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https://www.readbyqxmd.com/read/29173185/effects-of-melatonin-in-cancer-potential-mechanisms
#1
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
#2
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
#3
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
#4
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
#5
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
#6
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
#7
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
#8
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
#9
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
#10
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
#11
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
#12
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
#13
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
https://www.readbyqxmd.com/read/28947944/anchimerically-activatable-antiviral-protides
#14
Aniekan Okon, Marcos Romário Matos de Souza, Rachit Shah, Raquel Amorim, Luciana Jesus da Costa, Carston R Wagner
This work describes the synthesis and biological evaluation of an anchimerically activated proTide of 2'-C-β-methylguanosine as an inhibitor of dengue virus 2 (DENV-2). The proTide incorporates a chemically cleavable 2-(methylthio)ethyl moiety and a HINT1 hydrolyzable tryptamine phosphoramidate. Inhibition of DENV-2 replication by proTide 6 was 5-fold greater than the parent nucleoside while displaying no apparent cytotoxicity. Furthermore, we demonstrate with a HINT1 inhibitor that the anti DENV-2 activity of the proTide correlates with the activity of HINT1...
September 14, 2017: ACS Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28933078/-advance-in-biosynthesis-of-terpenoid-indole-alkaloids-and-its-regulation-in-catharanthus-roseus
#15
Xue-Jun Kuang, Cai-Xia Wang, Li-Qiu Zou, Xiao-Xuan Zhu, Chao Sun
Catharanthus roseus can produce a variety of terpenoid indole alkaloids (TIA), most of which exhibit strong pharmacological activities. Hence, biosynthesis and regulation of TIA have received recent attention. 3α (S)-strictosidine is an important node in TIA biosynthesis, which is a condensation product of secologanin and tryptamine. The former is produced in iridoid pathway, and the latter is produced in indole pathway. Vindoline and catharanthine, which are produced respectively by 3α (S)-strictosidine via multi-step enzymatic reaction, can form α-3, 4-anhydrovinblastine by the condensation reaction...
November 2016: Zhongguo Zhong Yao za Zhi, Zhongguo Zhongyao Zazhi, China Journal of Chinese Materia Medica
https://www.readbyqxmd.com/read/28932467/crystal-structure-and-dft-study-of-e-n-2-1h-indol-3-yl-eth-yl-1-anthracen-9-yl-methanimine
#16
Md Serajul Haque Faizi, Necmi Dege, Sergey Malinkin, Tetyana Yu Sliva
The title compound, C25H20N2, (I), was synthesized from the condensation reaction of anthracene-9-carbaldehyde and tryptamine in dry ethanol. The indole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 63.56 (8)° with the anthracene ring (r.m.s. deviation = 0.023 Å). There is a short intra-molecular C-H⋯N inter-action present, and a C-H⋯π inter-action involving the two ring systems. In the crystal, the indole H atom forms an inter-molecular N-H⋯π inter-action, linking mol-ecules to form chains along the b-axis direction...
September 1, 2017: Acta Crystallographica. Section E, Crystallographic Communications
https://www.readbyqxmd.com/read/28930453/ab-initio-qm-mm-modeling-of-the-rate-limiting-proton-transfer-step-in-the-deamination-of-tryptamine-by-aromatic-amine-dehydrogenase
#17
Kara E Ranaghan, William G Morris, Laura Masgrau, Kittusamy Senthilkumar, Linus O Johannissen, Nigel S Scrutton, Jeremy N Harvey, Frederick R Manby, Adrian J Mulholland
Aromatic amine dehydrogenase (AADH) and related enzymes are at the heart of debates on the roles of quantum tunneling and protein dynamics in catalysis. The reaction of tryptamine in AADH involves significant quantum tunneling in the rate-limiting proton transfer step, shown by large H/D primary kinetic isotope effects (KIEs), with unusual temperature dependence. We apply correlated ab initio combined quantum mechanics/molecular mechanics (QM/MM) methods, at levels up to local coupled cluster theory (LCCSD(T)/(aug)-cc-pVTZ), to calculate accurate potential energy surfaces for this reaction, which are necessary for quantitative analysis of tunneling contributions and reaction dynamics...
October 17, 2017: Journal of Physical Chemistry. B
https://www.readbyqxmd.com/read/28926757/mn-ii-based-t1-and-t2-potential-mri-contrast-agent-appended-with-tryptamine-recognition-moiety-for-a%C3%AE-plaques
#18
Neeraj Rastogi, Nidhi Tyagi, Ovender Singh, B S Hemanth Kumar, Udai P Singh, Kaushik Ghosh, Raja Roy
We report the synthesis and characterization of manganese(II) complexes having pentadentate ligands L1 (2,6-bis(1-(2-phenyl-2-(pyridin-2-yl)hydrazono)ethyl)pyridine), L2 (methyl 2,6-bis((E)-1-(2-phenyl-2-(pyridin-2yl)hydrazono)ethyl)isonicotinate), L3 (N-(2-(1H-indol-3-yl)ethyl)-2,6-bis((E)-1-(2-phenyl-2-(pyridin2yl)hydrazono)ethyl)isonicotiamide) and their application as dual contrast agents for simultaneous T1 and T2 weighted magnetic resonance imaging. Single crystal analysis of all the complexes [Mn(II)L1, Mn(II)L2 and Mn(II)L3] confirm the formation of novel seven-coordinate manganese complexes with an inner sphere water and perchlorate ion...
September 5, 2017: Journal of Inorganic Biochemistry
https://www.readbyqxmd.com/read/28880094/enantiospecific-synthesis-of-%C3%AE-substituted-tryptamines
#19
Heather N Rubin, Kinney Van Hecke, Jonathan J Mills, Jennifer Cockrell, Jeremy B Morgan
Functionalized tryptamines are targets of interest for development as small molecule therapeutics. The ring opening of aziridines with indoles is a powerful method for tryptamine synthesis where isomer formation can be controlled. 3,5-Dinitrobenzoyl (DNB)-protected aziridines undergo regioselective, enantiospecific ring opening to produce β-substituted tryptamines for a series of indoles. Attack at the more substituted aziridine carbon occurs in an SN2-like fashion to generate DNB-tryptamine products as synthetic precursors...
September 7, 2017: Organic Letters
https://www.readbyqxmd.com/read/28873563/application-of-3-5-bis-trifluoromethyl-phenyl-isothiocyanate-for-the-determination-of-selected-biogenic-amines-by-lc-tandem-mass-spectrometry-and-19-f-nmr
#20
Aneta Jastrzębska, Anna Piasta, Marek Krzemiński, Edward Szłyk
3,5-Bis-(trifluoromethyl)phenyl isothiocyanate, was used as a convenient reagent for the derivatization of histamine, tyramine, tryptamine and 2-phenylethylamine, which eliminates the purification step. The obtained derivatives were determined by liquid chromatography-tandem mass spectrometry (LC-MS/MS). Additionally, the total amount of these amines was determined by (19)F nuclear magnetic resonance analysis. The procedures were optimized and validated for linearity, limit of detection and quantification, intra- and inter-day precision and recovery resulting in good reproducibility and accuracy...
January 15, 2018: Food Chemistry
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