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indole hydroxylation

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https://www.readbyqxmd.com/read/29314750/phase-i-metabolism-of-the-recently-emerged-synthetic-cannabinoid-cumyl-pegaclone-and-detection-in-human-urine-samples
#1
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
https://www.readbyqxmd.com/read/29305053/structure-kinetics-molecular-and-redox-properties-of-a-cytosolic-and-developmentally-regulated-fungal-catalase-peroxidase
#2
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 adduct required for catalase activity. Its KM for H2O2 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...
January 2, 2018: Archives of Biochemistry and Biophysics
https://www.readbyqxmd.com/read/29286174/domino-ring-expansion-regioselective-access-to-9-membered-lactones-with-a-fused-indole-unit-from-2-nitrophenyl-1-3-cyclohexanediones
#3
Michael De Paolis, David Reyes Loya, Alexandre Jean, Morgan Cormier, Catherine Fressigné, Stefano Nejrotti, Jérôme Blanchet, Jacques Maddaluno
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...
December 29, 2017: Chemistry: a European Journal
https://www.readbyqxmd.com/read/29233614/monoterpene-indole-alkaloid-azine-derivatives-as-mdr-reversal-agents
#4
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...
December 2, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/29022416/effects-of-2-amino-9h-pyrido-2-3-b-indole-a%C3%AE-c-metabolic-bio-activation-on-oxidative-dna-damage-in-human-hepatoma-g2-hepg2-cells
#5
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...
October 12, 2017: Toxicology Mechanisms and Methods
https://www.readbyqxmd.com/read/28992356/uplc-hr-ms-ms-based-determination-study-on-the-metabolism-of-four-synthetic-cannabinoids-adb-fubica-ab-fubica-ab-bica-and-adb-bica-by-human-liver-microsomes
#6
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 gradually replaced the old generations of synthetic cannabinoids (SCs) with naphthyl or adamantine groups. Among them, ADB-FUBICA, AB-FUBICA, AB-BICA and ADB-BICA were detected in China recently, but unfortunately no information about their in vitro human metabolism is available for now. Therefore, biomonitoring studies to screen their consumption lack any information about the potential biomarkers (e...
October 9, 2017: Biomedical Chromatography: BMC
https://www.readbyqxmd.com/read/28966267/total-syntheses-of-multi-substituted-carbazole-alkaloids-and-phenolic-related-compounds-and-evaluation-of-their-antioxidant-activities
#7
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
https://www.readbyqxmd.com/read/28914193/chalcone-derivatives-anti-inflammatory-potential-and-molecular-targets-perspectives
#8
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...
September 14, 2017: Current Topics in Medicinal Chemistry
https://www.readbyqxmd.com/read/28833172/response-of-the-plant-hormone-network-to-boron-deficiency
#9
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
https://www.readbyqxmd.com/read/28821467/in-vitro-characterization-of-cyp102g4-from-streptomyces-cattleya-a-self-sufficient-p450-naturally-producing-indigo
#10
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...
August 15, 2017: Biochimica et Biophysica Acta
https://www.readbyqxmd.com/read/28795267/cyp79-p450-monooxygenases-in-gymnosperms-cyp79a118-is-associated-with-the-formation-of-taxiphyllin-in-taxus-baccata
#11
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
https://www.readbyqxmd.com/read/28743672/membrane-bound-human-orphan-cytochrome-p450-2u1-sequence-singularities-construction-of-a-full-3d-model-and-substrate-docking
#12
Lionel Ducassou, Laura Dhers, Gabriella Jonasson, Nicolas Pietrancosta, Jean-Luc Boucher, Daniel Mansuy, François André
BACKGROUND: Human cytochrome P450 2U1 (CYP2U1) is an orphan CYP that exhibits several distinctive characteristics among the 57 human CYPs with a highly conserved sequence in almost all living organisms. METHODS: We compared its protein sequence with those of the 57 human CYPs and constructed a 3D structure of a full-length CYP2U1 model bound to a POPC membrane. We also performed docking experiments of arachidonic acid (AA) and N-arachidonoylserotonin (AS) in this model...
September 2017: Biochimie
https://www.readbyqxmd.com/read/28686036/synthesis-of-thieno-fused-five-and-six-membered-nitrogen-and-oxygen-heterocycles-via-intramolecular-heteroannulation-of-4-5-substituted-3-amino-or-3-hydroxy-2-functionalized-thiophenes
#13
Anand Acharya, Vibha Gautam, Hiriyakkanavar Ila
Diverse general high-yield routes for novel thieno-fused five- and six-membered nitrogen and oxygen heterocycles such as thieno[3,2-b]pyrroles, thieno[3,2-b]furans, thieno[3,2-b]indoles, thieno[3,2-b]benzofurans, thieno[3,2-b]pyridine-5-ones, thieno[3,2-b]pyran-5-ones, thieno[3,2-b]isoquinolin-5-ones, thieno[3,2-b]chromen-5-ones, thieno[3,2-b]quinolin-9-ones, and thieno[3,2-b]chromen-9-ones have been developed via in situ or stepwise intramolecular heteroannulation of newly synthesized 4,5-substituted 3-amino- or 3-hydroxy 2-functionalized thiophenes...
July 18, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28643772/cryptic-indole-hydroxylation-by-a-non-canonical-terpenoid-cyclase-parallels-bacterial-xenobiotic-detoxification
#14
Susann Kugel, Martin Baunach, Philipp Baer, Mie Ishida-Ito, Srividhya Sundaram, Zhongli Xu, Michael Groll, Christian Hertweck
Terpenoid natural products comprise a wide range of molecular architectures that typically result from C-C bond formations catalysed by classical type I/II terpene cyclases. However, the molecular diversity of biologically active terpenoids is substantially increased by fully unrelated, non-canonical terpenoid cyclases. Their evolutionary origin has remained enigmatic. Here we report the in vitro reconstitution of an unusual flavin-dependent bacterial indoloterpenoid cyclase, XiaF, together with a designated flavoenzyme-reductase (XiaP) that mediates a key step in xiamycin biosynthesis...
June 15, 2017: Nature Communications
https://www.readbyqxmd.com/read/28505547/synthesis-of-indole-analogs-as-potent-%C3%AE-glucuronidase-inhibitors
#15
Mohd Syukri Baharudin, Muhammad Taha, Syahrul Imran, Nor Hadiani Ismail, Fazal Rahim, Muhammad Tariq Javid, Khalid Mohammed Khan, Muhammad Ali
Natural products are the main source of motivation to design and synthesize new molecules for drug development. Designing new molecules against β-glucuronidase inhibitory is utmost essential. In this study indole analogs (1-35) were synthesized, characterized using various spectroscopic techniques including (1)H NMR and EI-MS and evaluated for their β-glucuronidase inhibitory activity. Most compounds were identified as potent inhibitors for the enzyme with IC50 values ranging between 0.50 and 53.40μM, with reference to standard d-saccharic acid 1,4-lactone (IC50=48...
June 2017: Bioorganic Chemistry
https://www.readbyqxmd.com/read/28476332/in-vivo-%C3%AE-hydroxylation-of-a-2-alkylindole-antagonist-of-the-oxe-receptor-for-the-eosinophil-chemoattractant-5-oxo-6-8-11-14-eicosatetraenoic-acid-in-monkeys
#16
Shishir Chourey, Qiuji Ye, Chintam Nagendra Reddy, Chantal Cossette, Sylvie Gravel, Matthias Zeller, Irina Slobodchikova, Dajana Vuckovic, Joshua Rokach, William S Powell
We have developed a selective indole antagonist (230) targeting the OXE receptor for the potent eosinophil chemoattractant 5-oxo-ETE (5-oxo-6,8,11,14-eicosatetraenoic acid), that may be useful for the treatment of eosinophilic diseases such as asthma. In previous studies we identified ω2-oxidation of the hexyl side chain of racemic 230 as a major metabolic route in monkeys, but also obtained evidence for another pathway that appeared to involve hydroxylation of the hexyl side chain close to the indole. The present study was designed to investigate the metabolism of the active S-enantiomer of 230 (S230) and to identify the novel hydroxy metabolite and its chirality...
August 15, 2017: Biochemical Pharmacology
https://www.readbyqxmd.com/read/28466505/total-synthesis-of-%C3%A2-corymine
#17
Benxiang Zhang, Xiaoqing Wang, Chao Cheng, Deqian Sun, Chaozhong Li
The first total synthesis of the hexacyclic indole alkaloid (±)-corymine is described. Starting from the readily available N-protected tryptamine, the title compound was achieved in 21 steps in 3.4 % overall yield. Key steps of the synthesis include: a) the addition of a malonate to a 3-bromooxindole to afford 3,3-disubstituted oxindole, b) the formation of a 12-membered cyclic enol ether by intramolecular O-propargylation, immediately followed by propargyl Claisen rearrangement to provide the α-allenyl ketone stereospecifically, c) DMDO oxidation to install a hydroxy group in a highly stereoselective manner, and d) the SmI2 -mediated reductive C-O bond cleavage to remove the α-keto carboxyl group...
May 3, 2017: Angewandte Chemie
https://www.readbyqxmd.com/read/28455676/metabolic-profile-of-synthetic-cannabinoids-5f-pb-22-pb-22-xlr-11-and-ur-144-by-cunninghamella-elegans
#18
Shimpei Watanabe, Unnikrishnan Kuzhiumparambil, My Ann Nguyen, Jane Cameron, Shanlin Fu
The knowledge of metabolic profile of synthetic cannabinoids is important for the detection of drugs in urinalysis due to the typical absence or low abundance of parent cannabinoids in human urine. The fungus Cunninghamella elegans has been reported to be a useful tool for metabolism study and thus applicability to synthetic cannabinoid metabolism was examined. In this study, 8-quinolinyl 1-(5-fluoropentyl)-1H-indole-3-carboxylate (5F-PB-22), 8-quinolinyl 1-pentyl-1H-indole-3-carboxylate (PB-22), [1-(5-fluoropentyl)-1H-indol-3-yl](2,2,3,3-tetramethylcyclopropyl)methanone (XLR-11) and (1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone (UR-144) were incubated with C...
July 2017: AAPS Journal
https://www.readbyqxmd.com/read/28443122/membrane-proteomics-of-arabidopsis-glucosinolate-mutants-cyp79b2-b3-and-myb28-29
#19
Islam Mostafa, Mi-Jeong Yoo, Ning Zhu, Sisi Geng, Craig Dufresne, Maged Abou-Hashem, Maher El-Domiaty, Sixue Chen
Glucosinolates (Gls) constitute a major group of natural metabolites represented by three major classes (aliphatic, indolic and aromatic) of more than 120 chemical structures. In our previous work, soluble proteins and metabolites in Arabidopsis mutants deficient of aliphatic (myb28/29) and indolic Gls (cyp79B2B3) were analyzed. Here we focus on investigating the changes at the level of membrane proteins in these mutants. Our LC/MS-MS analyses of tandem mass tag (TMT) labeled peptides derived from the cyp79B2/B3 and myb28/29 relative to wild type resulted in the identification of 4,673 proteins, from which 2,171 are membrane proteins...
2017: Frontiers in Plant Science
https://www.readbyqxmd.com/read/28437060/high-throughput-and-quantitative-measurement-of-microbial-metabolome-by-gas-chromatography-mass-spectrometry-using-automated-alkyl-chloroformate-derivatization
#20
Linjing Zhao, Yan Ni, Mingming Su, Hongsen Li, Fangcong Dong, Wenlian Chen, Runmin Wei, Lulu Zhang, Seu Ping Guiraud, Francois-Pierre Martin, Cynthia Rajani, Guoxiang Xie, Wei Jia
The ability to identify and quantify small molecule metabolites derived from gut microbial-mammalian cometabolism is essential for the understanding of the distinct metabolic functions of the microbiome. To date, analytical protocols that quantitatively measure a complete panel of microbial metabolites in biological samples have not been established but are urgently needed by the microbiome research community. Here, we report an automated high-throughput quantitative method using a gas chromatography/time-of-flight mass spectrometry (GC/TOFMS) platform to simultaneously measure over one hundred microbial metabolites in human serum, urine, feces, and Escherichia coli cell samples within 15 min per sample...
May 16, 2017: Analytical Chemistry
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