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Takumi Abe, Koji Yamada
A concise synthesis of the azepinobisindole alkaloid iheyamine A from an indole-2,3-epoxide equivalent has been achieved. This method features a formal C3 electrophilic reaction of an indole-2,3-epoxide equivalent with tryptamine to form a 3-aminoindoline and a novel In-catalyzed dehydrative Mannich-type reaction of the hemiaminal to give the azepinobisindole core.
February 13, 2018: Organic Letters
Ying Wan, Hai-Qing Wang, Meng-Meng Xu, Guang-Jian Mei, Feng Shi
A Brønsted acid-catalyzed direct C3-arylation of 2-indolylmethanols with tryptamines and tryptophols has been established, leading to a series of potentially bioactive 2,3'-biindole derivatives with a broad substrate scope and generally good yields (38 examples, up to 96% yield). In this process, the reactivity of the C3-position of 2-indolylmethanol is switched from nucleophilic to electrophilic, which can serve as an umpolung strategy in indole chemistry. This protocol not only provides a new strategy for accessing structurally diversified 2,3'-biindolyl frameworks, but also satisfies the requirement of green chemistry...
February 12, 2018: Organic & Biomolecular Chemistry
Leena Mattsson, Jingjing Xu, Claudia Preininger, Bernadette Tse Sum Bui, Karsten Haupt
We developed a competitive fluorescent molecularly imprinted polymer (MIP) assay to detect biogenic amines in fish samples. MIPs synthesized by precipitation polymerization using histamine as template were used in a batch binding assay analogous to competitive fluoroimmunoassays. Introducing a complex sample matrix, such as fish extract, into the assay changes the environment and the binding conditions, therefore the importance of the sample preparation is extensively discussed. Several extraction and purification methods for fish were comprehensively studied, and an optimal clean-up procedure for fish samples using liquid-liquid extraction was developed...
May 1, 2018: Talanta
Weigang He, Jiadong Hu, Pengyan Wang, Le Chen, Kai Ji, Siyu Yang, Yin Li, Zhilong Xie, Weiqing Xie
A highly enantioselective tandem Michael addition of oxindole derived from tryptamine to alkynone is developed by taking advantage of Sc(OTf)3-chiral N,N'-dioxide catalyst. The reaction enables facile preparation of enantioenriched spiro[pyrrolidine-3,3'-oxindole], which provides a novel strategy for the synthesis of monoterpenoid indole alkaloids. As a demonstration, the asymmetric synthesis of strychnos alkaloids [(-)-tubifoline, (-)-tubifolidine, (-)-dehydrotubifoline] is achieved in 10-11 steps.
February 8, 2018: Angewandte Chemie
Rosana M Lobayan, María Celia Pérez Schmit
Serotonin (5-hydroxytryptamine, SER) is a neurotransmitter that affects many different processes within the human body. We studied the conformational space of SER, and explored in depth the significant stereoelectronic features for the structure stabilization and antioxidant activity. Forty-eight equilibrium structures were described at the B3LYP/6-311++G(d,p) level, characterizing four non-previously reported conformers. Electron distributions were analyzed by topological QTAIM (Quantum Theory of atoms in molecules) and natural bond orbital (NBO) studies...
January 31, 2018: Journal of Molecular Graphics & Modelling
Runhui Ke, Zongsu Wei, Christian Bogdal, Recep Kaya Göktaş, Ruiyang Xiao
Biogenic amines (BAs), a class of nitrogenous compounds that are frequently detected in wine, pose adverse effects to humans. However, with the largest red wine consumption in the world, little is known about national profiles correlating BAs in wines to toxicological/health risks in China. In this study, we conducted a nationwide survey of commercially available wines for the occurrence of BAs. Our sampling campaign covered >90% of wine brands (n = 456) in China in a three year span (2014-2016). The target BAs included tryptamine, phenylethylamine, putrescine, cadaverine, histamine, tyramine, spermidine and spermine...
June 1, 2018: Food Chemistry
Cinzia Sanna, Daniela Rigano, Angela Corona, Dario Piano, Carmen Formisano, Domenica Farci, Genni Franzini, Mauro Ballero, Giuseppina Chianese, Enzo Tramontano, Orazio Taglialatela-Scafati, Francesca Esposito
During our search for potential templates of HIV-1 reverse transcriptase (RT) and integrase (IN) dual inhibitors, the methanolic extract obtained from aerial parts of Limonium morisianum was investigated. Repeated bioassay-guided chromatographic purifications led to the isolation of the following secondary metabolites: myricetin, myricetin 3-O-rutinoside, myricetin-3-O-(6″-O-galloyl)-β-d-galactopyranoside, (-)-epigallocatechin 3-O-gallate, tryptamine, ferulic and phloretic acids. The isolated compounds were tested on both HIV-1 RT-associated RNase H and IN activities...
February 4, 2018: Natural Product Research
Shu-Rong Chen, Shih-Wei Wang, Chien-Jung Su, Hao-Chun Hu, Yu-Liang Yang, Chi-Ting Hsieh, Chia-Chi Peng, Fang-Rong Chang, Yuan-Bin Cheng
Three new compounds, tuberazines A-C (1-3), and eleven known compounds (4-14) were obtained from the ethanolic extract of Taiwanese zoanthid Palythoa tuberculosa. Compounds 1-4 are rare marine natural products with a pyrazine moiety, and compound 5 is a tricyclic tryptamine derivative isolated from nature for the first time. The structures of all isolated metabolites were determined by analyzing their IR, Mass, NMR, and UV spectrometric data. The absolute configuration of 1 was confirmed by comparing the trend of experimental electronic circular dichroism (ECD) with calculated ECD spectra...
January 31, 2018: Marine Drugs
Ya Fatou Njie-Mbye, Jenaye Robinson, Leah Mitchell-Bush, Marshalyn Mckoy, Catherine A Opere, Sunny E Ohia, Naj Sharif
PURPOSE: To determine the serotonergic (5HT) receptor subtype mediating the contraction of bovine posterior ciliary arteries (BPCAs) in vitro. METHODS: Longitudinal isometric tension was measured in BPCA strips (4-5 mm) mounted in 25 mL organ baths containing oxygenated Krebs solution at 37°C. Cumulative contractile concentration-response (C-R) curves were generated for various 5-HT agonists to assess their potencies and maximal degrees of contraction. Multiple agonist C-R curves were also constructed in the presence and absence of receptor-selective antagonists to determine antagonist potencies using Schild plots...
January 25, 2018: Journal of Ocular Pharmacology and Therapeutics
Sunny E Ohia, Ya Fatou Njie-Mbye, Jenaye Robinson, Leah Mitchell, Marshalyn Mckoy, Catherine A Opere, Naj A Sharif
PURPOSE: To study the pharmacological profile of the serotonin (5-hydroxytryptamine [5-HT]) receptor subtype mediating contractions in bovine isolated ciliary muscles. METHODS: Ciliary muscle strips were isolated from bovine eyeballs and mounted in organ baths containing aerated (95% O2, 5% CO2) Krebs buffer solution maintained at 37°C. Each muscle strip was attached at 1 end to a Grass Force-displacement Transducer connected to a Polyview Computer System for recording changes in isometric tension...
January 24, 2018: Journal of Ocular Pharmacology and Therapeutics
T M Nelson, J C Borgogna, R D Michalek, D W Roberts, J M Rath, E D Glover, J Ravel, M D Shardell, C J Yeoman, R M Brotman
Cigarette smoking has been associated with both the diagnosis of bacterial vaginosis (BV) and a vaginal microbiota lacking protective Lactobacillus spp. As the mechanism linking smoking with vaginal microbiota and BV is unclear, we sought to compare the vaginal metabolomes of smokers and non-smokers (17 smokers/19 non-smokers). Metabolomic profiles were determined by gas and liquid chromatography mass spectrometry in a cross-sectional study. Analysis of the 16S rRNA gene populations revealed samples clustered into three community state types (CSTs) ---- CST-I (L...
January 16, 2018: Scientific Reports
Marigianna Marinou, Dimitrios Platis, Farid S Ataya, Evangelia Chronopoulou, Dimitrios Vlachakis, Nikolaos E Labrou
In the present study, a structure-based approach was exploited for the in silico design of a nucleotide coenzyme mimetic ligand. The enzyme formate dehydrogenase (FDH) was employed as a model in our study. The biomimetic ligand was designed and synthesized based on a tryptamine/3-aminopropylphosphonic acid bi-substituted 1,3,5-triazine (Trz) scaffold (Tra-Trz-3APP), which potentially mimics the interactions of NAD+-FDH complex. Molecular docking studies of the biomimetic ligand predicted that it can occupy the same binding site as the natural coenzyme...
January 3, 2018: Journal of Chromatography. A
Arif Luqman, Mulugeta Nega, Minh-Thu Nguyen, Patrick Ebner, Friedrich Götz
A subgroup of biogenic amines, the so-called trace amines (TAs), are produced by mammals and bacteria and can act as neuromodulators. In the genus Staphylococcus, certain species are capable of producing TAs through the activity of staphylococcal aromatic amino acid decarboxylase (SadA). SadA decarboxylates aromatic amino acids to produce TAs, as well as dihydroxy phenylalanine and 5-hydroxytryptophan to thus produce the neurotransmitters dopamine and serotonin. SadA-expressing staphylococci were prevalent in the gut of most probands, where they are part of the human intestinal microflora...
January 9, 2018: Cell Reports
Alex Inthasot, Nicolas Le Poul, Michel Luhmer, Benoit Colasson, Ivan Jabin, Olivia Reinaud
A water-soluble calix[6]arene-based azacryptand was synthesized. The corresponding tren [tris(2-aminoethyl)amine] cap grafted at the small rim coordinates strongly a copper(II) ion over a wide range of pH. The host-guest properties of the complex were explored by EPR spectroscopy. Due to second coordination sphere effects and the hydrophobic effect ascribed to the calixarene cavity, this funnel complex selectively binds neutral molecules (alcohols, nitriles, amines) versus anions in water near physiological pH...
January 9, 2018: Inorganic Chemistry
Jan Honegr, Rafael Dolezal, David Malinak, Marketa Benkova, Ondrej Soukup, Joyce S F D de Almeida, Tanos C C Franca, Kamil Kuca, Roman Prymula
In order to identify novel lead structures for human toll-like receptor 4 (hTLR4) modulation virtual high throughput screening by a peta-flops-scale supercomputer has been performed. Based on the in silico studies, a series of 12 compounds related to tryptamine was rationally designed to retain suitable molecular geometry for interaction with the hTLR4 binding site as well as to satisfy general principles of drug-likeness. The proposed compounds were synthesized, and tested by in vitro and ex vivo experiments, which revealed that several of them are capable to stimulate hTLR4 in vitro up to 25% activity of Monophosphoryl lipid A...
January 4, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Rinat F Salikov, Konstantin P Trainov, Irina K Belousova, Aleksandr Yu Belyy, Ulyana Sh Fatkullina, Regina V Mulyukova, Liana F Zainullina, Yulia V Vakhitova, Yury V Tomilov
The influence of a series of tryptamine derivatives on the viability of normal (HEK293) and tumor (HepG2, Jurkat and SH-SY5Y) cells has been evaluated. All tryptamines tested were three different substitution types: C- and N-branching, and indole benzylation. All the derivations enhance the activity of compounds separately, although the effects of different substitutions were not additive. Thus, combinations of C- and N-branchings as well as C-branching and indole benzylation gave little or no increase in activity...
December 9, 2017: European Journal of Medicinal Chemistry
Louisa V Forbes, Anthony J Kettle
Myeloperoxidase, an abundant neutrophil enzyme, promotes oxidative damage during inflammation by generating hypohalous acids and free radicals. Currently, there are no selective drugs to inhibit its adverse activity. This short-coming is partly due to the lack of screening assays that mimic the complex enzymatic activities of myeloperoxidase in vivo. We have developed an assay for myeloperoxidase activity that includes its major physiological substrates - chloride, thiocyanate, tyrosine, and urate. The multi-substrate assay monitors bleaching of 5-thio-2-nitrobenzoic acid and measures total oxidant production when hydrogen peroxide activates the enzyme...
December 16, 2017: Analytical Biochemistry
Tomris Ozben, Aysegul Hanikoglu, Ertan Kucuksayan, Rana Cagla Akduman
This systematic review aims to elucidate the role of melatonin (N-acetyl-5-metoxy-tryptamine) (MLT) in the prevention and treatment of cancer. MLT is a pineal gland secretory product, an evolutionarily highly conserved molecule; it is also an antioxidant and an impressive protector of mitochondrial bioenergetic activity. MLT is characterized by an ample range of activities, modulating the physiology and molecular biology of the cell. Its physiological functions relate principally to the interaction of G protein-coupled MT1 and MT2 trans-membrane receptors (GPCRs), a family of guanidine triphosphate binding proteins...
November 21, 2017: Anti-cancer Agents in Medicinal Chemistry
Jia-Chen Xiang, Zi-Xuan Wang, Yan Cheng, Jin-Tian Ma, Miao Wang, Bo-Cheng Tang, Yan-Dong Wu, An-Xin Wu
An expeditious one-step synthesis of the imidazopyridoindole scaffold was achieved through the C-H oxidation/two-fold cyclization reaction of methyl ketone and tryptamine derivatives. Mild oxidizing conditions were employed to realize the efficient oxidative of C(sp3)-H bonds, while suppressing overoxidation of the intermediate and ensuring the cross-trapping of two in situ generated acylimine intermediates.
November 24, 2017: Journal of Organic Chemistry
Yanshi Wang, Jingsheng Lin, Xiaoyu Wang, Guanghui Wang, Xinhang Zhang, Bo Yao, Yuandong Zhao, Pengfei Yu, Bin Lin, Yongxiang Liu, Maosheng Cheng
Ynamide, as a versatile synthetic precursor has gained much attention from synthetic chemists and sparked the development of a number of methodologies in constructing various structures. The 1H-pyrrolo[2,3-d]carbazole was a core scaffold of a series of monoterpene indole alkaloids such as Kopsia, Strychnos and Aspidosperma. In this study, the 1H-pyrrolo[2,3-d]carbazole derivatives were synthesized via a Brønsted acid-catalyzed tandem cyclization from tryptamine-based ynamides. This strategy prevented Wagner-Meerwein rearrangement by an instantaneous intramolecular nucleophilic trap to indoleninium via in situ formed enol species induced by the formation of a more stable conjugate diene moiety...
November 23, 2017: Chemistry: a European Journal
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