated, as were stasis ulcers of long duration resistant to all other therapy. There were only 13 treatment failures among the 133 cases. The slow, sustained release of oxygen by benzoyl peroxide was though to be responsible for the success. The only complications were contact irritant dermatitis in 3% and contact allergic dermatitis in 2% of patients treated. Images FIG. 2 FIG. 3 FIG. 4 PMID:1000442

  12. A Three-Step Synthesis of Benzoyl Peroxide

    ERIC Educational Resources Information Center

    Her, Brenda; Jones, Alexandra; Wollack, James W.

    2014-01-01

    Benzoyl peroxide is used as a bleaching agent for flour and whey processing, a polymerization initiator in the synthesis of plastics, and the active component of acne medication. Because of its simplicity and wide application, benzoyl peroxide is a target molecule of interest. It can be affordably synthesized in three steps from bromobenzene using…

  13. Topical treatment of acne rosacea with benzoyl peroxide acetone gel.

    PubMed

    Montes, L F; Cordero, A A; Kriner, J; Loder, J; Flanagan, A D

    1983-08-01

    A group of patients with acne rosacea was treated with 5 percent benzoyl peroxide acetone gel for four weeks and then with 10 percent benzoyl peroxide acetone gel for an additional four weeks. A parallel group of patients was treated with a matching placebo (acetone gel vehicle). At the end of the first four weeks of treatment the dropout rate due to lack of improvement was 23 and 63 percent for benzoyl peroxide acetone gel and placebo, respectively. Benzoyl peroxide acetone gel was superior to placebo with respect to improvement in the overall severity of the lesions when judged by photographs, and by reduction of erythema, papules, and pustules. Results after treatment with benzoyl peroxide acetone gel were better during weeks five to eight than during weeks one to four for all lesions except telangiectasia. Benzoyl peroxide acetone gel was superior to placebo when the overall responses were compared. In addition, the benzoyl peroxide acetone gel-treated group, but not the placebo-treated group, showed a significantly better response during weeks five to eight compared to weeks one to four.

  14. Stability of benzoyl peroxide in methyl alcohol.

    PubMed

    Hongo, Toshio; Hikage, Sakari; Sato, Atsushige

    2006-06-01

    The purpose of this study was to clarify the stability of benzoyl peroxide (BPO) in some solvents. BPO was dissolved in acetone, acetonitrile (AcCN), 50% acetonitrile-50% distilled water (50% AcCN), ethyl alcohol (EtOH), and methyl alcohol (MeOH). Solutions containing BPO were incubated for eight days at 25 degrees C. In MeOH, BPO rapidly decomposed into benzoic acid (BA) and methyl benzoate (MeBA) time-dependently, whereas BPO in acetone, AcCN, and 50% AcCN was relatively stable. Although BPO in EtOH was slightly stable within the first 24 hours, it decomposed time-dependently such that BA and EtBA as decomposition products of BPO were produced. These results indicated that the stability of BPO in a solution was dependent on the solvent and the decomposition rate of BPO dissolved in MeOH was the fastest. These suggest that BPO can decompose even in lower-than-activation temperature by the solvent to use for its dissolution.

  15. Treatment with benzoyl peroxide of ulcers on legs within lesions of necrobiosis lipoidica diabeticorum.

    PubMed

    Hanke, C W; Bergfeld, W F

    1978-09-01

    A lotion of 20% benzoyl peroxide was applied to ulcers on legs from necrobiosis lipoidica diabeticorum. The ulcers healed rapidly and uneventfully, leaving firm, yellow scars. The efficacy and simplicity of use of topical benzoyl peroxide therapy is discussed.

  16. Allergic Contact Dermatitis to Benzoyl Peroxide Resembling Impetigo.

    PubMed

    Kim, Changhyun; Craiglow, Brittany G; Watsky, Kalman L; Antaya, Richard J

    2015-01-01

    A 17-year-old boy presented with recurring severe dermatitis of the face of 5-months duration that resembled impetigo. He had been treated with several courses of antibiotics without improvement. Biopsy showed changes consistent with allergic contact dermatitis and patch testing later revealed sensitization to benzoyl peroxide, which the patient had been using for the treatment of acne vulgaris. PMID:25782705

  17. Allergic Contact Dermatitis to Benzoyl Peroxide Resembling Impetigo.

    PubMed

    Kim, Changhyun; Craiglow, Brittany G; Watsky, Kalman L; Antaya, Richard J

    2015-01-01

    A 17-year-old boy presented with recurring severe dermatitis of the face of 5-months duration that resembled impetigo. He had been treated with several courses of antibiotics without improvement. Biopsy showed changes consistent with allergic contact dermatitis and patch testing later revealed sensitization to benzoyl peroxide, which the patient had been using for the treatment of acne vulgaris.

  18. [Benzoyl peroxide for the treatment of leg ulcers (author's transl)].

    PubMed

    Ramelet, A A; van Melle, G

    1980-01-01

    40 leg ulcers were treated for 6 weeks by application twice a day of a 20% benzoyl peroxide lotion. Each ulcer was regularly measured and its bacterial flora was determined. Therapeutic results were very satisfactory: the average healing rate of the ulcers was 62.8% of the initial wound area after 4 weeks of treatment and 76.5% after 6 weeks of treatment. The bacterial flora of the ulcers changed during treatments, streptococci and staphylococci disappeared. Pseudomonas aeruginosa became abundant.

  19. 1-Benzoyl-3-(naphthalen-1-yl)thio­urea

    PubMed Central

    Saeed, Sohail; Rashid, Naghmana; Jasinski, Jerry P; Golen, James A

    2011-01-01

    In the title compound, C18H14N2OS, the dihedral angle between the mean planes of the 3-naphthyl and 1-benzoyl rings is 20.7 (1)°. The crystal packing is stabilized by weak N—H⋯S inter­actions. Intra­molecular N—H⋯O and C—H⋯O hydrogen bonding is also observed. PMID:22199708

  20. The healing of wounds in the skin of piglets treated with benzoyl peroxide.

    PubMed

    Colman, G J; Roenigk, H H

    1978-09-01

    Clinical and microscopic changes in the healing of dermal wounds in the skin of piglets that were treated with a 20% benzoyl peroxide lotion were compared with untreated wounds in the same animal. The wounds treated with benzoyl peroxide showed more rapid healing clinically, and a very pronounced foreign-body giant-cell infiltrate and very vascular granulation tissue microscopically. It may be that benzoyl peroxide promotes wound healing by attracting macrophages and histiocytes into the wound.

  1. The combined use of topical benzoyl peroxide and tretinoin in the treatment of acne vulgaris.

    PubMed

    Handojo, I

    1979-01-01

    A clinical trial using tretinoin lotion 0.05%, benzoyl peroxide 5% and 10% as topical application was performed on 250 ambulatory patients suffering from various degrees of acne vulgaris. The results indicate that tretinoin applied in the morning and benzoyl peroxide applied at night is the most efficacious regimen to be used, with minimal side effects.

  2. Topical therapy of leg ulcers with 20 percent benzoyl peroxide lotion.

    PubMed

    Colman, G J; Roenigk, H H

    1978-04-01

    Preliminary clinical observations suggest that benzoyl peroxide lotion (20%) may be a useful topical treatment for various types of leg ulcers. Further studies utilizing patients as their own controls (treating half of the ulcer surface with 20% benzoyl peroxide) are now underway.

  3. Investigating the Stability of Benzoyl Peroxide in Over-the-Counter Acne Medications

    ERIC Educational Resources Information Center

    Kittredge, Marina Canepa; Kittredge, Kevin W.; Sokol, Melissa S.; Sarquis, Arlyne M.; Sennet, Laura M.

    2008-01-01

    One of the most commonly used ingredients in over-the-counter acne treatments in cream, gel, and wash form is benzoyl peroxide. It is an anti-bacterial agent that kills the bacterium ("Propionibacterium acne") involved in the formation of acne. The formulation of these products is extremely difficult owing to the instability of benzoyl peroxide.…

  4. Factors affecting the morphology of benzoyl peroxide microsponges.

    PubMed

    Nokhodchi, Ali; Jelvehgari, Mitra; Siahi, M Reza; Mozafari, M Reza

    2007-01-01

    Benzoyl peroxide (BPO) is primarily used in the treatment of mild to moderate acne. However, its application is associated with skin irritation. It has been shown that encapsulation and controlled release of BPO could reduce the side effect while also reducing percutaneous absorption when administered to the skin. The aim of the present investigation was to design and formulate an appropriate encapsulated form of BPO, using microsponge technology, and explore the parameters affecting the morphology and other characteristics of the resultant products employing scanning electron microscopy (SEM). Benzoyl peroxide particles were prepared using an emulsion solvent diffusion method by adding an organic internal phase containing benzoyl peroxide, ethyl cellulose and dichloromethane into a stirred aqueous phase containing polyvinyl alcohol (PVA). Different concentrations of BPO microsponges were incorporated in lotion formulations and the drug release from these formulations were studied. The SEM micrographs of the BPO microsponges enabled measurement of their size and showed that they were spherical and porous. Results showed that the morphology and particle size of microsponges were affected by drug:polymer ratio, stirring rate and the amount of emulsifier used. The results obtained also showed that an increase in the ratio of drug:polymer resulted in a reduction in the release rate of BPO from the microsponges. The release data showed that the highest and the lowest release rates were obtained from lotions containing plain BPO particles and BPO microsponges with the drug:polymer ratio of 13:1, respectively. The kinetics of release study showed that the release data followed Peppas model and the main mechanism of drug release from BPO microsponges was diffusion.

  5. Carcinogenesis studies with benzoyl peroxide (Panoxyl gel 5%)

    SciTech Connect

    Iversen, O.H.

    1986-04-01

    Several groups of hairless mice were given UV radiation with and without pretreatment with 7,12-dimethylbenz(a)anthracene (DMBA), 5% benzoyl peroxide in a gel (Panoxyl), and gel alone, in various combinations, with appropriate control groups included, in order to see whether benzoyl peroxide, which is known to enhance chemical skin carcinogenesis after a single, small dose of DMBA, also enhances UV carcinogenesis. The mice were observed for skin tumors, and all skin lesions were histologically investigated. The percentage of tumor-bearing animals with time is called the tumor rate, the total number of tumors occurring is called the tumor yield. Continual treatment with 5% benzoyl peroxide in gel twice a week, with or without a short pretreatment period of UV radiation resulted in only 2 skin carcinomas, which is remarkable, but not significant. Both Panoxyl and gel alone enhanced tumorigenicity significantly in animals pretreated with a single dose of 51.2 micrograms DMBA. There was no difference between the enhancement caused by Panoxyl and the gel as regards the tumor rate, but when measured as final tumor yield, Panoxyl was slightly more tumor-enhancing than gel alone. However, both Panoxyl and gel protected significantly against UV tumorigenesis (all tumors). There was no difference between the protective effect of the 2 types of treatment. Neither Panoxyl nor gel alone influenced significantly UV skin carcinogenesis (malignant tumors). It is concluded that under these experimental conditions both Panoxyl and gel alone tend to protect against the tumorigenicity and do not enhance the carcinogenicity of UV radiation in hairless mice, whereas both gel and Panoxyl enhance chemical carcinogenesis. The carcinogenic mechanisms may be different for UV and chemical carcinogenesis, respectively.

  6. Efficacy and Tolerability of a Three-Step Acne System Containing a Solubilized Benzoyl Peroxide Lotion versus a Benzoyl Peroxide/Clindamycin Combination Product

    PubMed Central

    Del Rosso, James Q.

    2008-01-01

    A brand three-step acne treatment system containing a solubilized 5% benzoyl lotion and a designated cleanser and moisturizer was compared with a brand benzoyl peroxide 5%/clindamycin 1% gel in subjects with acne vulgaris. The single-center, four-week study was investigator-blinded and randomized. The three-step acne treatment system proved to be comparable in efficacy and tolerability. PMID:21203357

  7. Formulation and Characterization of Benzoyl Peroxide Gellified Emulsions

    PubMed Central

    Thakur, Naresh Kumar; Bharti, Pratibha; Mahant, Sheefali; Rao, Rekha

    2012-01-01

    The present investigation was carried out with the objective of formulating a gellified emulsion of benzoyl peroxide, an anti-acne agent. The formulations were prepared using four different vegetable oils, viz. almond oil, jojoba oil, sesame oil, and wheat germ oil, owing to their emollient properties. The idea was to overcome the skin irritation and dryness caused by benzoyl peroxide, making the formulation more tolerable. The gellified emulsions were characterized for their homogeneity, rheology, spreadability, drug content, and stability. In vitro permeation studies were performed to check the drug permeation through rat skin. The formulations were evaluated for their antimicrobial activity, as well as their acute skin irritation potential. The results were compared with those obtained for the marketed formulation. Later, the histopathological examination of the skin treated with various formulations was carried out. Formulation F3 was found to have caused a very mild dysplastic change to the epidermis. On the other hand, the marketed formulation led to the greatest dysplastic change. Hence, it was concluded that formulation F3, containing sesame oil (6%w/w), was the optimized formulation. It exhibited the maximum drug release and anti-microbial activity, in addition to the least skin irritation potential. PMID:23264949

  8. Formulation and characterization of benzoyl peroxide gellified emulsions.

    PubMed

    Thakur, Naresh Kumar; Bharti, Pratibha; Mahant, Sheefali; Rao, Rekha

    2012-12-01

    The present investigation was carried out with the objective of formulating a gellified emulsion of benzoyl peroxide, an anti-acne agent. The formulations were prepared using four different vegetable oils, viz. almond oil, jojoba oil, sesame oil, and wheat germ oil, owing to their emollient properties. The idea was to overcome the skin irritation and dryness caused by benzoyl peroxide, making the formulation more tolerable. The gellified emulsions were characterized for their homogeneity, rheology, spreadability, drug content, and stability. In vitro permeation studies were performed to check the drug permeation through rat skin. The formulations were evaluated for their antimicrobial activity, as well as their acute skin irritation potential. The results were compared with those obtained for the marketed formulation. Later, the histopathological examination of the skin treated with various formulations was carried out. Formulation F3 was found to have caused a very mild dysplastic change to the epidermis. On the other hand, the marketed formulation led to the greatest dysplastic change. Hence, it was concluded that formulation F3, containing sesame oil (6%w/w), was the optimized formulation. It exhibited the maximum drug release and anti-microbial activity, in addition to the least skin irritation potential.

  9. Rapid detection of benzoyl peroxide in wheat flour by using Raman scattering spectroscopy

    NASA Astrophysics Data System (ADS)

    Zhao, Juan; Peng, Yankun; Chao, Kuanglin; Qin, Jianwei; Dhakal, Sagar; Xu, Tianfeng

    2015-05-01

    Benzoyl peroxide is a common flour additive that improves the whiteness of flour and the storage properties of flour products. However, benzoyl peroxide adversely affects the nutritional content of flour, and excess consumption causes nausea, dizziness, other poisoning, and serious liver damage. This study was focus on detection of the benzoyl peroxide added in wheat flour. A Raman scattering spectroscopy system was used to acquire spectral signal from sample data and identify benzoyl peroxide based on Raman spectral peak position. The optical devices consisted of Raman spectrometer and CCD camera, 785 nm laser module, optical fiber, prober, and a translation stage to develop a real-time, nondestructive detection system. Pure flour, pure benzoyl peroxide and different concentrations of benzoyl peroxide mixed with flour were prepared as three sets samples to measure the Raman spectrum. These samples were placed in the same type of petri dish to maintain a fixed distance between the Raman CCD and petri dish during spectral collection. The mixed samples were worked by pretreatment of homogenization and collected multiple sets of data of each mixture. The exposure time of this experiment was set at 0.5s. The Savitzky Golay (S-G) algorithm and polynomial curve-fitting method was applied to remove the fluorescence background from the Raman spectrum. The Raman spectral peaks at 619 cm-1, 848 cm-1, 890 cm-1, 1001 cm-1, 1234 cm-1, 1603cm-1, 1777cm-1 were identified as the Raman fingerprint of benzoyl peroxide. Based on the relationship between the Raman intensity of the most prominent peak at around 1001 cm-1 and log values of benzoyl peroxide concentrations, the chemical concentration prediction model was developed. This research demonstrated that Raman detection system could effectively and rapidly identify benzoyl peroxide adulteration in wheat flour. The experimental result is promising and the system with further modification can be applicable for more products in near

  10. Benzoyl peroxide interferes with metabolic co-operation between cultured human epidermal keratinocytes

    SciTech Connect

    Lawrence, N.J.; Parkinson, E.K.; Emmerson, A.

    1984-03-01

    The ability of benzoyl peroxide to inhibit metabolic co-operation in rodent cell cultures may be relevant to its recently reported tumour promoting activity in mouse epidermis. We show here that non-toxic doses of this compound reduce metabolic co-operation between human epidermal keratinocytes to approximately 30% of that found in controls. The doses of benzoyl peroxide used did not affect keratinocyte morphology or their rate of attachment to the culture substratum. These results could be important as benzoyl peroxide is widely used in industry.

  11. Regioselective Benzoylation of Diols and Carbohydrates by Catalytic Amounts of Organobase.

    PubMed

    Lu, Yuchao; Hou, Chenxi; Ren, Jingli; Xin, Xiaoting; Xu, Hengfu; Pei, Yuxin; Dong, Hai; Pei, Zhichao

    2016-01-01

    A novel metal-free organobase-catalyzed regioselective benzoylation of diols and carbohydrates has been developed. Treatment of diol and carbohydrate substrates with 1.1 equiv. of 1-benzoylimidazole and 0.2 equiv. of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in MeCN under mild conditions resulted in highly regioselective benzoylation for the primary hydroxyl group. Importantly, compared to most commonly used protecting bulky groups for primary hydroxyl groups, the benzoyl protective group offers a new protection strategy. PMID:27196888

  12. A comparative study of isolutrol versus benzoyl peroxide in the treatment of acne.

    PubMed

    Dunlop, K J; Barnetson, R S

    1995-02-01

    Isolutrol is the active principle isolated from aqueous tissue extracts of deep sea shark liver and gall-bladder. A previous study has demonstrated the ability of isolutrol to reduce hyperseborrhoea, which provides a rationale for its use in the treatment of acne. We have performed a double-blind clinical trial on 70 patients to evaluate the efficacy and skin tolerance of isolutrol 0.15 g/100 mL (Ketsugo) in the treatment of mild to moderate acne when compared with 5% benzoyl peroxide lotion. The results from this study showed that both isolutrol and benzoyl peroxide significantly improved patients' acne by reducing the number of inflamed lesions. Isolutrol did not significantly reduce the numbers of non-inflamed lesions whereas benzoyl peroxide did. Fewer side effects were experienced by patients treated with isolutrol when compared with benzoyl peroxide. These results indicate that isolutrol may be a useful adjunct in the treatment of acne, particularly in patients with inflamed lesions.

  13. Photoaffinity labeling of myosin subfragment-one-with 3'(2')-O-(4-benzoyl)benzoyl adenosine 5'-triphosphate

    SciTech Connect

    Mahmood, R.

    1985-01-01

    The photoaffinity analogue 3'(2')-O-(4-benzoyl)benzoyl adenosine 5'-triphosphate (Bz/sub 2/ATP) contains the photoreactive benzophenone group esterified at the 2' or 3' hydroxyl groups of ribose. MgBz/sub 2/ADP has a single binding site on skeletal myosin chymotryptic subfragment-one (SF/sub 1/) with a binding constant of 3.2 x 10/sup 5/ M/sup -1/. Bz/sub 2/ATP is also a substrate for the ATPase activity of SF/sub 1/ in the presence of different cations. The irradiation of SF/sub 1/ with (/sup 3/H)Bz/sub 2/ATP photoinactivates the ATPase activity with concomitant incorporation of the analogue into the enzyme. Polyacrylamide gel electrophoresis of photolabeled SF/sub 1/ after milk trypsin digestion shows that all three tryptic peptides, 25 K, 50K, and 20 K, and both light chains are labeled. The presence of ATP during irradiation reduces labeling of the 50 K peptide only indicating that the other peptides are non-specifically labeled. To reduce the non-specific labeling (/sup 3/H)Bz/sub 2/ATP is trapped on SF/sub 1/ by cross-linking the two reactive thiols, SH/sub 1/ and SH/sub 2/, by N,N'-p-phenylene dimaleimide or Co(II)/Co(III) phenanthroline complexes. The Co(II)/Co(III) phenanthroline modified (/sup 14/C)Bz/sub 2/ATP-SF/sub 1/, after proteolytic digestion, yields five labeled peptides which were purified by gel filtration and high performance liquid chromatography.

  14. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae.

    PubMed

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; Baidoo, Edward E K; Lee, Taek Soon; Keasling, Jay D; Loqué, Dominique

    2015-01-01

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. This work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.

  15. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

    SciTech Connect

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; Baidoo, Edward E. K.; Lee, Taek Soon; Keasling, Jay D.; Loqué, Dominique

    2015-10-02

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. Finally, this work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.

  16. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

    PubMed Central

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; Baidoo, Edward E. K.; Lee, Taek Soon; Keasling, Jay D.; Loqué, Dominique

    2015-01-01

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilates by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. This work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases. PMID:26430899

  17. Benzoyl peroxide: percutaneous penetration and metabolic disposition. II. Effect of concentration.

    PubMed

    Yeung, D; Nacht, S; Bucks, D; Maibach, H I

    1983-12-01

    The effect of drug concentrations of 2.5%, 5%, and 10% upon the transepidermal penetration of 14C-benzoyl peroxide in a lotion vehicle was assessed in excised human skin and in vivo in the rhesus monkey. In vitro, penetration of benzoyl peroxide was concentration-dependent, both as to rate and to amount, as measured by the hourly recovery of the metabolite, benzoic acid, from the dermal side of the model. In vivo, the higher the concentration of benzoyl peroxide applied, the greater the amount absorbed, as indicated by the urinary excretion of 14C-benzoic acid. Metabolic disposition of benzoyl peroxide, in turn, was unaffected by drug concentration. In all instances, the benzoyl peroxide absorbed was excreted rapidly in urine as benzoic acid; no hippuric acid was detected at any time. We conclude that (1) use of the excised human skin model for this compound can provide useful data in studies of the effects of vehicle and concentration on topical drug delivery, (2) the transepidermal delivery of benzoyl peroxide, but not its metabolic disposition, is concentration-dependent, and (3) the renal clearance of the systemically absorbed drug is so rapid that it precludes passage through the liver--therefore, no systemic toxicity due to drug accumulation can be expected.

  18. Precursor-Directed Combinatorial Biosynthesis of Cinnamoyl, Dihydrocinnamoyl, and Benzoyl Anthranilates in Saccharomyces cerevisiae

    DOE PAGESBeta

    Eudes, Aymerick; Teixeira Benites, Veronica; Wang, George; Baidoo, Edward E. K.; Lee, Taek Soon; Keasling, Jay D.; Loqué, Dominique

    2015-10-02

    Biological synthesis of pharmaceuticals and biochemicals offers an environmentally friendly alternative to conventional chemical synthesis. These alternative methods require the design of metabolic pathways and the identification of enzymes exhibiting adequate activities. Cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates are natural metabolites which possess beneficial activities for human health, and the search is expanding for novel derivatives that might have enhanced biological activity. For example, biosynthesis in Dianthus caryophyllus is catalyzed by hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/ benzoyltransferase (HCBT), which couples hydroxycinnamoyl-CoAs and benzoyl-CoAs to anthranilate. We recently demonstrated the potential of using yeast (Saccharomyces cerevisiae) for the biological production of a few cinnamoyl anthranilatesmore » by heterologous co-expression of 4-coumaroyl:CoA ligase from Arabidopsis thaliana (4CL5) and HCBT. Here we report that, by exploiting the substrate flexibility of both 4CL5 and HCBT, we achieved rapid biosynthesis of more than 160 cinnamoyl, dihydrocinnamoyl, and benzoyl anthranilates in yeast upon feeding with both natural and non-natural cinnamates, dihydrocinnamates, benzoates, and anthranilates. Our results demonstrate the use of enzyme promiscuity in biological synthesis to achieve high chemical diversity within a defined class of molecules. Finally, this work also points to the potential for the combinatorial biosynthesis of diverse and valuable cinnamoylated, dihydrocinnamoylated, and benzoylated products by using the versatile biological enzyme 4CL5 along with characterized cinnamoyl-CoA- and benzoyl-CoA-utilizing transferases.« less

  19. Model studies on the oxidation of benzoyl methionine in a carbohydrate degradation system.

    PubMed

    Hellwig, Michael; Löbmann, Katja; Orywol, Tom; Voigt, Annegrit

    2014-05-14

    The stability of benzoyl methionine was analyzed during incubation with carbohydrate compounds such as reducing sugars, dicarbonyl compounds, reductones, and Amadori rearrangement products (ARPs). The reaction products were identified and quantified by HPLC-UV and HPLC-MS. In the presence of ARPs, >40% of benzoyl methionine was oxidized to benzoyl methionine sulfoxide after 48 h at 80 °C in acetate-buffered solution (pH 6.0), whereas <10% was oxidized in the presence of mono- and disaccharides. As an important side reaction, peptide bond cleavage through α-amidation was verified. The influence of benzoyl methionine on carbohydrate degradation reactions was assessed through analysis of vicinal dicarbonyl compounds by HPLC-UV. Glyoxal, methylglyoxal, diacetyl, and 3-deoxyglucosone were quantified as the most important derivatives. The thioether group of methionine strongly influenced carbohydrate degradation pathways: Less glyoxal was formed from reducing carbohydrates, showing that benzoyl methionine can act as a radical scavenger. However, more diacetyl was formed from ARPs and reductones, indicating that also radical-dependent pathways could be influenced by benzoyl methionine. The degradation of reducing carbohydrates should thus be an important contributor to protein oxidation in food items with low fat content.

  20. [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid].

    PubMed

    Worret, Wolf-Ingo; Fluhr, Joachim W

    2006-04-01

    Benzoyl peroxide (BPO) was introduced in the treatment of acne in 1934. Despite the fact that only few randomized trials have been published, BPO is considered the standard in topical acne treatment. Anaerobic bacteria are reduced by oxidative mechanisms and the induction of resistant strains is reduced. Topical formulations are available at concentrations of 2.5, 5, 10 and 20 %. The effect is dose-dependent, but the irritation increases with higher concentrations. Usually 5 % BPO is sufficient to control acne grade I-II. Due to its strong oxidative potential, patients should be advised that BPO may bleach colored and dark clothing, bedding and even hair. BPO is safe for use in pregnant and lactating females because it is degraded to benzoic acid. It is a cost-effective treatment for acne grade I-II. Patients with papulopustular acne grade I-II, particularly with marked inflammation, show satisfactory improvement with topical antibiotic treatment. The following compounds are available and effective: erythromycin, clindamycin and tetracycline (the latter being less frequently used). A review in 1990 suggested that topical tetracycline was ineffective in the treatment of acne. Along with eliminating Propionibacterium acnes, the main mechanism of topical antibiotics is their antiinflammatory effect. All three penetrate the epidermal barrier well and are similarly efficacious. Randomized trials have shown that in concentrations of 2-4 %, their effects are comparable to oral tetracycline and minocycline. Combination therapy with retinoids or benzoyl peroxide (BPO) increases efficacy. Retinoids increase penetration and reduce comedones, while topical antibiotics primarily address inflammation. One side effect of topical antibacterial treatment is an increase in drug-resistant resident skin flora with gram-negative microorganisms prevailing, which can lead to gram-negative folliculitis. All three antibiotics fluoresce under black light which may produce interesting

  1. [Acne therapy with topical benzoyl peroxide, antibiotics and azelaic acid].

    PubMed

    Worret, Wolf-Ingo; Fluhr, Joachim W

    2006-04-01

    Benzoyl peroxide (BPO) was introduced in the treatment of acne in 1934. Despite the fact that only few randomized trials have been published, BPO is considered the standard in topical acne treatment. Anaerobic bacteria are reduced by oxidative mechanisms and the induction of resistant strains is reduced. Topical formulations are available at concentrations of 2.5, 5, 10 and 20 %. The effect is dose-dependent, but the irritation increases with higher concentrations. Usually 5 % BPO is sufficient to control acne grade I-II. Due to its strong oxidative potential, patients should be advised that BPO may bleach colored and dark clothing, bedding and even hair. BPO is safe for use in pregnant and lactating females because it is degraded to benzoic acid. It is a cost-effective treatment for acne grade I-II. Patients with papulopustular acne grade I-II, particularly with marked inflammation, show satisfactory improvement with topical antibiotic treatment. The following compounds are available and effective: erythromycin, clindamycin and tetracycline (the latter being less frequently used). A review in 1990 suggested that topical tetracycline was ineffective in the treatment of acne. Along with eliminating Propionibacterium acnes, the main mechanism of topical antibiotics is their antiinflammatory effect. All three penetrate the epidermal barrier well and are similarly efficacious. Randomized trials have shown that in concentrations of 2-4 %, their effects are comparable to oral tetracycline and minocycline. Combination therapy with retinoids or benzoyl peroxide (BPO) increases efficacy. Retinoids increase penetration and reduce comedones, while topical antibiotics primarily address inflammation. One side effect of topical antibacterial treatment is an increase in drug-resistant resident skin flora with gram-negative microorganisms prevailing, which can lead to gram-negative folliculitis. All three antibiotics fluoresce under black light which may produce interesting

  2. [Antibiotics, azelaic acid and benzoyl peroxide in topical acne therapy].

    PubMed

    Fluhr, Joachim W; Degitz, Klaus

    2010-03-01

    Benzoyl peroxide was introduced as a basic treatment already in acne therapy 1934. The mechanism of action is the reduction of anaerobe bacteria by strong oxidation processes. No resistancies have been ever reported. BPO is available in 2.5, 5 and 10 % formulations. Its efficacy is slightly related to the strength of concentrations, but the side effect profile with burning, erythema and desquamation is increasing with concentrations. BPO 5% mostly is efficient enough to control acne of grades I to II according to the Kligman & Plewig classification. BPO my bleach clothes and hair. It is the most costeffective topical drug in acne of grades I-II. Inflammatory acne of the papular-pustular type I-II can also be treated by topical antibiotics such as erythromycin, clindamycin, and, less frequent and today not anymore recommended tetracyclines. Mechanism of action is not alone an antibacterial but anti inflammatory effect. The efficacy and penetration of the topical antibiotics between the groups are similar. Randomized studies have shown that concentrations of 2-4% are equivalent to oral tetracycline and minocycline in mild to moderate acne. Combinatory formulations with BPO and with retinoids enhance the efficacy significantly. Topical antibiotics plus BPO show less bacterial resistancies as topical antibiotics alone. Antibiotics should therefore not be used as monotherapy. Moreover gram negative folliculitis may develop. Azelaic acid is acting as an antimicrobial and can also reduce comedones. It can also be used in pregnancy and during the lactation period.

  3. [Antibiotics, azelaic acid and benzoyl peroxide in topical acne therapy].

    PubMed

    Fluhr, Joachim W; Degitz, Klaus

    2010-03-01

    Benzoyl peroxide was introduced as a basic treatment already in acne therapy 1934. The mechanism of action is the reduction of anaerobe bacteria by strong oxidation processes. No resistancies have been ever reported. BPO is available in 2.5, 5 and 10 % formulations. Its efficacy is slightly related to the strength of concentrations, but the side effect profile with burning, erythema and desquamation is increasing with concentrations. BPO 5% mostly is efficient enough to control acne of grades I to II according to the Kligman & Plewig classification. BPO my bleach clothes and hair. It is the most costeffective topical drug in acne of grades I-II. Inflammatory acne of the papular-pustular type I-II can also be treated by topical antibiotics such as erythromycin, clindamycin, and, less frequent and today not anymore recommended tetracyclines. Mechanism of action is not alone an antibacterial but anti inflammatory effect. The efficacy and penetration of the topical antibiotics between the groups are similar. Randomized studies have shown that concentrations of 2-4% are equivalent to oral tetracycline and minocycline in mild to moderate acne. Combinatory formulations with BPO and with retinoids enhance the efficacy significantly. Topical antibiotics plus BPO show less bacterial resistancies as topical antibiotics alone. Antibiotics should therefore not be used as monotherapy. Moreover gram negative folliculitis may develop. Azelaic acid is acting as an antimicrobial and can also reduce comedones. It can also be used in pregnancy and during the lactation period. PMID:20482689

  4. Controlled release of benzoyl peroxide from a porous microsphere polymeric system can reduce topical irritancy.

    PubMed

    Wester, R C; Patel, R; Nacht, S; Leyden, J; Melendres, J; Maibach, H

    1991-05-01

    Skin absorption of benzoyl peroxide from a topical lotion containing freely dispersed drug was compared with that from the same lotion in which the drug was entrapped in a controlled-release styrene-divinylbenzene polymer system. In an in vitro diffusion system, statistically significant (p = 0.01) differences were found in the content of benzoyl peroxide in excised human skin and in percutaneous absorption. In vivo, significantly (p = 0.002) less benzoyl peroxide was absorbed through rhesus monkey skin from the polymeric system. This controlled release of benzoyl peroxide to skin can alter the dose relation that exists between efficacy and skin irritation. Corresponding studies showed reduced skin irritation in cumulative irritancy studies in rabbits and human beings, whereas in vivo human antimicrobial efficacy studies showed that application of the formulations containing entrapped benzoyl peroxide significantly reduced counts of Propionibacterium acnes (p less than 0.001) and aerobic bacteria (p less than 0.001) and the free fatty acid/triglyceride ratio in skin lipids. These findings support the hypothesis that, at least for this drug, controlled topical delivery can enhance safety without sacrificing efficacy.

  5. The promotion of wound healing following chemosurgery (Mohs' technique) by dressings with a lotion of benzoyl peroxide.

    PubMed

    Lynch, W S; Bailin, P L

    1978-01-01

    A lotion of benzoyl peroxide was applied postoperatively to chemosurgical wounds in a small group of patients. The technique of utilizing dressings of benzoyl peroxide is described and illustrated. Enhanced wound healing was observed in all cases. The effects appear to be due, at least in part, to antimicrobial activity, debriding activity, hyperbaric oxygenation, and stimulation of granulation.

  6. A facile BPO-mediated ortho-hydroxylation and benzoylation of N-alkyl anilines for synthesis of 2-benzamidophenols.

    PubMed

    Zhang, Zhi-Jing; Quan, Xue-Jing; Ren, Zhi-Hui; Wang, Yao-Yu; Guan, Zheng-Hui

    2014-06-20

    A facile benzoyl peroxide (BPO) mediated ortho-hydroxylation and benzoylation of N-alkyl anilines for the synthesis of 2-benzamidophenols has been developed. The reaction tolerates a wide range of functional groups and is a good method for the straightforward synthesis of valuable 2-benzamidophenols in good yields under mild conditions.

  7. Comparative activity of benzoyl peroxide and hexachlorophene. In vivo studies against propionibacterium acnes in humans.

    PubMed

    Nacht, S; Gans, E H; McGinley, K J; Kligman, A M

    1983-07-01

    The bactericidal effects of benzoyl peroxide (5% lotion) and hexachlorophene (3% colloidal suspension) against Propionibacterium acnes were compared in nine healthy college students who had the microbiological and skin lipid characteristics typical of acne vulgaris, but no active lesions. Each of the two medications was applied twice daily, to opposite sides of the face, for four consecutive weeks. Hexachlorophene was effective against surface aerobes but only slightly active against P acnes. It marginally reduced free fatty acid concentrations in surface lipids and in follicular porphyrin fluorescence. Conversely, benzoyl peroxide virtually eliminated P acnes and aerobes and induced substantially decreased free fatty acid concentrations and follicular fluorescence. We conclude that benzoyl peroxide exerts its antimicrobial action in the follicles and inhibits P acnes, while the antimicrobial effectiveness of hexachlorophene is limited to the skin surface.

  8. A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne.

    PubMed

    Hunt, M J; Barnetson, R S

    1992-01-01

    Alpha hydroxy acids (AHA's) or "fruit acids" are a special group of organic acids found in many natural foods. They have been described in the literature for the treatment of a number of conditions in which abnormal keratinization consistently contributes to pathogenesis. These include the icthyoses, warts, psoriasis, eczema and acne. We have performed a double-blind clinical trial on 150 patients to evaluate the efficacy and skin tolerance of the alpha hydroxy acid gluconolactone 14% in solution (Nuvoderm lotion) in the treatment of mild to moderate acne when compared with its vehicle (placebo) and 5% benzoyl peroxide lotion. The results of this study showed that both gluconolactone and benzoyl peroxide had a significant effect in improving patients' acne by reducing the number of lesions (inflamed and non-inflamed). Furthermore, fewer side-effects were experienced by patients treated with gluconolactone when compared with benzoyl peroxide.

  9. Vibrational overtone enhancement of methyl methacrylate polymerization initiated by benzoyl peroxide decomposition

    NASA Astrophysics Data System (ADS)

    Grinevich, Oleg; Snavely, D. L.

    1997-03-01

    Vibrational overtone initiated polymerization has been demonstrated using intracavity photolysis of a benzoyl peroxide/methyl methacrylate mixture. Excitation of the 6 νCH overtone transition of the ground electronic state of benzoyl peroxide creates radicals which subsequently begin the polymerization process. Polymer yield was monitored by comparison of the 2 νCH overtone absorptions for the methyl, methylenic and olefinic CH stretches at 5946 and 6170 cm -1, respectively. Plots of polymer yield versus time demonstrate an autoacceleration of the polymerization rate commencing many hours after the photolysis period. The delay before autoacceleration depends on the duration of the photolysis.

  10. Benzoyl peroxide versus topical erythromycin in the treatment of acne vulgaris.

    PubMed

    Burke, B; Eady, E A; Cunliffe, W J

    1983-02-01

    In a double-blind clinical study in ninety-four subjects a 1.5% (w/v) erythromycin lotion was as effective as 5% (w/v) benzoyl peroxide gel in significantly reducing the number of small inflamed lesions and the overall acne severity. However, benzoyl peroxide also significantly reduced the number of non-inflamed lesions whereas erythromycin had no effect on these lesions. This study supports the view that, although topical erythromycin is of value in the treatment of mild or moderate acne vulgaris, long established, safe and effective remedies should not be replaced by topical antibiotics until more comparative studies and investigations on bacterial resistance have been completed.

  11. 1-Benzoyl-4-(4-methyl­phen­yl)phthal­azine

    PubMed Central

    Sakthivel, Karuppusamy; Srinivasan, Kannupal; Natarajan, Sampath

    2011-01-01

    In the title mol­ecule, C22H16N2O, the tolyl and benzoyl rings make dihedral angles 50.2 (5) and 56.4 (5)°, respectively, with the phthalazine ring system while the dihedral angle between the tolyl and benzoyl rings is 0.70 (4)°. The crystal structure is stabilized by inter­molecular C—H⋯O and C—H⋯N hydrogen bonds, as well as weak C—H⋯π inter­actions. PMID:22199969

  12. Novel N-Benzoyl-2-Hydroxybenzamide Disrupts Unique Parasite Secretory Pathway

    PubMed Central

    Fomovska, Alina; Huang, Qingqing; El Bissati, Kamal; Mui, Ernest J.; Witola, William H.; Cheng, Gang; Zhou, Ying; Sommerville, Caroline; Roberts, Craig W.; Bettis, Sam; Prigge, Sean T.; Afanador, Gustavo A.; Hickman, Mark R.; Lee, Patty J.; Leed, Susan E.; Auschwitz, Jennifer M.; Pieroni, Marco; Stec, Jozef; Muench, Stephen P.; Rice, David W.; Kozikowski, Alan P.

    2012-01-01

    Toxoplasma gondii is a protozoan parasite that can damage the human brain and eyes. There are no curative medicines. Herein, we describe our discovery of N-benzoyl-2-hydroxybenzamides as a class of compounds effective in the low nanomolar range against T. gondii in vitro and in vivo. Our lead compound, QQ-437, displays robust activity against the parasite and could be useful as a new scaffold for development of novel and improved inhibitors of T. gondii. Our genome-wide investigations reveal a specific mechanism of resistance to N-benzoyl-2-hydroxybenzamides mediated by adaptin-3β, a large protein from the secretory protein complex. N-Benzoyl-2-hydroxybenzamide-resistant clones have alterations of their secretory pathway, which traffics proteins to micronemes, rhoptries, dense granules, and acidocalcisomes/plant-like vacuole (PLVs). N-Benzoyl-2-hydroxybenzamide treatment also alters micronemes, rhoptries, the contents of dense granules, and, most markedly, acidocalcisomes/PLVs. Furthermore, QQ-437 is active against chloroquine-resistant Plasmodium falciparum. Our studies reveal a novel class of compounds that disrupts a unique secretory pathway of T. gondii, with the potential to be used as scaffolds in the search for improved compounds to treat the devastating diseases caused by apicomplexan parasites. PMID:22354304

  13. Novel N-benzoyl-2-hydroxybenzamide disrupts unique parasite secretory pathway.

    PubMed

    Fomovska, Alina; Huang, Qingqing; El Bissati, Kamal; Mui, Ernest J; Witola, William H; Cheng, Gang; Zhou, Ying; Sommerville, Caroline; Roberts, Craig W; Bettis, Sam; Prigge, Sean T; Afanador, Gustavo A; Hickman, Mark R; Lee, Patty J; Leed, Susan E; Auschwitz, Jennifer M; Pieroni, Marco; Stec, Jozef; Muench, Stephen P; Rice, David W; Kozikowski, Alan P; McLeod, Rima

    2012-05-01

    Toxoplasma gondii is a protozoan parasite that can damage the human brain and eyes. There are no curative medicines. Herein, we describe our discovery of N-benzoyl-2-hydroxybenzamides as a class of compounds effective in the low nanomolar range against T. gondii in vitro and in vivo. Our lead compound, QQ-437, displays robust activity against the parasite and could be useful as a new scaffold for development of novel and improved inhibitors of T. gondii. Our genome-wide investigations reveal a specific mechanism of resistance to N-benzoyl-2-hydroxybenzamides mediated by adaptin-3β, a large protein from the secretory protein complex. N-Benzoyl-2-hydroxybenzamide-resistant clones have alterations of their secretory pathway, which traffics proteins to micronemes, rhoptries, dense granules, and acidocalcisomes/plant-like vacuole (PLVs). N-Benzoyl-2-hydroxybenzamide treatment also alters micronemes, rhoptries, the contents of dense granules, and, most markedly, acidocalcisomes/PLVs. Furthermore, QQ-437 is active against chloroquine-resistant Plasmodium falciparum. Our studies reveal a novel class of compounds that disrupts a unique secretory pathway of T. gondii, with the potential to be used as scaffolds in the search for improved compounds to treat the devastating diseases caused by apicomplexan parasites.

  14. Benzoyl peroxide (BPO)-promoted oxidative trifluoromethylation of tertiary amines with trimethyl(trifluoromethyl)silane.

    PubMed

    Chu, Lingling; Qing, Feng-Ling

    2010-09-14

    The benzoyl peroxide (BPO)-promoted oxidative functionalization of tertiary amines under transition-metal-free reaction conditions was developed. Various 1-trifluoromethylated tetrahydroisoquinoline derivatives were prepared by employing this method. It constitutes the first example of direct trifluoromethylation of tertiary amines.

  15. Benzoyl peroxide, adapalene, and their combination in the treatment of acne vulgaris.

    PubMed

    Korkut, Caner; Piskin, Suleyman

    2005-03-01

    Benzoyl peroxide and adapalene are among the most effective topical agents used in the treatment of acne. We planned an open-labeled, prospective study to compare the effects and side effects of these two drugs alone and in combination in the treatment of acne vulgaris. One hundred and five consecutive patients (30 men and 75 women) with acne vulgaris were included in this study. The patients were randomly divided into three groups with 35 patients in each. The groups were randomly assigned to 0.1% adapalene gel, 5% benzoyl peroxide lotion, or combination of 0.1% adapalene gel +5% benzoyl peroxide treatment. Acne lesions were classified as noninflammatory (open and closed comedones) and inflammatory (papule, pustule, nodule, cyst), and the lesions on the face were counted before the therapy, during the control visits, and after the treatment. Erythema, dryness, burning, and other side effects were recorded during the treatment. The mean age of the patients was 18.44 +/- 3.75 years. Eight patients were excluded because of noncompliance with the treatment regimen or the follow-up schedule, and four patients were excluded due to allergic contact dermatitis. The study revealed that all three therapy protocols were effective in treating noninflammatory and inflammatory lesions in acne vulgaris (p<0.05) and that there was no significant difference between the groups in efficacy or side effects (p>0.05). Adapalene and benzoyl peroxide are effective and well tolerated agents for acne vulgaris; combination therapy has no superiority over adapalene or benzoyl peroxide alone.

  16. Enzymes of the benzoyl-coenzyme A degradation pathway in the hyperthermophilic archaeon Ferroglobus placidus.

    PubMed

    Schmid, Georg; René, Sandra Bosch; Boll, Matthias

    2015-09-01

    The Fe(III)-respiring Ferroglobus placidus is the only known archaeon and hyperthermophile for which a complete degradation of aromatic substrates to CO2 has been reported. Recent genome and transcriptome analyses proposed a benzoyl-coenzyme A (CoA) degradation pathway similar to that found in the phototrophic Rhodopseudomonas palustris, which involves a cyclohex-1-ene-1-carboxyl-CoA (1-enoyl-CoA) forming, ATP-dependent key enzyme benzoyl-CoA reductase (BCR). In this work, we demonstrate, by first in vitro studies, that benzoyl-CoA is ATP-dependently reduced by two electrons to cyclohexa-1,5-dienoyl-CoA (1,5-dienoyl-CoA), which is further degraded by hydration to 6-hydroxycyclohex-1-ene-1-carboxyl-CoA (6-OH-1-enoyl-CoA); upon addition of NAD(+) , the latter was subsequently converted to β-oxidation intermediates. The four candidate genes of BCR were heterologously expressed, and the enriched, oxygen-sensitive enzyme catalysed the two-electron reduction of benzoyl-CoA to 1,5-dienoyl-CoA. A gene previously assigned to a 2,3-didehydropimeloyl-CoA hydratase was heterologously expressed and shown to act as a typical 1,5-dienoyl-CoA hydratase that does not accept 1-enoyl-CoA. A gene previously assigned to a 1-enoyl-CoA hydratase was heterologously expressed and identified to code for a bifunctional crotonase/3-OH-butyryl-CoA dehydrogenase. In summary, the results consistently provide biochemical evidence that F. placidus and probably other archaea predominantly degrade aromatics via the Thauera/Azoarcus type and not or only to a minor extent via the predicted R. palustris-type benzoyl-CoA degradation pathway.

  17. Efficacy and Tolerability of a Three-Step Acne System Containing a Solubilized Benzoyl Peroxide Lotion versus a Benzoyl Peroxide/Clindamycin Combination Product: An Investigator-Blind, Randomized, Parallel-Group Study.

    PubMed

    Green, Lawrence J; Del Rosso, James Q

    2008-09-01

    A brand three-step acne treatment system containing a solubilized 5% benzoyl lotion and a designated cleanser and moisturizer was compared with a brand benzoyl peroxide 5%/clindamycin 1% gel in subjects with acne vulgaris. The single-center, four-week study was investigator-blinded and randomized. The three-step acne treatment system proved to be comparable in efficacy and tolerability.

  18. Enhancing intermolecular benzoyl-transfer reactivity in crystals by growing a "reactive" metastable polymorph by using a chiral additive.

    PubMed

    Murali, Chebrolu; Shashidhar, Mysore S; Gonnade, Rajesh G; Bhadbhade, Mohan M

    2009-01-01

    Racemic 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoacetate, which normally crystallizes in a monoclinic form (form I, space group P2(1)/n) could be persuaded to crystallize out as a metastable polymorph (form II, space group C2/c) by using a small amount of either D- or L- 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoformate as an additive in the crystallization medium. The structurally similar enantiomeric additive was chosen by the scrutiny of previous experimental results on the crystallization of racemic 2,4-di-O-benzoyl-myo-inositol-1,3,5-orthoacetate. Form II crystals can be thermally transformed to form I crystals at about 145 degrees C. The relative organization of the molecules in these dimorphs vary slightly in terms of the helical assembly of molecules, that is, electrophile (El)...nucleophile (Nu) and C-H...pi interactions, but these minor variations have a profound effect on the facility and specificity of benzoyl-group-transfer reactivity in the two crystal forms. While form II crystals undergo a clean intermolecular benzoyl-group-transfer reaction, form I crystals are less reactive and undergo non-specific benzoyl-group transfer leading to a mixture of products. The role played by the additive in fine-tuning small changes that are required in the molecular packing opens up the possibility of creating new polymorphs that show varied physical and chemical properties. Crystals of D-2,6-di-O-benzoyl-myo-inositol-1,3,5-orthoformate (additive) did not show facile benzoyl-group-transfer reactivity (in contrast to the corresponding racemic compound) due to the lack of proper juxtaposition and assembly of molecules.

  19. Intense pulsed light versus benzoyl peroxide 5% gel in treatment of acne vulgaris.

    PubMed

    El-Latif, Azmy Ahmed Abd; Hassan, Faisal Abdel Aziz; Elshahed, Ahmed Rashad; Mohamed, Amr Ghareeb; Elsaie, Mohamed L

    2014-05-01

    Acne is a common disorder affecting the pilosebaceous unit. Despite many advances in the treatments of acne vulgaris the best option is still controversial as the pathogenesis of acne is rather complex, necessitating various combination therapies. The objective of this study is to compare the clinical efficacy of intense pulsed light therapy (IPL) versus benzoyl peroxide 5% for the treatment of inflammatory acne. Fifty patients of both sexes, (15 males and 35 females) aged (18-27 years), with mild-to-severe acne and Fitzpatrick skin phototype IV were enrolled in this study. The patients were equally divided into two groups. The first group was treated by benzoyl peroxide while the second group was treated by IPL. For both therapies, patients experienced a significant reduction in the mean of the inflammatory lesion counts over the treatment period. Comparing the effects of both therapies, BP produced better results than IPL. The difference in the results was statistically significant at the midpoint of the study. However, this difference was insignificant at the end of study. Treatment with both benzoyl peroxide and IPL resulted in considerable improvement of the acne after 5 weeks of treatment. Comparing the effects of both therapies, BP produced better results than IPL. The difference in the results was statistically significant at the midpoint of the study. However, this difference was insignificant at the end of study.

  20. Analysis of benzoyl-peroxide and formaldehyde as dental allergens by FT-SPR method

    NASA Astrophysics Data System (ADS)

    Bako, J.; Kelemen, M.; Hegedus, Cs

    2013-12-01

    In parallel with the appearance of new dental materials the number of induced allergic diseases increases. Based on this fact more sensitive detection of allergens is major importance. The Fourier-Transform Surface Plasmon Resonance (FT-SPR) is a sensitive, broadly applicable real-time method for analysing thin layers of materials on gold surfaces. FT-SPR measurement is performed at a fixed angel of incident light, and reflectivity is measured over a range of wavelength in the near infrared. In our study the formaldehyde and benzoyl-peroxide were examined as members of the most common dental allergens by FT-SPR spectroscopy. The aim of this work was the investigation of the suitability of this method for the direct detection of these materials. Different concentrations of formaldehyde and benzoyl-peroxide solutions were measured from this purpose. The individual spectra were measured for all of the solutions, and calibration curves were calculated for the materials for the possibility of the determination of an unknown concentration. In addition, series measurements were performed whereby the association and dissociation properties of formaldehyde or benzoyl-peroxide were described. The results of the experiments proved that the method capable to measure directly these materials and can provide appropriate calibration curves for determination of unknown concentrations.

  1. Thermochemistry and reaction paths in the oxidation reaction of benzoyl radical: C6H5C•(═O).

    PubMed

    Sebbar, Nadia; Bozzelli, Joseph W; Bockhorn, Henning

    2011-10-27

    Alkyl substituted aromatics are present in fuels and in the environment because they are major intermediates in the oxidation or combustion of gasoline, jet, and other engine fuels. The major reaction pathways for oxidation of this class of molecules is through loss of a benzyl hydrogen atom on the alkyl group via abstraction reactions. One of the major intermediates in the combustion and atmospheric oxidation of the benzyl radicals is benzaldehyde, which rapidly loses the weakly bound aldehydic hydrogen to form a resonance stabilized benzoyl radical (C6H5C(•)═O). A detailed study of the thermochemistry of intermediates and the oxidation reaction paths of the benzoyl radical with dioxygen is presented in this study. Structures and enthalpies of formation for important stable species, intermediate radicals, and transition state structures resulting from the benzoyl radical +O2 association reaction are reported along with reaction paths and barriers. Enthalpies, ΔfH298(0), are calculated using ab initio (G3MP2B3) and density functional (DFT at B3LYP/6-311G(d,p)) calculations, group additivity (GA), and literature data. Bond energies on the benzoyl and benzoyl-peroxy systems are also reported and compared to hydrocarbon systems. The reaction of benzoyl with O2 has a number of low energy reaction channels that are not currently considered in either atmospheric chemistry or combustion models. The reaction paths include exothermic, chain branching reactions to a number of unsaturated oxygenated hydrocarbon intermediates along with formation of CO2. The initial reaction of the C6H5C(•)═O radical with O2 forms a chemically activated benzoyl peroxy radical with 37 kcal mol(-1) internal energy; this is significantly more energy than the 21 kcal mol(-1) involved in the benzyl or allyl + O2 systems. This deeper well results in a number of chemical activation reaction paths, leading to highly exothermic reactions to phenoxy radical + CO2 products.

  2. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10166 1,3-Cyclohexanedione, 2- benzoyl]-, ion(1... substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180;...

  3. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10166 1,3-Cyclohexanedione, 2- benzoyl]-, ion(1... substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180;...

  4. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10166 1,3-Cyclohexanedione, 2- benzoyl]-, ion(1... substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180;...

  5. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10166 1,3-Cyclohexanedione, 2- benzoyl]-, ion(1... substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180;...

  6. 40 CFR 721.10166 - 1,3-Cyclohexanedione, 2-[2-chloro-4-(methylsulfonyl)-3-[(2,2,2-trifluoroethoxy)methyl]benzoyl...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...]-, ion(1-), potassium salt (1:1). 721.10166 Section 721.10166 Protection of Environment ENVIRONMENTAL... Significant New Uses for Specific Chemical Substances § 721.10166 1,3-Cyclohexanedione, 2- benzoyl]-, ion(1... substance identified as 1,3-cyclohexanedione, 2- benzoyl]-, ion(1-), potassium salt (1:1) (PMN P-08-180;...

  7. Products of enzymatic reduction of benzoyl-CoA, a key reaction in anaerobic aromatic metabolism.

    PubMed

    Koch, J; Eisenreich, W; Bacher, A; Fuchs, G

    1993-02-01

    Benzoyl-coenzyme A is the most common central intermediate of anaerobic aromatic metabolism. Studies with whole cells of different bacteria and in vitro had shown that benzoyl-CoA is reduced to alicyclic compounds, possibly via cyclohexadiene intermediates. This reaction is considered a 'biological Birch reduction'. We have elucidated by NMR techniques the structures of six products of [ring-13C6]benzoate reduction. The reaction is catalyzed by extracts from cells of a denitrifying Pseudomonas strain K172 anaerobically grown with benzoate and nitrate as sole carbon and energy sources. The assay mixture contained [ring-13C6]benzoate plus traces of [U-14C]benzoate, Mg2+, ATP, coenzyme A (CoA), and Ti(III) as reductant. The use of the multiply 13C-labelled precursor increases the sensitivity of NMR detection and allows the analysis of crude product mixtures by two-dimensional coherence transfer procedures such as total correlation 13C-NMR spectroscopy and 13C-filtered 1H-NMR spectroscopy. The time course of product formation is consistent with the following order of events. Benzoyl-CoA is formed from benzoate via benzoate-CoA ligase. The first ring reduction product observed is cyclohex-1,5-diene-1-carboxyl-CoA. The next intermediate is 6-hydroxycyclohex-1-ene-1-carboxyl-CoA which is derived from the diene by addition of water. Part of the diene seems to be reduced to cyclohex-1-ene-1-carboxyl-CoA which becomes hydrated to trans-2-hydroxycyclohexane-1-carboxyl-CoA; these two intermediates may be side products in vitro. The first non-cyclic intermediate formed by beta-oxidation is 3-hydroxypimelyl-CoA. This aliphatic C7 dicarboxylic acid is proposed to be oxidized via glutaryl-CoA and crotonyl-CoA to three molecules of acetyl-CoA and one molecule of CO2. A similar product pattern was observed in the benzoate-degrading phototrophic bacterium Rhodopseudomonas palustris. This indicates that the enzymatic reduction of benzoyl-CoA may be mechanistically similar in different

  8. 2-Benzoyl-4-chloro­aniline thio­semi­carbazone

    PubMed Central

    Bandeira, Katlen C. T.; Bresolin, Leandro; Lehmann, Ueslei Z.; Zambiazi, Priscilla J.; de Oliveira, Adriano Bof

    2014-01-01

    In the title compound, C14H13ClN4S, obtained from a reaction of 2-benzoyl-4-chloro­aniline with thio­semicarbazide in ethanol, the dihedral angle between the aromatic rings is 81.31 (13)°. In the crystal, the mol­ecules are linked by three N—H⋯S hydrogen bonds, forming centrosymmetric rings with set-graph motif R 2 2(8) and R 2 2(18), and resulting in the formation of a two-dimensional network lying parallel to (010). PMID:24940260

  9. DFT Study of Pd(0)-Promoted Intermolecular C-H Amination with O-Benzoyl Hydroxylamines.

    PubMed

    Zhou, Yunfei; Bao, Xiaoguang

    2016-09-16

    Computational studies were carried out to explore the mechanism of Pd-catalyzed intermolecular C-H amination with O-benzoyl hydroxylamines in which both Pd(0) and Pd(II) catalysts are effective. For the Pd(0)-catalyzed reaction, the generally assumed Pd(0)/Pd(II) catalytic cycle might not be feasible. Instead, Pd(0), being essentially a catalyst precursor, could be oxidized to Pd(II), and the C-H amination proceeds through the Pd(II)/Pd(IV) catalytic cycle. PMID:27573977

  10. Novel antimicrobial superporous cross-linked chitosan/pyromellitimide benzoyl thiourea hydrogels.

    PubMed

    Mohamed, Nadia A; Abd El-Ghany, Nahed A; Fahmy, Mona M

    2016-01-01

    In this work, chitosan (CS) was cross-linked with different amounts of pyromellitimide benzoyl thiourea moieties. The structure of the cross-linked CS was confirmed by elemental analyses, FTIR and (1)H- NMR spectroscopy. The cross-linking process proceeds via reacting of the amino groups of CS with the isothiocyanate groups of the N,N'-bis [4-(isothiocyanate carbonyl)phenyl] pyromellitimide cross-linker. The amount of the cross-linker was varied with respect to CS to produce four new pyromellitimide benzoyl thiourea cross-linked CS (PIBTU-CS) hydrogels designated as PIBTU-CS-1, PIBTU-CS-2, PIBTU-CS-3, and PIBTU-CS-4 of increasing cross-linking degree percent of 11, 22, 44 and 88%, respectively. The scanning electron microscopy observation indicates the extremely porous structure of the hydrogels. XRD results showed that the crystallinity of CS was decreased upon cross-linking. The four hydrogels exhibit a higher antibacterial activity on Bacillus subtilis and Streptococcus pneumoniae as Gram positive bacteria and against Escherichia coli as Gram negative bacteria and higher antifungal activity on Aspergillus fumigatus, Syncephalastrum racemosum and Geotricum candidum than that of the parent CS as shown from their higher inhibition zone diameters and their lower MIC values. The swell ability of the hydrogel as well as their antimicrobial activity increased with increasing cross-linking density. PMID:26388182

  11. Matrix isolation, time-resolved IR, and computational study of the photochemistry of benzoyl azide

    SciTech Connect

    Pritchina, Elena A.; Gritsan, Nina; Maltsev, Alexander; Bally, Thomas; Autrey, Thomas; Liu, Yonglin; Wang, Yuhong; Toscano, John P.

    2003-06-01

    It was shown recently on the basis of DFT calculations (N. P. Gritsan and E. A. Pritchina, Mendeleev Commun., 2001, 11, 94) that the singlet states of aroylnitrenes undergo tremendous stabilization due to an extra N-O bonding interaction. To test experimentally the multiplicity and the structure of the lowest state of benzoylnitrenes we performed a study of their photochemistry in Ar matrices at 12 K. Formation of two species was observed on irradiation of benzoyl azide (1b) and its 4-acetyl derivative (1c). One of these species has an IR spectrum, which is consistent with that of isocyanate (2b,c). The IR and UV spectra of the second intermediate are in very good agreement with the calculated spectra of the singlet species (3b,c), whose structure is intermediate between that of a carbonylnitrene and an oxazirene. We further examined the photochemistry of benzoyl azide in solution at ambient temperatures by nanosecond time-resolved IR methods and obtained additional evidence for the singlet ground state of benzoylnitrene as well as insight into its reactivity in acetonitrile, cyclohexane, and dichloromethane. The above experiments were accompanied by quantum chemical calculations which included also a thorough investigation of the parent species, formylnitrene, at different levels of theory.

  12. A novel surfactant S-benzoyl-N,N-diethyldithiocarbamate synthesis and its flotation performance to galena

    NASA Astrophysics Data System (ADS)

    Ma, Xin; Hu, Yuan; Zhong, Hong; Wang, Shuai; Liu, Guangyi; Zhao, Gang

    2016-03-01

    In this paper, a novel dithiocarbamate compound, S-benzoyl-N,N-diethyldithiocarbamate (BEDTC), was synthesized via one-pot reaction of diethylamine, carbon disulfide, sodium hydroxide and benzoyl chloride using abundant carbon disulfide as a solvent. Its flotation performance and adsorption mechanism on the galena was first investigated by flotation tests, adsorption quantity measurements, FTIR spectra, X-ray photoelectron spectra (XPS) and density functional theory (DFT) calculation. The flotation results illustrated that BEDTC exhibited stronger collecting power than the conventional sulphide collectors such as sodium diethyl dithiocarbamate (SEDTC) and sodium isobutyl xanthate (SIBX) and superior selectivity for galena against sphalerite. The adsorption data demonstrated that the adsorption affinity of BEDTC to galena was stronger than that of SEDTC and SIBX, and the preferable pH range for BEDTC adsorption on galena surfaces was 6-10. The results of FTIR spectra and XPS indicated that the interaction of BEDTC with galena may be dominated by the chemical adsorption, which was further confirmed by DFT calculation. BEDTC probably acted as a bidentate ligand, bonding with lead through the thiol sulfur and carbonyl oxygen atoms to form two distinct adsorption geometries, one with the same Pb atom to form a six-membered ring complex, and the other with two different Pb atoms to form a "bullet" shape complex.

  13. Comparison of a chlorhexidine and a benzoyl peroxide shampoo as sole treatment in canine superficial pyoderma.

    PubMed

    Loeffler, A; Cobb, M A; Bond, R

    2011-09-01

    The clinical and antibacterial efficacy of two shampoos used as a sole antibacterial treatment in dogs with superficial pyoderma were investigated and compared. In a randomised, partially blinded study, a 3 per cent chlorhexidine gluconate shampoo (Chlorhex 3; Leo Animal Health) was compared against a 2.5 per cent benzoyl peroxide shampoo (Paxcutol; Virbac) in 22 dogs with superficial pyoderma. Dogs were washed two to three times weekly with a 10-minute contact time over 21 days. Clinical scores and bacterial counts were assessed on days 1, 8 and 22 and compared within and between treatment groups; overall response was assessed at the end of the study. Twenty dogs completed the study; 15 (68.2 per cent) showed an overall clinical improvement and the clinical signs resolved in three chlorhexidine-treated dogs. In the chlorhexidine-treated group, scores for papules/pustules (P<0.001), investigator-assessed pruritus (P=0.003), total bacterial counts (P=0.003) and counts for coagulase-positive staphylococci (P=0.003) were reduced after three weeks. Scores and bacterial counts did not vary significantly in the benzoyl peroxide-treated group.

  14. Novel antimicrobial superporous cross-linked chitosan/pyromellitimide benzoyl thiourea hydrogels.

    PubMed

    Mohamed, Nadia A; Abd El-Ghany, Nahed A; Fahmy, Mona M

    2016-01-01

    In this work, chitosan (CS) was cross-linked with different amounts of pyromellitimide benzoyl thiourea moieties. The structure of the cross-linked CS was confirmed by elemental analyses, FTIR and (1)H- NMR spectroscopy. The cross-linking process proceeds via reacting of the amino groups of CS with the isothiocyanate groups of the N,N'-bis [4-(isothiocyanate carbonyl)phenyl] pyromellitimide cross-linker. The amount of the cross-linker was varied with respect to CS to produce four new pyromellitimide benzoyl thiourea cross-linked CS (PIBTU-CS) hydrogels designated as PIBTU-CS-1, PIBTU-CS-2, PIBTU-CS-3, and PIBTU-CS-4 of increasing cross-linking degree percent of 11, 22, 44 and 88%, respectively. The scanning electron microscopy observation indicates the extremely porous structure of the hydrogels. XRD results showed that the crystallinity of CS was decreased upon cross-linking. The four hydrogels exhibit a higher antibacterial activity on Bacillus subtilis and Streptococcus pneumoniae as Gram positive bacteria and against Escherichia coli as Gram negative bacteria and higher antifungal activity on Aspergillus fumigatus, Syncephalastrum racemosum and Geotricum candidum than that of the parent CS as shown from their higher inhibition zone diameters and their lower MIC values. The swell ability of the hydrogel as well as their antimicrobial activity increased with increasing cross-linking density.

  15. 2-Benzoyl-6-benzylidenecyclohexanone analogs as potent dual inhibitors of acetylcholinesterase and butyrylcholinesterase.

    PubMed

    Leong, Sze Wei; Abas, Faridah; Lam, Kok Wai; Shaari, Khozirah; Lajis, Nordin H

    2016-08-15

    In the present study, a series of 2-benzoyl-6-benzylidenecyclohexanone analogs have been synthesized and evaluated for their anti-cholinesterase activity. Among the forty-one analogs, four compounds (38, 39, 40 and 41) have been identified as lead compounds due to their highest inhibition on both AChE and BChE activities. Compounds 39 and 40 in particular exhibited highest inhibition on both AChE and BChE with IC50 values of 1.6μM and 0.6μM, respectively. Further structure-activity relationship study suggested that presence of a long-chain heterocyclic in one of the rings played a critical role in the dual enzymes' inhibition. The Lineweaver-Burk plots and docking results suggest that both compounds could simultaneously bind to the PAS and CAS regions of the enzyme. ADMET analysis further confirmed the therapeutic potential of both compounds based upon their high BBB-penetrating. Thus, 2-benzoyl-6-benzylidenecyclohexanone containing long-chain heterocyclic amine analogs represent a new class of cholinesterase inhibitor, which deserve further investigation for their development into therapeutic agents for cognitive diseases such as Alzheimer. PMID:27328658

  16. cis-Bis(N-benzoyl-N′,N′-dibenzyl­thio­ureato-κ2 O,S)nickel(II)

    PubMed Central

    Pérez, Hiram; Corrêa, Rodrigo S.; Duque, Julio; Plutín, Ana M.; O’Reilly, Beatriz

    2008-01-01

    In the title compound, [Ni(C22H19N2OS)2], the NiII atom is coordinated by the S and O atoms of two N-benzoyl-N′,N′-dibenzyl­thio­ureate ligands in a slightly distorted square-planar geometry. The two O atoms are cis, as are the two S atoms. PMID:21202775

  17. Thermochemistry and reaction paths in the oxidation reaction of benzoyl radical: C6H5C•(═O).

    PubMed

    Sebbar, Nadia; Bozzelli, Joseph W; Bockhorn, Henning

    2011-10-27

    Alkyl substituted aromatics are present in fuels and in the environment because they are major intermediates in the oxidation or combustion of gasoline, jet, and other engine fuels. The major reaction pathways for oxidation of this class of molecules is through loss of a benzyl hydrogen atom on the alkyl group via abstraction reactions. One of the major intermediates in the combustion and atmospheric oxidation of the benzyl radicals is benzaldehyde, which rapidly loses the weakly bound aldehydic hydrogen to form a resonance stabilized benzoyl radical (C6H5C(•)═O). A detailed study of the thermochemistry of intermediates and the oxidation reaction paths of the benzoyl radical with dioxygen is presented in this study. Structures and enthalpies of formation for important stable species, intermediate radicals, and transition state structures resulting from the benzoyl radical +O2 association reaction are reported along with reaction paths and barriers. Enthalpies, ΔfH298(0), are calculated using ab initio (G3MP2B3) and density functional (DFT at B3LYP/6-311G(d,p)) calculations, group additivity (GA), and literature data. Bond energies on the benzoyl and benzoyl-peroxy systems are also reported and compared to hydrocarbon systems. The reaction of benzoyl with O2 has a number of low energy reaction channels that are not currently considered in either atmospheric chemistry or combustion models. The reaction paths include exothermic, chain branching reactions to a number of unsaturated oxygenated hydrocarbon intermediates along with formation of CO2. The initial reaction of the C6H5C(•)═O radical with O2 forms a chemically activated benzoyl peroxy radical with 37 kcal mol(-1) internal energy; this is significantly more energy than the 21 kcal mol(-1) involved in the benzyl or allyl + O2 systems. This deeper well results in a number of chemical activation reaction paths, leading to highly exothermic reactions to phenoxy radical + CO2 products. PMID:21942384

  18. N-Benzoyl-N′,N′′-dicyclo­hexyl­phospho­ric triamide

    PubMed Central

    Pourayoubi, Mehrdad; Rostami Chaijan, Mahnaz; Torre-Fernández, Laura; García-Granda, Santiago

    2011-01-01

    In the title compound, C19H30N3O2P, the central P atom has a distorted tetra­hedral configuration. The N atoms in both cyclo­hexyl­amide moieties exhibit a slight deviation [0.32 (7) and 0.44 (6) Å] from planarity, while the benzoyl­amide N atom is planar [0.11 (3) Å]. In the crystal, mol­ecules are linked via N—H⋯O(P) and N—H⋯O(C) hydrogen bonds, forming R 2 2(10) rings within linear arrangements parallel to the b axis. PMID:21754754

  19. Molecular structure and thermal behavior of N-Benzoyl-3,3-dinitroazetidine

    NASA Astrophysics Data System (ADS)

    Yan, Biao; Zhao, Ningning; Mai, Tao; Xu, Kangzhen; Ma, Haixia; Song, Jirong

    2012-12-01

    N-Benzoyl-3,3-dinitroazetidine (BDNAZ) has been synthesized and characterized by elemental analysis, FT-IR spectroscopy, 1H NMR and X-ray single crystal diffraction technique. BDNAZ crystallizes in the monoclinic space group P21/ c. Its thermal behavior was studied under a non-isothermal condition by DSC and TG/DTG methods, the value of E a and A of the exothermic decomposition reaction of BDNAZ are 143.19 kJ mol-1 and 1014.34 s-1, respectively. The specific heat capacity of BDNAZ was determined with a continuous C p mode of micro-calorimeter and theoretical calculation. The adiabatic time-to-explosion was evaluated as 109.9-124.4 s.

  20. Benzoyl Peroxide Oxidation Route to the Synthesis of Solvent Soluble Polycarbazole

    PubMed Central

    Boddula, Rajender; Srinivasan, Palaniappan

    2014-01-01

    Carbazole was oxidized by benzoyl peroxide in presence of p-toluenesulfonic acid to polycarbazole salt at room temperature for the first time. Polycarbazole salts were synthesized via solution and emulsion polymerization pathways. Polycarbazole bases were prepared by dedoping from polycarbazole salts. Formation of polycarbazoles was confirmed from infrared, electronic absorption and EDAX spectra. Polycarbazole salt was obtained in amorphous nature in semiconductor range (10−5 S/cm), which was found to be soluble in less and high polar solvents. Polycarbazole salt prepared by emulsion polymerization pathway showed mixture of shapes with microrod, sphere, and pores, whereas its corresponding base showed only micropores structure. On the other hand, polycarbazole salt and its corresponding base prepared by solution polymerization pathway showed flake-like morphology. Higher thermal stability was obtained for polycarbazole salt prepared by emulsion polymerization pathway than that of the salt prepared by solution polymerization pathway. PMID:27336060

  1. DFT MODELING OF BENZOYL PEROXIDE ADSORPTION ON α-Cr2O3 (0001) SURFACE

    NASA Astrophysics Data System (ADS)

    Maldonado, Frank; Stashans, Arvids

    2016-04-01

    Density functional theory (DFT) within the generalized gradient approximation (GGA) has been used to investigate possible adsorption configurations of benzoyl peroxide (BPO) molecule on the chromium oxide (α-Cr2O3) (0001) surface. Two configurations are found to lead to the molecular adsorption with corresponding adsorption energies being equal to -0.16 and -0.48eV, respectively. Our work describes in detail atomic displacements for both crystalline surface and adsorbate as well as discusses electronic and magnetic properties of the system. The most favorable adsorption case is found when the chemical bond between one of the molecular oxygens and one of the surface Cr atoms has been formed.

  2. Crystal structure of the enol form of mesotrione: a benzoyl-cyclo-hexa-nedione herbicide.

    PubMed

    Kang, Gihaeng; Kim, Jineun; Park, Hyunjin; Kim, Tae Ho

    2015-08-01

    The title compound [systematic name: 3-hy-droxy-2-(4-methyl-sulfonyl-2-nitro-benzo-yl)cyclo-hex-2-enone], C14H13NO7S, is the enol form of a benzoyl-cyclo-hexa-nedione herbicide. As a result of this tautomerization, there is intra-molecular O-H⋯O hydrogen bond enclosing an S(6) ring motif. The cyclo-hexene ring has an envelope conformation, with the central CH2 C atom as the flap. Its mean plane is inclined to the benzene ring by 87.46 (8)°. In the crystal, mol-ecules are linked by a series of C-H⋯O hydrogen bonds, forming a three-dimensional framework. PMID:26396790

  3. Development of N-(Functionalized benzoyl)-homocycloleucyl-glycinonitriles as Potent Cathepsin K Inhibitors.

    PubMed

    Borišek, Jure; Vizovišek, Matej; Sosnowski, Piotr; Turk, Boris; Turk, Dušan; Mohar, Barbara; Novič, Marjana

    2015-09-10

    Cathepsin K is a major drug target for osteoporosis and related-bone disorders. Using a combination of virtual combinatorial chemistry, QSAR modeling, and molecular docking studies, a series of cathepsin K inhibitors based on N-(functionalized benzoyl)-homocycloleucyl-glycinonitrile scaffold was developed. In order to avoid previous problems of cathepsin K inhibitors associated with lysosomotropism of compounds with basic character that resulted in off-target effects, a weakly- to nonbasic moiety was incorporated into the P3 position. Compounds 5, 6, and 9 were highly selective for cathepsin K when compared with cathepsins L and S, with the Ki values in the 10-30 nM range. The kinetic studies revealed that the new compounds exhibited reversible tight binding to cathepsin K, while the X-ray structural studies showed covalent and noncovalent binding between the nitrile group and the catalytic cysteine (Cys25) site.

  4. A double-blind clinical trial with a lotion containing 5% benzoyl peroxide and 2% miconazole in patients with acne vulgaris.

    PubMed

    Mesquita-Guimarães, J; Ramos, S; Tavares, M R; Carvalho, M R

    1989-09-01

    The therapeutic efficacy of a lotion containing 5% benzoyl peroxide and 2% miconazole was compared with 5% benzoyl peroxide alone, in a double-blind, randomized, parallel study. Thirty patients with comedonal or inflammatory acne vulgaris were enrolled. The medications were applied once daily during the first week, and then twice daily for the rest of the trial (45 days). In patients with comedonal acne there was no difference in the effect of the two therapies. In patients with inflammatory acne the percentage reduction of the number of lesions on Day 30 was significantly higher in the benzoyl peroxide plus miconazole group (66%) compared to benzoyl peroxide alone (37%). At Day 45 there was a trend favouring the combined therapy but the difference was not significant. There were no significant differences in the adverse reactions reported by the two groups of patients (erythema, itching or moderate exfoliation).

  5. The biosynthesis of phytoalexins in Dianthus caryophyllus L. cell cultures: induction of benzoyl-CoA:anthranilate N-benzoyltransferase activity.

    PubMed

    Reinhard, K; Matern, U

    1989-11-15

    It has been shown that cell cultures of Dianthus caryophyllus L. c.v. Eleganz accumulate N-benzoyl-4-methoxyanthranilic acid, previously identified as the phytoalexin methoxydianthramide B, in response to treatment either with a crude elicitor isolated from the cell walls of Phytophthora megasperma f.sp. glycinea or with a commercial yeast extract. Cell-free extracts from the induced cells efficiently catalyzed the N-benzoylation of anthranilate in the presence of benzoyl-CoA. The partially purified transferase was shown to be specific for anthranilate with almost no activity toward 4-hydroxyanthranilate, whereas acyl donors other than benzoyl-CoA such as salicyloyl-, cinnamoyl-, or 4-coumaroyl-CoA were also accepted. Elicitor treatment of the cells additionally induced an S-adenosyl-L-methionine:N-benzoyl-4-hydroxyanthranilate 4-O-methyltransferase activity. We propose, therefore, that methoxydianthramide B is derived from N-benzoylanthranilic acid via N-benzoyl-4-hydroxyanthranilic acid. Dark-grown cells contained little N-benzoyltransferase activity (approx 8 mu kat/kg), which increased roughly ninefold within 6 h following the addition of the elicitor. In addition, phenylalanine ammonia-lyase activity of the cells increased about twofold under these conditions to a maximum (approx 40 mu kat/kg) at 5 h. The rapid induction of both enzyme activities suggests that the shikimate pathway is of crucial importance in the disease resistance response of carnation cells.

  6. Supra­molecular hydrogen-bonding patterns in the N(9)—H protonated and N(7)—H tautomeric form of an N6-benzoyl­adenine salt: N 6-benzoyl­adeninium nitrate

    PubMed Central

    Karthikeyan, Ammasai; Jeeva Jasmine, Nithianantham; Thomas Muthiah, Packianathan; Perdih, Franc

    2016-01-01

    In the title molecular salt, C12H10N5O+·NO3 −, the adenine unit has an N 9-protonated N(7)—H tautomeric form with non-protonated N1 and N3 atoms. The dihedral angle between the adenine ring system and the phenyl ring is 51.10 (10)°. The typical intra­molecular N7—H⋯O hydrogen bond with an S(7) graph-set motif is also present. The benzoyl­adeninium cations also form base pairs through N—H⋯O and C—H⋯N hydrogen bonds involving the Watson–Crick face of the adenine ring and the C and O atoms of the benzoyl ring of an adjacent cation, forming a supra­molecular ribbon with R 2 2(9) rings. Benzoyl­adeninum cations are also bridged by one of the oxygen atoms of the nitrate anion, which acts as a double acceptor, forming a pair of N—H⋯O hydrogen bonds to generate a second ribbon motif. These ribbons together with π–π stacking inter­actions between the phenyl ring and the five- and six-membered adenine rings of adjacent mol­ecules generate a three-dimensional supra­molecular architecture. PMID:26958373

  7. Amperometric detection of benzoyl peroxide in pharmaceutical preparations using carbon paste electrodes with peroxidases naturally immobilized on coconut fibers.

    PubMed

    Kozan, J V B; Silva, R P; Serrano, S H P; Lima, A W O; Angnes, L

    2010-01-15

    This paper describes the applications of a new carbon paste electrode containing fibers of coconut (Cocus nucifera L.) fruit, which are very rich in peroxidase enzymes naturally immobilized on its structure. The new sensor was applied for the amperometric quantification of benzoyl peroxide in facial creams and dermatological shampoos. The amperometric measurements were performed in 0.1 mol L(-1) phosphate buffer (pH 5.2), at 0.0 V (versus Ag/AgCl). On these conditions, benzoyl peroxide was rapidly determined in the 5.0-55 micromol L(-1), with a detection limit of 2.5 micromol L(-1) (s/n=3), response time of 4.1 s (90% of the steady state) and sensitivity limit of 0.33 A mol L(-1) cm(-2). The amperometric results are in good agreement with those obtained by spectrophotometric technique, used as a standard method.

  8. Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory

    NASA Astrophysics Data System (ADS)

    Callam, Christopher S.; Lowary, Todd L.

    2001-01-01

    We report an organic chemistry laboratory experiment in which methyl 2,3,5-tri-O-benzoyl-a-D-arabinofuranoside is synthesized. The product is obtained in two steps from commercially available D-arabinose, via Fischer glycosylation and benzoylation. The product is easily purified by crystallization. The primary purpose in implementing this experiment was to give students additional exposure to carbohydrate chemistry. In addition, the experiment provides an opportunity to discuss a number of other topics including kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity. It is also possible to incorporate 2-D NMR spectroscopy into this experiment.

    See Correction to this article.

  9. The effect of dietary lipid on skin tumor promotion by benzoyl peroxide: comparison of fish, coconut and corn oil.

    PubMed

    Locniskar, M; Belury, M A; Cumberland, A G; Patrick, K E; Fischer, S M

    1991-06-01

    Fish or vegetable oils were fed during the promotion stage of a mouse skin carcinogenesis model in order to investigate the effects of dietary fat on tumor development. Two weeks after initiation with 10 nmol dimethylbenz[a]anthracene, SENCAR mice were divided into five groups and maintained on one of the following semipurified diets containing 10% total fat and varying the type of fat: 8.5% coconut oil (CT)/1.5% corn oil (CO); 1% menhaden oil (MO)/7.5% CT/1.5% CO; 4% MO/4.5% CT/1.5% CO; 8.5% MO/1.5% CO; or 10% CO. Promotion with twice-weekly applications of 40 mg benzoyl peroxide was begun 2 weeks later and continued for 52 weeks. No statistically significant differences in kcal food consumed or body weights were observed between diet groups. Papilloma latency, incidence and yield differed among the diet groups with the group fed the 8.5% CT/1.5% CO diet having the shortest latency and highest papilloma incidence and number. In addition, carcinoma latency and incidence was assessed and the first carcinoma appeared in the group fed 8.5% CT/1.5% CO after 20 weeks of benzoyl peroxide treatment; this group yielded the highest carcinoma incidence throughout the study. In comparison, the group fed the 10% CO diet had the longest latency period, and among the lowest papilloma and carcinoma incidence and fewest tumors. In parallel studies, ornithine decarboxylase activity, vascular permeability and hyperplasia were elevated in the epidermis of benzoyl peroxide-treated mice but the extent of the response did not correlate with the different rates of tumor formation observed among the diet groups. These data indicate that dietary fat modulates tumor promotion by benzoyl peroxide in this skin carcinogenesis model with the predominantly saturated fat diet producing the highest rates of papilloma and carcinogen formation and the polyunsaturated fat diet the lowest.

  10. The effect of dietary lipid on skin tumor promotion by benzoyl peroxide: comparison of fish, coconut and corn oil.

    PubMed

    Locniskar, M; Belury, M A; Cumberland, A G; Patrick, K E; Fischer, S M

    1991-06-01

    Fish or vegetable oils were fed during the promotion stage of a mouse skin carcinogenesis model in order to investigate the effects of dietary fat on tumor development. Two weeks after initiation with 10 nmol dimethylbenz[a]anthracene, SENCAR mice were divided into five groups and maintained on one of the following semipurified diets containing 10% total fat and varying the type of fat: 8.5% coconut oil (CT)/1.5% corn oil (CO); 1% menhaden oil (MO)/7.5% CT/1.5% CO; 4% MO/4.5% CT/1.5% CO; 8.5% MO/1.5% CO; or 10% CO. Promotion with twice-weekly applications of 40 mg benzoyl peroxide was begun 2 weeks later and continued for 52 weeks. No statistically significant differences in kcal food consumed or body weights were observed between diet groups. Papilloma latency, incidence and yield differed among the diet groups with the group fed the 8.5% CT/1.5% CO diet having the shortest latency and highest papilloma incidence and number. In addition, carcinoma latency and incidence was assessed and the first carcinoma appeared in the group fed 8.5% CT/1.5% CO after 20 weeks of benzoyl peroxide treatment; this group yielded the highest carcinoma incidence throughout the study. In comparison, the group fed the 10% CO diet had the longest latency period, and among the lowest papilloma and carcinoma incidence and fewest tumors. In parallel studies, ornithine decarboxylase activity, vascular permeability and hyperplasia were elevated in the epidermis of benzoyl peroxide-treated mice but the extent of the response did not correlate with the different rates of tumor formation observed among the diet groups. These data indicate that dietary fat modulates tumor promotion by benzoyl peroxide in this skin carcinogenesis model with the predominantly saturated fat diet producing the highest rates of papilloma and carcinogen formation and the polyunsaturated fat diet the lowest. PMID:1904320

  11. Tris(N-benzoyl-N′,N′-diphenyl­thio­ureato-κ2 O,S)cobalt(III)

    PubMed Central

    Pérez, Hiram; Mascarenhas, Yvonne; Plutín, Ana María; de Souza Corrêa, Rodrigo; Duque, Julio

    2008-01-01

    In the title compound, [Co(C20H15N2OS)3], the CoIII atom is coordinated by the S and O atoms of three N-benzoyl-N′,N′-diphenyl­thio­urea ligands in a slightly distorted octa­hedral geometry. The O and S atoms are in cis positions, while the positions between the O and S atoms are trans. PMID:21201883

  12. Development and in-vitro characterization of fish oil oleogels containing benzoyl peroxide and salicylic acid as keratolytic agents.

    PubMed

    Rehman, K; Tan, C M; Zulfakar, M H

    2014-03-01

    Topical keratolytic agents such as benzoyl peroxide (BP) and salicylic acid (SA) are one of the common treatments for inflammatory skin diseases. However, the amount of drug delivery through the skin is limited due to the stratum corneum. The purposes of this study were to investigate the ability of fish oil to act as penetration enhancer for topical keratolytic agents and to determine the suitable gelator for formulating stable fish oil oleogels. 2 types of gelling agents, beeswax and sorbitan monostearate (Span 60), were used to formulate oleogels. To investigate the efficacy of fish oil oleogel permeation, commercial hydrogels of benzoyl peroxide (BP) and salicylic acid (SA) were used as control, and comparative analysis was performed using Franz diffusion cell. Stability of oleogels was determined by physical assessments at 20°C and 40°C storage. Benzoyl peroxide (BP) fish oil oleogels containing beeswax were considered as better formulations in terms of drug permeation and cumulative drug release. All the results were found to be statistically significant (p<0.05, ANOVA) and it was concluded that the beeswax-fish oil combination in oleogel can prove to be beneficial in terms of permeation across the skin and stability.

  13. Synthesis and antiproliferative activity of novel 2-aryl-4-benzoyl-imidazole derivatives targeting tubulin polymerization

    PubMed Central

    Chen, Jianjun; Li, Chien-Ming; Wang, Jin; Ahn, Sunjoo; Wang, Zhao; Lu, Yan; Dalton, James T.; Miller, Duane D.; Li, Wei

    2011-01-01

    We previously reported the discovery of 2-aryl-4-benzoyl-imidazoles (ABI-I) as potent antiproliferative agents for melanoma. To further understand the structural requirements for the potency of ABI analogs, gain insight in the structure-activity relationships (SAR), and investigate metabolic stability for these compounds, we report extensive SAR studies on the ABI-I scaffold. Compared with the previous set of ABI-I analogs, the newly synthesized ABI-II analogs have lower potency in general, but some of the new analogs have comparable potency to the most active compounds in the previous set when tested in two melanoma and four prostate cancer cell lines. These SAR studies indicated that the antiproliferative activity was very sensitive to subtle changes in the ligand. Tested compounds 3ab and 8a are equally active against highly paclitaxel resistant cancer cell lines and their parental cell lines, indicating that drugs developed based on ABI-I analogs may have therapeutic advantages over paclitaxel in treating resistant tumors. Metabolic stability studies of compound 3ab revealed that N-methyl imidazole failed to extend stability as literature reported because de-methylation was found as the major metabolic pathway in rat and mouse liver microsomes. However, this sheds light on the possibility for many modifications on imidazole ring for further lead optimization since the modification on imidazole, such as compound 3ab, did not impact the potency. PMID:21775150

  14. Design, synthesis, and anti-melanogenic effects of (E)-2-benzoyl-3-(substituted phenyl)acrylonitriles

    PubMed Central

    Yun, Hwi Young; Kim, Do Hyun; Son, Sujin; Ullah, Sultan; Kim, Seong Jin; Kim, Yeon-Jeong; Yoo, Jin-Wook; Jung, Yunjin; Chun, Pusoon; Moon, Hyung Ryong

    2015-01-01

    Background Tyrosinase is the most prominent target for inhibitors of hyperpigmentation because it plays a critical role in melaninogenesis. Although many tyrosinase inhibitors have been identified, from both natural and synthetic sources, there remains a considerable demand for novel tyrosinase inhibitors that are safer and more effective. Methods (E)-2-Benzoyl-3-(substituted phenyl)acrylonitriles (BPA analogs) with a linear β-phenyl-α,β-unsaturated carbonyl scaffold were designed and synthesized as potential tyrosinase inhibitors. We evaluated their effects on cellular tyrosinase activity and melanin biosynthesis in murine B16F10 melanoma cells and their ability to inhibit mushroom tyrosinase activity. Results BPA analogs exhibited inhibitory activity against mushroom tyrosinase. In particular, BPA13 significantly suppressed melanin biosynthesis and inhibited cellular tyrosinase activity in B16F10 cells in a dose-dependent manner. A docking study revealed that BPA13 had higher binding affinity for tyrosinase than kojic acid. Conclusion BPA13, which possesses a linear β-phenyl-α,β-unsaturated carbonyl scaffold, is a potential candidate skin-whitening agent and treatment for diseases associated with hyperpigmentation. PMID:26347064

  15. [Detection of benzoyl peroxide in wheat flour by NIR diffuse reflectance spectroscopy technique].

    PubMed

    Zhang, Zhi-yong; Li, Gang; Liu, Hai-xue; Lin, Ling; Zhang, Bao-ju; Wu, Xiao-rong

    2011-12-01

    Adding benzoyl peroxide (BPO) into wheat flour was prohibited by the relevant government departments since May 1, 2011. And it is of great importance to detect BPO additive amount in wheat flour quickly and accurately. Part of BPO which was added into wheat flour will be deoxidized into benzoic acid, and this make it complex to detect the original BPO additive amount. The objective of the present research is to investigate the potential of NIR diffuse reflectance spectroscopy as a way for measurement of BPO original adding amount in wheat flour. A total of 133 wheat flour samples were prepared by adding different content of BPO into pure wheat flour. Spectra data were obtained by NIR spectrometer and then denoised by wavelet transform. Ninety seven samples were taken as calibration set and other 36 samples as prediction set. Partial least squares regression (PLSR) was applied to establish the calibration model between BPO original adding contents and the spectra data. The determination coefficient of model for the calibration set is 0.8901, and root mean squared error of calibration (RMSEC) is 40.85 mg x kg(-1). The determination coefficient for the prediction set is 0.8865, and root mean squared error of prediction (RMSEP) is 44.69 mg x kg(-1). The result indicates that it is feasible to detect the BPO adding contents in wheat flour by NIR diffuse reflectance spectroscopy technique and this technique has the potential to measure some other additives in food.

  16. [Detection of benzoyl peroxide in wheat flour by NIR diffuse reflectance spectroscopy technique].

    PubMed

    Zhang, Zhi-yong; Li, Gang; Liu, Hai-xue; Lin, Ling; Zhang, Bao-ju; Wu, Xiao-rong

    2011-12-01

    Adding benzoyl peroxide (BPO) into wheat flour was prohibited by the relevant government departments since May 1, 2011. And it is of great importance to detect BPO additive amount in wheat flour quickly and accurately. Part of BPO which was added into wheat flour will be deoxidized into benzoic acid, and this make it complex to detect the original BPO additive amount. The objective of the present research is to investigate the potential of NIR diffuse reflectance spectroscopy as a way for measurement of BPO original adding amount in wheat flour. A total of 133 wheat flour samples were prepared by adding different content of BPO into pure wheat flour. Spectra data were obtained by NIR spectrometer and then denoised by wavelet transform. Ninety seven samples were taken as calibration set and other 36 samples as prediction set. Partial least squares regression (PLSR) was applied to establish the calibration model between BPO original adding contents and the spectra data. The determination coefficient of model for the calibration set is 0.8901, and root mean squared error of calibration (RMSEC) is 40.85 mg x kg(-1). The determination coefficient for the prediction set is 0.8865, and root mean squared error of prediction (RMSEP) is 44.69 mg x kg(-1). The result indicates that it is feasible to detect the BPO adding contents in wheat flour by NIR diffuse reflectance spectroscopy technique and this technique has the potential to measure some other additives in food. PMID:22295772

  17. Hybrid molecules of carvacrol and benzoyl urea/thiourea with potential applications in agriculture and medicine.

    PubMed

    Pete, Umesh D; Zade, Chetan M; Bhosale, Jitendra D; Tupe, Santosh G; Chaudhary, Preeti M; Dikundwar, Amol G; Bendre, Ratnamala S

    2012-09-01

    Benzoyl phenyl urea, a class of insect growth regulator's acts by inhibiting chitin synthesis. Carvacrol, a naturally occurring monoterpenoid is an effective antifungal agent. We have structurally modified carvacrol (2-methyl-5-[1-methylethyl] phenol) by introducing benzoylphenyl urea linkage. Two series of benzoylcarvacryl thiourea (BCTU, 4a-f) and benzoylcarvacryl urea (BCU, 5a-f) derivatives were prepared and characterized by elemental analysis, IR, (1)H and (13)C NMR and Mass spectroscopy. Derivatives 4b, 4d, 4e, 4f and 5d, 5f showed comparable insecticidal activity with the standard BPU lufenuron against Dysdercus koenigii. BCTU derivatives 4c, 4e and BCU 5c showed good antifungal activity against phytopathogenic fungi viz. Magnaporthe grisae, Fusarium oxysporum, Dreschlera oryzae; food spoilage yeasts viz. Debaromyces hansenii, Pichia membranifaciens; and human pathogens viz. Candida albicans and Cryptococcus neoformans. Compounds 5d, 5e and 5f showed potent activity against human pathogens. Moderate and selective activity was observed for other compounds. All the synthesized compounds were non-haemolytic. These compounds have potential application in agriculture and medicine. PMID:22850211

  18. Polymeric micellar nanocarriers of benzoyl peroxide as potential follicular targeting approach for acne treatment.

    PubMed

    Kahraman, Emine; Özhan, Gül; Özsoy, Yıldız; Güngör, Sevgi

    2016-10-01

    The aim of this work was to optimize polymeric nano-sized micellar carriers of the anti-acne compound benzoyl peroxide (BPO) and to examine the ability of these carriers to deposit into hair follicles with the objective of improving skin delivery of BPO. BPO loaded polymeric micelles composed of Pluronic(®) F127 were prepared by the thin film hydration method and characterized in terms of size, loading capacity, morphology and physical stability. The optimized micelle formulation was then selected for skin delivery studies. The penetration of BPO loaded micellar carriers into skin and skin appendages across full thickness porcine skin was examined in vitro. Confocal microscopy images confirmed the penetration of Nile Red into hair follicles, which was loaded into micellar carriers as a model fluorescent compound. The relative safety of the polymeric micelles was evaluated with the MTT viability test using mouse embryonic fibroblasts. The results indicated that nano-sized polymeric micelles of BPO composed of Pluronic(®) F127 offer a potential approach to enhance skin delivery of BPO and that targeting of micelles into hair follicles may be an effective and safe acne treatment. PMID:27434156

  19. Polymeric micellar nanocarriers of benzoyl peroxide as potential follicular targeting approach for acne treatment.

    PubMed

    Kahraman, Emine; Özhan, Gül; Özsoy, Yıldız; Güngör, Sevgi

    2016-10-01

    The aim of this work was to optimize polymeric nano-sized micellar carriers of the anti-acne compound benzoyl peroxide (BPO) and to examine the ability of these carriers to deposit into hair follicles with the objective of improving skin delivery of BPO. BPO loaded polymeric micelles composed of Pluronic(®) F127 were prepared by the thin film hydration method and characterized in terms of size, loading capacity, morphology and physical stability. The optimized micelle formulation was then selected for skin delivery studies. The penetration of BPO loaded micellar carriers into skin and skin appendages across full thickness porcine skin was examined in vitro. Confocal microscopy images confirmed the penetration of Nile Red into hair follicles, which was loaded into micellar carriers as a model fluorescent compound. The relative safety of the polymeric micelles was evaluated with the MTT viability test using mouse embryonic fibroblasts. The results indicated that nano-sized polymeric micelles of BPO composed of Pluronic(®) F127 offer a potential approach to enhance skin delivery of BPO and that targeting of micelles into hair follicles may be an effective and safe acne treatment.

  20. Bioavailability of Clindamycin From a New Clindamycin Phosphate 1.2%-Benzoyl Peroxide 3% Combination Gel.

    PubMed

    Jones, Terry M; Jasper, Stacy; Alió Sáenz, Alessandra B

    2013-01-01

    A new topical fixed-dose combination product containing clindamycin (1%, formulated as 1.2% clindamycin phosphate, CLNP 1.2%) with low strength (3%) benzoyl peroxide (BPO) in a methylparaben-free gel vehicle (CLNP 1.2%-BPO 3%-MPF) has been developed for the treatment of acne. The objective of this study was to determine the relative bioavailability of clindamycin and clindamycin sulfoxide from CLNP 1.2%-BPO 3%-MPF compared with clindamycin phosphate 1.2%-BPO 5% in a methylparaben-preserved gel vehicle (CLNP 1.2%-BPO 5%-MP) and clindamycin phosphate 1.2%-BPO 5% in a methylparaben-free gel vehicle (CLNP 1.2%-BPO 5%-MPF), and to determine whether exposure is affected by BPO concentration (3% vs. 5%) when applied topically. Seventy-two subjects with moderate-severe acne were randomized to receive CLNP 1.2%-BPO 3%-MPF, CLNP 1.2%-BPO 5%-MP, or CLNP 1.2%-BPO 5%-MPF in a 5-day, open-label, and parallel-group study. Cmax and AUC values for clindamycin were highest for CLNP 1.2%-BPO 5%-MP, followed by CLNP 1.2%-BPO 3%-MPF and CLNP 1.2%-BPO 5%-MPF, but differences were not statistically significant. Systemic exposure to clindamycin and clindamycin sulfoxide was low and comparable between the formulations. Results indicate that differences in BPO concentration do not influence clindamycin bioavailability.

  1. Mitochondrial nicotinamide nucleotide transhydrogenase: active site modification by 5'-(p-(fluorosulfonyl)benzoyl)adenosine

    SciTech Connect

    Phelps, D.C.; Hatefi, Y.

    1985-07-02

    Membrane-bound and purified mitochondrial energy-linked nicotinamide nucleotide transhydrogenase (TH) was inhibited by incubation with 5'-(p-(fluorosulfonyl)benzoyl)adenosine (FSBA), which is an analogue of TH substrates and their competitive inhibitors, namely, 5'-, 2'-, or 3'-AMP. NAD(H) and analogues, NADP, 5'-AMP, 5'-ADP, and 2'-AMP/3'-AMP mixed isomers protected TH against inhibition by FSBA, but NADPH accelerated the inhibition rate. In the absence of protective ligands or in the presence of NADP, FSBA appeared to modify the NAD(H) binding site of TH, because, unlike unmodified TH, the enzyme modified by FSBA under these conditions did not bind to an NAD-affinity column (NAD-agarose). However, when the NAD(H) binding site of TH was protected in the presence of 5'-AMP or NAD, then FSBA modification resulted in an inhibited enzyme that did bind to NAD-agarose, suggesting FSBA modification of the NADP(H) binding site or an essential residue outside the active site. (/sup 3/H)FSBA was covalently bound to TH, and complete inhibition corresponded to the binding of about 0.5 mol of (3H)FSBA/mol of TH. Since purified TH is known to be dimeric in the isolated state, this binding stoichiometry suggests half-of-the-sites reactivity. A similar binding stoichiometry was found earlier for complete inhibition of TH by (/sup 14/C)DCCD. The active site directed labeling of TH by radioactive FSBA should allow isolation of appropriate peptides for sequence analysis of the NAD(H) and possibly the NADP(H) binding domains.

  2. Identification and characterization of the tungsten-containing class of benzoyl-coenzyme A reductases.

    PubMed

    Kung, Johannes W; Löffler, Claudia; Dörner, Katerina; Heintz, Dimitri; Gallien, Sébastien; Van Dorsselaer, Alain; Friedrich, Thorsten; Boll, Matthias

    2009-10-20

    Aromatic compounds are widely distributed in nature and can only be biomineralized by microorganisms. In anaerobic bacteria, benzoyl-CoA (BCoA) is a central intermediate of aromatic degradation, and serves as substrate for dearomatizing BCoA reductases (BCRs). In facultative anaerobes, the mechanistically difficult reduction of BCoA to cyclohexa-1,5-dienoyl-1-carboxyl-CoA (dienoyl-CoA) is driven by a stoichiometric ATP hydrolysis, catalyzed by a soluble, three [4Fe-4S] cluster-containing BCR. In this work, an in vitro assay for BCR from the obligately anaerobic Geobacter metallireducens was established. It followed the reverse reaction, the formation of BCoA from dienoyl-CoA in the presence of various electron acceptors. The benzoate-induced activity was highly specific for dienoyl-CoA (K(m) = 24 +/- 4 microM). The corresponding oxygen-sensitive enzyme was purified by several chromatographic steps with a 115-fold enrichment and a yield of 18%. The 185-kDa enzyme comprised 73- and 20-kDa subunits, suggesting an alpha(2)beta(2)-composition. MS analysis revealed the subunits as products of the benzoate-induced bamBC genes. The alphabeta unit contained 0.9 W, 15 Fe, and 12.5 acid-labile sulfur. Results from EPR spectroscopy suggest the presence of one [3Fe-4S](0/+1) and three [4Fe-4S](+1/+2) clusters per alphabeta unit; oxidized BamBC exhibited an EPR signal typical for a W(V) species. The FeS clusters and the W- cofactor could only be fully reduced by dienoyl-CoA. BamBC represents the prototype of a previously undescribed class of dearomatizing BCRs that differ completely from the ATP-dependent enzymes from facultative anaerobes.

  3. Efficacy of the addition of salicylic acid to clindamycin and benzoyl peroxide combination for acne vulgaris.

    PubMed

    Akarsu, Sevgi; Fetil, Emel; Yücel, Filiz; Gül, Eylem; Güneş, Ali T

    2012-05-01

    Clindamycin phosphate (CDP), benzoyl peroxide (BPO) and salicylic acid (SA) are known to be effective acne therapy agents depending on their anti-inflammatory and comedolytic properties. The purpose of this study was to investigate the efficacy and tolerability of the addition of SA treatment to CDP and BPO (SA and CDP + BPO) and compare it with CDP + BPO in patients with mild to moderate facial acne vulgaris. Forty-nine patients were enrolled in a 12 week prospective, single-blind, randomized, comparative clinical study. Efficacy was assessed by lesion counts, global improvement, quality of life index and measurements of skin barrier functions. Local side effects were also evaluated. Both combinations were effective in reducing total lesion (TL), inflammatory lesion (IL) and non-inflammatory lesion (NIL) counts. There were statistically significant differences between treatment groups for reductions in NIL counts beyond 2 weeks, IL counts and TL counts throughout the all study weeks, and global improvement scores evaluated by patients and investigator at the end of the study in favor of SA and CDP + BPO treatment when compared to CDP + BPO treatment. Both combinations significantly decreased stratum corneum hydration, although skin sebum values decreased with SA and CDP + BPO treatment. These combinations were also well tolerated except significantly higher frequency of mild to moderate transient dryness in patients applied SA and CDP + BPO. The addition of SA to CDP + BPO treatment demonstrated significantly better and faster results in terms of reductions in acne lesion counts and well tolerated except for higher frequency of mild to moderate transient dryness.

  4. A New, Once-daily, Optimized, Fixed Combination of Clindamycin Phosphate 1.2% and Low-concentration Benzoyl Peroxide 2.5% Gel for the Treatment of Moderate-to-Severe Acne.

    PubMed

    Gold, Michael H

    2009-05-01

    The treatment of acne with combination therapy is commonplace with treatment aimed at sustained efficacy with minimal side effects, maximum adherence, and the avoidance of bacterial resistance. Combinations containing clindamycin and benzoyl peroxide have been shown to be effective, but the irritation caused by the concentration of benzoyl peroxide 5% in the more commonly used, fixed combinations can be limiting. In addition, surfactants, preservatives, and high levels of organic solvents, including alcohols, often used in combination with benzoyl peroxide, are potential irritants. An optimized formulation of clindamycin and benzoyl peroxide using a lower concentration of benzoyl peroxide (clindamycin-benzoyl peroxide 2.5% gel) has been developed without the use of surfactants or alcohol. It was recently introduced for the once-daily treatment of inflammatory and noninflammatory lesions in moderate-to-severe acne. Following a clinical program that studied more than 2,800 patients, clindamycin-benzoyl peroxide 2.5% was found to be highly effective and well tolerated. This review highlights the development of clindamycin-benzoyl peroxide 2.5% gel and the data from clinical trials.(J Clin Aesthetic Dermatol. 2009;2(5):44-48.). PMID:20729964

  5. An efficient combination of Zr-MOF and microwave irradiation in catalytic Lewis acid Friedel-Crafts benzoylation.

    PubMed

    Doan, Tan L H; Dao, Thong Q; Tran, Hai N; Tran, Phuong H; Le, Thach N

    2016-05-01

    A zirconium-based metal-organic framework, an effective heterogeneous catalyst, has been developed for the Friedel-Crafts benzoylation of aromatic compounds under microwave irradiation. Constructed by a Zr(iv) cluster and a linker 1,4-bis(2-[4-carboxyphenyl]ethynyl)benzene (H2CPEB), the MOF, possessing large pores and high chemical stability, was appropriate for the enhancement of Lewis acid activity under microwave irradiation. The reaction studies demonstrated that the material could give high yields for a few minutes and maintain its reactivity and structure over several cycles. PMID:27064371

  6. Evaluating clinical trial design: systematic review of randomized vehicle-controlled trials for determining efficacy of benzoyl peroxide topical therapy for acne.

    PubMed

    Lamel, Sonia A; Sivamani, Raja K; Rahvar, Maral; Maibach, Howard I

    2015-11-01

    Determined efficacies of benzoyl peroxide may be affected by study design, implementation, and vehicle effects. We sought to elucidate areas that may allow improvement in determining accurate treatment efficacies by determining rates of active treatment and vehicle responders in randomized controlled trials assessing the efficacy of topical benzoyl peroxide to treat acne. We conducted a systematic review of randomized vehicle-controlled trials evaluating the efficacy of topical benzoyl peroxide for the treatment of acne. We compared response rates of vehicle treatment arms versus those in benzoyl peroxide arms. Twelve trials met inclusion criteria with 2818 patients receiving benzoyl peroxide monotherapy treatment and 2004 receiving vehicle treatment. The average percent reduction in total number of acne lesions was 44.3 (SD = 9.2) and 27.8 (SD = 21.0) for the active and vehicle treatment groups, respectively. The average reduction in non-inflammatory lesions was 41.5 % (SD = 9.4) in the active treatment group and 27.0 % (SD = 20.9) in the vehicle group. The average percent decrease in inflammatory lesions was 52.1 (SD = 10.4) in the benzoyl peroxide group and 34.7 (SD = 22.7) in the vehicle group. The average percentage of participants achieving success per designated study outcomes was 28.6 (SD = 17.3) and 15.2 (SD = 9.5) in the active treatment and vehicle groups, respectively. Patient responses in randomized controlled trials evaluating topical acne therapies may be affected by clinical trial design, implementation, the biologic effects of vehicles, and natural disease progression. "No treatment" groups may facilitate determination of accurate treatment efficacies.

  7. Evaluating clinical trial design: systematic review of randomized vehicle-controlled trials for determining efficacy of benzoyl peroxide topical therapy for acne.

    PubMed

    Lamel, Sonia A; Sivamani, Raja K; Rahvar, Maral; Maibach, Howard I

    2015-11-01

    Determined efficacies of benzoyl peroxide may be affected by study design, implementation, and vehicle effects. We sought to elucidate areas that may allow improvement in determining accurate treatment efficacies by determining rates of active treatment and vehicle responders in randomized controlled trials assessing the efficacy of topical benzoyl peroxide to treat acne. We conducted a systematic review of randomized vehicle-controlled trials evaluating the efficacy of topical benzoyl peroxide for the treatment of acne. We compared response rates of vehicle treatment arms versus those in benzoyl peroxide arms. Twelve trials met inclusion criteria with 2818 patients receiving benzoyl peroxide monotherapy treatment and 2004 receiving vehicle treatment. The average percent reduction in total number of acne lesions was 44.3 (SD = 9.2) and 27.8 (SD = 21.0) for the active and vehicle treatment groups, respectively. The average reduction in non-inflammatory lesions was 41.5 % (SD = 9.4) in the active treatment group and 27.0 % (SD = 20.9) in the vehicle group. The average percent decrease in inflammatory lesions was 52.1 (SD = 10.4) in the benzoyl peroxide group and 34.7 (SD = 22.7) in the vehicle group. The average percentage of participants achieving success per designated study outcomes was 28.6 (SD = 17.3) and 15.2 (SD = 9.5) in the active treatment and vehicle groups, respectively. Patient responses in randomized controlled trials evaluating topical acne therapies may be affected by clinical trial design, implementation, the biologic effects of vehicles, and natural disease progression. "No treatment" groups may facilitate determination of accurate treatment efficacies. PMID:26048131

  8. Chemical stability of adapalene and tretinoin when combined with benzoyl peroxide in presence and in absence of visible light and ultraviolet radiation.

    PubMed

    Martin, B; Meunier, C; Montels, D; Watts, O

    1998-10-01

    Adapalene and tretinoin are molecules used in the topical treatment of acne vulgaris. Commercial formulations (adapalene 0.1% gel and tretinoin 0.025% gel) were mixed with equal volumes of commercially available benzoyl peroxide formulation (10% lotion) and subsequently exposed to light over 24 h. With and without exposition to light, adapalene exhibits a remarkable stability whereas tretinoin is very sensitive to light and oxidation. The combination of benzoyl peroxide and light results in more than 50% degradation of tretinoin in about 2 h and 95% in 24 h.

  9. Substitution Effects and Linear Free Energy Relationships During Reduction of 4- Benzoyl-n-(4-substituted Benzyl)pyridinium Cations

    NASA Technical Reports Server (NTRS)

    Leventis, Nicholas; Zhang, Guo-Hui; Rawashdeh, Abdel-Monem M.; Sotiriou-Leventis, Chariklia; Gray, Hugh R. (Technical Monitor)

    2003-01-01

    In analogy to 4-(para-substituted benzoyl)-N-methylpyridinium cations (1-X's), the title species (2-X's, -X = -OCH3, -CH3, -H, -Br, -COCH3, -NO2) undergo two reversible, well-separated (E(sub 1/2) greater than or equal to 650 mV) one-electron reductions. The effect of substitution on the reduction potentials of 2-X's is much weaker than the effect of the same substituents on 1-X's: the Hammett rho-values are 0.80 and 0.93 for the 1st- and 2nd-e reduction of 2-X's vs. 2.3 and 3.3 for the same reductions of 1-X's, respectively. Importantly, the nitro group of 2-NO2 undergoes reduction before the 2nd-e reduction of the 4-benzoylpyridinium system. These results suggest that the redox potentials of the 4-benzoylpyridinium system can be course-tuned via p-benzoyl substitution and fine-tuned via para-benzyl substitution. Introducing the recently derived substituent constant of the -NO2(sup)- group (sigma para-NO2(sup)- = -0.97) yields an excellent correlation for the 3rd-e reduction of 2- NO2 (corresponding to the reduction of the carbonyl group) with the 2nd-e reduction of the other 2-X's, and confirms the electron donating properties of -NO2(sup)-.

  10. Structure and Function of the Unusual Tungsten Enzymes Acetylene Hydratase and Class II Benzoyl-Coenzyme A Reductase.

    PubMed

    Boll, Matthias; Einsle, Oliver; Ermler, Ulrich; Kroneck, Peter M H; Ullmann, G Matthias

    2016-01-01

    In biology, tungsten (W) is exclusively found in microbial enzymes bound to a bis-pyranopterin cofactor (bis-WPT). Previously known W enzymes catalyze redox oxo/hydroxyl transfer reactions by directly coordinating their substrates or products to the metal. They comprise the W-containing formate/formylmethanofuran dehydrogenases belonging to the dimethyl sulfoxide reductase (DMSOR) family and the aldehyde:ferredoxin oxidoreductase (AOR) families, which form a separate enzyme family within the Mo/W enzymes. In the last decade, initial insights into the structure and function of two unprecedented W enzymes were obtained: the acetaldehyde forming acetylene hydratase (ACH) belongs to the DMSOR and the class II benzoyl-coenzyme A (CoA) reductase (BCR) to the AOR family. The latter catalyzes the reductive dearomatization of benzoyl-CoA to a cyclic diene. Both are key enzymes in the degradation of acetylene (ACH) or aromatic compounds (BCR) in strictly anaerobic bacteria. They are unusual in either catalyzing a nonredox reaction (ACH) or a redox reaction without coordinating the substrate or product to the metal (BCR). In organic chemical synthesis, analogous reactions require totally nonphysiological conditions depending on Hg2+ (acetylene hydration) or alkali metals (benzene ring reduction). The structural insights obtained pave the way for biological or biomimetic approaches to basic reactions in organic chemistry.

  11. Stability of benzoyl peroxide in aromatic ester-containing topical formulations.

    PubMed

    Majekodunmi, Bola D; Lau-Cam, Cesar A; Nash, Robert A

    2007-01-01

    The chemical stability of benzoyl peroxide (BPO) was studied in solutions and gels. The solutions (1% w/v) were prepared in single solvents (alcohol USP, isopropyl alcohol USP, ethyl benzoate, C12-15 alkyl benzoate, dimethyl isosorbide, propylene carbonate, and acetone) and in binary and tertiary combinations of these solvents, with and without the addition of antioxidant(s) (BHT, BHA, eugenol, tert-butyl hydroquinone, Tenox-2, vitamin E, and vitamin C). The solutions were stored at 37 degrees C for 5 weeks, and each week were analyzed for remaining BPO. Using first-order kinetics, the stability of BPO in solution was found to decrease in the order: ternary>binary>single solvent systems. Regardless of the number of solvents present, the highest stability of BPO (t1/2>7.5 weeks) was attained in the presence of ethyl benzoate and C12-15 alkyl benzoate. The stability of BPO in solution did not change significantly with the addition of most antioxidants. The solutions in which BPO remained most stable were one in alcohol USP-ethyl benzoate-C12-15 alkyl benzoate (60:20:20; t1/2=18.15 weeks) and another in alcohol USP-C12-15 alkyl benzoate-isopropanol plus 0.1% BHT (65:20:15; t1/2=12.44 weeks). In turn, these two solutions were converted to homogeneous gels by the addition of Cab-O-Sil. The chemical stability of BPO in these gels was evaluated at 37 degrees, 45 degrees, 50 degrees, and 55 degrees C for 5 weeks. Parallel experiments were conducted with two commercial BPO products, a 2.5% tinted gel and 5% vanishing lotion. BPO was less stable in commercial products (t1/2

  12. Randomized, Observer-blind, Split-face Compatibility Study with Clindamycin Phosphate 1.2%/Benzoyl Peroxide 3.75% gel and Facial Foundation Makeup

    PubMed Central

    Pillai, Radhakrishnan

    2015-01-01

    Background: Cosmetic compatibility in the treatment of acne is an important issue significantly impacting quality of life, but often overlooked, as dermatologists commonly recommended avoidance of cosmetic foundations when treating adult female patients. Fixed combinations of clindamycin/benzoyl peroxide are widely used in the treatment of acne, but little is known about the impact of their concomitant use with facial foundation. Objective: To assess the compatibility of clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel with foundation makeup for up to six hours after application. Methods: Twenty-nine female subjects applied makeup to their face after randomly applying clindamycin phosphate 1. 2%/benzoyl peroxide 3. 75% gel to one side of the face. Investigator and subject self- assessment included facial skin attributes, facial tolerability, and cosmetic compatibility post-application and at Hour 6; as well as cutaneous tolerability. Results: No statistical difference was noted between the treated and untreated side of the face in terms of coverage, blotchiness, appearance, skin tone, or visual smoothness. Tolerability was excellent, with no erythema, edema, dryness, and peeling post-makeup application. For both the treated and untreated side, there was a slight lack of improvement in cosmetic appearance six hours post-makeup application. Conclusion: Clindamycin/benzoyl peroxide 3. 75% gel was shown to have excellent cosmetic compatibility with facial foundation. PMID:26430488

  13. Benzoylation of Ergosterol through Nucleophilic Acyl Substitution and Subsequent Formation of Ergosterol Benzoate Endoperoxide by Reaction with Singlet Oxygen Generated by Photosensitization

    ERIC Educational Resources Information Center

    Roslaniec, Mary C.; Sanford, Elizabeth M.

    2011-01-01

    Reactive oxygen species such as singlet oxygen have been a major focus of research in medicine. The effect of singlet oxygen on sterols within biological membranes is becoming increasingly more important. Ergosterol, a vitamin D precursor, is one such sterol. The benzoylation of ergosterol and subsequent reaction with singlet oxygen to form an…

  14. Entropy-controlled supramolecular photochirogenesis: enantiodifferentiating Z-E photoisomerization of cyclooctene included and sensitized by permethylated 6-O-benzoyl-beta-cyclodextrin.

    PubMed

    Fukuhara, Gaku; Mori, Tadashi; Wada, Takehiko; Inoue, Yoshihisa

    2005-09-01

    In contrast to the photosensitization with a non-methylated analogue, supramolecular photochirogenesis with a novel permethylated mono(6-O-benzoyl)-beta-cyclodextrin exhibited a critical dependence of the product's enantiomeric excess upon temperature, and possessed a large differential entropy of activation (-11 J K(-1) mol(-1)) for which the flexible host skeleton is likely to be responsible.

  15. Effect of temperature and concentration on benzoyl peroxide bleaching efficacy and benzoic acid levels in whey protein concentrate.

    PubMed

    Smith, T J; Gerard, P D; Drake, M A

    2015-11-01

    Much of the fluid whey produced in the United States is a by-product of Cheddar cheese manufacture and must be bleached. Benzoyl peroxide (BP) is currently 1 of only 2 legal chemical bleaching agents for fluid whey in the United States, but benzoic acid is an unavoidable by-product of BP bleaching. Benzoyl peroxide is typically a powder, but new liquid BP dispersions are available. A greater understanding of the bleaching characteristics of BP is necessary. The objective of the study was to compare norbixin destruction, residual benzoic acid, and flavor differences between liquid whey and 80% whey protein concentrates (WPC80) bleached at different temperatures with 2 different benzoyl peroxides (soluble and insoluble). Two experiments were conducted in this study. For experiment 1, 3 factors (temperature, bleach type, bleach concentration) were evaluated for norbixin destruction using a response surface model-central composite design in liquid whey. For experiment 2, norbixin concentration, residual benzoic acid, and flavor differences were explored in WPC80 from whey bleached by the 2 commercially available BP (soluble and insoluble) at 5 mg/kg. In liquid whey, soluble BP bleached more norbixin than insoluble BP, especially at lower concentrations (5 and 10 mg/kg) at both cold (4°C) and hot (50°C) temperatures. The WPC80 from liquid whey bleached with BP at 50°C had lower norbixin concentration, benzoic acid levels, cardboard flavor, and aldehyde levels than WPC80 from liquid whey bleached with BP at 4°C. Regardless of temperature, soluble BP destroyed more norbixin at lower concentrations than insoluble BP. The WPC80 from soluble-BP-bleached wheys had lower cardboard flavor and lower aldehyde levels than WPC80 from insoluble-BP-bleached whey. This study suggests that new, soluble (liquid) BP can be used at lower concentrations than insoluble BP to achieve equivalent bleaching and that less residual benzoic acid remains in WPC80 powder from liquid whey

  16. Effect of temperature and concentration on benzoyl peroxide bleaching efficacy and benzoic acid levels in whey protein concentrate.

    PubMed

    Smith, T J; Gerard, P D; Drake, M A

    2015-11-01

    Much of the fluid whey produced in the United States is a by-product of Cheddar cheese manufacture and must be bleached. Benzoyl peroxide (BP) is currently 1 of only 2 legal chemical bleaching agents for fluid whey in the United States, but benzoic acid is an unavoidable by-product of BP bleaching. Benzoyl peroxide is typically a powder, but new liquid BP dispersions are available. A greater understanding of the bleaching characteristics of BP is necessary. The objective of the study was to compare norbixin destruction, residual benzoic acid, and flavor differences between liquid whey and 80% whey protein concentrates (WPC80) bleached at different temperatures with 2 different benzoyl peroxides (soluble and insoluble). Two experiments were conducted in this study. For experiment 1, 3 factors (temperature, bleach type, bleach concentration) were evaluated for norbixin destruction using a response surface model-central composite design in liquid whey. For experiment 2, norbixin concentration, residual benzoic acid, and flavor differences were explored in WPC80 from whey bleached by the 2 commercially available BP (soluble and insoluble) at 5 mg/kg. In liquid whey, soluble BP bleached more norbixin than insoluble BP, especially at lower concentrations (5 and 10 mg/kg) at both cold (4°C) and hot (50°C) temperatures. The WPC80 from liquid whey bleached with BP at 50°C had lower norbixin concentration, benzoic acid levels, cardboard flavor, and aldehyde levels than WPC80 from liquid whey bleached with BP at 4°C. Regardless of temperature, soluble BP destroyed more norbixin at lower concentrations than insoluble BP. The WPC80 from soluble-BP-bleached wheys had lower cardboard flavor and lower aldehyde levels than WPC80 from insoluble-BP-bleached whey. This study suggests that new, soluble (liquid) BP can be used at lower concentrations than insoluble BP to achieve equivalent bleaching and that less residual benzoic acid remains in WPC80 powder from liquid whey

  17. The potential of iron chelators of the pyridoxal isonicotinoyl hydrazone class as effective antiproliferative agents II: the mechanism of action of ligands derived from salicylaldehyde benzoyl hydrazone and 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone.

    PubMed

    Richardson, D R; Milnes, K

    1997-04-15

    We have recently screened 36 analogues of the lipophilic iron (Fe) chelator, pyridoxal isonicotinoyl hydrazone (PIH), for their antiproliferative effect (Richardson et al, Blood 86:4295, 1995). Of these compounds, 1 chelator derived from salicylaldehyde benzoyl hydrazone (206) and 4 ligands derived from 2-hydroxy-1-naphthylaldehyde benzoyl hydrazone (308, 309, 311, and 315) showed pronounced antiproliferative activity, being far more effective than desferrioxamine (DFO). The present study was designed to investigate in detail the mechanism of action of these PIH analogues in a variety of neoplastic cell lines. This investigation showed that the analogues were far more active than DFO at inhibiting cellular proliferation and 3H-thymidine, 3H-leucine, and 3H-uridine incorporation. Additional experiments showed that, in contrast to DFO, the 5 analogues were potent at preventing 59Fe uptake from transferrin (Tf) and increasing 59Fe release from cells at concentrations as low as 10 micromol/L. Examination of the distribution of 59Fe in neoplastic cells using native polyacrylamide gel electrophoresis (PAGE)/59Fe-autoradiography showed that most of the 59Fe taken up from Tf was incorporated into ferritin, although 3 other previously unrecognized components (bands A, B, and C) were also identified. Band C comigrated with 59Fe-citrate and was chelated on incubation of neuroblastoma cells with DFO, PIH, or the PIH analogues, with this compartment being the main intracellular target of these ligands. Further work showed that the effects of the chelators at inducing characteristics consistent with apoptosis or necrosis were cell line-specific, and while DFO increased the percentage of cells in the G0/G1 phases in all cell types, the effect of analogue 311 on the cell cycle was variable depending on the cell line. This study provides further evidence for the potential use of these Fe chelators as anticancer agents.

  18. Evaluation of paclitaxel rearrangement involving opening of the oxetane ring and migration of acetyl and benzoyl groups.

    PubMed

    Pyo, Sang-Hyun; Cho, Jin-Suk; Choi, Ho-Joon; Han, Byung-Hee

    2007-02-19

    The stability of drug is a critical factor in quality control, drug efficacy, safety, storage, and production conditions. The rearrangement of paclitaxel, which involves opening of the oxetane ring and migration of acetyl group occurred on heating a powder of purified paclitaxel. Subsequently, the unusual migration of benzoyl groups progressed rapidly in organic solvents. These rearrangement derivatives were isolated carefully. The structures of the intermediate derivative A and the product derivative B were confirmed using (1)H NMR, high performance liquid chromatography (HPLC), and mass spectrometry. We proposed the rearrangement pathway here for the first time. Neither derivative exhibited bioactivity in SKOV3 (ovarian cancer) or MDA-MB-435 (breast cancer) cell culture assays.

  19. Do tutorials on application method enhance adapalene-benzoyl peroxide combination gel tolerability in the treatment of acne?

    PubMed

    Kwon, Hyuck Hoon; Park, Seon Yong; Yoon, Ji Young; Min, Seonguk; Suh, Dae Hun

    2015-11-01

    Fixed-dose combination adapalene 0.1% and benzoyl peroxide 2.5% gel (A-BPO) has rarely been studied for Asian acne patients, while they have complained of local irritations more often when applying individual components. In this study, we compared A-BPO gel with benzoyl peroxide (BPO) in terms of efficacy and tolerability in Korean patients first, and assessed the clinical benefit of a dermatological tutorial on application technique in reducing irritations for A-BPO. This study was conducted as a single-blind controlled split-face trial for a 12-week period. Each half facial side of 85 patients was randomly assigned to either A-BPO or BPO. Success rate, lesion counts and safety profiles were evaluated (analysis I). During initial assignment, all patients were further randomized to either dermatological tutorial (DT) or non-tutorial (NT) subgroups depending on the presence of dermatologists' tutorials for application methods to their A-BPO sides. Clinical data of the A-BPO side was compared between two subgroups (analysis II). As a result, A-BPO gel outperformed BPO, demonstrating better efficacy in success rates and lesion counts as early as 1 week. However, A-BPO proved significantly less tolerable compared with both BPO and previous A-BPO data from Caucasians. Bioengineering measurements further confirmed clinical data (analysis I). The DT subgroup achieved much better tolerability with comparable therapeutic efficacies compared with the NT subgroup (analysis II). In conclusion, A-BPO demonstrated higher efficacies in acne compared with BPO in Korean patients, while skin irritation levels were notable concurrently. Dermatologists' education for application methods would significantly decrease these side-effects, maintaining superior efficacy levels.

  20. Analytical studies of the interaction of Tb(III)-2-{[(4-methoxy benzoyl) oxy]} methyl benzoic acid binary complex with nucleosides

    NASA Astrophysics Data System (ADS)

    Shehata, A. M. A.; Azab, H. A.; El-assy, N. B.; Anwar, Z. M.; Mostafa, H. M.

    2016-01-01

    The interaction of Tb(III)-2-{[(4-methoxy benzoyl) oxy]} methyl benzoic acid binary complex with nucleosides (adenosine, cytidine, guanosine and inosine) was investigated using UV and fluorescence methods. The reaction of Tb-complex with cytidine, guanosine and adenosine is accompanied by shift to longer wavelength in the absorption band, while there is a blue shift in the absorption band with an enhancement in the molar absorptivity upon the reaction with inosine. The fluorescence intensity of Tb(III)-2-{[(4- methoxy benzoyl) oxy]} methyl benzoic acid binary complex at λ = 545 nm (5D4 → 7F5) was decreased with the addition of the nucleoside molecule following the order: cytidine > inosine > guanosine > adenosine.

  1. Cutaneous Safety and Tolerability of a Fixed Combination Clindamycin (1.2%) and Benzoyl Peroxide (3.75%) Aqueous Gel in Moderate-to-severe Acne Vulgaris

    PubMed Central

    2015-01-01

    Objective: To investigate the cutaneous safety and tolerability of clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel in moderate-to-severe acne patients. Methods: A safety assessment of 498 patients with moderate-to-severe acne receiving clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel or vehicle for 12 weeks. Results: The vast majority (80-95%) of patients reported no cutaneous safety or tolerability problems throughout the study. Mean scores for both active and vehicle were all <1 (where l=mild) and reduced over the duration of the study. When scaling, erythema, itching, burning, or stinging was reported it was generally mild. Moderate or severe reactions to clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel were rare and generally seen early in treatment. There were eight reports (3.3%) of moderate erythema, four reports (1.7%) of moderate scaling, three reports (1.2%) of moderate itching, and one report of moderate burning (0.4%) at Week 4. There was one report (0.4%) of severe erythema and one report (0.4%) of severe burning (both at Week 4), with one report (0.4%) of severe stinging at Week 12. There were no substantive differences seen in cutaneous tolerability among treatment groups and younger patients tended to have milder reactions. Limitations: It is not possible to determine the contributions of the individual active ingredients. Conclusion: Clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel has a favorable safety and tolerability profile with very low incidence of moderate or severe reactions. PMID:26345297

  2. Efficacy and Tolerability of a Fixed Combination of Clindamycin Phosphate (1.2%) and Benzoyl Peroxide (3.75%) Aqueous Gel in Moderate or Severe Adolescent Acne Vulgaris

    PubMed Central

    2015-01-01

    Background: Acne is commonplace in adolescents and can be difficult to manage. Providing an effective and well-tolerated treatment may lead to improved adherence, increased patient satisfaction, and improved clinical outcomes. Methods: A post hoc analysis of efficacy and cutaneous tolerability in 289 adolescents (age range, 12 to <18 years) with moderate-to-severe acne who had been enrolled in a multicenter study and were randomized to receive either clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel or vehicle once daily for 12 weeks. Results: Significantly superior reductions in lesion counts were observed in the clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel group compared to vehicle from Week 4, with mean percent reductions in inflammatory and noninflammatory lesions from baseline of 59.9 percent and 50.5 percent, respectively (both P<0.001 versus vehicle). One-third of patients treated with clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel achieved ≥2-grade improvement from baseline in their Evaluator’s Global Severity Score (compared to 8.5% with vehicle, P<0.001) and 35 percent of patients reported clear or almost clear skin at Week 12 (compared to 12.8% with vehicle, P<0.001). Cutaneous tolerability was excellent with all mean scores ≤0.2 at Week 12 (where 1=mild). Conclusions: Clindamycin phosphate 1.2%/benzoyl peroxide 3.75% gel is an effective, safe, well-tolerated treatment for adolescents with moderate-to-severe acne. PMID:26029332

  3. Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity

    NASA Astrophysics Data System (ADS)

    Odame, Felix; Hosten, Eric C.; Betz, Richard; Lobb, Kevin; Tshentu, Zenixole R.

    2015-11-01

    The reaction of benzoyl isothiocyanate with L-serine, L-proline, D-methionine and L-alanine gave 2-[(benzoylcarbamothioyl)amino]-3-hydroxypropanoic acid (I), 1-(benzoylcarbamothioyl)pyrrolidine-2-carboxylic acid (II), 2-[(benzoylcarbamothioyl)amino]-4-(methylsulfanyl)butanoic acid (III) and 2-[(benzoylcarbamothioyl)amino]propanoic acid (IV), respectively. The compounds have been characterized by IR, NMR, microanalyses and mass spectrometry. The crystal structures of all the compounds have also been discussed. Compound II showed rotamers in solution. DFT calculations of the frontier orbitals of the compounds have been carried out to ascertain the groups that contribute to the HOMO and LUMO, and to study their contribution to the reactivity of these compounds. The calculations indicated that the carboxylic acid group in these compounds is unreactive hence making the conversion to benzimidazoles via cyclization on the carboxylic acids impractical. This has been further confirmed by the reaction of compounds I-IV, respectively, with o-phenylene diamine which was unsuccessful but gave compound V.

  4. Topical therapy for acne in women: is there a role for clindamycin phosphate-benzoyl peroxide gel?

    PubMed

    Del Rosso, James Q

    2014-10-01

    Acne vulgaris (AV) in adult women is commonly encountered in clinical dermatology practice. This patient subset often experiences psychosocial effects that differ in some ways from those experienced by adolescent females with AV, as they were not expecting to have to deal with this disorder beyond their adolescent years. Most of the emphasis on therapy for adult women with AV has focused on use of oral contraceptives (OCs) and/or oral spironolactone, with little to no evaluation or discussion of topical agents in this patient group. This article provides an overview of AV in adult women and presents the results of a subanalysis of data from female patients who were treated in phase 3 studies with clindamycin phosphate (CP) 1.2%-benzoyl peroxide (BP) 2.5% gel once daily for facial AV. The subanalysis compared outcomes in females younger than 25 years and in those 25 years and older. Overall, the data showed that therapeutic outcomes were comparable between the 2 groups.

  5. Establishment of an activated peroxide system for low-temperature cotton bleaching using N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride.

    PubMed

    Xu, Changhai; Hinks, David; Sun, Chang; Wei, Qufu

    2015-03-30

    Cotton bleaching is traditionally carried out in strongly alkaline solution of hydrogen peroxide (H2O2) at temperatures close to the boil. Such harsh processing conditions can result in extensive water and energy consumptions as well as severe chemical damage to textiles. In this study, an activated peroxide system was established for low-temperature cotton bleaching by incorporating a bleach activator, namely N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride (TBBC) into an aqueous H2O2 solution. Experimental results showed that the TBBC-activated peroxide system exhibited the most effective bleaching performance in a pH range of 6-8 which could be approximated by adding sodium bicarbonate (NaHCO3). The TBBC/H2O2/NaHCO3 system led to rapid bleaching of cotton at a temperature as low as 50°C. In comparison with the hot alkaline peroxide bleaching system, the TBBC/H2O2/NaHCO3 system provided cotton fabric with an equivalent degree of whiteness, higher degree of polymerization, and slightly lower water absorbency. The new activated peroxide system may provide a more environmentally benign approach to cotton bleaching.

  6. Inactivation of Escherichia coli glycerol kinase by 5'-(p-(fluorosulfonyl)benzoyl))adenosine: protection by the hydrolyzed reagent

    SciTech Connect

    Pettigrew, D.W.

    1987-03-24

    Incubation of Escherichia coli glycerol kinase with 5'-(p-(fluorosulfonyl)benzoyl)adenosine (FSO/sub 2/BzAdo) at pH 8.0 and 25/sup 0/C results in the loss of enzyme activity, which is not restored by the addition of ..beta..-mercaptoethanol or dithiothreitol. The FSO/sub 2/BzAdo concentration dependence of the inactivation kinetics is described by a mechanism that includes the equilibrium binding of the reagent to the enzyme prior to a first-order inactivation reaction in addition to effects of reagent hydrolysis. The hydrolysis of the reagent has two effects on the observed kinetics. The first effect is deviation from pseudo-first-order kinetic behavior due to depletion of the reagent. The second effect is the novel protection of the enzyme from inactivation due to binding of the sulfonate hydrolysis product. Determinations of the reaction stoichiometry with /sup 3/H-labeled FSO/sub 2/BzAdo show that the inactivation is associated with the covalent incorporation of 1.08 mol of reagent/mol of enzyme subunit. Ligand protection experiments show that ATP, AMP, dAMP, NADH, 5'-adenylyl imidodiphosphate, and the sulfonate hydrolysis product of FSO/sub 2/BzAdo provide protection from inactivation. The protection obtained with ATMP is not dependent on Mg/sup 2 +/. The results are consistent with modification by FSO/sub 2/BzAdo of a single adenine nucleotide binding site per enzyme subunit.

  7. HIV-1 Reverse Transcriptase Structure with RNase H Inhibitor dihydroxy benzoyl naphthyl Hydrazone Bound at a Novel Site

    SciTech Connect

    Himmel,D.; Sarafianos, S.; Dharmasena, S.; Hossain, M.; McCoy-Simandle, K.; Ilina, T.; Clark, A.; Knight, J.; Julias, J.; et al.

    2007-01-01

    The rapid emergence of drug-resistant variants of human immunodeficiency virus, type 1 (HIV-1), has limited the efficacy of anti-acquired immune deficiency syndrome (AIDS) treatments, and new lead compounds that target novel binding sites are needed. We have determined the 3.15 {angstrom} resolution crystal structure of HIV-1 reverse transcriptase (RT) complexed with dihydroxy benzoyl naphthyl hydrazone (DHBNH), an HIV-1 RT RNase H (RNH) inhibitor (RNHI). DHBNH is effective against a variety of drug-resistant HIV-1 RT mutants. While DHBNH has little effect on most aspects of RT-catalyzed DNA synthesis, at relatively high concentrations it does inhibit the initiation of RNA-primed DNA synthesis. Although primarily an RNHI, DHBNH binds >50 {angstrom} away from the RNH active site, at a novel site near both the polymerase active site and the non-nucleoside RT inhibitor (NNRTI) binding pocket. When DHBNH binds, both Tyr181 and Tyr188 remain in the conformations seen in unliganded HIV-1 RT. DHBNH interacts with conserved residues (Asp186, Trp229) and has substantial interactions with the backbones of several less well-conserved residues. On the basis of this structure, we designed substituted DHBNH derivatives that interact with the NNRTI-binding pocket. These compounds inhibit both the polymerase and RNH activities of RT.

  8. Establishment of an activated peroxide system for low-temperature cotton bleaching using N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride.

    PubMed

    Xu, Changhai; Hinks, David; Sun, Chang; Wei, Qufu

    2015-03-30

    Cotton bleaching is traditionally carried out in strongly alkaline solution of hydrogen peroxide (H2O2) at temperatures close to the boil. Such harsh processing conditions can result in extensive water and energy consumptions as well as severe chemical damage to textiles. In this study, an activated peroxide system was established for low-temperature cotton bleaching by incorporating a bleach activator, namely N-[4-(triethylammoniomethyl)benzoyl]butyrolactam chloride (TBBC) into an aqueous H2O2 solution. Experimental results showed that the TBBC-activated peroxide system exhibited the most effective bleaching performance in a pH range of 6-8 which could be approximated by adding sodium bicarbonate (NaHCO3). The TBBC/H2O2/NaHCO3 system led to rapid bleaching of cotton at a temperature as low as 50°C. In comparison with the hot alkaline peroxide bleaching system, the TBBC/H2O2/NaHCO3 system provided cotton fabric with an equivalent degree of whiteness, higher degree of polymerization, and slightly lower water absorbency. The new activated peroxide system may provide a more environmentally benign approach to cotton bleaching. PMID:25563946

  9. Design, synthesis and biological evaluation of 4-benzoyl-1-dichlorobenzoylthiosemicarbazides as potent Gram-positive antibacterial agents.

    PubMed

    Paneth, Agata; Plech, Tomasz; Kaproń, Barbara; Hagel, Dominika; Kosikowska, Urszula; Kuśmierz, Edyta; Dzitko, Katarzyna; Paneth, Piotr

    2016-01-01

    Twelve 4-benzoyl-1-dichlorobenzoylthiosemicarbazides have been tested as potential antibacterials. All the compounds had MICs between 0.49 and 15.63 µg/ml toward Micrococcus luteus, Bacillus cereus, Bacillus subtilis and Staphylococcus epidermidis indicating, in most cases, equipotent or even more effective action than cefuroxime. In order to clarify if the observed antibacterial effects are universal, further research were undertaken to test inhibitory potency of two most potent compounds 3 and 11 on clinical isolates of Staphylococcus aureus. Compound 11 inhibited the growth of methicillin-sensitive S. aureus (MSSA) at MICs of 1.95-7.81 µg/ml, methicillin-resistant S. aureus (MRSA) at MICs of 0.49-1.95 µg/ml and MDR-MRSA at MIC of 0.98 and 3.90 µg/ml, respectively. Finally, inhibitory efficacy of 3 and 11 on planktonic cells and biofilms formation in clinical isolates of S. aureus and Haemophilus parainfluenzae was tested. The majority of cells in biofilm populations of MSSA and MRSA were eradicated at low level of 3, with MBICs in the range of 7.82-15.63 µg/ml.

  10. Lupeol, a triterpene, prevents free radical mediated macromolecular damage and alleviates benzoyl peroxide induced biochemical alterations in murine skin.

    PubMed

    Sultana, Sarwat; Saleem, Mohammad; Sharma, Sonia; Khan, Naghma

    2003-08-01

    In our earlier communication we have shown that Lupeol inhibits early responses of tumour induction in murine skin. The free radical mediated damage to the cellular macromolecules such as DNA, proteins, lipids and alteration in the activities of quinone reductase and xanthine oxidase are important biochemical parameters of tumor development. The suppression of free radical mediated damage to cellular macromolecules and induction of quinone reductase along with depletion of xanthine oxidase are prominent characteristics of chemopreventive agents. In the present investigation, we have elucidated the mechanism of action of lupeol (Lup-20 (29)-en-3beta-ol), a triterpene found in moderate amount in many vegetables, fruits and anti-tumor herbs. In the present investigation, lupeol significantly reduced the free radical mediated DNA-sugar damage and microsomal lipid peroxidation in an iron/ascorbate free radical generating system in vitro. Benzoyl peroxide, a known free radical generating tumor promoter mediated oxidation of proteins and modulation in the activities of quinone reductase as well as xanthine oxidase was significantly prevented by lupeol when tested on murine skin in vivo. It was concluded from this study that lupeol acts as an effective chemopreventive agent against cutaneous toxicity.

  11. In vitro antimicrobial activity of benzoyl peroxide against Propionibacterium acnes assessed by a novel susceptibility testing method.

    PubMed

    Okamoto, Kazuaki; Ikeda, Fumiaki; Kanayama, Shoji; Nakajima, Akiko; Matsumoto, Tatsumi; Ishii, Ritsuko; Umehara, Masatoshi; Gotoh, Naomasa; Hayashi, Naoki; Iyoda, Takako; Matsuzaki, Kaoru; Matsumoto, Satoru; Kawashima, Makoto

    2016-06-01

    Benzoyl peroxide (BPO), a therapeutic agent for acne vulgaris, was assessed for in vitro antimicrobial activity against Propionibacterium acnes using a novel broth microdilution testing that improved BPO solubility. We searched for a suitable culture medium to measure the minimum inhibitory concentration (MIC) of BPO against P. acnes and finally found the Gifu anaerobic medium (GAM) broth supplemented with 0.1(v/v)% glycerol and 2(v/v)% Tween 80, in which BPO dissolved up to 1250 μg/mL and P. acnes grew well. The MICs and minimum bactericidal concentrations (MBCs) of BPO against 44 clinical isolates of P. acnes collected from Japanese patients with acne vulgaris were determined by our testing method using the supplemented GAM broth. The MICs of BPO were 128 or 256 μg/mL against all isolates of P. acnes regardless of susceptibility to nadifloxacin or clindamycin. The MBCs of BPO were also 128 or 256 μg/mL against the same isolates. Moreover, BPO at the MIC showed a rapid bactericidal activity against P. acnes ATCC11827 in time-kill assay. In conclusion, we could develop a novel assay for the MIC and MBC determinations of BPO against P. acnes, which is reliable and reproducible as a broth microdilution testing and the present results suggest that BPO has a potent bactericidal activity against P. acnes.

  12. Correlation of the solid-state reactivities of racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate and its 4,4'-bipyridine cocrystal with their crystal structures.

    PubMed

    Tamboli, Majid I; Bahadur, Vir; Gonnade, Rajesh G; Shashidhar, Mysore S

    2014-11-01

    Racemic 2,4(6)-di-O-benzoyl-myo-inositol 1,3,5-orthoformate, C21H18O8, (1), shows a very efficient intermolecular benzoyl-group migration reaction in its crystals. However, the presence of 4,4'-bipyridine molecules in its cocrystal, C21H18O8·C10H8N2, (1)·BP, inhibits the intermolecular benzoyl-group transfer reaction. In (1), molecules are assembled around the crystallographic twofold screw axis (b axis) to form a helical self-assembly through conventional O-H···O hydrogen-bonding interactions. This helical association places the reactive C6-O-benzoyl group (electrophile, El) and the C4-hydroxy group (nucleophile, Nu) in proximity, with a preorganized El···Nu geometry favourable for the acyl transfer reaction. In the cocrystal (1)·BP, the dibenzoate and bipyridine molecules are arranged alternately through O-H···N interactions. The presence of the bipyridine molecules perturbs the regular helical assembly of the dibenzoate molecules and thus restricts the solid-state reactivity. Hence, unlike the parent dibenzoate crystals, the cocrystals do not exhibit benzoyl-transfer reactions. This approach is useful for increasing the stability of small molecules in the crystalline state and could find application in the design of functional solids.

  13. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives.

    PubMed

    Matin, Mohammed Mahbubul; Nath, Amit R; Saad, Omar; Bhuiyan, Mohammad M H; Kadir, Farkaad A; Abd Hamid, Sharifah Bee; Alhadi, Abeer A; Ali, Md Eaqub; Yehye, Wageeh A

    2016-01-01

    Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular ¹C₄ conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 4-8 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 4-8 were 0.49 < Pa < 0.60 (where Pa is probability 'to be active') as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 4-8 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 4-8 have not been reported with antimicrobial activity, making it a possible valuable lead compound. PMID:27618893

  14. Synthesis, PASS-Predication and in Vitro Antimicrobial Activity of Benzyl 4-O-benzoyl-α-l-rhamnopyranoside Derivatives

    PubMed Central

    Matin, Mohammed Mahbubul; Nath, Amit R.; Saad, Omar; Bhuiyan, Mohammad M. H.; Kadir, Farkaad A.; Abd Hamid, Sharifah Bee; Alhadi, Abeer A.; Ali, Md. Eaqub; Yehye, Wageeh A.

    2016-01-01

    Benzyl α-l-rhamnopyranoside 4, obtained by both conventional and microwave assisted glycosidation techniques, was subjected to 2,3-O-isopropylidene protection to yield compound 5 which on benzoylation and subsequent deprotection of isopropylidene group gave the desired 4-O-benzoylrhamnopyranoside 7 in reasonable yield. Di-O-acetyl derivative of benzoate 7 was prepared to get newer rhamnopyranoside. The structure activity relationship (SAR) of the designed compounds was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antimicrobial activities verified the predictions obtained by the PASS software. Protected rhamnopyranosides 5 and 6 exhibited slight distortion from regular 1C4 conformation, probably due to the fusion of pyranose and isopropylidene ring. Synthesized rhamnopyranosides 4–8 were employed as test chemicals for in vitro antimicrobial evaluation against eight human pathogenic bacteria and two fungi. Antimicrobial and SAR study showed that the rhamnopyranosides were prone against fungal organisms as compared to that of the bacterial pathogens. Interestingly, PASS prediction of the rhamnopyranoside derivatives 4–8 were 0.49 < Pa < 0.60 (where Pa is probability ‘to be active’) as antibacterial and 0.65 < Pa < 0.73 as antifungal activities, which showed significant agreement with experimental data, suggesting rhamnopyranoside derivatives 4–8 were more active against pathogenic fungi as compared to human pathogenic bacteria thus, there is a more than 50% chance that the rhamnopyranoside derivative structures 4–8 have not been reported with antimicrobial activity, making it a possible valuable lead compound. PMID:27618893

  15. Human N-benzoyl-L-tyrosyl-p-aminobenzoic acid hydrolase (human meprin): genomic structure of the alpha and beta subunits.

    PubMed Central

    Hahn, D; Illisson, R; Metspalu, A; Sterchi, E E

    2000-01-01

    N-Benzoyl-L-tyrosyl-p-aminobenzoic acid hydrolase (PPH, human meprin), a zinc-metalloendopeptidase of the astacin family, consists of two similar subunits. As well as in small-intestinal epithelial cells, the enzyme is found in lamina propria leucocytes, human cancer cells and colorectal cancer tissue, making it a potential candidate for a role in tumour formation and cancer progression. To elucidate the mechanisms that control PPH gene expression and to gain more insights into the evolutionary relationship of the two subunits, we analysed the complete exon-intron organization and searched for putative regulatory elements in 3 kb of the upstream region of both genes. The human gene for the alpha subunit is approx. 35 kb in size and contains 14 exons. The gene for the beta subunit is organized in 15 exons and spans approx. 27 kb. A comparison of both genes indicates strong structural similarities. The exons are almost identical in size, except exon 13 in PPHalpha, which codes for an additional I domain not present in PPHbeta. The locations of the respective exon-intron junctions and the intron phases are almost identical; five of them contain conserved split codons. The main variation is in the intron lengths. It can be concluded that PPHalpha and PPHbeta are derived from a common ancestor. Sequence analysis of the 5' flanking DNA with a computer search for promoter elements and different promoter constructs transfected into Caco-2 cells revealed a number of potential regulatory motifs and suggests that each of the two genes is regulated independently. PMID:10657243

  16. Para-(benzoyl)-phenylalanine as a potential inhibitor against LpxC of Leptospira spp.: homology modeling, docking, and molecular dynamics study.

    PubMed

    Pradhan, Dibyabhaba; Priyadarshini, Vani; Munikumar, Manne; Swargam, Sandeep; Umamaheswari, Amineni; Bitla, Aparna

    2014-01-01

    Leptospira interrogans, a Gram-negative bacterial pathogen is the main cause of human leptospirosis. Lipid A is a highly immunoreactive endotoxic center of lipopolysaccharide (LPS) that anchors LPS into the outer membrane of Leptospira. Discovery of compounds inhibiting lipid-A biosynthetic pathway would be promising for dissolving the structural integrity of membrane leading to cell lysis and death of Leptospira. LpxC, a unique enzyme of lipid-A biosynthetic pathway was identified as common drug target of Leptospira. Herein, homology modeling, docking, and molecular dynamics (MD) simulations were employed to discover potential inhibitors of LpxC. A reliable tertiary structure of LpxC in complex with inhibitor BB-78485 was constructed in Modeller 9v8. A data-set of BB-78485 structural analogs were docked with LpxC in Maestro v9.2 virtual screening workflow, which implements three stage Glide docking protocol. Twelve lead molecules with better XP Gscore compared to BB-78485 were proposed as potential inhibitors of LpxC. Para-(benzoyl)-phenylalanine - that showed lowest XP Gscore (-10.35 kcal/mol) - was predicted to have best binding affinity towards LpxC. MD simulations were performed for LpxC and para-(benzoyl)-phenylalanine docking complex in Desmond v3.0. Trajectory analysis showed the docking complex and inter-molecular interactions was stable throughout the entire production part of MD simulations. The results indicate para-(benzoyl)-phenylalanine as a potent drug molecule against leptospirosis. An animated Interactive 3D Complement (I3DC) is available in Proteopedia at http://proteopedia.org/w/Journal:JBSD:10. PMID:23383626

  17. Para-(benzoyl)-phenylalanine as a potential inhibitor against LpxC of Leptospira spp.: homology modeling, docking, and molecular dynamics study.

    PubMed

    Pradhan, Dibyabhaba; Priyadarshini, Vani; Munikumar, Manne; Swargam, Sandeep; Umamaheswari, Amineni; Bitla, Aparna

    2014-01-01

    Leptospira interrogans, a Gram-negative bacterial pathogen is the main cause of human leptospirosis. Lipid A is a highly immunoreactive endotoxic center of lipopolysaccharide (LPS) that anchors LPS into the outer membrane of Leptospira. Discovery of compounds inhibiting lipid-A biosynthetic pathway would be promising for dissolving the structural integrity of membrane leading to cell lysis and death of Leptospira. LpxC, a unique enzyme of lipid-A biosynthetic pathway was identified as common drug target of Leptospira. Herein, homology modeling, docking, and molecular dynamics (MD) simulations were employed to discover potential inhibitors of LpxC. A reliable tertiary structure of LpxC in complex with inhibitor BB-78485 was constructed in Modeller 9v8. A data-set of BB-78485 structural analogs were docked with LpxC in Maestro v9.2 virtual screening workflow, which implements three stage Glide docking protocol. Twelve lead molecules with better XP Gscore compared to BB-78485 were proposed as potential inhibitors of LpxC. Para-(benzoyl)-phenylalanine - that showed lowest XP Gscore (-10.35 kcal/mol) - was predicted to have best binding affinity towards LpxC. MD simulations were performed for LpxC and para-(benzoyl)-phenylalanine docking complex in Desmond v3.0. Trajectory analysis showed the docking complex and inter-molecular interactions was stable throughout the entire production part of MD simulations. The results indicate para-(benzoyl)-phenylalanine as a potent drug molecule against leptospirosis. An animated Interactive 3D Complement (I3DC) is available in Proteopedia at http://proteopedia.org/w/Journal:JBSD:10.

  18. FT-IR and Raman spectroscopic and DFT studies of anti-cancer active molecule N-{(meta-ferrocenyl) Benzoyl} - L-Alanine - Glycine ethyl ester

    NASA Astrophysics Data System (ADS)

    Xavier, T. S.; Kenny, Peter T. M.; Manimaran, D.; Joe, I. Hubert

    2015-06-01

    FT-Raman and FT-IR spectra of N-{(meta-ferrocenyl) Benzoyl} - L-alanine - glycine ethyl ester were recorded in solid phase. The optimized molecular geometry, the vibrational wavenumbers, the infrared intensities and the Raman scattering intensities were calculated by using density functional method(B3LYP) with 6-31G(d, p) basis set. Vibrational assignment of the molecule was done by using potential energy distribution analysis. Natural bond orbital analysis, Mulliken charge analysis and HOMO-LUMO energy were used to elucidate the reasons for intra molecular charge transfer. Docking studies were conducted to predict its anticancer activity.

  19. Sub-group Analyses from a Trial of a Fixed Combination of Clindamycin Phosphate 1.2% and Benzoyl Peroxide 3.75% Gel for the Treatment of Moderate-to-severe Acne Vulgaris

    PubMed Central

    Korotzer, Andrew

    2015-01-01

    Background: Acne vulgaris is commonplace and can be difficult to manage. Providing an effective and well-tolerated treatment may lead to improved adherence, increased patient satisfaction, and improved clinical outcomes. Methods: A review of efficacy, safety, and cutaneous tolerability of clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel in 498 patients with moderate-to-severe acne vulgaris enrolled in a multicenter Phase III study randomized to receive active or vehicle once daily for 12 weeks, including the most recent post-hoc analyses. Results: Significantly superior reductions in lesion counts were observed with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel from Week 4, with median percent reductions in inflammatory and noninflammatory lesions from baseline of 68.4 and 57.9 percent, respectively (bothp<0.001 versus vehicle). More than half (55.1%) of the severe acne vulgaris patients treated with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel achieved ≥2-grade improvement from baseline in their Evaluator’s Global Severity Score, and almost a third of the adolescent acne vulgaris patients (32.4%) achieved at least a marked improvement in their acne vulgaris as early as Week 2. In adult female acne overall treatments success was achieved in 52.7 percent of patients treated with clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel. Overall, and in the specific subpopulations, clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel was well-tolerated with a similar adverse event profile to vehicle. Limitations: Post-hoc analyses from a single clinical trial with demographic imbalances that could potentially confound the results. Conclusion: Clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel appears to be effective in treating acne across various clinically relevant sub-groups. PMID:26705445

  20. Identification of 2-[2-nitro-4-(trifluoromethyl)benzoyl]- cyclohexane-1,3-dione metabolites in urine of patients suffering from tyrosinemia type I with the use of 1H and 19F NMR spectroscopy.

    PubMed

    Szczeciński, Przemysław; Lamparska, Diana; Gryff-Keller, Adam; Gradowska, Wanda

    2008-01-01

    Organic extracts of six urine samples from children treated with nitisinone, a medicine against tyrosinemia type I, were investigated by (1)H and (19)F NMR spectroscopy. The presence of unchanged 2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione (NTBC), 6-hydroxy-2-[2-nitro-4-(trifluoromethyl)benzoyl]cyclohexane-1,3-dione (NTBC-OH) and 2-nitro-4-trifluoromethylbenzoic acid (NTFA) as well as a few other unidentified compounds containing CF(3) group was documented.

  1. Crystal structure of 2-benzoyl­amino-N′-(4-hy­droxy­benzyl­idene)-3-(thio­phen-2-yl)prop-2-eno­hydrazide

    PubMed Central

    Subbulakshmi, Karanth N.; Narayana, Badiadka; Yathirajan, Hemmige S.; Jasinski, Jerry P.; Rathore, Ravindranath S.; Glidewell, Christopher

    2016-01-01

    In the title compound, C21H17N3O3S, the non-H atoms, apart from those in the benzoyl group, are almost coplanar (r.m.s. deviation = 0.049 Å) and the benzoyl group is almost orthogonal to the plane of the rest of the mol­ecule [dihedral angle = 80.34 (6)°]. In the crystal, a combination of N—H⋯O and asymmetric bifurcated O—H⋯(N,O) hydrogen bonds link the mol­ecules into a three-dimensional network. Weak C—H⋯O inter­actions are also observed. PMID:27536390

  2. The efficacy, safety, and tolerability of adapalene versus benzoyl peroxide in the treatment of mild acne vulgaris: a randomized trial.

    PubMed

    Babaeinejad, S H; Fouladi, R F

    2013-07-01

    Topical treatments, such as adapalene and benzoyl peroxide (BPO), are popular in mild-to-moderate acne vulgaris. This study aimed to compare the efficacy, safety and tolerability of adapalene and BPO in mild acne vulgaris. In this single-center, randomized, double-blind, clinical trial, 60 patients with mild acne vulgaris received either topical adapalene 0.1% gel or topical BPO 2.5% gel on their face once daily for two months. The changes of acne lesion count (efficacy), any adverse effect (safety), and the patients' overall satisfaction (tolerability) were compared after 3 months of follow-up. In both groups the mean number of noninflammatory, inflammatory and total lesions decreased significantly from baseline (10.77±5.54, 9.73±5.09, and 20.50±7.54, respectively in adapalene group; 11.50±5.92, 8.43±5.45, and 19.93±9.01, respectively in BPO group) to the third month (1.70±1.68, 0.33±0.66, and 0.50±0.78, respectively in adapalene group; 4.23±4.14, 0.33±0.71, and 4.13±4.44, respectively in BPO group; P<0.001 for all), posttreatment. Although the mean number of inflammatory lesions was significantly lower in BPO receivers only at first month (P =0.001), the mean number of noninflammatory and total lesions was significantly lower in adapalene group at second (P = 0.04 and 0.03, respectively) and third (P =0.02 and <0.001, respectively) months, posttreatment. The adverse events were minimal and self-limited (26.7% in adapalene group, 20% in BPO group, p=0.54). The patients' overall satisfaction was good to excellent in 93.3% of adapalene receivers vs. 73.3% in BPO group (P=0.08). Both topical adapalene 0.1% and BPO 2.5% gels seem safe and effective in mild acne vulgaris, with a marginal tendency toward the former.

  3. The efficacy, safety and tolerability of adapalene versus benzoyl peroxide in the treatment of mild acne vulgaris; a randomized trial.

    PubMed

    Babaeinejad, S H; Fouladi, R F

    2013-09-01

    Topical treatments, such as adapalene and benzoyl peroxide (BPO), are popular in mild-to-moderate acne vulgaris. This study aimed to compare the efficacy, safety and tolerability of adapalene and BPO in mild acne vulgaris. In this single-center, randomized, double-blind, clinical trial, 60 patients with mild acne vulgaris received either topical adapalene 0.1% gel or topical BPO 2.5% gel on their face once daily for two months. The changes of acne lesion count (efficacy), any adverse effect (safety), and the patients' overall satisfaction (tolerability) were compared after 3 months of follow-up. In both groups the mean number of noninflammatory, inflammatory and total lesions decreased significantly from baseline (10.77±5.54, 9.73±5.09, and 20.50±7.54, respectively in adapalene group; 11.50±5.92, 8.43±5.45, and 19.93±9.01, respectively in BPO group) to the third month (1.70±1.68, 0.33±0.66, and 0.50±0.78, respectively in adapalene group; 4.23±4.14, 0.33±0.71, and 4.13±4.44, respectively in BPO group; P<0.001 for all), posttreatment. Although the mean number of inflammatory lesions was significantly lower in BPO receivers only at first month (P=0.001), the mean number of noninflammatory and total lesions was significantly lower in adapalene group at second (P= 0.04 and 0.03, respectively) and third (P=0.02 and <0.001, respectively) months, posttreatment. The adverse events were minimal and self-limited (26.7% in adapalene group, 20% in BPO group, P=0.54). The patients' overall satisfaction was good-excellent in 93.3% of adapalene receivers vs. 73.3% in BPO group (P=0.08). Both topical adapalene 0.1% and BPO 2.5% gels seem safe and effective in mild acne vulgaris, with a marginal tendency toward the former.

  4. Formulation and evaluation of a topical niosomal gel containing a combination of benzoyl peroxide and tretinoin for antiacne activity

    PubMed Central

    Gupta, Ankush; Singh, Sima; Kotla, Niranjan G; Webster, Thomas J

    2015-01-01

    A skin disease, like acne, is very common and normally happens to everyone at least once in their lifetime. The structure of the stratum corneum is often compared with a brick wall, with corneocytes surrounded by the mortar of the intercellular lipid lamellae. One of the best options for successful drug delivery to the affected area of skin is the use of elastic vesicles (niosomes) which can be transported through the skin through channel-like structures. In this study, a combination of tretinoin (keratolytic agent) and benzoyl peroxide (BPO) (a potent antibacterial) was given by using niosomes as promising carriers for the effective treatment of acne by acting on a pathogenic site. In this section, niosomal gel formulation encapsulated drugs have been evaluated for in vitro, ex vivo, and in vivo, for their predetermined characteristics; and finally the stability of the niosome gel was tested at different temperature conditions for understanding of the storage conditions required for maintaining the quality of formulation attributes. The prepared niosome was found to be in the range of 531 nm with a zeta potential of −43 mV; the entrapment efficiencies of tretinoin (TRA) and BPO niosomes were found to be 96.25%±0.56% and 98.75%±1.25%, respectively. The permeated amount of TRA and BPO from the niosomal gel after 24 hours was calculated as 6.25±0.14 μg/cm2 and 5.04±0.014 μg/cm2, respectively. A comparative drug retention study in Wistar rat skin using cream, an alcoholic solution, and a niosomal gel showed 11.54 μg, 2.68 μg, and 15.54 μg amounts of TRA and 68.85 μg, 59.98 μg, and 143.78 μg amounts of BPO were retained in the layers of skin, respectively. In vivo studies of the niosomal gel and antiacne cream of TRA and BPO showed that the niosomal gel was more efficacious than the antiacne cream because niosomal gels with a 4.16-fold lower dose of BPO provided the same therapeutic index at targeted sites in comparison to the antiacne cream. PMID

  5. Formulation and evaluation of a topical niosomal gel containing a combination of benzoyl peroxide and tretinoin for antiacne activity.

    PubMed

    Gupta, Ankush; Singh, Sima; Kotla, Niranjan G; Webster, Thomas J

    2015-01-01

    A skin disease, like acne, is very common and normally happens to everyone at least once in their lifetime. The structure of the stratum corneum is often compared with a brick wall, with corneocytes surrounded by the mortar of the intercellular lipid lamellae. One of the best options for successful drug delivery to the affected area of skin is the use of elastic vesicles (niosomes) which can be transported through the skin through channel-like structures. In this study, a combination of tretinoin (keratolytic agent) and benzoyl peroxide (BPO) (a potent antibacterial) was given by using niosomes as promising carriers for the effective treatment of acne by acting on a pathogenic site. In this section, niosomal gel formulation encapsulated drugs have been evaluated for in vitro, ex vivo, and in vivo, for their predetermined characteristics; and finally the stability of the niosome gel was tested at different temperature conditions for understanding of the storage conditions required for maintaining the quality of formulation attributes. The prepared niosome was found to be in the range of 531 nm with a zeta potential of -43 mV; the entrapment efficiencies of tretinoin (TRA) and BPO niosomes were found to be 96.25%±0.56% and 98.75%±1.25%, respectively. The permeated amount of TRA and BPO from the niosomal gel after 24 hours was calculated as 6.25±0.14 μg/cm(2) and 5.04±0.014 μg/cm(2), respectively. A comparative drug retention study in Wistar rat skin using cream, an alcoholic solution, and a niosomal gel showed 11.54 μg, 2.68 μg, and 15.54 μg amounts of TRA and 68.85 μg, 59.98 μg, and 143.78 μg amounts of BPO were retained in the layers of skin, respectively. In vivo studies of the niosomal gel and antiacne cream of TRA and BPO showed that the niosomal gel was more efficacious than the antiacne cream because niosomal gels with a 4.16-fold lower dose of BPO provided the same therapeutic index at targeted sites in comparison to the antiacne cream.

  6. Use of neutral capillaries for the enantioseparation of N-benzoylated amino acids by capillary electrophoresis with bromobalhimycin as chiral selector.

    PubMed

    Peng, Yongbo; Zhang, Tingting; Wang, Tingting; Liu, Zhenghua; Crommen, Jacques; Jiang, Zhengjin

    2013-05-01

    In this study, the partial filling technique on both polycationic polymer hexadimethrine bromide (HDB) modified capillary and eCAP neutral capillary were systematically compared in order to enhance the enantioseparation ability of bromobalhimycin as CE additive. The separation conditions, such as pH, the plug length, and the concentration of bromobalhimycin, etc., were optimized in order to obtain satisfactory separations. As expected, for all tested 28 N-benzoylated amino acids, up to five times higher enantioresolutions were obtained on the eCAP neutral capillary compared to that on the polycationic polymer hexadimethrine bromide modified capillary. Moreover, 26 of 28 tested racemic compounds were almost baseline- resolved without observing any interference from the front of the plug of bromobalhimycin. Although the limitation of longer running time on the neutral capillary, it allows the use of higher content of bromobalhimycin in the running buffer without any interference on the detection of analytes when enantioseparations are more difficult to obtain.

  7. DNA sequence-specific adenine alkylation by the novel antitumor drug tallimustine (FCE 24517), a benzoyl nitrogen mustard derivative of distamycin.

    PubMed Central

    Broggini, M; Coley, H M; Mongelli, N; Pesenti, E; Wyatt, M D; Hartley, J A; D'Incalci, M

    1995-01-01

    FCE 24517, a novel distamycin derivative possessing potent antitumor activity, is under initial clinical investigation in Europe. In spite of the presence of a benzoyl nitrogen mustard group this compound fails to alkylate the N7 position of guanine, the major site of alkylation by conventional nitrogen mustards. Characterisation of DNA-drug adducts revealed only a very low level of adenine adduct formation. Using a modified Maxam-Gilbert sequencing method the consensus sequence for FCE 24517-adenine adduct formation was found to be 5'-TTTTGA-3'. A single base modification in the hexamer completely abolishes the alkylation of adenine. Using a Taq polymerase stop assay alkylations were confirmed at the A present in the hexamer TTTTGA and, in addition, in one out of three TTTTAA sequences present in the plasmid utilized. The sequence specificity of alkylation by FCE 24517 is therefore the most striking yet observed for an alkylating agent of small molecular weight. Images PMID:7870593

  8. Optimization and Validation of High-Performance Chromatographic Condition for Simultaneous Determination of Adapalene and Benzoyl Peroxide by Response Surface Methodology

    PubMed Central

    Huang, Yaw-Bin; Wu, Pao-Chu

    2015-01-01

    The aim of this study was to develop a simple and reliable high-performance chromatographic (HPLC) method for simultaneous analysis of adapalene and benzoyl peroxide in pharmaceutical formulation by response surface methodology (RSM). An optimized mobile phase composed of acetonitrile, tetrahydrofuran and water containing 0.1% acetic acid at a ratio of 25:50:25 by volume was successfully predicted by using RSM. An isocratic separation was achieved by using the condition. Furthermore, the analytical method was validated in terms of specificity, linearity, accuracy and precision in a range of 80% to 120% of the expected concentration. Finally, the method was successfully applied to the analysis of a commercial product. PMID:25793581

  9. Attenuation of benzoyl peroxide-mediated cutaneous oxidative stress and hyperproliferative response by the prophylactic treatment of mice with spearmint (Mentha spicata).

    PubMed

    Saleem, M; Alam, A; Sultana, S

    2000-10-01

    The modulating effect of spearmint (Mentha spicata) on benzoyl peroxide-induced responses of tumor promotion in murine skin was investigated. Benzoyl peroxide (BPO) is an effective cutaneous tumor promoter acting through the generation of oxidative stress, induction of ornithine decarboxylase activity and by enhancing DNA synthesis. BPO treatment (20 mg/animal) increased cutaneous microsomal lipid peroxidation and hydrogen peroxide generation. The activity of cutaneous antioxidant enzymes, namely catalase, glutathione peroxidase, glutathione reductase and glutathione S-transferase, was decreased and the level of cutaneous glutathione was depleted. BPO treatment also induced the ornithine decarboxylase activity and enhanced the [3H]thymidine uptake in DNA synthesis in murine skin. Prophylactic treatment of mice with spearmint extract (10, 15 and 20 mg/kg) 1 hr before BPO treatment resulted in the diminution of BPO-mediated damage. The susceptibility of cutaneous microsomal membrane to lipid peroxidation and hydrogen peroxide generation was significantly reduced (P < 0.05 ). In addition, depleted levels of glutathione, inhibited activity of glutathione dependent and antioxidant enzymes were recovered to a significant level (P < 0.01, P < 0.05 and P < 0.01, respectively). Similarly, the elevated ornithine decarboxylase activity and enhanced thymidine uptake in DNA synthesis was inhibited significantly (P < 0.05 ) in a dose-dependent manner. The protective effect of spearmint was dose dependent in all parameters. The result suggests that spearmint is an effective chemopreventive agent that may suppress BPO-induced cutaneous oxidative stress, toxicity and hyperproliferative effects in the skin of mice.

  10. 1,3-Dimethyl-5-(3,4,5-tris(alkoxy)benzoyl) barbituric acid derivatives and their liquid crystalline difluoroboron complexes: Synthesis, characterization and comparative investigations of mesomorphic, thermotropic and thermo-morphologic properties

    NASA Astrophysics Data System (ADS)

    Giziroglu, Emrah; Nesrullajev, Arif; Orhan, Nil

    2014-01-01

    A series of 1,3-dimethyl-5-(3,4,5-tris(alkoxy)benzoyl) barbituric acid derivatives 1a-4a with various chain length were synthesized by our group for the first time through the addition of 1,3-dimethyl barbituric acid to 3,4,5-tris(alkoxy)benzoyl chloride at room temperature in presence of pyridine. For preparation of their difluoroboron complexes, the derivatives 1a-4a reacts with borontrifluoride in the presence of triethylamine affording 1b-4b in moderate yields. All derivatives and complexes have been fully characterized by MS, FT-IR and multinuclear NMR spectroscopy. We also explored their liquid crystal properties by using POM, OM, CTW and DSC techniques. The results show that 3b and 4b with longer alkyl chain are monomorphic mesogens and exhibited enantiotropic thermotropic liquid crystalline mesophases. Investigation of their mesomorphic, thermo-morphologic and thermotropic properties is presented in this work.

  11. Characterization and heterologous expression of hydroxycinnamoyl/benzoyl-CoA:anthranilate N-hydroxycinnamoyl/benzoyltransferase from elicited cell cultures of carnation, Dianthus caryophyllus L.

    PubMed

    Yang, Q; Reinhard, K; Schiltz, E; Matern, U

    1997-12-01

    Benzoyl-CoA:anthranilate N-benzoyltransferase catalyzes the first committed reaction of phytoalexin biosynthesis in carnation (Dianthus caryophyllus L.), and the product N-benzoylanthranilate is the precursor of several sets of dianthramides. The transferase activity is constitutively expressed in suspension-cultured carnation cells and can be rapidly induced by the addition of yeast extract. The enzyme was purified to homogeneity from yeast-induced carnation cells and shown to consist of a single polypeptide chain of 53 kDa. Roughly 20% of the sequence was identified by micro-sequencing of tryptic peptides, and some of these sequences differed in a few amino acid residues only suggesting the presence of isoenzymes. A specific 0.8 kb cDNA probe was generated by RT-PCR, employing degenerated oligonucleotide primers complementary to two of the tryptic peptides and using poly(A)+ RNA from elicited carnation cells. Five distinct benzoyltransferase clones were isolated from a cDNA library, and three cDNAs, pchcbt1-3, were sequenced and shown to encode full-size N-benzoyltransferases. The translated peptide sequences revealed more than 95% identity among these three clones. The additional two clones harbored insert sequences mostly homologous with pchcbt 1 but differing in the 3'-flanking regions due to variable usage of poly(A) addition sites. The identity of the clones was confirmed by matching the translated polypeptides with the tryptic enzyme sequences as well as by the activity of the benzoyltransferase expressed in Escherichia coli. Therefore, carnation encodes a small family of anthranilate N-benzoyltransferase genes. In vitro, the benzoyltransferases exhibited narrow substrate specificity for anthranilate but accepted a variety of aromatic acyl-CoAs. Catalytic rates with cinnamoyl- or 4-coumaroyl-CoA exceeded those observed with benzoyl-CoA, although the corresponding dianthramides did not accumulate in vivo. Thus the cDNAs described represent also the first

  12. Structure-Toxicity Relations of Some Substituted 2-BENZOYL-1H-INDENE-1,3(2H)-DIONE Rodenticides.

    NASA Astrophysics Data System (ADS)

    Opong-Mensah, Kofi

    Chemical control of rodents depends primarily on the use of poisoned baits. The need for more potent rodenticides arises out of the evolution of resistant strains in rodent populations. One novel and 5 known benzoylindandiones were synthesized by condensation of methyl aryl ketones with dimethyl phthalate. Novel TLC, HPLC, and GC methods were developed to assay the acylindandiones after characterization by MS, IR and FT-NMR spectroscopy. The n-octanol/water partition coefficient (log P), acid dissociation constants (pKa) and mouse LD(,50)s were determined experimentally. Quantum mechanical molecular descriptors, such as HOMO-LUMO energies, were generated using computer models. The structure-toxicity relations of the benzoylindandiones were developed using regression models and partial least squares analysis. LD(,50)s (mM/Kg) for male Sprague-Dawley mice by intraperitoneal injection for 2-benzoyl-1,3-indandione (1), 2-(4'-methoxybenzoyl)-1,3-indandione (2), 2-(3'-methylbenzoyl) -1,3-indandione (3), 2-(4'-methylbenzoyl)-1,3-indandione (4), 2-(4'-isopropylbenzoyl)-1,3-indandione (5), and 2 -diphenylacetyl-1,3-indandione (6) were (median, 95% confidence limits): 1, 0.038 (0.030-0.049); 2, 0.026 (0.021-0.037); 3, 0.083 (0.065-0.106); 4, 0.077 (0.060-0.098); 5, 0.096 (0.071-0.128); and 6, 0.048 (0.035-0.064); log P was (mean (+OR-) standard error): 1, 1.14 (+OR-) 0.03; 2, 1.37 (+OR -) 0.02; 3, 1.24 (+OR-) 0.04; 4, 1.31 (+OR-) 0.02; 5, 1.43 (+OR-) 0.03 and 6, 2.47 (+OR-) 0.03; the pKas were (mean (+OR-) standard error): 1, 3.08 (+OR-) 0.02; 2, 3.91 (+OR -) 0.01; 3, 2.63 (+OR-) 0.01; 4, 2.93 (+OR-) 0.02; 5, 3.91 (+OR-) 0.01; and 6, 3.31 (+OR-) 0.01. -Log (,10)LD(,50) of the 6 indandiones correlated highly with the mean of the C-13 NMR chemical shifts of the carbonyl carbons, but poorly with pKa, IR carbonyl stretching frequencies, HOMO, LUMO, Hammett sigma and log P. 2-Benzoyl-1,3-indandione and 2-(4'-methoxybenzoyl) -1,3-indandione were more potent rodenticides than

  13. Efficacy and Tolerability of a Combined 445nm and 630nm Over-the-counter Light Therapy Mask with and without Topical Salicylic Acid versus Topical Benzoyl Peroxide for the Treatment of Mild-to-moderate Acne Vulgaris

    PubMed Central

    Swenson, Nicole; Macri, Angela; Manway, Mitchell; Paparone, Paige

    2016-01-01

    Objective: To evaluate the efficacy and tolerance of a combined 445nm/630nm light therapy mask for the treatment of mild-to-moderate acne vulgaris with and without topical 1% salicylic acid with retinol versus 2.5% benzoyl peroxide. Design: A 12-week evaluator-blinded, randomized study. Subjects were randomized to be treated with the 445nm/630nm light therapy mask alone, benzoyl peroxide, or 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol. Participants: Healthy male and female subjects 12 to 35 years old with Fitzpatrick skin types I to VI and mild-to-moderate facial acne vulgaris. Measurements: The primary endpoint was the change in the number of inflammatory acne lesions after 12 weeks of treatment. Secondary endpoints included the change in noninflammatory acne lesions, change in total acne lesions, change in Investigator Global Acne Assessments, and overall responder rate. Results: 445nm/630nm light therapy mask-treated subjects showed a 24.4-percent improvement in inflammatory acne lesions (p<0.01) versus 17.2 percent (p<0.05) and 22.7 percent (p<0.01) in benzoyl peroxide and 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol, respectively, a 19.5-percent improvement in noninflammatory lesions (p<0.001) versus 6.3 and 4.8 percent for benzoyl peroxide and 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol, respectively. Subjects in the 445nm/630nm light therapy mask group also achieved a 19.0-percent improvement in the Investigator Global Acne Assessment (p<0.001) versus 4.7 percent in benzoyl peroxide and 13.9 percent in 445nm/630nm light therapy mask with topical 1% salicylic acid with retinol (p<0.01). Treatments were well-tolerated overall with trends toward less early irritation in the 445nm/630nm light therapy mask group. Conclusion: 445nm/630nm light therapy mask appears to be a safe and effective therapy for mild-to-moderate acne. PMID:27354885

  14. Synthesis, spectral characterization, thermal behaviour, antibacterial activity and DFT calculation on N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester.

    PubMed

    Bharty, M K; Dani, R K; Kushawaha, S K; Prakash, Om; Singh, Ranjan K; Sharma, V K; Kharwar, R N; Singh, N K

    2015-06-15

    Two new compounds N'-[bis(methylsulfanyl) methylene]-2-hydroxybenzohydrazide {Hbmshb (1)} and N'-(4-methoxy benzoyl)-hydrazinecarbodithioic acid ethyl ester {H2mbhce (2)} have been synthesized and characterized with the aid of elemental analyses, IR, NMR and single crystal X-ray diffraction data. Compounds 1 and 2 crystallize in orthorhombic and monoclinic systems with space group Pna21 and P21/n, respectively. Inter and intra molecular hydrogen bonding link two molecules and provide linear chain structure. In addition to this, compound 2 is stabilized by CH⋯π and NH⋯π interactions. Molecular geometry from X-ray analysis, geometry optimization, charge distribution, bond analysis, frontier molecular orbital (FMO) analysis and non-linear optical (NLO) effects have been performed using the density functional theory (DFT) with the B3LYP functional. The bioefficacy of compounds has been examined against the growth of bacteria to evaluate their anti-microbial potential. Compounds 1 and 2 are thermally stable and show NLO behaviour better than the urea crystal. PMID:25767993

  15. Enhanced solubility and antibacterial activity of lipophilic fluoro-substituted N-benzoyl-2-aminobenzothiazoles by complexation with β-cyclodextrins.

    PubMed

    Trapani, A; De Laurentis, N; Armenise, D; Carrieri, A; Defrenza, I; Rosato, A; Mandracchia, D; Tripodo, G; Salomone, A; Capriati, V; Franchini, C; Corbo, F

    2016-01-30

    Some lipophilic fluoro-substituted N-benzoyl-2-aminobenzothiazole antibacterial agents have been evaluated for their activity in the presence of cyclodextrins (CDs) containing aqueous solutions where CDs are adopted as solubilizing excipients for improving the poor water solubility of these compounds. For such purpose both the natural β-CD and one of FDA/EMA approved CDs for parenteral use (i.e. HP-β-CD) have been employed. The solubility rank order observed was accounted for by thermal analysis (Differential Scanning Calorimetry) and FT-IR spectroscopy. The most promising compound was subjected to further NMR spectroscopic studies and molecular modelling simulations to verify the interactions between the guest molecule and the CD cavity. The assessment of the antibacterial activity of such compounds against selected Gram positive and Gram negative bacterial strains clearly showed that their antimicrobial effectiveness may, quite in all instances, be positively affected by complexation with β-CD and HP-β-CD. These results, which are in some ways in contrast with those already reported in the literature, are herein discussed on the basis of plausible mechanisms. Moreover, this investigation also reveals that the described methodology of complexing both lipophilic and hydrophilic antimicrobial agents with CDs may be an useful approach to enhance their effectiveness as well as a promising strategy to overcome even the microbial resistance problem.

  16. Benzoyl Peroxide Formulated Polycarbophil/Carbopol 934P Hydrogel with Selective Antimicrobial Activity, Potentially Beneficial for Treatment and Prevention of Bacterial Vaginosis

    PubMed Central

    Cavera, Veronica L.; Rogers, Michael A.; Huang, Qingrong; Zubovskiy, Konstantin; Chikindas, Michael L.

    2013-01-01

    The human vagina is colonized by a variety of indigenous microflora; in healthy individuals the predominant bacterial genus is Lactobacillus while those with bacterial vaginosis (BV) carry a variety of anaerobic representatives of the phylum Actinobacteria. In this study, we evaluated the antimicrobial activity of benzoyl peroxide (BPO) encapsulated in a hydrogel against Gardnerella vaginalis, one of the causative agents of BV, as well as indicating its safety for healthy human lactobacilli. Herein, it is shown that in well diffusion assays G. vaginalis is inhibited at 0.01% hydrogel-encapsulated BPO and that the tested Lactobacillus spp. can tolerate concentrations of BPO up to 2.5%. In direct contact assays (cells grown in a liquid culture containing hydrogel with 1% BPO or BPO particles), we demonstrated that hydrogels loaded with 1% BPO caused 6-log reduction of G. vaginalis. Conversely, three of the tested Lactobacillus spp. were not inhibited while L. acidophilus growth was slightly delayed. The rheological properties of the hydrogel formulation were probed using oscillation frequency sweep, oscillation shear stress sweep, and shear rate sweep. This shows the gel to be suitable for vaginal application and that the encapsulation of BPO did not alter rheological properties. PMID:24382940

  17. Benzoyl peroxide formulated polycarbophil/carbopol 934P hydrogel with selective antimicrobial activity, potentially beneficial for treatment and prevention of bacterial vaginosis.

    PubMed

    Xu, Shiqi; Cavera, Veronica L; Rogers, Michael A; Huang, Qingrong; Zubovskiy, Konstantin; Chikindas, Michael L

    2013-01-01

    The human vagina is colonized by a variety of indigenous microflora; in healthy individuals the predominant bacterial genus is Lactobacillus while those with bacterial vaginosis (BV) carry a variety of anaerobic representatives of the phylum Actinobacteria. In this study, we evaluated the antimicrobial activity of benzoyl peroxide (BPO) encapsulated in a hydrogel against Gardnerella vaginalis, one of the causative agents of BV, as well as indicating its safety for healthy human lactobacilli. Herein, it is shown that in well diffusion assays G. vaginalis is inhibited at 0.01% hydrogel-encapsulated BPO and that the tested Lactobacillus spp. can tolerate concentrations of BPO up to 2.5%. In direct contact assays (cells grown in a liquid culture containing hydrogel with 1% BPO or BPO particles), we demonstrated that hydrogels loaded with 1% BPO caused 6-log reduction of G. vaginalis. Conversely, three of the tested Lactobacillus spp. were not inhibited while L. acidophilus growth was slightly delayed. The rheological properties of the hydrogel formulation were probed using oscillation frequency sweep, oscillation shear stress sweep, and shear rate sweep. This shows the gel to be suitable for vaginal application and that the encapsulation of BPO did not alter rheological properties.

  18. Molecular modeling and spectroscopic studies on binding of 2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)benzoyl] pyridine to human serum albumin

    NASA Astrophysics Data System (ADS)

    He, Wen-ying; Chen, Hui-juan; Sheng, Fen-ling; Yao, Xiao-jun

    2009-10-01

    BAFP (2,6-bis[4-(4-amino-2-trifluoromethylphenoxy)benzoyl] pyridine), a synthesized polyimide compound, was exploited for the first time to analyze its interaction with human serum albumin (HSA) by molecular modeling, fluorescence and Fourier transform infrared attenuated total reflection spectroscopy (FTIR ATR) with drug concentrations of 3.3 × 10 -6 to 3.0 × 10 -5 mol L -1. Molecular docking was performed to reveal the possible binding mode. The results suggested that BAFP can strongly bind to human serum albumin (HSA) and the primary binding site of BAFP is located in site II of HSA, which is supported by the results from the competitive experiment. The binding constants for the interaction of BAFP with HSA have been evaluated from relevant fluorescence data at different temperatures (296, 303, 310 and 308 K). The alterations of the protein secondary structure in the presence of BAFP in aqueous solution were quantitatively calculated by the evidences from FTIR ATR spectroscopes. The binding process was exothermic and spontaneous, as indicated by the thermodynamic analyses, and the major part of the binding energy is hydrophobic interaction, which is also in good agreement with the results of molecule modeling study. The enthalpy change Δ H0, the free energy change Δ G0 and the entropy change Δ S0 of 296 K were calculated to be -7.75, -27.68 kJ mol -1 and 67.33 J mol -1 K -1, respectively.

  19. The Effect of Organic Solvents and Other Parameters on Trypsin-Catalyzed Hydrolysis of Na-Benzoyl-arginine-p-nitroanilide. A Project-Oriented Biochemical Experiment

    NASA Astrophysics Data System (ADS)

    Correia, L. C.; Bocewicz, A. C.; Esteves, S. A.; Pontes, M. G.; Versieux, L. M.; Teixeira, S. M. R.; Santoro, M. M.; Bemquerer, M. P.

    2001-11-01

    The study of enzymatic catalysis is a classical biochemistry experiment for undergraduate classes. We propose the utilization of the serine protease trypsin to discuss several parameters affecting enzyme catalysis. Hydrolysis of the chromogenic substrate Na -benzoyl-arginine-p-nitroanilide (BApNA) was followed by spectrophotometric monitoring. The optimal pH and temperature values were found to be 8.0 and 40 °C, respectively. Km and Vmax values were obtained by adjustment to Michaelis-Menten, Lineweaver-Burke, and Hanes equations. We then investigated the effect of organic solvents (a series of alcohols) on the hydrolysis of the chromogenic substrate. The reaction rate was reduced in the presence of methanol and further reduced by ethanol, 1-propanol, and 2-propanol, when compared to the data obtained with buffer. Finally the students were asked to measure the molar absorptivity of p-nitrophenol in the presence of the alcohols employed for the kinetic experiments. Thus they could learn that the value of this parameter varies with the solvent. These experiments were designed as a project-oriented approach to teach biochemistry methodologies and theoretical aspects of enzyme kinetics. They took about four months with four to six hours per week spent in the laboratory.

  20. Investigation of the formation of benzoyl peroxide, benzoic anhydride, and other potential aerosol products from gas-phase reactions of benzoylperoxy radicals

    NASA Astrophysics Data System (ADS)

    Strollo, Christen M.; Ziemann, Paul J.

    2016-04-01

    The secondary organic aerosol (SOA) products of the reaction of benzaldehyde with Cl atoms and with OH radicals in air in the absence of NOx were investigated in an environmental chamber in order to better understand the possible role of organic peroxy radical self-reactions in SOA formation. SOA products and authentic standards were analyzed using mass spectrometry and liquid chromatography, and results show that the yields of benzoyl peroxide (C6H5C(O)OO(O)CC6H5) and benzoic anhydride (C6H5C(O)O(O)CC6H5), two potential products from the gas-phase self-reaction of benzoylperoxy radicals (C6H5C(O)OO·), were less than 0.1%. This is in contrast to results of recent studies that have shown that the gas-phase self-reactions of β-nitrooxyperoxy radicals formed from reactions of isoprene with NO3 radicals form dialkyl peroxides that contribute significantly to gas-phase and SOA products. Such reactions have also been proposed to explain the gas-phase formation of extremely low volatility dimers from autooxidation of terpenes. The results obtained here indicate that, at least for benzoylperoxy radicals, the self-reactions form only benzoyloxy radicals. Analyses of SOA composition and volatility were inconclusive, but it appears that the SOA may consist primarily of oligomers formed through heterogeneous/multiphase reactions possibly involving some combination of phenol, benzaldehyde, benzoic acid, and peroxybenzoic acid.

  1. The photoprotective effects of 2-benzoyl-3-phenylquinoxaline 1,4-dioxide against UVB-induced damage in HaCaT cells.

    PubMed

    Mouawad, Joe; Saadeh, Fadi; Tabosh, Hayat Al; Haddadin, Makhluf J; Gali-Muhtasib, Hala

    2016-08-01

    With the increasing levels of atmospheric ozone depletion, there has been much concern about the causal effects of high levels of ultraviolet radiation reaching the Earth's surface on skin cancer. This has led to growing interest in identifying new active ingredients for use in commercial sunscreens. In our study, the chemical compound 2-benzoyl-3-phenylquinoxaline 1,4-dioxide (BPQ) prepared by the Beirut reaction was tested for its ability to protect a human keratinocyte cell line (HaCaT) against ultraviolet B radiation (280-315 nm). We show that BPQ exhibited strong absorbance in the UVB range, with an overall absorption spectrum very similar to that of Padimate-O, a well-known active ingredient used in commercial sunscreens. HaCaT cells, which were irradiated with UVB in the presence of multiple doses of BPQ, exhibited, in a dose-dependent fashion, a significantly higher viability and lower oxidative stress levels than cells irradiated in the absence of drug. Our results show that BPQ is a potential photoprotective drug that holds great promise for use as an active ingredient in commercial sunscreens. PMID:27377483

  2. Comparison of chloroxylenol 0.5% plus salicylic acid 2% cream and benzoyl peroxide 5% gel in the treatment of acne vulgaris: a randomized double-blind study.

    PubMed

    Boutli, F; Zioga, M; Koussidou, T; Ioannides, D; Mourellou, O

    2003-01-01

    A 12-week double-blind randomized study was performed to compare benzoyl peroxide 5% (BP) gel and chloroxylenol 0.5% plus salicylic acid 2% (PCMX + SA) cream (Nisal cream) for efficacy and adverse reactions. Thirty-seven volunteers participated in the study, 19 in the BP group and 18 in the PCMX + SA group. The patients applied the medication twice daily to the entire face. Clinical evaluation and lesion counts were obtained at 0, 3, 6, 9 and 12 weeks. At week 12 both groups showed a marked improvement in both inflammatory and noninflammatory lesions (60% and 54% for the BP group and 62% and 56% for and 56% for the PCMX + SA group, respectively). Although PCMX + SA showed a slightly stronger keratolytic effect throughout the study period, there was no statistically significant difference in the reduction of the papulopustules or comedones between the two groups. Adverse effects such as erythema and photosensitivity were significantly fewer in the PCMX + SA group at week 12 (p = 0.0002 and p = 0.05, respectively). These results suggest that PCMX + SA cream is as effective as BP gel in the treatment of papulopustular and comedonal acne and that it is better tolerated.

  3. Sensitive quantitation of polyamines in plant foods by ultrasound-assisted benzoylation and dispersive liquid-liquid microextraction with the aid of experimental designs.

    PubMed

    Pinto, Edgar; Melo, Armindo; Ferreira, Isabel M P L V O

    2014-05-14

    A new method involving ultrasound-assisted benzoylation and dispersive liquid-liquid microextraction was optimized with the aid of chemometrics for the extraction, cleanup, and determination of polyamines in plant foods. Putrescine, cadaverine, spermidine, and spermine were derivatized with 3,5-dinitrobenzoyl chloride and extracted by dispersive liquid-liquid microextraction using acetonitrile and carbon tetrachloride as dispersive and extraction solvents, respectively. Two-level full factorial design and central composite design were applied to select the most appropriate derivatization and extraction conditions. The developed method was linear in the 0.5-10.0 mg/L range, with a R(2) ≥ 0.9989. Intra- and interday precisions ranged from 0.8 to 6.9% and from 3.0 to 10.3%, respectively, and the limit of detection ranged between 0.018 and 0.042 μg/g of fresh weight. This method was applied to the analyses of six different types of plant foods, presenting recoveries between 81.7 and 114.2%. The method is inexpensive, versatile, simple, and sensitive.

  4. Separation and removal of Cu2+, Fe2+, and Fe3+ from environmental waste samples by N-benzoyl-n-phenylhydroxylamine.

    PubMed

    Sarode, Dhananjay Bhaskar; Attarde, Sanjay Baliram; Ingle, Sopan Tukaram; Srivastava, Varsha; Sillanpää, Mika E T

    2015-01-01

    This study was conducted to determine the optimum extraction conditions for the effective separation and removal of Cu2+, Fe2+, and Fe3+ using N-benzoyl-n-phenylhydroxylamine (BPA) as an analytical reagent. An efficient liquid-liquid extraction method was developed for the separation and removal of Cu2+, Fe2+, and Fe3+ from environmental waste samples. In this method, BPA was used as a chelating agent and the effect of different parameters- including solvents, pH, stripping agents, extraction time, and the interference of other ions- on the quantitative removal of these metals was investigated. This study demonstrates that chloroform is the most effective solvent for BPA. The maximum extraction of the selected metallic species was found between pH 3 and 5. It was demonstrated that the maximum percentage recovery of the metals can be attained using 1 M HCl as a stripping agent. Optimized conditions of different parameters could be beneficial for industry and environmental laboratories.

  5. Recent advances in the use of adapalene 0.1%/benzoyl peroxide 2.5% to treat patients with moderate to severe acne.

    PubMed

    Leyden, James

    2016-01-01

    The central role of inflammation in acne is now more clearly understood. Adapalene, a third-generation topical retinoid, down-regulates toll-like receptor 2 expression and inhibits activator protein-1 activity. In a fixed-dose combination, adapalene and benzoyl peroxide (BPO) act synergistically on inflammatory patterns through regulation of innate immunity. In addition to reducing inflammatory and non-inflammatory lesions, adapalene/BPO helps prevent lesion and microcomedone formation. The combination of a topical retinoid and antimicrobial agent remains the preferred approach for almost all patients with acne. In cases of more severe disease, there is a clinical benefit in combining adapalene/BPO with an oral antibiotic for 12 weeks. Most recently, adapalene/BPO plus doxycycline 200 mg was found to be highly effective when compared with isotretinoin in the treatment of patients with severe acne with nodules. Long-term maintenance therapy is needed for most patients. Retinoids are the preferred agents, with BPO added in patients with more severe disease if needed. Adapalene is anticomedogenic, reduces comedones and has anti-inflammatory properties, while BPO is a unique antimicrobial agent not shown to induce microbial resistance after more than 50 years of use. Maintenance therapy for 6 months with adapalene/BPO prevents relapse among patients with severe acne and continues to reduce disease symptoms.

  6. Effects of Adapalene-Benzoyl Peroxide Combination Gel in Treatment or Maintenance Therapy of Moderate or Severe Acne Vulgaris: A Meta-Analysis

    PubMed Central

    Zhou, Rongying

    2014-01-01

    Background An antibiotic-free, fixed-dose combination gel with adapalene (A) 0.1% and benzoyl peroxide (BPO) 2.5% has been developed for treatment of acne vulgaris. Objective To compare the clinical outcomes of A-BPO combination gel with vehicle gel for treatment or maintenance therapy of patients with acne vulgaris. Methods An electronic search of the database PubMed (1966 to September 2012), Embase (1984 to September 2012), and Cochrane Controlled Trials Register (CENTRAL; 3rd Quarter, 2012) was undertaken to identify relevant studies. Main clinical outcomes were success rate, treatment-related adverse events (AEs), AEs leading to discontinuation, satisfaction with the effectiveness, and overall satisfaction. Results Six studies were finally included in this meta-analysis. The A-BPO group yielded better clinical outcomes regarding the success rate (p<0.00001), satisfaction with the effectiveness of treatment (p=0.005), and overall satisfaction (p=0.005) compared to the vehicle group. The incidence of treatment-related AEs in the A-BPO group was comparable with that of vehicle group (p=0.09), while the A-BPO group was associated with a slightly increase in the incidence of AEs leading to discontinuation when compared with the vehicle group (p=0.02). Conclusion A-BPO combination gel yields better clinical outcomes including success rate, satisfaction with the effectiveness, and overall satisfaction compared to vehicle gel, despite an increased incidence of AEs leading to discontinuation. The A-BPO combination agent most likely contributes to the treatment of moderate acne vulgaris rather than severe acne vulgaris, but it may be useful in maintenance therapy of patients with severe acne vulgaris. PMID:24648685

  7. Randomized tolerability analysis of clindamycin phosphate 1.2%-tretinoin 0.025% gel used with benzoyl peroxide wash 4% for acne vulgaris.

    PubMed

    Draelos, Zoe Diana; Potts, Aaron; Alió Saenz, Alessandra B

    2010-12-01

    The multiple etiologic factors involved in acne vulgaris make the use of several medications necessary to treat the condition. Use of a fixed combination of clindamycin phosphate 1.2% and tretinoin 0.025% in conjunction with a benzoyl peroxide (BPO) wash 4% targets several pathologic factors simultaneously and mitigates the potential for clindamycin-induced Propionibacterium acnes-resistant strains. New formulations may allow such regimens to be effectively used without overly reduced tolerability resulting from the irritation potential of tretinoin and BPO. This randomized, single-blind study investigated the local tolerability, irritation potential, and safety of an aqueous-based gel (clindamycin phosphate 7.2%-tretinoin 0.025% [CT gel]) when used in conjunction with a BPO wash 4% in participants with mild to moderate acne vulgaris. Participants applied the CT gel once daily in the evening for 4 weeks in conjunction with once-daily morning use of either BPO wash 4% or nonmedicated soap-free cleanser lotion (SFC). Local tolerability and irritation potential were assessed by participants and investigators using separate 6-point scales. The frequency and severity of dryness, scaling, erythema, burning/stinging, and itching increased during the first week of treatment in both treatment arms but decreased thereafter. Local tolerability reactions were slightly more frequent in the CT gel + BPO wash group versus the CT gel + SFC group at week 1 but were generally mild and improved within 1 to 2 weeks. In conclusion, therapy with CT gel + BPO wash appears safe and well-tolerated in participants with mild to moderate acne vulgaris.

  8. Dinuclear manganese(II) complexes of hexaazamacrocycles bearing N-benzoylated pendant separated by aromatic spacers: Antibacterial, DNA interaction, cytotoxic and molecular docking studies.

    PubMed

    Arthi, P; Shobana, S; Srinivasan, P; Prabhu, D; Arulvasu, C; Kalilur Rahiman, A

    2015-12-01

    Three new homodinuclear manganese(II) complexes of the type [Mn2L(1-3)(ClO4)(H2O)](ClO4)3 (1-3) have been synthesized via cyclocondensation of terephthalaldehyde with three different benzoylated pendants in the presence of manganese(II) perchlorate and characterized by spectroscopic methods. Cyclic voltammetric investigation of complexes (1-3) depict two quasi-reversible one electron reduction processes in the cathodic potential region (E(1)pc=-0.73 to-0.83 V, E(2)pc=-1.31 to -1.40 V) and two quasi-reversible one electron oxidation processes in the anodic potential region (E(1)pa=1.03 to 1.10 V, E(2)pa=1.69 to 1.77 V). Electronic absorption spectra of the complexes suggested tetrahedral geometry around the central metal ion. The observed low magnetic moment values (μeff, 5.60-5.68 B.M.) of the complexes indicate the presence of an antiferromagnetic spin-exchange interaction between two metal centers, which was also supported by the broad EPR signal. All the compounds were tested for antibacterial activity against Gram (-ve) and Gram (+ve) bacterial strains. The binding studies of complexes with CT-DNA suggested minor-groove mode of interaction. Molecular docking studies were carried out in order to find the binding affinity of complexes with DNA and protein EGFR Kinase. The complexes are stabilized by additional electrostatic and van der Waals interaction with the DNA, and support minor groove mode of binding. The cleavage activity of complexes on pBR322 plasmid DNA displays efficient activity through a mechanistic pathway involving hydroxyl radicals. The cytotoxicity of complexes 2 and 3 have been tested against human liver adenocarcinoma (HepG2) cell line. Nuclear-chromatin cleavage has also been observed with propidium iodide (PI) staining and alkaline single-cell gel electrophoresis (comet assay) techniques.

  9. Metal complexes of the nanosized ligand N-benzoyl-N‧-(p-amino phenyl) thiourea: Synthesis, characterization, antimicrobial activity and the metal uptake capacity of its ligating resin

    NASA Astrophysics Data System (ADS)

    Elhusseiny, Amel F.; Eldissouky, Ali; Al-Hamza, Ahmed M.; Hassan, Hammed H. A. M.

    2015-11-01

    The new nanosized N-benzoyl-N‧-(p-amino phenyl) thiourea ligand H2L was synthesized by nanoprecipitation method. The [Cu (H2L)2 Cl]·2H2O, [Zn (H2L)2(OAc)2], [Cd (H2L)2Cl2] and [Hg (H2L)2Cl2] complexes were synthesized and characterized by various physicochemical methods. Results revealed that the ligand act as hypodentate and bonded to the metal ion via the sulfur atom forming mononuclear non-electrolyte diamagnetic complex. Magnetic moment results indicated a reduction of Cu (II) to Cu (I) during the coordination process. Thermal studies demonstrated variable stabilities of the complexes and [Zn (H2L)2(OAc)2] exhibited the highest thermal stability while [Hg (H2L)2Cl2] was volatile. The prepared compounds were screened against different pathogenic microorganisms. The ligand performed high antibacterial activity against certain bacterial strain compared to its complexes, and the standard bacteriocide in use. The ligand was successfully immobilized on modified Amberlite XAD-16 forming the hypodentate ligating resin PS-SO2-H2L. The new resin was characterized and the extent of metal adsorption reached maximum at pH 6.0 for Cu (II), Cd (II) and Ag (I), with an adsorption amount of 4.3, 4.0 and 3.7 mmol g-1 respectively. The nanosized H2L represents a new category of promising adsorbent that would have a practical impact on biological and water treatment applications.

  10. Synthesis and photoluminescence properties of silver(I) complexes based on N-benzoyl-L-glutamic acid and N-donor ligands with different flexibility

    NASA Astrophysics Data System (ADS)

    Yan, Ming-Jie; Feng, Qi; Song, Hui-Hua

    2016-05-01

    By changing the N-donor ancillary ligand, three novel silver (I) complexes {[Ag(HbzgluO) (4,4‧-bipy)]·H2O}n (1), {[Ag2(HbzgluO)2 (bpe)2]·2H2O}n (2) and {[Ag(HbzgluO)(bpp)]·2H2O}n (3) (H2bzgluO = N-benzoyl-L-glutamic acid, 4,4‧-bipy = 4,4ˊ-bipyridine, bpe = 1,2-di(4-pyridyl)ethane, bpp = 1,3-di(4-pyridyl)propane) were synthesized. Their structures have been determined by single-crystal X-ray diffraction analyses and further characterized by elemental analyses, IR spectra, powder X-ray diffraction (PXRD), and thermogravimetric analyses (TGA). In this study, the N-donor ligands are changed from rigidity (4,4‧-bipy), quasi-flexibility (bpe) to flexibility (bpp), the structures of complexes also change. Complex 1 features a 1D chain structure which is further linked together to construct a 2D supramolecular structure through hydrogen bonds. Complex 2 is a 1D double-chains configuration which eventually forms a 3D supramolecular network via hydrogen bonding interactions. Whereas, complex 3 exhibits a 2D pleated grid structure which is linked by hydrogen bonding interactions into a 3D supramolecular network. The present observations demonstrate that the modulation of coordination polymers with different structures can accomplish by changing the spacer length of N-donor ligands. In addition, the solid-state circular dichroism (CD) spectra indicated that compound 2 exhibited negative cotton effect which originated from the chiral ligands H2bzgluO and the solid-state fluorescence spectra of the three complexes demonstrated the auxiliary ligands have influence on the photoluminescence properties of the complexes.

  11. Diverse Cd(II) compounds based on N-benzoyl-L-glutamic acid and N-donor ligands: Structures and photoluminescent properties

    NASA Astrophysics Data System (ADS)

    Ma, Ning; Guo, Wei-Ying; Song, Hui-Hua; Yu, Hai-Tao

    2016-01-01

    Five new Cd(II) coordination polymers with N-benzoyl-L-glutamic acid (H2bzgluO) and different N-donor ligands, [Cd(bzgluO)(2,2‧-bipy)(H2O)]n (1), [Cd(bzgluO)(2,4‧-bipy)2(H2O)·3H2O]n (2), [Cd(bzgluO)(phen)·H2O]n (3), [Cd(bzgluO)(4,4‧-bipy)(H2O)]n (4), [Cd(bzgluO)(bpp)(H2O)·2H2O]n (5) were synthesized (2,2‧-bipy=2,2‧-bipyridine, 2,4‧-bipy=2,4‧-bipyridine, phen=1,10-phenanthroline, 4,4‧-bipy=4,4‧-bipyridine, bpp=1,3-di(4-pyridyl)propane). Compounds 1-2 exhibit a 1D single-chain structure. Compound 1 generates a 2D supramolecular structure via π-π stacking and hydrogen bonding, 3D architecture of compound 2 is formed by hydrogen bonding. Compound 3 features a 1D double-chain structure, which are linked by π-π interactions into a 2D supramolecular layer. Compounds 4-5 display a 2D network structure. Neighboring layers of 4 are extended into a 3D supramolecular architecture through hydrogen bonding. The structural diversity of these compounds is attributed to the effect of ancillary N-donor ligands and coordination modes of H2bzgluO. Luminescent properties of 1-5 were studied at room temperature. Circular dichroism of compounds 1, 2 and 5 were investigated.

  12. Randomized tolerability analysis of clindamycin phosphate 1.2%-tretinoin 0.025% gel used with benzoyl peroxide wash 4% for acne vulgaris.

    PubMed

    Draelos, Zoe Diana; Potts, Aaron; Alió Saenz, Alessandra B

    2010-12-01

    The multiple etiologic factors involved in acne vulgaris make the use of several medications necessary to treat the condition. Use of a fixed combination of clindamycin phosphate 1.2% and tretinoin 0.025% in conjunction with a benzoyl peroxide (BPO) wash 4% targets several pathologic factors simultaneously and mitigates the potential for clindamycin-induced Propionibacterium acnes-resistant strains. New formulations may allow such regimens to be effectively used without overly reduced tolerability resulting from the irritation potential of tretinoin and BPO. This randomized, single-blind study investigated the local tolerability, irritation potential, and safety of an aqueous-based gel (clindamycin phosphate 7.2%-tretinoin 0.025% [CT gel]) when used in conjunction with a BPO wash 4% in participants with mild to moderate acne vulgaris. Participants applied the CT gel once daily in the evening for 4 weeks in conjunction with once-daily morning use of either BPO wash 4% or nonmedicated soap-free cleanser lotion (SFC). Local tolerability and irritation potential were assessed by participants and investigators using separate 6-point scales. The frequency and severity of dryness, scaling, erythema, burning/stinging, and itching increased during the first week of treatment in both treatment arms but decreased thereafter. Local tolerability reactions were slightly more frequent in the CT gel + BPO wash group versus the CT gel + SFC group at week 1 but were generally mild and improved within 1 to 2 weeks. In conclusion, therapy with CT gel + BPO wash appears safe and well-tolerated in participants with mild to moderate acne vulgaris. PMID:21284283

  13. Copper(II) complexes with tridentate N-(benzoyl)-N‧-(salicylidine)-hydrazine and monodentate N-heterocycles: Investigations of intermolecular interactions in the solid state

    NASA Astrophysics Data System (ADS)

    Das, Sunirban; Pal, Samudranil

    2005-10-01

    Ternary copper(II) complexes having the general formula [Cu(bhs)(hc)], with a tridentate Schiff base, N-(benzoyl)- N'-(salicylidine)-hydrazine (H 2bhs) and monodentate N-heterocycles (hc=3,5-dimethylpyrazole, pyrazole, imidazole, and pyridine), are described. The complexes were characterized by elemental analysis, spectroscopic and cryomagnetic measurements and X-ray crystallography. Analytical data, infrared and electronic spectral features and molar conductivity values are consistent with the proposed molecular formula and the +2 oxidation state of the metal ion in these complexes. Cryomagnetic and EPR spectral measurements showed weak antiferromagnetic spin-exchange in all four complexes. In each complex, the metal ion is in N 2O 2 square-plane constituted by the phenolate-O, the imine-N, and the deprotonated amide-O donor bhs 2- and the sp 2 N-donor neutral heterocycle. In the solid state, the complexes having 3,5-dimethylpyrazole, imidazole, and pyridine as the heterocyclic ligand, exist as centrosymmetric dimeric species due to weak apical coordination of the metal bound phenolate-O. On the other hand, only one of the two molecules present in the asymmetric unit of the complex containing pyrazole forms the centrosymmetric dimeric species due to weak apical coordination of the metal bound amide-O. In the crystal lattice, intermolecular π-π, C-H⋯π, C-H⋯N, O-H⋯N and N-H⋯O interactions involving the complex and the solvent molecules lead to one- and two-dimensional supramolecular structures.

  14. Multicenter study for efficacy and safety evaluation of a fixeddose combination gel with adapalen 0.1% and benzoyl peroxide 2.5% (Epiduo® for the treatment of acne vulgaris in Brazilian population*

    PubMed Central

    Sittart, José Alexandre de Souza; da Costa, Adilson; Mulinari-Brenner, Fabiane; Follador, Ivonise; Azulay-Abulafia, Luna; de Castro, Lia Cândida Miranda

    2015-01-01

    BACKGROUND The current options for the treatment of acne vulgaris present many mechanisms of action. For several times, dermatologists try topical agents combinations, looking for better results. OBJECTIVES To evaluate the efficacy, tolerability and safety of a topical, fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel for the treatment of acne vulgaris in the Brazilian population. METHODS This is a multicenter, open-label and interventionist study. Patients applied 1.0 g of the fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel on the face, once daily at bedtime, during 12 weeks. Lesions were counted in all of the appointments, and the degree of acne severity, overall improvement, tolerability and safety were evaluated in each visit. RESULTS From 79 recruited patients, 73 concluded the study. There was significant, fast and progressive reduction of non-inflammatory, inflammatory and total number of lesions. At the end of the study, 75.3% of patients had a reduction of >50% in non-inflammatory lesions, 69.9% in inflammatory lesions and 78.1% in total number of lesions. Of the 73 patients, 71.2% had good to excellent response and 87.6% had satisfactory to good response. In the first week of treatment, erythema, burning, scaling and dryness of the skin were frequent complaints, but, from second week on, these signals and symptoms have reduced. CONCLUSION The fixed-dose combination of adapalene 0.1% and benzoyl peroxide 2.5% gel is effective, safe, well tolerated and apparently improves patient compliance with the treatment. PMID:27168522

  15. Comparison of clindamycin 1% and benzoyl peroxide 5% gel to a novel composition containing salicylic acid, capryloyl salicylic acid, HEPES, glycolic acid, citric acid, and dioic acid in the treatment of acne vulgaris.

    PubMed

    Baumann, Leslie S; Oresajo, Christian; Yatskayer, Margarita; Dahl, Amanda; Figueras, Kristian

    2013-03-01

    This study evaluated the tolerance and efficacy of 2 facial skin products in subjects with acne using the following acne treatments: 1) treatment A, a combination of salicylic acid, capryloyl salicylic acid, HEPES, glycolic acid, citric acid, and dioic acid, and 2) treatment B (BenzaClin®, clindamycin 1% and benzoyl peroxide 5% gel). The treatment design included the split-face application of treatment A and treatment B and the full-face application of the cleanser, moisturizer, and sunscreen. Data were collected through physician visual assessments, subject irritation questionnaires and assessments, along with clinical photography. Results showed similar tolerance and efficacy for both treatments.

  16. Determination of the tautomeric equilibria of pyridoyl benzoyl β-diketones in the liquid and solid state through the use of deuterium isotope effects on (1)H and (13)C NMR chemical shifts and spin coupling constants.

    PubMed

    Hansen, Poul Erik; Borisov, Eugeny V; Lindon, John C

    2015-02-01

    The tautomeric equilibria for 2-pyridoyl-, 3-pyridoyl-, and 4-pyridoyl-benzoyl methane have been investigated using deuterium isotope effects on (1)H and (13)C chemical shifts both in the liquid and the solid state. Equilibria are established both in the liquid and the solid state. In addition, in the solution state the 2-bond and 3-bond J((1)H-(13)C) coupling constants have been used to confirm the equilibrium positions. The isotope effects due to deuteriation at the OH position are shown to be superior to chemical shift in determination of equilibrium positions of these almost symmetrical -pyridoyl-benzoyl methanes. The assignments of the NMR spectra are supported by calculations of the chemical shifts at the DFT level. The equilibrium positions are shown to be different in the liquid and the solid state. In the liquid state the 4-pyridoyl derivative is at the B-form (C-1 is OH), whereas the 2-and 3-pyridoyl derivatives are in the A-form. In the solid state all three compounds are on the B-form. The 4-pyridoyl derivative shows unusual deuterium isotope effects in the solid, which are ascribed to a change of the crystal structure of the deuteriated compound. PMID:24070650

  17. Clindamycin and Benzoyl Peroxide Topical

    MedlinePlus

    ... these steps: Wash the affected area with warm water and gently pat dry with a clean towel. Use you fingertips to spread a thin layer of gel evenly over the affected area. Avoid getting the gel in your ... gel in your eyes, wash with warm water. Look in the mirror. If you see a ...

  18. Erythromycin and Benzoyl Peroxide Topical

    MedlinePlus

    ... doctor and pharmacist what prescription and nonprescription medications, vitamins, nutritional supplements, and herbal products you are taking. Be sure to mention other topical medications for acne. Your doctor may need to ...

  19. Fixed-Dose Combination Gel of Adapalene and Benzoyl Peroxide plus Doxycycline 100 mg versus Oral Isotretinoin for the Treatment of Severe Acne: Efficacy and Cost Analysis

    PubMed Central

    Penna, Pete; Meckfessel, Matthew H.; Preston, Norman

    2014-01-01

    Background Acne vulgaris is a chronic skin disease with a high prevalence. Left untreated or inadequately treated, acne vulgaris can lead to psychological and physical scarring, as well as to unnecessary medical expenses. Oral isotretinoin is an effective treatment for severe resistant nodular and conglobate acne vulgaris. A regimen consisting of a fixed-dose combination of adapalene and benzoyl peroxide gel, 0.1%/2.5% (A-BPO) with oral doxycycline 100 mg (A-BPO/D) has been demonstrated to be efficacious and well tolerated in patients with severe acne and may be an alternative to oral isotretinoin for some patients with severe acne. Objective The objective of this analysis was to compare the relative efficacy and associated costs of A-BPO/D versus oral isotretinoin. Methods In this analysis, comparisons of relative efficacy were made using previously published studies involving similar patient populations with severe acne that warrant the use of oral isotretinoin. The pricing for oral doxycycline and oral isotretinoin was estimated based on the maximum allowable cost from 9 states, and the pricing for A-BPO was calculated as the range between the average wholesale price and the wholesale acquisition cost. For this analysis, 2 treatment models were generated to compare costs: (1) a basic treatment model that examined the costs of an initial regimen of either A-BPO/D or oral isotretinoin without considering probable outcomes, and (2) a long-term model that factored in likely treatment outcomes and subsequent treatments into associated costs. The basic treatment model assumed that patients would be prescribed a single regimen of A-BPO/D for 12 weeks or oral isotretinoin for 20 weeks. The long-term model considered the probability of each treatment successfully managing patients' acne, as well as likely additional regimens of A-BPO monotherapy or an additional regimen of oral isotretinoin. As a result of different treatment durations, the costs for each treatment were

  20. Interaction of (4-hydroxyphenyl)pyruvate dioxygenase with the specific inhibitor 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione.

    PubMed

    Kavana, Michael; Moran, Graham R

    2003-09-01

    (4-Hydroxyphenyl)pyruvate dioxygenase (HPPD) is a non-heme Fe(II) enzyme that catalyzes the conversion of (4-hydroxyphenyl)pyruvate (HPP) to homogentisate as part of the tyrosine catabolism pathway. Inhibition of HPPD by the triketone 2-[2-nitro-4-(trifluoromethyl)benzoyl]-1,3-cyclohexanedione (NTBC) is used to treat type I tyrosinemia, a rare but fatal defect in tyrosine catabolism. Although triketones have been used for many years as HPPD inhibitors for both medical and herbicidal purposes, the mechanism of inhibition is not well understood. The following work provides mechanistic insight into NTBC binding. The tautomeric population of NTBC in aqueous solution is dominated by a single enol as determined by NMR spectroscopy. NTBC preferentially binds to the complex of HPPD and FeII [HPPD.Fe(II)] as evidenced by a visible absorbance feature centered at 450 nm. The binding of NTBC to HPPD.Fe(II) was observed using a rapid mixing method and was shown to occur in two phases and comprise three steps. A hyperbolic dependence of the first observable process with NTBC concentration indicates a pre-equilibrium binding step followed by a limiting rate (K(1) = 1.25 +/- 0.08 mM, k(2) = 8.2 +/- 0.2 s(-1)), while the second phase (k(3) = 0.76 +/- 0.02 s(-1)) had no dependence on NTBC concentration. Neither K(1),k(2), nor k(3) was influenced by pH in the range of 6.0-8.0. Isotope effects on both k(2) and k(3) were observed when D(2)O is used as the solvent (for k(2), k(h)/k(d) = 1.3; for k(3), k(h)/k(d) = 3.2). It is therefore proposed that the bidentate association of NTBC with the active site metal ion (k(2)) precedes the Lewis acid-assisted conversion of the bound enol to the enolate (k(3)). Although the native enzyme without substrate reacts with molecular oxygen to form the oxidized holoenzyme, the HPPD.Fe(II).NTBC complex does not. When the complex is exposed to atmospheric oxygen, the absorbance feature associated with NTBC binding does not diminish over the course of 2

  1. Crystal structure of bis­(μ-2-benzoyl­benzoato-κ2 O:O′)bis­[bis­(2,2′-bi­pyridine-κ2 N,N′)manganese(II)] bis­(perchlorate)

    PubMed Central

    Kani, Ibrahim

    2015-01-01

    The title compound, [Mn2(C6H5COC6H4COO)2(C10H8N2)4](ClO4)2, comprises a centrosymmetric binuclear cation and two perchlorate anions. In the complex cation, two MnII atoms are bridged by two O atoms of two different 2-benzoyl­benzoate ligands, each MnII atom being further coordinated by two 2,2′-bi­pyridine (bipy) ligands in a distorted octa­hedral environment. Within the binuclear mol­ecule, the Mn⋯Mn separation is 4.513 (7) Å. Inter­molecular C—H⋯O and C—H⋯ π inter­actions link the mol­ecules into a three-dimensional network. PMID:26870457

  2. Supra­molecular architecture in a co-crystal of the N(7)—H tautomeric form of N 6-benzoyl­adenine with adipic acid (1/0.5)

    PubMed Central

    Swinton Darious, Robert; Thomas Muthiah, Packianathan; Perdih, Franc

    2016-01-01

    The asymmetric unit of the title co-crystal, C12H9N5O·0.5C6H10O4, consists of one mol­ecule of N 6-benzoyl­adenine (BA) and one half-mol­ecule of adipic acid (AA), the other half being generated by inversion symmetry. The dihedral angle between the adenine and phenyl ring planes is 26.71 (7)°. The N 6-benzoyl­adenine mol­ecule crystallizes in the N(7)—H tautomeric form with three non-protonated N atoms. This tautomeric form is stabilized by intra­molecular N—H⋯O hydrogen bonding between the carbonyl (C=O) group and the N(7)—H hydrogen atom on the Hoogsteen face of the purine ring, forming an S(7) ring motif. The two carboxyl groups of adipic acid inter­act with the Watson–Crick face of the BA mol­ecules through O—H⋯N and N—H⋯O hydrogen bonds, generating an R 2 2(8) ring motif. The latter units are linked by N—H⋯N hydrogen bonds, forming layers parallel to (10-5). A weak C—H⋯O hydrogen bond is also present, linking adipic acid mol­ecules in neighbouring layers, enclosing R 2 2(10) ring motifs and forming a three-dimensional structure. C=O⋯π and C—H⋯π inter­actions are also present in the structure. PMID:27308047

  3. Solid state structure and solution thermodynamics of three-centered hydrogen bonds (O∙∙∙H∙∙∙O) using N-(2-benzoyl-phenyl) oxalyl derivatives as model compounds.

    PubMed

    Gómez-Castro, Carlos Z; Padilla-Martínez, Itzia I; García-Báez, Efrén V; Castrejón-Flores, José L; Peraza-Campos, Ana L; Martínez-Martínez, Francisco J

    2014-09-12

    Intramolecular hydrogen bond (HB) formation was analyzed in the model compounds N-(2-benzoylphenyl)acetamide, N-(2-benzoylphenyl)oxalamate and N1,N2-bis(2-benzoylphenyl)oxalamide. The formation of three-center hydrogen bonds in oxalyl derivatives was demonstrated in the solid state by the X-ray diffraction analysis of the geometric parameters associated with the molecular structures. The solvent effect on the chemical shift of H6 [δH6(DMSO-d6)-δH6(CDCl3)] and Δδ(ΝΗ)/ΔT measurements, in DMSO-d6 as solvent, have been used to establish the energetics associated with intramolecular hydrogen bonding. Two center intramolecular HB is not allowed in N-(2-benzoylphenyl)acetamide either in the solid state or in DMSO-d6 solution because of the unfavorable steric effects of the o-benzoyl group. The estimated ΔHº and ΔSº values for the hydrogen bonding disruption by DMSO-d6 of 28.3(0.1) kJ·mol-1 and 69.1(0.4) J·mol-1·K-1 for oxalamide, are in agreement with intramolecular three-center hydrogen bonding in solution. In the solid, the benzoyl group contributes to develop 1-D and 2-D crystal networks, through C-H∙∙∙A (A = O, π) and dipolar C=O∙∙∙A (A = CO, π) interactions, in oxalyl derivatives. To the best of our knowledge, this is the first example where three-center hydrogen bond is claimed to overcome steric constraints.

  4. Efficacy and safety of a ceramide containing moisturizer followed by fixed-dose clindamycin phosphate 1.2%/benzoyl peroxide 2.5% gel in the morning in combination with a ceramide containing moisturizer followed by tretinoin 0.05% gel in the evening for the treatment of facial acne vulgaris.

    PubMed

    Zeichner, Joshua A; Patel, Rita V; Haddican, Madelaine; Wong, Vicky

    2012-06-01

    Combination therapy addressing multiple pathogenic factors should be used to achieve optimal outcomes in treating acne. The following study demonstrated both safety and efficacy of fixed-dose clindamycin phosphate 1.2%/benzoyl peroxide 2.5% in the morning with micronized tretinoin 0.05% gel in the evening. Both products were applied to the skin following the use of a ceramide containing moisturizing lotion.

  5. Characterization of the residues modified when F sub 1 - ATPases are inactivated by 7-chloro-4-nitrobenzofurazan and 5 prime -(p-(fluorosulfonyl)benzoyl)-1,N sup 6 -ethenoadenosine

    SciTech Connect

    Verburg, J.G.

    1989-01-01

    Inactivation of the F{sub 1}-ATPases isolated from spinach chloroplasts (CF{sub 1}) and from the plasma membrane of the thermophilic bacterium, PS3 (TF{sub 1}) with 7-chloro-4-nitrobenzofurazan (Nbf-Cl) results in modification of Tyr-{beta}-328 and Tyr-{beta}-307, respectively. These residues are homologous to Tyr-{beta}-311 of the F{sub 1}-ATPase isolated from beef heart mitochondria, previously identified as the residue derivatized during inactivation of that enzyme with Nbf-Cl. Interestingly, an intramolecular migration of the Nbf- moiety from the tyrosine residue to a nearby lysine residue, observed when MF{sub 1} and TF{sub 1} which had been inactivated with Nbf-Cl are incubated at alkaline pH, was not observed when CF{sub 1} was treated in the same manner. CF{sub 1} differs from other ATPases in that it contains ADP, tightly bound at a single catalytic site. It is possible that this tightly bound ADP prevents migration of the Nbf moiety. The characteristics of inactivation of MF{sub 1} with the fluorosulfonyl benzoyl derivatives of adenosine (FSBA) and inosine (FSBI) have been described in the literature. Inactivation of MF{sub 1} with FSBA results in the mutually exclusive modification of Tyr-368 or His-427 in all three copies of the {beta} subunit. These residues comprise part of the noncatalytic nucleotide binding site. Inactivation of MF{sub 1} with FSBI results in modification of Tyr-{beta}-345 in a single catalytic site. The fluorosulfonyl benzoyl derivative of 1,N{sup 6}-ethenoadenosine (FSB{epsilon}A) has been prepared, and the characteristics and selectivity of modification of MF{sub 1} with this reagent are presented. FSB{epsilon}A binds reversibly to MF{sub 1} with an apparent dissociation constant of 250 {mu}M before covalent modification. The residue in MF{sub 1} that reacts with FSB{epsilon}A exhibits an apparent pK{sub a} of 8.9.

  6. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-Dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and Tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C.; Smith, B.F.

    1992-07-01

    The first measurements of distribution coefficients (k{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}`s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}`s for these actinides are about about a factor of 10 greater than the K{sub d}`s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}`s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand. 9 refs., 2 figs., 1 tab.

  7. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C. California Univ., Berkeley, CA . Dept. of Chemistry); Smith, B.F. )

    1991-11-01

    The first measurements of distribution coefficients (K{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}'s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}'s for these actinides are about a factor of 5 to 10 greater than the K{sub d}'s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}'s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand.

  8. Extraction studies of selected actinide ions from aqueous solutions with 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione and tri-n-octylphosphine oxide

    SciTech Connect

    Hannink, N.J.; Hoffman, D.C. |; Smith, B.F.

    1991-11-01

    The first measurements of distribution coefficients (K{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}`s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}`s for these actinides are about a factor of 5 to 10 greater than the K{sub d}`s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}`s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand.

  9. Simple and sensitive high-performance liquid chromatographic determination of methamphetamines in human urine as derivatives of 4-(4,5-diphenyl-1H-imidazol-2-yl) benzoyl chloride, a new fluorescence derivatization reagent.

    PubMed

    Al-Dirbashi, O; Qvarnstrom, J; Irgum, K; Nakashima, K

    1998-08-01

    A simple, rapid and highly sensitive high-performance liquid chromatographic method for the determination of methamphetamine and its metabolites in human urine was developed. Without tedious pretreatment procedures, aliquots of methamphetamine spiked or abusers' urine samples were simply acidified, dried under a stream of N2 gas, and then derivatized with 4-(4,5-diphenyl-1H-imidazol-2-yl) benzoyl chloride in acetonitrile in the presence of traces of triethylamine. Five derivatives were isocratically separated within 33 min by an ODS column, and the effluent was monitored at 440 nm (lambda(ex), 330 nm). Using 1-phenylethylamine as an internal standard calibration curves were confirmed to be linear up to at least 2x10(-5) M in urine with correlation coefficients of 0.998-1.000, while the detection limits at S/N=3 were 0.6-5.2 fmol per 5-microl injection. The relative standard deviations (n=5) of inter- and intra-day variations were less than 8.9%. The correlation between the concentrations of methamphetamine and amphetamine in urine determined by the proposed method and another currently accepted one was satisfactory. The method was successfully applied to urine samples collected from methamphetamine addicts.

  10. Comparison of the benzoyl-DL-arginine-naphthylamide (BANA) test, DNA probes, and immunological reagents for ability to detect anaerobic periodontal infections due to Porphyromonas gingivalis, Treponema denticola, and Bacteroides forsythus.

    PubMed Central

    Loesche, W J; Lopatin, D E; Giordano, J; Alcoforado, G; Hujoel, P

    1992-01-01

    Most forms of periodontal disease are associated with the presence or overgrowth of anaerobic species that could include Treponema denticola, Porphyromonas gingivalis, and Bacteroides forsythus among others. These three organisms are among the few cultivable plaque species that can hydrolyze the synthetic trypsin substrate benzoyl-DL-arginine-naphthylamide (BANA). In turn, BANA hydrolysis by the plaque can be associated with periodontal morbidity and with the presence of these three BANA-positive organisms in the plaque. In this investigation, the results of the BANA test, which simultaneously detects one or more of these organisms, were compared with the detection of these organisms by (i) highly specific antibodies to P. gingivalis, T. denticola, and B. forsythus; (ii) whole genomic DNA probes to P. gingivalis and T. denticola; and (iii) culturing or microscopic procedures. The BANA test, the DNA probes, and an enzyme-linked immunosorbent assay or an indirect immunofluorescence assay procedure exhibited high sensitivities, i.e., 90 ot 96%, and high accuracies, i.e., 83 to 92%, in their ability to detect combinations of these organisms in over 200 subgingival plaque samples taken from the most periodontally diseased sites in 67 patients. This indicated that if P. gingivalis, T. denticola, and B. forsythus are appropriate marker organisms for an anaerobic periodontal infection, then the three detection methods are equally accurate in their ability to diagnose this infection. The same statement could not be made for the culturing approach, where accuracies of 50 to 62% were observed. PMID:1311335

  11. Study of Nα-benzoyl-L-argininate ethyl ester chloride, a model compound for poly(ester amide) precursors: X-ray diffraction, infrared and Raman spectroscopies, and quantum chemistry calculations

    NASA Astrophysics Data System (ADS)

    Fonseca, A. C.; Jarmelo, S.; Silva, M. Ramos; Beja, A. M. Matos; Fausto, R.; Gil, M. H.; Simões, P. N.

    2011-03-01

    Poly(ester amide)s (PEAs) are lacking in structural and spectroscopic information. This paper reports a structural and spectroscopic characterization of Nα-benzoyl-L-argininate ethyl ester chloride (BAEEH+.Cl-), an important amino acid derivative and an adequate PEAs' model compound. Crystals of BAEEH+.Cl- obtained by slow evaporation in an ethanol/water mixture were studied by different complementary techniques. X-ray analysis shows that BAEEH+.Cl- crystallizes in the chiral space group P21. There are two symmetry independent cations (and anions) in the unit cell. The two cations have different conformations: in one of them, the angle between the least-squares planes of the phenyl ring and the guanidyl group is 5.1(2)°, and in the other the corresponding angle is 13.3(2)°. There is an extensive network of H-bonds that assembles the ions in layers parallel to the ab plane. Experimental FT-IR and Raman spectra of BAEEH+.Cl- were recorded at room temperature in the 3750-600 cm-1 and 3380-100 cm-1 regions, respectively, and fully assigned. Both structural and spectroscopic analysis were supported by quantum chemistry calculations based on different models (in vacuo and solid-state DFT simulations).

  12. Synthesis, crystal structure analysis, spectral IR, NMR UV-Vis investigations, NBO and NLO of 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide with use of X-ray diffractions studies along with DFT calculations

    NASA Astrophysics Data System (ADS)

    Demir, Sibel; Sarioğlu, Ahmet Oral; Güler, Semih; Dege, Necmi; Sönmez, Mehmet

    2016-08-01

    The title compound, 2-benzoyl-N-(4-chlorophenyl)-3-oxo-3-phenylpropanamide compound (C22H16NO3Cl) has been synthesized and characterized by X-ray diffraction, IR, 1H and 13C NMR and UV-Vis spectra. Optimized geometrical structure, harmonic vibrational frequencies and chemical shifts were computed using hybrid-DFT (B3LYP and B3PW91) methods and 6-311G(d,p) as the basis set. The results of the optimized molecular structure are presented and compared with the experimental X-ray diffraction. The calculated optimized geometries, vibrational frequencies and 1H NMR chemical shift values are in strong agreement with experimentally measured values. UV-Vis spectrum of the title compound, was also recorded and the electronic properties, such as calculated energies, excitation energies, oscillator strengths, dipole moments and frontier orbital energies and band gap energies were computed with TDDFT-B3LYP methodolgy and using 6-311G(d,p) as the basis set. Furthermore, frontier molecular orbitals (FMO), molecular electrostatic potential (MEP), natural bond orbital (NBO) and non linear optical (NLO) properties were performed by using B3LYP/6-311G(d,p) level for the title compound.

  13. When do efficacy outcomes in clinical trials correlate with clinical relevance? analysis of clindamycin phosphate 1.2%-benzoyl peroxide 3.75% gel in moderate to severe acne vulgaris.

    PubMed

    Del Rosso, James Q

    2016-07-01

    Acne vulgaris (AV) is a common skin disease that is challenging to successfully treat due to its complex underlying pathophysiology and chronicity. Unrealistic expectations based on the desire for rapid and complete clearance or local tolerability reactions related to topical medications often lead to incomplete adherence with therapy, premature treatment cessation, and poor therapeutic outcomes. Despite stressing to patients the importance of compliance and the lag time of several weeks before visible improvement may be noted with treatments for AV, data on evaluation of the time taken to achieve a clinically meaningful improvement of AV that may be perceived by clinicians and patients are limited. Clindamycin phosphate 1.2%-benzoyl peroxide 3.75% (clindamycin-BP 3.75%) gel has been shown in pivotal trials to be effective and well tolerated in patients with moderate to severe AV. This article reviews a new concept referred to as time to onset of action (TOA), which is described in detail and illustrated using the pivotal trial data with clindamycin-BP 3.75% gel for treatment of AV. PMID:27529706

  14. Synthesis, Characterization And Antitumor Activity Of Copper(II) Complexes, [CuL2] [HL1-3=N,N-Diethyl-N'-(R-Benzoyl)Thiourea (R=H, o-Cl and p-NO2)

    PubMed Central

    Hernández, Wilfredo; Beyer, Lothar; Schröder, Uwe; Richter, Rainer; Ferreira, Jorge; Pavani, Mario

    2005-01-01

    The copper (II) complexes (CuL2) were prepared by reaction of Cu(CH3COO)2 with the corresponding derivatives of acylthioureas in a Cu:HL molar ratio of 1:2. Acylthiourea ligands, N,N-diethyl-N'-(R-benzoyl) thiourea (HL1-3) [R=H, o-Cl and p-NO2] were synthesized in high yield (78-83%) and characterized by elemental analysis, infrared spectroscopy, 1H and 13C NMR spectroscopy. The complexes CuL2 were characterized by elemental analysis, IR, FAB(+)-MS, magnetic susceptibility measurements, EPR and cyclic voltammetry. The crystal structure of the complex Cu(L2)2 shows a nearly square-planar geometry with two deprotonated ligands (L) coordinated to CuII through the oxygen and sulfur atoms in a cis arrangement. The antitumor activity of the copper(II) complexes with acylthiourea ligands was evaluated in vitro against the mouse mammary adenocarcinoma TA3 cell line. These complexes exhibited much higher cytotoxic activity (IC50 values in the range of 3.9-6.9 μM) than their corresponding ligands (40-240 μM), which indicates that the coordination of the chelate ligands around the CuII enhances the antitumor activity and, furthermore, this result confirmed that the participation of the nitro and chloro substituent groups in the complex activities is slightly relevant. The high accumulation of the complexes Cu(L2)2 and Cu(L3)2 in TA3 tumor cells and the much faster binding to cellular DNA than Cu(L1)2 are consistent with the in vitro cytotoxic activities found for these copper complexes. PMID:18365106

  15. Spiro-oxindole derivative 5-chloro-4',5'-diphenyl-3'-(4-(2-(piperidin-1-yl) ethoxy) benzoyl) spiro[indoline-3,2'-pyrrolidin]-2-one triggers apoptosis in breast cancer cells via restoration of p53 function.

    PubMed

    Saxena, Ruchi; Gupta, Garima; Manohar, Murli; Debnath, Utsab; Popli, Pooja; Prabhakar, Yenamandra S; Konwar, Rituraj; Kumar, Sandeep; Kumar, Atul; Dwivedi, Anila

    2016-01-01

    Breast cancer remains a significant health problem due to the involvement of multiple aberrant and redundant signaling pathways in tumorigenesis and the development of resistance to the existing therapeutic agents. Therefore, the search for novel chemotherapeutic agents for effective management of breast cancer is still warranted. In an effort to develop new anti-breast cancer agents, we have synthesized and identified novel spiro-oxindole derivative G613 i.e. 5-chloro-4',5'-diphenyl-3'-(4-(2-(piperidin-1-yl) ethoxy) benzoyl) spiro[indoline-3,2'-pyrrolidin]-2-one, which has shown growth inhibitory activity in breast cancer cells. The present study was aimed to explore the mechanism of anti-tumorigenic action of this newly identified spiro-oxindole compound. Compound G613 inhibited the Mdm2-p53 interaction in breast cancer cells and tumor xenograft. It caused restoration of p53 function by activating its promoter activity, triggering its nuclear accumulation and preventing its ubiquitination and proteasomal degradation. Supportively, molecular docking studies revealed considerable homology in the docking mode of G613 and the known Mdm2 inhibitor Nutlin-3, to p53 binding pocket of Mdm2. The activation of p53 led to upregulation of p53 dependent pro-apoptotic proteins, Bax, Pumaα and Noxa and enhanced interaction of p53 with bcl2 member proteins thus triggering both transcription-dependent and transcription-independent apoptosis, respectively. Additionally, the compound decreased estrogen receptor activity through sequestration of estrogen receptor α by p53 thereby causing a decreased transcriptional activation and expression of proliferation markers. In conclusion, G613 represents a potent small-molecule inhibitor of the Mdm2-p53 interaction and can serve as a promising lead for developing a new class of anti-cancer therapy for breast cancer patients.

  16. Cross-sectional Pilot Study of Antibiotic Resistance in Propionibacterium Acnes Strains in Indian Acne Patients Using 16S-RNA Polymerase Chain Reaction: A Comparison Among Treatment Modalities Including Antibiotics, Benzoyl Peroxide, and Isotretinoin

    PubMed Central

    Sardana, Kabir; Gupta, Tanvi; Kumar, Bipul; Gautam, Hemant K; Garg, Vijay K

    2016-01-01

    Background: Antibiotic resistance is a worldwide problem in acne patients due to regional prescription practices, patient compliance, and genomic variability in Propionibacterium acnes, though the effect of treatment on the resistance has not been comprehensively analyzed. Aims: Our primary objective was to assess the level of antibiotic resistance in the Indian patients and to assess whether there was a difference in the resistance across common treatment groups. Subjects and Methods: A cross-sectional, institutional based study was undertaken and three groups of patients were analyzed, treatment naïve, those on antibiotics and patients on benzoyl peroxide (BPO) and/isotretinoin. The follicular content was sampled and the culture was verified with 16S rRNA polymerase chain reaction, genomic sequencing, and pulsed-field gel electrophoresis. Minimum inhibitory concentration (MIC) assessment was done for erythromycin (ERY), azithromycin (AZI), clindamycin (CL), tetracycline (TET), doxycycline (DOX), minocycline (MINO), and levofloxacin (LEVO). The four groups of patients were compared for any difference in the resistant strains. Results: Of the 52 P. acnes strains isolated (80 patients), high resistance was observed to AZI (100%), ERY (98%), CL (90.4%), DOX (44.2%), and TETs (30.8%). Low resistance was observed to MINO (1.9%) and LEVO (9.6%). Statistical difference was seen in the resistance between CL and TETs; DOX/LEVO and DOX/MINO (P < 0.001). High MIC90 (≥256 μg/ml) was seen with CL, macrolides, and TETs; moreover, low MIC90 was observed to DOX (16 μg/ml), MINO (8 μg/ml), and LEVO (4 μg/ml). Though the treatment group with isotretinoin/BPO had the least number of resistant strains there was no statistical difference in the antibiotic resistance among the various groups of patients. Conclusions: High resistance was seen among the P. acnes strains to macrolides-lincosamides (AZI and CL) while MINO and LEVO resistance was low. PMID:26955094

  17. Is benzoyl peroxide 3% topical gel effective and safe in the treatment of acne vulgaris in Japanese patients? A multicenter, randomized, double-blind, vehicle-controlled, parallel-group study.

    PubMed

    Kawashima, Makoto; Hashimoto, Hirofumi; Alio Sáenz, Alessandra B; Ono, Makoto; Yamada, Masahiro

    2014-09-01

    Benzoyl peroxide (BPO) as an anti-acne medication is not yet approved in Japan. This study evaluated the efficacy and safety of a once-daily topical application of BPO 3% gel versus an inert vehicle gel in Japanese acne patients. Three hundred and sixty patients were randomized to receive BPO 3% or vehicle for 12 weeks. The primary efficacy end-point was absolute change in number of total lesions (TL) from baseline to week 12 to demonstrate the superiority of BPO 3% versus vehicle. Secondary efficacy end-points were absolute and percent change in TL, inflammatory lesions (IL), non-inflammatory lesions (non-IL) and Investigator's Static Global Assessment (ISGA). Change in TL counts from baseline to week 12 for BPO 3% was superior to vehicle (difference, -21.0; P < 0.001). Absolute and percent reductions in TL, IL and non-IL counts were greater for BPO 3% at all study visits. The proportion of patients with improvement in ISGA scores was significantly higher with BPO 3% than with vehicle from week 2. All adverse events were mild or moderate. Adverse drug-related reactions were higher for BPO 3% (30%) than with vehicle (5%). Local tolerability scores of grade 1 or more (slight to moderate) were more frequent with BPO 3% than vehicle with the most significant differences observed in dryness (56% vs 27% at week 1-4), peeling (19% vs 9% at week 1-2) and burning/stinging (58% vs 15% at week 1-12). These results indicate that BPO 3% is effective while maintaining a favorable safety and tolerability profile in Japanese acne patients.

  18. Synthesis and Characterization of Ru(II) Tris(1,1O-phenanthroline)-Electron Acceptor Dyads Incorporating the 4-benzoyl-N-methylpyridinium Cation or N-Benzyl-N'-methyl-viologen. Improving the Dynamic Range, Sensitivity and Response Time of Sol-Gel Based Optical Oxygen Sensors

    NASA Technical Reports Server (NTRS)

    Leventis, Nicholas; Rawashdeh, Abdel-Monen M.; Elder, Ian A.; Yang, Jinhua; Dass, Amala; Sotiriou-Leventis, Chariklia

    2004-01-01

    The title compounds (1 and 2, above) were synthesized by Sonogashira coupling reactions of appropriate Ru(1I) complexes with the electron a cceptors. Characterization was conducted in solution and in frozen ma trices. Finally, the title compounds were evaluated as dopants of sol-gel materials. It was found that the intramolecular quenching efficie ncy of 4-benzoyl-Nmethylpyridinium cation in solution depends on the solvent: photoluminescence is quenched completely in CH,CN, but not i n methanol or ethanol. On the other hand, intramolecular emission que nching by 4-benzyl-N-methyl viologen is complete in all solvents. The difference between the two quenchers is traced electrochemically to t he solvation of the 4-benzoyl-Nmethylpyridiniums by alcohol. In froze n matrices or adsorbed on the surfaces of silica aerogel, both Ru(I1) complex/electron acceptor dyads of this study are photoluminescent, and the absence of quenching has been traced to the environmental rigi dity. When doped aerogels are cooled at 77 K, the emission intensity increases by approximately 4x, and the spectra shift to the blue, analogous to what is observed with Ru(I1) complexes in solutions undergoi ng fluid-to-rigid transition. However, in contrast to frozen solution s, the luminescent moieties in the bulk of aerogels kept at low tempe ratures are still accessible to gas-phase quenchers diffusing through the mesopores, leading to more sensitive platforms for sensors than o ther room-temperature configurations. Thus the photoluminescence of o ur Ru(I1) complex dyads adsorbed on aerogel is quenchable by O2 both at room temperature and at 77 K. Furthermore, it was also found that O 2 modulates the photoluminescence of aerogels doped with 4-benzoyl -N -methylpyridinium-based dyads over a wider dynamic range compared wi th aerogels doped with either our vislogen-based dyads or with Ru(I1) tris(1,lO-phenanthroline) itself.

  19. Formation of a dinuclear copper(II) complex through the cleavage of CN bond of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole

    SciTech Connect

    Shardin, Rosidah; Pui, Law Kung; Yamin, Bohari M.; Kassim, Mohammad B.

    2014-09-03

    A simple mononuclear octahedral copper(II) complex was attempted from the reaction of three moles of 1-benzoyl-3-(pyridin-2-yl)-1H-pyrazole and one mole of copper(II) perchlorate hexahydrate in methanol. However, the product of the reaction was confirmed to be a dinuclear copper(II) complex with μ-(3-(pyridin-2-yl)-pyrazolato) and 3-(pyridin-2-yl)-1H-pyrazole ligands attached to each of the Cu(II) centre atom. The copper(II) ion assisted the cleavage of the C{sub benzoyl}N bond afforded a 3-(pyridin-2-yl)-1H-pyrazole molecule. Deprotonation of the 3-(pyridin-2-yl)-1H-pyrazole gave a 3-(pyridin-2-yl)-pyrazolato, which subsequently reacted with the Cu(II) ion to give the (3-(pyridin-2-yl)-pyrazolato)(3-(pyridin-2-yl)-1H-pyrazole)Cu(II) product moiety. The structure of the dinuclear complex was confirmed by x-ray crystallography. The complex crystallized in a monoclinic crystal system with P2(1)/n space group and cell dimensions of a = 12.2029(8) Å, b = 11.4010(7) Å, c = 14.4052(9) Å and β = 102.414(2)°. The compound was further characterized by mass spectrometry, CHN elemental analysis, infrared and UV-visible spectroscopy and the results concurred with the x-ray structure. The presence of d-d transition at 671 nm (ε = 116 dm{sup 3} mol{sup −1} cm{sup −1}) supports the presence of Cu(II) centres.

  20. Development and Binding Mode Assessment of N-[4-[2-propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-L-γ-glutamyl-D-glutamic acid (BGC 945), a Novel Thymidylate Synthase Inhibitor that Targets Tumor Cells

    PubMed Central

    Tochowicz, Anna; Dalziel, Sean; Eidam, Oliv; O’Connell, Joseph D.; Griner, Sarah; Finer-Moore, Janet S.; Stroud, Robert M.

    2013-01-01

    N-[4-[2-propyn-1-yl[(6S)-4,6,7,8-tetrahydro-2-(hydroxymethyl)-4-oxo-3H-cyclopenta[g]quinazolin-6-yl]amino]benzoyl]-L-γ-glutamyl-D-glutamic acid 1 (BGC 945, now known as ONX 0801), is a small molecule thymidylate synthase (TS) inhibitor discovered at the Institute of Cancer Research in London. It is licensed by Onyx Pharmaceuticals and is in Phase 1 clinical studies. It is a novel antifolate drug resembling TS inhibitors plevitrexed and raltitrexed that combines enzymatic inhibition of thymidylate synthase with α-folate receptor-mediated targeting of tumor cells. Thus, it has potential for efficacy with lower toxicity due to selective intracellular accumulation through α-folate receptor (α-FR) transport. The α-FR, a cell-surface receptor glycoprotein, which is over expressed mainly in ovarian and lung cancer tumors, has an affinity for 1 similar to that for its natural ligand, folic acid. This study describes a novel synthesis of 1, an X-ray crystal structure of its complex with Escherichia coli TS and 2’-deoxyuridine-5’-monophosphate, and a model for a similar complex with human TS. PMID:23710599

  1. Structural, spectral, thermal and biological studies on (Z)-N-benzoyl-N‧-(2-oxo-2-(phenylamino)acetyl)carbamohydrazonothioic acid (H2PABT) and its Cd(II), Hg(II), Zn(II) and U(VI)O22+ complexes

    NASA Astrophysics Data System (ADS)

    Yousef, T. A.; Ahmed, Sara F.; El-Gammal, O. A.; Abu El-Reash, G. M.

    2015-07-01

    A new metal complexes formed by the reaction of (Z)-N-benzoyl-N‧-(2-oxo-2-(phenylamino)acetyl)carbamohydrazonothioic acid (H2PABT) and Cd(II), Hg(II), Zn(II) and U(VI)O22+ ions. The isolated complexes were prepared and characterized by conventional techniques. The IR data revealed that the ligand behaves as mononegative tridentate in Zn(II) and U(VI)O22+ complexes also, binegative tetradentate on Cd(II) and Hg(II) complexes. On the basis of magnetic and electronic spectral data an octahedral geometry for the U(VI)O22+ complex, a tetrahedral structure for the Cd(II), Zn(II) and Hg(II) complexes have been proposed. The IR spectrum of ligand which determined experimentally is compared with those obtained theoretically from DFT calculations. Also, the bond lengths, bond angles, HOMO, LUMO and dipole moments have been calculated. The calculated HOMO-LUMO energy gap reveals that charge transfer occurs within the ligand molecules. The calculated values of binding energies indicates the stability of complexes is higher that of ligand. Also, the kinetic and thermodynamic parameters for the different thermal degradation steps of the complexes were determined by Coats-Redfern and Horowitz-Metzger methods. Moreover, the ligand and its complexes were screened against Bacillus subtilis as Gram positive bacteria and Escherichia coli Gram negative bacteria using the inhibitory zone diameter. Also the antitumor activities of the ligand and its complexes have been evaluated against liver (HePG2) and breast (MCF-7) cancer cells. Out of all the synthesized compounds, [Hg2(PABT)Cl2(H2O)2] and [(UO2)(HPABT)(OAc)(H2O)] complexes showed high antibacterial activity with 55.5% while H2PABT showed the best cytotoxic effect on liver and breast cancer cells with IC50 2.10 and 5.91 of cytotoxicity respectively.

  2. Anti-diabetic and anti-adipogenic effects of a novel selective 11β-hydroxysteroid dehydrogenase type 1 inhibitor, 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone (KR-66344).

    PubMed

    Park, Ji Seon; Rhee, Sang Dal; Kang, Nam Sook; Jung, Won Hoon; Kim, Hee Youn; Kim, Jun Hyoung; Kang, Seung Kyu; Cheon, Hyae Gyeong; Ahn, Jin Hee; Kim, Ki Young

    2011-04-15

    The selective inhibitors of 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) have considerable potential for treating type 2 diabetes mellitus and metabolic syndrome. In the present study, we investigated the anti-diabetic and anti-adipogenic effects of 2-(3-benzoyl)-4-hydroxy-1,1-dioxo-2H-1,2-benzothiazine-2-yl-1-phenylethanone (KR-66344), as a 11β-HSD1 inhibitor; we also investigated the underlying molecular mechanisms in the cortisone-induced 3T3-L1 adipogenesis model system and C57BL/6-Lep(ob/ob) mice. KR-66344 concentration-dependently inhibited 11β-HSD1 activity in human liver microsome, mouse C2C12 myotube and human SW982 cells. In the C57BL/6-Lep(ob/ob) mice study, the administration of KR-66344 (200mg/kg/d, orally for 5 days) improved the glucose intolerance as determined by the oral glucose tolerance test, in which the area under the curve (AUC) of the plasma glucose concentration was significantly reduced by 27% compared with the vehicle treated group. Further, KR-66344 suppressed adipocyte differentiation on cortisone-induced adipogenesis in 3T3-L1 cells is associated with the suppression of the cortisone-induced mRNA levels of FABP4, G3PD, PPARγ2 and Glut4, and 11β-HSD1 expression and activity. Our results additionally demonstrate evidence showing that KR-66344 improved glycemic control and inhibited adipogenesis via 11β-HSD1 enzyme activity. Taken together, these results may provide evidence of the therapeutic potential of KR-66344, as a 11β-HSD1 inhibitor, in obesity and type 2 diabetes patients with metabolic syndrome.

  3. N-[[(Mercaptoacetyl)amino]benzoyl]glycines as mucolytic agents.

    PubMed

    Martin, T A; Comer, W T

    1985-07-01

    m- and p-aminobenzoic acids were converted to the title compounds by sequential use of ClCH2COCl, SOCl2, glycine methyl or ethyl ester, AcSK, and hydrolysis. The title compounds and a number of salts were compared for mucolytic activity, toxicity, stability, and hygroscopicity. When compared to N-acetyl-L-cysteine (NAC), the compounds exhibit several times the in vitro mucolytic activity of NAC on a molar basis. The most promising candidate appears to be the sodium salt 3.5H2O 2 of the meta series. PMID:4009614

  4. N-[[(Mercaptoacetyl)amino]benzoyl]glycines as mucolytic agents.

    PubMed

    Martin, T A; Comer, W T

    1985-07-01

    m- and p-aminobenzoic acids were converted to the title compounds by sequential use of ClCH2COCl, SOCl2, glycine methyl or ethyl ester, AcSK, and hydrolysis. The title compounds and a number of salts were compared for mucolytic activity, toxicity, stability, and hygroscopicity. When compared to N-acetyl-L-cysteine (NAC), the compounds exhibit several times the in vitro mucolytic activity of NAC on a molar basis. The most promising candidate appears to be the sodium salt 3.5H2O 2 of the meta series.

  5. Photocarcinogenesis promotion studies with benzoyl peroxide (BPO) and croton oil.

    PubMed

    Epstein, J H

    1988-08-01

    Previous studies demonstrated that BPO can promote chemically initiated tumor formation in SENCAR mice. In addition, a number of chemicals have been shown to promote and/or enhance UVR induced carcinogenesis. This study examined the effect of BPO on UVR initiated tumor formation. One hundred and forty-eight Uscd mice received 270 mJ/cm2 of UVB radiation to the posterior halves of their backs 3 times a week for 8 weeks. Four weeks later the mice were divided into 4 groups. Group I received croton oil in acetone applications to the back 5 times a week for the duration of the study. Group II received acetone, Group III received the BPO diluent, and Group IV received the BPO in an aqueous diluent applications as in Group I. One mouse in Group II (acetone) and one in Group IV (BPO) developed tumors in unirradiated skin. In the UVR initiated skin 38% of the survivors developed tumors in Group I (croton oil), whereas 5% did in Group II (acetone), 8% in Group III (BPO base), and 8% group IV (BPO). Thus under the circumstances of this study croton oil did promote UV initiated tumor formation but BPO did not. These results are consistent with those recently reported by Iversen.

  6. 9-Benzoyl 9-deazaguanines as potent xanthine oxidase inhibitors.

    PubMed

    Rodrigues, Marili V N; Barbosa, Alexandre F; da Silva, Júlia F; dos Santos, Deborah A; Vanzolini, Kenia L; de Moraes, Marcela C; Corrêa, Arlene G; Cass, Quezia B

    2016-01-15

    A novel potent xanthine oxidase inhibitor, 3-nitrobenzoyl 9-deazaguanine (LSPN451), was selected from a series of 10 synthetic derivatives. The enzymatic assays were carried out using an on-flow bidimensional liquid chromatography (2D LC) system, which allowed the screening¸ the measurement of the kinetic inhibition constant and the characterization of the inhibition mode. This compound showed a non-competitive inhibition mechanism with more affinity for the enzyme-substrate complex than for the free enzyme, and inhibition constant of 55.1±9.80 nM, about thirty times more potent than allopurinol. Further details of synthesis and enzymatic studies are presented herein.

  7. N′-Benzoyl-3-hydr­oxy-2-naphthohydrazide

    PubMed Central

    Liang, Qi-Feng; Feng, Hai-Mei; Li, Feng-Qing

    2008-01-01

    In the title compound, C18H14N2O3, the dihedral angle between the planes of the naphthalene and phenyl ring systems is 2.64 (2)°. Mol­ecules are engaged in π–π stacking (mean interplanar distance = 3.339 between naphthalene rings and 3.357 Å between benzene rings )and hydrogen-bonding inter­actions. PMID:21202534

  8. (±)-trans-3-Benzoyl-bicyclo-[2.2.2]octane-2-carboxylic acid.

    PubMed

    Lalancette, Roger A; Thompson, Hugh W; Brunskill, Andrew P J

    2008-01-01

    The title keto acid, C(16)H(18)O(3), displays significant twisting of all three ethyl-ene bridges in its bicyclo-[2.2.2]octane structure owing to steric inter-actions; the bridgehead-to-bridgehead torsion angles are 13.14 (12), 13.14 (13) and 9.37 (13)°. The compound crystallizes as centrosymmetric carboxyl dimers [O⋯O = 2.6513 (12) Å and O-H⋯O = 178°], which have two orientations within the cell and contain no significant carboxyl disorder. PMID:21201657

  9. Absorption spectroscopic study of synergistic extraction of praseodymium with benzoyl acetone in presence of crown ether.

    PubMed

    Banerjee, Shrabanti; Bhattacharya, Sumanta; Basu, Sukalyan

    2005-04-01

    The extraction behaviour of Pr(III) from aqueous nitric acid medium employing benzoylacetone has been studied in presence of two crown ethers, viz., 15-crown-5 and benzo-15-crown-5 in chloroform medium using UV-vis absorption spectroscopy. The binary equilibrium constant (logk(ex)) for the complex [Pr(benzoylacetonate)(NO3(-))2(H(2)O)] in organic phase was found to be 1.170. The overall equilibrium constants (logK) for the ternary species [Pr(benzoylacetonate)(crown ether)(NO3(-))(2)] were estimated to be 4.01 and 4.41 for 15-crown-5 and benzo-15-crown-5, respectively. The trend in the equilibrium constant values were very much in accordance with the nature of substitution of the donor moiety. The extraction of Pr(III) by the benzoylacetone-crown ether combination was maximum at pH 3.0 and extraction decreases with increase in pH. It has been found that the extent of extraction of Pr(III) in organic phase as the binary as well as ternary complex [Pr(benzoylacetonate)(NO3(-))(2)(H(2)O)] and [Pr(benzoylacetonate)(crown ether)(NO3(-))(2)] increases with increase in concentration of the ligand. Similar trend is observed in the extraction by only donors. Enthalpies and entropies of formation for the ternary extraction process have been estimated. In addition, the effect of NaNO(3) as foreign salt was also studied and it was observed that with increase in ionic strength, percentage extraction increases.

  10. A new silver nanorod SPR probe for detection of trace benzoyl peroxide

    NASA Astrophysics Data System (ADS)

    Jiang, Zhiliang; Wen, Guiqing; Luo, Yanghe; Zhang, Xinghui; Liu, Qingye; Liang, Aihui

    2014-06-01

    The stable silver nanorod (AgNR) sol in red was prepared by the two-step procedure of NaBH4-H2O2 and citrate heating reduction. The AgNR had a transverse and a longitudinal surface plasmon resonance (SPR) absorption peak at 338 nm and 480 nm. Meanwhile, two transverse and longitudinal SPR Rayleigh scattering (SPR-RS) peaks at 340 nm and 500 nm were observed firstly using common fluorescence spectrometer. The SPR absorption, RS, surface enhanced Raman scattering (SERS) and electron microscope technology were used to study the formation mechanism of red silver nanorods and the SERS enhancement mechanism of nano-aggregation. The AgNR-BPO SPR absorption and AgNR-NaCl-BPO SPR-RS analytical systems were studied to develop two new simple, rapid, and low-cost SPR methods for the detection of trace BPO.

  11. (Benzoyl­acetonato-κ2 O,O′)dicarbonyl­rhodium(I)

    PubMed Central

    Pretorius, Carla; Roodt, Andreas

    2012-01-01

    In the title compound, [Rh(C10H9O2)(CO)2], a distorted square-planar coordination geometry is observed around the RhI atom, formed by the O atoms of the bidentate ligand and two C atoms from the carbonyl ligands. The RhI atom is displaced from the plane through the surrounding atoms by 0.017 Å. In the crystal, C—H⋯O inter­action is observed between a methyl group of the bidentate ligand and a carbonyl O atom. Metallophilic inter­actions [3.308 (3) and 3.461 (3) Å] between neighbouring RhI atoms are encountered in the crystal, resulting in the formation of a metal chain along the b-axis direction. PMID:23468681

  12. 2-(4-Dimethyl­amino-2-hydroxy­benzoyl)benzoic acid methanol solvate

    PubMed Central

    Guo, Jin-Chun; Liu, Qing-Hao; Guo, Jin-Ying; Chen, Mei-Zhu; Zhang, Rui-Wang

    2008-01-01

    In the title compound, C16H15NO4·CH4O, the dihedral angle between the benzene rings is 75.21 (5)°. The structure is stabilized by an intra­molecular O—H⋯O inter­action [O⋯O = 2.589 (2) Å]. The solvent mol­ecule links symmetry-related mol­ecules of the complex via hydrogen bonds with O⋯O separations of 2.631 (2) and 2.815 (2) Å. C—H⋯O hydrogen bonds are also present. PMID:21581387

  13. Superarming Common Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection

    PubMed Central

    Premathilake, Hemali D.; Mydock, Laurel K.

    2010-01-01

    A complementary concept for superarming glycosyl donors through the use of common protecting groups was previously discovered with S-benzoxazolyl (SBox) glycosyl donors. As this strategy can be of benefit to existing oligosaccharide methodologies, it has now been expanded to encompass a wide array of common, stable glycosyl donors. The versatility of this developed technique has been further illustrated in application to a sequential chemoselective oligosaccharide synthesis, wherein a superarmed ethyl thioglycoside was incorporated into the conventional armed-disarmed strategy. PMID:20104917

  14. Rapid determination and chemical change tracking of benzoyl peroxide in wheat flour by multi-step IR macro-fingerprinting

    NASA Astrophysics Data System (ADS)

    Guo, Xiao-Xi; Hu, Wei; Liu, Yuan; Sun, Su-Qin; Gu, Dong-Chen; He, Helen; Xu, Chang-Hua; Wang, Xi-Chang

    2016-02-01

    BPO is often added to wheat flour as flour improver, but its excessive use and edibility are receiving increasing concern. A multi-step IR macro-fingerprinting was employed to identify BPO in wheat flour and unveil its changes during storage. BPO contained in wheat flour (< 3.0 mg/kg) was difficult to be identified by infrared spectra with correlation coefficients between wheat flour and wheat flour samples contained BPO all close to 0.98. By applying second derivative spectroscopy, obvious differences among wheat flour and wheat flour contained BPO before and after storage in the range of 1500-1400 cm- 1 were disclosed. The peak of 1450 cm- 1 which belonged to BPO was blue shifted to 1453 cm- 1 (1455) which belonged to benzoic acid after one week of storage, indicating that BPO changed into benzoic acid after storage. Moreover, when using two-dimensional correlation infrared spectroscopy (2DCOS-IR) to track changes of BPO in wheat flour (0.05 mg/g) within one week, intensities of auto-peaks at 1781 cm- 1 and 669 cm- 1 which belonged to BPO and benzoic acid, respectively, were changing inversely, indicating that BPO was decomposed into benzoic acid. Moreover, another autopeak at 1767 cm- 1 which does not belong to benzoic acid was also rising simultaneously. By heating perturbation treatment of BPO in wheat flour based on 2DCOS-IR and spectral subtraction analysis, it was found that BPO in wheat flour not only decomposed into benzoic acid and benzoate, but also produced other deleterious substances, e.g., benzene. This study offers a promising method with minimum pretreatment and time-saving to identify BPO in wheat flour and its chemical products during storage in a holistic manner.

  15. Impact of a benzoyl urea insecticide on aquatic macroinvertebrates in ditch mesocosms with and without non-sprayed sections.

    PubMed

    Brock, Theo C M; Roessink, Ivo; Belgers, J Dick M; Bransen, Fred; Maund, Steve J

    2009-10-01

    The long-term response, including recovery, of aquatic macroinvertebrates to short-term insecticide exposure may be affected by the presence of uncontaminated refuges in the stressed ecosystem. Experimental ditches were used to study the influence of non-sprayed ditch sections regarding the ecotoxicological effects on and the recovery of macroinvertebrates following treatment with the insecticide lufenuron. The treatment regimes differed in the proportion of the ditch (0, 33, 67, and 100% of surface area) that was sprayed to reach a lufenuron concentration of 3 microg/L in the water column of the sprayed ditch section. The magnitude and duration of effects on macroinvertebrates, and on arthropods in particular, were higher when a larger proportion of the ditch was treated. Initially, more pronounced responses were observed for bivoltine and multivoltine insects and macrocrustaceans than for univoltine and semivoltine arthropods. Most macroinvertebrate arthropods showed delayed responses, with maximum treatment-related effects observed two to six weeks after lufenuron application. This latency of effects can be explained by the mode of action of lufenuron, involving inhibition of chitin synthesis, which affects arthropod molting and metamorphosis. The observed effects were short-lived only in those ditches where 33% of the surface area was sprayed. In the ditches where 67 and 100% of the surface area was sprayed, some insects and macrocrustaceans showed long-term effects. In the 100% sprayed ditches in particular, the treatment-related reduction in arthropods resulted in indirect effects, such as an increase in snails, and later in an increase in the ephemeropteran Cloeon dipterum, probably because of an increase in periphyton, and release from competition and predation. Effects that are most likely indirect also were observed for Oligochaeta, Hirudinea, and the flatworm Mesostoma sp. PMID:19453208

  16. Rapid determination and chemical change tracking of benzoyl peroxide in wheat flour by multi-step IR macro-fingerprinting.

    PubMed

    Guo, Xiao-Xi; Hu, Wei; Liu, Yuan; Sun, Su-Qin; Gu, Dong-Chen; He, Helen; Xu, Chang-Hua; Wang, Xi-Chang

    2016-02-01

    BPO is often added to wheat flour as flour improver, but its excessive use and edibility are receiving increasing concern. A multi-step IR macro-fingerprinting was employed to identify BPO in wheat flour and unveil its changes during storage. BPO contained in wheat flour (<3.0 mg/kg) was difficult to be identified by infrared spectra with correlation coefficients between wheat flour and wheat flour samples contained BPO all close to 0.98. By applying second derivative spectroscopy, obvious differences among wheat flour and wheat flour contained BPO before and after storage in the range of 1500-1400 cm(-1) were disclosed. The peak of 1450 cm(-1) which belonged to BPO was blue shifted to 1453 cm(-1) (1455) which belonged to benzoic acid after one week of storage, indicating that BPO changed into benzoic acid after storage. Moreover, when using two-dimensional correlation infrared spectroscopy (2DCOS-IR) to track changes of BPO in wheat flour (0.05 mg/g) within one week, intensities of auto-peaks at 1781 cm(-1) and 669 cm(-1) which belonged to BPO and benzoic acid, respectively, were changing inversely, indicating that BPO was decomposed into benzoic acid. Moreover, another autopeak at 1767 cm(-1) which does not belong to benzoic acid was also rising simultaneously. By heating perturbation treatment of BPO in wheat flour based on 2DCOS-IR and spectral subtraction analysis, it was found that BPO in wheat flour not only decomposed into benzoic acid and benzoate, but also produced other deleterious substances, e.g., benzene. This study offers a promising method with minimum pretreatment and time-saving to identify BPO in wheat flour and its chemical products during storage in a holistic manner.

  17. 75 FR 9767 - Classification of Benzoyl Peroxide as Safe and Effective and Revision of Labeling to Drug Facts...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-03-04

    ..., resorcinol monoacetate, salicylic acid and/or sulfur to meet OTC drug labeling content and format... resorcinol, resorcinol monoacetate, salicylic acid, and/or sulfur subject to 21 CFR part 333 is March 4, 2015..., resorcinol, resorcinol monoacetate, salicylic acid, and/or sulfur be relabeled. We revised the warnings...

  18. Crystal structure of bis-(aceto-phenone 4-benzoyl-thio-semicarbazonato-κ(2) N (1),S)nickel(II).

    PubMed

    Kadir, Faraidoon Karim; Shamsuddin, Mustaffa; Rosli, Mohd Mustaqim

    2016-05-01

    In the asymmetric unit of the title complex, [Ni(C16H14N3OS)2], the nickel ion is tetra-coordinated in a distorted square-planar geometry by two independent mol-ecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C=N bonds. The close approach of hydrogen atoms to the Ni(2+) atom suggests anagostic inter-actions (Ni⋯H-C) are present. The crystal structure is built up by a network of two C-H⋯O inter-actions. One of the inter-actions forms inversion dimers and the other links the mol-ecules into infinite chains parallel to [100]. In addition, a weak C-H⋯π inter-action is also present. PMID:27308036

  19. Impact of a benzoyl urea insecticide on aquatic macroinvertebrates in ditch mesocosms with and without non-sprayed sections.

    PubMed

    Brock, Theo C M; Roessink, Ivo; Belgers, J Dick M; Bransen, Fred; Maund, Steve J

    2009-10-01

    The long-term response, including recovery, of aquatic macroinvertebrates to short-term insecticide exposure may be affected by the presence of uncontaminated refuges in the stressed ecosystem. Experimental ditches were used to study the influence of non-sprayed ditch sections regarding the ecotoxicological effects on and the recovery of macroinvertebrates following treatment with the insecticide lufenuron. The treatment regimes differed in the proportion of the ditch (0, 33, 67, and 100% of surface area) that was sprayed to reach a lufenuron concentration of 3 microg/L in the water column of the sprayed ditch section. The magnitude and duration of effects on macroinvertebrates, and on arthropods in particular, were higher when a larger proportion of the ditch was treated. Initially, more pronounced responses were observed for bivoltine and multivoltine insects and macrocrustaceans than for univoltine and semivoltine arthropods. Most macroinvertebrate arthropods showed delayed responses, with maximum treatment-related effects observed two to six weeks after lufenuron application. This latency of effects can be explained by the mode of action of lufenuron, involving inhibition of chitin synthesis, which affects arthropod molting and metamorphosis. The observed effects were short-lived only in those ditches where 33% of the surface area was sprayed. In the ditches where 67 and 100% of the surface area was sprayed, some insects and macrocrustaceans showed long-term effects. In the 100% sprayed ditches in particular, the treatment-related reduction in arthropods resulted in indirect effects, such as an increase in snails, and later in an increase in the ephemeropteran Cloeon dipterum, probably because of an increase in periphyton, and release from competition and predation. Effects that are most likely indirect also were observed for Oligochaeta, Hirudinea, and the flatworm Mesostoma sp.

  20. 21 CFR 133.181 - Provolone cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... the cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is... weight of the benzoyl peroxide used. If milk is bleached in this manner, vitamin A is added to the...

  1. 21 CFR 133.181 - Provolone cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... the cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate used to bleach the dairy ingredients. The weight of the benzoyl peroxide is... weight of the benzoyl peroxide used. If milk is bleached in this manner, vitamin A is added to the...

  2. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added...

  3. Superarming the S-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection

    PubMed Central

    Mydock, Laurel K.; Demchenko, Alexei V.

    2011-01-01

    The strategic placement of common protecting groups led to the discovery of a new method for “superarming” glycosyl donors. Conceptualized from our previous studies on the O-2/O-5 Cooperative Effect, it was determined that S-benzoxazolyl glycosyl donors possessing both a participating moiety at C-2 and an electronically armed lone pair at O-5, such as the superarmed glycosyl donor shown above, were exceptionally reactive. PMID:18447363

  4. Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide.

    PubMed

    Idemudia, Omoruyi G; Sadimenko, Alexander P; Afolayan, Anthony J; Hosten, Eric C

    2015-01-01

    Two Schiff base ligands Ampp-Sn 1 and Bmpp-Sn 2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds against Staphylococcus aureus, Bacillus pumilus, Proteus vulgaris, and Aeromonas hydrophila for antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity. PMID:26106285

  5. 3′-Benzoyl-1′-methyl-4′-phenyl­spiro[acenaphthyl­ene-1(2H),2′-pyrrolidin]-2-one

    PubMed Central

    Augustine, T.; Vithiya, Scholastica Mary; Ignacimuthu, S.; Ramkumar, V.

    2010-01-01

    In the title compound, C29H23NO2, the pyrrolidine ring adopts a twisted conformation about one of the C—N bonds. The acenaphthone ring (r.m.s. deviation = 0.025 Å) lies almost perpendicular to the pyrrolidine ring [dihedral angle = 88.08 (8)°]. The dihedral angle between the phenyl rings is 88.12 (11)°. In the crystal structure, weak C—H⋯π inter­actions connect the mol­ecules. PMID:21589163

  6. Structure of enzyme-bound substrates: resonance Raman and kinetic evidence for differential enzyme-substrate contacts in N-(Pentafluoro-benzoyl)glycine dithioacyl and thioacyl papain

    NASA Astrophysics Data System (ADS)

    Lee, H.; Angus, R. H.; Storer, A. C.; Carey, P. R.

    1989-12-01

    Resonance Raman (RR) spectroscopy is used to probe the structure of the substrate in the substrate-enzyme complex N-pentafluorobenzoyl) glycine (dithioacyl) papain (C 6F 5C(=O) NHCH 2C(=S)S-papain). This system was chosen since the high electron withdrawing capacity of the C 6F 5 group markedly affects electron density of the -NH- moiety which, in turn, is known to change catalytic activity. The RR spectrum of the enzyme-substrate complex is interpreted by reference to the model compound N-(pentafluorobenzoyl) glycine ethyl dithioester (C 6F 5(CO))NHCH 2C(=S)SC 2H 5. The RR spectra of this compound in aqueous or organic solvents can be understood in terms of the known conformational states of N-acylglycine dithioesters. Comparison of model with enzyme-substrate RR spectra shows that the substrate is binding in the active site in a conformer known as conformer B characterized by a small-NHCH 2CS(thiol) torsional angle and close N-to-S (thiol) contact. Kinetic rate-structure correlations are developed involving k3, the rate constant for deacylation, and the strength of the N-to-S (thiol) interaction. N-(Pentafluorobenzoyl) glycine dithioacyl papain fits the rate-structure correlation whereas the corresponding pentafluorobenzoyl glycine thiol intermediate does not. It is proposed that the difference in the size of the CS compared to the CO group brings about a small change in the dithioacyl papain compared to the thiolacyl papain conformation such that enzyme-substrate contacts involving ortho and meta F atoms in the thiol acyl enzyme case are weakened or removed in the case of the dithioacyl papain.

  7. Structure and spectroscopic properties of ruthenium(II) bipyridyl N-benzoyl-N'-(1,10-phenanthrolin-5-Yl)-thiourea

    SciTech Connect

    Tan, Siew San; Kassim, Mohammad B.

    2015-09-25

    Ruthenium bipyridyl incorporating phenanthroline with thiourea molecules, [Ru(bpy){sub 2}(Phen-BT)](PF{sub 6}){sub 2}], has been synthesized and characterized by spectroscopic and electrochemical techniques. The infrared spectra of the complex shows the characteristics stretching frequencies for N-H at 3646 and 3585 cm{sup −1}, ν(C-N){sub phen} 1426 cm{sup −1}, ν(C=O) 1675 cm{sup −1}, ν(C=S) 1246 cm{sup −1}, ν(C-H){sub aromatic} 3353-3086 cm{sup −1}, ν(C-N){sub aliphatic} 1169-1026 cm{sup −1}, ν(C-H){sub bend} 764 cm{sup −1} and ν(PF{sub 6}{sup −}){sub free} 842 cm{sup −1}. The complex reveals two π→π* absorption bands at 237 (ε=26,302) and 286 nm (ε=36,848), which were assigned to the phenanthroline and bipyridyl moieties, respectively. A slightly broad and low energy band in the UV-vis spectrum at 450 nm (ε=7,209) of the complex was assigned to a MLCT transition. Besides, the complex also exhibits an emission band at 615 nm that arises from an excitation with a 440 nm light energy. The cyclic voltammetry of the complex shows an oxidation potential at +1.305 V vs. SCE that corresponds to the formal oxidation of Ru(II) to Ru(III)

  8. Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide.

    PubMed

    Idemudia, Omoruyi G; Sadimenko, Alexander P; Afolayan, Anthony J; Hosten, Eric C

    2015-01-01

    Two Schiff base ligands Ampp-Sn 1 and Bmpp-Sn 2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds against Staphylococcus aureus, Bacillus pumilus, Proteus vulgaris, and Aeromonas hydrophila for antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity.

  9. Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.

    PubMed

    Rivero-Buceta, Eva; Carrero, Paula; Doyagüez, Elisa G; Madrona, Andrés; Quesada, Ernesto; Camarasa, María José; Peréz-Pérez, María Jesús; Leyssen, Pieter; Paeshuyse, Jan; Balzarini, Jan; Neyts, Johan; San-Félix, Ana

    2015-03-01

    Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used.

  10. Ethyl 1-benzoyl-4-hy­droxy-2,6-diphenyl-1,2,5,6-tetra­hydro­pyridine-3-carboxyl­ate

    PubMed Central

    Aridoss, G.; Sundaramoorthy, S.; Velmurugan, D.; Jeong, Y. T.

    2011-01-01

    In the title compound, C27H25NO4, the tetra­hydro­pyridine ring adopts a half-chair conformation. The three phenyl rings form dihedral angles of 66.33 (7), 87.36 (8) and 36.90 (7)° with the least-squares plane through the tetra­hydro­pyridine ring. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, generating an S(6) motif. PMID:21522308

  11. Synthesis and X-ray crystal structure determination of N-p-methylphenyl-4-benzoyl-3,4-diphenyl-2-azetidinone

    SciTech Connect

    Kabak, Mehmet; Senoez, Huelya; Elmali, Ayhan; Adar, Vildan; Svoboda, Ingrid; Dusek, Michal; Fejfarova, Karla

    2010-12-15

    The title compound, C{sub 29}H{sub 23}NO{sub 2}, has been characterized by single-crystal X-ray diffraction at two different temperatures (303 K and 120 K) and wavelengths (MoK{sub {alpha}} and CuK{sub {alpha}}). The non-centrosymmetric hexagonal crystal structure contains four-membered planar {beta}-lactam ring with an unusually long C-C bond. The {beta}-lactam ring is almost planar.

  12. Linear and branched alkyl-esters and amides of gallic acid and other (mono-, di- and tri-) hydroxy benzoyl derivatives as promising anti-HCV inhibitors.

    PubMed

    Rivero-Buceta, Eva; Carrero, Paula; Doyagüez, Elisa G; Madrona, Andrés; Quesada, Ernesto; Camarasa, María José; Peréz-Pérez, María Jesús; Leyssen, Pieter; Paeshuyse, Jan; Balzarini, Jan; Neyts, Johan; San-Félix, Ana

    2015-03-01

    Linear and branched compounds that contain two, three or five units of galloyl (3,4,5-trihydroxybenzoyl) or its isomer 2,3,4-trihydroxybenzoyl, as well as other mono- or dihydroxybenzoyl moieties have been synthesized. These molecules have been evaluated for their in vitro inhibitory effects against a wide panel of viruses showing preferential activity against HIV and HCV. Our structure-activity relationship studies demonstrated that the 2,3,4-trihydroxybenzoyl moiety provides better antiviral activities than the galloyl (3,4,5-trihydroxybenzoyl) moiety that is present in natural green tea catechins. This observation can be of interest for the further rational exploration of compounds with anti-HCV/HIV properties. The most notable finding with respect to HIV is that the tripodal compounds 43 and 45, with three 2,3,4-trihydroxybenzoyl moieties, showed higher activities than linear compounds with only one or two. With respect to HCV, the linear compounds, 52 and 41, containing a 12 polymethylene chain and two 2,3 di- or 2,3,4 tri-hydroxybenzoyl groups respectively at the ends of the molecule showed good antiviral efficiency. Furthermore, the anti-HCV activity of both compounds was observed at concentrations well below the cytotoxicity threshold. A representative member of these compounds, 41, showed that the anti-HCV activity was largely independent of the genetic make-up of the HCV subgenomic replicon and cell lines used. PMID:25617695

  13. Synthesis and Characterization of Bioactive Acylpyrazolone Sulfanilamides and Their Transition Metal Complexes: Single Crystal Structure of 4-Benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one Sulfanilamide

    PubMed Central

    Idemudia, Omoruyi G.; Sadimenko, Alexander P.; Afolayan, Anthony J.; Hosten, Eric C.

    2015-01-01

    Two Schiff base ligands Ampp-Sn 1 and Bmpp-Sn 2, afforded by a condensation reaction between sulfanilamide and the respective acylpyrazolone carbonyl precursors, their Mn(II), Co(II), Ni(II), and Cu(II) complexes prepared by the reaction of ligands and corresponding metal salts in aqueous solutions, were synthesized and then characterized by both analytical and spectroscopic methods, in a view to developing new improved bioactive materials with novel properties. On the basis of elemental analysis, spectroscopic and TGA results, transition metal complexes, with octahedral geometry having two molecules of the bidentate keto-imine ligand each, have been proposed. The single crystal structure of Bmpp-Sn according to X-ray crystallography showed a keto-imine tautomer type of Schiff base, having three intramolecular bonds, one short N2⋯H2⋯O3 hydrogen bond of 1.90 Å and two long C13⋯H13⋯O2 and C32⋯H32⋯O3 hydrogen bonds of 2.48 Å. A moderate to low biological activities have been exhibited by synthesized compounds when compared with standard antimicrobial agents on screening the synthesized compounds against Staphylococcus aureus, Bacillus pumilus, Proteus vulgaris, and Aeromonas hydrophila for antibacterial activity and against free radical 1, 1-diphenyl-2-picryl-hydrazyl (DPPH) for antioxidant activity. PMID:26106285

  14. Crystal structure of bis­(aceto­phenone 4-benzoyl­thio­semicarbazonato-κ2 N 1,S)nickel(II)

    PubMed Central

    Kadir, Faraidoon Karim; Shamsuddin, Mustaffa; Rosli, Mohd Mustaqim

    2016-01-01

    In the asymmetric unit of the title complex, [Ni(C16H14N3OS)2], the nickel ion is tetra­coordinated in a distorted square-planar geometry by two independent mol­ecules of the ligand which act as mononegative bidentate N,S-donors and form two five-membered chelate rings. The ligands are in trans (E) conformations with respect to the C=N bonds. The close approach of hydrogen atoms to the Ni2+ atom suggests anagostic inter­actions (Ni⋯H—C) are present. The crystal structure is built up by a network of two C—H⋯O inter­actions. One of the inter­actions forms inversion dimers and the other links the mol­ecules into infinite chains parallel to [100]. In addition, a weak C—H⋯π inter­action is also present. PMID:27308036

  15. Teens and Acne Treatment

    MedlinePlus

    ... Types of treatments Benzoyl peroxide Benzoyl peroxide wash, lotion, or gel—the most effective acne treatment you ... and make it redder than the wash or lotion, so try the wash or lotion first. How ...

  16. 21 CFR 133.111 - Caciocavallo siciliano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... concentrated or dried products used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the...

  17. 21 CFR 133.183 - Romano cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk... combined, is not more than six times the weight of the benzoyl peroxide used. If milk is bleached in...

  18. 21 CFR 133.183 - Romano cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk... combined, is not more than six times the weight of the benzoyl peroxide used. If milk is bleached in...

  19. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... nonfat dry milk used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the weight of...

  20. 21 CFR 133.111 - Caciocavallo siciliano cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... concentrated or dried products used. (2) Such milk may be bleached by the use of benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl peroxide is not more than 0.002 percent of the weight of the milk bleached, and the...

  1. Synthesis, Spectroscopic Characterization, and In Vitro Antimicrobial Studies of Pyridine-2-Carboxylic Acid N′-(4-Chloro-Benzoyl)-Hydrazide and Its Co(II), Ni(II), and Cu(II) Complexes

    PubMed Central

    Singh, Jagvir; Singh, Prashant

    2012-01-01

    N-substituted pyridine hydrazide (pyridine-2-carbonyl chloride and 4-chloro-benzoic acid hydrazide) undergoes hydrazide formation of the iminic carbon nitrogen double bond through its reaction with cobalt(II), nickel(II), and copper(II) metal salts in ethanol which are reported and characterized based on elemental analyses, IR, solid reflectance, magnetic moment, molar conductance, and thermal analysis (TG). From the elemental analyses data, 1 : 2 metal complexes are formed having the general formulae [MCl2(HL)2] ·yH2O (where M = Co(II), Ni(II), and Cu(II), y = 1–3). The important infrared (IR) spectral bands corresponding to the active groups in the ligand and the solid complexes under investigation were studied. IR spectra show that ligand is coordinated to the metal ions in a neutral bidentate manner with ON donor sites. The solid complexes have been synthesized and studied by thermogravimetric analysis. All the metal chelates are found to be nonelectrolytes. From the magnetic and solid reflectance spectra, the complexes (cobalt(II), nickel(II), and copper(II)) have octahedral and square planner geometry, respectively. The antibacterial and antifungal activity's data show that the metal complexes have a promising biological activity comparable with the parent ligand against bacterial and fungal species. PMID:23125560

  2. [(1R)-3-Benzoyl-1,7,7-trimethyl­bicyclo­[2.2.1]heptan-2-onato-κ2 O,O′]chlorido(η6-p-cymene)ruthenium(II)

    PubMed Central

    Harrad, Mohamed Anouar; Valerga, Pedro; Puerta, M. Carmen; Ali, Mustapha Ait; El Firdoussi, Larbi; Karim, Abdellah

    2010-01-01

    The asymmetric unit of the title compound, [RuCl(C10H14)(C17H19O2)], contains two diastereomers. In both, the RuII ion has a tetra­hedral coordination, formed by two O atoms of the camphor-derived ligand and the p-cymene and Cl ligands. In the crystal structure, weak inter­molecular C—H⋯Cl inter­actions link the mol­ecules into columns propagated along [010]. PMID:21580227

  3. N1-Benzoyl-N2-[1-(1-naphthyl)ethyl]-trans-1,2-diaminocyclohexanes: Development of 4-chlorophenylcarboxamide (calhex 231) as a new calcium sensing receptor ligand demonstrating potent calcilytic activity.

    PubMed

    Kessler, Albane; Faure, Hélène; Petrel, Christophe; Rognan, Didier; Césario, Michèle; Ruat, Martial; Dauban, Philippe; Dodd, Robert H

    2006-08-24

    A structure-activity relationship (SAR) study was performed principally at the N1 position of N1-arylsulfonyl-N2-[1-(1-naphthyl)ethyl]-trans-1,2-diaminocyclohexanes, a new family of calcilytics acting at the calcium sensing receptor (CaSR). The most active compound in this series was the 4-(trifluoromethoxy)benzenesulfonyl derivative 7e, which displayed an IC50 of 5.4 +/- 0.5 microM with respect to the inhibition of calcium-induced tritiated inositol phosphate ([3H]IP) accumulation in Chinese hamster ovarian (CHO) cells expressing the CaSR. Replacement of the sulfonamide linkage of this compound by a carboxamide led to a 6-fold increase in activity (7m, IC50 = 0.9 +/- 0.2 microM). Among the carboxamides synthesized, one of the most active compounds was the 4-chlorophenylcarboxamide (1S,2S,1'R)-7n (Calhex 231, IC50 = 0.33 +/- 0.02 microM). The absolute configuration of (1S,2S,1'R)-7n was deduced from an X-ray crystallographic study of one of the diastereomers of compound 7d. The stereochemical preference for the (1S,2S,1'R)-isomers can be rationalized on the basis of a three-dimensional model of the calcilytic binding pocket of the CaSR. Removal of the C-1' methyl group or replacement of the 1-naphthyl group by a 2-naphthyl or biphenyl moiety led to appreciable loss of calcilytic activity. Compounds 7e, 7m, and Calhex 231 did not stimulate [3H]IP accumulation in CHO cells expressing or not expressing the CaSR. PMID:16913701

  4. Synthesis of novel binary and ternary complexes derived from 1-(2-hydroxy benzoyl)-4-phenylthiosemicarbazide (L1) and 2,2‧-dipyridyl (L2) with CoII, CuII and ZnII salts

    NASA Astrophysics Data System (ADS)

    Azhari, Shaker J.; Mlahi, Mosaad R.; Al-Asmy, Ahmed A.; Mostafa, Mohsen M.

    2015-02-01

    The complexes derived the reactions of 1-(2-hydroxybenzoyl)-4-phenylthiosemicarbazide (L1) with MX2 (M = CoII, CuII and ZnII ions; X = Cl- in case of CoII and CuII ions, Cl- and Ac- in case of ZnII) in EtOH, were synthesized and characterized. The results suggested that the complexes have the general formulae, [Cu(L1-2H)(EtOH)(H2O)2]ṡH2O, [Co(L1-2H)(EtOH)(H2O)]ṡ2H2O and [Zn(L1-2H)(EtOH)]. Also, the ternary complexes, derived from the reactions 2,2‧-dipyridyl (L2) with the metals salts followed by adding a solution of the L1 were synthesized and having the general formulae, [Cu2(L2)(L1-2H)(H2O)(OH)2]ṡ1/2H2O, [Co(L2)(L1-2H)]ṡ1.5EtOHṡ3H2O and [Zn(L2)(L1-2H)]ṡEtOH. The binary and ternary complexes were characterized by elemental analyses, molar conductivities, spectral (IR, UV-Vis, 1H-NMR and mass), thermal and magnetic measurements. The existence of OH group in the ternary complexes was confirmed by IR spectra. The amounts of solvent were determined from the results of TGA. The biological activity for the ligand and two complexes were tested against DNA.

  5. Two metabolites from Aspergillus flavipes.

    PubMed

    Clark, A M; Hufford, C D; Robertson, L W

    1977-01-01

    Two novel fungal metabolites, N-benzoyl-L-phenylalaninol (1a) and asperphenamate (2) were isolated from the culture filtrate and mycelium of Aspergillus flavipes ATCC 11013. N-benzoyl-L-phenylalaninol was identified by direct comparison with an authentic sample. The structure of asperphenamate is proposed as (S)-N-benzoyl-phenylalanine-(S)-2-benzamido-3-phenyl propyl ester, based on chemical and spectroscopic evidence. PMID:875642

  6. Peptide backbone cleavage by α-amidation is enhanced at methionine residues.

    PubMed

    Hellwig, Michael; Löbmann, Katja; Orywol, Tom

    2015-01-01

    Cleavage reactions at backbone loci are one of the consequences of oxidation of proteins and peptides. During α-amidation, the Cα -N bond in the backbone is cleaved under formation of an N-terminal peptide amide and a C-terminal keto acyl peptide. On the basis of earlier works, a facilitation of α-amidation by the thioether group of adjacent methionine side chains was proposed. This reaction was characterized by using benzoyl methionine and benzoyl alanyl methionine as peptide models. The decomposition of benzoylated amino acids (benzoyl-methionine, benzoyl-alanine, and benzoyl-methionine sulfoxide) to benzamide in the presence of different carbohydrate compounds (reducing sugars, Amadori products, and reductones) was studied during incubation for up to 48 h at 80 °C in acetate-buffered solution (pH 6.0). Small amounts of benzamide (0.3-1.5 mol%) were formed in the presence of all sugars and from all benzoylated species. However, benzamide formation was strongly enhanced, when benzoyl methionine was incubated in the presence of reductones and Amadori compounds (3.5-4.2 mol%). The reaction was found to be intramolecular, because α-amidation of a similar 4-methylbenzoylated amino acid was not enhanced in the presence of benzoyl-methionine and carbohydrate compounds. In the peptide benzoyl-alanyl-methionine, α-amidation at the methionine residue is preferred over α-amidation at the benzoyl peptide bond. We propose here a mechanism for the enhancement of α-amidation at methionine residues.

  7. 21 CFR 133.181 - Provolone cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... color of the curd. (ii) Calcium chloride in an amount not more than 0.02 percent (calculated as anhydrous calcium chloride) by weight of the dairy ingredients, used as a coagulation aid. (iii) Enzymes of... the cheese. (v) Benzoyl peroxide or a mixture of benzoyl peroxide with potassium alum, calcium...

  8. Acne - self-care

    MedlinePlus

    ... It may help to use a wash with salicylic acid or benzoyl if your skin is oily and prone to acne. Remove all ... products may contain benzoyl peroxide, sulfur, resorcinol, or ... bacteria, drying up skin oils, or causing the top layer of your ...

  9. Cordyceamides A and B from the Culture Liquid of Cordyceps sinensis (BERK.) SACC.

    PubMed

    Jia, Jing-Ming; Tao, Hai-Hua; Feng, Bao-Min

    2009-01-01

    Two new aurantiamides named as cordyceamides A and B were isolated from the culture liquid of Cordyceps sinensis (BERK.) SACC., along with one known compound, aurantiamide acetate. Their structures were elucidated as N-benzoyl-L-tyrosinyl-L-phenylalaninol acetate and N-benzoyl-L-tyrosinyl-L-p-hydroxyphenylalaninol acetate by 1D, 2D-NMR techniques and comparison with literatures. PMID:19122327

  10. Acne

    MedlinePlus

    ... can try different ones to see which helps. Products with benzoyl peroxide (say: BEN-zoil peh - ROK - side) or salicylic (say: sal-uh-SIL - ick) acid in them are usually pretty helpful for treating acne. Benzoyl peroxide kills the bacteria that can lead to acne and it also ...

  11. New phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Koike, Kazuo; Li, Wei; Liu, Lijuan; Hata, Emiko; Nikaido, Tamotsu

    2005-02-01

    Five new phenolic glycosides, cucurbitosides A-E (1-5), were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as 2-(4-hydroxy)phenylethanol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1), 2-(4-hydroxyphenyl)ethanol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2), 4-hydroxybenzyl alcohol 4-O-(5-O-benzoyl)-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (3), 4-hydroxybenzyl alcohol 4-O-[5-O-(4-hydroxy)benzoyl]-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (4) and 4-hydroxyphenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (5) on the basis of spectroscopic analysis and chemical evidence.

  12. Quinoxaline chemistry. Part 16. 4-substituted anilino and 4-substituted phenoxymethyl pyrrolo[1,2-a]quinoxalines and N-[4-(pyrrolo[1,2-a]quinoxalin-4-yl)amino and hydroxymethyl]benzoyl glutamates. Synthesis and evaluation of in vitro biological activity.

    PubMed

    Alleca, Sergio; Corona, Paola; Loriga, Mario; Paglietti, Giuseppe; Loddo, Roberta; Mascia, Valeria; Busonera, Bernardetta; La Colla, Paolo

    2003-09-01

    Twenty eight pyrrolo[1,2-a]quinoxalines bearing at position 4 various substituents related to the moieties present in classical and non classical antifolic agents were prepared and evaluated in vitro for antiproliferative activity. In an in vitro screening performed at NCI, several compounds emerged as potent antiproliferative agents at concentrations ranging between 10 and 100 microM. Interestingly, some of these compounds proved active also against bovine and murine DHFR (Farmaco 53 (1998) 480). More recently, a compound of classical antifolate type has been reported to be a potent inhibitor of hDHFR in vitro (Farmaco 58 (2003) 51). We then synthesized new derivatives that, in our hands, were endowed with in vitro antiproliferative activities as low as 3.4 microM against a panel of cell lines derived from hematological and solid tumours. In addition, a complete screening of cytotoxicity, antiretroviral HIV-1 and antimicrobial activity has been carried out.

  13. 3-{[1-(2,3,5-Tri-O-benzoyl-β-d-ribofur­an­os-1-yl)-1H-1,2,3-triazol-4-yl]meth­yl}quin­a­zolin-4(3H)-one

    PubMed Central

    Ouahrouch, Abdelaaziz; Taourirte, Moha; El Azhari, Mohamed; Saadi, Mohamed; El Ammari, Lahcen

    2012-01-01

    In the compound, C37H29N5O8, the quinazoline residue forms a dihedral angle of 72.90 (9)° with the triazole ring. The furan ring adopts a twist conformation. In the crystal, the mol­ecules are linked by non-classical C—H⋯N and C—H⋯O hydrogen bonds, building an infinite three-dimensional network. PMID:23284480

  14. A separation of protactinium from neutron-irradiated thorium.

    PubMed

    Lyle, S J; Shendrikar, A D

    1966-01-01

    A convenient-method, based on liquid-liquid extraction with N-benzoyl-N-phenylhydroxylamine in chloroform, is given for the separation of protactinium-233 from neutron-irradiated thorium. PMID:18959855

  15. Why Do I Get Acne?

    MedlinePlus

    ... you've been exercising. Many over-the-counter lotions and creams containing salicylic acid or benzoyl peroxide ... Sometimes even though they wash properly and try lotions and oil-free makeup, people get acne anyway — ...

  16. Acne

    MedlinePlus

    ... suggest you also try an over-the-counter lotion or cream. These medicines may make your skin ... work, your doctor may prescribe a cream or lotion with benzoyl peroxide, resorcinol, salicylic acid, or sulfur. ...

  17. Sensitive radiometric assay for enkephalin convertase and other carboxypeptidase B-like enzymes

    SciTech Connect

    Stack, G.; Fricker, L.D.; Snyder, S.H.

    1984-01-09

    A sensitive radiometric assay for carboxypeptidase B-like enzymes has been developed using enkephalin convertase, an enkephalin synthesizing carboxypeptidase. The assay is based on the differential solubility of /sup 3/H-labeled substrate and product in chloroform. The substrates /sup 3/H-benzoyl-Phe-Ala-Arg or /sup 3/H-benzoyl-Phe-Leu-Arg are poorly soluble in chloroform due to the charged arginine. The products of carboxypeptidase B-like activity on these substrates, /sup 3/H-benzoyl-Phe-Ala or /sup 3/H-benzoyl Phe-Leu partition quantitatively into chloroform, allowing rapid separation of product from substrate. This assay is approximately 100 times more sensitive than a similar fluorometric assay utilizing dansyl-Phe-Ala-Arg as a substrate.

  18. 21 CFR 137.105 - Flour.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...) Chlorine. (3) Nitrosyl chloride. (4) Chlorine dioxide. (5) One part by weight of benzoyl peroxide mixed... phosphate, starch, calcium carbonate. (6) Acetone peroxides complying with the provisions of § 172.802...

  19. Chem Ed Compacts.

    ERIC Educational Resources Information Center

    Wolf, Walter A., Ed.

    1979-01-01

    Tips are presented for chemistry teachers on the use of acid-base half-reactions in review lessons, the use of calculators by chemistry students, significant figures, and the preparation of benzoyl peroxide from acne medicine. (BB)

  20. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used...

  1. 21 CFR 184.1400 - Lecithin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... solvent-extracted soy, safflower, or corn oils. Lecithin is bleached, if desired, by hydrogen peroxide and benzoyl peroxide and dried by heating. (b) The ingredient meets the specifications of the Food...

  2. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... separated fatty acid fraction of the resultant product has an acetyl value of 30 to 38: (1) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid,...

  3. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or intended for use, in accordance with...

  4. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ...) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or intended for use, in accordance with...

  5. 21 CFR 172.814 - Hydroxylated lecithin.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ...) With hydrogen peroxide, benzoyl peroxide, lactic acid, and sodium hydroxide. (2) With hydrogen peroxide, acetic acid, and sodium hydroxide. (b) It is used or intended for use, in accordance with...

  6. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  7. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  8. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  9. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  10. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  11. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... weight of the benzoyl peroxide used. If milk is bleached in this manner, sufficient vitamin A is added to the curd to compensate for the vitamin A or its precursors destroyed in the bleaching process,...

  12. Synthesis of 1-[3-deoxy-β-D-psicofuranosyl]uracil and related compounds

    PubMed Central

    Holý, A.

    1974-01-01

    D-Fructose affords on treatment with cyanamide 2-amino-β-D-fructofuro[2′,3′:3,4]-oxazoline which is not isolated but transformed directly by the reaction with ethyl propiolate into O2,3-anhydro-2-[β-D-fructofuranosyl]uracil. This compound is benzoylated to the 1′,4′,6′-tri-O-benzoyl derivative by the action of benzoyl cyanide and triethylamine. On treatment with hydrogen chloride/dimethylformamide, the latter intermediate is converted to the 1-[1,4,6-tri-O-benzoyl-3-chloro-3-deoxy-β-D-psicofuranosyl]uracil 1′,4′,5′-tribenzoate from which the title nucleoside derivative is obtained by methanolysis. PMID:4370426

  13. 76 FR 36307 - Guidance for Industry on Topical Acne Drug Products for Over-the-Counter Human Use-Revision of...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-06-22

    ..., including benzoyl peroxide, resorcinol, resorcinol monoacetate, salicylic acid, and/or sulfur) (21 CFR part... applicable to all OTC topical acne products marketed under the monograph (75 FR 9767, March 4, 2010)...

  14. Topical Acne Treatments and Pregnancy

    MedlinePlus

    ... are benzoyl peroxide, azelaic acid, glycolic acid, and salicylic acid. Can I use tretinoin (Retin A®) for severe ... harmful effects on the baby. I read that salicylic acid can cause birth defects in babies. Why is ...

  15. Acne Excoriée

    MedlinePlus

    ... Exfoliants (or peeling agents) such as salicylic acid, sulfur, resorcinol, alpha-hydroxy acids (glycolic, lactic, pyruvic, and ... include: Antibiotics such as benzoyl peroxide, clindamycin, erythromycin, sulfur, sodium sulfacetamide, and azelaic acid. Retinoids – vitamin A- ...

  16. New iridoids from the fruits of Crescentia cujete.

    PubMed

    Wang, Gang; Yin, Wei; Zhou, Zhong-Yu; Hsieh, Kun-Lung; Liu, Ji-Kai

    2010-09-01

    Four new 11-nor-iridoids, 6-O-p-hydroxybenzoyl-10-deoxyeucommiol (1), 6-O-benzoyl-10-deoxyeucommiol (2), 6-O-benzoyl-dihydrocatalpolgenin (a mixture of 3 and 4), as well as two known iridoids, ningpogenin (5) and 6-O-p-hydroxybenzoylaucubin (6), were isolated from the fruits of Crescentia cujete Linn. The structures of these compounds were established on the basis of spectroscopic analysis.

  17. 4'''-N-demethylspiramycin derivatives: synthesis and evaluation of effectiveness against drug-resistant bacteria.

    PubMed

    Sunazuka, Toshiaki; Shudo, Hiroko; Nagai, Kenichiro; Yoshida, Kiminari; Yamaguchi, Yukie; Hanaki, Hideaki; Omura, Satoshi

    2008-03-01

    18-amino-4''-O-benzoyl-4'''-N-demethyl-18-deoxospiramycins were designed and synthesized. Synthetic strategy involved selective demethylation of the dimethylamino group in forosamine, benzoylation of the hydroxyl group at the C4'' position and reductive N-amination of the formyl group. Antibacterial characteristics of spiramycin derivatives were tested. The derivatives exhibited promising activity against drug-resistant bacterial strains. PMID:18503196

  18. New iridoids from the fruits of Crescentia cujete.

    PubMed

    Wang, Gang; Yin, Wei; Zhou, Zhong-Yu; Hsieh, Kun-Lung; Liu, Ji-Kai

    2010-09-01

    Four new 11-nor-iridoids, 6-O-p-hydroxybenzoyl-10-deoxyeucommiol (1), 6-O-benzoyl-10-deoxyeucommiol (2), 6-O-benzoyl-dihydrocatalpolgenin (a mixture of 3 and 4), as well as two known iridoids, ningpogenin (5) and 6-O-p-hydroxybenzoylaucubin (6), were isolated from the fruits of Crescentia cujete Linn. The structures of these compounds were established on the basis of spectroscopic analysis. PMID:20839124

  19. New phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Dou, De-Qiang; Xu, Liang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai-Xue

    2009-07-01

    Two new phenolic glycosides were isolated from the seeds of Cucurbita moschata. Their structures were elucidated as (2-hydroxy)phenylcarbinyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (1) and 4-beta-D-(glucopyranosyl hydroxymethyl)phenyl 5-O-benzoyl-beta-D-apiofuranosyl(1-->2)-beta-D-glucopyranoside (2) on the basis of spectroscopic analysis and chemical evidence.

  20. Optimizing the use of tazarotene for the treatment of facial acne vulgaris through combination therapy.

    PubMed

    Draelos, Zoe Diana; Tanghetti, Emil A

    2002-02-01

    A multicenter, investigator-masked, randomized, parallel-group study was performed in 440 patients with mild-to-moderate facial acne vulgaris to compare the efficacy and tolerability of tazarotene monotherapy with 3 combination regimens--tazarotene plus benzoyl peroxide gel, tazarotene plus erythromycin/benzoyl peroxide gel, and tazarotene plus clindamycin phosphate lotion. An additional treatment group-monotherapy with clindamycin phosphate lotion-also was included as a reference arm. The only combination therapy to achieve a significantly greater global improvement than tazarotene monotherapy was tazarotene plus clindamycin. For reducing noninflammatory lesions specifically, none of the combination regimens offered significant benefit over tazarotene monotherapy (though tazarotene plus clindamycin and tazarotene plus erythromycin/benzoyl peroxide were significantly more efficacious than clindamycin monotherapy). For reducing inflammatory lesions, tazarotene plus erythromycin/benzoyl peroxide was significantly more efficacious than all the other regimens. Although tazarotene plus clindamycin and tazarotene plus benzoyl peroxide reduced the incidence of adverse effects compared with tazarotene monotherapy, the difference did not achieve statistical significance.

  1. Pilot investigation of the hydrating effects of topical acne medications.

    PubMed

    Zhen, Yaxian; Stoudemayer, Marianne; Vamvakias, George; Kligman, Albert M

    2007-08-01

    Topical therapies are effective in managing acne vulgaris but are associated with local adverse effects such as irritation and dryness. This 4-week pilot study compared skin hydration in 36 healthy adult women randomized to treatment with 1 of 4 topical therapies: 2 different (jar and tube) clindamycin 1%/benzoyl peroxide 5% gels, sodium sulfacetamide 10% lotion, or over-the-counter (OTC) moisturizing cream. Subjects treated with OTC moisturizer or sodium sulfacetamide exhibited decreased water loss, increased water retention, similar or improved levels of skin hydration, and decreased desorption rates. In contrast, subjects treated with jar or tube clindamycin/benzoyl peroxide had increased water loss, decreased water retention, decreased hydration, and increased desorption rates. Skin dryness decreased slightly in the moisturizer group. No serious adverse events occurred. Overall, the OTC moisturizer had the best skin hydration profile. Sodium sulfacetamide demonstrated some moisturizing characteristics, and no clinically relevant differences were noted between jar and tube clindamycin/benzoyl peroxide gels.

  2. Separation of derivatized glucoside anomers using supercritical fluid chromatography.

    PubMed

    Montañés, Fernando; Rose, Paul; Tallon, Stephen; Shirazi, Rahau

    2015-10-30

    Preparative scale supercritical fluid chromatography was used to separate derivatized anomeric monosaccharides. Methyl 2,3,4,6-tetra-O-benzoyl-α-d-glucopyranoside and methyl 2,3,4,6-tetra-O-benzoyl-β-d-glucopyranoside were synthesized by benzoyl derivatization of the parent anomerically pure monosaccharides. The elution profiles of each anomer were studied, suggesting that separation was possible. Mixtures of the compounds were then prepared at different ratios and separation was achieved using carbon dioxide/ethanol mixtures as the mobile phase and GreenSep™ 5micron particle size silica as the stationary phase. Ethanol co-solvent in the mobile phase was required to give a successful separation of the anomers however over the range 6.5-10.4wt% ethanol concentration studied here there was little variation in the degree of separation. In fractionation trials, separation of mixtures into fractions with >98% purity was achieved, with recoveries greater than 96%. PMID:26411481

  3. N-[Eth­yl(2-hy­droxy­eth­yl)carbamo­thio­yl]-3-fluoro­benzamide

    PubMed Central

    Awang, Nor Wahida.; Hasbullah, Siti Aishah; Yusoff, Siti Fairus M.; Yamin, Bohari M.

    2014-01-01

    In the title compound, C12H15FN2O2S, the mol­ecule adopts a cis configuration of the fluoro­benzoyl group with respect to the thiono group about their C—N bond. The dihedral angle between the fluoro­benzoyl group and the thio­urea N2CS fragment is 69.60 (11)°. An intra­molecular N—H⋯O hydrogen bond occurs. In the crystal, mol­ecules form chains along the b-axis direction via O—H⋯S and C—H⋯O hydrogen bonds. PMID:24860375

  4. Structures of new phenolic glycosides from the seeds of Cucurbita moschata.

    PubMed

    Li, Fa-Sheng; Xu, Jing; Dou, De-Qiang; Chi, Xiao-Feng; Kang, Ting-Guo; Kuang, Hai Xue

    2009-04-01

    A new phenolic glycoside and three known compounds were isolated from the seeds of Cucurbita moschata. The structures of the new compound was elucidated as phenylcarbinyl 5-O-(4-hydroxy)benzoyl-beta-D-apiofuranosyl (1-->2)-beta-D-glucopyranoside on the basis of spectroscopic analysis and chemical evidence. Three known compounds were identified as 1-O-benzyl[5-O-benzoyl-beta-D-apiofuranosyl(1-->2)]-beta-D-glucopyranoside 2, cucurbitosides C 3 and A 4, by comparison of the spectral data with reported data. Compound 2 was isolated from this plant for the first time.

  5. Preparation of the different derivatives of the low-molecular-weight porphyran from Porphyra haitanensis and their antioxidant activities in vitro.

    PubMed

    Zhang, Zhongshan; Zhang, Quanbin; Wang, Jing; Zhang, Hong; Niu, Xizhen; Li, Pengcheng

    2009-07-01

    Porphyran extracted from Porphyra haitanensis is a sulfated polysaccharide, which possesses excellent antioxidant activities. In this study, we prepared one low-molecular-weight porphyran and its sulfated, acetylated, phosphorylated and benzoylated derivatives. Their antioxidant activities were investigated including scavenging effect of superoxide, hydroxyl and 1,1-diphenyl-2-picrylhydrazyl radicals. The results of chemical analysis and FT-IR spectrums showed the modification was successful. And in addition, we found that certain derivative exhibited stronger antioxidant activity than low-molecular-weight porphyran. The benzoylated derivative showed the most excellent antioxidant activity in three assays, so this derivative needs to be attended to.

  6. Synthesis of anticholinergic agents: N-methyl-4-piperidinyl alpha-benzoyloxy-alpha-cyclopentylphenylacetate salts.

    PubMed

    Oroshnik, W; Soldati, G

    1978-05-01

    The synthesis of a new anticholinergic agent, N-methyl-4-piperidinyl alpha-benzoyloxy-alpha-cyclopentylphenylacetate, obtained by reacting N-methyl-4-piperidinyl alpha-cyclopentylmandelate with benzoyl chloride in the presence of methyllithium, is reported. This material may be useful as an antiperspirant.

  7. Highly efficient synthesis of O-(2,4-dinitrophenyl)hydroxylamine. Application to the synthesis of substituted N-benzoyliminopyridinium ylides.

    PubMed

    Legault, Claude; Charette, André B

    2003-09-01

    An efficient two-step synthesis of O-(2,4-dinitrophenyl)hydroxylamine is described along with a comparison of its aminating efficiency with O-mesitylenesulfonylhydroxylamine (MSH). It was used in an expedient N-amination/benzoylation procedure involving various substituted pyridines, leading to polysubstituted N-benzoyliminopyridinium ylides, and the scope of its amination power was studied. PMID:12946163

  8. New Initiation Modes for Directed Carbonylative C–C Bond Activation: Rhodium-Catalyzed (3 + 1 + 2) Cycloadditions of Aminomethylcyclopropanes

    PubMed Central

    2016-01-01

    Under carbonylative conditions, neutral Rh(I)-systems modified with weak donor ligands (AsPh3 or 1,4-oxathiane) undergo N-Cbz, N-benzoyl, or N-Ts directed insertion into the proximal C–C bond of aminomethylcyclopropanes to generate rhodacyclopentanone intermediates. These are trapped by N-tethered alkenes to provide complex perhydroisoindoles. PMID:27709913

  9. Tissue-specific PhBPBT expression is differentially regulated in response to endogenous ethylene

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Ethylene is a gaseous plant hormone involved in many physiological processes including senescence, fruit ripening, and defense. Here we show the effects of pollination and wound-induced ethylene signals on transcript accumulation of benzoyl CoA:benzyl alcohol/phenylethanol benzoyltransferase (PhBPBT...

  10. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Folic acid (folacin). 172.345 Section 172.345 Food... Special Dietary and Nutritional Additives § 172.345 Folic acid (folacin). Folic acid (CAS Reg. No. 59-30-3... following prescribed conditions: (a) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b)...

  11. 40 CFR 180.634 - Tembotrione; tolerances for residues.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... of the herbicide tembotrione, including its metabolites and degradates, in or on the commodities... determined by measuring only the sum of tembotrione, 2- benzoyl]-1,3-cyclohexanedione and its metabolite, 2... established for residues of the herbicide tembotrione, including its metabolites and degradates, in or on...

  12. 40 CFR 180.634 - Tembotrione; tolerances for residues.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... of the herbicide tembotrione, including its metabolites and degradates, in or on the commodities... determined by measuring only the sum of tembotrione, 2- benzoyl]-1,3-cyclohexanedione and its metabolite, 2... established for residues of the herbicide tembotrione, including its metabolites and degradates, in or on...

  13. 40 CFR 180.634 - Tembotrione; tolerances for residues.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... of the herbicide tembotrione, including its metabolites and degradates, in or on the commodities... determined by measuring only the sum of tembotrione, 2- benzoyl]-1,3-cyclohexanedione and its metabolite, 2... established for residues of the herbicide tembotrione, including its metabolites and degradates, in or on...

  14. 40 CFR 180.634 - Tembotrione; tolerances for residues.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... of the herbicide tembotrione, including its metabolites and degradates, in or on the commodities... determined by measuring only the sum of tembotrione, 2- benzoyl]-1,3-cyclohexanedione and its metabolite, 2... established for residues of the herbicide tembotrione, including its metabolites and degradates, in or on...

  15. 40 CFR 180.634 - Tembotrione; tolerances for residues.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... of the herbicide tembotrione, including its metabolites and degradates, in or on the commodities... determined by measuring only the sum of tembotrione, 2- benzoyl]-1,3-cyclohexanedione and its metabolite, 2... established for residues of the herbicide tembotrione, including its metabolites and degradates, in or on...

  16. 21 CFR 133.102 - Asiago fresh and asiago soft cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... purified calcium chloride in a quantity not more than 0.02 percent (calculated as anhydrous calcium chloride) of the weight of the milk, is added to set the milk to a semisolid mass. The mass is cut, stirred... benzoyl peroxide with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of...

  17. 21 CFR 133.165 - Parmesan and reggiano cheese.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... equivalent curd formation, or both, with or without purified calcium chloride in a quantity not more than 0.02 percent (calculated as anhydrous calcium chloride) of the weight of the milk, is added to set the... with potassium alum, calcium sulfate, and magnesium carbonate; but the weight of the benzoyl...

  18. Influence of Bleaching on Flavor of 34% Whey Protein Concentrate and Residual Benzoic Acid Concentration in Dried Whey Proteins

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Previous studies have shown that bleaching negatively affects the flavor of 70% whey protein concentrate (WPC70), but bleaching effects on lower-protein products have not been established. Benzoyl peroxide (BP), a whey bleaching agent, degrades to benzoic acid (BA) and may elevate BA concentrations...

  19. Influence of bleaching on flavor of 34% whey protein concentrate and residual benzoic acid concentration in dried whey products

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Previous studies have shown that bleaching negatively affects the flavor of 70% whey protein concentrate (WPC70), but bleaching effects on lower-protein products have not been established. Benzoyl peroxide (BP), a whey bleaching agent, degrades to benzoic acid (BA) and may elevate BA concentrations...

  20. 21 CFR 177.2420 - Polyester resins, cross-linked.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ...: Total not to exceed 1.5 percent, except that methyl ethyl ketone peroxide may be used as the sole catalyst at levels not to exceed 2 percent. Azo-bis-isobutyronitrile Benzoyl peroxide tert-Butyl perbenzoate Chlorbenzoyl peroxide Cumene hydroperoxide Dibutyltin oxide (CAS Reg. No. 818-08-6) For use in...

  1. 77 FR 10536 - Draft and Revised Draft Guidances for Industry Describing Product-Specific Bioequivalence...

    Federal Register 2010, 2011, 2012, 2013, 2014

    2012-02-22

    ... (ANDAs). In the Federal Register of June 11, 2010 (75 FR 33311), FDA announced the availability of a... comment. Recommendations were last announced in the Federal Register of January 25, 2012 (77 FR 3777... ingredients: A Alendronate Sodium Alendronate Sodium; Cholecalciferol B Benzoyl Peroxide;...

  2. Glutathione reductase-catalyzed cascade of redox reactions to bioactivate potent antimalarial 1,4-naphthoquinones--a new strategy to combat malarial parasites.

    PubMed

    Müller, Tobias; Johann, Laure; Jannack, Beate; Brückner, Margit; Lanfranchi, Don Antoine; Bauer, Holger; Sanchez, Cecilia; Yardley, Vanessa; Deregnaucourt, Christiane; Schrével, Joseph; Lanzer, Michael; Schirmer, R Heiner; Davioud-Charvet, Elisabeth

    2011-08-01

    Our work on targeting redox equilibria of malarial parasites propagating in red blood cells has led to the selection of six 1,4-naphthoquinones, which are active at nanomolar concentrations against the human pathogen Plasmodium falciparum in culture and against Plasmodium berghei in infected mice. With respect to safety, the compounds do not trigger hemolysis or other signs of toxicity in mice. Concerning the antimalarial mode of action, we propose that the lead benzyl naphthoquinones are initially oxidized at the benzylic chain to benzoyl naphthoquinones in a heme-catalyzed reaction within the digestive acidic vesicles of the parasite. The major putative benzoyl metabolites were then found to function as redox cyclers: (i) in their oxidized form, the benzoyl metabolites are reduced by NADPH in glutathione reductase-catalyzed reactions within the cytosols of infected red blood cells; (ii) in their reduced forms, these benzoyl metabolites can convert methemoglobin, the major nutrient of the parasite, to indigestible hemoglobin. Studies on a fluorinated suicide-substrate indicate as well that the glutathione reductase-catalyzed bioactivation of naphthoquinones is essential for the observed antimalarial activity. In conclusion, the antimalarial naphthoquinones are suggested to perturb the major redox equilibria of the targeted infected red blood cells, which might be removed by macrophages. This results in development arrest and death of the malaria parasite at the trophozoite stage.

  3. Highly stereoselective synthesis of (borylmethyl)cyclopropylamines by copper-catalyzed aminoboration of methylenecyclopropanes.

    PubMed

    Sakae, Ryosuke; Matsuda, Naoki; Hirano, Koji; Satoh, Tetsuya; Miura, Masahiro

    2014-02-21

    A Cu-catalyzed aminoboration of 1-methylenecyclopropanes with bis(pinacolato)diboron and O-benzoyl-N,N-dialkylhydroxylamines has been developed. The Cu catalysis provides a rapid and concise access to (borylmethyl)cyclopropylamines in a highly regio- and diastereoselective manner. The products obtained can be useful building blocks for the synthesis of potential antidepressants, trans-2-arylcyclopropylamine derivatives. PMID:24491169

  4. Safe Preparation of HCl and DCl for IR Spectroscopy

    ERIC Educational Resources Information Center

    Furlong, William R.; Grubbs, W. Tandy

    2005-01-01

    The widely used method of synthesizing HCl and DCl gases for infrared analysis by hydrolysis of benzoyl chloride includes a potentially dangerous final step whereby the frozen product is allowed to heat and expand into an infrared gas cell. The subsequent rapid rise in vapor pressure can "pop" open glass joints in the vacuum line and vent the…

  5. The "Mushroom Cloud" Demonstration Revisited

    ERIC Educational Resources Information Center

    Panzarasa, Guido; Sparnacci, Katia

    2013-01-01

    A revisitation of the classical "mushroom cloud" demonstration is described. Instead of aniline and benzoyl peroxide, the proposed reaction involves household chemicals such as alpha-pinene (turpentine oil) and trichloroisocyanuric acid ("Trichlor") giving an impressive demonstration of oxidation and combustion reactions that…

  6. Characterization of AlFe-pillared Unye bentonite: A study of the surface acidity and catalytic property

    NASA Astrophysics Data System (ADS)

    Caglar, Bulent; Cubuk, Osman; Demir, Ersin; Coldur, Fatih; Catir, Mustafa; Topcu, Cihan; Tabak, Ahmet

    2015-06-01

    Aluminium-iron-pillared bentonite has been prepared by incorporation of the iron mixed aluminium-polyoxocation into bentonite layers and characterized by the powder X-ray diffraction, Fourier transform infrared, thermal analysis and surface area measurement techniques. The characteristic d001 basal spacing of raw bentonite increased with the pillaring process and reached to 18.05 Å. The siloxane layers of bentonite were perturbed and the positions of Si-O stretching vibrations were altered by pillaring process. However, these pillars in the interlayer gallery spacing enhanced the thermal stability of bentonite. The new micropores were formed by the pillaring process and the specific surface area of raw bentonite increased by ca. 2-fold for aluminium-iron-pillared bentonite. FTIR spectra and thermal analysis curves of pyridine adsorbed samples clearly show that the surface Lewis acidity of aluminium-iron-pillared bentonite is greater than that of raw bentonite. Raw and aluminium-iron-pillared bentonites have been utilized as solid catalysts for benzoylation of benzene with benzoyl chloride. The aluminium-iron-pillared bentonite catalyst showed promising catalytic activity whereas raw bentonite showed no catalytic activity in benzoylation of benzene with benzoyl chloride.

  7. Direct interactions between the coiled-coil tip of DksA and the trigger loop of RNA polymerase mediate transcriptional regulation

    Technology Transfer Automated Retrieval System (TEKTRAN)

    E. coli DksA is in a class of transcription factors that modify RNA polymerase (RNAP) in all three kingdoms of life. DksA potentiates the effects of the global regulator ppGpp and the initiating NTP, controlling transcription initiation without binding to DNA. Incorporating benzoyl-phenylalanine (Bp...

  8. Synthesis and structure-activity relationship of pyripyropene A derivatives as potent and selective acyl-CoA:cholesterol acyltransferase 2 (ACAT2) inhibitors: part 1.

    PubMed

    Ohtawa, Masaki; Yamazaki, Hiroyuki; Ohte, Satoshi; Matsuda, Daisuke; Ohshiro, Taichi; Rudel, Lawrence L; Omura, Satoshi; Tomoda, Hiroshi; Nagamitsu, Tohru

    2013-03-01

    In an effort to develop potent and selective inhibitors toward ACAT2, structure-activity relationship studies were carried out using derivatives based on pyripyropene A (PPPA, 1). We have successfully developed novel PPPA derivatives with a 7-O-substituted benzoyl substituent that significantly exhibit more potent ACAT2 inhibitory activity and higher ACAT2 isozyme selectivity than 1. PMID:23369538

  9. METHOD OF PREPARING COMPLEXES OF PLUTONIUM WITH DIKETONES

    DOEpatents

    Dixon, J.S.; Katz, J.J.; Orlemann, E.F.

    1961-06-20

    A process is described for sepsrating Pu from an aqueous alkaline solution by either precipitating with a beta -diketone or extracting into a solution of the beta -dixetone in an organic water-immiscible solvent. Acetyl acetone and benzoyl acetone are the beta -diketones used.

  10. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... following prescribed conditions: (a) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b) Folic... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Folic acid (folacin). 172.345 Section 172.345 Food... Special Dietary and Nutritional Additives § 172.345 Folic acid (folacin). Folic acid (CAS Reg. No....

  11. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... following prescribed conditions: (a) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b) Folic... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Folic acid (folacin). 172.345 Section 172.345 Food... Special Dietary and Nutritional Additives § 172.345 Folic acid (folacin). Folic acid (CAS Reg. No....

  12. 21 CFR 172.345 - Folic acid (folacin).

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ...) Folic acid is the chemical N- amino]benzoyl]-L-glutamic acid. (b) Folic acid meets the specifications of.../federal-register/cfr/ibr-locations.html. (c) Folic acid may be added to foods subject to a standard of... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Folic acid (folacin). 172.345 Section 172.345...

  13. Möbius Aromatic Core-Modified Heterocyclic [20] Macrocycles (4.1.1) with a Protruding N-Methyl Pyrrole Ring.

    PubMed

    Mallick, Abhijit; Rath, Harapriya

    2016-04-01

    Herein, we report the first synthesis of an unorthodox tripyrrane moiety from the regioselective β-benzoylation of pyrrole and the acid-catalyzed condensation of the desired precursors. A [3+1] Mac Donald type condensation strategy for this tripyrrane has led to the exclusive isolation of two hitherto-unknown aromatic [20] heterocyclic macrocycles (4.1.1). PMID:26812474

  14. Nucleophilic and electrophilic double aroylation of chalcones with benzils promoted by the dimsyl anion as a route to all carbon tetrasubstituted olefins.

    PubMed

    Ragno, Daniele; Bortolini, Olga; Fantin, Giancarlo; Fogagnolo, Marco; Giovannini, Pier Paolo; Massi, Alessandro

    2015-02-01

    Dimsyl anion promoted the polarity reversal of benzils in a Stetter-like reaction with chalcones to give 2-benzoyl-1,4-diones (double aroylation products), which, in turn, were converted into the corresponding tetrasubstituted olefins via aerobic oxidative dehydrogenation catalyzed by Cu(OAc)2. PMID:25542390

  15. The bamA gene for anaerobic ring fission is widely distributed in the environment

    PubMed Central

    Porter, Abigail W.; Young, Lily Y.

    2013-01-01

    Benzoyl-CoA is the signature central metabolite associated with the anaerobic metabolism of a diverse range of compounds such as humic acid, lignin, amino acids, and industrial chemicals. Aromatic chemicals with different upstream degradation pathways all funnel into the downstream benzoyl-CoA pathway. Different genes encoding enzymes of the benzoyl-CoA pathway could be used as biomarkers for the anaerobic benzoyl-CoA pathway, however, the ring opening hydrolase, encoded by the bamA gene, is ideal because it is detected under a range of respiratory conditions, including under denitrifying, iron-reducing, sulfate-reducing, and fermentative conditions. This work evaluated DNA samples from six diverse environments for the presence of the bamA gene, and had positive results for every sample. Individual bamA gene clones from these sites were compared to published genome sequences. The clone sequences were distributed amongst the genome sequences, although there were clone sequences from two of the analyzed sites that formed a unique clade. Clone sequences were then grouped by site and analyzed with a functional operational taxonomic unit based clustering program to compare the bamA gene diversity of these sites to that of several locations reported in the literature. The results showed that the sequence diversity of the sites separated into two clusters, but there was no clear trend that could be related to the site characteristics. Interestingly, two pristine freshwater sites formed a subgroup within one of the larger clusters. Thus far the bamA gene has only been examined within the context of contaminated environments, however, this study demonstrates that the bamA gene is also detected in uncontaminated sites. The widespread presence of the bamA gene in diverse environments suggests that the anaerobic benzoyl-CoA pathway plays an important role in the global carbon cycle that has thus far been understudied. PMID:24133487

  16. Crystal structure and absolute configuration of (3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-(2-chloro-4-nitro­benzamido)-2-hy­droxy­prop­yl]deca­hydro­isoquinoline-3-carboxamide and (3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-[(S)-1-(2-chloro-4-nitro­benzoyl)pyrrolidin-2-yl]-2-hy­droxy­eth­yl}deca­hydro­iso­quinoline-3-carboxamide

    PubMed Central

    Maxson, Tucker; Bertke, Jeffery A.; Gray, Danielle L.; Mitchell, Douglas A.

    2015-01-01

    The crystal structure and absolute configuration of the two new title nelfinavir analogs, C24H35ClN4O5, (I), and C27H39ClN4O5, (II), have been determined. Each of these mol­ecules exhibits a number of disordered moieties. There are intra­molecular N—H⋯O hydrogen bonds in both (I) and (II). In (I) it involves the two carboxamide groups, while in (II) it involves the N-tert-butyl carboxamide group and the 2-hydroxyl O atom. The inter­molecular hydrogen bonding in (I) (O—H⋯O and N—H⋯O) leads to two-dimensional sheets that extend parallel to the ac plane. The inter­molecular hydrogen bonding in (II) (O—H⋯O) leads to chains that extend parallel to the a axis. PMID:26594520

  17. Second monoclinic form of (E)-3-(4-fluoro­phen­yl)-1-phenyl­prop-2-en-1-one

    PubMed Central

    Arias-Ruiz, Saira N.; Romero, Nancy; Lobato-García, Carlos E.; Gómez-Rivera, Abraham; Mendoza, Angel

    2013-01-01

    The unit-cell dimensions and space group of the second monoclinic polymorph of the title compound, C15H11FO, differ from those of the previously reported form [Jing (2009 ▶). Acta Cryst. E65, o2515]. The title compound shows an E conformation of the C=C bond with the 4-fluoro­phenyl group opposite to the benzoyl group. The torsion angle of between the planes of the 4-fluoro­phenyl and benzoyl groups is 10.53 (6)°. In the crystal, weak C—H⋯O and C—H⋯F inter­actions form a cross-linked packing motif, building sheets parallel to (-102). PMID:24454121

  18. Photoremovable hydroxyl group protection. Use of the p-tolylsulfonyl protecting group in. beta. -disaccharide synthesis

    SciTech Connect

    Binkley, R.W.; Koholic, D.J. )

    1989-07-21

    The p-tolylsulfonyl group has been shown to a photoremovable group effective for protection of carbohydrates during disaccharide synthesis. The formation of the versatile, p-tolylsulfonyl-protected disaccharide 13 (methyl 3-O-(4-O-benzoyl-3-O-benzyl-2,6-dideoxy-{beta}-D-arabino-hexopyranosyl)-2,6-dideoxy-4-O-(p-tolylsulfonyl)-{alpha}-D-arabino-hexopyranoside) was accomplished by silver silicate catalyzed coupling of methyl 2,6-dideoxy-4-O-(p-tolylsulfonyl)-{alpha}-D-arabino-hexopyranoside (7) with 4-O-benzyl-2,6-dideoxy-{alpha}-D-arabino-hexopyranosyl bromide (8). Each of the three protecting groups (benzyl, benzoyl, and p-tolylsulfonyl) present in 13 was removed regioselectively under nonacidic conditions.

  19. Management strategies for acne vulgaris

    PubMed Central

    Whitney, Kristen M; Ditre, Chérie M

    2011-01-01

    Clinical question: What are the most effective treatment(s) for mild, moderate, severe, and hormonally driven acne? Results: Mild acne responds favorably to topical treatments such as benzoyl peroxide, salicylic acid, and a low-dose retinoid. Moderate acne responds well to combination therapy comprising-topical benzoyl peroxide, antibiotics, and/or retinoids, as well as oral antibiotics in refractory cases and oral contraceptive pills for female acne patients. Severe nodulocystic acne vulgaris responds best to oral isotretinoin therapy. In female patients with moderate to severe acne, facial hair, loss of scalp hair and irregular periods, polycystic ovarian syndrome should be considered and appropriate treatment with hormonal modulation given. Adjunctive procedures can also be considered for all acne patients. Implementation: Pitfalls to avoid when treating acne: treatment of acne in women of child-bearing age; familiarization of all acne treatments in order to individualize management for patients; indications for specialist referral. PMID:21691566

  20. Bacteriology of chronic leg ulcers.

    PubMed

    Lookingbill, D P; Miller, S H; Knowles, R C

    1978-12-01

    The quantitative bacteriology of 13 chronic leg ulcers was sequentially assessed by both swab and biopsy culture techniques, and the effect of either a 10% benzoyl peroxide lotion or placebo lotion was evaluated. There was good correlation between the swab and biopsy culture techniques in 12 of the 17 instances where simultaneous swabs and biopsies were done. Though the benzoyl peroxide did not favorably affect the bacterial flora, ulcer healing did appear to correlate with quantitative bacterial counts. THREE of five ulcers containing fewer than 10(5) organisms per gram of tissue or per centimeter of ulcer surface area healed, while none of eight ulcers containing more than 10(5) organisms healed. Quantitative bacteriological measurements can serve as useful tools in evaluating healing of leg ulcers.

  1. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)

    DOEpatents

    Samsel, Edward G.

    1992-01-01

    A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-.alpha.-benzoylamino-4-boronocinnamic acid, asymmetrically hydrogenating the z-.alpha.-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA.

  2. Enantioselective synthesis of L-(-)-4- boronophenylalanine (L-BPA)

    DOEpatents

    Samsel, E.G.

    1992-10-20

    A method of making substantially pure L-BPA is disclosed. The method includes the steps of reacting 4-bromobenzaldehyde with ethylene glycol to form 4-bromobenzaldehyde ethylene glycol acetal, sequentially reacting 4-bromobenzaldehyde ethyleneglycol acetal with Mg to produce the Grignard reagent and thereafter reacting with tributyl borate and then converting to an acid environment to form 4-boronobenzaldehyde, reacting 4-boronobenzaldehyde with diethanol amine to form 4-boronobenzaldehyde diethanolamine ester, condensing the 4-boronobenzaldehyde diethanolamine ester with 2-phenyl-2-oxazolin-5-one to form an azlactone, reacting the azlactone with an alkali metal hydroxide to form z-[alpha]-benzoylamino-4boronocinnamic acid, asymmetrically hydrogenating the z-[alpha]-benzoylamino-4-boronocinnamic acid in the presence of a catalyst of a cheltate complex of rhodium (I) with chiral bisphosphines to form L-(+)-N-benzoyl-4-boronophenylalanine, and thereafter acidifying the L-(+)-N-benzoyl-4-boronophenylalanine in an organic medium to produce L-BPA. 3 figs.

  3. Phloroglucinol and Terpenoid Derivatives from Hypericum cistifolium and H. galioides (Hypericaceae)

    PubMed Central

    Crockett, Sara L.; Kunert, Olaf; Pferschy-Wenzig, Eva-Maria; Jacob, Melissa; Schuehly, Wolfgang; Bauer, Rudolf

    2016-01-01

    A new simple phloroglucinol derivative characterized as 1-(6-hydroxy-2,4-dimethoxyphenyl)-2-methyl-1-propanone (1) was isolated from Hypericum cistifolium (Hypericaceae) as a major constituent of the non-polar plant extract. Minor amounts of this new compound, in addition to two known structurally related phloroglucinol derivatives (2 and 3), and two new terpenoid derivatives characterized, respectively, as 2-benzoyl-3,3-dimethyl-4R,6S-bis-(3-methylbut-2-enyl)-cyclohexanone (4a) and 2-benzoyl-3,3-dimethyl-4S,6R-bis-(3-methylbut-2-enyl)-cyclohexanone (4b), were isolated from a related species, H. galioides Lam. The chemical structures were established using 2D-NMR spectroscopy and mass spectrometry. These compounds were evaluated in vitro for antimicrobial activity against a panel of pathogenic microorganisms and anti-inflammatory activity through inhibition of COX-1, COX-2, and 5-LOX catalyzed LTB4 formation. PMID:27458464

  4. Design and synthesis of diamide-coupled benzophenones as potential anticancer agents.

    PubMed

    Zabiulla; Shamanth Neralagundi, H G; Bushra Begum, A; Prabhakar, B T; Khanum, Shaukath Ara

    2016-06-10

    A series of diamide-coupled benzophenone, 2-(4-benzoyl-phenoxy)-N-{2-[2-(4-benzoyl-phenoxy)-acetylamino]-phenyl}-acetamide analogues (9a-l) were synthesized by multistep reactions and all compounds were well characterized. Among the series (9a-l), compound 9k with three methyl groups at ortho position in rings A, B, and D and bromo group at the para position in ring E was selected as a lead compound by screening through multiple cancer cell types by in-vitro cytotoxic and antiproliferative assay systems. Also, the cytotoxic nature of the compound 9k resulted the regression of the tumor growth in-vivo, which could be due to decreased vascularisation in the peritoneum lining of the mice which regress the tumor growth. The results were reconfirmed in-vivo chorioallantoic membrane model which indicates a scope of developing 9k into potent anticancer drug in near future. PMID:27027818

  5. 1,2-diketones promoted degradation of poly(epsilon-caprolactone)

    SciTech Connect

    Danko, Martin; Borska, Katarina; Ragab, Sherif Shaban; Janigova, Ivica; Mosnacek, Jaroslav

    2012-07-11

    Photochemical reactions of Benzil and Camphorquinone were used for modification of poly({epsilon}-caprolactone) polymer films. Photochemistry of dopants was followed by infrared spectroscopy, changes on polymer chains of matrix were followed by gel permeation chromatography. Benzoyl peroxide was efficiently photochemically generated from benzyl in solid polymer matrix in the presence of air. Following decomposition of benzoyl peroxide led to degradation of matrix. Photochemical transformation of benzil in vacuum led to hydrogen abstraction from the polymer chains in higher extent, which resulted to chains recombination and formation of gel. Photochemical transformation of camphorquinone to corresponding camphoric peroxide was not observed. Only decrease of molecular weight of polymer matrix doped with camphorquinone was observed during the irradiation.

  6. Newer approaches to the treatment of acne vulgaris.

    PubMed

    Simonart, Thierry

    2012-12-01

    The multifactorial etiology of acne vulgaris makes it challenging to treat. Current treatments include topical retinoids, benzoyl peroxide, topical and systemic antibiotics, azelaic acid, and systemic isotretinoin. Adjunctive and/or emerging approaches include topical dapsone, taurine bromamine, resveratrol, chemical peels, optical treatments, as well as complementary and alternative medications. The purpose of this paper is to discuss the therapies available for acne and their latest developments, including new treatment strategies (i.e. re-evaluation of the use of oral antibiotics and avoidance of topical antibiotic monotherapy, use of subantimicrobial antibiotic dosing, use of low-dose isotretinoin, optical treatments), new formulations (microsponges, liposomes, nanoemulsions, aerosol foams), new combinations (fixed-combination products of topical retinoids and topical antibiotics [essentially clindamycin] or benzoyl peroxide), new agents (topical dapsone, taurine bromamine, resveratrol) and their rationale and likely place in treatment. Acne vaccines, topical natural antimicrobial peptides, and lauric acid represent other promising therapies. PMID:22920095

  7. Benzaldehyde dehydrogenase from chitosan-treated Sorbus aucuparia cell cultures.

    PubMed

    Gaid, Mariam M; Sircar, Debabrata; Beuerle, Till; Mitra, Adinpunya; Beerhues, Ludger

    2009-09-01

    Cell cultures of Sorbus aucuparia respond to the addition of chitosan with the accumulation of the biphenyl phytoalexin aucuparin. The carbon skeleton of this inducible defense compound is formed by biphenyl synthase (BIS) from benzoyl-CoA and three molecules of malonyl-CoA. The formation of benzoyl-CoA proceeds via benzaldehyde as an intermediate. Benzaldehyde dehydrogenase (BD), which converts benzaldehyde into benzoic acid, was detected in cell-free extracts from S. aucuparia cell cultures. BD and BIS were induced by chitosan treatment. The preferred substrate for BD was benzaldehyde (K(m)=49 microM). Cinnamaldehyde and various hydroxybenzaldehydes were relatively poor substrates. BD activity was strictly dependent on the presence of NAD(+) as a cofactor (K(m)=67 microM).

  8. Phloroglucinol and Terpenoid Derivatives from Hypericum cistifolium and H. galioides (Hypericaceae).

    PubMed

    Crockett, Sara L; Kunert, Olaf; Pferschy-Wenzig, Eva-Maria; Jacob, Melissa; Schuehly, Wolfgang; Bauer, Rudolf

    2016-01-01

    A new simple phloroglucinol derivative characterized as 1-(6-hydroxy-2,4-dimethoxyphenyl)-2-methyl-1-propanone (1) was isolated from Hypericum cistifolium (Hypericaceae) as a major constituent of the non-polar plant extract. Minor amounts of this new compound, in addition to two known structurally related phloroglucinol derivatives (2 and 3), and two new terpenoid derivatives characterized, respectively, as 2-benzoyl-3,3-dimethyl-4R,6S-bis-(3-methylbut-2-enyl)-cyclohexanone (4a) and 2-benzoyl-3,3-dimethyl-4S,6R-bis-(3-methylbut-2-enyl)-cyclohexanone (4b), were isolated from a related species, H. galioides Lam. The chemical structures were established using 2D-NMR spectroscopy and mass spectrometry. These compounds were evaluated in vitro for antimicrobial activity against a panel of pathogenic microorganisms and anti-inflammatory activity through inhibition of COX-1, COX-2, and 5-LOX catalyzed LTB4 formation. PMID:27458464

  9. N′-(Adamantan-2-yl­idene)benzo­hydrazide

    PubMed Central

    Almutairi, Maha S.; El-Emam, Ali A.; El-Brollosy, Nasser R.; Said-Abdelbaky, Mohammed; García-Granda, Santiago

    2012-01-01

    The title mol­ecule, C17H20N2O, is a functionalized hydrazine with benzoyl and adamantyl substituents attached to the two hydrazine N atoms. In the crystal, mol­ecules are linked via N—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. There are also C—H⋯O, C—H⋯N and C—H⋯π inter­actions present within the chains. PMID:22798901

  10. (-)-Norcocaine.

    PubMed

    Zhu, N; Reynolds, M; Klein, C L; Trudell, M

    1994-12-15

    The title compound, [2R,3S-(2 beta,3 beta)]-methyl 3-(benzoyloxy)-8-azabicyclo[3.2.1]octane-2-carboxylate, C16H19NO4, is a metabolite of the tropane alkaloid cocaine. The molecule crystallized as the free base with the piperidine ring in a chair conformation. The tropane ring system and its methoxycarbonyl and benzoyl groups are rigid; only rotational flexibility is allowed in the conformation of the substituents.

  11. Synthesis of fagopyritols A1 and B1 from D-chiro-inositol.

    PubMed

    Cid, M Belén; Alfonso, Francisco; Martín-Lomas, Manuel

    2004-09-13

    Fagopyritol A1 (3-O-alpha-d-galactopyranosyl-d-chiro-inositol) and fagopyritol B1 (2-O-alpha-d-galactopyranosyl-d-chiro-inositol) have been synthesized by glycosylation of the diequatorial diol 1,4,5,6-tetra-O-benzoyl-d-chiro-inositol, readily obtained from d-chiro-inositol, with 2,3,4,6-tetra-O-benzyl-d-galactopyranosyl trichloroacetimidate. PMID:15337459

  12. Synthesis and antimicrobial activity of new substituted anilinobenzimidazoles.

    PubMed

    Nofal, Z M; Fahmy, H H; Mohamed, H S

    2002-06-01

    A series of benzimidazole derivatives carrying different heterocycles such as 1,2,3-thiadiazole, 1,3,4-thiadiazole, thiazolidine, 2,3-dihydro-thiazole, 1,3,4-oxadiazole, semicarbazone and substituted thiosemi-carbazones were synthesized. Also a series of 1-methylbenzimidazole carrying hydroxy ethyl-amide, substituted sulfonyl hydrazide and benzoyl hydrazide from aminobenzoyl group at position 2 of 1-methylbenzimidazole were synthesized. The antimicrobial evaluation of some of the new compounds was carried out. PMID:12135093

  13. Synthesis, spectral characterization, and biological activity of some new substituted 10H-phenothiazines, its ribofuranosides, and sulfones.

    PubMed

    Gautam, Naveen; Ajmera, Neha; Gupta, Shikha; Gautam, D C

    2010-03-01

    This article describes the synthesis of new substituted 10 H-phenothiazines by Smiles rearrangement. These compounds are then used as a base to form ribofuranosides by treating them with a sugar (1-O-acetyl-2,3,5-tri-O-benzoyl-beta-ribofuranose). On oxidation with hydrogen peroxide in glacial acetic acid, these phenothiazines yield their sulfones. These compounds are screened for antioxidant and antimicrobial activity and their structure has been established by elemental analysis and spectroscopic data. PMID:20408049

  14. Antibiotic resistance and acne: where we stand and what the future holds.

    PubMed

    Bowe, Whitney P

    2014-06-01

    Antibiotic resistance is described as "a global public health challenge" and a "major health security challenge of the 21st century" by global health authorities,1 and there is a growing need for dermatologists to counteract it in their treatments of acne.3,4 Antibiotic limiting regimens, such as a combination of topical retinoids and benzoyl peroxide, have shown effectiveness in the treatment of acne; and topical probiotics could also play a needed role.

  15. Design, synthesis, and bioactivity of putative tubulin ligands with adamantane core.

    PubMed

    Zefirova, Olga N; Nurieva, Evgeniya V; Lemcke, Heiko; Ivanov, Andrei A; Shishov, Dmitrii V; Weiss, Dieter G; Kuznetsov, Sergei A; Zefirov, Nikolay S

    2008-09-15

    Several adamantane-based taxol mimetics were synthesized and found to be cytotoxic at micromolar concentrations and to cause tubulin aggregation. The extent of the aggregation is maximal for N-benzoyl-(2R,3S)-phenylisoseryloxyadamantane (5) and is very sensitive to the structural modifications. A hybrid compound (15), combining adamantane-based taxol mimetic with colchicine was synthesized and found to possess both microtubule depolymerizing and microtubule bundling activities in A549 human lung carcinoma cells. PMID:18715782

  16. Heteroarylation of organometallic derivatives of azoles by n-acylbenzopyridinium salts

    SciTech Connect

    Sheinkman, A.K.; Chmilenko, T.S.; Nezdiiminoga, T.N.; Tertov, B.A.; Koshchienko, Yu.V.; Klyuev, N.A.

    1986-07-20

    The dimerization products 1,1'-dimethyl-2,2'-bibenzimidazolyl and 2,2'-dibenzoyl-1,1',2,2'-tetrahydro-1,1'-biisoquinoline were isolated in the reaction of 1-methyl-2-imidazolyl- and 1-methyl-2-benzimidazolylmagnesium bromides with isoquinoline (quinoline) in the presence of benzoyl chloride together with the products from the heteroarylation of benzimidazole (imidazole). Their formation indicates the possibility of reaction by the SET mechanism.

  17. Goldenhar syndrome and hereditary tyrosinemia type 1.

    PubMed

    Al-Sayed, Moeen A; Asmari, Ali M; Rashed, Mohammed S

    2002-12-01

    We report a case of Goldenhar syndrome and hereditary tyrosinemia type 1 (HTT1), to our knowledge an association not previously described. This case further increases the diversity of observations and clinical descriptions of patients with this complex syndrome. We discuss pathogenetic aspects, and demonstrate further evidence of the effectiveness of 2-(2-nitro-4-trifluoromethyl benzoyl)-1,3-cyclohexanedione in the treatment of HTT1.

  18. Iridoid glycosides from Gmelina arborea.

    PubMed

    Tiwari, Neerja; Yadav, Akhilesh K; Srivastava, Pooja; Shanker, Karuna; Verma, Ram K; Gupta, Madan M

    2008-09-01

    Three iridoid glycosides 6-O-(3''-O-benzoyl)-alpha-L-rhamnopyranosylcatalpol (1a), 6-O-(3''-O-trans-cinnamoyl)-alpha-L-rhamnopyranosylcatalpol (2a) and 6-O-(3''-O-cis-cinnamoyl)-alpha-L-rhamnopyranosylcatalpol (3a) were isolated from aerial parts of Gmelina arborea and structures were elucidated by spectral analysis. Additionally a known iridoid 6-O-(3'', 4''-O-dibenzoyl)-alpha-L-rhamnopyranosylcatalpol (4) was also isolated and identified. PMID:18684476

  19. Synthesis of fagopyritols A1 and B1 from D-chiro-inositol.

    PubMed

    Cid, M Belén; Alfonso, Francisco; Martín-Lomas, Manuel

    2004-09-13

    Fagopyritol A1 (3-O-alpha-d-galactopyranosyl-d-chiro-inositol) and fagopyritol B1 (2-O-alpha-d-galactopyranosyl-d-chiro-inositol) have been synthesized by glycosylation of the diequatorial diol 1,4,5,6-tetra-O-benzoyl-d-chiro-inositol, readily obtained from d-chiro-inositol, with 2,3,4,6-tetra-O-benzyl-d-galactopyranosyl trichloroacetimidate.

  20. Copper-catalyzed electrophilic amination of sodium sulfinates at room temperature.

    PubMed

    Zhu, Haibo; Shen, Yajing; Deng, Qinyue; Tu, Tao

    2015-11-28

    By using O-benzoyl hydroxylamines as amine sources, the first convenient copper-catalyzed electrophilic amination of sodium sulfinates has been realized. Even with 2 mol% catalyst loading, the protocol provided an efficient and straightforward synthesis of a broad range of functional sulfonamides under ambient reaction conditions without an additional base and ligand. Based on the control experiments, a plausible mechanism was proposed. PMID:26419424

  1. Spiroquinazoline, a novel substance P inhibitor with a new carbon skeleton, isolated from Aspergillus flavipes.

    PubMed

    Barrow, C J; Sun, H H

    1994-04-01

    A novel substance P inhibitor, spiroquinazoline [1], was isolated from the fungus Aspergillus flavipes, which was originally obtained from soil. The structure of 1 was determined by analysis of spectroscopic data and 1 was shown to contain a new carbon skeleton containing a spiro-carbon center. Also isolated from the same culture extract were the new natural product, benzodiazepiedione [3], and the known compounds, acyl aszonalenin [4], N-benzoyl-L-phenylalaninol, and seven diketopiperazines. PMID:7517439

  2. Synthesis of 9-Aminoacridine Derivatives as Anti-Alzheimer Agents.

    PubMed

    Munawar, Rabya; Mushtaq, Nousheen; Arif, Sadia; Ahmed, Ahsaan; Akhtar, Shamim; Ansari, Sumaira; Meer, Sadia; Saify, Zafar S; Arif, Muhammad

    2016-05-01

    In the present study, some 9-aminoacridine derivatives have been synthesized by condensation of 9-aminoacridine with substituted phenacyl, benzoyl, and benzyl halides (RM1-RM6). Compounds were investigated for acetylcholinesterase and butyrylcholinesterase inhibition potential, considering these enzymes playing a key role in Alzheimer's disease. All derivatives showed better inhibition of enzymes than the standard galantamine, whereas except RM4, all exhibit better results than tacrine, a well-known acridine derivative used for the treatment of Alzheimer's disease. PMID:26385945

  3. One-pot, two-step desymmetrization of symmetrical benzils catalyzed by the methylsulfinyl (dimsyl) anion.

    PubMed

    Ragno, Daniele; Bortolini, Olga; Giovannini, Pier Paolo; Massi, Alessandro; Pacifico, Salvatore; Zaghi, Anna

    2014-08-14

    An operationally simple one-pot, two-step procedure for the desymmetrization of benzils is herein described. This consists in the chemoselective cross-benzoin reaction of symmetrical benzils with aromatic aldehydes catalyzed by the methyl sulfinyl (dimsyl) anion, followed by microwave-assisted oxidation of the resulting benzoylated benzoins with nitrate, avoiding the costly isolation procedure. Both electron-withdrawing and electron-donating substituents may be accommodated on the aromatic rings of the final unsymmetrical benzil. PMID:24967946

  4. A sacrificial millipede altruistically protects its swarm using a drone blood enzyme, mandelonitrile oxidase.

    PubMed

    Ishida, Yuko; Kuwahara, Yasumasa; Dadashipour, Mohammad; Ina, Atsutoshi; Yamaguchi, Takuya; Morita, Masashi; Ichiki, Yayoi; Asano, Yasuhisa

    2016-06-06

    Soldiers of some eusocial insects exhibit an altruistic self-destructive defense behavior in emergency situations when attacked by large enemies. The swarm-forming invasive millipede, Chamberlinius hualienensis, which is not classified as eusocial animal, exudes irritant chemicals such as benzoyl cyanide as a defensive secretion. Although it has been thought that this defensive chemical was converted from mandelonitrile, identification of the biocatalyst has remained unidentified for 40 years. Here, we identify the novel blood enzyme, mandelonitrile oxidase (ChuaMOX), which stoichiometrically catalyzes oxygen consumption and synthesis of benzoyl cyanide and hydrogen peroxide from mandelonitrile. Interestingly the enzymatic activity is suppressed at a blood pH of 7, and the enzyme is segregated by membranes of defensive sacs from mandelonitrile which has a pH of 4.6, the optimum pH for ChuaMOX activity. In addition, strong body muscle contractions are necessary for de novo synthesis of benzoyl cyanide. We propose that, to protect its swarm, the sacrificial millipede also applies a self-destructive defense strategy-the endogenous rupturing of the defensive sacs to mix ChuaMOX and mandelonitrile at an optimum pH. Further study of defensive systems in primitive arthropods will pave the way to elucidate the evolution of altruistic defenses in the animal kingdom.

  5. A sacrificial millipede altruistically protects its swarm using a drone blood enzyme, mandelonitrile oxidase.

    PubMed

    Ishida, Yuko; Kuwahara, Yasumasa; Dadashipour, Mohammad; Ina, Atsutoshi; Yamaguchi, Takuya; Morita, Masashi; Ichiki, Yayoi; Asano, Yasuhisa

    2016-01-01

    Soldiers of some eusocial insects exhibit an altruistic self-destructive defense behavior in emergency situations when attacked by large enemies. The swarm-forming invasive millipede, Chamberlinius hualienensis, which is not classified as eusocial animal, exudes irritant chemicals such as benzoyl cyanide as a defensive secretion. Although it has been thought that this defensive chemical was converted from mandelonitrile, identification of the biocatalyst has remained unidentified for 40 years. Here, we identify the novel blood enzyme, mandelonitrile oxidase (ChuaMOX), which stoichiometrically catalyzes oxygen consumption and synthesis of benzoyl cyanide and hydrogen peroxide from mandelonitrile. Interestingly the enzymatic activity is suppressed at a blood pH of 7, and the enzyme is segregated by membranes of defensive sacs from mandelonitrile which has a pH of 4.6, the optimum pH for ChuaMOX activity. In addition, strong body muscle contractions are necessary for de novo synthesis of benzoyl cyanide. We propose that, to protect its swarm, the sacrificial millipede also applies a self-destructive defense strategy-the endogenous rupturing of the defensive sacs to mix ChuaMOX and mandelonitrile at an optimum pH. Further study of defensive systems in primitive arthropods will pave the way to elucidate the evolution of altruistic defenses in the animal kingdom. PMID:27265180

  6. Selection of evodiamine as a novel topoisomerase I inhibitor by structure-based virtual screening and hit optimization of evodiamine derivatives as antitumor agents.

    PubMed

    Dong, Guoqiang; Sheng, Chunquan; Wang, Shengzheng; Miao, Zhenyuan; Yao, Jianzhong; Zhang, Wannian

    2010-11-11

    Human topoisomerase I (TopoI) is recognized as a valuable target for the development of effective antitumor agents. Structure-based virtual screening was applied to the discovery of structurally diverse TopoI inhibitors. From 23 compounds selected by virtual screening, a total of 14 compounds were found to be TopoI inhibitors. Five hits (compounds 1, 14, 20, 21, and 23) also showed moderate to good in vitro antitumor activity. These novel structures can be considered as good starting points for the development of new antitumor lead compounds. Hit 20 (evodiamine) was chosen for preliminary structure-activity relationship studies. Various groups, including alkyl, benzoyl, benzyl and ester, were introduced to the indole nitrogen atom of evodiamine. The substituted benzoyl groups were found to be favorable for the antitumor activity and spectrum. The 4-Cl benzoyl derivative, compound 29u, was the most active one with IC(50) values in the range 0.049-2.6 μM.

  7. Docking Simulation of the Binding Interactions of Saxitoxin Analogs Produced by the Marine Dinoflagellate Gymnodinium catenatum to the Voltage-Gated Sodium Channel Nav1.4.

    PubMed

    Durán-Riveroll, Lorena M; Cembella, Allan D; Band-Schmidt, Christine J; Bustillos-Guzmán, José J; Correa-Basurto, José

    2016-05-06

    Saxitoxin (STX) and its analogs are paralytic alkaloid neurotoxins that block the voltage-gated sodium channel pore (Nav), impeding passage of Na⁺ ions into the intracellular space, and thereby preventing the action potential in the peripheral nervous system and skeletal muscle. The marine dinoflagellate Gymnodinium catenatum produces an array of such toxins, including the recently discovered benzoyl analogs, for which the mammalian toxicities are essentially unknown. We subjected STX and its analogs to a theoretical docking simulation based upon two alternative tri-dimensional models of the Nav1.4 to find a relationship between the binding properties and the known mammalian toxicity of selected STX analogs. We inferred hypothetical toxicities for the benzoyl analogs from the modeled values. We demonstrate that these toxins exhibit different binding modes with similar free binding energies and that these alternative binding modes are equally probable. We propose that the principal binding that governs ligand recognition is mediated by electrostatic interactions. Our simulation constitutes the first in silico modeling study on benzoyl-type paralytic toxins and provides an approach towards a better understanding of the mode of action of STX and its analogs.

  8. Docking Simulation of the Binding Interactions of Saxitoxin Analogs Produced by the Marine Dinoflagellate Gymnodinium catenatum to the Voltage-Gated Sodium Channel Nav1.4.

    PubMed

    Durán-Riveroll, Lorena M; Cembella, Allan D; Band-Schmidt, Christine J; Bustillos-Guzmán, José J; Correa-Basurto, José

    2016-01-01

    Saxitoxin (STX) and its analogs are paralytic alkaloid neurotoxins that block the voltage-gated sodium channel pore (Nav), impeding passage of Na⁺ ions into the intracellular space, and thereby preventing the action potential in the peripheral nervous system and skeletal muscle. The marine dinoflagellate Gymnodinium catenatum produces an array of such toxins, including the recently discovered benzoyl analogs, for which the mammalian toxicities are essentially unknown. We subjected STX and its analogs to a theoretical docking simulation based upon two alternative tri-dimensional models of the Nav1.4 to find a relationship between the binding properties and the known mammalian toxicity of selected STX analogs. We inferred hypothetical toxicities for the benzoyl analogs from the modeled values. We demonstrate that these toxins exhibit different binding modes with similar free binding energies and that these alternative binding modes are equally probable. We propose that the principal binding that governs ligand recognition is mediated by electrostatic interactions. Our simulation constitutes the first in silico modeling study on benzoyl-type paralytic toxins and provides an approach towards a better understanding of the mode of action of STX and its analogs. PMID:27164145

  9. ATR-FTIR spectroscopy study of the photodegradation protective properties of BP-4 and 4HBP in polyvinyl acetate thin films

    NASA Astrophysics Data System (ADS)

    Bubev, Emil; Georgiev, Anton; Machkova, Maria

    2016-08-01

    In this paper the protective properties of 4HBP (4-hydroxybenzophenone) and BP-4 (5-benzoyl-2-hydroxy-4-methoxybenzenesulfonic acid) in polyvinyl acetate thin films have been studied. UV-irradiation on the films was applied in real humidity and inert atmosphere for 1, 2 and 4 h accelerated weathering. ATR-FTIR and UV-VIS spectroscopies have been used for qualitative and quantitative estimation of photodepletion of the UV-absorbers and photostability of polyvinyl acetate films. Both UV-absorbers have demonstrated good protective properties in inert atmosphere compared to real humidity. The mechanisms of photochemical reactions of 4HBP (4-hydroxybenzophenone) and BP-4 (5-benzoyl-2-hydroxy-4-methoxybenzenesulfonic acid) were attributed to photoenolization of carbonyl and hydroxyl groups. The experimental results demonstrated that 4HBP (4-hydroxybenzophenone) has higher protective properties than BP-4 (5-benzoyl-2-hydroxy-4-methoxybenzenesulfonic acid). The photodegradation mechanisms of polyvinyl acetate films in inert atmosphere and real humidity were assigned based on the Norrish type I and II reactions.

  10. Systematic review of antibiotic resistance in acne: an increasing topical and oral threat.

    PubMed

    Walsh, Timothy R; Efthimiou, John; Dréno, Brigitte

    2016-03-01

    Topical and oral antibiotics are routinely used to treat acne. However, antibiotic resistance is increasing, with many countries reporting that more than 50% of Propionibacterium acnes strains are resistant to topical macrolides, making them less effective. We reviewed the current scientific literature to enable proposal of recommendations for antibiotic use in acne treatment. References were identified through PubMed searches for articles published from January, 1954, to March 7, 2015, using four multiword searches. Ideally, benzoyl peroxide in combination with a topical retinoid should be used instead of a topical antibiotic to minimise the impact of resistance. Oral antibiotics still have a role in the treatment of moderate-to-severe acne, but only with a topical retinoid, benzoyl peroxide, or their combination, and ideally for no longer than 3 months. To limit resistance, it is recommended that benzoyl peroxide should always be added when long-term oral antibiotic use is deemed necessary. The benefit-to-risk ratio of long-term antibiotic use should be carefully considered and, in particular, use alone avoided where possible. There is a need to treat acne with effective alternatives to antibiotics to reduce the likelihood of resistance.

  11. Persistent and heritable structural damage induced in heterochromatic DNA from rat liver by N-nitrosodimethylamine

    SciTech Connect

    Ward, E.J.; Stewart, B.W.

    1987-03-24

    Analysis, by benzoylated DEAE-cellulose chromatography, has been made of structural change in eu- and heterochromatic DNA from rat liver following administration of the carcinogen N-nitrosodimethylamine. Either hepatic DNA was prelabeled with (/sup 3/H)thymidine administered 2-3 weeks before injection of the carcinogen or the labeled precursor was given during regenerative hyperplasia in rats treated earlier with N-nitrosodimethylamine. Following phenol extraction of either whole liver homogenate or nuclease-fractionated eu- and heterochromatin, carcinogen-modified DNA was examined by stepwise or caffeine gradient elution from benzoylated DEAE-cellulose. In whole DNA, nitrosamine-induced single-stranded character was maximal 4-24 h after treatment, declining rapidly thereafter; gradient elution of these DNA preparations also provided short-term evidence of structural change. Caffeine gradient chromatography suggested short-term nitrosamine-induced structural change in euchromatic DNA, while increased binding of heterochromatic DNA was evident for up to 3 months after carcinogen treatment. Preparations of newly synthesized heterochromatic DNA from animals subjected to hepatectomy up to 2 months after carcinogen treatment provided evidence of heritable structural damage. Carcinogen-induced binding of heterochromatic DNA to benzoylated DEAE-cellulose was indicative of specific structural lesions whose affinity equalled that of single-stranded DNA up to 1.0 kilobase in length. The data suggest that structural lesions in heterochromatin, which may be a consequence of incomplete repair, are preferentially degraded by endogenous nuclease(s).

  12. Identification and characterization of 2-naphthoyl-coenzyme A reductase, the prototype of a novel class of dearomatizing reductases.

    PubMed

    Eberlein, Christian; Estelmann, Sebastian; Seifert, Jana; von Bergen, Martin; Müller, Michael; Meckenstock, Rainer U; Boll, Matthias

    2013-06-01

    The enzymatic dearomatization of aromatic ring systems by reduction represents a highly challenging redox reaction in biology and plays a key role in the degradation of aromatic compounds under anoxic conditions. In anaerobic bacteria, most monocyclic aromatic growth substrates are converted to benzoyl-coenzyme A (CoA), which is then dearomatized to a conjugated dienoyl-CoA by ATP-dependent or -independent benzoyl-CoA reductases. It was unresolved whether or not related enzymes are involved in the anaerobic degradation of environmentally relevant polycyclic aromatic hydrocarbons (PAHs). In this work, a previously unknown dearomatizing 2-naphthoyl-CoA reductase was purified from extracts of the naphthalene-degrading, sulphidogenic enrichment culture N47. The oxygen-tolerant enzyme dearomatized the non-activated ring of 2-naphthoyl-CoA by a four-electron reduction to 5,6,7,8-tetrahydro-2-naphthoyl-CoA. The dimeric 150 kDa enzyme complex was composed of a 72 kDa subunit showing sequence similarity to members of the flavin-containing 'old yellow enzyme' family. NCR contained FAD, FMN, and an iron-sulphur cluster as cofactors. Extracts of Escherichia coli expressing the encoding gene catalysed 2-naphthoyl-CoA reduction. The identified NCR is a prototypical enzyme of a previously unknown class of dearomatizing arylcarboxyl-CoA reductases that are involved in anaerobic PAH degradation; it fundamentally differs from known benzoyl-CoA reductases.

  13. Moisturizers for Acne

    PubMed Central

    Chularojanamontri, Leena; Tuchinda, Papapit; Kulthanan, Kanokvalai

    2014-01-01

    Acne is a chronic inflammatory disease of the pilosebaceous unit that affects almost all teenagers. Different treatments offer different modes of action, but aim to target acne pathology. Topical therapies, such as benzoyl peroxide, retinoids, antibiotics with alcohol-based preparations, and salicylic acid, can cause skin irritation resulting in a lack of patient adherence. Some physicians recommend patients use moisturizers as adjunctive treatment of acne, especially when either topical benzoyl peroxide or a retinoid is prescribed. Furthermore, some evidence shows that moisturizers can contribute independently to improve signs and symptoms of acne. Moisturizers contain three main properties, which are occlusive, humectant, and emollient effects. Currently, many moisturizers claim to be suitable for acne treatment. This article aims to provide a review of the active ingredients and properties of those moisturizers. Fifty-two moisturizers for acne were included for analysis. Most of the products (92%) have anti-inflammatory properties apart from occlusive, humectant, and emollient effects. Anti-acne medications, including salicylic acid, benzoyl peroxide, and retinol, were found respectively in 35, 10, and 8 percent of the moisturizer products containing anti-inflammatory properties. More than half of the products contain dimethicone and/or glycerin for its moisturizer property. Aloe vera and witch hazel are botanical anti-inflammatories that were commonly found in this study. Scientific data regarding some ingredients are discussed to provide a guide for physicians in selecting moisturizers for acne patients. PMID:24847408

  14. A sacrificial millipede altruistically protects its swarm using a drone blood enzyme, mandelonitrile oxidase

    PubMed Central

    Ishida, Yuko; Kuwahara, Yasumasa; Dadashipour, Mohammad; Ina, Atsutoshi; Yamaguchi, Takuya; Morita, Masashi; Ichiki, Yayoi; Asano, Yasuhisa

    2016-01-01

    Soldiers of some eusocial insects exhibit an altruistic self-destructive defense behavior in emergency situations when attacked by large enemies. The swarm-forming invasive millipede, Chamberlinius hualienensis, which is not classified as eusocial animal, exudes irritant chemicals such as benzoyl cyanide as a defensive secretion. Although it has been thought that this defensive chemical was converted from mandelonitrile, identification of the biocatalyst has remained unidentified for 40 years. Here, we identify the novel blood enzyme, mandelonitrile oxidase (ChuaMOX), which stoichiometrically catalyzes oxygen consumption and synthesis of benzoyl cyanide and hydrogen peroxide from mandelonitrile. Interestingly the enzymatic activity is suppressed at a blood pH of 7, and the enzyme is segregated by membranes of defensive sacs from mandelonitrile which has a pH of 4.6, the optimum pH for ChuaMOX activity. In addition, strong body muscle contractions are necessary for de novo synthesis of benzoyl cyanide. We propose that, to protect its swarm, the sacrificial millipede also applies a self-destructive defense strategy—the endogenous rupturing of the defensive sacs to mix ChuaMOX and mandelonitrile at an optimum pH. Further study of defensive systems in primitive arthropods will pave the way to elucidate the evolution of altruistic defenses in the animal kingdom. PMID:27265180

  15. Investigation the degradation and devulcanization reaction of thermoplastic vulcanizate using peroxide compound

    NASA Astrophysics Data System (ADS)

    Temram, Chokkanit; Wattanakul, Karnthidaporn

    2012-09-01

    Investigation the Degradation and Devulcanization Reaction of Thermoplastic Vulcanizate using Peroxide Compound was carried out by means of benzoyl peroxide as a devulcanizing agent. The temperature for the recycling condition was gradually increased from 80°C to 190°C because of the half-life of benzoyl peroxide. Furthermore, the effects of time and concentration of devulcanizing agent on the recycling process were investigated. The extent of devulcanization of thermoplastic vulcanizate was studied by estimation of percent devulcanization, gel fraction of rubber after swelling and crosslink density. According to the results, we found that the crosslink density of devulcanized thermoplastic vulcanizate was 29.37% less than virgin thermoplastic vulcanizate by adding benzoyl peroxide for 1 phr. This result is correspondence to the decreasing in gel fraction of devulcanized thermoplastic vulcanizate. Moreover, the addition of 5 phr and 10 phr to TPVs result to the significant decrement in crosslink density about 64%. The effect of temperature for devulcanization was also investigated to obtain the optimum conditions. The result shows that the percentage of devulcanization was slightly increased as the increasing in the starting temperature from 80°C to 105°C.

  16. Systematic review of antibiotic resistance in acne: an increasing topical and oral threat.

    PubMed

    Walsh, Timothy R; Efthimiou, John; Dréno, Brigitte

    2016-03-01

    Topical and oral antibiotics are routinely used to treat acne. However, antibiotic resistance is increasing, with many countries reporting that more than 50% of Propionibacterium acnes strains are resistant to topical macrolides, making them less effective. We reviewed the current scientific literature to enable proposal of recommendations for antibiotic use in acne treatment. References were identified through PubMed searches for articles published from January, 1954, to March 7, 2015, using four multiword searches. Ideally, benzoyl peroxide in combination with a topical retinoid should be used instead of a topical antibiotic to minimise the impact of resistance. Oral antibiotics still have a role in the treatment of moderate-to-severe acne, but only with a topical retinoid, benzoyl peroxide, or their combination, and ideally for no longer than 3 months. To limit resistance, it is recommended that benzoyl peroxide should always be added when long-term oral antibiotic use is deemed necessary. The benefit-to-risk ratio of long-term antibiotic use should be carefully considered and, in particular, use alone avoided where possible. There is a need to treat acne with effective alternatives to antibiotics to reduce the likelihood of resistance. PMID:26852728

  17. Determination of Carboxypeptidase Activity in Clinical Pathogens by Gas Chromatography–Mass Spectrometry

    PubMed Central

    Lough, Fraser; Perry, John D.; Stanforth, Stephen P.; Dean, John R.

    2016-01-01

    ABSTRACT A novel method for the determination of benzoic acid has been employed to identify carboxypeptidase activities in clinically relevant pathogens. Benzoic acid was determined after chemical derivatization by gas chromatography–mass spectrometry (GC–MS). N-Benzoyl amino acid substrates were evaluated for the detection of carboxypeptidase activities in a number of clinical pathogens. Upon enzymatic hydrolysis of these substrates, benzoic acid was produced which was detected by extraction from the liquid culture supernatant, derivatization as the trimethylsilyl ester, with subsequent analysis by GC–MS. Enzymatic hydrolysis of N-benzoyl glycine was observed for S. agalactiae, M. morganii, and A. baumannii. In addition, P. fluorescens was found to hydrolyze N-benzoyl-L-glutamic acid. Although the method provides an alternative approach for determining carboxypeptidase activity, ultimately it would not be a suitable method in a clinical setting. However, the method is well-suited for identifying carboxypeptidase activities that have not been previously described or to corroborate a carboxypeptidase assay with the ninhydrin reagent. PMID:27226648

  18. Genotoxicity of dental resin polymerization initiators in vitro.

    PubMed

    Nomura, Y; Teshima, W; Kawahara, T; Tanaka, N; Ishibashi, H; Okazaki, M; Arizono, K

    2006-01-01

    The polymerization initiators for resins cured using visible light usually consist of a photosensitizer, primarily camphorquinone (CQ), and a reducing agent, which is often a tertiary amine (DMPT, DMAEMA), while the initiator used for self-curing resins consists of benzoyl peroxide (BPO) and a tertiary amine (DMPT). The genotoxicities of camphorquinone (CQ), benzoyl peroxide (BPO), dimethyl-para-toluidine (DMPT), 2-dimethylamino-ethyl-methacrylate (DMAEMA), and 1-allyl-2-thiourea (ATU) were examined using the bioluminescent bacterial genotoxicity test. 4-Nitroquinoline-N-oxide (4NQO) was prepared for comparison with these chemicals. Acetone solutions of the five polymerization initiators and 4NQO were prepared. Benzoyl peroxide (BPO), dimethyl-para-toluidine (DMPT), and 1-allyl-2-thiourea (ATU) showed significant genotoxic activity at 24 h in the bioluminescent bacterial genotoxicity test, at concentrations of approximately 5 microM, 4 mM, and 1 mM, respectively. 2-Dimethyloamino-ethyl-methacrylate (DMAEMA) did not have genotoxic activity and CQ had questionable genotoxic activity. In comparison, 4NQO had strong genotoxicity, at 4 microM, roughly the same as that of BPO. Therefore, BPO should be used carefully in clinical dentistry.

  19. Treatment of Acne in Pregnancy.

    PubMed

    Chien, Anna L; Qi, Ji; Rainer, Barbara; Sachs, Dana L; Helfrich, Yolanda R

    2016-01-01

    Acne vulgaris is a common disease of the pilosebaceous unit and affects adolescents and adults. Because high-quality guidelines regarding treatment of acne in pregnancy are scarce, management of this condition can be challenging. We describe the safety profile of common therapies and outline approaches based on available evidence. Topical azelaic acid or benzoyl peroxide can be recommended as baseline therapy. A combination of topical erythromycin or clindamycin with benzoyl peroxide is recommended for inflammatory acne. Oral erythromycin or cephalexin is generally considered safe for moderate to severe inflammatory acne when used for a few weeks. A short course of oral prednisolone may be useful for treating fulminant nodular cystic acne after the first trimester. In general, topical and oral antibiotics should not be used as monotherapy, but combined with topical benzoyl peroxide to decrease bacterial resistance. Oral retinoids are teratogenic and absolutely contraindicated for women who are pregnant or considering pregnancy. Although some complementary therapies including micronutrients and nonpharmacologic treatments seem to be well tolerated, limited data exist regarding their safety and efficacy, and they are not currently recommended during pregnancy. The risk-to-benefit ratio, efficacy, acceptability, and costs are considerations when choosing a treatment for acne in pregnancy. PMID:26957383

  20. Breakup of evaporating/burning slurry drops by additives

    NASA Astrophysics Data System (ADS)

    Choudhury, P. Roy; Gerstein, M.

    Single drops of silicon carbide-cumene slurry were suspended from a quartz fiber and ignited. An inert material such as silicon carbide was chosen so that the droplets can be burned until all the fuel is consumed and only the inert residue is left on the quartz fiber. Benzoyl peroxide was added to cumene and the time to disruption of the liquid drop was measured. In the case of benzoyl peroxide, the breaking up of the drop resulting from its thermal decomposition produced CO 2. Both the drop disruption time and the burning of the slurry to dryness were predicted theoretically. Radiation absorption was found to be an important factor in the case of the slurry. Benzoyl peroxide and carbamide peroxide were investigated as additives to a boron slurry to determine if effective drop break-up could be achieved. Both additives produced drop shattering. The carbamide peroxide was particularly effective due to the production of O 2. The green flame associated with boron burning was clearly evident.

  1. Docking Simulation of the Binding Interactions of Saxitoxin Analogs Produced by the Marine Dinoflagellate Gymnodinium catenatum to the Voltage-Gated Sodium Channel Nav1.4

    PubMed Central

    Durán-Riveroll, Lorena M.; Cembella, Allan D.; Band-Schmidt, Christine J.; Bustillos-Guzmán, José J.; Correa-Basurto, José

    2016-01-01

    Saxitoxin (STX) and its analogs are paralytic alkaloid neurotoxins that block the voltage-gated sodium channel pore (Nav), impeding passage of Na+ ions into the intracellular space, and thereby preventing the action potential in the peripheral nervous system and skeletal muscle. The marine dinoflagellate Gymnodinium catenatum produces an array of such toxins, including the recently discovered benzoyl analogs, for which the mammalian toxicities are essentially unknown. We subjected STX and its analogs to a theoretical docking simulation based upon two alternative tri-dimensional models of the Nav1.4 to find a relationship between the binding properties and the known mammalian toxicity of selected STX analogs. We inferred hypothetical toxicities for the benzoyl analogs from the modeled values. We demonstrate that these toxins exhibit different binding modes with similar free binding energies and that these alternative binding modes are equally probable. We propose that the principal binding that governs ligand recognition is mediated by electrostatic interactions. Our simulation constitutes the first in silico modeling study on benzoyl-type paralytic toxins and provides an approach towards a better understanding of the mode of action of STX and its analogs. PMID:27164145

  2. S1 subsite specificity of a recombinant cysteine proteinase, CPB, of Leishmania mexicana compared with cruzain, human cathepsin L and papain using substrates containing non-natural basic amino acids.

    PubMed

    Alves, L C; Melo, R L; Sanderson, S J; Mottram, J C; Coombs, G H; Caliendo, G; Santagada, V; Juliano, L; Juliano, M A

    2001-03-01

    We have explored the substrate specificity of a recombinant cysteine proteinase of Leishmania mexicana (CPB2.8 Delta CTE) in order to obtain data that will enable us to design specific inhibitors of the enzyme. Previously we have shown that the enzyme has high activity towards substrates with a basic group at the P1 position [Hilaire, P.M.S., Alves, L.C., Sanderson, S.J., Mottram, J.C., Juliano, M.A., Juliano, L., Coombs, G.H. & Meldal M. (2000) Chem. Biochem. 1, 115--122], but we have also observed high affinity for peptides with hydrophobic residues at this position. In order to have substrates containing both features, we synthesized one series of internally quenched fluorogenic peptides derived from the sequence ortho-amino-benzoyl-FRSRQ-N-[2,4-dinitrophenyl]-ethylenediamine, and substituted the Arg at the P1 position with the following non-natural basic amino acids: 4-aminomethyl-phenylalanine (Amf), 4-guanidine-phenylalanine (Gnf), 4-aminomethyl-N-isopropyl-phenylalanine (Iaf), 3-pyridyl-alanine (Pya), 4-piperidinyl-alanine (Ppa), 4-aminomethyl-cyclohexyl-alanine (Ama), and 4-aminocyclohexyl-alanine (Aca). For comparison, the series derived from ortho-amino-benzoyl-FRSRQ-N-[2,4-dinitrophenyl]-ethylenediamine was also assayed with cruzain (the major cysteine proteinase of Trypanosoma cruzi), human cathepsin L and papain. The peptides ortho-amino-benzoyl-FAmfSRQ-N-[2,4-dinitrophenyl]-ethylenediamine (k(cat)/K(m) = 12,000 mM(-1) x s(-1)) and ortho-amino-benzoyl-FIafSRQ-N-[2,4-dinitrophenyl]-ethylenediamine (k(cat)/K(m) = 27,000 mM(-1) x s(-1)) were the best substrates for CPB2.8 Delta CTE. In contrast, ortho-amino-benzoyl-FAmaSRQ-N-[2,4-dinitrophenyl]-ethylenediamine and ortho-amino-benzoyl-FAcaSRQ-N-[2,4-dinitrophenyl]-ethylenediamine were very resistant and inhibited this enzyme with K(i) values of 23 nM and 30 nM, respectively. Cruzain hydrolyzed quite well the substrates in this series with Amf, Ppa and Aca, whereas the peptide with Ama was resistant and

  3. Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants.

    PubMed

    Fait, M Elisa; Garrote, Graciela L; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; Morcelle, Susana R

    2015-07-01

    Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N (α)-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N (α)-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N (α)-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations. PMID:25894891

  4. Prophylactic efficacy of four antibacterial shampoos against Staphylococcus intermedius in dogs.

    PubMed

    Kwochka, K W; Kowalski, J J

    1991-01-01

    Prophylactic efficacy of 4 antibacterial shampoos against Staphylococcus intermedius in dogs was determined by use of a controlled quantitative technique. Ten adult Beagles were used in the study. The antibacterial agents in the shampoos were 3.0% benzoyl peroxide, 0.5% chlorhexidine acetate, 1.0% available iodine as a polyalkyleneglycol-iodine complex, and a combination of 0.5% triclosan, 2.0% sulfur, and 2.0% salicylic acid. Treated and control sites were challenge exposed with 5.30 +/- 0.10 (log10) S intermedius colony-forming units (CFU)/cm2 of skin and occluded for 5 hours. At the end of the test period, remaining bacteria were removed with a detergent cup-scrub technique and the total number of S intermedius CFU/cm2 skin was calculated for each treated and control site. Nontreated bacteria-challenged control sites yielded 5.62 +/- 0.65 S intermedius CFU/cm2 of skin. Staphylococcus intermedius recovery (CFU/cm2) from the treated sites was 0.94 +/- 0.76 for benzoyl peroxide, 1.96 +/- 1.33 for chlorhexidine acetate, 3.11 +/- 0.48 for organic iodine, and 4.69 +/- 0.23 for triclosan-sulfur-salicylic acid. Each S intermedius recovery value from the 4 treated sites was significantly (P less than 0.05) lower than that from the nontreated S intermedius challenge-exposed control site. Bacteria recovery values were also significantly (P less than 0.05) different among the 4 shampoo-treated sites. We concluded that all shampoos had significant (P less than 0.05) prophylactic activity against S intermedius over 5 hours. The shampoo containing benzoyl peroxide was determined to have the greatest efficacy among the products tested.

  5. Purification and characterization of an extracellular trypsin-like protease of Fusarium oxysporum var. lini.

    PubMed

    Barata, Ricardo Andrade; Andrade, Milton Hercules Guerra; Rodrigues, Roberta Dias; Castro, Ieso Miranda

    2002-01-01

    An alkaline serineprotease, capable of hydrolyzing Nalpha-benzoyl- dl arginine p-nitroanilide, was secreted by Fusarium oxysporum var. lini grown in the presence of gelatin as the sole nitrogen and carbon source. The protease was purified 65-fold to electrophoretic homogenity from the culture supernatant in a three-step procedure comprising QSepharose chromatography, affinity chromatography, and FPLC on a MonoQ column. SDS-PAGE analysis of the purified protein indicated an estimated molecular mass of 41 kDa. The protease had optimum activity at a reaction temperature of 45 degrees C and showed a rapid decrease of activity at 48 degrees C. The optimum pH was around 8.0. Characterization of the protease showed that Ca2+ and Mg2+ cations increased the activity, which was not inhibited by EDTA or 1,10-phenanthroline. The enzyme activity on Nalpha-benzoyl-DL arginine p-nitroanilide was inhibited by 4-(2-aminoethyl)-benzenesulfonyl fluoride hydrochloride, p-aminobenzamidine dihydrochloride, aprotinin, 3-4 dichloroisocoumarin, and N-tosyl-L-lysine chloromethyl ketone. The enzyme is also inhibited by substrate concentrations higher than 2.5 x 10(-4)M. The protease had a Michaelis-Menten constant of 0.16 mM and a V(max) of 0.60 mumol released product.min(-1).mg(-1) enzyme when assayed in a non-inhibiting substrate concentration. The activity on Nalpha-benzoyl- dl arginine p-nitroanilide was competitively inhibited by p-aminobenzamidine dihydrochoride. A K(i) value of 0.04 mM was obtained.

  6. An Efficient High-performance Liquid Chromatography Combined with Electrospray Ionization Tandem Mass Spectrometry Method to Elaborate the Changes of Components Between the Raw and Processed Radix Aconitum kusnezoffii

    PubMed Central

    Wang, Beibei; Ji, Jiaojiao; Zhao, Shuang; Dong, Jie; Tan, Peng; Na, Shengsang; Liu, Yonggang

    2016-01-01

    Background: Crude radix Aconitum kusnezoffii (RAK) has great toxicity. Traditional Chinese medicine practice proved that processing may decrease its toxicity. In our previous study, we had established a new method of RAK processing (Paozhi). However, the mechanism is yet not perfect. Objective: To explore the related mechanism of processing through comparing the chemical contents. Materials and Methods: A new processing method of RAK named stoving (Hong Zhi) was used. In particular, RAK was stored at 110°C for 8 h, and then high performance liquid chromatography combined with electrospray ionization tandem mass spectrometry (HPLC-ESI-MSn) was developed for the detection of the alkaloids of the crude and processed RAK decoction pieces. Results: Thirty components of the crude RAK were discovered, among which, 23 alkaloids were identified. Meanwhile, 23 ingredients were detected in the processed RAK decoction pieces, among which, 20 alkaloids were determined yet. By comparison, eight alkaloids were found in both crude and processed RAK decoction pieces, 15 alkaloids were not found in the crude RAK, however, 10 new constituents yield after processing, which are 10-OH-hypaconine, 10-OH-mesaconine, isomer of bullatine A, 14-benzoyl-10-OH-mesaconine, 14-benzoyl-10-OH-aconine, 14-benzoyl-10-OH-hypaconine, dehydrated aconitine, 14-benzoylaconine, chuanfumine, dehydrated mesaconitine. Conclusion: The present study showed that significant change of alkaloids was detected in RAK before and after processing. Among them, the highly toxic diester alkaloids decreased and the less toxic monoester alkaloids increased. Moreover, the concentration changes significantly. HPLC-ESI-MSn are Efficient to elaborate the mechanism of reduction of toxicity and enhancement efficacy after processing. SUMMARY Stoving is a simple and effective method for the processing of radix Aconitum kusnezoffii.In the positive mode, the characteristic fragmentations of Aconitum alkaloids were obtained

  7. Purification and characterization of an extracellular trypsin-like protease of Fusarium oxysporum var. lini.

    PubMed

    Barata, Ricardo Andrade; Andrade, Milton Hercules Guerra; Rodrigues, Roberta Dias; Castro, Ieso Miranda

    2002-01-01

    An alkaline serineprotease, capable of hydrolyzing Nalpha-benzoyl- dl arginine p-nitroanilide, was secreted by Fusarium oxysporum var. lini grown in the presence of gelatin as the sole nitrogen and carbon source. The protease was purified 65-fold to electrophoretic homogenity from the culture supernatant in a three-step procedure comprising QSepharose chromatography, affinity chromatography, and FPLC on a MonoQ column. SDS-PAGE analysis of the purified protein indicated an estimated molecular mass of 41 kDa. The protease had optimum activity at a reaction temperature of 45 degrees C and showed a rapid decrease of activity at 48 degrees C. The optimum pH was around 8.0. Characterization of the protease showed that Ca2+ and Mg2+ cations increased the activity, which was not inhibited by EDTA or 1,10-phenanthroline. The enzyme activity on Nalpha-benzoyl-DL arginine p-nitroanilide was inhibited by 4-(2-aminoethyl)-benzenesulfonyl fluoride hydrochloride, p-aminobenzamidine dihydrochloride, aprotinin, 3-4 dichloroisocoumarin, and N-tosyl-L-lysine chloromethyl ketone. The enzyme is also inhibited by substrate concentrations higher than 2.5 x 10(-4)M. The protease had a Michaelis-Menten constant of 0.16 mM and a V(max) of 0.60 mumol released product.min(-1).mg(-1) enzyme when assayed in a non-inhibiting substrate concentration. The activity on Nalpha-benzoyl- dl arginine p-nitroanilide was competitively inhibited by p-aminobenzamidine dihydrochoride. A K(i) value of 0.04 mM was obtained. PMID:16233307

  8. Biocatalytic synthesis, antimicrobial properties and toxicity studies of arginine derivative surfactants.

    PubMed

    Fait, M Elisa; Garrote, Graciela L; Clapés, Pere; Tanco, Sebastian; Lorenzo, Julia; Morcelle, Susana R

    2015-07-01

    Two novel arginine-based cationic surfactants were synthesized using as biocatalyst papain, an endopeptidase from Carica papaya latex, adsorbed onto polyamide. The classical substrate N (α)-benzoyl-arginine ethyl ester hydrochloride for the determination of cysteine and serine proteases activity was used as the arginine donor, whereas decyl- and dodecylamine were used as nucleophiles for the condensation reaction. Yields higher than 90 and 80 % were achieved for the synthesis of N (α)-benzoyl-arginine decyl amide (Bz-Arg-NHC10) and N (α)-benzoyl-arginine dodecyl amide (Bz-Arg-NHC12), respectively. The purification process was developed in order to make it more sustainable, by using water and ethanol as the main separation solvents in a single cationic exchange chromatographic separation step. Bz-Arg-NHC10 and Bz-Arg-NHC12 proved antimicrobial activity against both Gram-positive and Gram-negative bacteria, revealing their potential use as effective disinfectants as they reduced 99 % the initial bacterial population after only 1 h of contact. The cytotoxic effect towards different cell types of both arginine derivatives was also measured. Bz-Arg-NHCn demonstrated lower haemolytic activity and were less eye-irritating than the commercial cationic surfactant cetrimide. A similar trend could also be observed when cytotoxicity was tested on hepatocytes and fibroblast cell lines: both arginine derivatives were less toxic than cetrimide. All these properties would make the two novel arginine compounds a promising alternative to commercial cationic surfactants, especially for their use as additives in topical formulations.

  9. N-benzoylimido complexes of palladium. Synthesis, structural characterisation and structure-reactivity relationship.

    PubMed

    Besenyei, Gábor; Párkányi, László; Szalontai, Gábor; Holly, Sándor; Pápai, Imre; Keresztury, Gábor; Nagy, Andrea

    2004-07-01

    Benzoyl azides, ArC(O)N3, 2, (Ar = phenyl or substituted phenyl), react with [Pd2Cl2(dppm)2], 1, [dppm = bis(diphenylphosphino)methane] with the formation of novel [Pd2Cl2(mu-NC(O)Ar)(dppm)2], 3, benzoylnitrene complexes that were structurally characterised by multinuclear magnetic resonance and IR spectroscopy and, in several instances, by single crystal X-ray diffraction. As shown by crystallographic studies, the C2P4Pd2 rings adopt extended twist-boat conformations with methylene groups bending towards the bridging benzoylimido moieties. X-ray diffraction studies have revealed the chiral nature of the imido complexes, the chiral element being the propeller-like C2P4Pd2 ring. Structural data accumulated on complexes 3 such as short C-N distances (1.32 A), elongated C=O bonds (1.30 A) as well as the outstandingly high barrier to internal rotation around the N-C(O) linkage (88.3 kJ mol(-1)) are in line with extensive ppi-ppi interaction between the bridging nitrogen and the carbonyl carbon atoms. Theoretical calculations indicate an electron shift from the dimer towards the apical nitrogen atom, which, in turn, facilitates the donation of electrons towards the carbonyl moiety. To elucidate the structure-reactivity relationship of benzoyl azides towards 1, crystallographic and solution IR spectroscopic studies were carried out on a series of para-substituted benzoyl azides. The reaction obeys the Hammett equation. The large positive value of the reaction constant indicates that the azides act as electrophiles in the reaction studied. The enhanced reactivity of 2-nitrobenzoyl azide has been attributed to a decreased conjugation of the phenyl and carbonyl moieties in this reagent.

  10. Inhibition of 12-O-tetradecanoylphorbol-13-acetate and other skin tumor-promoter-caused induction of epidermal interleukin-1 alpha mRNA and protein expression in SENCAR mice by green tea polyphenols.

    PubMed

    Katiyar, S K; Rupp, C O; Korman, N J; Agarwal, R; Mukhtar, H

    1995-09-01

    Recent studies have shown that topical application of the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA) to murine skin results in increased expression of the highly inflammatory cytokine interleukin (IL)-1 alpha in the epidermis. This has led to the suggestion that IL-1 alpha directly or indirectly mediates the inflammatory and hyperplastic responses elicited by TPA and possibly by other skin tumor promoters. In the current study, we investigated the effect of skin application of a polyphenolic fraction isolated from green tea (GTP) to SENCAR mice on skin tumor-promoter-caused induction of cutaneous edema and hyperplasia, and IL-1 alpha mRNA expression. Pretreatment of the skin with GTP 30 min before that of anthralin, benzoyl peroxide, mezerein, and TPA resulted in a significant (p < 0.05) inhibition of cutaneous edema and epidermal hyperplasia caused by each of these tumor promoters. Northern blot analysis indicated that topical application of TPA, anthralin, mezerein, or benzoyl peroxide to SENCAR mice resulted in an increased expression of epidermal IL-1 alpha mRNA. Pretreatment of the skin with GTP or individual epicatechin derivatives (ECDs) present therein, 30 min before that of TPA, resulted in a significant inhibition of enhanced expression of epidermal IL-1 alpha mRNA caused by skin application of TPA. These inhibitory effects were found to be dependent on the dose of GTP. Among four epicatechin derivatives present in GTP, (-)-epicatechin-3-gallate and (-)-epigallocatechin-3-gallate were more effective than (-)-epigallocatechin and (-)-epicatechin in affording this inhibition. Preapplication of GTP was also found to afford inhibition against anthralin-, benzoyl peroxide-, and mezerein-caused increased expression of epidermal IL-1 alpha mRNA and protein. Our study suggests that the inhibition of tumor-promoter-induced IL-1 alpha mRNA and protein expression in mouse epidermis by green tea in combination with other inhibitory effects may be

  11. Peptidohydrolases of Soybean Root Nodules 12

    PubMed Central

    Malik, Nasir S. A.; Pfeiffer, N. E.; Williams, D. R.; Wagner, Fred W.

    1981-01-01

    Nodule extracts prepared from Glycine max var Woodworth possessed endopeptidase, aminopeptidase, and carboxypeptidase activities. Three distinct endopeptidase activities could be resolved by disc-gel electrophoresis at pH 8.8. According to their order of increasing electrophoretic mobility, the first of these enzymes hydrolyzed azocasein and n-benzoyl-l-Leu-β-naphthylamide, while the second hydrolyzed n-benzoyl-l-Arg-β-naphthylamine (Bz-l-Arg-βNA), n-benzoyl-l-Arg-p-nitroanilide (Bz-l-Arg-pNA), and azocasein. The third endopeptidase hydrolyzed Bz-l-Arg-βNA, Bz-l-Arg-pNA, and hemoglobin. Fractions of these enzymes extracted from electrophoresis gels were shown to have pH optima from 7.5 to 9.8. All of the endopeptidases were completely inhibited by diisopropylphosphorofluoridate, demonstrating that they were serine proteases. Aminopeptidase activity was measured using amino acyl-β-naphthylamides. Electrophoresis of nodule extracts at pH 6.8 resolved the aminopeptidase activity of nodule extracts into at least four fractions based on mobility and on activities toward amino acyl-β-naphthylamides. The major activity of two of the aminopeptidases was directed toward l-Leu- and l-Met-β-naphthylamide, while the other two aminopeptidases exhibited broader specificity and were capable of hydrolyzing a large number of amino acyl-β-naphthylamides. Two of the aminopeptidases extracted from electrophoresis gels were classified as thiol type enzymes, and all four aminopeptidases had neutral to basic pH optima. Images PMID:16661922

  12. Synthesis of 4,6-dideoxysucrose, and inhibition studies of Leuconostoc and Streptococcus D-glucansucrases with deoxy and chloro derivatives of sucrose modified at carbon atoms 3, 4, and 6.

    PubMed

    Tanriseven, A; Robyt, J F

    1989-02-15

    Starting from sucrose, 2,3,1',3',4',6'-hexa-O-benzoyl-6-deoxy-6-iodosucrose (1) was synthesized. Reaction of 1 with sulfuryl chloride in pyridine gave 2,3,1',3',4',6'-hexa-O-benzoyl-4-chloro-4,6-dideoxy-6-iodogalactosucr ose (2). Compound 2 was treated with tributyltin hydride in toluene in the presence of a radical initiator, alpha, alpha-azobis(isobutanonitrile) (AIBN), to remove iodine and chlorine groups and give hexa-O-benzoyl-4,6-dideoxysucrose. Benzoyl groups were removed by sodium methoxide in methanol to give 4,6-dideoxysucrose. Sucrose was modified at carbon atom 3, carbon atom 4, or carbon atoms 4 and 6, and these analogs were tested as inhibitors of the D-glucansucrases (D-glucosyltransferases) of Streptococcus mutans 6715 and Leuconostoc mesenteroides B-512F. Sucrose analogs used in this study are 4-deoxysucrose and 4-chloro-4-deoxygalactosucrose with S. mutans 6715 D-glucansucrases (GTF-S and GTF-I), and 3-deoxysucrose, 4-deoxysucrose, 4-chloro-4-deoxygalactosucrose, 6-deoxysucrose, and 4,6-dideoxysucrose with L. mesenteroides B-512F D-glucansucrase. The data indicate that 3-deoxysucrose, 4-deoxysucrose, and 4-chloro-4-deoxygalactosucrose are weak noncompetitive inhibitors for B-512F dextransucrase, with Ki values of 530, 201, and 202mM respectively. For the same enzyme, 6-deoxysucrose was a strong competitive inhibitor, with Ki of 1.60mM, and 4,6-dideoxysucrose was a good competitive inhibitor, with Ki of 20.3mM. 4-Deoxysucrose was a weak noncompetitive inhibitor for both GTF-I and GTF-S, with Ki values of 672 and 608mM, respectively. 4-Chloro-4-deoxygalactosucrose was also a weak noncompetitive inhibitor for GTF-I and GTF-S with Ki values of 391 and 308mM, respectively.(ABSTRACT TRUNCATED AT 250 WORDS) PMID:2524254

  13. Extraction and atomic absorption determination of molybdenumusing n-benzoylphenylhydroxylamine

    SciTech Connect

    Pilipenko, A.T.; Samchuk, A.I.; Wl' figarov, O.S.

    1985-05-01

    Tis paper studies the conditions of extraction of molybdenumby N-benzoyl-phenylhydroxylamine (BPHA), and a method has been developed for the atomic absorption determination of molybdenum in geological materials using an electrothermal atomizer. It is shown that a complex is formed with a 1:2 ratio of components, which is completely extracted by chloroform from a medium of 0.1-4 M CH1. Extraction and stability constants of he complex formed were calculated. An extraction-atomic absorption method for determining molybdenum in minerals and rocks has been developed.

  14. 4-O-beta-D-galactopyranosyl-D-xylose: a new synthesis and application to the evaluation of intestinal lactase.

    PubMed

    Rivera-Sagredo, A; Fernández-Mayoralas, A; Jiménez-Barbero, J; Martín-Lomas, M; Villanueva, D; Aragón, J J

    1992-04-10

    4-O-beta-D-Galactopyranosyl-D-xylose (2) was prepared from benzyl 2,3-O-isopropylidene-beta-D-xylopyranoside by glycosylation with 2,3,4,6-tetra-O-benzoyl-alpha-D-galactopyranosyl bromide and subsequent deprotection. Compound 2 was hydrolyzed in vitro by intestinal lactase; the Vmax was 25% of that with lactose and the Km was 370mM (cf. 27mM for lactose). Oral administration of 2 suckling rats led to urinary excretion of D-xylose which could be estimated colorimetrically. PMID:1516083

  15. Synthesis, characterization and biological evaluation of tryptamine based benzamide derivatives.

    PubMed

    Aftab, Kiran; Aslam, Kinza; Kousar, Shazia; Nadeem, Muhammad Jawad Ul Hasan

    2016-03-01

    Benzamides and tryptamine are biologically significant compounds, therefore, various benzamide analogous of tryptamine have been efficiently synthesized using tryptamine and different benzoyl chlorides, in order to find new biologically active compounds. The resulting products were then characterized by melting point determination, calculation of Rf values and LC-MS techniques. At last, structure activity relationship (SAR) of the synthesized compounds was evaluated against two microbial strains; Bacillus subtilis and Aspergillus niger. All the five prepared products have shown high yield, sharp characterization and significant resistance against the growth of tested microorganism, providing a new range of tryptamine based benzamide derivatives having significant antimicrobial activities.

  16. An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

    PubMed

    Ye, Zhishi; Dai, Mingji

    2015-05-01

    A novel copper-catalyzed electrophilic amination of cyclopropanols with O-benzoyl-N,N-dialkylhydroxylamines to synthesize various β-aminoketones via a sequence that includes C-C bond cleavage and Csp(3)-N bond formation is reported. The reaction conditions are mild and tolerate a wide range of functional groups including benzoate, tosylate, expoxide, and α,β-unsaturated carbonyls, which are incompatible in the traditional amine nucleophilic conjugate addition and the Mannich reaction conditions. Preliminary mechanistic studies and a proposed catalytic cycle of this umpolung β-aminoketone synthesis process have been described as well. PMID:25885943

  17. Radiopharmaceutical Tracers for Neural Progenitor Cells

    SciTech Connect

    Mangner, Thomas J.

    2006-09-29

    The Technical Report summarizes the results of the synthesis and microPET animal scanning of several compounds labeled with positron-emitting isotopes in normal, neonatal and kainic acid treated (seizure induced) rats as potential PET tracers to image the process of neurogenesis using positron emission tomography (PET). The tracers tested were 3'-deoxy-3'-[F-18]fluorothymidine ([F-18]FLT) and 5'-benzoyl-FTL, 1-(2'-deoxy-2'-[F-18]fluoro-B-D-arabinofuranosyl)-5-bromouracil (FBAU) and 3',5'-dibenzoyl-FBAU, N-[F-18]fluoroacetyl-D-glucosamine (FLAG) and tetraacetyl-FLAG, and L-[1-C-11]leucine.

  18. The Coding Properties of Lysine-accepting Transfer Ribonucleic Acids from Black-eyed Peas 1

    PubMed Central

    Hague, Donald R.; Kofoid, Eric C.

    1971-01-01

    Lysine-accepting transfer RNA from ungerminated and germinated embryo axes of black-eyed peas (Vigna sinensis L. Savi) was fractionated on benzoylated diethylaminoethyl cellulose and reverse phase Freon columns. Cochromatography indicated the presence of two similar lysyl transfer RNA fractions in each tissue. Ribosome binding studies revealed that the larger of the two fractions in each case is specific for the AAG codon, while the smaller one recognizes AAA and AAG. Possible implications of this difference in quantities of isoacceptors in translation of genetic information are discussed. PMID:16657787

  19. Double Deprotonation of Pyridinols Generates Potent Organic Electron-Donor Initiators for Haloarene-Arene Coupling.

    PubMed

    Barham, Joshua P; Coulthard, Graeme; Kane, Ryan G; Delgado, Nathan; John, Matthew P; Murphy, John A

    2016-03-24

    Transition metal-free couplings of haloarenes with arenes, triggered by the use of alkali metal alkoxides in the presence of an organic additive, are receiving significant attention in the literature. Most of the known organic additives effect coupling of iodoarenes, but not bromoarenes, to arenes. Recently it was reported that 2-pyridinecarbinol (11) extends the reaction to aryl bromides. This paper investigates the mechanism, and reports evidence for dianions derived from 11 as electron donors to initiate the reaction. It also proposes routes by which electron-poor benzoyl derivatives can be transformed into electron donors to initiate these reactions. PMID:26938924

  20. N-(5-Chloro-1,3-thia­zol-2-yl)-2,4-difluoro­benzamide

    PubMed Central

    Liu, Xi-Wang; Li, Jian-Yong; Zhang, Han; Yang, Ya-Jun; Zhang, Ji-Yu

    2012-01-01

    The title compound, C10H5ClF2N2OS, was obtained by linking an amino heterocycle and a substituted benzoyl chloride. The dihedral angle between the two rings is 41.2 (2)° and the equalization of the amide C—N bond lengths reveals the existence of conjugation between the benzene ring and the thia­zole unit. In the crystal, pairs of N—H⋯N hydrogen bonds link mol­ecules into inversion dimers. Non-classical C—H⋯F and C—H⋯O hydrogen bonds stabilize the crystal structure. PMID:22719622

  1. On enzymatic pH oscillations in CSTR with outlet regulator

    NASA Astrophysics Data System (ADS)

    Ohmori, Takao; Yu, Weifang; Yamamoto, Takuji; Endo, Akira; Nakaiwa, Masaru; Amemiya, Takashi; Yamaguchi, Tomohiko

    2005-05-01

    The possibility of enzymatic pH oscillations is investigated for a CSTR with an outlet regulator. A linear stability analysis shows that no oscillation is possible in a CSTR without the regulator, using a proton-producing pH-dependent enzymatic reaction. However, self-sustained oscillations are found to occur in a CSTR, where the discharge of substrate is regulated at the outlet. The regions of oscillations in the parameter space are determined using a hydrolysis of N-α-benzoyl- L-arginine ethyl ester with papain. It is found that the region is quite large only when the substrate concentration in the outflow is kept at zero.

  2. An Umpolung Strategy for the Synthesis of β-Aminoketones via Copper-Catalyzed Electrophilic Amination of Cyclopropanols.

    PubMed

    Ye, Zhishi; Dai, Mingji

    2015-05-01

    A novel copper-catalyzed electrophilic amination of cyclopropanols with O-benzoyl-N,N-dialkylhydroxylamines to synthesize various β-aminoketones via a sequence that includes C-C bond cleavage and Csp(3)-N bond formation is reported. The reaction conditions are mild and tolerate a wide range of functional groups including benzoate, tosylate, expoxide, and α,β-unsaturated carbonyls, which are incompatible in the traditional amine nucleophilic conjugate addition and the Mannich reaction conditions. Preliminary mechanistic studies and a proposed catalytic cycle of this umpolung β-aminoketone synthesis process have been described as well.

  3. Redox-Active Star Molecules Incorporating the 4-Benzolypyridinium Cation: Implications for the Charge Transfer Efficiency Along Branches versus Across the Perimeter in Dendrimers

    NASA Technical Reports Server (NTRS)

    Yang, Jin-Hua; Rawashdeh, Abdel Monem M.; Oh, Woon Su; Sotiriou-Leventis, Chariklia; Leventis, Nicholas

    2003-01-01

    We report the redox properties of four star systems incorporating the 4-benzoyl-N-alkylpyridinium cation; the redox potential varies along the branches, but remains constant at fixed radii. Voltammetric analysis (cyclic voltammetry and differential pulse voltammetry) shows that only two of the three redox-active centers in the perimeter are electrochemically accessible during potential sweeps as slow as 20 mV/s and as fast as 10 V/s. On the contrary, both redox centers of a branch are accessible electrochemically within the same time frame. These results are discussed in terms of slow through-space charge transfer and the globular 3-D folding of the molecules.

  4. A new approach to determine the stereospecificity in lipase catalysed hydrolysis using circular dichroism (CD): lipases produce optically active diglycerides from achiral triglycerides.

    PubMed

    Uzawa, H; Nishida, Y; Ohrui, H; Meguro, H

    1990-04-30

    We describe a sensitive CD method for determining the stereospecificity in lipase (E.C.3.1.1.3) catalysed hydrolysis of triacyl glycerols into diacyl glycerols. The diglycerols were converted to chiral tert-butyldimethylsilylated 1,2- or 2,3-di-O-benzoyl-sn-glycerol (5 or 5'), and their CD was measured. This approach showed for the first time that lipases produce optically active diacyl glycerides from achiral tripalmitin and tribenzoyl glyceride with a variable extent of enantioselectivity depending on the acyl groups and the enzymes.

  5. METHOD AND MEANS FOR RADIATION DOSIMETRY

    DOEpatents

    Shulte, J.W.; Suttle, J.F.

    1958-02-18

    This patent relates to a method and device for determining quantities of gamma radiation and x radiation by exposing to such radiation a mature of a purified halogenated hydrocarbon chosen from the class consisting of chloroform, bromoform, tetrachloroethane and 1,1,2trichloroethane, and a minor quantity of a sensitizer chosen from the class consisting of oxygen, benzoyl peroxide, sodium peroxide, and nitrobenzene, the proportion of the sensitizer being at least about 10/sup -5/ moles per cubic centimeter of halogenated hydrocarbon, the total amount of sensitizer depending upon the range of radiation to be measured, and chemically measuring the amount of decomposition generated by the irradiation of the sensitized halogenated hydrocarbon.

  6. Reinvestigation of a New Type of Aerobic Benzoate Metabolism in the Proteobacterium Azoarcus evansii

    PubMed Central

    Mohamed, Magdy El-Said; Zaar, Annette; Ebenau-Jehle, Christa; Fuchs, Georg

    2001-01-01

    The aerobic metabolism of benzoate in the proteobacterium Azoarcus evansii was reinvestigated. The known pathways leading to catechol or protocatechuate do not operate in this bacterium. The presumed degradation via 3-hydroxybenzoyl-coenzyme A (CoA) and gentisate could not be confirmed. The first committed step is the activation of benzoate to benzoyl-CoA by a specifically induced benzoate-CoA ligase (AMP forming). This enzyme was purified and shown to differ from an isoenzyme catalyzing the same reaction under anaerobic conditions. The second step postulated involves the hydroxylation of benzoyl-CoA to a so far unknown product by a novel benzoyl-CoA oxygenase, presumably a multicomponent enzyme system. An iron-sulfur flavoprotein, which may be a component of this system, was purified and characterized. The homodimeric enzyme had a native molecular mass of 98 kDa as determined by gel filtration and contained 0.72 mol flavin adenine dinucleotide (FAD), 10.4 to 18.4 mol of Fe, and 13.3 to 17.9 mol of acid-labile sulfur per mol of native protein, depending on the method of protein determination. This benzoate-induced enzyme catalyzed a benzoyl-CoA-, FAD-, and O2-dependent NADPH oxidation surprisingly without hydroxylation of the aromatic ring; however, H2O2 was formed. The gene (boxA, for benzoate oxidation) coding for this protein was cloned and sequenced. It coded for a protein of 46 kDa with two amino acid consensus sequences for two [4Fe-4S] centers at the N terminus. The deduced amino acid sequence showed homology with subunits of ferredoxin-NADP reductase, nitric oxide synthase, NADPH-cytochrome P450 reductase, and phenol hydroxylase. Upstream of the boxA gene, another gene, boxB, encoding a protein of 55 kDa was found. The boxB gene exhibited homology to open reading frames in various other bacteria which code for components of a putative aerobic phenylacetyl-CoA oxidizing system. The boxB gene product was one of at least five proteins induced when A. evansii

  7. High frequency (27.12 MHz) activation of the radical curing of unsaturated polyesters in styrene solution

    SciTech Connect

    Alazard, P.; Gourdenne, A.

    1996-12-31

    The crosslinking reaction of a divinylester resin of epoxy-acrylic type in styrene solution is activated by high frequencies at 27.12 MHz. The samples to be cured are positioned between two parallel steel plates used as electrodes and an electrical voltage is applied. A parametrical study is described, where the applied electrical voltage, or power, and the concentration of benzoyl peroxide, which is the radical initiator, are taken into account. The optimization of the electromagnetic curing is performed through the determination of the glassy transition temperature of the final products.

  8. N-acyldithieno[3,2-b:2',3'-d]pyrroles: second generation dithieno[3,2-b:2',3'-d]pyrrole building blocks with stabilized energy levels.

    PubMed

    Evenson, Sean J; Rasmussen, Seth C

    2010-09-17

    A new class of dithieno[3,2-b:2',3'-d]pyrroles (DTPs) incorporating N-acyl groups have been prepared from 3-bromothiophene via copper-catalyzed amidation. The utilization of various electron-withdrawing acyl groups has allowed stabilization of the HOMO and LUMO energy levels of these popular building blocks for conjugated materials. The synthesis and characterization of this new class of compounds is described, including electrochemical and photophysical data for all compounds and X-ray structural data for the octanoyl, benzoyl, and cyclohexanoyl functionalized compounds. Initial polymers generated via electropolymerization are also reported.

  9. Glycal assembly by the in situ generation of glycosyl dithiocarbamates.

    PubMed

    Padungros, Panuwat; Alberch, Laura; Wei, Alexander

    2012-07-01

    Glycal assembly offers an expedient entry into β-linked oligosaccharides, but epoxyglycal donors can be capricious in their reactivities. Treatment with Et(2)NH and CS(2) enables their in situ conversion into glycosyl dithiocarbamates, which can be activated by copper triflate for coupling with complex or sterically congested acceptors. The coupling efficiency can be further enhanced by in situ benzoylation, as illustrated in an 11-step synthesis of a branched hexasaccharide from glucals in 28% isolated yield and just four chromatographic purifications. PMID:22686424

  10. Beta-carboline alkaloids from a Korean tunicate Eudistoma sp.

    PubMed

    Wang, Weihong; Nam, Sang-Jip; Lee, Byoung-Chan; Kang, Heonjoong

    2008-02-01

    Seven new beta-carboline-based metabolites, designated as eudistomins Y1-Y7 ( 1- 7), were isolated from a tunicate of the genus Eudistoma collected near Tong-Yeong City, South Sea, Korea. These new metabolites differ from previously isolated marine metabolites due to the presence of a benzoyl group attached to the beta-carboline nucleus at C-1. Eudistomins Y 1-Y 7 were evaluated for their antibacterial activity, and eudistomin Y6 exhibited moderate antibacterial activity against Gram-positive bacteria Staphylococcus epidermis and Bacillus subtilis without cytotoxicity in the MTT assay at 100 microM. PMID:18247569

  11. The Coding Properties of Lysine-accepting Transfer Ribonucleic Acids from Black-eyed Peas.

    PubMed

    Hague, D R; Kofoid, E C

    1971-09-01

    Lysine-accepting transfer RNA from ungerminated and germinated embryo axes of black-eyed peas (Vigna sinensis L. Savi) was fractionated on benzoylated diethylaminoethyl cellulose and reverse phase Freon columns. Cochromatography indicated the presence of two similar lysyl transfer RNA fractions in each tissue. Ribosome binding studies revealed that the larger of the two fractions in each case is specific for the AAG codon, while the smaller one recognizes AAA and AAG. Possible implications of this difference in quantities of isoacceptors in translation of genetic information are discussed.

  12. Influence of the amine salt anion on the synergic solvent extraction of praseodymium with mixtures of chelating extractants and tridodecylamine

    SciTech Connect

    Dukov, I.L.; Jordanov, V.M.

    1995-11-01

    The solvent extraction of Pr with thenoyltrifluoroacetone, (HTTA) or 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one(HP) and tridodecylammonium salt (TDAHA,A{sup -} = Cl{sup -},NO{sub 3}{sup -}, ClO{sub 4}{sup -}) in C{sub 6}H{sub 6} has been studied. The composition of the extracted species has been determined as Pr(TTA){sub 3} TDAHA and TDAH{sup +}[PrP{sub 4}]{sup -}. The values of the equilibrium constants, have been calculated. The extraction mechanism has been discussed on the basis of the experimental data. 34 refs., 6 figs., 2 tabs.

  13. Two polymorphs of trans-[3-(3-nitro­phen­yl)oxiran-2-yl](phen­yl)methanone

    PubMed Central

    Greenberg, Fred H.; Nazarenko, Alexander Y.

    2016-01-01

    The title compound, C15H11NO4, crystallizes in two polymorphic forms, centrosymmetric monoclinic and chiral ortho­rhom­bic. The geometry of the mol­ecules in the two polymorphs is slightly different, possibly due to inter­molecular inter­actions. There are no classical hydrogen bonding in these two structures. However, a number of C—H⋯O inter­molecular inter­actions, involving both O atoms of the nitro as well the benzoyl groups, stabilize the crystal structures. PMID:27555962

  14. Immobilization-stabilization of proteases as a tool to improve the industrial design of peptide synthesis.

    PubMed

    Blanco, R M; Bastida, A; Cuesta, C; Alvaro, G; Fernandez-Lafuente, R; Rosell, C M; Guisan, J M

    1991-01-01

    Synthesis of dipeptides benzoyl Arginine leucinamide and kyotorphin catalyzed by highly stabilized derivatives of trypsin and chymotrypsin have been performed. Extreme experimental conditions could be tested and parameters of industrial interest could be improved provided the high activity and stability of the derivatives in these unfavourable environments. Thermodynamically controlled synthesis catalyzed by trypsin could be optimized and 97% conversion was obtained in 90% organic cosolvents. 100% yields were achieved in kinetically controlled synthesis catalyzed by trypsin in aqueous medium in the presence of IM Ammonium Sulphate. Higher starting concentrations of poorly soluble substrates of chymotrypsin could be used in a reaction medium containing 50% DMF and 95% yield were obtained.

  15. Synthesis and antiproliferative activity of benzophenone tagged pyridine analogues towards activation of caspase activated DNase mediated nuclear fragmentation in Dalton's lymphoma.

    PubMed

    Al-Ghorbani, Mohammed; Thirusangu, Prabhu; Gurupadaswamy, H D; Girish, V; Shamanth Neralagundi, H G; Prabhakar, B T; Khanum, Shaukath Ara

    2016-04-01

    A series of benzophenones possessing pyridine nucleus 8a-l were synthesized by multistep reaction sequence and evaluated for antiproliferative activity against DLA cells by in vitro and in vivo studies. The results suggested that, compounds 8b with fluoro group and 8e with chloro substituent at the benzoyl ring of benzophenone scaffold as well as pyridine ring with hydroxy group exhibited significant activity. Further investigation in mouse model suggests that compounds 8b and 8e have the potency to activate caspase activated DNase (endonuclease) which is responsible for DNA fragmentation, a primary hallmark of apoptosis and thereby inhibits the Dalton's lymphoma ascites tumour growth. PMID:26874345

  16. Separation of actinides from lanthanides

    DOEpatents

    Smith, Barbara F.; Jarvinen, Gordon D.; Ryan, Robert R.

    1989-01-01

    An organic extracting solution and an extraction method useful for separating elements of the actinide series of the periodic table from elements of the lanthanide series, where both are in trivalent form. The extracting solution consists of a primary ligand and a secondary ligand, preferably in an organic solvent. The primary ligand is a substituted monothio-1,3-dicarbonyl, which includes a substituted 4-acyl-2-pyrazolin-5-thione, such as 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT). The secondary ligand is a substituted phosphine oxide, such as trioctylphosphine oxide (TOPO).

  17. Extractant composition

    DOEpatents

    Smith, Barbara F.; Jarvinen, Gordon D.; Ryan, Robert R.

    1990-01-01

    An organic extracting solution useful for separating elements of the actinide series of the periodic table from elements of the lanthanide series, where both are in trivalent form. The extracting solution consists of a primary ligand and a secondary ligand, preferably in an organic solvent. The primary ligand is a substituted monothio-1,3-dicarbonyl, which includes a substituted 4-acyl-2-pyrazolin-5-thione, such as 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT). The secondary ligand is a substituted phosphine oxide, such as trioctylphosphine oxide (TOPO).

  18. Persistence of leech repellents on cloth.

    PubMed

    Nath, D R; Das, N G; Das, S C

    1993-05-01

    Trials on persistence of repellent properties of N, N-diethyl phenyl acetamide (DEPA), N,N-diethyl-m-toluamide (DEET), 3acetyl2(2-6-dimethyl-5-heptenyl)oxazolidine(Citronyl) , dimethyl phthalate (DMP) and N-benzoyl piperidine (NBP) on cloth were conducted against land leeches in evergreen rain and deciduous forests of Assam. Results obtained were compared with volatile oil of Zanthoxylum armatum DC. syn. Z. alatum Roxb (Timur) to evaluate its efficacy as leech repellent. DEPA and DEET were found to be the best. Timur oil was at par with Citronyl and exhibited better results than DMP and NBP.

  19. Base catalysed intermolecular cyclisation of N-protected o-amino benzaldehyde/acetophenone with phosphorus/sulphur based allenes: facile synthesis of substituted quinolines.

    PubMed

    Anitha, Mandala; Gangadhararao, G; Kumara Swamy, K C

    2016-04-14

    Reaction of N-Bz protected o-aminobenzaldehyde or acetophenone with allenylphosphonates in the presence of a simple base leads to quaternary carbon substituted phosphono-quinolines which undergo thermal rearrangement to O-phosphorylated quinolines. The present one-pot reaction involves intermolecular cyclisation, dehydration, and benzoyl group rearrangement followed by a novel phosphoryl group migration. The migration was less facile/not observed in the reactions using allenylphosphine oxides and sulphur based allenes wherein only substituted quinolines were obtained in good yields. X-ray structures have been determined for the key products. PMID:26976203

  20. Raman spectroscopy-based detection of chemical contaminants in food powders

    NASA Astrophysics Data System (ADS)

    Chao, Kuanglin; Dhakal, Sagar; Qin, Jianwei; Kim, Moon; Bae, Abigail

    2016-05-01

    Raman spectroscopy technique has proven to be a reliable method for qualitative detection of chemical contaminants in food ingredients and products. For quantitative imaging-based detection, each contaminant particle in a food sample must be detected and it is important to determine the necessary spatial resolution needed to effectively detect the contaminant particles. This study examined the effective spatial resolution required for detection of maleic acid in tapioca starch and benzoyl peroxide in wheat flour. Each chemical contaminant was mixed into its corresponding food powder at a concentration of 1% (w/w). Raman spectral images were collected for each sample, leveled across a 45 mm x 45 mm area, using different spatial resolutions. Based on analysis of these images, a spatial resolution of 0.5mm was selected as effective spatial resolution for detection of maleic acid in starch and benzoyl peroxide in flour. An experiment was then conducted using the 0.5mm spatial resolution to demonstrate Raman imaging-based quantitative detection of these contaminants for samples prepared at 0.1%, 0.3%, and 0.5% (w/w) concentrations. The results showed a linear correlation between the detected numbers of contaminant pixels and the actual concentrations of contaminant.

  1. Structural, thermal and photo-physical data of azo-aromatic TEMPO derivatives before and after their grafting to polyolefins.

    PubMed

    Cicogna, Francesca; Domenichelli, Ilaria; Coiai, Serena; Bellina, Fabio; Lessi, Marco; Spiniello, Roberto; Passaglia, Elisa

    2016-03-01

    The data reported in this paper are complementary to the characterization of 4-(phenylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (AzO-TEMPO) and of the 4-(2-thienylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (ThiO-TEMPO) before and after their grafting to two polyethylene matrices (a copolymer ethylene/α-olefin (co-EO) and a high density polyethylene (HDPE)). Particularly the data reported in this paper confirm the structure (FT-IR analysis), the thermal (TGA and EPR) and the photo-physical (UV-vis) properties of the RO-TEMPO derivatives before and after their grafting. Herein, the FT-IR spectrum and TGA thermogram of ThiO-TEMPO were compared with those of AzO-TEMPO. Moreover, the superimposition of UV-vis spectra collected during the irradiation under 366 or 254 nm emitting lamp of AzO-TEMPO and ThiO-TEMPO in acetonitrile solution are reported. Finally, a complete DSC characterization of the functionalized POs is shown. DOI of original article: 〈http://dx.doi.org/10.1016/j.polymer.2015.11.018〉 [1]. PMID:26909368

  2. Structural, thermal and photo-physical data of azo-aromatic TEMPO derivatives before and after their grafting to polyolefins

    PubMed Central

    Cicogna, Francesca; Domenichelli, Ilaria; Coiai, Serena; Bellina, Fabio; Lessi, Marco; Spiniello, Roberto; Passaglia, Elisa

    2016-01-01

    The data reported in this paper are complementary to the characterization of 4-(phenylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (AzO-TEMPO) and of the 4-(2-thienylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (ThiO-TEMPO) before and after their grafting to two polyethylene matrices (a copolymer ethylene/α-olefin (co-EO) and a high density polyethylene (HDPE)). Particularly the data reported in this paper confirm the structure (FT-IR analysis), the thermal (TGA and EPR) and the photo-physical (UV–vis) properties of the RO-TEMPO derivatives before and after their grafting. Herein, the FT-IR spectrum and TGA thermogram of ThiO-TEMPO were compared with those of AzO-TEMPO. Moreover, the superimposition of UV–vis spectra collected during the irradiation under 366 or 254 nm emitting lamp of AzO-TEMPO and ThiO-TEMPO in acetonitrile solution are reported. Finally, a complete DSC characterization of the functionalized POs is shown. DOI of original article: 〈http://dx.doi.org/10.1016/j.polymer.2015.11.018〉 [1] PMID:26909368

  3. New soluble electrically conductive n-substituted polyanilines

    SciTech Connect

    Mikhael, M.G.; Padias, A.B.; Hall, H.K. Jr.

    1996-10-01

    The solubility of polyaniline {open_quotes}emeraldine base{close_quotes} (Pan-EB) was modified through substituting the N-hydrogen atoms of polyaniline by various acyl and benzyl groups. Pan-EB was allowed to react with benzoyl chloride, p-t-butylbenzoyl chloride or pivaloyl chloride in N,N{prime}-dimethylpropylene urea (DMPU). While the benzoyl and pivaloyl derivatives showed very poor solubility in common organic solvents, the p-t-butylbenzoyl derivative is readily soluble in THF, chloroform, DMSO, etc. Benzyl chlorides, did not react with Pan-EB in absence of bases. The nitrogen anion of Pan-EB, obtained from reaction of the polymer with NaH, reacted with p-t-butylbenzyl chloride to produce a soluble, high molecular weight, electrically conductive (4.3 x 10{sup -1} S cm{sup - 1}) Pan derivative. The reaction conditions were critical. High NaH concentration and long reaction time led to insoluble crosslinked products, which was explained by the competitive addition of the nitrogen anions to the C=C of the quinonimine rings (Michael addition). Successful N-anion trapping requires sufficiently electrophilic reagent such as benzyl chlorides.

  4. Sucrose octabenzoate: assignment of 13C and 1H resonances of the sucrose moiety and the 13C resonances of the carbonyl carbons. Use of 13C-n.m.r. spectroscopy for the study of selective deacylation.

    PubMed

    Colquhoun, I J; Haines, A H; Konowicz, P A; Jones, H F

    1990-09-19

    Assignment of the 1H and 13C signals arising from the carbohydrate portion of sucrose octabenzoate has been achieved using homonuclear shift correlation experiments (COSY) and one-bond 1H-13C heteronuclear shift correlation measurements, respectively. The 13C resonances of the carbonyl carbon atoms of the eight benzoyl groups are readily distinguished for solutions in benzene-d6-pyridine-d5 (1:1), and have been assigned by means of three-bond 1H-13C shift correlation studies coupled with measurement of the 13C-n.m.r. spectrum of a sucrose octabenzoate specifically labelled with 13C in some of the carbonyl groups. With this assignment, products of partial deacylation of the octabenzoate may readily be identified by treatment with excess of benzoyl-carbonyl-13C chloride followed by measurement of the 13C-n.m.r. spectrum of the labelled sucrose octabenzoate, so prepared, in the carbonyl region. PMID:2276151

  5. Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae)

    NASA Astrophysics Data System (ADS)

    Vujisić, Ljubodrag V.; Vučković, Ivan M.; Makarov, Slobodan E.; Ilić, Bojan S.; Antić, Dragan Ž.; Jadranin, Milka B.; Todorović, Nina M.; Mrkić, Ivan V.; Vajs, Vlatka E.; Lučić, Luka R.; Ćurčić, Božidar P. M.; Mitić, Bojan M.

    2013-09-01

    The geophilomorph centipede, Himantarium gabrielis, when disturbed, discharges a viscous and proteinaceous secretion from the sternal glands. This exudate was found by gas chromatography-mass spectrometry, liquid chromatography-high resolution mass spectrometry, liquid chromatography-mass spectrometry-mass spectrometry and NMR analyses to be composed of hydrogen cyanide, benzaldehyde, benzoyl nitrile, benzyl nitrile, mandelonitrile, mandelonitrile benzoate, 3,7,6 O-trimethylguanine (himantarine), farnesyl 2,3-dihydrofarnesoate and farnesyl farnesoate. This is the first report on the presence of benzyl nitrile and mandelonitrile benzoate in secreted substances from centipedes. Farnesyl 2,3-dihydrofarnesoate is a new compound, while himantarine and farnesyl farnesoate were not known as natural products. A post-secretion release of hydrogen cyanide by reaction of mandelonitrile and benzoyl nitrile was observed by NMR, and hydrogen cyanide signals were completely assigned. In addition, a protein component of the secretion was analysed by electrophoresis which revealed the presence of a major 55 kDa protein. Analyses of the defensive exudates of other geophilomorph families should produce further chemical surprises.

  6. Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae).

    PubMed

    Vujisić, Ljubodrag V; Vučković, Ivan M; Makarov, Slobodan E; Ilić, Bojan S; Antić, Dragan Z; Jadranin, Milka B; Todorović, Nina M; Mrkić, Ivan V; Vajs, Vlatka E; Lučić, Luka R; Curčić, Božidar P M; Mitić, Bojan M

    2013-09-01

    The geophilomorph centipede, Himantarium gabrielis, when disturbed, discharges a viscous and proteinaceous secretion from the sternal glands. This exudate was found by gas chromatography-mass spectrometry, liquid chromatography-high resolution mass spectrometry, liquid chromatography-mass spectrometry-mass spectrometry and NMR analyses to be composed of hydrogen cyanide, benzaldehyde, benzoyl nitrile, benzyl nitrile, mandelonitrile, mandelonitrile benzoate, 3,7,6O-trimethylguanine (himantarine), farnesyl 2,3-dihydrofarnesoate and farnesyl farnesoate. This is the first report on the presence of benzyl nitrile and mandelonitrile benzoate in secreted substances from centipedes. Farnesyl 2,3-dihydrofarnesoate is a new compound, while himantarine and farnesyl farnesoate were not known as natural products. A post-secretion release of hydrogen cyanide by reaction of mandelonitrile and benzoyl nitrile was observed by NMR, and hydrogen cyanide signals were completely assigned. In addition, a protein component of the secretion was analysed by electrophoresis which revealed the presence of a major 55 kDa protein. Analyses of the defensive exudates of other geophilomorph families should produce further chemical surprises.

  7. A comparative study of tea-tree oil versus benzoylperoxide in the treatment of acne.

    PubMed

    Bassett, I B; Pannowitz, D L; Barnetson, R S

    1990-10-15

    Tea-tree oil (an essential oil of the Australian native tree Melaleuca alternifolia) has long been regarded as a useful topical antiseptic agent in Australia and has been shown to have a variety of antimicrobial activities; however, only anecdotal evidence exists for its efficacy in the treatment of various skin conditions. We have performed a single-blind, randomised clinical trial on 124 patients to evaluate the efficacy and skin tolerance of 5% tea-tree oil gel in the treatment of mild to moderate acne when compared with 5% benzoyl peroxide lotion. The results of this study showed that both 5% tea-tree oil and 5% benzoyl peroxide had a significant effect in ameliorating the patients' acne by reducing the number of inflamed and non-inflamed lesions (open and closed comedones), although the onset of action in the case of tea-tree oil was slower. Encouragingly, fewer side effects were experienced by patients treated with tea-tree oil.

  8. Cumulative irritancy comparison of adapalene gel 0.1% versus other retinoid products when applied in combination with topical antimicrobial agents.

    PubMed

    Brand, Barbara; Gilbert, Richard; Baker, Michael D; Poncet, Michel; Greenspan, Alan; Georgeian, Kathleen; Soloff, Andrew-Marc

    2003-09-01

    This randomized, investigator-blinded study evaluated the level of skin tolerance to adapalene gel 0.1%, tretinoin cream 0.025%, or tretinoin microsphere gel 0.1% when applied in combination with clindamycin phosphate lotion 1%, erythromycin gel 2%, benzoyl peroxide gel 5%, or erythromycin-benzoyl peroxide gel. A total of 37 subjects underwent daily application of the topical antimicrobial and retinoid products to sites on their upper back under protective patches for approximately 16 hours each day; Friday patches were left in place over the weekend. Testing continued daily for 3 weeks or until discontinuation caused by a severe adverse reaction to any of the test products or to the patch. Adapalene gel 0.1% demonstrated statistically significantly (P <.001) less irritation after repeated application under occlusive conditions than tretinoin cream 0.025% or tretinoin microsphere gel 0.1%. Moreover, the application of adapalene gel 0.1% under these conditions, concomitantly with various antimicrobial agents, was safe and well tolerated in this subject population. In view of its low irritation potential and its efficacy, adapalene gel 0.1%, in combination with antimicrobial agents should be considered for the treatment of acne vulgaris.

  9. [Acne vulgaris].

    PubMed

    Zouboulis, C C

    2014-08-01

    Acne vulgaris is worldwide the most common skin disease. Acne is an inflammatory disorder in whose emergence androgens, PPAR ligands, the IGF-1 signaling pathway, regulating neuropeptides and environmental factors are probably involved. These factors interrupt the natural cycling process in the sebaceous gland follicle and support the transition of microcomedones to comedones and inflammatory lesions. Proinflammatory lipids and cytokines are mediators for the development of acne lesions. Bacterial antigens can potentate the inflammatory phenomena. Acne is predominantly treated with combination therapy. Selecting a treatment regimen depends on the exact classification of acne type and severity. The development of scars is the main criterion for the choice of systemic therapy. Retinoids for mild comedonal acne and the combination of retinoids with antibiotics and/or benzoyl peroxide for mild to moderate papulopustular acne are the drugs of first choice for topical treatment. The use of topical antibiotics is not recommended any more because of the development of resistant bacterial strains. Systemic antibiotics, in combination with topical retinoids and/or benzoyl peroxide, for moderate papular/nodular acne and isotretinoin for severe nodular/conglobate acne are the columns of systemic acne treatment. Systemic anti-androgens are used in women against moderate papulopustular acne. Due to advances in the understanding of the underlying inflammatory mechanisms in recent years the development of new therapeutic agents with good efficacy and better side effect profile should be expected in the future.

  10. Thymol and eugenol derivatives as potential antileishmanial agents.

    PubMed

    de Morais, Selene Maia; Vila-Nova, Nadja Soares; Bevilaqua, Claudia Maria Leal; Rondon, Fernanda Cristina; Lobo, Carlos Henrique; de Alencar Araripe Noronha Moura, Arlindo; Sales, Antônia Débora; Rodrigues, Ana Paula Ribeiro; de Figuereido, José Ricardo; Campello, Claudio Cabral; Wilson, Mary E; de Andrade, Heitor Franco

    2014-11-01

    In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim of this work was to survey natural active compounds to find new molecules with high activity and low toxicity against Leishmania infantum chagasi. The compounds thymol and eugenol were chosen to be starting compounds to synthesize acetyl and benzoyl derivatives and to test their antileishmanial activity in vitro and in vivo against L. i. chagasi. A screening assay using luciferase-expressing promastigotes was used to measure the growth inhibition of promastigotes, and an ELISA in situ was performed to evaluate the growth inhibition of amastigote. For the in vivo assay, thymol and eugenol derivatives were given IP to BALB/c mice at 100mg/kg/day for 30 days. The thymol derivatives demonstrated the greater activity than the eugenol derivatives, and benzoyl-thymol was the best inhibitor (8.67 ± 0.28 μg/mL). All compounds demonstrated similar activity against amastigotes, and acetyl-thymol was more active than thymol and the positive control drug amphotericin B. Immunohistochemistry demonstrated the presence of Leishmania amastigote only in the spleen but not the liver of mice treated with acetyl-thymol. Thus, these synthesized derivatives demonstrated anti-leishmanial activity both in vitro and in vivo. These may constitute useful compounds to generate new agents for treatment of leishmaniasis.

  11. Spinal astrocytes produce and secrete dynorphin neuropeptides.

    PubMed

    Wahlert, Andrew; Funkelstein, Lydiane; Fitzsimmons, Bethany; Yaksh, Tony; Hook, Vivian

    2013-04-01

    Dynorphin peptide neurotransmitters (neuropeptides) have been implicated in spinal pain processing based on the observations that intrathecal delivery of dynorphin results in proalgesic effects and disruption of extracellular dynorphin activity (by antisera) prevents injury evoked hyperalgesia. However, the cellular source of secreted spinal dynorphin has been unknown. For this reason, this study investigated the expression and secretion of dynorphin-related neuropeptides from spinal astrocytes (rat) in primary culture. Dynorphin A (1-17), dynorphin B, and α-neoendorphin were found to be present in the astrocytes, illustrated by immunofluorescence confocal microscopy, in a discrete punctate pattern of cellular localization. Measurement of astrocyte cellular levels of these dynorphins by radioimmunoassays confirmed the expression of these three dynorphin-related neuropeptides. Notably, BzATP (3'-O-(4-benzoyl)benzoyl adenosine 5'-triphosphate) and KLA (di[3-deoxy-D-manno-octulosonyl]-lipid A) activation of purinergic and toll-like receptors, respectively, resulted in stimulated secretion of dynorphins A and B. However, α-neoendorphin secretion was not affected by BzATP or KLA. These findings suggest that dynorphins A and B undergo regulated secretion from spinal astrocytes. These findings also suggest that spinal astrocytes may provide secreted dynorphins that participate in spinal pain processing.

  12. Physiological and Proteomic Adaptation of “Aromatoleum aromaticum” EbN1 to Low Growth Rates in Benzoate-Limited, Anoxic Chemostats

    PubMed Central

    Trautwein, Kathleen; Lahme, Sven; Wöhlbrand, Lars; Feenders, Christoph; Mangelsdorf, Kai; Harder, Jens; Steinbüchel, Alexander; Blasius, Bernd; Reinhardt, Richard

    2012-01-01

    “Aromatoleum aromaticum” EbN1 was cultivated at different growth rates in benzoate-limited chemostats under nitrate-reducing conditions. Physiological characteristics, proteome dynamics, phospholipid-linked fatty acid (PLFA) composition, and poly(3-hydroxybutyrate) (PHB) content were analyzed in steady-state cells at low (μlow) (0.036 h−1), medium (μmed) (0.108 h−1), and high (μhigh) (0.180 h−1) growth rates. A positive correlation to growth rate was observed for cellular parameters (cell size, and DNA and protein contents). The free energy consumed for biomass formation steadily increased with growth rate. In contrast, the energy demand for maintenance increased only from μlow to μmed and then remained constant until μhigh. The most comprehensive proteomic changes were observed at μlow compared to μhigh. Uniformly decreased abundances of protein components of the anaerobic benzoyl coenzyme A (benzoyl-CoA) pathway, central carbon metabolism, and information processing agree with a general deceleration of benzoate metabolism and cellular processes in response to slow growth. In contrast, increased abundances were observed at μlow for diverse catabolic proteins and components of uptake systems in the absence of the respective substrate (aromatic or aliphatic compounds) and for proteins involved in stress responses. This potential catabolic versatility and stress defense during slow growth may be interpreted as preparation for future needs. PMID:22366417

  13. Structural, thermal and photo-physical data of azo-aromatic TEMPO derivatives before and after their grafting to polyolefins.

    PubMed

    Cicogna, Francesca; Domenichelli, Ilaria; Coiai, Serena; Bellina, Fabio; Lessi, Marco; Spiniello, Roberto; Passaglia, Elisa

    2016-03-01

    The data reported in this paper are complementary to the characterization of 4-(phenylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (AzO-TEMPO) and of the 4-(2-thienylazo)-benzoyl-2,2,6,6-tetramethylpiperidine-1-oxyl radical (ThiO-TEMPO) before and after their grafting to two polyethylene matrices (a copolymer ethylene/α-olefin (co-EO) and a high density polyethylene (HDPE)). Particularly the data reported in this paper confirm the structure (FT-IR analysis), the thermal (TGA and EPR) and the photo-physical (UV-vis) properties of the RO-TEMPO derivatives before and after their grafting. Herein, the FT-IR spectrum and TGA thermogram of ThiO-TEMPO were compared with those of AzO-TEMPO. Moreover, the superimposition of UV-vis spectra collected during the irradiation under 366 or 254 nm emitting lamp of AzO-TEMPO and ThiO-TEMPO in acetonitrile solution are reported. Finally, a complete DSC characterization of the functionalized POs is shown. DOI of original article: 〈http://dx.doi.org/10.1016/j.polymer.2015.11.018〉 [1].

  14. Combined effects of microwaves, electron beams and polyfunctional monomers on rubber vulcanization.

    PubMed

    Manaila, Elena; Martin, Diana; Stelescu, Daniela Zuga; Craciun, Gabriela; Ighigeanu, Daniel; Matei, Constantin

    2009-01-01

    This paper presents comparative results obtained by conventional vulcanization with benzoyl peroxide (CV-BP), separate electron beam vulcanization (EB-V) and simultaneous electron beam and microwave vulcanization (EB+MW-V) applied to two kind of rubber samples: EVA (ethylene vinyl acetate) rubber-sample (EVA-sample) and EPDM (ethylene-propylene terpolymer) rubber-sample (EPDM-sample). The EVA-samples contain 61.54% EVA Elvax 260, 30.77% carbon black, 1.85% TAC (triallylcyanurate) polyfunctional monomer and 5.84% filler (zinc oxide, stearic acid, polyethylene glycol and antioxidant). The EPDM-samples contain 61.54% EPDM Nordel 4760, 30.77% carbon black, 1.85% TMPT (trimethylopropane trimethacrylate) polyfunctional monomer and 5.84% filler (zinc oxide, stearic acid, polyethylene glycol and antioxidant). The rubber samples designed for different vulcanization methods were obtained from raw rubber mixtures, as compressed sheets of 2 mm in the polyethylene foils to minimize oxidation. For EB and EB + MW treatments the sheets were cut in rectangular shape 0.15 x 0.15 m2. The physical properties of samples obtained by CV-BP EV-Vand EB + MW-V methods were evaluated by measuring the tearing strength, residual elongation, elongation at break, tensile strength, 300% modulus, 100% modulus, elasticity and hardness. The obtained results demonstrate an improvement of rubber several properties obtained by EB and EB + MW processing as compared to classical procedure using benzoyl peroxide. PMID:21384707

  15. Low-temperature depolymerization of polysiloxanes with iron catalysis.

    PubMed

    Enthaler, Stephan; Kretschmer, Robert

    2014-07-01

    The easy accessibility and high adjustability of polymers mainly accounts for the great impact of such materials on modern society. Besides this great success, an important matter is the accumulation of large amounts of end-of-life polymers, which are mainly deposited in landfills or converted by thermal recycling or down-cycling to low-quality materials. In contrast to that, the depolymerization of end-of-life polymers to monomers, which can be applied as feedstock in polymerization chemistry for high-quality polymers, is only carried out for a small fraction of waste. Polysiloxanes are extensively used in a diverse array of technological applications. Based on intrinsic properties of polymers, depolymerization is challenging and only a few high-temperature or less environment-friendly processes have been reported. In this regard, we have set up a capable low-temperature protocol for the depolymerization of poly(dimethylsiloxane) in the presence of catalytic amounts of simple iron salts in combination with different depolymerization reagents. The application of benzoyl fluoride, benzoyl chloride/potassium fluoride, or benzoic anhydride/potassium fluoride as depolymerization reagents affords difluorodimethylsilane or 1,3-difluoro-1,1,3,3-tetramethyldisilxanes as products, which are interesting building blocks for the synthesis of new polymers and allow an overall recycling of polysiloxanes. PMID:24825826

  16. Thermodynamic functions of Ni(II) complexes with 5-(2-hydroxyphenyl)-pyrazole derivatives. A potentiometric study

    NASA Astrophysics Data System (ADS)

    Deosarkar, S. D.; Narwade, M. L.; Thakre, V. J.

    2013-10-01

    Proton-ligand dissociation constants of five biologically important pyrazole derivatives, viz. [5-(2-hydroxyphenyl)-3-(pyridin-3-yl)-4-benzoyl]-pyrazol (HPPBP), [5-(2-hydroxyphenyl)-3-(3-nitrophenyl)-4-(3-pyridinoyl)]-pyrazol (HPNPPP), [5-(2-hydroxyphenyl)-3-(3-nitrophenyl)-4-benzoyl]-pyrazol (HPNPBP), [5-(2-hydroxyphenyl)-3-phenyl-4-(3-pyridinoyl)]-pyrazol (HPPPP), and [5-(2-hydroxyphenyl)-3-(3-nitrophenyl)-4-(2-furoyl) pyrazol (HPNPFP) and metal ligand stability constants of their Ni(II) complexes in 70% (v/v) dioxane-water and 0.1 M KNO3 were determined at 298.15, 303.15, and 308.15 K by potentiometric method. Thermodynamic functions, such as, free energy change (Δ G ○), enthalpy change (Δ H ○) and entropy (Δ S ○) change for dissociation and complex formation have been estimated form temperature dependence of proton-ligand and metal-ligand stability constants and interpreted in terms of feasibility of these processes.

  17. Thymol and eugenol derivatives as potential antileishmanial agents.

    PubMed

    de Morais, Selene Maia; Vila-Nova, Nadja Soares; Bevilaqua, Claudia Maria Leal; Rondon, Fernanda Cristina; Lobo, Carlos Henrique; de Alencar Araripe Noronha Moura, Arlindo; Sales, Antônia Débora; Rodrigues, Ana Paula Ribeiro; de Figuereido, José Ricardo; Campello, Claudio Cabral; Wilson, Mary E; de Andrade, Heitor Franco

    2014-11-01

    In Northeastern Brazil visceral leishmaniasis is endemic with lethal cases among humans and dogs. Treatment is toxic and 5-10% of humans die despite treatment. The aim of this work was to survey natural active compounds to find new molecules with high activity and low toxicity against Leishmania infantum chagasi. The compounds thymol and eugenol were chosen to be starting compounds to synthesize acetyl and benzoyl derivatives and to test their antileishmanial activity in vitro and in vivo against L. i. chagasi. A screening assay using luciferase-expressing promastigotes was used to measure the growth inhibition of promastigotes, and an ELISA in situ was performed to evaluate the growth inhibition of amastigote. For the in vivo assay, thymol and eugenol derivatives were given IP to BALB/c mice at 100mg/kg/day for 30 days. The thymol derivatives demonstrated the greater activity than the eugenol derivatives, and benzoyl-thymol was the best inhibitor (8.67 ± 0.28 μg/mL). All compounds demonstrated similar activity against amastigotes, and acetyl-thymol was more active than thymol and the positive control drug amphotericin B. Immunohistochemistry demonstrated the presence of Leishmania amastigote only in the spleen but not the liver of mice treated with acetyl-thymol. Thus, these synthesized derivatives demonstrated anti-leishmanial activity both in vitro and in vivo. These may constitute useful compounds to generate new agents for treatment of leishmaniasis. PMID:25281268

  18. Introducing Freshmen Students to the Practice of Solid-Phase Synthesis

    NASA Astrophysics Data System (ADS)

    Taralp, Alpay; Hulusi Türkseven, Can; Özgür Çakmak, Atilla; Çengel, Ömer

    2002-01-01

    A one-semester laboratory project on solid-phase peptide chemistry was designed pedagogically to cater to freshman science students. The approach not only permitted multistep syntheses that would be considered impractical in solution, but also gave students insight into fundamental aspects of research at an early stage of development. Young scientists prepared Bz-Asn-Asn-Phe and Bz-Asn-Gln-Phe--peptides envisaged as potential competitive inhibitors of chymotrypsin. The synthesis, defined by an attachment-deprotection cycle, two elongation-deprotection cycles, and a benzoyl-capping protocol, was completed manually on Wang resin using Fmoc chemistry. Students quantified the yield of each condensation and deprotection reaction by measuring levels of dibenzylfulvene chromophore, a stoichiometrically afforded by-product. Benzoylation of the N-terminus was confirmed by employing a cadmium-ninhydrin reagent. The group also ascertained, through use of a chromogenic substrate, that chymotrypsin-catalyzed hydrolysis was impeded slightly when carried out in the presence of target peptides. Supplementary analyses supporting peptide purity and composition were given to students. Grading was based on laboratory participation, project proposals, reports, and a concluding slide-show presentation made to peers and colleagues. While the project was time-consuming overall, students acquired an impression of research work and an appreciation of the utility of solid-phase methods.

  19. Characterization of flavonols in cranberry (Vaccinium macrocarpon) powder.

    PubMed

    Vvedenskaya, Irina O; Rosen, Robert T; Guido, Jane E; Russell, David J; Mills, Kent A; Vorsa, Nicholi

    2004-01-28

    Flavonoids were extracted from cranberry powder with acetone and ethyl acetate and subsequently fractionated with Sephadex LH-20 column chromatography. The fraction eluted with a 60% methanol solution was composed primarily of phenolic constituents with maximum absorbance at 340 nm. A high-performance liquid chromatography procedure was developed, which resolved 22 distinct peaks with UV/vis and mass spectra corresponding to flavonol glycoside conjugates. Six new constituents not previously reported in cranberry or in cranberry products were determined through NMR spectroscopy to be myricetin-3-beta-xylopyranoside, quercetin-3-beta-glucoside, quercetin-3-alpha-arabinopyranoside, 3'-methoxyquercetin-3-alpha-xylopyranoside, quercetin-3-O-(6' '-p-coumaroyl)-beta-galactoside, and quercetin-3-O-(6' '-benzoyl)-beta-galactoside. Quercetin-3-O-(6' '-p-coumaroyl)-beta-galactoside and quercetin-3-O-(6' '-benzoyl)-beta-galactoside represent a new class of cranberry flavonol compounds with three conjugated components consisting of a flavonol, sugar, and carboxylic acid (benzoic or hydroxycinnamic acids). This is also the first report identifying quercetin-3-arabinoside in both furanose and pyranose forms in cranberry. Elucidation of specific flavonol glycosides in cranberry is significant since the specificity of the sugar moiety may play a role in the bioavailability of the flavonol glycosides in vivo.

  20. The treatment of skin carcinoma, induced by UV B radiation, using 1-oxo-5beta, 6beta-epoxy-witha-2-enolide, isolated from the roots of Withania somnifera, in a rat model.

    PubMed

    Mathur, S; Kaur, P; Sharma, M; Katyal, A; Singh, B; Tiwari, M; Chandra, R

    2004-07-01

    Histopathological studies of the cutaneous tissues of Wistar rats exposed to UV B radiation (294 nm) for 20 days and rats exposed to UV B radiation for 20 days, followed by topical treatment with benzoyl peroxide, a tumor promoter (20 mg/animal/0.2 ml acetone) twice a week for 1 month, and kept under observation for 12 weeks, demonstrate the development of malignancy. Pretreatment of the animals with 1-oxo-5beta, 6beta-epoxy-witha-2-enolide (20 mg/kg bwt.), isolated from the roots of Withania somnifera, prior to exposing the animals to UV B radiation, prevents the incidence of skin carcinoma. The administration of 1-oxo-5beta, 6beta-epoxy-witha-2-enolide, to the animals after exposing them to UV B radiation/UV B radiation and benzoyl peroxide also prevents the occurrence of malignancy in the cutaneous tissue. Immunohistochemical staining of the cutaneous tissues of rats exposed to UV B radiation show the presence of p53 + foci (clusters of cells containing the mutated p53 protein), whereas an absence of p53 + foci is observed in animals pretreated with 1-oxo-5beta, 6beta-epoxy-witha-2-enolide. These results prove that 1-oxo-5beta, 6beta-epoxy-witha-2-enolide has the potential for acting as an effective agent to prevent the incidence of skin carcinoma induced by UV B radiation. PMID:15330502

  1. Hyperpolization-activated Ca(2+) channels in guard cell plasma membrane are involved in extracellular ATP-promoted stomatal opening in Vicia faba.

    PubMed

    Wang, Fang; Jia, Juanjuan; Wang, Yufang; Wang, Weixia; Chen, Yuling; Liu, Ting; Shang, Zhonglin

    2014-09-01

    Extracellular ATP (eATP) plays essential roles in plant growth, development, and stress tolerance. Extracellular ATP-regulated stomatal movement of Arabidopsis thaliana has been reported. Here, ATP was found to promote stomatal opening of Vicia faba in a dose-dependent manner. Three weakly hydrolysable ATP analogs (adenosine 5'-O-(3-thio) triphosphate (ATPγS), 3'-O-(4-benzoyl) benzoyl adenosine 5'-triphosphate (Bz-ATP) and 2-methylthio-adenosine 5'-triphosphate (2meATP)) showed similar effects, indicating that ATP acts as a signal molecule rather than an energy charger. ADP promoted stomatal opening, while AMP and adenosine did not affect stomatal movement. An ATP-promoted stomatal opening was blocked by the NADPH oxidase inhibitor diphenylene iodonium (DPI), the reductant dithiothreitol (DTT) or the Ca(2+) channel blockers GdCl3 and LaCl3. A hyperpolarization-activated Ca(2+) channel was detected in plasma membrane of guard cell protoplast. Extracellular ATP and weakly hydrolyzable ATP analogs activated this Ca(2+) channel significantly. Extracellular ATP-promoted Ca(2+) channel activation was markedly inhibited by DPI or DTT. These results indicated that eATP may promote stomatal opening via reactive oxygen species that regulate guard cell plasma membrane Ca(2+) channels.

  2. A recyclable heavy fluorous tag carrying an allyl alcohol pendant group: design and evaluation toward applications in synthetic carbohydrate chemistry.

    PubMed

    Fukuda, Kazuo; Tojino, Mami; Goto, Kohtaro; Dohi, Hirofumi; Nishida, Yoshihiro; Mizuno, Mamoru

    2015-04-30

    Toward applications in synthetic carbohydrate chemistry, we converted our previous acid-resistant heavy fluorous tag [(Rf)3C-CH2-OH, 1] to allyl alcohol derivatives [(Rf)3C-CH2-O-(CH2)n-CH=CH-CH2-OH, 3 (n=1) or 4 (n=3)] by means of olefin cross metathesis. They were then subjected to β-glycosylation reactions by using a series of glycosyl donors, including glycosyl bromide and trichloroacetimidates. The terminal OH group in 3 and 4 was found to be β-glycosylated in moderate yield when 2,3,4,6-tetra-O-benzoyl-D-galactosyl trichloroacetimidate was used as the glycosyl donor. Upon a detachment reaction using Pd(PPh3)4, the initial heavy fluorous tag 1 was recovered in high yield (>90%) together with 1-hydroxy sugar, indicating that not only the allyl ether linkage in the glycosides but also the internal di-alkyl ether linkage in 4 be cleaved by the action of the Pd-catalyst enabling long-range olefin transmigration. Potential utility was demonstrated by using the tetra-O-benzoyl-β-D-galactosylated derivative of 3 in a series of deprotection, protection and glycosylation reactions, which were conductible in high yields without using chromatographic purification process. These findings prompt us to propose a general scheme in which the acid-resistant heavy fluorous compound 1 is applied as a recyclable tag in synthetic carbohydrate chemistry.

  3. Combined effects of microwaves, electron beams and polyfunctional monomers on rubber vulcanization.

    PubMed

    Manaila, Elena; Martin, Diana; Stelescu, Daniela Zuga; Craciun, Gabriela; Ighigeanu, Daniel; Matei, Constantin

    2009-01-01

    This paper presents comparative results obtained by conventional vulcanization with benzoyl peroxide (CV-BP), separate electron beam vulcanization (EB-V) and simultaneous electron beam and microwave vulcanization (EB+MW-V) applied to two kind of rubber samples: EVA (ethylene vinyl acetate) rubber-sample (EVA-sample) and EPDM (ethylene-propylene terpolymer) rubber-sample (EPDM-sample). The EVA-samples contain 61.54% EVA Elvax 260, 30.77% carbon black, 1.85% TAC (triallylcyanurate) polyfunctional monomer and 5.84% filler (zinc oxide, stearic acid, polyethylene glycol and antioxidant). The EPDM-samples contain 61.54% EPDM Nordel 4760, 30.77% carbon black, 1.85% TMPT (trimethylopropane trimethacrylate) polyfunctional monomer and 5.84% filler (zinc oxide, stearic acid, polyethylene glycol and antioxidant). The rubber samples designed for different vulcanization methods were obtained from raw rubber mixtures, as compressed sheets of 2 mm in the polyethylene foils to minimize oxidation. For EB and EB + MW treatments the sheets were cut in rectangular shape 0.15 x 0.15 m2. The physical properties of samples obtained by CV-BP EV-Vand EB + MW-V methods were evaluated by measuring the tearing strength, residual elongation, elongation at break, tensile strength, 300% modulus, 100% modulus, elasticity and hardness. The obtained results demonstrate an improvement of rubber several properties obtained by EB and EB + MW processing as compared to classical procedure using benzoyl peroxide.

  4. Enantiomorphs of a carbene-ruthenium(II)-porphyrin complex with four 'chiral pillars'.

    PubMed

    Hirasawa, Kai; Yuge, Hidetaka; Miyamoto, Takeshi Ken

    2008-02-01

    The chiral metalloporphyrin (dibenzoylmethylene-kappaC)(ethanol-kappaO){5,10,15,20-tetrakis[(1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl]porphyrinato-kappa(4)N}ruthenium(II)-ethanol-dichloromethane (1/2/2), [Ru(C(84)H(76)N(4))(C(15)H(10)O(2))(C(2)H(6)O)].2C(2)H(6)O.2CH(2)Cl(2), and its enantiomorph were prepared from enantiomerically pure porphyrins. The enantiomers are potential versatile catalysts for asymmetric cyclopropanation, aziridination or epoxidation. In each compound, the rather large dibenzoylcarbene group is squeezed between four columnar 1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracen-9-yl groups at the meso positions resulting in a doming deformation of the porphyrin core. The dibenzoylcarbene group has an anti conformation. The benzoyl O atoms make short van der Waals contacts (< 2.6 A) with the methine groups of the chiral columnar substituents at the 10 and 20 positions of the porphyrin rings. A hydrogen-bonded supramolecular chain is formed parallel to the b axis by interactions between the benzoyl O atom and the hydroxy groups of the coordinated and uncoordinated ethanol molecules. PMID:18252997

  5. Bioevaluation of novel anti-biofilm coatings based on PVP/Fe3O4 nanostructures and 2-((4-ethylphenoxy)methyl)-N- (arylcarbamothioyl)benzamides.

    PubMed

    Limban, Carmen; Missir, Alexandru Vasile; Grumezescu, Alexandru Mihai; Oprea, Alexandra Elena; Grumezescu, Valentina; Vasile, Bogdan Stefan; Socol, Gabriel; Trușcă, Roxana; Caproiu, Miron Teodor; Chifiriuc, Mariana Carmen; Gălățeanu, Bianca; Costache, Marieta; Morușciag, Laurențiu; Pîrcălăbioru, Grațiela; Nuță, Diana Camelia

    2014-01-01

    Novel derivatives were prepared by reaction of aromatic amines with 2-(4-ethylphenoxymethyl)benzoyl isothiocyanate, affording the N-[2-(4-ethylphenoxymethyl) benzoyl]-Nꞌ-(substituted phenyl)thiourea. Structural elucidation of these compounds was performed by IR, NMR spectroscopy and elemental analysis. The new compounds were used in combination with Fe3O4 and polyvinylpyrrolidone (PVP) for the coating of medical surfaces. In our experiments, catheter pieces were coated by Matrix Assisted Pulsed Laser Evaporation (MAPLE) technique. The microbial adherence ability was investigated in 6 multi-well plates by using culture based methods. The obtained surfaces were also assessed for their cytotoxicity with respect to osteoblast cells, by using fluorescence microscopy and MTT assay. The prepared surfaces by advanced laser processing inhibited the adherence and biofilm development ability of Staphylococcus aureus and Pseudomonas aeruginosa tested strains while cytotoxic effects on the 3T3-E1 preosteoblasts embedded in layer shaped alginate hydrogels were not observed. These results suggest that the obtained medical surfaces, based on the novel thiourea derivatives and magnetic nanoparticles with a polymeric shell could represent a promising alternative for the development of new and effective anti-infective strategies. PMID:25120054

  6. A P212121 polymorph of (+)-clusianone

    PubMed Central

    Vaneesa Nagalingam, Sree; Wong Pik Ching, Janet; Khaled bin Break, Mohammed; Tahir, M. Ibrahim M.; Khoo, Teng-Jin

    2013-01-01

    The title compound, C33H42O4 [systematic name: (1S,5S,7R)-3-benzoyl-4-hy­droxy-8,8-dimethyl-1,5,7-tris­(3-methyl­but-2-­enyl)bi­cyclo­[3.3.1]nona-3-ene-2,9-dione], has a central bi­cyclo­[3.3.1]nonane-2,4,9-trione surrounded by tetra­prenyl­ated and benzoyl groups. The compound was recrystallized several times in methanol using both a slow evaporation method and with a crystal-seeding technique. This subsequently produced diffraction-quality crystals which crystallize in the ortho­rhom­bic space group P212121, in contrast to a previous report of a structure determination in the Pna21 space group [McCandlish et al. (1976 ▶). Acta Cryst. B32, 1793–1801]. The title compound has a melting point of 365–366 K, and a specific rotation [α]20 value of +51.94°. A strong intra­molecular O—H⋯O hydrogen bond is noted. In the crystal, mol­ecules are assembled in the ab plane by weak C—H⋯O inter­actions. PMID:24860292

  7. Structural studies and investigation on the activity of imidazole-derived thiosemicarbazones and hydrazones against crop-related fungi.

    PubMed

    Reis, Débora C; Despaigne, Angel A Recio; Da Silva, Jeferson G; Silva, Nayane F; Vilela, Camila F; Mendes, Isolda C; Takahashi, Jacqueline A; Beraldo, Heloisa

    2013-10-14

    New imidazole derived thiosemicarbazones and hydrazones were prepared by condensation of 4(5)-imidazole carboxaldehyde, 4-(1H-imidazole-1-yl)benzaldehyde and 4-(1H-imidazole-1-yl)acetophenone with a thiosemicarbazide or hydrazide. All compounds were characterized by quantitative elemental analysis, IR and NMR techniques. Eight structures were determined by single crystal X-ray diffraction. The antifungal activities of the compounds were evaluated. None of the compounds exhibited significant activity against Aspergillus flavus and Candida albicans, while 4(5)-imidazolecarboxaldehyde thiosemicarbazone (ImT) and 4-(1H-imidazole-1-yl)benzaldehyde thiosemicabazone (4ImBzT) were highly and selectively active against Cladosporium cladosporioides. 4(5)-Imidazolecarboxaldehyde benzoyl hydrazone (4(5)ImPh), 4(5)-imidazolecarboxaldehyde-para-chlorobenzoyl hydrazone (4(5)ImpClPh), 4(5)-imidazolecarboxaldehyde-para-nitrobenzoyl hydrazone (4(5)ImpNO2Ph), 4-(imidazole-1-yl)acetophenone-para-chloro-benzoyl hydrazone (4ImAcpClPh) and 4-(imidazole-1-yl)acetophenone-para-nitro-benzoylhydrazone (4ImAcpNO2Ph) were highly active against Candida glabrata. 4(5)ImpClPh and 4(5)ImpNO2Ph were very effective against C. cladosporioides. In many cases, activity was superior to that of the reference compound nystatin.

  8. A new potentiometric electrode incorporating functionalized β-cyclodextrins for diclofenac determination.

    PubMed

    Lenik, Joanna

    2014-12-01

    This paper reports the preparation of diclofenac-selective membrane electrodes incorporating β-cyclodextrins: (2-hydroxypropyl)-β-cyclodextrin, heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin, and heptakis(2,3,6-tri-O-benzoyl)-β-cyclodextrin. Several plasticized poly(vinyl chloride) membranes of different compositions were tested with the best electrode being the one incorporating heptakis(2,3,6-tri-O-benzoyl)-β-cyclodextrin with the membrane plasticized with 2-nitrophenyloctyl ether. The electrode is characterized by a near-Nernstian response slope of -60.0 mV decade(-1) over the linear range of 5.0×10(-5)-1.0×10(-2) mol L(-1) and a limit of detection of 1.4×10(-5) mol L(-1). The proposed electrode can easily discriminate diclofenac ions from several inorganic and organic interferents and some common drug excipients. The electrode has a response time of 10s and can be used within a pH range of 6.2-8.5 over 10 months without any considerable deterioration. The electrical properties of the membrane electrode were studied by impedance spectroscopy. The notable advantages of the diclofenac-selective electrode include its high sensitivity, selectivity, cost-effectiveness, and comfortable application in drug and urine analysis.

  9. Low-temperature depolymerization of polysiloxanes with iron catalysis.

    PubMed

    Enthaler, Stephan; Kretschmer, Robert

    2014-07-01

    The easy accessibility and high adjustability of polymers mainly accounts for the great impact of such materials on modern society. Besides this great success, an important matter is the accumulation of large amounts of end-of-life polymers, which are mainly deposited in landfills or converted by thermal recycling or down-cycling to low-quality materials. In contrast to that, the depolymerization of end-of-life polymers to monomers, which can be applied as feedstock in polymerization chemistry for high-quality polymers, is only carried out for a small fraction of waste. Polysiloxanes are extensively used in a diverse array of technological applications. Based on intrinsic properties of polymers, depolymerization is challenging and only a few high-temperature or less environment-friendly processes have been reported. In this regard, we have set up a capable low-temperature protocol for the depolymerization of poly(dimethylsiloxane) in the presence of catalytic amounts of simple iron salts in combination with different depolymerization reagents. The application of benzoyl fluoride, benzoyl chloride/potassium fluoride, or benzoic anhydride/potassium fluoride as depolymerization reagents affords difluorodimethylsilane or 1,3-difluoro-1,1,3,3-tetramethyldisilxanes as products, which are interesting building blocks for the synthesis of new polymers and allow an overall recycling of polysiloxanes.

  10. Insulin-degrading enzyme is exported via an unconventional protein secretion pathway

    PubMed Central

    Zhao, Ji; Li, Lilin; Leissring, Malcolm A

    2009-01-01

    Insulin-degrading enzyme (IDE) is a ubiquitously expressed zinc-metalloprotease that degrades several pathophysiologically significant extracellular substrates, including insulin and the amyloid β-protein (Aβ), and accumulating evidence suggests that IDE dysfunction may be operative in both type 2 diabetes mellitus and Alzheimer disease (AD). Although IDE is well known to be secreted by a variety of cell types, the underlying trafficking pathway(s) remain poorly understood. To address this topic, we investigated the effects of known inhibitors or stimulators of protein secretion on the secretion of IDE from murine hepatocytes and HeLa cells. IDE secretion was found to be unaffected by the classical secretion inhibitors brefeldin A (BFA), monensin, or nocodazole, treatments that readily inhibited the secretion of α1-antitrypsin (AAT) overexpressed in the same cells. Using a novel cell-based Aβ-degradation assay, we show further that IDE secretion was similarly unaffected by multiple stimulators of protein secretion, including glyburide and 3'-O-(4-benzoyl)benzoyl-ATP (Bz-ATP). The calcium ionophore, A23187, increased extracellular IDE activity, but only under conditions that also elicited cytotoxicity. Our results provide the first biochemical evidence that IDE export is not dependent upon the classical secretion pathway, thereby identifying IDE as a novel member of the select class of unconventionally secreted proteins. Further elucidation of the mechanisms underlying IDE secretion, which would be facilitated by the assays described herein, promises to uncover processes that might be defective in disease or manipulated for therapeutic benefit. PMID:19144176

  11. Transition metal cations extraction by ester and ketone derivatives of chromogenic azocalix[4]arenes.

    PubMed

    Ak, Metin; Taban, Deniz; Deligöz, Hasalettin

    2008-06-15

    The molecule of azocalix[n]arene is a macrocyclic used effectively in the complexation of the heavy metal pollutants (like silver and mercury). In this work, our main aim is to prepare new chromogenic azocalix[n]arene molecules to elaborate an extractant with high extractant selectivity for metal ions able to detect this type of pollutant. The solvent extraction properties of four acetyls, four methyl ketones and four benzoyls derivatives from azocalix[4]arenes which were prepared by linking 4-ethyl, 4-n-butyl, 4-acetamid anilin and 2-aminothiazol to calix[4]arene through a diazo-coupling reaction, the alkaline earth (Sr2+) and the transition (Ag+, Hg2+, Co2+, Ni2+, Cu2+, Zn2+, Cd2+, Cr3+) metal cations have been determined by extraction studies with metal picrates. Both ketones are better extractants than esters, and show a strong preference for Ag+, while Cu2+ and Cr3+ are the most extracted cation with the esters. Both acetyl and benzoyl esters are good carriers for Ag+ and Hg2+.

  12. Synthesis, Characterization, and Biological Activity of N′-[(Z)-(3-Methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide and Its Co(II), Ni(II), and Cu(II) Complexes

    PubMed Central

    Asegbeloyin, Jonnie N.; Ujam, Oguejiofo T.; Okafor, Emmanuel C.; Babahan, Ilknur; Coban, Esin Poyrazoglu; Özmen, Ali; Biyik, Halil

    2014-01-01

    Reaction of 1-phenyl-3-methyl-4-benzoyl-pyrazol-5-one and benzoyl hydrazide in refluxing ethanol gave N′-[(Z)-(3-methyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)(phenyl)methyl]benzohydrazide (HL1), which was characterized by NMR spectroscopy and single-crystal X-ray structure study. X-ray diffraction analyses of the crystals revealed a nonplanar molecule, existing in the keto-amine form, with intermolecular hydrogen bonding forming a seven-membered ring system. The reaction of HL1 with Co(II), Ni(II), and Cu(II) halides gave the corresponding complexes, which were characterized by elemental analysis, molar conductance, magnetic measurements, and infrared and electronic spectral studies. The compounds were screened for their in vitro cytotoxic activity against HL-60 human promyelocytic leukemia cells and antimicrobial activity against some bacteria and yeasts. Results showed that the compounds are potent against HL-60 cells with the IC50 value ≤5 μM, while some of the compounds were active against few studied Gram-positive bacteria. PMID:25332694

  13. Carboxy terminated rubber based on natural rubber grafted with acid anhydrides and its adhesion properties

    NASA Astrophysics Data System (ADS)

    Klinpituksa, P.; Kongkalai, P.; Kaesaman, A.

    2014-08-01

    The chemical modification of natural rubber by grafting of various polar functional molecules is an essential method, improving the versatility of rubber in applications. This research investigated the preparation of natural rubber-graft-citraconic anhydride (NR-g-CCA), natural rubber-graft-itaconic anhydride (NR-g-ICA), and natural rubber-graft-maleic anhydride (NR-g-MA), with the anhydrides grafted to natural rubber in toluene using benzoyl peroxide as an initiator. Variations of monomer content, initiator content, temperature and reaction time of the grafting copolymerization were investigated. The maximum degrees of grafting were 1.06% for NR-g-CCA, 4.66% for NR-g-ICA, and 5.03% for NR-g-MA, reached using 10 phr citraconic anhydride, 10 phr of itaconic anhydride, or 8 phr of maleic anhydride, 3 phr benzoyl peroxide, at 85, 80 and 80°C for 2, 2 and 3 hrs, respectively. Solvent-based wood adhesives were formulated from these copolymers with various contents of wood resin in the range 10-40 phr. The maximal 289 N/in cleavage peel and 245.7 KPa shear strength for NR-g-MA (5.03% grafting) were obtained at 40 phr wood resin.

  14. Metabolism of Multiple Aromatic Compounds in Corn Stover Hydrolysate by Rhodopseudomonas palustris.

    PubMed

    Austin, Samantha; Kontur, Wayne S; Ulbrich, Arne; Oshlag, J Zachary; Zhang, Weiping; Higbee, Alan; Zhang, Yaoping; Coon, Joshua J; Hodge, David B; Donohue, Timothy J; Noguera, Daniel R

    2015-07-21

    Lignocellulosic biomass hydrolysates hold great potential as a feedstock for microbial biofuel production, due to their high concentration of fermentable sugars. Present at lower concentrations are a suite of aromatic compounds that can inhibit fermentation by biofuel-producing microbes. We have developed a microbial-mediated strategy for removing these aromatic compounds, using the purple nonsulfur bacterium Rhodopseudomonas palustris. When grown photoheterotrophically in an anaerobic environment, R. palustris removes most of the aromatics from ammonia fiber expansion (AFEX) treated corn stover hydrolysate (ACSH), while leaving the sugars mostly intact. We show that R. palustris can metabolize a host of aromatic substrates in ACSH that have either been previously described as unable to support growth, such as methoxylated aromatics, and those that have not yet been tested, such as aromatic amides. Removing the aromatics from ACSH with R. palustris, allowed growth of a second microbe that could not grow in the untreated ACSH. By using defined mutants, we show that most of these aromatic compounds are metabolized by the benzoyl-CoA pathway. We also show that loss of enzymes in the benzoyl-CoA pathway prevents total degradation of the aromatics in the hydrolysate, and instead allows for biological transformation of this suite of aromatics into selected aromatic compounds potentially recoverable as an additional bioproduct.

  15. P2X7 receptor-mediated calcium dynamics in HEK293 cells: experimental characterization and modelling approach

    NASA Astrophysics Data System (ADS)

    Di Garbo, A.; Alloisio, S.; Nobile, M.

    2012-04-01

    The P2X7 receptor (P2X7R) induces ionotropic Ca2 + signalling in different cell types. It plays an important role in the immune response and in the nervous system. Here, the mechanisms underlying intracellular Ca2 + variations evoked by 3‧-O-(4-benzoyl)benzoyl-ATP (BzATP), a potent agonist of the P2X7R, in transfected HEK293 cells, are investigated both experimentally and theoretically. We propose a minimal model of P2X7R that is capable of reproducing, qualitatively and quantitatively, the experimental data. This approach was also adopted for the P2X7R variant, which lacks the entire C-terminus tail (trP2X7R). Then we introduce a biophysical model describing the Ca2 + dynamics in HEK293. Our model gives an account of the ionotropic Ca2 + influx evoked by BzATP on the basis of the kinetics model of P2X7R. To explain the complex Ca2 + responses evoked by BzATP, the model predicted that an impairment in Ca2 + extrusion flux through the plasma membrane is a key factor for Ca2 + homeostasis in HEK293 cells.

  16. An easily regenerable enzyme reactor prepared from polymerized high internal phase emulsions.

    PubMed

    Ruan, Guihua; Wu, Zhenwei; Huang, Yipeng; Wei, Meiping; Su, Rihui; Du, Fuyou

    2016-04-22

    A large-scale high-efficient enzyme reactor based on polymerized high internal phase emulsion monolith (polyHIPE) was prepared. First, a porous cross-linked polyHIPE monolith was prepared by in-situ thermal polymerization of a high internal phase emulsion containing styrene, divinylbenzene and polyglutaraldehyde. The enzyme of TPCK-Trypsin was then immobilized on the monolithic polyHIPE. The performance of the resultant enzyme reactor was assessed according to the conversion ability of Nα-benzoyl-l-arginine ethyl ester to Nα-benzoyl-l-arginine, and the protein digestibility of bovine serum albumin (BSA) and cytochrome (Cyt-C). The results showed that the prepared enzyme reactor exhibited high enzyme immobilization efficiency and fast and easy-control protein digestibility. BSA and Cyt-C could be digested in 10 min with sequence coverage of 59% and 78%, respectively. The peptides and residual protein could be easily rinsed out from reactor and the reactor could be regenerated easily with 4 M HCl without any structure destruction. Properties of multiple interconnected chambers with good permeability, fast digestion facility and easily reproducibility indicated that the polyHIPE enzyme reactor was a good selector potentially applied in proteomics and catalysis areas.

  17. An easily regenerable enzyme reactor prepared from polymerized high internal phase emulsions.

    PubMed

    Ruan, Guihua; Wu, Zhenwei; Huang, Yipeng; Wei, Meiping; Su, Rihui; Du, Fuyou

    2016-04-22

    A large-scale high-efficient enzyme reactor based on polymerized high internal phase emulsion monolith (polyHIPE) was prepared. First, a porous cross-linked polyHIPE monolith was prepared by in-situ thermal polymerization of a high internal phase emulsion containing styrene, divinylbenzene and polyglutaraldehyde. The enzyme of TPCK-Trypsin was then immobilized on the monolithic polyHIPE. The performance of the resultant enzyme reactor was assessed according to the conversion ability of Nα-benzoyl-l-arginine ethyl ester to Nα-benzoyl-l-arginine, and the protein digestibility of bovine serum albumin (BSA) and cytochrome (Cyt-C). The results showed that the prepared enzyme reactor exhibited high enzyme immobilization efficiency and fast and easy-control protein digestibility. BSA and Cyt-C could be digested in 10 min with sequence coverage of 59% and 78%, respectively. The peptides and residual protein could be easily rinsed out from reactor and the reactor could be regenerated easily with 4 M HCl without any structure destruction. Properties of multiple interconnected chambers with good permeability, fast digestion facility and easily reproducibility indicated that the polyHIPE enzyme reactor was a good selector potentially applied in proteomics and catalysis areas. PMID:26995089

  18. Chemistry of the sternal gland secretion of the Mediterranean centipede Himantarium gabrielis (Linnaeus, 1767) (Chilopoda: Geophilomorpha: Himantariidae).

    PubMed

    Vujisić, Ljubodrag V; Vučković, Ivan M; Makarov, Slobodan E; Ilić, Bojan S; Antić, Dragan Z; Jadranin, Milka B; Todorović, Nina M; Mrkić, Ivan V; Vajs, Vlatka E; Lučić, Luka R; Curčić, Božidar P M; Mitić, Bojan M

    2013-09-01

    The geophilomorph centipede, Himantarium gabrielis, when disturbed, discharges a viscous and proteinaceous secretion from the sternal glands. This exudate was found by gas chromatography-mass spectrometry, liquid chromatography-high resolution mass spectrometry, liquid chromatography-mass spectrometry-mass spectrometry and NMR analyses to be composed of hydrogen cyanide, benzaldehyde, benzoyl nitrile, benzyl nitrile, mandelonitrile, mandelonitrile benzoate, 3,7,6O-trimethylguanine (himantarine), farnesyl 2,3-dihydrofarnesoate and farnesyl farnesoate. This is the first report on the presence of benzyl nitrile and mandelonitrile benzoate in secreted substances from centipedes. Farnesyl 2,3-dihydrofarnesoate is a new compound, while himantarine and farnesyl farnesoate were not known as natural products. A post-secretion release of hydrogen cyanide by reaction of mandelonitrile and benzoyl nitrile was observed by NMR, and hydrogen cyanide signals were completely assigned. In addition, a protein component of the secretion was analysed by electrophoresis which revealed the presence of a major 55 kDa protein. Analyses of the defensive exudates of other geophilomorph families should produce further chemical surprises. PMID:23907296

  19. Studies on the beef heart mitochondrial F/sub 1/-ATPase with the photoaffinity label BzATP

    SciTech Connect

    Ackerman, S.H.

    1987-01-01

    The photoaffinity analog of ATP, 3'-O-(4-benzoyl) benzoyl ATP (BzATP), was used in kinetics and binding studies to investigate the mechanism of the beef heart mitochondrial F/sup 1/-ATPase. New methods were developed for the synthesis and purification of non-radioactive BzATP, /sup 3/H-BzATP, and ..gamma..-/sup 32/P-BzATP, and the molar absorption coefficient for BzATP was determined. Experimental conditions for photolysis and binding studies were defined in which the stability of both BzATP and F/sub 1/ was maintained. Initial experiments examined the kinetic interactions between F/sub 1/ and BzATP. In the absence of actinic illumination, BzATP was a slow substrate for the enzyme and behaved as a classical competitive inhibitor versus ATP. Under photolytic conditions, BzATP inactivated F/sub 1/ with pseudo first-order kinetics, and the photoinactivation reaction showed rate saturation suggesting specific, reversible binding of BzATP to F/sub 1/ prior to covalent bond formation. ATP protected against F/sub 1/ photoinactivation and F/sub 1/ preparations partially modified covalently yielded the same K/sub m/ for ATP as unmodified enzyme preparations. These results strongly suggested that BzATP was bound to catalytic sites on the enzyme.

  20. Synthesis, Thermal Properties and Cytotoxicity Evaluation of Hydrocarbon and Fluorocarbon Alkyl β-D-xylopyranoside Surfactants

    PubMed Central

    Xu, Wenjin; Osei-Prempeh, Gifty; Lema Herrera, Fresia C.; Oldham, E. Davis; Aguilera, Renato J.; Parkin, Sean; Rankin, Stephen E.; Knutson, Barbara L.; Lehmler, Hans-Joachim

    2011-01-01

    Alkyl β-D-xylopyranosides are highly surface active, biodegradable surfactants that can be prepared from hemicelluloses and are of interest for use as pharmaceuticals, detergents, agrochemicals and personal care products. To gain further insights into their structure-property and structure-activity relationships, the present study synthesized a series of hydrocarbon (-C6H13 to -C16H33) and fluorocarbon (-(CH2)2C6F13) alkyl β-D-xylopyranosides in four steps from D-xylose by acylation or benzoylation, bromination, Koenigs-Knorr reaction and hydrolysis, with the benzoyl protecting group giving better yields compared to the acyl group in the Koenigs-Knorr reaction. All alkyl β-D-xylopyranosides formed thermotropic liquid crystals. The phase transition of the solid crystalline phase to a liquid crystalline phase increased linearly with the length of the hydrophobic tail. The clearing points were near constant for alkyl β-D-xylopyranosides with a hydrophobic tail ≥ 8, but occurred at a significantly lower temperature for hexyl β-D-xylopyranoside. Short and long-chain alkyl β-D-xylopyranosides displayed no cytotoxicity at concentration below their aqueous solubility limit. Hydrocarbon and fluorocarbon alkyl β-D-xylopyranosides with intermediate chain length displayed some toxicity at millimolar concentrations due to apoptosis. PMID:22207000

  1. Mechanisms of quinacrine binding and fluorescence in nuclei and chromosomes.

    PubMed

    Sumner, A T

    1986-01-01

    The mechanisms has been investigated whereby quinacrine binds to the DNA of nuclei and chromosomes in cytological preparations fixed in methanol-acetic acid. A variety of evidence is consistent with the idea that the quinacrine binds by intercalation. This is supported by a high value for the affinity of quinacrine for DNA, together with a saturation value of 0.2 quinacrine molecules/nucleotide; binding in the presence of strong salt solutions; and inhibition of fluorescence and banding by denaturation or depurination of DNA. At high quinacrine concentrations, weak binding of quinacrine to nuclei and chromosomes also occurs, but this is not relevant to the production of strong fluorescence or Q-banding patterns. A number of factors were tested which might have affected quinacrine fluorescence and banding. These included: pH; blocking protein amino groups by acetylation or benzoylation; introduction of hydrophobic groups by benzoylation; and dephosphorylation. All these treatments were without effect. However, comparison of the quinacrine fluorescence of human and onion nuclei, which differ substantially in the base composition of their DNA, shows that quinacrine fluorescence can be enhanced in cytological preparations by AT-rich DNA. PMID:3721920

  2. Structural comparison of complexes of methotrexate analogues with Lactobacillus casei dihydrofolate reductase by two-dimensional /sup 1/H NMR at 500 MHz

    SciTech Connect

    Hammond, S.J.; Birdsall, B.; Feeney, J.; Searle, M.S.; Roberts, G.C.K.; Cheung, H.T.A.

    1987-12-29

    The authors have used two-dimensional (2D) NMR methods to examine complexes of Lactobacillus casei dihydrofolate reductase and methotrexate (MTX) analogues having structural modifications of the benzoyl ring and also the glutamic acid moiety. Assignments of the /sup 1/H signals in the spectra of the various complexes were made by comparison of their 2D spectra with those complexes containing methotrexate where we have previously assigned resonances from 32 of the 162 amino acid residues. In the complexes formed with the dihalomethotrexate analogues, the glutamic acid and pteridine ring moieties were shown to bind to the enzyme in a manner similar to that found in the methotrexate-enzyme complex. Perturbations in /sup 1/H chemical shifts of protons in Phe-49, Leu-54, and Leu-27 and the methotrexate H7 and NMe protons were observed in the different complexes and were accounted for by changes in orientation of the benzoyl ring in the various complexes. Binding of oxidized or reduced coenzyme to the binary complexes did not result in different shifts for Leu-27, Leu-54, or Leu-19 protons, and thus, the orientation of the benzoyl ring of the methotrexate analogues is not perturbed greatly by the presence of either oxidized or reduced coenzyme. In the complex with the ..gamma..-monoamide analog, the /sup 1/H signals of assigned residues in the protein had almost identical shifts with the corresponding protons in the methotrexate-enzyme complex for all residues except His-28 and, to a lesser extent, Leu-27. This indicates that while the His-28 interaction with the MTX ..gamma..-CO/sub 2//sup -/ is no longer present in this complex with the ..gamma..-amide, there has not been a major change in the overall structure of the two complexes. This behavior contrasts to that of the ..cap alpha..-amide complex where /sup 1/H signals from protons in several amino acid residues are different compared with their values in the complex formed with methotrexate.

  3. Characterization of an endoprotease from rat small intestinal mucosal secretory granules which generates somatostatin-28 from prosomatostatin by cleavage after a single arginine residue.

    PubMed

    Beinfeld, M C; Bourdais, J; Kuks, P; Morel, A; Cohen, P

    1989-03-15

    We have extracted, characterized, and partially purified an enzyme from secretory granules from rat small intestinal mucosa which cleaves a synthetic prosomatostatin substrate on the carboxyl side of a single arginine residue. This substrate Leu-Gln-Arg-Ser-Ala-Asn-Ser-NH2 contains the monobasic site at which mammalian prosomatostatin is cleaved in vivo to generate somatostatin-28. This activity was released from the granules by osmotic shock followed by extraction with 500 mM KCl. The enzyme had a molecular weight of about 55,000, a pH optimum of about 7.5, and a Km for the synthetic substrate of 20 microM. It was partially inhibited by diisopropyl fluorophosphate, phenylmethanesulfonyl fluoride, iodoacetate, soybean trypsin inhibitor, and EDTA. It was also very sensitive to aprotinin (complete inhibition at 25 micrograms/ml) but was not inhibited by bestatin, pepstatin, or p-chloromercuribenzoate. This endoprotease was unable to cleave three small trypsin and kallikrein substrates (N alpha-benzoyl-L-arginine ethyl ester, N alpha-benzoyl-DL-arginine p-nitroanilide, and N alpha-benzoyl-L-arginine 7-amido-4-methylcoumarin). It was unable to cleave either the Arg-Asp bond in CCK 12 or the Arg-Glu and Arg-Met bonds of synthetic peptides corresponding to sequences of anglerfish prosomatostatin II situated upstream from the somatostatin-28 domain. These observations together suggest that adjacent amino acids play a role in determining the conformational specificity of the monobasic cleavage. This soluble enzyme was also able to cleave three synthetic substrates containing dibasic residues (Arg-Lys or Lys-Arg) on the carboxyl side of the arginine, although it did so less rapidly than at the monobasic cleavage sites. When incubated with partially purified prosomatostatin from anglerfish pancreas, significant quantities of somatostatin-28 II were produced. All these cleavages were completely blocked by preincubation with aprotinin. Although further work is required to

  4. Water-soluble nitric-oxide-releasing acetylsalicylic acid (ASA) prodrugs.

    PubMed

    Rolando, Barbara; Lazzarato, Loretta; Donnola, Monica; Marini, Elisabetta; Joseph, Sony; Morini, Giuseppina; Pozzoli, Cristina; Fruttero, Roberta; Gasco, Alberto

    2013-07-01

    A series of water-soluble (benzoyloxy)methyl esters of acetylsalicylic acid (ASA), commonly known as aspirin, are described. The new derivatives each have alkyl chains containing a nitric oxide (NO)-releasing nitrooxy group and a solubilizing moiety bonded to the benzoyl ring. The compounds were synthesized and evaluated as ASA prodrugs. After conversion to the appropriate salt, most of the derivatives are solid at room temperature and all possess good water solubility. They are quite stable in acid solution (pH 1) and less stable at physiological pH. In human serum, these compounds are immediately metabolized by esterases, producing a mixture of ASA, salicylic acid (SA), and of the related NO-donor benzoic acids, along with other minor products. Due to ASA release, the prodrugs are capable of inhibiting collagen-induced platelet aggregation of human platelet-rich plasma. Simple NO-donor benzoic acids 3-hydroxy-4-(3-nitrooxypropoxy)benzoic acid (28) and 3-(morpholin-4-ylmethyl)-4-[3-(nitrooxy)propoxy]benzoic acid (48) were also studied as representative models of the whole class of benzoic acids formed following metabolism of the prodrugs in serum. These simplified derivatives did not trigger antiaggregatory activity when tested at 300 μM. Only 28 displays quite potent NO-dependent vasodilatatory action. Further in vivo evaluation of two selected prodrugs, {[2-(acetyloxy)benzoyl]oxy}methyl-3-[(3-[aminopropanoyl)oxy]-4-[3-(nitrooxy)propoxy]benzoate⋅HCl (38) and {[2-(acetyloxy)benzoyl]oxy}methyl 3-(morpholin-4-ylmethyl)-4-[3-(nitrooxy)propoxy]benzoate oxalate (49), revealed that their anti-inflammatory activities are similar to that of ASA when tested in the carrageenan-induced paw edema assay in rats. The gastrotoxicity of the two prodrugs was also determined to be lower than that of ASA in a lesion model in rats. Taken together, these results indicated that these NO-donor ASA prodrugs warrant further investigation for clinical application.

  5. Divergence of Substrate Specificity and Function in the Escherichia coli Hotdog-fold Thioesterase Paralogs YdiI and YbdB

    PubMed Central

    2015-01-01

    The work described in this paper, and its companion paper (Wu, R., Latham, J. A., Chen, D., Farelli, J., Zhao, H., Matthews, K. Allen, K. N., and Dunaway-Mariano, D. (2014) Structure and Catalysis in the Escherichia coli Hotdog-fold Thioesterase Paralogs YdiI and YbdB. Biochemistry, DOI: 10.1021/bi500334v), focuses on the evolution of a pair of paralogous hotdog-fold superfamily thioesterases of E. coli, YbdB and YdiI, which share a high level of sequence identity but perform different biological functions (viz., proofreader of 2,3-dihydroxybenzoyl-holoEntB in the enterobactin biosynthetic pathway and catalyst of the 1,4-dihydoxynapthoyl-CoA hydrolysis step in the menaquinone biosynthetic pathway, respectively). In vitro substrate activity screening of a library of thioester metabolites showed that YbdB displays high activity with benzoyl-holoEntB and benzoyl-CoA substrates, marginal activity with acyl-CoA thioesters, and no activity with 1,4-dihydoxynapthoyl-CoA. YdiI, on the other hand, showed a high level of activity with its physiological substrate, significant activity toward a wide range of acyl-CoA thioesters, and minimal activity toward benzoyl-holoEntB. These results were interpreted as evidence for substrate promiscuity that facilitates YbdB and YdiI evolvability, and divergence in substrate preference, which correlates with their assumed biological function. YdiI support of the menaquinone biosynthetic pathway was confirmed by demonstrating reduced anaerobic growth of the E. coliydiI-knockout mutant (vs wild-type E. coli) on glucose in the presence of the electron acceptor fumarate. Bioinformatic analysis revealed that a small biological range exists for YbdB orthologs (i.e., limited to Enterobacteriales) relative to that of YdiI orthologs. The divergence in YbdB and YdiI substrate specificity detailed in this paper set the stage for their structural analyses reported in the companion paper. PMID:24992697

  6. Influence of bleaching on flavor of 34% whey protein concentrate and residual benzoic acid concentration in dried whey proteins.

    PubMed

    Listiyani, M A D; Campbell, R E; Miracle, R E; Dean, L O; Drake, M A

    2011-09-01

    Previous studies have shown that bleaching negatively affects the flavor of 70% whey protein concentrate (WPC70), but bleaching effects on lower-protein products have not been established. Benzoyl peroxide (BP), a whey bleaching agent, degrades to benzoic acid (BA) and may elevate BA concentrations in dried whey products. No legal limit exists in the United States for BP use in whey, but international concerns exist. The objectives of this study were to determine the effect of hydrogen peroxide (HP) or BP bleaching on the flavor of 34% WPC (WPC34) and to evaluate residual BA in commercial and experimental WPC bleached with and without BP. Cheddar whey was manufactured in duplicate. Pasteurized fat-separated whey was subjected to hot bleaching with either HP at 500 mg/kg, BP at 50 or 100 mg/kg, or no bleach. Whey was ultrafiltered and spray dried into WPC34. Color [L*(lightness), a* (red-green), and b* (yellow-blue)] measurements and norbixin extractions were conducted to compare bleaching efficacy. Descriptive sensory and instrumental volatile analyses were used to evaluate bleaching effects on flavor. Benzoic acid was extracted from experimental and commercial WPC34 and 80% WPC (WPC80) and quantified by HPLC. The b* value and norbixin concentration of BP-bleached WPC34 were lower than HP-bleached and control WPC34. Hydrogen peroxide-bleached WPC34 displayed higher cardboard flavor and had higher volatile lipid oxidation products than BP-bleached or control WPC34. Benzoyl peroxide-bleached WPC34 had higher BA concentrations than unbleached and HP-bleached WPC34 and BA concentrations were also higher in BP-bleached WPC80 compared with unbleached and HP-bleached WPC80, with smaller differences than those observed in WPC34. Benzoic acid extraction from permeate showed that WPC80 permeate contained more BA than did WPC34 permeate. Benzoyl peroxide is more effective in color removal of whey and results in fewer flavor side effects compared with HP and residual BA is

  7. Protein Targets of Reactive Metabolites of Thiobenzamide in Rat Liver In Vivo

    PubMed Central

    Ikehata, Keisuke; Duzhak, Tatyana G.; Galeva, Nadezhda A.; Ji, Tao; Koen, Yakov M.; Hanzlik, Robert P.

    2008-01-01

    Thiobenzamide (TB) is a potent hepatotoxin in rats, causing dose-dependent hyperbilirubinemia, steatosis, and centrolobular necrosis. These effects arise subsequent to and appear to result from the covalent binding of the iminosulfinic acid metabolite of TB to cellular proteins and phosphatidylethanolamine lipids (Ji, et al., Chem. Res. Toxicol. 2007, 20, 701−708). To understand better the relationship between the protein covalent binding and toxicity of TB we investigated the chemistry of the adduction process and the identity of the target proteins. Cytosolic and microsomal proteins isolated from the livers of rats treated with a hepatotoxic dose of [carboxyl−14C]-TB contained high levels of covalently bound radioactivity (25.6 and 36.8 nmol eq./mg protein, respectively). These proteins were fractionated by 2-dimensional gel electrophoresis, and radioactive spots (154 cytosolic and 118 microsomal) were located by phosphorimaging. Corresponding spots from animals treated with a 1:1 mixture of TB and TB-d5 were similarly separated, the spots were excised, and the proteins were digested in-gel with trypsin. Peptide mass mapping identified 42 cytosolic and 24 microsomal proteins, many of which appeared in more than one spot on the gel; however, only a few spots contained more than one identifiable protein. Eighty six peptides carrying either a benzoyl- or a benzimidoyl adduct on a lysine side chain were clearly recognized by their d0/d5 isotopic signature (sometimes both in the same digest). Because model studies showed that benzoyl adducts do not arise by hydrolysis of benzimidoyl adducts, it was proposed that TB undergoes S-oxidation twice to form iminosulfonic 4 (PhC(=NH)SO2H) which either benzimidoylates a lysine side chain or undergoes hydrolysis to 9 (PhC(=O)SO2H) and then benzoylates a lysine side chain. The proteins modified by TB metabolites serve a range of biological functions and form a set that overlaps partly with the sets of proteins known to be

  8. Crystal packing in three related disaccharides: precursors to heparan sulfate oligosaccharides

    PubMed Central

    Gainsford, Graeme J.; Schwörer, Ralf; Tyler, Peter C.; Zubkova, Olga V.

    2015-01-01

    The three title compounds form part of a set of important precursor dissacharides which lead to novel therapeutics, in particular for Alzheimer’s disease. All three crystallize as poorly diffracting crystals with one independent mol­ecule in the asymmetric unit. Two of them are isostructural: 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-de­oxy-4-O-(9-fluor­en­yl­methyl­oxycarbon­yl)-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-chloro­acetyl-α-l-ido­pyran­oside, C59H56ClN3O16, (I), the ido-relative of a reported gluco-disaccharide [Gainsford et al., 2013 ▸). Acta Cryst. C69, 679–682] and 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-de­oxy-4-O-(9-fluorenyl­methyl­oxycarbon­yl)-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-meth­oxy­acetyl-α-l-ido­pyran­oside, C60H59N3O17, (II). Both exhibit similar conformational disorder of pendant groups. The third compound 4-meth­oxy­phenyl 4-O-[6-O-acetyl-2-azido-3,4-di-O-benzyl-2-de­oxy-α-d-gluco­pyranos­yl]-2-O-benzoyl-3-O-benzyl-6-O-meth­oxy­oacetyl-β-d-gluco­pyran­oside, C52H55N3O15, (III), illustrates that a slightly larger set of weak inter­molecular inter­actions can result in a less disordered mol­ecular arrangement. The mol­ecules are bound by weak C—H⋯O(ether) hydrogen bonds in (I) and (II), augmented by C—H⋯π inter­actions in (III). The absolute configurations were determined, although at varying levels of significance from the limited observed data. PMID:26090127

  9. An update on the management of acne vulgaris

    PubMed Central

    Keri, Jonette; Shiman, Michael

    2009-01-01

    Acne vulgaris is a common skin disorder that can affect individuals from childhood to adulthood, most often occurring in the teenage years. Acne can have a significant physical, emotional, and social impact on an individual. Many different treatment options are available for the treatment of acne vulgaris. Commonly used topical treatments include benzoyl peroxide, antibiotics, sulfur and sodium sulfacetamide, azelaic acid, and retinoids. Systemic treatment is frequently used and includes the use of systemic antibiotics, oral contraceptives, antiandrogens, and retinoids. Other treatment modalities exist such as the use of superficial chemical peels as well as using laser and light devices for the treatment of acne. With the multitude of treatment options and the rapidly expanding newer technologies available to clinicians, it is important to review and be aware of the current literature and studies regarding the treatment of acne vulgaris. PMID:21436973

  10. Polyimides with improved compression moldability

    NASA Technical Reports Server (NTRS)

    Hergenrother, Paul M. (Inventor); Havens, Stephen J. (Inventor); Beltz, Mark W. (Inventor)

    1993-01-01

    The semicrystalline polyimide prepared by reaction of 3,3',4,4' benzophenonetetracarboxylic (BTDA) and 1,3-bis(4-aminophenoxy 4' benzoyl) benzene (1,3-BABB) is modified so that it can be more readily processed to form adhesive bonds, moldings, and composites. The stoichiometric ratio of the two monomers, BTDA and 1,3-BABB is controlled so that the intermediate polyamide acid is of a calculated molecular weight. A polyimide acid with excess anhydride groups is then reacted with the stoichiometrically required amount of monofunctional aromatic or aliphatic amine required for complete endcapping. The stoichiometrically offset, encapped polyimide is processed at lower temperatures and pressures than the unmodified high molecular weight polyimide with the same repeat unit, and exhibits an improved melt stability.

  11. Validated high performance thin layer chromatographic method for simultaneous quantification of major iridoids in Vitex trifolia and their antioxidant studies.

    PubMed

    Tiwari, Neerja; Luqman, Suaib; Masood, Nusrat; Gupta, Madan M

    2012-03-01

    Negundoside (1), agnuside (2) and 6'-p-hydroxy benzoyl mussaenosidic acid (3) are known bioactive metabolites in Vitex trifolia. In the present study a simple precise and reproducible method was developed for simultaneous quantitation of NS (1), AS (2) and HMA (3) and the antioxidant capacity of above markers has also been determined. Marker compounds have been resolved using silica gel 60 F(254) plates, petroleum ether (60-80)/toluene/acetone/water (10:10:80:2 v/v/v/v) as the mobile phases. The method does not employ any derivatisation procedure and can be used as a quality control tool for routine analysis of drugs V. trifolia and V. negundo together with their commercial extracts. NS (1), AS (2) and HMA (3) showed significant activity in DPPH and NO radical scavenging assays.

  12. Crystal structure of N′-[bis­(ethyl­sulfan­yl)methyl­idene]-2-hy­droxy-4-meth­oxy­benzohydrazide

    PubMed Central

    Nath, Paras; Bharty, Manoj K.; Chaurasia, Rahul; Kumari, Sanyucta; Gupta, Sushil K.

    2015-01-01

    In the title compound, C13H18N2O3S2, the amide group is in the plane of the ­benzoyl ring with a C—N—N—C torsion angle of 177.63 (12)°. The two di­thio­ate groups are in an anti conformation [torsion angles = 173.68 (8) and −9.98 (10)°]. An intra­molecular N—H⋯O hydrogen bond is observed. In the crystal, an O—H⋯O hydrogen bond and a weak C—H⋯O contact involving the same acceptor atom generate an S(6) ring motif and give rise to chains along [010]. PMID:26870554

  13. Synthesis and characterization of a sphere-like modified chitosan and acrylate resin composite for organics absorbency

    NASA Astrophysics Data System (ADS)

    Xin, S. S.; Wang, Y. H.; Li, Q. R.; Zhang, Q.; Wang, X. P.

    2015-07-01

    In this study, the chitosan (deacetylation degree >95%) was modified with vinyltriethoxysilane (A151) and became hydrophobic. The modified chitosan and acrylate resin composite can be synthesized by butyl methacrylate (BMA), butyl acrylate (BA), poly vinyl alcoho(PVA), N,N’-methylene bisacrylamide (MBA), benzoyl peroxide (BPO), and ethyl acetate under microwave irradiation. The optimal synthetic condition was as follows: the molar ratio of BA and BMA was 1.5:1, the dosage of ethyl acetate, PVA, MBA, BPO and modified chitosan were 50 wt.%, 10 wt.%, 1.5 wt.%, 2.0 wt.% and 1.0 wt.% of monomers, respectively. The adsorption capacity of the composite for CHCl3 and CCl4 were approximate to 53 g/g and 44 g/g, respectively. The organics absorbency and regeneration of the samples were also tested, and the samples were characterized by analysis of the scanning electron microscope and simultaneous thermo gravimetric/differential thermal.

  14. (Z)-Ethyl 3-(4-chloro­phen­yl)-2-cyano-3-(2,6-difluoro­benzamido)acrylate

    PubMed Central

    Dehua, Zhang; Xiaoyan, Zhang

    2008-01-01

    The title compound, C19H13ClF2N2O3, was prepared by the reaction of (Z)-ethyl 3-amino-3-(4-chloro­phen­yl)-2-cyano­acrylate and 2,6-difluoro­benzoyl chloride. The dihedral angle between the chloro­benzene and fluoro­benzene rings is 37.0 (1)°. The ethyl group is disordered over two positions [occupancies = 0.52 (2):0.48 (2)]. In addition to intra­molecular N—H⋯O and N—H⋯F hydrogen bonds, the crystal packing shows the mol­ecules to be connected by inter­molecular C—H⋯O and C—H⋯N hydrogen bonds. PMID:21581235

  15. Cocaine metabolism: cocaine and norcocaine hydrolysis by liver and serum esterases.

    PubMed

    Stewart, D J; Inaba, T; Lucassen, M; Kalow, W

    1979-04-01

    The hydrolysis of cocaine and its N-demethylated product, norcocaine, by esterases was examined in liver and serum. Both liver and serum enzymatically formed ecgonine methyl ester from cocaine. The liver enzyme had a much lower affinity for cocaine than that of serum, indicating that a different form of esterase was present in liver. The liver enzyme had a similar affinity for both norcocaine and cocaine. Likewise, the serum enzyme showed similar affinities for both substrates. The Vmax estimates, however, were consistently higher for norcocaine than cocaine in both liver and serum. Benzoyl ecgonine, a major metabolite of cocaine formed by hydrolysis, was not produced enzymatically in either serum or liver; the rate of spontaneous formation at physiological pH suggests that this metabolite may arise nonenzymatically in the body.

  16. Antibiotic resistance to Propionobacterium acnes: worldwide scenario, diagnosis and management.

    PubMed

    Sardana, Kabir; Gupta, Tanvi; Garg, Vijay K; Ghunawat, Sneha

    2015-07-01

    Antibiotic resistance in cutaneous Propionobacterium is a global problem. As a general rule, resistance levels are high to macrolides, trimethoprim/sulfamethoxazole and clindamycin, while tetracyclines and levofloxacin have low resistance potential. Newer preparations like doxycycline MR and doxycycline 20 mg are subantimicrobial and may not lead to resistance. Sampling techniques are crucial to determine resistance. Genomic evaluation using 16S ribosomal RNA gene sequencing can be useful in diagnosing mutations and mapping phylotypes of Propionobacterium acnes. Resistance may lead to slow response and relapses. Apart from benzoyl peroxide, azelaic acid, topical dapsone, oral zinc and retinoids, novel molecules with little resistance potential include octadecenedioic acid, phytosphingosine, lauric acid, retapamulin, resveratrol, T-3912 and NB-003. The use of oral retinoids and non-antibiotics like zinc can prevent resistance and help reduce the dependence on antibiotics.

  17. Differential scanning calorimetric study of acrylic resin powders used in dentistry.

    PubMed

    Ohyama, A; Imai, Y

    2000-12-01

    The thermal behavior of eight dental acrylic resin powders was studied using differential scanning calorimetry (DSC). In addition, high performance liquid chromatography was performed to supplement the DSC analysis. The HPLC analysis revealed that the contents of residual monomers and benzoyl peroxide (BPO) in the powders were 0.01-0.97 mass% and 0.25-1.28 mass%, respectively. All the resin powders produced one broad exothermic peak, while a mixture of BPO and PMMA powders generated two peaks. One peak pattern was assigned to the decomposition of BPO included within the polymer particles. The results suggested that BPO was present inside the particles and little BPO was mixed into the resin powders. Moreover, the present study demonstrated a unique useability of DSC in characterizing resin powders.

  18. Identification and optimization of anthranilic sulfonamides as novel, selective cholecystokinin-2 receptor antagonists.

    PubMed

    Allison, Brett D; Phuong, Victor K; McAtee, Laura C; Rosen, Mark; Morton, Magda; Prendergast, Clodagh; Barrett, Terry; Lagaud, Guy; Freedman, Jamie; Li, Lina; Wu, Xiaodong; Venkatesan, Hariharan; Pippel, Marna; Woods, Craig; Rizzolio, Michèle C; Hack, Michael; Hoey, Kenway; Deng, Xiaohu; King, Christopher; Shankley, Nigel P; Rabinowitz, Michael H

    2006-10-19

    A high throughput screening approach to the identification of selective cholecystokinin-2 receptor (CCK-2R) ligands resulted in the discovery of a novel series of antagonists, represented by 1-[2-[(2,1,3-benzothiadiazol-4-ylsulfonyl)amino]-5-chlorobenzoyl]-piperidine (1; CCK-2R, pK(I) = 6.4). Preliminary exploration of the structure-activity relationships around the anthranilic ring and the amide and sulfonamide moieties led to a nearly 50-fold improvement of receptor affinity and showed a greater than 1000-fold selectivity over the related cholecystokinin-1 receptor. Pharmacokinetic evaluation led to the identification of 4-[4-iodo-2-[(5-quinoxalinylsulfonyl)amino]benzoyl]-morpholine, 26d, a compound that demonstrates promising pharmacokinetic properties in the rat and dog with respect to plasma clearance and oral bioavailability and is a potent inhibitor in vivo of pentagastrin-stimulated acid secretion in the rat when dosed orally.

  19. Communal microaerophilic-aerobic biodegradation of Amaranth by novel NAR-2 bacterial consortium.

    PubMed

    Chan, Giek Far; Rashid, Noor Aini Abdul; Chua, Lee Suan; Ab llah, Norzarini; Nasiri, Rozita; Ikubar, Mohamed Roslan Mohamad

    2012-02-01

    A novel bacterial consortium, NAR-2 which consists of Citrobacter freundii A1, Enterococcus casseliflavus C1 and Enterobacter cloacae L17 was investigated for biodegradation of Amaranth azo dye under sequential microaerophilic-aerobic condition. The NAR-2 bacterial consortium with E. casseliflavus C1 as the dominant strain enhanced the decolorization process resulting in reduction of Amaranth in 30 min. Further aerobic biodegradation, which was dominated by C. freundii A1 and E. cloacae L17, allowed biotransformation of azo reduction intermediates and mineralization via metabolic pathways including benzoyl-CoA, protocatechuate, salicylate, gentisate, catechol and cinnamic acid. The presence of autoxidation products which could be metabolized to 2-oxopentenoate was elucidated. The biodegradation mechanism of Amaranth by NAR-2 bacterial consortium was predicted to follow the steps of azo reduction, deamination, desulfonation and aromatic ring cleavage. This is for the first time the comprehensive microaerophilic-aerobic biotransformation pathways of Amaranth dye intermediates by bacterial consortium are being proposed.

  20. Clinical Effects of Topical Tacrolimus on Fox-Fordyce Disease

    PubMed Central

    Kaya Erdoğan, Hilal; Bulur, Işıl; Kaya, Zeliha

    2015-01-01

    Fox-Fordyce Disease (FFD) is a rare, chronic, pruritic, inflammatory disorder of apocrine glands. It is characterized by dome-shaped, firm, discrete, skin-colored, and monomorphic perifollicular papules. The most common sites of involvement are axillae and anogenital and periareolar regions which are rich in apocrine sweat glands. Treatment is difficult. Topical, intralesional steroids, topical tretinoin, adapalene, clindamycin, benzoyl peroxide, oral contraceptives, isotretinoin, phototherapy, electrocauterisation, excision-liposuction and curettage, and fractional carbon dioxide laser are among the treatment options. In the literature, there are articles reporting beneficial effects of pimecrolimus in FFD. Nevertheless, there have not been any reports about the use of tacrolimus in FFD. We report two patients diagnosed with FFD by clinical and histopathologic examination and discussed therapeutic effects of topical tacrolimus on FFD in the light of literature. PMID:26171257

  1. Ferrocenyl Paclitaxel and Docetaxel Derivatives: Impact of an Organometallic Moiety on the Mode of Action of Taxanes.

    PubMed

    Wieczorek, Anna; Błauż, Andrzej; Żal, Aleksandra; Arabshahi, Homayon John; Reynisson, Jóhannes; Hartinger, Christian G; Rychlik, Błażej; Plażuk, Damian

    2016-08-01

    A series of ferrocenyl analogues and derivatives of paclitaxel and docetaxel were synthesised and assayed for their antiproliferative/cytotoxic effects, impact on the cell cycle distribution and ability to induce tubulin polymerisation. The replacement of the 3'-N-benzoyl group of paclitaxel with a ferrocenoyl moiety, in particular, led to formation of an analogue that was at least one order of magnitude more potent in terms of antiproliferative activity than the parent compound (IC50 values of 0.11 versus 1.11 μm, respectively), but still preserved the classical taxane mode of action, that is, microtubule stabilisation leading to mitotic arrest. Molecular docking studies revealed an unexpected binding pocket in the tubulin structure for the ferrocenoyl group introduced in the paclitaxel backbone.

  2. Novel antimicrobial organic thermal stabilizer and co-stabilizer for rigid PVC.

    PubMed

    Fahmy, Mona M; Mohamed, Riham R; Mohamed, Nadia A

    2012-01-01

    Biologically active N-benzoyl-4-(N-maleimido)-phenylhydrazide (BMPH) was synthesized and its structure was confirmed by elemental analysis and various spectral tools. It was examined as a thermal stabilizer and co-stabilizer for rigid poly (vinyl chloride) at 180 °C in air. Blending BMPH with reference samples in different ratios greatly lengthens the thermal stability value and improves the extent of discoloration of PVC. TGA confirmed the improved stability of PVC in presence of the investigated organic stabilizer. GPC measurements were done to investigate the changes occurred in the molecular masses of the degraded samples of blank PVC and PVC in presence of the novel stabilizer. BMPH showed good antimicrobial activity towards two kinds of bacteria and two kinds of fungi. PMID:22751259

  3. Use of the vapor permeable membrane for cutaneous ulcers: details of application and side effects.

    PubMed

    Alper, J C; Welch, E A; Maguire, P

    1984-11-01

    Vapor permeable membranes (VPM) are commonly being used to treat cutaneous wounds where partial or full thickness skin is lost. Five years of experience with one particular VPM has taught a great deal concerning its proper use. Correct preparation of the treatment site to allow adhesion followed by application of the VPM with the right amount of tension and border are of paramount importance or aggravation rather than improvement of the cutaneous defect may occur. Initially, the membrane should be changed frequently, once or twice a day in heavily contaminated or necrotic wounds. Side effects are usually related to improper application, with resultant leaking of fluid and irritation of normal skin. Recent success has been achieved by weekly application of VPM in the office, removal at home after several days, and subsequent use of 10% benzoyl peroxide lotion until the next office visit. Extreme caution must be exercised if VPM is used to treat patients who are severely leukopenic or malnourished.

  4. The role of topical agents in the healing of full-thickness wounds.

    PubMed

    Watcher, M A; Wheeland, R G

    1989-11-01

    Eight topical agents in current use were studied for their effects on wound contraction and rate of reepithelialization of full-thickness excisions using a porcine animal model. The following agents were applied daily for a period of 27 days: scarlet red ointment, benzoyl peroxide lotion, bacitracin ointment, silver sulfadiazine cream, aloe vera gel, tretinoin cream, capsaicin cream, and mupirocin ointment. The rate of reepithelialization was significantly enhanced by treatment with capsaicin, bacitracin, silver sulfadiazine, and scarlet red, and was markedly retarded by treatment with tretinoin. Wound contraction was significantly retarded by mupirocin, bacitracin, and silver sulfadizine. Knowledge of the effects of topical agents on various aspects of healing allows the clinician to choose the most appropriate material to use in a given clinical situation to optimize the healing process and produce the best final result.

  5. Crusted (Norwegian) Scabies Following Systemic and Topical Corticosteroid Therapy

    PubMed Central

    Janković, Aleksandar; Jovanović, Dragan; Ljubenović, Milanka

    2010-01-01

    It is a case study of a 62-yr-old female with crusted (Norwegian) scabies, which appeared during her treatment with systemic and topical corticosteroid therapy, under the diagnosis of erythroderma. In the same time, the patient had been suffered from hypothyoidism, and her skin changes were misdiagnosed, because it was thought that they are associated with her endocrine disorder. Suddenly, beside the erythema, her skin became hyperkeratotic, with widespread scaling over the trunk and limbs, and crusted lesions appeared on her scalp and ears. The microscopic examination of the skin scales with potassium hydroxide demonstrated numerous scabies mites and eggs. Repeated topical treatments with lindan, benzoyl benzoat and 10% precipitated sulphur ointment led to the complete resolution of her skin condition. PMID:20052371

  6. Silylative decarbonylation: A new route to arylsilanes

    SciTech Connect

    Rich, J.D. )

    1989-07-19

    A new synthetic procedure for the preparation of aromatic chlorosilanes via the palladium-catalyzed reaction of methylchlorodisilanes and aromatic acid chloride is described. The silylative decarbonylation process is solventless, can utilize low metal catalyst loadings (500-1,000 ppm Pd), is carried out under moderate conditions (145{degree}C), and selectively gives aromatic chlorosilanes in good yield, generally 60-85%. The procedure is tolerant of a variety of aromatic substituents, for example, alkyl, halo, nitro, cyano, imide, acid anhydride, etc., and the synthesis of several new substituted aromatic chlorosilanes containing benzoyl chloride and phthalic anhydride moieties is described. Chloromethyldisilane starting reagents are available from the direct reaction of methyl chloride and silicon, making this methodology an attractive synthetic route to functionalized aromatic chlorosilanes.

  7. Crystal structure of 4-meth­oxy-N-[(pyrrolidin-1-yl)carbo­thio­yl]benzamide

    PubMed Central

    Suhud, Khairi; Heng, Lee Yook; Hasbullah, Siti Aishah; Ahmad, Musa; Kassim, Mohammad B.

    2015-01-01

    In the title compound, C13H16N2O2S, the pyrrolidine ring has a twisted conformation on the central –CH2–CH2– bond. Its mean plane is inclined to the 4-meth­oxy­benzoyl ring by 72.79 (15)°. In the crystal, mol­ecules are linked by N—H⋯O and C—H⋯O hydrogen bonds to the same O-atom acceptor, forming chains along [001]. The chains are linked via slipped parallel π–π inter­actions [inter-centroid distance = 3.7578 (13) Å], forming undulating slabs parallel to (100). PMID:26029426

  8. Luminal proteinases from Plodia interpunctella and the hydrolysis of Bacillus thuringiensis CryIA(c) protoxin.

    PubMed

    Oppert, B; Kramer, K J; Johnson, D; Upton, S J; Mcgaughey, W H

    1996-06-01

    The ability of proteinases in gut extracts of the Indianmeal moth, Plodia interpunctella, to hydrolyze Bacillus thuringiensis (Bt) protoxin, casein, and rho-nitroanilide substrates was investigated. A polyclonal antiserum to protoxin CryIA(c) was used in Western blots to demonstrate slower protoxin processing by gut enzymes from Bt subspecies entomocidus-resistant larvae than enzymes from susceptible or kurstaki-resistant strains. Enzymes from all three strains hydrolyzed N-alpha-benzoyl-L-arginine rho-nitroanilide, N-succinyl-ala-ala-pro-phenylalanine rho-nitroanilide, and N-succinyl-ala-ala-pro-leucine rho-nitroanilide. Zymograms and activity blots were used to estimate the apparent molecular masses, number of enzymes, and relative activities in each strain. Several serine proteinase inhibitors reduced gut enzyme activities, with two soybean trypsin inhibitors, two potato inhibitors, and chymostatin the most effective in preventing protoxin hydrolysis.

  9. Synthesis and antimicrobial activity of some netropsin analogues.

    PubMed

    Khalaf, Abedawn I; Ebrahimabadi, Abdolrasoul H; Drummond, Allan J; Anthony, Nahoum G; Mackay, Simon P; Suckling, Colin J; Waigh, Roger D

    2004-11-01

    Nine novel lexitropsins were synthesized by linking two netropsin-like moieties through three different dicarboxylic acids; 9,10-dihydro-2,7-phenanthrenedicarboxylic acid; [(3-[[(carboxymethyl)amino]carbonyl]benzoyl)amino]acetic acid and indole-2,5-dicarboxylic acid. The netropsin residues were modified by the use of N-isopentylpyrrole, 5-methylthiophene or 5-isopropylthiazole heterocyclic building blocks in place of the usual N-methylpyrrole. The compounds were tested against five gram-positive bacteria: Staphylococcus aureus, Streptomyces faecalis, methicillin resistant Staphylococcus aureus, Enterobacter cloacae, Mycobacterium fortuitum, three gram-negative bacteria: Klebsiella aerogenes, Proteus vulgaris, Escherichia coli and three fungi: Aspergillus niger, Candida albicans and Aspergillus nidulans. Some of the compounds showed significant inhibitory effects on the growth of the microorganisms. PMID:15505717

  10. Synthesis and evaluation of novel benzophenone-thiazole derivatives as potent VEGF-A inhibitors.

    PubMed

    Prashanth, T; Thirusangu, Prabhu; Vijay Avin, B R; Lakshmi Ranganatha, V; Prabhakar, B T; Khanum, Shaukath Ara

    2014-11-24

    A series of 2-(4-benzoyl-phenoxy)-N-(4-phenyl-thiazol-2-yl)-acetamides (10a-n) were synthesized by multistep reaction sequence and all the compounds were well characterized for structural elucidation. The in vitro cytotoxicity of compounds 10a-n was evaluated against EAC and DLA cell lines using trypan blue dye exclusion method. Further MTT assay and LDH release assay, followed by in vivo studies on murine model were also evaluated. The compound 10h with a methyl and fluoro groups at benzophenone moiety and methoxy group at phenyl ring was in a leading position to exhibit the promising antiproliferative effect through translational VEGF-A inhibition. PMID:25261825

  11. Contact dermatitis to topical acne drugs: a review of the literature.

    PubMed

    Foti, Caterina; Romita, Paolo; Borghi, Alessandro; Angelini, Gianni; Bonamonte, Domenico; Corazza, Monica

    2015-01-01

    Acne vulgaris is a chronic dermatological disorder that affects the majority of teenagers in the Western world. Topical therapy is widely used to treat mild-moderate acne and is known as well-tolerated thanks to its low systemic toxicity, although associated to skin adverse effects. Acne seems to be associated also to an intrinsic alteration of the epidermal barrier, regarding both the upper and the follicular stratum corneum that promotes the onset of such local side effects. The commonest one is irritant contact dermatitis, an event of frequent observation occurring with erythema, burning, dryness, scaling, and itching, usually characterized by low severity and limited duration. Among topical acne drugs, retinoids are the most irritating ones. Another side effect is allergic contact dermatitis: it is rare and mainly associated to benzoyl peroxide.

  12. Synthesis, spectroscopic properties and theoretical studies of bis-Schiff bases derived from polyamine and pyrazolones.

    PubMed

    Ren, Tiegang; Liu, Shuyun; Li, Guihui; Zhang, Jinglai; Guo, Jia; Li, Weijie; Yang, Lirong

    2012-11-01

    A series of novel bis-Schiff base were synthesized from 1-aryl-3-methyl-4-benzoyl-5-pyrazolones and diethylenetriamine (or triethylenetetramine) as the starting materials. All of these bis-Schiff bases were characterized by means of NMR, IR, and MS. The UV-vis absorption spectra and fluorescent spectra of these bis-Schiff bases were also measured. Moreover, the B3LYP/6-31G(d) method was used to optimize the ground state geometry of the bis-Schiff bases; and the UV-vis spectroscopic properties of the products were computed and compared with corresponding experimental data based on cc-pVDZ basis set of TD-B3LYP method. It has been found that all of these bis-Schiff bases show a remarkable absorption peak in a wavelength range of 270-340 nm; and their maximum emission peaks are around 348 nm.

  13. New 1,6-heptadienes with pyrimidine bases attached: Syntheses and spectroscopic analyses

    NASA Astrophysics Data System (ADS)

    Hammud, Hassan H.; Ghannoum, Amer M.; Fares, Fares A.; Abramian, Lara K.; Bouhadir, Kamal H.

    2008-06-01

    A simple, high yielding synthesis leading to the functionalization of some pyrimidine bases with a 1,6-heptadienyl moiety spaced from the N - 1 position by a methylene group is described. A key step in this synthesis involves a Mitsunobu reaction by coupling 3N-benzoyluracil and 3N-benzoylthymine to 2-allyl-pent-4-en-1-ol followed by alkaline hydrolysis of the 3N-benzoyl protecting groups. This protocol should eventually lend itself to the synthesis of a host of N-alkylated nucleoside analogs. The absorption and emission properties of these pyrimidine derivatives ( 3- 6) were studied in solvents of different physical properties. Computerized analysis and multiple regression techniques were applied to calculate the regression and correlation coefficients based on the equation that relates peak position λmax to the solvent parameters that depend on the H-bonding ability, refractive index, and dielectric constant of solvents.

  14. Design, Synthesis and antiHIV activity of Novel Isatine-Sulphonamides.

    PubMed

    Selvam, P; Murugesh, N; Chandramohan, M; Debyser, Z; Witvrouw, M

    2008-11-01

    A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides. The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass). Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration.

  15. Design, Synthesis and antiHIV activity of Novel Isatine-Sulphonamides

    PubMed Central

    Selvam, P.; Murugesh, N.; Chandramohan, M.; Debyser, Z.; Witvrouw, M.

    2008-01-01

    A series of novel isatine-sulphonamide derivatives have been synthesized by combining isatin derivatives with sulphonamides. The structure of the synthesized compounds were elucidated by spectral analysis (IR, NMR and Mass). Investigation of anti-HIV activity was done against HIV-1(IIIB) in MT-4 cells and HIV integrase inhibitory activity. 4-(1-acetyl-5-methyl-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzenesulfonamide (SPIII-5ME-AC) inhibits the HIV Integrase enzymatic activity as both over all and strand transfer reaction and 4-(1-benzoyl-5-chloro-2-oxoindolin-3-ylideneamino)-N-(4,6-dimethylpyrimidin-2-yl)benzene sulfonamide (SPIII-5Cl-BZ) exhibits 36 percent maximum protection against HIV-1 at sub toxic concentration. PMID:21369440

  16. Crystal structure of N'-[bis-(ethyl-sulfan-yl)methyl-idene]-2-hy-droxy-4-meth-oxy-benzohydrazide.

    PubMed

    Nath, Paras; Bharty, Manoj K; Chaurasia, Rahul; Kumari, Sanyucta; Gupta, Sushil K

    2015-12-01

    In the title compound, C13H18N2O3S2, the amide group is in the plane of the -benzoyl ring with a C-N-N-C torsion angle of 177.63 (12)°. The two di-thio-ate groups are in an anti conformation [torsion angles = 173.68 (8) and -9.98 (10)°]. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal, an O-H⋯O hydrogen bond and a weak C-H⋯O contact involving the same acceptor atom generate an S(6) ring motif and give rise to chains along [010]. PMID:26870554

  17. Synthesis and spectroscopic studies of 4-phenylacetyl-3-methyl-1-phenylpyrazolone-5 and its thorium(VI), lanthanum(III) and lead(II) complexes

    NASA Astrophysics Data System (ADS)

    Uzoukwu, Bieluonwu Augustus; Adiukwu, Patricia Ugboaku

    1995-12-01

    The synthesis of 4-phenylacetyl-3-methyl-1-phenylpyrazolone-5 is reported. Analysis of its IR and NMR spectral data has revealed that the ligand is bidentate and has spectral properties that resemble neither those of the 4-benzoyl, 4-acetyl derivatives nor those of the trihaloacetyl derivatives which have p Ka values < 4.0. Instead the spectral properties are similar to those of the 4-alkanoyl derivatives which have p Ka values . 4.0. The thorium(VI), lanthanum(III) and lead(II) complexes were isolated and characterized by UV, IR and 1H, 13C NMR spectral studies. The complexes were anhydrous and conform to a general molecular formula ML n where M( n) is Th(VI), La(III), Pb(II).

  18. Two classes of single-stranded regions evident in deproteinized preparations of replicating DNA isolated from mammalian cells

    SciTech Connect

    Stewart, B.W.; Kavallaris, M.; Catchpoole, D.; Norris, M.D. )

    1991-02-01

    In DNA isolated from proliferating human lymphoblastoid CCRF-CEM cells which had been pulse-labeled by exposure to (3H)thymidine for periods from 30 s to 10 min, single-stranded regions were analyzed by caffeine-gradient elution from benzoylated DEAE-cellulose. Two classes of structural defect were evident. Some replicating DNA exhibited single-stranded regions of approximately 200 nucleotides, while most newly incorporated radioactivity was associated with DNA containing single-stranded regions from 900 to approximately 4000 nucleotides. The distribution of thymidine-derived radioactivity did not suggest sequential or preferential labeling of these DNA fractions as the incorporation time was varied. The findings may be correlated with recent proposals regarding the structural basis of eukaryotic DNA replication.

  19. Synthesis and X-ray Characterization of Alkali Metal 2-Acyl-1,1,3,3-tetracyanopropenides.

    PubMed

    Karpov, Sergey V; Grigor'ev, Arthur A; Kayukov, Yakov S; Karpova, Irina V; Nasakin, Oleg E; Tafeenko, Victor A

    2016-08-01

    A novel route for synthesis of 2-acyl-1,1,3,3-tetracyanopropenides (ATCN) salts in high yields and excellent purities starting from readily available methyl ketones, malononitrile, bromine, and alkali metal acetates is reported. The starting aryl(heteroaryl) methyl ketones were oxidized to the corresponding α-ketoaldehydes by new a DMSO-NaBr-H2SO4 oxidation system in yields up to 90% within a short reaction time of 8-10 min. The subsequent stages of ATCN preparation are realized in aqueous media without use of any toxic solvents, in accordance with principle 5 of "green chemistry". Lithium, sodium, potassium, rubidium, and cesium 2-benzoyl-1,1,3,3-tetracyanopropenides were characterized by X-ray diffraction analysis. These salts show a good potential for synthesis of five- and six-membered heterocycles and may serve as potentially useful ligands in coordination and supramolecular chemistry. PMID:27384963

  20. Synthesis, xanthine oxidase inhibition, and antioxidant screening of benzophenone tagged thiazolidinone analogs.

    PubMed

    Ranganatha, V Lakshmi; Begum, A Bushra; Naveen, P; Zameer, Farhan; Hegdekatte, Raghavendra; Khanum, Shaukath Ara

    2014-08-01

    A series of novel 2-(diaryl methanone)-N-(4-oxo-2-phenyl-thiazolidin-3-yl)-acetamides were synthesized by various Schiff bases of (4-benzoyl-phenoxy)-aceto hydrazide with thioglycolic acid. The structures of the newly synthesized compounds were confirmed by IR, (1) H NMR, mass spectra, and C, H, N analysis. Further, all the synthesized compounds 9a-n were evaluated for xanthine oxidase (XO) inhibition and antioxidant properties. Among all the tested compounds, 9f, 9m, and 9n demonstrated potent XO inhibition of 52, 76, and 26%, respectively, compared to the standard drug allopurinol, which is evident from in vitro and in silico analysis. On the other hand, compounds 9c, 9d, and 9k exhibit potent antioxidant properties. PMID:24853493

  1. Salmonellosis Pacifarin Activity of Enterobactin

    PubMed Central

    Wawszkiewicz, E. J.; Schneider, H. A.; Starcher, B.; Pollack, J.; Neilands, J. B.

    1971-01-01

    Salmonellosis pacifarin activity is detected by an increased survivorship of mice, doubly infected with avirulent and virulent Salmonella typhimurium, when heretofore unknown agents, found in certain natural foodstuffs and in the supernatants of certain bacterial cultures, are fed to the infected animals as dietary supplements. We now announce the identity of one of these agents: it is enterobactin, a cyclic trimer of 2,3-dihydroxy-N-benzoyl-L-serine. Basal diets enriched with as little as 2 mg of crystalline trimer per kg of diet show pacifarin activity to a statistically significant degree. Diets supplemented with as much as 100 mg of the monomer per kg of diet show no such activity. PMID:5288264

  2. Comparative Study on the Immobilization of Lipase on Chitosan Gels Modified by Different Hydrophobic Groups

    NASA Astrophysics Data System (ADS)

    Deng, Hong-Tao; Lin, Yan; Wang, Juan-Juan; Liu, Zhong-Yang; Ma, Miao; Zheng, Fei

    The hydrophobic surface modification of chitosan gels (CS) was carried out using the amidating reaction of amido groups on a gel surface with propionic acid, stearic acid, and benzoic acid, respectively, activated by 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC) and N-hydroxysuccinimide (NHS). Lipase from Candida rugosa was immobilized by adsorption on the nascent CS, propionyl-modified gels (PCS), stearyl-modified gels (SCS), and benzoyl-modified gels (BCS), respectively. The adsorption capacity and activity of immobilized lipase were investigated. It was found that the surface modification improved the adsorption capacity of lipase, and the activity retention of immobilized lipase increased from 52.34% for CS to 57.17%, 78.26% and 69.22%, respectively, for PCS, SCS, and BCS.

  3. Rosacea and rhinophyma.

    PubMed

    Tüzün, Yalçın; Wolf, Ronni; Kutlubay, Zekayi; Karakuş, Ozge; Engin, Burhan

    2014-01-01

    Rosacea is a common and chronic inflammatory cutaneous disease with unknown etiology. The pathophysiology of rosacea is still poorly understood. Epidemiological studies indicate a genetic component, but a rosacea gene has not been detected yet. Recent molecular studies propose that an altered innate immune response is involved in the pathogenesis of the rosacea disease. Signs of rosacea are indicated by the presence of characteristic facial or ocular inflammation involving both the vascular and tissue stroma. A wide range of drug options is available for the treatment of rosacea, including several topical ones (metronidazole, antibiotics, azelaic acid, benzoyl peroxide, sulfacetamide/sulfur, retinoids) and oral ones (mainly tetracyclines, metronidazole, macrolides, isotretinoin). This review highlights the recent clinical and pathophysiological developments concerning rosacea.

  4. The last step in cocaine biosynthesis is catalyzed by a BAHD acyltransferase.

    PubMed

    Schmidt, Gregor Wolfgang; Jirschitzka, Jan; Porta, Tiffany; Reichelt, Michael; Luck, Katrin; Torre, José Carlos Pardo; Dolke, Franziska; Varesio, Emmanuel; Hopfgartner, Gérard; Gershenzon, Jonathan; D'Auria, John Charles

    2015-01-01

    The esterification of methylecgonine (2-carbomethoxy-3β-tropine) with benzoic acid is the final step in the biosynthetic pathway leading to the production of cocaine in Erythoxylum coca. Here we report the identification of a member of the BAHD family of plant acyltransferases as cocaine synthase. The enzyme is capable of producing both cocaine and cinnamoylcocaine via the activated benzoyl- or cinnamoyl-Coenzyme A thioesters, respectively. Cocaine synthase activity is highest in young developing leaves, especially in the palisade parenchyma and spongy mesophyll. These data correlate well with the tissue distribution pattern of cocaine as visualized with antibodies. Matrix-assisted laser-desorption ionization mass spectral imaging revealed that cocaine and cinnamoylcocaine are differently distributed on the upper versus lower leaf surfaces. Our findings provide further evidence that tropane alkaloid biosynthesis in the Erythroxylaceae occurs in the above-ground portions of the plant in contrast with the Solanaceae, in which tropane alkaloid biosynthesis occurs in the roots.

  5. An investigation of nitrile transforming enzymes in the chemo-enzymatic synthesis of the taxol sidechain.

    PubMed

    Wilding, Birgit; Veselá, Alicja B; Perry, Justin J B; Black, Gary W; Zhang, Meng; Martínková, Ludmila; Klempier, Norbert

    2015-07-28

    Paclitaxel (taxol) is an antimicrotubule agent widely used in the treatment of cancer. Taxol is prepared in a semisynthetic route by coupling the N-benzoyl-(2R,3S)-3-phenylisoserine sidechain to the baccatin III core structure. Precursors of the taxol sidechain have previously been prepared in chemoenzymatic approaches using acylases, lipases, and reductases, mostly featuring the enantioselective, enzymatic step early in the reaction pathway. Here, nitrile hydrolysing enzymes, namely nitrile hydratases and nitrilases, are investigated for the enzymatic hydrolysis of two different sidechain precursors. Both sidechain precursors, an openchain α-hydroxy-β-amino nitrile and a cyanodihydrooxazole, are suitable for coupling to baccatin III directly after the enzymatic step. An extensive set of nitrilases and nitrile hydratases was screened towards their activity and selectivity in the hydrolysis of two taxol sidechain precursors and their epimers. A number of nitrilases and nitrile hydratases converted both sidechain precursors and their epimers.

  6. Synthesis of novel amphiphilic hyaluronan containing-aromatic fatty acids for fabrication of polymeric micelles.

    PubMed

    Matelová, Alena; Huerta-Angeles, Gloria; Šmejkalová, Daniela; Brůnová, Zdislava; Dušek, Jan; Vícha, Robert; Velebný, Vladimír

    2016-10-20

    Novel hydrophobized hyaluronan (HA) derivatives, containing ω-phenylalkanoic acids (ω-PAA, 4-phenylbutyric acid, 6-phenylhexanoic, 8-phenyloctanoic or 11-tolylundecanoic acids) were prepared by esterification. Mixed anhydrides obtained after reaction of the carboxyl acid moiety and benzoyl chloride were found to be active acylating agents, affording hydrophobized HA in good yield and under mild conditions. The reactivity of the aromatic fatty acids towards esterification has decreased with the increasing length of the aliphatic spacer between the aromatic substituent and carboxylic acid moiety. The novel HA derivatives self-assembled from very low concentrations and were found to be non-cytotoxic. The potential use of ω-phenylalkanoic acids grafted-HA towards drug delivery applications was demonstrated by hydrophobic drugs (resveratrol and retinyl palmitate) encapsulation. The drug loading capacity of the novel HA derivatives was significantly improved most likely because of π⋯π interactions between the micelle core and loaded hydrophobic aromatic compound.

  7. Filler-polymer bonding and its role in elastomer reinforcement

    SciTech Connect

    Xu, Ping, Mark, J.E.

    1993-12-31

    Iron oxide particles were blended into samples of cis-1,4-polybutadiene and polyisobutylene, and both the unfilled polymers and the resulting polymer-filler mixture were cured with benzoyl peroxide. The filled networks were cloudy, but strips extracted using a toluene-hydrochloric acid mixture became as clear as the unfilled networks, suggesting removal of the filler particles. Equilibrium swelling and stress-strain measurements in elongation were carried out the unfilled elastomer and on the filled ones, both before and after extraction. There were no significant differences between the stress-strain isotherms and degrees of equilibrium swelling of the unfilled networks and the corresponding properties of the previously-filled networks after the filler particles were removed. This suggests that for these systems, the bonding between the filler particles and the polymer chains is physical rather than chemical.

  8. Activity of capryloyl collagenic acid against bacteria involved in acne.

    PubMed

    Fourniat, J; Bourlioux, P

    1989-12-01

    Synopsis Capryloyl collagenic acid (Lipacide C8Co) has similar bacteriostatic activity in vitro to that of benzoyl peroxide towards the bacteria found in acne lesions (Staphylococcus aureus, Staphylococcus epidermidis and Propionibacterium acnes) (MIC between 1 and 4 mg ml(-1) for C8Co, and between 0.5 and 5 mg ml(-1) for benzoyl peroxide). The presence of Emulgine M8 did not affect the bacteriostatic activity of C8Co. A 4% w/v solution of C8Co (incorporating Emulgine M8) fulfilled the criteria for an antiseptic preparation as laid down by the French Pharmacopoeia (10th Edition), and had a spectrum 5 bactericidal activity according to the French Standard AFNOR NF T 72-151. The excellent cutaneous tolerance of capryloyl collagenic acid would indicate that an aqueous solution might be of value for topical treatment of the bacterial component of acne. Résumé Activité antibactérienne de l'acide capryloyl-collagénique vis à vis des bactéries impliquées dans l'etiologie de l'acné L'acide capryloyl-collagénique (Lipacide C8Co) et le peroxyde de benzoyle présentent une activité bactériostatique in-vitroéquivalente vis à vis des espèces bactériennes retrouvées au niveau des lésions acnéiques (Staphylococcus aureus, S. epidermidis et Propionibacterium acnes) (CMI comprise entre 1 et 4 mg ml(-1) pour le lipoaminoacide, et 0,5 et 5 mg ml(-1) pour le peroxyde de benzoyle). La mise en solution aqueuse de l'acide capryloyl-collagénique en présence d'Emulgine M8 ne modifie pas son activité bactériostatique. Une telle solution, à 4% m/V d'acide capryloyl-collagénique et 5% m/V d'Emulgine M8, satisfait à l'essai d'activité des préparations antiseptiques décrit à la Pharmacopée Française (Xème Ed.) (concentration minimale antiseptique: 10% v/V, pour un temps de contact de 5 min à 32 degrees C entre les germes tests et la solution diluée en eau distillée), et posséde une activité bactéricide antiseptique spectre 5 conforme à la norme AFNOR NF T

  9. [Lavoisier and radicals].

    PubMed

    Lafont, Olivier

    2007-01-01

    Lavoisier and his co-workers (Guyton de Morveau, Bertholet, Fourcroy) considered that acids were constituted of oxygen and of something else that they called radicals. These radicals were known in some cases, i.e. nitrogen for nitrous acid, carbon for carbonic acid, phosphorus for phosphoric acid. In the case of sulfur, the sulfuric radical could be associated with different quantities of oxigen leading to sulfuric or sulfurous acids. In other cases radicals remained unknown at the time i.e. muriatic radical for muriatic acid, or benzoyl radical for benzoic acid. It is interesting to notice that Lavoisier evoked the case of compound radicals constituted of different substances such as carbon and hydrogen.

  10. Bottom-Up Construction of a CO2-Based Cycle for the Photocarbonylation of Benzene, Promoted by a Rhodium(I) Pincer Complex.

    PubMed

    Anaby, Aviel; Feller, Moran; Ben-David, Yehoshoa; Leitus, Gregory; Diskin-Posner, Yael; Shimon, Linda J W; Milstein, David

    2016-08-10

    The use of carbon dioxide for synthetic applications presents a major goal in modern homogeneous catalysis. Rhodium-hydride PNP pincer complex 1 is shown to add CO2 in two disparate pathways: one is the expected insertion of CO2 into the metal-hydride bond, and the other leads to reductive cleavage of CO2, involving metal-ligand cooperation. The resultant rhodium-carbonyl complex was found to be photoactive, enabling the activation of benzene and formation of a new benzoyl complex. Organometallic intermediate species were observed and characterized by NMR spectroscopy and X-ray crystallography. Based on the series of individual transformations, a sequence for the photocarbonylation of benzene using CO2 as the feedstock was constructed and demonstrated for the production of benzaldehyde from benzene. PMID:27400288

  11. Synthesis, characterization and antibacterial study of tripodal tris-(N-benzoylthioureido)ethylamine

    SciTech Connect

    Adan, Dalina; Yamin, Bohari; Leng, Ong Wei; Ibrahim, Nazlina

    2014-09-03

    A new tripodal tris-(N-benzoylthiouredoethyl)amine has been successfully synthesized and characterized by spectroscopic technique such as FTIR, ESI MS, {sup 1}H and {sup 13}C NMR. The microanalysis data is in a good agreement with the expected molecular formula. The {sup 1}H NMR chemical shift for both amide and thioamide proton are at lower field than their normal value indicates the presence of the hydrogen bond between the carbonyl oxygen atom and thioamide hydrogen. This is possible when the benzoyl group adopt a trans configuration againts thione group along the C-N bond. The compound has been tested for antibacterial activity against three selected bacteria namely Staphylococcus aureus, Proteus vulgaris and Pseudomanas aeroginosa but there is no significant activities observed.

  12. Recognizing a limitation of the TBLC-activated peroxide system on low-temperature cotton bleaching.

    PubMed

    Chen, Wenhua; Wang, Lun; Wang, Dong; Zhang, Jingjing; Sun, Chang; Xu, Changhai

    2016-04-20

    In this study, cotton was bleached at low temperatures with an activated peroxide system which was established by incorporating a bleach activator, namely, N-[4-(triethylammoniomethyl)benzoyl]caprolactam chloride (TBCC) into an aqueous solution of hydrogen peroxide (H2O2). Experimental results showed that the bleaching performance was unexpectedly diminished as the TBCC concentration was increased over the range of 25-100g/L. Kinetic adsorption experiment indicated that this was most likely ascribed to the adsorptive interactions of TBCC and the in situ-generated compounds with cotton fibers. Such a limitation was especially fatal to cold pad-batch bleaching process of cotton in which a high TBCC concentration was often required. The results of this study may stimulate further research to avoid or overcome the limitation of the TBCC-activated peroxide system on low-temperature cotton bleaching.

  13. Antibiotic resistance to Propionobacterium acnes: worldwide scenario, diagnosis and management.

    PubMed

    Sardana, Kabir; Gupta, Tanvi; Garg, Vijay K; Ghunawat, Sneha

    2015-07-01

    Antibiotic resistance in cutaneous Propionobacterium is a global problem. As a general rule, resistance levels are high to macrolides, trimethoprim/sulfamethoxazole and clindamycin, while tetracyclines and levofloxacin have low resistance potential. Newer preparations like doxycycline MR and doxycycline 20 mg are subantimicrobial and may not lead to resistance. Sampling techniques are crucial to determine resistance. Genomic evaluation using 16S ribosomal RNA gene sequencing can be useful in diagnosing mutations and mapping phylotypes of Propionobacterium acnes. Resistance may lead to slow response and relapses. Apart from benzoyl peroxide, azelaic acid, topical dapsone, oral zinc and retinoids, novel molecules with little resistance potential include octadecenedioic acid, phytosphingosine, lauric acid, retapamulin, resveratrol, T-3912 and NB-003. The use of oral retinoids and non-antibiotics like zinc can prevent resistance and help reduce the dependence on antibiotics. PMID:26025191

  14. Quantitation of Flavanols, Proanthocyanidins, Isoflavones, Flavanones, Dihydrochalcones, Stilbenes, Benzoic Acid Derivatives Using Ultraviolet Absorbance after Identification by Liquid Chromatography–Mass Spectrometry

    PubMed Central

    Lin, Long-Ze; Harnly, James M.

    2013-01-01

    A general method was developed for the systematic quantitation of flavanols, proanthocyanidins, isoflavones, flavanones, dihydrochalcones, stilbenes, and hydroxybenzoic acid derivatives (mainly hydrolyzable tannins) based on UV band II absorbance arising from the benzoyl structure. The compound structures and the wavelength maximum were well correlated and were divided into four groups: the flavanols and proanthocyanidins at 278 nm, hydrolyzable tannins at 274 nm, flavanones at 288 nm, and isoflavones at 260 nm. Within each group, molar relative response factors (MRRFs) were computed for each compound based on the absorbance ratio of the compound and the group reference standard. Response factors were computed for the compounds as purchased (MRRF), after drying (MRRFD), and as the best predicted value (MRRFP). Concentrations for each compound were computed based on calibration with the group reference standard and the MRRFP. The quantitation of catechins, proanthocyanidins, and gallic acid derivatives in white tea was used as an example. PMID:22577798

  15. Zinc-catalyzed depolymerization of end-of-life polysiloxanes.

    PubMed

    Enthaler, Stephan

    2014-03-01

    Polymers occupy an important role in our current society. Besides their great success, an issue is the accumulation of huge amounts of end-of-life polymers. Currently, the waste management is based primarily on landfills, thermal recycling, and downcycling. Notably, only a small portion of end-of-life materials is recycled by depolymerization, which refers to the creation of synthetic precursors that can be polymerized to new polymers to close the cycle. Widely used polymers in modern times are silicones (polysiloxanes), the intrinsic properties of which make their depolymerization demanding; only a few high-temperature or less environmentally friendly processes have been reported. In this regard, we have established an efficient low-temperature protocol for the depolymerization of silicones with benzoyl fluoride in the presence of cheap zinc salts as precatalysts to yield defined products. Notably, the products can be useful synthetic precursors for the preparation of new polymers, so that an overall recycling process is feasible. PMID:24501107

  16. Crystal structure of 1-ferrocenyl-2-(4-methyl-benzo-yl)spiro-[11H-pyrrolidizine-3,11'-indeno[1,2-b]quinoxaline].

    PubMed

    Chandralekha, Kuppan; Gavaskar, Deivasigamani; Sureshbabu, Adukamparai Rajukrishnan; Lakshmi, Srinivasakannan

    2014-09-01

    In the title compound, [Fe(C5H5)(C34H28N3O)], the four-fused-rings system of the 11H-indeno-[1,2-b]quinoxaline unit is approximately planar [maximum deviation = 0.167 (4) Å] and forms a dihedral angle of 37.25 (6)° with the plane of the benzene ring of the methyl-benzoyl group. Both pyrrolidine rings adopt a twist conformation. An intra-molecular C-H⋯O hydrogen bond is observed. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions, forming double chains extending parallel to the c axis.

  17. Continuous method to determine the trypsin inhibitor activity in soybean flour.

    PubMed

    Coscueta, Ezequiel R; Pintado, Manuela E; Picó, Guillermo A; Knobel, Gastón; Boschetti, Carlos E; Malpiedi, Luciana Pellegrini; Nerli, Bibiana B

    2017-01-01

    The determination of trypsin inhibitor (TI) activity is of importance to evaluate the nutritional value of soybean flours. An analytical method, which involves a continuous spectrophotometric rate determination for trypsin activity against the substrate N-benzoyl-DL-arginine p-nitroanilide, is proposed as an alternative to the standard discontinuous assay. Stopping the reaction with acetic acid and a centrifugation/filtration step to decrease turbidity are not required, thus reducing costs and sample preparation time. The TI activity of different flour samples, determined by both assays, demonstrated to be statistically comparable, irrespective of the TI concentration level. The coefficients of variation of the novel method did not exceed 8% at any concentration level. The curves of progress reaction showed a non-linear behavior in samples without TI. A reduction of incubation time from 10min to 2min increased the method sensitivity and extended its linear range. A more economical, faster and simpler assay was developed. PMID:27507460

  18. Key factor affecting the structural and textural properties of ZSM-5/MCM-41 composite

    NASA Astrophysics Data System (ADS)

    Boukoussa, Bouhadjar; Aouad, Nafissa; Hamacha, Rachida; Bengueddach, Abdelkader

    2015-03-01

    ZSM-5/MCM-41 micro/mesoporous composite materials were synthesized by the hydrothermal technique with alkali-treated ZSM-5 zeolite as source of silica and aluminum and characterized by various physico-chemical techniques such as X-ray diffraction (XRD), nitrogen sorption at 77 K, transmission electronic microscopy (TEM), FTIR spectroscopy and NH3 temperature programmed desorption (TPD) techniques. The effect of concentration of CTAB in the synthesis of these solids has been investigated, the mesopore volume, surface area and surface acidity decrease with increasing the concentration of CTAB. Increasing the CTAB concentration causes the recrystallization of zeolite ZSM-5 and it disadvantage the formation of mesoporous materials MCM-41. The catalytic activity of ZSM-5/MCM-41 materials has been evaluated in the Friedel-Crafts acylation of anisole with benzoyl chloride as alkylating agent. The results revealed the reaction to be influenced by surface area, pore volume and surface acidity.

  19. How does our increased understanding of the role of inflammation and innate immunity in acne impact treatment approaches?

    PubMed

    Leyden, James

    2016-01-01

    A supplement article recently published in the Journal of the European Academy of Dermatology and Venereology by Dréno et al., members of the Global Alliance to Improve Outcomes in Acne group, summarized the data for the emerging concept that inflammation in general and the innate immune system specifically play a central role in the pathogenesis of acne. This review, entitled "Understanding innate immunity and inflammation in acne: implications for management", also discusses the impact of different treatment options on the innate immune response and inflammation. The aim of the present summary is to provide a synopsis of the key points made in the paper, from the members of the Global Alliance, as relevant to the main article within this supplement: "Recent advances in the use of adapalene 0.1%/benzoyl peroxide 2.5% to treat acne patients with moderate to severe acne".

  20. Acyltransferase activities of the high-molecular-mass essential penicillin-binding proteins.

    PubMed

    Adam, M; Damblon, C; Jamin, M; Zorzi, W; Dusart, V; Galleni, M; el Kharroubi, A; Piras, G; Spratt, B G; Keck, W

    1991-10-15

    The high-molecular-mass penicillin-binding proteins (HMM-PBPs), present in the cytoplasmic membranes of all eubacteria, are involved in important physiological events such as cell elongation, septation or shape determination. Up to now it has, however, been very difficult or impossible to study the catalytic properties of the HMM-PBPs in vitro. With simple substrates, we could demonstrate that several of these proteins could catalyse the hydrolysis of some thioesters or the transfer of their acyl moiety on the amino group of a suitable acceptor nucleophile. Many of the acyl-donor substrates were hippuric acid or benzoyl-D-alanine derivatives, and their spectroscopic properties enabled a direct monitoring of the enzymic reaction. In their presence, the binding of radioactive penicillin to the PBPs was also inhibited. PMID:1953655