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L-methyl tryptophan

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https://www.readbyqxmd.com/read/27998091/tryptophan-lyase-nosl-a-cornucopia-of-5-deoxyadenosyl-radical-mediated-transformations
#1
Dhananjay M Bhandari, Dmytro Fedoseyenko, Tadhg P Begley
Tryptophan lyase (NosL) is a radical S-adenosyl-l-methionine (SAM) enzyme that catalyzes the formation of 3-methyl-2-indolic acid from l-tryptophan. In this paper, we demonstrate that the 5'-deoxyadenosyl radical is considerably more versatile in its chemistry than previously anticipated: hydrogen atom abstraction from Nα-cyclopropyltryptophan occurs at Cα rather than the amino group with NosL Y90A and replacing the substrate amine with a ketone or an alkene changes the chemistry from hydrogen atom abstraction to double bond addition...
December 21, 2016: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/27997749/inhibition-of-platelet-aggregation-and-thrombosis-by-indole-alkaloids-isolated-from-the-edible-insect-protaetia-brevitarsis-seulensis-kolbe
#2
JungIn Lee, Wonhwa Lee, Mi-Ae Kim, Jae Sam Hwang, MinKyun Na, Jong-Sup Bae
Protaetia brevitarsis seulensis (Kolbe) has been temporarily registered as a food material by the Ministry of Food and Drug Safety of Korea (MFDS). The current study aimed to discover small antithrombotic molecules from this edible insect. Five indole alkaloids, 5-hydroxyindolin-2-one (1), (1R,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (2), (1S,3S)-1-methyl-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (3), (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylic acid (4) and L-tryptophan (5), were isolated from the insect...
December 20, 2016: Journal of Cellular and Molecular Medicine
https://www.readbyqxmd.com/read/27973747/quinolinic-acid-induces-neuritogenesis-in-sh-sy5y-neuroblastoma-cells-independently-of-nmda-receptor-activation
#3
Juan-Manuel Hernandez-Martinez, Caroline M Forrest, L Gail Darlington, Robert A Smith, Trevor W Stone
Glutamate and nicotinamide adenine dinucleotide (NAD+) have been implicated in neuronal development and several types of cancer. The kynurenine pathway of tryptophan metabolism includes quinolinic acid (QA) which is both a selective agonist at N-methyl-D-aspartate (NMDA) receptors and also a precursor for the formation of NAD+. The effect of QA on cell survival and differentiation has therefore been examined on SH-SY5Y human neuroblastoma cells. Retinoic acid (RA, 10 μM) induced differentiation of SH-SY5Y cells into a neuronal phenotype showing neurite growth...
December 14, 2016: European Journal of Neuroscience
https://www.readbyqxmd.com/read/27930920/indoleamine-2-3-dioxygenase-regulates-t-cell-activity-through-vav1-rac-pathway
#4
Runmei Li, Hui Li, Qian Sun, Liang Liu, Chen Zhang, Xiubao Ren
The immunoregulatory enzyme indoleamine 2,3-dioxygenase (IDO) suppresses T-cell responses and promotes immune tolerance in tumor resistance. A previous study determined that IDO inhibits Vav1 mRNA expression and the activation of Vav1 and its downstream targets in T cells in the guanine exchange factor (GEF)-independent pathway. The current study aims to determine whether IDO induces T-cell immunosuppression through Vav1/Rac signaling pathway, which is a GEF-dependent pathway. The correlation between Vav1 mRNA expressions in T cells of tumor infiltrating lymphocytes and the levels of IDO expression in lung cancer tissues from lung cancer patients was detected...
January 2017: Molecular Immunology
https://www.readbyqxmd.com/read/27929146/reactivity-of-the-nitrogen-centered-tryptophanyl-radical-in-the-catalysis-by-the-radical-sam-enzyme-nosl
#5
Haocheng Qianzhu, Wenjuan Ji, Xinjian Ji, Leixia Chu, Chuchu Guo, Wei Lu, Wei Ding, Jiangtao Gao, Qi Zhang
The radical SAM tryptophan (Trp) lyase NosL involved in nosiheptide biosynthesis catalyzes two parallel reactions, converting l-Trp to 3-methyl-2-indolic acid (MIA) and to dehydroglycine and 3-methylindole, respectively. The two parallel reactions diverge from a nitrogen-centered tryptophanyl radical intermediate. Here we report an investigation on the intrinsic reactivity of the tryptophanyl radical using a chemical model study and DFT calculations. The kinetics of the formation and fragmentation of this nitrogen-centered radical in NosL catalysis were also studied in detail...
December 22, 2016: Chemical Communications: Chem Comm
https://www.readbyqxmd.com/read/27805190/a-study-of-dna-bsa-interaction-and-catalytic-potential-of-oxidovanadium-v-complexes-with-ono-donor-ligands
#6
Subhashree P Dash, Alok K Panda, Sarita Dhaka, Sagarika Pasayat, Ashis Biswas, Mannar R Maurya, Paresh Kumar Majhi, Aurélien Crochet, Rupam Dinda
The study of DNA/BSA interaction and the catalytic potential of four mononuclear oxidoalkoxido vanadium(v) [V(V)O(L(1-4))OEt] (1-4) and one dinuclear oxidoalkoxido mixed-ligand vanadium(v) [{VO(L(2))OEt}2(Q)]{Q = 4,4'-bipyridine}(5) complexes, with tridentate binegative aroylazine ligands are reported [where H2L(1) = anthranylhydrazone of 2-hydroxy-1-napthaldehyde, H2L(2) = salicylhydrazone of 2-hydroxy-1-napthaldehyde, H2L(3) = benzoylhydrazone of 2-hydroxy-1-acetonaphthone, H2L(4) = anthranylhydrazone of 2-hydroxy-1-acetonaphthone]...
November 2, 2016: Dalton Transactions: An International Journal of Inorganic Chemistry
https://www.readbyqxmd.com/read/27776479/enhanced-metabolic-process-to-indole-alkaloids-in-clematis-terniflora-dc-after-exposure-to-high-level-of-uv-b-irradiation-followed-by-the-dark
#7
Cuixia Gao, Bingxian Yang, Dandan Zhang, Meng Chen, Jingkui Tian
BACKGROUND: Indole alkaloids, which characteristically contain an indole nucleus, have pharmaceutical potential in a diverse range of applications. UV-B can elicit the accumulation of indole alkaloids. The indole alkaloid (6-hydroxyl-1H-indol-3-yl) carboxylic acid methyl ester with cytotoxic activity was found to accumulate in Clematis terniflora DC. leaves after exposure to high level of UV-B irradiation and the dark. However, a more in-depth analysis of the process behind this response has not yet been performed...
October 24, 2016: BMC Plant Biology
https://www.readbyqxmd.com/read/27765857/assessment-of-tryptophan-uptake-and-kinetics-using-1-2-18f-fluoroethyl-l-tryptophan-and-%C3%AE-11c-methyl-l-tryptophan-pet-imaging-in-mice-implanted-with-patient-derived-brain-tumor-xenografts
#8
Sharon K Michelhaugh, Otto Muzik, Anthony R Guastella, Neil V Klinger, Lisa A Polin, Hancheng Cai, Yanchun Xin, Thomas J Mangner, Shaohui Zhang, Csaba Juhasz, Sandeep Mittal
: Abnormal tryptophan metabolism via the kynurenine pathway (KP) is involved in the pathophysiology of a variety of human diseases including cancers. α-[(11)C]-methyl-L-tryptophan ((11)C-AMT) positron emission tomography (PET) imaging demonstrated increased tryptophan uptake and trapping in epileptic foci and brain tumors, but the short half-life of (11)C limits its widespread clinical application. Recent in vitro studies suggested that the novel radiotracer 1-(2-[(18)F]fluoroethyl)-L-tryptophan ((18)F-FETrp) may be useful to assess tryptophan metabolism via the KP...
October 20, 2016: Journal of Nuclear Medicine: Official Publication, Society of Nuclear Medicine
https://www.readbyqxmd.com/read/27755995/the-photobleaching-of-the-free-and-encapsulated-metallic-phthalocyanine-and-its-effect-on-the-photooxidation-of-simple-molecules
#9
Brenda Gomes Fanchiotti, Marcella Piffer Zamprogno Machado, Letícia Camilato de Paula, Mahmut Durmuş, Tebello Nyokong, Arlan da Silva Gonçalves, André Romero da Silva
The photobleaching of an unsubstituted phthalocyanine (gallium(III) phthalocyanine chloride (GaPc)) and a substituted phthalocyanine (1,4-(tetrakis[4-(benzyloxy)phenoxy]phthalocyaninato) indium(III) chloride (InTBPPc)) was monitored for the free photosensitizers and for the phthalocyanines encapsulated into nanoparticles of PEGylated poly(D,L-lactide-co-glycolide) (PLGA-PEG). Phosphate-buffered solutions (PBS) and organic solutions of the free GaPc or the free InTBPPc, and suspensions of each encapsulated photosensitizer (2-15μmol/L) were irradiated using a laser diode of 665nm with a power of 1-104mW and a light dose of 7...
December 2016: Journal of Photochemistry and Photobiology. B, Biology
https://www.readbyqxmd.com/read/27750145/synthesis-spectroscopic-properties-and-photodynamic-activity-of-two-cationic-bodipy-derivatives-with-application-in-the-photoinactivation-of-microorganisms
#10
Maximiliano L Agazzi, M Belén Ballatore, Eugenia Reynoso, Ezequiel D Quiroga, Edgardo N Durantini
Two cationic BODIPYs 3 and 4 were synthesized by acid-catalyzed condensation of the corresponding pyrrole and benzaldehyde, followed by complexation with boron and methylation. Compound 3 contains methyl at the 1,3,5 and 7 positions of the s-indacene ring and a N,N,N-trimethylamino group attached to the phenylene unit, while 4 is not substituted by methyl groups and the cationic group is bound by an aliphatic spacer. UV-visible absorption spectra of these BODIPYs show an intense band at ∼500 nm in solvents of different polarities and n-heptane/sodium bis(2-ethylhexyl)sulfosuccinate (AOT)/water reverse micelles...
October 3, 2016: European Journal of Medicinal Chemistry
https://www.readbyqxmd.com/read/27714299/characterisation-of-6-dmatsmo-from-micromonospora-olivasterospora-leading-to-identification-of-the-divergence-in-enantioselectivity-regioselectivity-and-multiple-prenylation-of-tryptophan-prenyltransferases
#11
Julia Winkelblech, Xiulan Xie, Shu-Ming Li
Prenylated secondary metabolites including indole derivatives usually demonstrate improved biological and pharmacological activities, which make them promising candidates for drug discovery and development. The transfer reactions of a prenyl moiety from a prenyl donor, e.g. dimethylallyl diphosphate (DMAPP), to an acceptor is catalysed by prenyltransferases. One special group of such enzymes uses DMAPP and tryptophan as substrates with dimethylallyltryptophans as reaction products and functions therefore as dimethylallyltryptophan synthases (DMATSs)...
October 18, 2016: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/27707604/synthesis-and-biological-evaluation-of-ricinoleic-acid-based-lipoamino-acid-derivatives
#12
Y Mohini, R B N Prasad, M S L Karuna, Y Poornachandra, C Ganesh Kumar
A series of novel ricinoleic acid based lipoamino acid derivatives were synthesized from (Z)-methyl-12-aminooctadec-9-enoate and different l-amino acids (glycine, alanine, phenyl alanine, valine, leucine, isoleucine, proline and tryptophan). The structures of all the prepared compounds were characterized by (1)H NMR, (13)C NMR and mass spectral studies. The title compounds were evaluated for their antimicrobial and anti-biofilm activities. Among all the derivatives, compound 7a (Z)-methyl-12-(2-aminoacetamido)octadec-9-enoate exhibited promising antibacterial activity (MIC, 3...
September 28, 2016: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/27696676/severity-of-experimental-traumatic-brain-injury-modulates-changes-in-concentrations-of-cerebral-free-amino-acids
#13
Angela Maria Amorini, Giacomo Lazzarino, Valentina Di Pietro, Stefano Signoretti, Giuseppe Lazzarino, Antonio Belli, Barbara Tavazzi
In this study, concentrations of free amino acids (FAA) and amino group containing compounds (AGCC) following graded diffuse traumatic brain injury (mild TBI, mTBI; severe TBI, sTBI) were evaluated. After 6, 12, 24, 48 and 120 hr aspartate (Asp), glutamate (Glu), asparagine (Asn), serine (Ser), glutamine (Gln), histidine (His), glycine (Gly), threonine (Thr), citrulline (Cit), arginine (Arg), alanine (Ala), taurine (Tau), γ-aminobutyrate (GABA), tyrosine (Tyr), S-adenosylhomocysteine (SAH), l-cystathionine (l-Cystat), valine (Val), methionine (Met), tryptophane (Trp), phenylalanine (Phe), isoleucine (Ile), leucine (Leu), ornithine (Orn), lysine (Lys), plus N-acetylaspartate (NAA) were determined in whole brain extracts (n = 6 rats at each time for both TBI levels)...
October 3, 2016: Journal of Cellular and Molecular Medicine
https://www.readbyqxmd.com/read/27681563/structural-determinants-of-nh3-and-nh4-transport-by-mouse-rhbg-a-renal-rh-glycoprotein
#14
Solange Abdulnour-Nakhoul, Trang Le, Edd Rabon, L Lee Hamm, Nazih L Nakhoul
Renal Rhbg is localized to the basolateral membrane of intercalated cells and is involved in NH3/NH4(+) transport. The structure of Rhbg is not yet resolved; however, a high-resolution crystal structure of AmtB, a bacterial homolog of Rh, has been determined. We aligned the sequence of Rhbg to that of AmtB and identified important sites of Rhbg that may affect transport. Our analysis positioned three conserved amino acids, histidine 183 (H183), histidine 342 (H342), and tryptophan 230 (W230), within the hydrophobic pore where they presumably serve to control NH3 transport...
December 1, 2016: American Journal of Physiology. Renal Physiology
https://www.readbyqxmd.com/read/27667153/indoleamine-2-3-dioxygenase-by-degrading-l-tryptophan-enhances-carnitine-palmitoyltransferase%C3%A2-i-activity-and-fatty-acid-oxidation-and-exerts-fatty-acid-dependent-effects-in-human-alloreactive-cd4-t-cells
#15
Theodoros Eleftheriadis, Georgios Pissas, Maria Sounidaki, Konstantina Tsogka, Nikolaos Antoniadis, Georgia Antoniadi, Vassilios Liakopoulos, Ioannis Stefanidis
Indoleamine 2,3-dioxygenase (IDO) is expressed in antigen-presenting cells and by degrading L-tryptophan along the kynurenine pathway suppresses CD4+ T-cell proliferation, induces apoptosis and promotes differentiation towards a regulatory as opposed to an effector phenotype. Recent findings revealed that the above effects may be mediated through alterations in T-cell metabolism. In this study, the effect of IDO on fatty acid β-oxidation in CD4+ T-cells was evaluated in human mixed lymphocyte reactions (MLRs) using the IDO inhibitor, 1-DL-methyl-tryptophan...
November 2016: International Journal of Molecular Medicine
https://www.readbyqxmd.com/read/27572319/inhibiting-tryptophan-metabolism-enhances-interferon-therapy-in-kidney-cancer
#16
Josephine F Trott, Jeffrey Kim, Omran Abu Aboud, Hiromi Wettersten, Benjamin Stewart, Grace Berryhill, Francisco Uzal, Russell C Hovey, Ching-Hsien Chen, Katie Anderson, Ashley Graef, Aaron L Sarver, Jaime F Modiano, Robert H Weiss
Renal cell carcinoma (RCC) is increasing in incidence, and a complete cure remains elusive. While immune-checkpoint antibodies are promising, interferon-based immunotherapy has been disappointing. Tryptophan metabolism, which produces immunosuppressive metabolites, is enhanced in RCC. Here we show indolamine-2,3-dioxygenase-1 (IDO1) expression, a kynurenine pathway enzyme, is increased not only in tumor cells but also in the microenvironment of human RCC compared to normal kidney tissues. Neither kynurenine metabolites nor IDO inhibitors affected the survival or proliferation of human RCC or murine renal cell adenocarcinoma (RENCA) cells in vitro...
October 11, 2016: Oncotarget
https://www.readbyqxmd.com/read/27569181/regional-specific-modulation-of-neuronal-activation-associated-with-nitric-oxide-synthase-inhibitors-in-an-animal-model-of-antidepressant-activity
#17
Eoin Sherwin, Valentina Gigliucci, Andrew Harkin
OBJECTIVE: The regional specific modulation of neuronal activation following drug administration is of interest to determine brain areas involved in the behavioural effects of experimental test compounds. In the current investigation the effects of the L-arginine related NOS inhibitor N(ω)-l-nitroarginine (L-NA) and the structurally unrelated selective neuronal NOS inhibitor 1-(2-Trifluoro-methyl-phenyl) imidazole (TRIM) were assessed in the rat for changes in regional c-FOS immunoreactivity, a marker of neuronal activation, upon exposure to the forced swimming test (FST)...
January 1, 2017: Behavioural Brain Research
https://www.readbyqxmd.com/read/27515561/conformationally-constrained-peptidomimetics-as-inhibitors-of-the-protein-arginine-methyl-transferases
#18
Astrid Knuhtsen, Baptiste Legrand, Olivier Van der Poorten, Muriel Amblard, Jean Martinez, Steven Ballet, Jesper L Kristensen, Daniel Sejer Pedersen
Protein arginine N-methyl transferases (PRMTs) belong to a family of enzymes that modulate the epigenetic code through modifications of histones. In the present study, peptides emerging from a phage display screening were modified in the search for PRMT inhibitors through substitution with non-proteinogenic amino acids, N-alkylation of the peptide backbone, and incorporation of constrained dipeptide mimics. One of the modified peptides (23) showed an increased inhibitory activity towards several PRMTs in the low μm range and the conformational preference of this peptide was investigated and compared with the original hit using circular dichroism and NMR spectroscopy...
September 19, 2016: Chemistry: a European Journal
https://www.readbyqxmd.com/read/27508960/comparison-of-fluoxetine-and-1-methyl-l-tryptophan-in-treatment-of-depression-like-illness-in-bacillus-calmette-guerin-induced-inflammatory-model-of-depression-in-mice
#19
Proteesh Rana, Amit K Sharma, Smita Jain, Pravin Deshmukh, S K Bhattacharya, B D Banerjee, Pramod K Mediratta
BACKGROUND: The inflammatory response system has been implicated in the pathophysiology of major depression. The pro-inflammatory cytokines like interferon-γ induce the enzyme indoleamine-2,3-dioxygenase (IDO) of the kynurenine pathway of tryptophan metabolism. The induction of IDO reduces the availability of tryptophan for serotonin synthesis. Furthermore, the metabolites of kynurenine pathway have neurotoxic property, which along with decreased serotonin may account for depression-like illness...
November 1, 2016: Journal of Basic and Clinical Physiology and Pharmacology
https://www.readbyqxmd.com/read/27487410/targeting-an-aromatic-hotspot-in-plasmodium-falciparum-1-deoxy-d-xylulose-5-phosphate-reductoisomerase-with-%C3%AE-arylpropyl-analogues-of-fosmidomycin
#20
Sanjeewani Sooriyaarachchi, René Chofor, Martijn D P Risseeuw, Terese Bergfors, Jenny Pouyez, Cynthia S Dowd, Louis Maes, Johan Wouters, T Alwyn Jones, Serge Van Calenbergh, Sherry L Mowbray
Blocking the 2-C-methyl-d-erythrithol-4-phosphate pathway for isoprenoid biosynthesis offers new ways to inhibit the growth of Plasmodium spp. Fosmidomycin [(3-(N-hydroxyformamido)propyl)phosphonic acid, 1] and its acetyl homologue FR-900098 [(3-(N-hydroxyacetamido)propyl)phosphonic acid, 2] potently inhibit 1-deoxy-d-xylulose-5-phosphate reductoisomerase (Dxr), a key enzyme in this biosynthetic pathway. Arylpropyl substituents were introduced at the β-position of the hydroxamate analogue of 2 to study changes in lipophilicity, as well as electronic and steric properties...
September 20, 2016: ChemMedChem
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