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Fernando Fernández-Nieto, M Rita Paleo, Roberto Colunga, M Luz Raposo, Luis Garcia-Rio, F Javier Sardina
Lithiation reactions of tertiary benzylic esters and carbamates have been studied. Kinetic methodology revealed that a two-step reaction pathway should be considered for these reactions, where either the lithium precomplexation and/or the proton transfer steps can be rate determining. Kinetic isotopic effects were evaluated by comparison of the lithiations of the corresponding protio/deutero substrates, and the results obtained support the notion that lithium precomplexation is taking place on the reaction pathway and that it is the rate-determining step in this transformation...
October 21, 2016: Organic Letters
Michelle R Robinson, Jennifer S Brodbelt
Tyrosine sulfation is an important post-translational modification but remains difficult to detect in biological samples owing to its low stoichiometric abundance and the lack of effective enrichment methods. In the present study, weak anion exchange (WAX) is evaluated for the enrichment of sulfopeptides that have been modified via carbamylation to convert all primary amines to less basic carbamates. The decrease in basicity enhanced the binding of carbamylated sulfopeptides to WAX resin relative to non-sulfated peptides...
October 21, 2016: Analytical Chemistry
Xiaoli Xu, Yue Wu, Mingyang Hu, Xiang Li, Qichao Bao, Jinlei Bian, Qidong You, Xiaojin Zhang
DDO-6101, a simplified structure obtained from the Garcinia natural product (NP) gambogic acid (GA), has been previously shown to possess high cytotoxicity to a variety of human tumour cell lines. To improve its physicochemical properties and in vivo cytotoxic potency, a series of novel carbamate-bearing derivatives based on DDO-6101 was synthesized and characterized. The structural modifications revealed that the presence of a carbamate moiety was useful for obtaining comparable cytotoxicity and improved aqueous solubility and permeability...
October 21, 2016: Scientific Reports
Sandhya, Sandeep Kumar, Dinesh Kumar, Neeraj Dilbaghi
Synthesis and controlled release study of polymeric nanoformulation of carbendazim (2-benzimidazole carbamic acid methyl ester) using chitosan and pectin is reported in this article. The formulation was subjected to morphological, physiological, in vitro fungicide release and bio-efficacy evaluation studies. The average size of nanoparticles was found to be in the range of 70-90 nm as confirmed by transmission electron microscopy. The in vitro fungicide release of nanoformulated carbendazim was compared with pure carbendazim at different pH values...
October 19, 2016: Environmental Science and Pollution Research International
Yating Zhao, Binbin Huang, Chao Yang, Qingqing Chen, Wujiong Xia
A photoredox catalytic route to carbamates enabled by visible irradiation (or simply sunlight) has been developed. This process leads to a novel approach to the construction of heterocyclic rings wherein the amide or ester motifs of carbamates were assembled from three isolated components. Large-scale experiments were realized by employing continuous flow techniques, and reuse of photocatalyst demonstrated the green and sustainable aspects of this method.
October 18, 2016: Organic Letters
Sharon Downes, Darren Kriticos, Hazel Parry, Cate Paull, Nancy Schellhorn, Myron P Zalucki
Helicoverpa armigera is a major pest of agriculture, horticulture and floriculture throughout the old world and recently invaded parts of the new world. We overview of the evolution in thinking about the application of area-wide approaches to assist with its control by the Australian Cotton Industry to highlight important lessons and future challenges to achieving the same in the New World. An over-reliance of broad-spectrum insecticides led to Helicoverpa spp. in Australian cotton rapidly became resistant to DDT, synthetic pyrethroids, organophosphates, carbamates and endosulfan...
October 17, 2016: Pest Management Science
Carlos E Rodríguez-Rodríguez, Karina Madrigal-León, Mario Masís-Mora, Marta Pérez-Villanueva, Juan Salvador Chin-Pampillo
The use of fungal bioaugmentation represents a promising way to improve the performance of biomixtures for the elimination of pesticides. The ligninolyitc fungus Trametes versicolor was employed for the removal of three carbamates (aldicarb, ALD; methomyl, MTM; and methiocarb, MTC) in defined liquid medium; in this matrix ALD and MTM showed similar half-lives (14d), nonetheless MTC exhibited a faster removal, with a half-life of 6.5d. Then the fungus was employed in the bioaugmentation of an optimized biomixture to remove the aforementioned carbamates plus carbofuran (CFN)...
October 14, 2016: Ecotoxicology and Environmental Safety
Rapidah Mohamad, Normah Awang, Nurul Farahana Kamaludin, Mukesh M Jotani, Edward R T Tiekink
The crystal and mol-ecular structures of two tri-phenyl-tin di-thio-carbamates, [Sn(C6H5)3(C16H16NS2)], (I), and [Sn(C6H5)3(C7H14NO2S2)], (II), are described. In (I), the di-thio-carbamate ligand coordinates the Sn(IV) atom in an asymmetric manner, leading to a highly distorted trigonal-bipyramidal coordination geometry defined by a C3S2 donor set with the weakly bound S atom approximately trans to one of the ipso-C atoms. A similar structure is found in (II), but the di-thio-carbamate ligand coordinates in an even more asymmetric fashion...
October 1, 2016: Acta Crystallographica. Section E, Crystallographic Communications
Jian Du, Zoya Gridneva, Melvin C L Gay, Robert D Trengove, Peter E Hartmann, Donna T Geddes
Persistent organic pollutants in human milk (HM) at high levels are considered to be detrimental to the breastfed infant. To determine the pesticide concentration in HM, a pilot cross-sectional study of 40 Western Australian (WA) women was carried out. Gas chromatography-tandem mass spectrometry (GC-MS/MS) with a validated QuEChERS was used for the analysis of 88 pesticides in HM. p,p'-dichlorodiphenyldichloroethylene (p,p'-DDE) with a mean concentration of 62.8 ± 54.5 ng/g fat was found, whereas other organochlorines, organophosphates, carbamates and pyrethroids were not detected in HM...
October 8, 2016: Chemosphere
Benjamin D Menze, Jacob M Riveron, Sulaiman S Ibrahim, Helen Irving, Christophe Antonio-Nkondjio, Parfait H Awono-Ambene, Charles S Wondji
BACKGROUND: Despite the recent progress in establishing the patterns of insecticide resistance in the major malaria vector Anopheles funestus, Central African populations of this species remain largely uncharacterised. To bridge this important gap and facilitate the implementation of suitable control strategies against this vector, we characterised the resistance patterns of An. funestus population from northern Cameroon. METHODS AND FINDINGS: Collection of indoor-resting female mosquitoes in Gounougou (northern Cameroon) in 2012 and 2015 revealed a predominance of An...
2016: PloS One
Anna Żądło-Dobrowolska, Martyna Szczygieł, Dominik Koszelewski, Daniel Paprocki, Ryszard Ostaszewski
Enzyme triggered probes with a self-immolative linker for rapid and sensitive hydrolase detection through a cascade reaction have been reported. Their utility was proved by the preparation of three model compounds and their evaluation as enzyme substrates and demonstration of their applicability as fluorogenic probes for screening lipase, esterase and protease activities. These probes represent a new class of fluorogenic compounds, are stable under aqueous conditions and not susceptible to nonspecific degradation...
September 26, 2016: Organic & Biomolecular Chemistry
Helena Shifrin, Dorit Moradov, Corina Bejar, Donna Schorer-Apelbaum, Marta Weinstock
BACKGROUND: In search of safer treatments for inflammatory bowel disease in subjects not responding to, or showing adverse effects to TNF-α antagonists, we tested three novel indoline carbamates in the 2,4-dinitrobenzene sulfonic acid (DNBS) model of colitis in rats. The compounds have anti-inflammatory activity in other disease models in mice. METHODS: AN827 (3-(2-(methoxy carbonyl) ethyl) indolin-4-ylethyl methyl) carbamate (0.1 or 1mg/kg), AN680 (3-(2-(methoxy carbonyl) ethyl) indolin-6-ylethyl methyl) carbamate (1...
August 31, 2016: Pharmacological Reports: PR
Yuntao Shi, Marcus J C Long, Masha M Rosenberg, Shican Li, Aimee Kobjack, Philip Lessans, Rory T Coffey, Lizbeth Hedstrom
Targeted protein degradation is a promising strategy for drug design and functional assessment. Several small molecule approaches have been developed that localize target proteins to ubiquitin ligases, inducing ubiquitination and subsequent degradation by the 26S proteasome. We discovered that the degradation of a target protein can also be induced by a recognition ligand linked to tert-butyl carbamate (Boc3)-protected arginine (B3A). Here we show that this process requires the proteasome, but does not involve ubiquitination of the target protein...
October 5, 2016: ACS Chemical Biology
Nadine Borduas, Jonathan P D Abbatt, Jennifer Grace Murphy, Sui So, Gabriel da Silva
Research on the fate of reduced organic nitrogen compounds in the atmosphere has gained momentum since the identification of their crucial role in particle nucleation and the scale up of carbon capture and storage technology which employs amine-based solvents. Reduced organic nitrogen compounds have strikingly different lifetimes against OH radicals, from hours for amines to days for amides to years for isocyanates, highlighting unique functional group reactivity. In this work, we use ab initio methods to investigate the gas-phase mechanisms governing the reactions of amines, amides, isocyanates and carbamates with OH radicals...
October 3, 2016: Environmental Science & Technology
Christopher E Malmberg, Stephen Chamberland
The guanidine functional group, displayed most prominently in the amino acid arginine, one of the fundamental building blocks of life, is an important structural element found in many complex natural products and pharmaceuticals. Owing to the continual discovery of new guanidine-containing natural products and designed small molecules, rapid and efficient guanidinylation methods are of keen interest to synthetic and medicinal organic chemists. Because the nucleophilicity and basicity of guanidines can affect subsequent chemical transformations, traditional, indirect guanidinylation is typically pursued...
2016: Journal of Visualized Experiments: JoVE
Hassan Y Ebrahim, Mohamed M Mohyeldin, Mohammad M Hailat, Khalid A El Sayed
(1S,2E,4S,6R,7E,11E)-2,7,11-Cembratriene-4,6-diol (1) and its 4-epi-analog (2) are the cembranoid precursors to several key flavor ingredients in most Nicotiana (tobacco) species. Nearly 40-60% of 1 and 2 are purposely degraded during the commercial tobacco fermentation. However, 1 and 2 display promising bioactivities, including anticancer. Breast cancer is the most diagnosed cancer in women and ranked second female disease killer. The receptor tyrosine kinase c-Met correlates with aggressiveness of certain breast cancer phenotypes and thus considered a valid therapeutic target...
September 13, 2016: Bioorganic & Medicinal Chemistry
Guomin Yu, Yun Teng, Weidong Lai, Cuiyu Yin
Using wood pulps with the average degree of polymerization 300-350 and urea as raw materials, cellulose carbamates were successfully synthesized by esterification reaction in N, N-dimethylacetamide(DMAc), an inexpensive, high boiling aprotic and polar solvent, for the purpose of improving the solubility of cellulose, reducing costs and environmental pollution. The products were dissolved in 9% sodium hydroxide solution at a low temperature after washing and drying and the cellulose carbamates solutions were obtained...
September 22, 2016: International Journal of Biological Macromolecules
Shu-Yuan Cheng, Jiwon Seo, Bik Tzu Huang, Tanya Napolitano, Elise Champeil
Mitomycin C (MC), a commonly used anticancer drug, induces DNA damage via DNA alkylation. Decarbamoyl mitomycin C (DMC), another mitomycin lacking the carbamate at C10, generates similar lesions as MC. Interstrand cross-links (ICLs) are believed to be the lesions primarily responsible for the cytotoxicity of MC and DMC. The major ICL generated by MC (α-ICL) has a trans stereochemistry at the guanine-drug linkage whereas the major ICL from DMC (β-ICL) has the opposite, cis, stereochemistry. In addition, DMC can provoke strong p53-independent cell death...
September 23, 2016: International Journal of Oncology
Chieri Fujino, Yuki Tamura, Satoko Tange, Hiroyuki Nakajima, Seigo Sanoh, Yoko Watanabe, Naoto Uramaru, Hiroyuki Kojima, Kouichi Yoshinari, Shigeru Ohta, Shigeyuki Kitamura
The oxidative, reductive, and hydrolytic metabolism of methiocarb and the hydrolytic metabolism of carbaryl by liver microsomes and plasma of rats or humans were examined. The effects of the metabolism of methiocarb and carbaryl on their nuclear receptor activities were also examined. When methiocarb was incubated with rat liver microsomes in the presence of NADPH, methiocarb sulfoxide, and a novel metabolite, methiocarb sulfone were detected. Methiocarb sulfoxide was oxidized to the sulfone by liver microsomes and reduced back to methiocarb by liver cytosol...
2016: Journal of Toxicological Sciences
Antonio López, Vicent Yusà, Amalia Muñoz, Teresa Vera, Esther Borràs, Milagros Ródenas, Clara Coscollà
A risk assessment strategy based on the quantitative target analysis and semi-quantitative retrospective screening determination of pesticides in PM10 has been developed. The proposed methodology was applied to 345 real samples from nine stations of a Mediterranean area in Spain, and the risk was assessed for adult, children and infants. Forty pesticides were detected with average concentrations ranging from 8 to 30,000pgm(-3). Each station showed its specific pesticide profile, which is linked to the different types of crops around each station...
September 21, 2016: Science of the Total Environment
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