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Tryptamines

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https://www.readbyqxmd.com/read/27899931/melatonin-in-plants-and-plant-culture-systems-variability-stability-and-efficient-quantification
#1
Lauren A E Erland, Abhishek Chattopadhyay, Andrew Maxwell P Jones, Praveen K Saxena
Despite growing evidence of the importance of melatonin and serotonin in the plant life, there is still much debate over the stability of melatonin, with extraction and analysis methods varying greatly from lab to lab with respect to time, temperature, light levels, extraction solvents, and mechanical disruption. The variability in methodology has created conflicting results that confound the comparison of studies to determine the role of melatonin in plant physiology. We here describe a fully validated method for the quantification of melatonin, serotonin and their biosynthetic precursors: tryptophan, tryptamine and N-acetylserotonin by liquid chromatography single quadrupole mass spectrometry (LC-MS) in diverse plant species and tissues...
2016: Frontiers in Plant Science
https://www.readbyqxmd.com/read/27856348/a-novel-quinone-derived-from-5-hydroxyindoleacetic-acid-reacts-with-protein-possible-participation-of-oxidation-of-serotonin-and-its-metabolite-in-the-development-of-atherosclerosis
#2
Yoji Kato, Kota Oki, Naoko Suga, Shigeki Ono, Akari Ishisaka, Yoko Miura, Satoshi Kanazawa, Michitaka Naito, Noritoshi Kitamoto, Anthony J Kettle
The modification of 5-hydroxyindoleacetic acid (5HIAA) by myeloperoxidase with a xanthine oxidase system was investigated by chromatographic analyses. Two major products were identified as a dimer and quinone (indoleacetate dione) of 5HIAA. The formation of a quinone moiety was also confirmed by chemical trapping with o-phenylenediamine. In the presence of N-acetyl-cysteine (NAC), a quinone-NAC adduct was formed. When glyceraldehyde 3-phosphate dehydrogenase was exposed to the myeloperoxidase system with 5HIAA, quinone adducts were formed on the protein molecule...
November 14, 2016: Free Radical Biology & Medicine
https://www.readbyqxmd.com/read/27847955/far-infrared-spectra-of-the-tryptamine-a-conformer-by-ir-uv-ion-gain-spectroscopy
#3
Michael Schmitt, Frans Spiering, Vitali Zhaunerchyk, Rienk T Jongma, Sander Jaeqx, Anouk M Rijs, Wim J van der Zande
We present far infrared spectra of the conformer A of tryptamine in the 200 to 500 cm(-1) wavenumber range along with resonant photoionization spectra of the far-infrared excited conformer A of tryptamine. We show that single-far-infrared photon excited tryptamine has highly structured resonance enhanced multi-photon ionization spectra, revealing the mode composition of the S1-state. Upon multiple-far-infrared photon absorption, the resonance enhanced multi-photon ionization spectrum broadens allowing ion gain spectroscopy to be performed...
November 30, 2016: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/27845784/antibody-purification-via-affinity-membrane-chromatography-method-utilizing-nucleotide-binding-site-targeting-with-a-small-molecule
#4
Nur Mustafaoglu, Tanyel Kiziltepe, Basar Bilgicer
Here, we present an affinity membrane chromatography technique for purification of monoclonal and polyclonal antibodies from cell culture media of hybridomas and ascites fluids. The m-NBST method utilizes the nucleotide-binding site (NBS) that is located on the Fab variable domain of immunoglobulins to enable capturing of antibody molecules on a membrane affinity column via a small molecule, tryptamine, which has a moderate binding affinity to the NBS. Regenerated cellulose membrane was selected as a matrix due to multiple advantages over traditionally used resin-based affinity systems...
November 15, 2016: Analyst
https://www.readbyqxmd.com/read/27816487/arylalkylamine-n-acetyltransferase-1-gene-tcaanat1-is-required-for-cuticle-morphology-and-pigmentation-of-the-adult-red-flour-beetle-tribolium-castaneum
#5
Mi Young Noh, Bonwoo Koo, Karl J Kramer, Subbaratnam Muthukrishnan, Yasuyuki Arakane
In the insect cuticle tanning pathway (sclerotization and pigmentation), the enzyme arylalkylamine N-acetyltransferase (AANAT) catalyzes the acetylation of dopamine to form N-acetyldopamine (NADA), which is one of the major precursors for quinone-mediated tanning. In this study we characterized and investigated the function of TcAANAT1 in cuticle pigmentation of the red flour beetle, Tribolium castaneum. We isolated a full length TcAANAT1 cDNA that encodes a protein of 256 amino acid residues with a predicted GCN5-related acetyltransferase domain containing an acetyl-CoA binding motif...
November 2, 2016: Insect Biochemistry and Molecular Biology
https://www.readbyqxmd.com/read/27791398/timing-of-glucocorticoid-administration-determines-severity-of-lipid-metabolism-and-behavioral-effects-in-rats
#6
Tao Wu, Jianguo Jiang, Luna Yang, Haifeng Li, Wanjing Zhang, Yangyang Chen, Binggong Zhao, Boda Kong, Ping Lu, Zhenzhen Zhao, Jiawei Zhu, Zhengwei Fu
Glucocorticoids (GCs) are a group of steroid hormones secreted by the adrenal glands in circadian cycles, and the dysregulation of GC signaling has been suggested to cause metabolic syndrome. Even though prolonged GC exposure is associated with serious side effects such as metabolic syndrome and central nervous system disorders, the use of GCs in anti-inflammatory and immunosuppressive therapies has been continuously rising. Meanwhile, the exact mechanisms by which GCs can influence the lipid metabolism as well as behavior and how they are affected by time remain unknown...
October 28, 2016: Chronobiology International
https://www.readbyqxmd.com/read/27777099/longevity-study-with-low-doses-of-selegiline-deprenyl-and-2r-1-1-benzofuran-2-yl-n-propylpentane-2-amine-bpap
#7
J Knoll, I Miklya
AIMS: The first longevity study demonstrating that rats treated with the MAO-B inhibitory dose of (-)-deprenyl (0.25mg/kg) lived significantly longer than their saline-treated peers was published in 1988, and corroborated in many papers. The recent findings that (-)-deprenyl is primarily a PEA-derived synthetic catecholaminergic activity enhancersubstance; (2R)-1-(1-benzofuran-2-yl)-N-propylpentane-2-amine (BPAP) is a tryptamine-derived synthetic enhancer substance, initiated our first longevity study on rats with low enhancer doses of (-)-deprenyl and BPAP to test the enhancer effect's role inlife extension...
October 21, 2016: Life Sciences
https://www.readbyqxmd.com/read/27773294/in-situ-sonochemical-reduction-and-direct-functionalization-of-graphene-oxide-a-robust-approach-with-thermal-and-biomedical-applications
#8
Shrikant S Maktedar, Shantilal S Mehetre, Gopal Avashthi, Man Singh
The rapid, robust, scalable and non-hazardous sonochemical approach for in situ reduction and direct functionalization of graphene oxide has been developed for non-toxic biomedical applications. The graphene oxide (GrO) was directly functionalized with tryptamine (TA) without using any hazardous acylating and coupling reagents. The reaction was completed within 20min. An impact of ultrasound was inferred for a direct functionalization with other conventional methods. The evolved electronic states were confirmed with near edge X-ray absorption fine structure (NEXAFS)...
January 2017: Ultrasonics Sonochemistry
https://www.readbyqxmd.com/read/27746742/molecular-mechanisms-of-obesity-induced-osteoporosis-and-muscle-atrophy
#9
Bipradas Roy, Mary E Curtis, Letimicia S Fears, Samuel N Nahashon, Hugh M Fentress
Obesity and osteoporosis are two alarming health disorders prominent among middle and old age populations, and the numbers of those affected by these two disorders are increasing. It is estimated that more than 600 million adults are obese and over 200 million people have osteoporosis worldwide. Interestingly, both of these abnormalities share some common features including a genetic predisposition, and a common origin: bone marrow mesenchymal stromal cells. Obesity is characterized by the expression of leptin, adiponectin, interleukin 6 (IL-6), interleukin 10 (IL-10), monocyte chemotactic protein-1 (MCP-1), tumor necrosis factor-alpha (TNF-α), macrophage colony stimulating factor (M-CSF), growth hormone (GH), parathyroid hormone (PTH), angiotensin II (Ang II), 5-hydroxy-tryptamine (5-HT), Advance glycation end products (AGE), and myostatin, which exert their effects by modulating the signaling pathways within bone and muscle...
2016: Frontiers in Physiology
https://www.readbyqxmd.com/read/27722446/synthesis-of-polycyclic-spiroindolines-by-highly-diastereoselective-interrupted-ugi-cascade-reactions-of-3-2-isocyanoethyl-indoles
#10
Jordy M Saya, Barry Oppelaar, Răzvan C Cioc, Gydo van der Heijden, Christophe M L Vande Velde, Romano V A Orru, Eelco Ruijter
We report a highly diastereoselective interrupted Ugi reaction to construct a broad range of structurally congested and stereochemically complex spiroindolines from tryptamine-derived isocyanides. The reaction is facilitated by using fluorinated alcohols (TFE or HFIP) as solvents and tolerates a broad range of amines, aldehydes and 2-isocyanoethylindoles to give polycyclic products in moderate to excellent yields.
October 13, 2016: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/27704854/synthesis-of-the-azepinobisindole-alkaloid-iheyamine-a-enabled-by-a-cross-mannich-reaction
#11
Ashley C Lindsay, Ivanhoe K H Leung, Jonathan Sperry
The total synthesis of the azepinobisindole alkaloid iheyamine A is described. The successful strategy hinged on an intermolecular cross-Mannich reaction between 5-methoxy-3-acetoxyindole and a protected tryptamine to access an unsymmetrical 2,2'-bisindole, which was subsequently converted into iheyamine A via a deep-blue 3-indolone intermediate. VT (1)H NMR infers that iheyamine A exists as a mixture of tautomers that undergo intermediate chemical exchange on the NMR time scale. The intermolecular cross-Mannich reaction described herein is a viable alternative to metal-catalyzed cross-coupling strategies commonly employed to access 2,2'-bisindoles...
October 5, 2016: Organic Letters
https://www.readbyqxmd.com/read/27665567/new-psychoactive-substances-an-overview-on-recent-publications-on-their-toxicodynamics-and-toxicokinetics
#12
REVIEW
Markus R Meyer
This review article covers English-written and PubMed-listed review articles and original studies published between January 2015 and April 2016 dealing with the toxicodynamics and toxicokinetics of new psychoactive substances. Compounds covered include stimulants and entactogens, synthetic cannabinoids, tryptamines, NBOMes, phencyclidine-like drugs, benzodiazepines, and opioids. First, an overview and discussion is provided on timely review articles followed by an overview and discussion on recent original studies...
October 2016: Archives of Toxicology
https://www.readbyqxmd.com/read/27643564/phosphorylated-myosin-light-chain-2-p-mlc2-as-a-molecular-marker-of-antemortem-coronary-artery-spasm
#13
Liliang Li, Yuhua Li, Junyi Lin, Jieqing Jiang, Meng He, Daming Sun, Ziqin Zhao, Yiwen Shen, Aimin Xue
BACKGROUND It is not uncommon that only mild coronary artery stenosis is grossly revealed after a system autopsy. While coronary artery spasm (CAS) is the suspected mechanism of these deaths, no specific biomarker has been identified to suggest antemortem CAS. MATERIAL AND METHODS To evaluate the potential of using phosphorylated myosin light chain 2 (p-MLC2) as a diagnostic marker of antemortem CAS, human vascular smooth muscle cells (VSMCs) were cultured and treated with common vasoconstrictors, including prostaglandins F2α (PGF2α), acetylcholine (ACh), and 5-hydroxy tryptamine (5-HT)...
September 19, 2016: Medical Science Monitor: International Medical Journal of Experimental and Clinical Research
https://www.readbyqxmd.com/read/27639368/identification-of-an-indol-based-derivative-as-potent-and-selective-varicella-zoster-virus-vzv-inhibitor
#14
Simona Musella, Veronica di Sarno, Tania Ciaglia, Marina Sala, Antonia Spensiero, Maria Carmina Scala, Carmine Ostacolo, Graciela Andrei, Jan Balzarini, Robert Snoeck, Ettore Novellino, Pietro Campiglia, Alessia Bertamino, Isabel M Gomez-Monterrey
We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the indole nucleus. Modifications of this template through Mannich and Friedel-Crafts reactions, coupled with nucleophilic displacement and reductive aminations led to 23 final derivatives, which were pharmacologically tested. Tryptamine derivative 17a was found to have a selective inhibitory activity against human varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses...
September 7, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27637883/selection-of-amine-oxidizing-dairy-lactic-acid-bacteria-enzyme-and-gene-involved-in-the-decrease-of-biogenic-amines
#15
Rosa Guarcello, Maria De Angelis, Luca Settanni, Sabino Formiglio, Raimondo Gaglio, Fabio Minervini, Giancarlo Moschetti, Marco Gobbetti
: Accumulation of biogenic amines (BAs) in cheese and other foods is a matter of public health concern. This study aimed at identifying enzyme activities responsible for BAs degradation in lactic acid bacteria, which were previously isolated from traditional Sicilian and Apulian cheeses. Selected strains would control the concentration of BAs during cheese manufacture. First, 431 isolates, not showing genes encoding for decarboxylases responsible for BA formation, were selected using PCR-based methods...
September 16, 2016: Applied and Environmental Microbiology
https://www.readbyqxmd.com/read/27631575/multivariate-optimization-of-the-hollow-fibre-liquid-phase-microextraction-of-muscimol-in-human-urine-samples
#16
Somandla Ncube, Anna Poliwoda, Hlanganani Tutu, Piotr Wieczorek, Luke Chimuka
A liquid phase microextraction based on hollow fibre followed by liquid chromatographic determination was developed for the extraction and quantitation of the hallucinogenic muscimol from urine samples. Method applicability on polar hallucinogens was also tested on two alkaloids, a psychedelic hallucinogen, tryptamine and a polar amino acid, tryptophan which exists in its charged state in the entire pH range. A multivariate design of experiments was used in which a half fractional factorial approach was applied to screen six factors (donor phase pH, acceptor phase HCl concentration, carrier composition, stirring rate, extraction time and salt content) for their extent of vitality in carrier mediated liquid microextractions...
October 15, 2016: Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences
https://www.readbyqxmd.com/read/27600803/melatonin-biosynthesis-in-plants-multiple-pathways-catalyze-tryptophan-to-melatonin-in-the-cytoplasm-or-chloroplasts
#17
Kyoungwhan Back, Dun-Xian Tan, Russel J Reiter
Melatonin is an animal hormone as well as a signaling molecule in plants. It was first identified in plants in 1995, and almost all enzymes responsible for melatonin biosynthesis had already been characterized in these species. Melatonin biosynthesis from tryptophan requires four-step reactions. However, six genes, i.e., TDC, TPH, T5H, SNAT, ASMT, and COMT, have been implicated in the synthesis of melatonin in plants, suggesting the presence of multiple pathways. Two major pathways have been proposed based on the enzyme kinetics: one is the tryptophan/tryptamine/serotonin/N-acetylserotonin/melatonin pathway, which may occur under normal growth conditions; the other is the tryptophan/tryptamine/serotonin/5-methoxytryptamine/melatonin pathway, which may occur when plants produce large amounts of serotonin, e...
September 7, 2016: Journal of Pineal Research
https://www.readbyqxmd.com/read/27597409/a-new-scaffold-of-topoisomerase-i-inhibitors-design-synthesis-and-biological-evaluation
#18
Alberto Mazza, Egle M Beccalli, Alessandro Contini, Aida Nelly Garcia-Argaez, Lisa Dalla Via, Maria Luisa Gelmi
The synthesis of a new hexacyclic system was realized starting from tryptamines and exploiting as a key step a sequential Pd-catalyzed N-arylation/acylation reaction. Having topoisomerases as biological target and the campthotecins class as benchmark, the new scaffold was decorated with substituents having different polarity and tested as Topoisomerase I inhibitors.
August 23, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27573798/spiro-pyrrolidine-3-3%C3%A2-oxindole-as-potent-anti-breast-cancer-compounds-their-design-synthesis-biological-evaluation-and-cellular-target-identification
#19
Santanu Hati, Sayantan Tripathy, Pratip Kumar Dutta, Rahul Agarwal, Ramprasad Srinivasan, Ashutosh Singh, Shailja Singh, Subhabrata Sen
The spiro[pyrrolidine-3, 3´-oxindole] moiety is present as a core in number of alkaloids with substantial biological activities. Here in we report design and synthesis of a library of compounds bearing spiro[pyrrolidine-3, 3´-oxindole] motifs that demonstrated exceptional inhibitory activity against the proliferation of MCF-7 breast cancer cells. The synthesis involved a one pot Pictet Spengler-Oxidative ring contraction of tryptamine to the desired scaffolds and occurred in 1:1 THF and water with catalytic trifluoroacetic acid and stoichiometric N-bromosuccinimide as an oxidant...
2016: Scientific Reports
https://www.readbyqxmd.com/read/27570519/technological-factors-affecting-biogenic-amine-content-in-foods-a-review
#20
REVIEW
Fausto Gardini, Yesim Özogul, Giovanna Suzzi, Giulia Tabanelli, Fatih Özogul
Biogenic amines (BAs) are molecules, which can be present in foods and, due to their toxicity, can cause adverse effects on the consumers. BAs are generally produced by microbial decarboxylation of amino acids in food products. The most significant BAs occurring in foods are histamine, tyramine, putrescine, cadaverine, tryptamine, 2-phenylethylamine, spermine, spermidine, and agmatine. The importance of preventing the excessive accumulation of BAs in foods is related to their impact on human health and food quality...
2016: Frontiers in Microbiology
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