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S-Adenosyl methionine

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https://www.readbyqxmd.com/read/28927791/design-and-synthesis-of-novel-prmt1-inhibitors-and-investigation-of-their-binding-preferences-using-molecular-modelling
#1
Hao Yang, Yifan Ouyang, Hao Ma, Hui Cong, Chunlin Zhuang, Wun-Taai Lok, Zhe Wang, Xuanli Zhu, Yutong Sun, Wei Hong, Hao Wang
Protein arginine methyltransferase 1 (PRMT1) catalyses the methylation of substrate arginine by transferring the methyl group from SAM (S-adenosyl-l-methionine), which leads to the formation of S-adenosyl homocysteine (SAH) and methylated arginine. We have shown previously that the Asp84 on PRMT1 could be a potential inhibitor binding site. In the current study, 28 compounds were designed and synthesized that were predicted to bind the Asp84 and substrate arginine sites together. Among them, 6 compounds were identified as potential PRMT1 inhibitors, and showed strong inhibitory effects on cancer cell lines, especially HepG2...
September 8, 2017: Bioorganic & Medicinal Chemistry Letters
https://www.readbyqxmd.com/read/28923203/epigenetic-silencing-of-mirna-34a-in-human-cholangiocarcinoma-via-ezh2-and-dna-methylation-impact-on-regulation-of-notch-pathway
#2
Hyunjoo Kwon, Kyoungsub Song, Chang Han, Jinqiang Zhang, Lu Lu, Weina Chen, Tong Wu
Aberrant expression and regulation of miRNAs have been implicated in multiple stages of tumorigenic processes. The current study was designed to explore the biological function and epigenetic regulation of miR-34a in human cholangiocarcinoma (CCA). Our data show that the expression of miR-34a is decreased significantly in CCA cells compared with non-neoplastic biliary epithelial cells. Forced overexpression of miR-34a in CCA cells inhibited their proliferation and clonogenic capacity in vitro, and suppressed tumor xenograft growth in severe combined immunodeficiency mice...
October 2017: American Journal of Pathology
https://www.readbyqxmd.com/read/28920931/single-molecule-fret-reveals-the-energy-landscape-of-the-full-length-sam-i-riboswitch
#3
Christoph Manz, Andrei Yu Kobitski, Ayan Samanta, Bettina G Keller, Andres Jäschke, G Ulrich Nienhaus
S-adenosyl-L-methionine (SAM) ligand binding induces major structural changes in SAM-I riboswitches, through which gene expression is regulated via transcription termination. Little is known about the conformations and motions governing the function of the full-length Bacillus subtilis yitJ SAM-I riboswitch. Therefore, we have explored its conformational energy landscape as a function of Mg(2+) and SAM ligand concentrations using single-molecule Förster resonance energy transfer (smFRET) microscopy and hidden Markov modeling analysis...
September 18, 2017: Nature Chemical Biology
https://www.readbyqxmd.com/read/28902839/sam-dependent-enzyme-catalysed-pericyclic-reactions-in-natural-product-biosynthesis
#4
Masao Ohashi, Fang Liu, Yang Hai, Mengbin Chen, Man-Cheng Tang, Zhongyue Yang, Michio Sato, Kenji Watanabe, K N Houk, Yi Tang
Pericyclic reactions-which proceed in a concerted fashion through a cyclic transition state-are among the most powerful synthetic transformations used to make multiple regioselective and stereoselective carbon-carbon bonds. They have been widely applied to the synthesis of biologically active complex natural products containing contiguous stereogenic carbon centres. Despite the prominence of pericyclic reactions in total synthesis, only three naturally existing enzymatic examples (the intramolecular Diels-Alder reaction, and the Cope and the Claisen rearrangements) have been characterized...
September 13, 2017: Nature
https://www.readbyqxmd.com/read/28902392/expanding-the-clinical-and-molecular-spectrum-of-prmt7-mutations-three-additional-patients-and-review
#5
Emanuele Agolini, Maria Lisa Dentici, Emanuele Bellacchio, Viola Alesi, Francesca Clementina Radio, Annalaura Torella, Francesco Musacchia, Marco Tartaglia, Bruno Dallapiccola, Vincenzo Nigro, Maria Cristina Digilio, Antonio Novelli
Protein arginine methyltransferase 7 (PRMT7) is a member of a family of enzymes that catalyze the transfer of methyl groups from S-adenosyl-l-methionine to nitrogen atoms on arginine residues. Arginine methylation is involved in multiple biological processes, such as signal transduction, mRNA splicing, transcriptional control, DNA repair, and protein translocation. Currently, seven patients have been described harboring compound heterozygous or homozygous variants in the PRMT7 gene, causing a novel intellectual disability syndrome, known as SBIDDS syndrome (Short Stature, Brachydactyly, Intellectual Developmental Disability, and Seizures)...
September 13, 2017: Clinical Genetics
https://www.readbyqxmd.com/read/28901357/an-ortho-c-methylation-o-glycosylation-motif-on-a-hydroxy-coumarin-scaffold-selectively-installed-by-biocatalysis
#6
Alexander Gutmann, Margaretha Schiller, Mandana Gruber-Khadjawi, Bernd Nidetzky
Various bioactive natural products, like the aminocoumarin antibiotics novobiocin and coumermycin, exhibit an aromatic C-methyl group adjacent to a glycosylated phenolic hydroxyl group. Therefore, tailoring of basic phenolic scaffolds to contain the intricate C-methyl/O-glycosyl motif is of high interest for structural and functional diversification of natural products. We demonstrate site-selective 8-C-methylation and 7-O-β-d-glucosylation of 4,5,7-trihydroxy-3-phenyl-coumarin (1) by S-adenosyl-l-methionine dependent C-methyltransferase (from Streptomyces niveus) and uridine 5'-diphosphate glucose dependent glycosyltransferase from apple (Malus × domestica)...
September 13, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28878744/guanidine-n-methylation-by-blsl-is-dependent-on-acylation-of-beta-amine-arginine-in-the-biosynthesis-of-blasticidin-s
#7
Xiankun Wang, Aiqin Du, Guiyang Yu, Zixin Deng, Xinyi He
The peptidyl nucleoside blasticidin S (BS) produced by Streptomyces griseochromogenes was the first non-mercurial fungicide used to prevent rice blast and increasingly used as a selection reagent in transgenic study. Acylation by addition of a leucine residue at the beta amine group of arginine side chain of demethylblasticidin S (DBS) has been proposed as a novel self-resistance to the cytotoxic biosynthetic intermediate. But the resultant product leucyldemethylblasticidin S (LDBS) has not been isolated as a metabolite, and LDBS synthetase activity remained to be demonstrated in S...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28876898/structural-basis-of-the-selectivity-of-genn-an-aminoglycoside-n-methyltransferase-involved-in-gentamicin-biosynthesis
#8
Priscila Dos Santos Bury, Fanglu Huang, Sicong Li, Yuhui Sun, Peter F Leadlay, Marcio Vinicius Bertacine Dias
Gentamicins are heavily methylated, clinically valuable pseudotrisaccharide antibiotics produced by Micromonospora echinospora. GenN has been characterised as an S-adenosyl-L-methionine-dependent methyltransferase with low sequence similarity to other enzymes. It is responsible for the 3''-N-methylation of 3''-dehydro-3''-amino-gentamicin A2, an essential modification of ring III in the biosynthetic pathway to the gentamicin C complex. Purified recombinant GenN also efficiently catalyzes 3''-N-methylation of related aminoglycosides kanamycin B and tobramycin, which both contain an additional hydroxymethyl group at the C5'' position in ring III...
September 6, 2017: ACS Chemical Biology
https://www.readbyqxmd.com/read/28876240/crystal-structures-of-the-methyltransferase-and-helicase-from-the-zika-1947-mr766-uganda-strain
#9
Malgorzata Bukrejewska, Urszula Derewenda, Malwina Radwanska, Daniel A Engel, Zygmunt S Derewenda
Two nonstructural proteins encoded by Zika virus strain MR766 RNA, a methyltransferase and a helicase, were crystallized and their structures were solved and refined at 2.10 and 2.01 Å resolution, respectively. The NS5 methyltransferase contains a bound S-adenosyl-L-methionine (SAM) co-substrate. The NS3 helicase is in the apo form. Comparison with published crystal structures of the helicase in the apo, nucleotide-bound and single-stranded RNA (ssRNA)-bound states suggests that binding of ssRNA to the helicase may occur through conformational selection rather than induced fit...
September 1, 2017: Acta Crystallographica. Section D, Structural Biology
https://www.readbyqxmd.com/read/28862845/structural-and-functional-analyses-of-periplasmic-5-methylthioadenosine-s-adenosylhomocysteine-nucleosidase-from-aeromonas-hydrophila
#10
Yongbin Xu, Lulu Wang, Jinli Chen, Jing Zhao, Shengdi Fan, Yuesheng Dong, Nam-Chul Ha, Chunshan Quan
The gram-negative, rod-shaped bacterium Aeromonas hydrophila has two multifunctional 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase (MTAN) enzymes, MtaN-1 and MtaN-2, that differ from those in other bacteria. These proteins are essential for several metabolic pathways, including biological methylation, polyamine biosynthesis, methionine recycling and bacterial quorum sensing. To gain insight into how these two proteins function, we determined four high-resolution crystal structures of MtaN-1 in its apo form and in complex with the substrates S-adenosyl-L-homocysteine (SAH), 5'-methylthioadenosine (MTA), and 5'-deoxyadenosine (5'-DAO)...
September 1, 2017: Biochemistry
https://www.readbyqxmd.com/read/28861701/heat-stress-differentially-modifies-ethylene-biosynthesis-and-signaling-in-pea-floral-and-fruit-tissues
#11
Raghavendra P Savada, Jocelyn A Ozga, Charitha P A Jayasinghege, Kosala D Waduthanthri, Dennis M Reinecke
Ethylene biosynthesis is regulated in reproductive tissues in response to heat stress in a manner to optimize resource allocation to pollinated fruits with developing seeds. High temperatures during reproductive development are particularly detrimental to crop fruit/seed production. Ethylene plays vital roles in plant development and abiotic stress responses; however, little is known about ethylene's role in reproductive tissues during development under heat stress. We assessed ethylene biosynthesis and signaling regulation within the reproductive and associated tissues of pea during the developmental phase that sets the stage for fruit-set and seed development under normal and heat-stress conditions...
August 31, 2017: Plant Molecular Biology
https://www.readbyqxmd.com/read/28859976/structural-and-mechanistic-comparison-of-the-cyclopropane-mycolic-acid-synthases-cmas-protein-family-of-mycobacterium-tuberculosis
#12
Lucas A Defelipe, Federico Osman, Marcelo A Marti, Adrián G Turjanski
Tuberculosis (TB) is a chronic disease caused by the bacillus Mycobacterium tuberculosis(Mtb) and remains a leading cause of mortality worldwide. The bacteria has an external wall which protects it from being killed, and the enzymes involved in the biosynthesis of the cell wall components have been proposed as promising targets for future drug development efforts. Cyclopropane Mycolic Acid Synthases (CMAS) constitute a group of ten homologous enzymes which belong to the mycolic acid biosynthesis pathway. These enzymes have S-adenosyl-l-methionine (SAM) dependent methyltransferase activity with a peculiarity, each one of them has strong substrate selectivity and reaction specificity, being able to produce among other things cyclopropanes or methyl-alcohol groups from the lipid olefin group...
August 30, 2017: Biochemical and Biophysical Research Communications
https://www.readbyqxmd.com/read/28829136/ionic-current-based-mapping-of-short-sequence-motifs-in-single-dna-molecules-using-solid-state-nanopores
#13
Kaikai Chen, Matyas Juhasz, Felix Gularek, Elmar Weinhold, Yu Tian, Ulrich F Keyser, Nicholas A W Bell
Nanopore sensors show great potential for rapid, single-molecule determination of DNA sequence information. Here, we develop an ionic current-based method for determining the positions of short sequence motifs in double-stranded DNA molecules with solid-state nanopores. Using the DNA-methyltransferase M.TaqI and a biotinylated S-adenosyl-l-methionine cofactor analogue we create covalently attached biotin labels at 5'-TCGA-3' sequence motifs. Monovalent streptavidin is then added to bind to the biotinylated sites giving rise to additional current blockade signals when the DNA passes through a conical quartz nanopore...
September 13, 2017: Nano Letters
https://www.readbyqxmd.com/read/28821266/endogenous-hydrogen-sulphide-attenuates-nlrp3-inflammasome-mediated-neuroinflammation-by-suppressing-the-p2x7-receptor-after-intracerebral-haemorrhage-in-rats
#14
Hengli Zhao, Pengyu Pan, Yang Yang, Hongfei Ge, Weixiang Chen, Jie Qu, Jiantao Shi, Gaoyu Cui, Xin Liu, Hua Feng, Yujie Chen
BACKGROUND: Emerging studies have demonstrated the important physiological and pathophysiological roles of hydrogen sulphide (H2S) as a gasotransmitter for NOD-like receptor family pyrin domain-containing 3 (NLRP3) inflammasome-associated neuroinflammation in the central nervous system. However, the effects of H2S on neuroinflammation after intracerebral haemorrhage (ICH), especially on the NLRP3 inflammasome, remain unknown. METHODS: We employed a Sprague-Dawley rat of collagenase-induced ICH in the present study...
August 18, 2017: Journal of Neuroinflammation
https://www.readbyqxmd.com/read/28818801/development-and-validation-of-a-reliable-method-for-thiopurine-methyltransferase-tpmt-enzyme-activity-in-human-whole-blood-by-lc-ms-ms-an-application-for-phenotypic-and-genotypic-correlations
#15
Supaporn Wiwattanakul, Santirhat Prommas, Nuttawut Jenjirattithigarn, Siwalee Santon, Apichaya Puangpetch, Samart Pakakasama, Usanarat Anurathapan, Chonlaphat Sukasem
A liquid chromatography-tandem mass spectrometry (LC-MS/MS) method was developed for the determination of thiopurine methyltransferase (TPMT) activity in human whole blood lysate, based on conversion of 6-mercaptopurine (6-MP) by TPMT to 6-methylmercaptopurine (6-MMP) using S-adenosyl-l-methionine (SAM) as the methyl donor. This method was improved from the previous laborious method for washing of red cell lysate preparation to develop whole blood EDTA lysate. In addition, the TPMT incubation was optimized and the chromatography was performed in a short runtime of 7min on a C18-column by detection via triple quadrupole mass spectrometry...
October 25, 2017: Journal of Pharmaceutical and Biomedical Analysis
https://www.readbyqxmd.com/read/28808922/backbone-resonance-assignments-for-the-set-domain-of-human-methyltransferase-nsd3-in-complex-with-its-cofactor
#16
Yan Li, Hui Qi Ng, Anna Ngo, Shuang Liu, Yih Wan Tan, Perlyn Zekui Kwek, Alvin W Hung, Joma Joy, Jeffrey Hill, Thomas H Keller, CongBao Kang
NSD3 is a histone H3 methyltransferase that plays an important role in chromatin biology. A construct containing the methyltransferase domain encompassing residues Q1049-K1299 of human NSD3 was obtained and biochemical activity was demonstrated using histone as a substrate. Here we report the backbone HN, N, Cα, C', and side chain Cβ assignments of the construct in complex with S-adenosyl-L-methionine (SAM). Based on these assignments, secondary structures of NSD3/SAM complex in solution were determined.
August 14, 2017: Biomolecular NMR Assignments
https://www.readbyqxmd.com/read/28802136/the-role-of-sulfate-in-aerobic-granular-sludge-process-for-emerging-sulfate-laden-wastewater-treatment
#17
Weiqi Xue, Tianwei Hao, Hamish R Mackey, Xiling Li, Richard C Chan, Guanghao Chen
Sulfate-rich wastewaters pose a major threat to mainstream wastewater treatment due to the unpreventable production of sulfide and associated shift in functional bacteria. Aerobic granular sludge could mitigate these challenges in view of its high tolerance and resilience against changes in various environmental conditions. This study aims to confirm the feasibility of aerobic granular sludge in the treatment of sulfate containing wastewater, investigate the impact of sulfate on nutrient removal and granulation, and reveal metabolic relationships in the above processes...
August 4, 2017: Water Research
https://www.readbyqxmd.com/read/28768413/monovalent-cation-activation-of-the-radical-sam-enzyme-pyruvate-formate-lyase-activating-enzyme
#18
Krista A Shisler, Rachel U Hutcheson, Masaki Horitani, Kaitlin S Duschene, Adam V Crain, Amanda S Byer, Eric M Shepard, Ashley Rasmussen, Jian Yang, William E Broderick, Jessica L Vey, Catherine L Drennan, Brian M Hoffman, Joan B Broderick
Pyruvate formate-lyase activating enzyme (PFL-AE) is a radical S-adenosyl-l-methionine (SAM) enzyme that installs a catalytically essential glycyl radical on pyruvate formate-lyase. We show that PFL-AE binds a catalytically essential monovalent cation at its active site, yet another parallel with B12 enzymes, and we characterize this cation site by a combination of structural, biochemical, and spectroscopic approaches. Refinement of the PFL-AE crystal structure reveals Na(+) as the most likely ion present in the solved structures, and pulsed electron nuclear double resonance (ENDOR) demonstrates that the same cation site is occupied by (23)Na in the solution state of the as-isolated enzyme...
August 30, 2017: Journal of the American Chemical Society
https://www.readbyqxmd.com/read/28762403/catalysis-by-solvation-rather-than-the-desolvation-effect-exploring-the-catalytic-efficiency-of-sam-dependent-chlorinase
#19
Edson Araújo, Anderson H Lima, Jerônimo Lameira
Chlorinase SalL halogenate S-adenosyl-l-methionine (SAM) reacts with chloride to generate 5'-chloro-5'-deoxyadenosine and l-methionine through a nucleophilic substitution mechanism. Although it is known that chlorinase enhances the rate of reaction by a factor of 1.2 × 10(17) fold, it is not entirely clear how this is accomplished. The search for the origin of the catalysis of chlorinase and other enzymes has led to a desolvation hypothesis. In the present work, we have used well defined computational simulations in order to evaluate the origin of the catalytic efficiency of chlorinase...
August 16, 2017: Physical Chemistry Chemical Physics: PCCP
https://www.readbyqxmd.com/read/28743037/exogenous-applications-of-polyamines-modulate-drought-responses-in-wheat-through-osmolytes-accumulation-increasing-free-polyamine-levels-and-regulation-of-polyamine-biosynthetic-genes
#20
Heba Talat Ebeed, Nemat Mohamed Hassan, Alshafei Mohammed Aljarani
Polyamines (PAs) can improve drought stress tolerance in plants; however, very limited information is available on the mechanism of action of exogenous application by different methods under drought stress in wheat. The present study investigates the mechanism through which seed priming and foliar spraying with PAs protect wheat plants from drought stress. 10 days old wheat seedlings were exposed to drought stress by withholding water alone or with 100 μM PAs solutions (putrescine, Put; spermine, Spm; and mixture of Put and Spm for 10 h seed-priming or three foliar sprays during withholding water...
July 15, 2017: Plant Physiology and Biochemistry: PPB
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