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Tryptamine

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https://www.readbyqxmd.com/read/29339821/cigarette-smoking-is-associated-with-an-altered-vaginal-tract-metabolomic-profile
#1
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
https://www.readbyqxmd.com/read/29331223/structure-based-design-and-application-of-a-nucleotide-coenzyme-mimetic-ligand-application-to-the-affinity-purification-of-nucleotide-dependent-enzymes
#2
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
https://www.readbyqxmd.com/read/29320746/sada-expressing-staphylococci-in-the-human-gut-show-increased-cell-adherence-and-internalization
#3
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
https://www.readbyqxmd.com/read/29314855/selective-epr-detection-of-primary-amines-in-water-with-a-calix-6-azacryptand-based-copper-ii-funnel-complex
#4
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
https://www.readbyqxmd.com/read/29300367/rational-design-of-a-new-class-of-toll-like-receptor-4-tlr4-tryptamine-related-agonists-by-means-of-the-structure-and-ligand-based-virtual-screening-for-vaccine-adjuvant-discovery
#5
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
https://www.readbyqxmd.com/read/29274489/branching-tryptamines-as-a-tool-to-tune-their-antiproliferative-activity
#6
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
https://www.readbyqxmd.com/read/29258826/a-multi-substrate-assay-for-finding-physiologically-effective-inhibitors-of-myeloperoxidase
#7
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
https://www.readbyqxmd.com/read/29173185/a-review-on-melatonin%C3%A2-s-effects-in-cancer-potential-mechanisms
#8
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
https://www.readbyqxmd.com/read/29171272/a-c-h-oxidation-two-fold-cyclization-approach-to-imidazopyridoindole-scaffold-under-mild-oxidizing-conditions
#9
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
https://www.readbyqxmd.com/read/29168592/br%C3%A3-nsted-acid-catalyzed-tandem-cyclizations-of-tryptamine-ynamides-yielding-1h-pyrrolo-2-3-d-carbazole-derivatives
#10
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
https://www.readbyqxmd.com/read/29149453/melatonin-and-serotonin-mediators-in-the-symphony-of-plant-morphogenesis
#11
Lauren A E Erland, Mukund R Shukla, Amritpal S Singh, Susan J Murch, Praveen K Saxena
Melatonin and serotonin are important signaling and stress mitigating molecules that play important roles across growth and development in plants. Despite many well-documented responses, a systematic investigation of the entire metabolic pathway (tryptophan, tryptamine and N-acetylserotonin) does not exist, leaving many open questions. The objective of this study was to determine the responses of Hypericum perforatum (L.) to melatonin, serotonin and their metabolic precursors. Two well characterized germplasm lines (#4 and 112) created by mutation and a haploid breeding program were compared to wildtype to identify specific responses...
November 17, 2017: Journal of Pineal Research
https://www.readbyqxmd.com/read/29131485/in-vitro-effects-of-serotonin-melatonin-and-other-related-indole-compounds-on-amyloid-%C3%AE-kinetics-and-neuroprotection
#12
Ruth Hornedo Ortega, Grégory Da Costa, Ana Belén Cerezo, Ana Mª Troncoso, Tristan Richard, Mª Carmen García Parrilla
SCOPE: Amyloid-β peptide (Aβ) is the main component of senile plaques in Alzheimer's disease (AD). The inhibition of Aβ assembly, the destabilisation of Aβ aggregates and the decrease of its cytotoxicity for the prevention of neuronal death are considered neuroprotective effects. In this work, the protective effects against Aβ aggregation and cytotoxicity of eight indolic compounds: tryptophan (Tryp), tryptamine (Trpa), serotonin (Ser), tryptophol (Phol), N-acetylserotonin (Nser), 3-indoleacetic acid (3IA), tryptophan ethyl ester (Tee) and melatonin (Mel) was evaluated...
November 12, 2017: Molecular Nutrition & Food Research
https://www.readbyqxmd.com/read/29130788/complex-action-of-tyramine-tryptamine-and-histamine-on-native-and-recombinant-asics
#13
Oleg I Barygin, Margarita S Komarova, Tatyana B Tikhonova, Anastasiia S Korosteleva, Maxim V Nikolaev, Lev G Magazanik, Denis B Tikhonov
Proton-gated channels of the ASIC family are widely distributed in the mammalian brain, and, according to the recent data, participate in synaptic transmission. However, ASIC-mediated currents are small, and special efforts are required to detect them. This prompts the search for endogenous ASIC ligands, which can activate or potentiate these channels. A recent finding of the potentiating action of histamine on recombinant homomeric ASIC1a has directed attention to amine-containing compounds. In the present study, we have analyzed the action of histamine, tyramine, and tryptamine on native and recombinant ASICs...
November 13, 2017: Channels
https://www.readbyqxmd.com/read/29128711/polysubstance-use-profiles-among-electronic-dance-music-party-attendees-in-new-york-city-and-their-relation-to-use-of-new-psychoactive-substances
#14
Fermín Fernández-Calderón, Charles M Cleland, Joseph J Palamar
BACKGROUND: Electronic Dance Music (EDM) party attendees are often polysubstance users and are at high risk for use of new psychoactive substances (NPS). We sought to identify patterns of use of common illegal drugs among EDM party attendees, sociodemographic correlates, and use of NPS as a function of patterns of use of more common drugs to inform prevention and harm reduction. METHOD: Using time-space-sampling, 1045 individuals aged 18-40 were surveyed entering EDM parties in New York City...
November 4, 2017: Addictive Behaviors
https://www.readbyqxmd.com/read/29095627/total-synthesis-of-geissoschizol-through-ir-catalyzed-allylic-amidation-as-the-key-step
#15
Yu Zheng, Kun Wei, Yu-Rong Yang
The iridium-catalyzed, Zn(OTf)2 promoted asymmetric allylic amidation of a secondary alcohol derived from tryptamine has been utilized to forge a tetrahydro-β-carboline. Based on this key step, a novel, facile, and enantioselective total synthesis of (-)-geissoschizol was achieved in 10 steps.
November 2, 2017: Organic Letters
https://www.readbyqxmd.com/read/29078252/analysis-of-new-psychoactive-substances-in-oral-fluids-by-means-of-microextraction-by-packed-sorbent-followed-by-uhplc-ms-ms
#16
Rachele Rocchi, Maria Chiara Simeoni, Camilla Montesano, Gabriele Vannutelli, Roberta Curini, Manuel Sergi, Dario Compagnone
In recent years, new drugs, commonly known as "new psychoactive substances" (NPS), appeared on the market, which include, among others, synthetic cannabinoids, cathinones and tryptamine analogs of psilocin. The aim of this work was to develop and validate a new method for simultaneous screening and quantification of 31 NPS in oral fluid by ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS). The chosen target analytes represented different chemical and toxicological NPS classes, such as synthetic cathinones, piperazines, phenethylamines, synthetic cannabinoids and their metabolites...
October 27, 2017: Drug Testing and Analysis
https://www.readbyqxmd.com/read/29028555/shifting-characteristics-of-ecstasy-users-ages-12-34-in-the-united-states-2007-2014
#17
Joseph J Palamar, Pia M Mauro, Benjamin H Han, Silvia S Martins
BACKGROUND: Ecstasy/MDMA has been one of the most prevalent party drugs for decades, and powder ecstasy recently increased in popularity. We examined trends in use to determine who to best target for prevention and harm reduction. METHODS: Secondary analysis of the 2007-2014 National Survey on Drug Use and Health, a repeated cross-sectional, nationally representative probability sample, was conducted. Linear trends in past-year ecstasy use and trends in demographic and other past-year substance use characteristics among ecstasy users were examined among participants ages 12-34 (N=332,560)...
December 1, 2017: Drug and Alcohol Dependence
https://www.readbyqxmd.com/read/28977362/stability-indicating-reversed-phase-uhplc-method-development-and-characterization-of-degradation-products-of-almotriptan-maleate-by-lc-qtof-ms-ms
#18
B Saibaba, Ch Vishnuvardhan, P Johnsi Rani, N Satheesh Kumar
Almotriptan maleate (ALMT), a highly selective 5-hydroxy tryptamine 1B/1D (5-HT1B/1D) receptor agonist used in the treatment of migraine headache was subjected to various ICH (Q1A (R2)) specified guidelines. The drug underwent significant degradation under hydrolytic (acid, base and neutral), oxidative and photolytic stress conditions, while it was stable under thermal stress condition. A total of seven significant degradation products (DPs) were obtained. A simple, selective and reliable UPLC method has been developed for the separation of ALMT and its DPs using Acquity UPLC HSS Cyano (100 × 2...
August 30, 2017: Journal of Chromatographic Science
https://www.readbyqxmd.com/read/28956932/selenium-iodine-cooperative-catalyst-for-chlorocyclization-of-tryptamine-derivatives
#19
Takahiro Horibe, Shuhei Ohmura, Kazuaki Ishihara
Chlorocyclization of tryptamine derivatives has been developed with the use of a diphenyl diselenide-iodine cooperative catalyst. Various tryptamine derivatives can be smoothly converted to the corresponding C3a-chlorohexahydropyrrolo[2,3-b]indoles. Additionally, we demonstrate the formal total syntheses of (-)-psychotriasine and (-)-acetylardeemin by introducing nucleophiles to the C3a position of the products.
September 28, 2017: Organic Letters
https://www.readbyqxmd.com/read/28952728/total-synthesis-of-%C3%A2-subincanadine-e-and-determination-of-absolute-configuration
#20
Manojkumar G Kalshetti, Narshinha P Argade
A facile synthesis of (±)-subincanadine E was described from tryptamine-based maleimide. 1,2-Addition of Grignard reagent to maleimide, internal activation of formed lactamol for in situ 1,4-addition of Grignard reagent, and associated position-specific allylic rearrangement in diastereoselective Pictet-Spengler cyclization were the key steps. Enantioselective first total synthesis of naturally occurring cytotoxic (+)-subincanadine E was also accomplished from (S)-acetoxysuccinimide via an unusual syn-addition of cuprate to the α,β-unsaturated lactam...
October 4, 2017: Journal of Organic Chemistry
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