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indole hydroxylation

Felix Tobola, Mickael Lelimousin, Annabelle Varrot, Emilie Gillon, Barbara Darnhofer, Ola Blixt, Ruth Birner-Gruenberger, Anne Imberty, Birgit Wiltschi
Protein-carbohydrate interactions play crucial roles in biology. Understanding and modifying these interactions is of major interest for fighting many diseases. We took a synthetic biology approach and incorporated non-canonical amino acids into a bacterial lectin to modulate its interactions with carbohydrates. We focused on tryptophan that is prevalent in carbohydrate binding sites. The exchange of the tryptophan residues with analogs fluorinated at different positions resulted in three distinctly fluorinated variants of the lectin from Ralstonia solanacearum...
May 29, 2018: ACS Chemical Biology
Lin Zhang, Haoting Tian, Ran Hong, Chao Wang, Yi Wang, Anping Peng, Cheng Gu
Atrazine (2-chloro-4-ethylamino-6-isopropylamino-s-triazine) is a commonly used agricultural herbicide that, as a result, is frequently detected in surface and ground water. In this study, we provide evidence of the photo-oxidation of atrazine under environmentally relevant conditions, specifically, in the presence of natural montmorillonite clay and the ubiquitous phytohormone indole-3-acetic acid (IAA). The reaction is initiated by the generation of hydrated electrons from the photo-ionization of IAA. These electrons react with protons and dissolved oxygen to form hydroxyl radicals, which promote the further degradation of atrazine...
May 17, 2018: Environmental Pollution
Erika N Bentz, Rosana Maria Lobayan, Henar Martinez, Pilar Redondo, Antonio Largo
A computational kinetics study of the antioxidant activity of tryptamine toward HO● and HOO● radicals in water at 298 K has been carried out. Density functional methods have been employed for the quantum chemical calculations and conventional transition state theory was used for rate constants evaluation. Different mechanisms have been considered: radical adduct formation (RAF), single electron transfer (SET), and hydrogen atom transfer (HAT). For the reaction of tryptamine with the hydroxyl radical nearly all channels are diffusion controlled, and the overall rate constant is very high, 6...
May 18, 2018: Journal of Physical Chemistry. B
Yan Deng, Mei-Fen Bao, Bao-Bao Shi, Jing Wu, Xiang-Hai Cai
Three new monoterpene indole alkaloids, 3α-hydroxymethyl-ibogamine (1), 3α-acetatemethoxyl-ibogamine (2), 16α-hydroxyl-ibogamine (3) together with six known alkaloids were isolated from the branches and leaves of Tabernaemontana divaricata (Apocynaceae). The structures of these alkaloids were determined by spectroscopic analyses. All isolated compounds showed no significant cytotoxicity against SGC-7901 gastric cancer, HeLa, and A-549 lung cancer cell lines (IC50  > 20 µM).
May 12, 2018: Natural Products and Bioprospecting
Jeremy Carlier, Xingxing Diao, Marilyn A Huestis
Clandestine laboratories continue producing new synthetic cannabinoids that mimic and magnify natural cannabinoids effects to circumvent drug scheduling legislation. New synthetic cannabinoids are highly potent and responsible for many acute intoxications and deaths. Characterization of metabolic pathways is critical to identify metabolite markers whose detection can prove intake. BB-22 is a new potent synthetic cannabinoid whose toxicological and metabolic properties are currently unavailable. Analytical methods require constant updating and are challenging due to extensive synthetic cannabinoid metabolism and low marker concentrations...
May 7, 2018: Journal of Pharmaceutical and Biomedical Analysis
Lukas Mogler, Florian Franz, Maurice Wilde, Laura M Huppertz, Sebastian Halter, Verena Angerer, Bjoern Moosmann, Volker Auwärter
Synthetic cannabinoids (SCs) are a structurally diverse class of new psychoactive substances. Most SCs used for recreational purposes are based on indole or indazole core structures. EG-018 (naphthalen-1-yl(9-pentyl-9H-carbazol-3-yl)methanone), EG-2201 ((9-(5-fluoropentyl)-9H-carbazol-3-yl)(naphthalen-1-yl)methanone) and MDMB-CHMCZCA (methyl 2-(9-(cyclohexylmethyl)-9H-carbazole-3-carboxamido)-3,3-dimethylbutanoate) are three representatives of a structural subclass of SCs, characterized by a carbazole core system...
May 4, 2018: Drug Testing and Analysis
Medjda Bellamri, Shun Xiao, Paari Murugan, Christopher J Weight, Robert J Turesky
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), an heterocyclic aromatic amine (HAA) formed in cooked meat, is a rodent and possible human prostate carcinogen. Recently, we identified DNA adducts of PhIP in the genome of prostate cancer patients, but adducts of 2-amino-3, 8-dimethylmidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-9 H-pyrido[2,3-b]indole (AαC), other prominent HAAs formed in cooked meats, were not detected. We have investigated the bioactivation of HAAs by Phase I and II enzymes in the human prostate (LNCaP) cell line using cytotoxicity and DNA adducts as endpoints...
June 1, 2018: Toxicological Sciences: An Official Journal of the Society of Toxicology
Javid A Parray, Azra N Kamili, Sumira Jan, Mohammad Yaseen Mir, Nowsheen Shameem, Bashir A Ganai, Elsayed Fathi Abd Allah, Abeer Hashem, Abdulaziz A Alqarawi
Arnebia benthamii of the family Boraginaceae is a critically endangered nonendemic plant of the Kashmir Himalayas and is used to treat a number of human diseases. The current study was based on developing an in vitro micropropagation protocol vis-à-vis induction of various secondary metabolites under in vitro conditions for the possible biological activity. A tissue culture protocol was developed for A. benthamii for the first time in the Himalayan region using varied combinations and proper media formulations, including various adjuvants: Murashige and Skoog (MS) media, growth hormones, sugars, agar, and so forth...
2018: BioMed Research International
Huiling Wen, Xiaorui Liu, Qing Zhang, Yanfang Deng, Yi Zang, Jianping Wang, Junjun Liu, Qun Zhou, Linzhen Hu, Hucheng Zhu, Chunmei Chen, Yonghui Zhang
Asperochramides A - D (1 - 4), a new natural product and three new indole diketopiperazine alkaloids, along with seven known analogs (5 - 11), were isolated from the ethyl acetate extract of Aspergillus ochraceus. Their structures were elucidated by extensive spectroscopic analyses, ECD calculation, and single-crystal X-ray diffraction analysis. Compounds 3 and 4 represent a rare group of indole diketopiperazine alkaloid with a 3-hydroxyl-2-indolone moiety. The in vitro anti-inflammatory effects of compounds 1 and 3 - 11 were investigated by using LPS-stimulated murine macrophage RAW 264...
April 2018: Chemistry & Biodiversity
Lukas Mogler, Maurice Wilde, Laura M Huppertz, Georg Weinfurtner, Florian Franz, Volker Auwärter
Indole-, indazole-, or azaindole-based synthetic cannabinoids (SCs), bearing a cumyl substituent are a widespread, recreationally used subgroup of new psychoactive substances (NPS). The latest cumyl-derivative, CUMYL-PEGACLONE, emerged in December 2016 on the German drug market. The substance features a novel γ-carboline core structure, which is most likely synthesized to bypass generic legislative approaches to control SCs by prohibiting distinct core structures. Using liquid chromatography-tandem mass spectrometry and liquid chromatography-high resolution mass spectrometry techniques, the main in vivo phase I metabolites of this new substance were detected...
January 3, 2018: Drug Testing and Analysis
Vanessa Vega-García, Adelaida Díaz-Vilchis, Juan Pablo Saucedo-Vázquez, Alejandro Solano-Peralta, Enrique Rudiño-Piñera, Wilhelm Hansberg
CAT-2, a cytosolic catalase-peroxidase (CP) from Neurospora crassa, which is induced during asexual spore formation, was heterologously expressed and characterized. CAT-2 had the Met-Tyr-Trp (M-Y-W) adduct required for catalase activity. Its KM for H2 O2 was micromolar for peroxidase and millimolar for catalase activity. A Em  = -158 mV reduction potential value was obtained and the Soret band shift suggested a mixture of low and high spin ferric iron. CAT-2 EPR spectrum at 10 K indicated an axial and a rhombic component...
February 15, 2018: Archives of Biochemistry and Biophysics
David Reyes Loya, Alexandre Jean, Morgan Cormier, Catherine Fressigné, Stefano Nejrotti, Jérôme Blanchet, Jacques Maddaluno, Michaël De Paolis
The domino anionic fragmentation of 2-nitrophenyl-1,3-cyclohexanediones containing an electrophilic appendage such as aldehyde and epoxide is disclosed. This reaction, initiated by a series of nucleophiles, involves the generation of an intermediate hydroxylate followed by the regioselective formation and fragmentation of an intermediate lactolate into enolate. This strategy, devoid of any protecting group, enlarges the initial ring and provides an original access to decorated 9-membered lactones with a fused indole unit...
February 9, 2018: Chemistry: a European Journal
Angela Paterna, Ruttiros Khonkarn, Silva Mulhovo, Alexis Moreno, Patricia Madeira Girio, Hélène Baubichon-Cortay, Pierre Falson, Maria-José U Ferreira
Aiming at generating a library of bioactive indole alkaloid derivatives as multidrug resistance (MDR) reversers, two epimeric indole alkaloids (1 and 2) were submitted to chemical transformations, giving rise to twenty-four derivatives (5-28), bearing new aromatic or aliphatic azine moieties. The structure of the compounds was established by 1D and 2D NMR (COSY, HMBC, HMQC and NOESY) experiments. Two different strategies were employed for assessing their anti-MDR potential, namely through the evaluation of their activity as inhibitors of typical MDR ABC transporters overexpressed by cell transfection, such as ABCB1 (P-gp), ABCC1 (MRP1), and ABCG2 (BCRP), or by evaluating their ability as collateral sensitivity (CS) agents in cells overexpressing MRP1...
January 15, 2018: Bioorganic & Medicinal Chemistry
Xianjun Liu, Tingting Zhang, Xiang Li, Ge Zhao, Fuwei Xie
2-Amino-9H-pyrido[2,3-b]indole (AαC), which is a hazardous compound present in cigarette smoke, has been listed as probable human carcinogens (Group 2B). The carcinogenicity and genotoxicity of AαC were activated by the process of metabolic bio-activation. Whereas, few studies about genotoxicity induced by AαC have been reported. In this study, we took HepG2 cells as the model to investigate the relationship between oxidative DNA damage induced by AαC and metabolic bio-activation of AαC, which is of importance to unveil the mechanism of AαC genotoxicity...
March 2018: Toxicology Mechanisms and Methods
Jing Li, Cuimei Liu, Tao Li, Zhendong Hua
Since 2012, several cannabimimetic indazole and indole derivatives with valine amino acid amide residue have emerged in the illicit drug market, and have gradually replaced the old generations of synthetic cannabinoids (SCs) with naphthyl or adamantine groups. Among them, ADB-FUBICA [N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indole-3-carboxamide], AB-FUBICA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-(4-fluorobenzyl)-1H-indole-3-carboxamide], AB-BICA [N-(1-amino-3-methyl-1-oxobutan-2-yl)-1-benzyl-1H-indole-3-carboxamide] and ADB-BICA [N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-benzyl-1H-indole-3-carboxamide] were detected in China recently, but unfortunately no information about their in vitro human metabolism is available...
March 2018: Biomedical Chromatography: BMC
Yuhzo Hieda
This review describes the syntheses and antioxidant activities of carbazole alkaloids carquinostatin A, carbazomadurin A and carbazomadurin B and their related carbazoles. The key step was an allene-mediated electrocyclic reaction involving an indole [b]-bond for the construction of a highly substituted carbazole ring. Antioxidant activities of 3-oxygenated and 3,4-dioxygenated carbazole alkaloids and their related carbazoles were comprehensively evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azinobis-(3-ethylbenzthiazoline-6-sulfonate) (ABTS)+ radical scavenging assays, and cupper reducing power...
2017: Yakugaku Zasshi: Journal of the Pharmaceutical Society of Japan
Debarshi Kar Mahapatra, Sanjay Kumar Bharti, Vivek Asati
Chalcone or (E)-1,3-diphenyl-2-propene-1-one scaffold has gained considerable scientific interest in medicinal chemistry owing to its simple chemistry, ease in synthesizing a variety of derivatives and exhibiting a broad range of promising pharmacological activities by modulating several molecular targets. A number of natural and (semi-) synthetic chalcone derivatives have demonstrated admirable anti-inflammatory activity due to their inhibitory potential against various therapeutic targets like Cyclooxygenase (COX), Lipooxygenase (LOX), Interleukins (IL), Prostaglandins (PGs), Nitric Oxide Synthase (NOS), Leukotriene D4 (LTD4), Nuclear Factor-κB (NF- κB), Intracellular Cell Adhesion Molecule-1 (ICAM-1), Vascular Cell Adhesion Molecule-1 (VCAM-1), Monocyte Chemoattractant Protein-1 (MCP-1) and TLR4/MD-2, etc...
November 20, 2017: Current Topics in Medicinal Chemistry
Kai Eggert, Nicolaus von Wirén
Plant hormones (PH) adjust plant growth to environmental conditions such as nutrient availability. Although responses of individual PHs to growth-determining nutrient supplies have been reported, little is known about simultaneous dynamics in the metabolism of different PH species. Brassica napus seedlings were grown under increasing supply of B, and LC-MS/MS was used to characterize bioactive forms of different PH species together with several of their precursors, storage and inactivated forms. Increasing shoot B concentrations in response to B supply were accompanied by decreasing concentrations of abscisic acid (ABA) and indole-3-acetic acid (IAA), which appeared to be synthesized under B deficiency mainly via indole-3-acetonitrile (IAN)...
August 21, 2017: New Phytologist
Joonwon Kim, Pyung-Gang Lee, Eun-Ok Jung, Byung-Gee Kim
Self-sufficient CYP102As possess outstanding hydroxylating activity to fatty acids such as myristic acid. Other CYP102 subfamily members share substrate specificity of CYP102As, but, occasionally, unusual characteristics of its own subfamily have been found. In this study, only one self-sufficient cytochrome P450 from Streptomyces cattleya was renamed from CYP102A_scat to CYP102G4, purified and characterized. UV-Vis spectrometry pattern, FAD/FMN analysis, and protein sequence comparison among CYP102s have shown that CYP102 from Streptomyces cattleya belongs to CYP102G subfamily...
January 2018: Biochimica et Biophysica Acta
Katrin Luck, Qidong Jia, Meret Huber, Vinzenz Handrick, Gane Ka-Shu Wong, David R Nelson, Feng Chen, Jonathan Gershenzon, Tobias G Köllner
Conifers contain P450 enzymes from the CYP79 family that are involved in cyanogenic glycoside biosynthesis. Cyanogenic glycosides are secondary plant compounds that are widespread in the plant kingdom. Their biosynthesis starts with the conversion of aromatic or aliphatic amino acids into their respective aldoximes, catalysed by N-hydroxylating cytochrome P450 monooxygenases (CYP) of the CYP79 family. While CYP79s are well known in angiosperms, their occurrence in gymnosperms and other plant divisions containing cyanogenic glycoside-producing plants has not been reported so far...
September 2017: Plant Molecular Biology
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