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1-Methyladenosine Sale

(Synonyms: 1-甲基腺苷) 目录号 : GC33463

1-甲基腺苷是一种在1 位带有甲基取代基的甲基腺苷。它具有作为人体代谢物的作用,在功能上与腺苷有关

1-Methyladenosine Chemical Structure

Cas No.:15763-06-1

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10mM (in 1mL DMSO)
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50mg
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产品描述

1-Methyladenosine is a modified nucleoside generated by the processing of tRNA by methyltransferases.1,2,3 The urinary excretion of 1-methyladenosine is elevated in several forms of cancer, supporting its use as a biomarker in early detection.4,5,6 It can also be monitored in serum.7 Urinary levels of 1-methyladenosine also increase during active rheumatoid arthritis.8

1.Munns, T.W., and Sims, H.F.Methylation and processing of transfer ribonucleic acid in mammalian and bacterial cellsJ. Biol. Chem.250(6)2143-2149(1975) 2.Vold, B.Modified nucleosides of Bacillus subtilis transfer ribonucleic acidsJ. Bacteriol.127(1)258-267(1976) 3.Chujo, T., and Suzuki, T.Trmt61B is a methyltransferase responsible for 1-methyladenosine at position 58 of human mitochondrial tRNAsRNA18(12)2269-2276(2012) 4.Reynaud, C., Bruno, C., Boullanger, P., et al.Monitoring of urinary excretion of modified nucleosides in cancer patients using a set of six monoclonal antibodiesCancer Lett.255-262(1991) 5.Seidel, A., Brunner, S., Seidel, P., et al.Modified nucleosides: An accurate tumour marker for clinical diagnosis of cancer, early detection and therapy controlBr. J. Cancer.94(11)1726-1733(2006) 6.Hsu, W.Y., Chen, C.J., Huang, Y.C., et al.Urinary nucleosides as biomarkers of breast, colon, lung, and gastric cancer in TaiwanesePLoS One8(12)1-8(2013) 7.Chen, F., Xue, J., Zhou, L., et al.Identification of serum biomarkers of hepatocarcinoma through liquid chromatography/mass spectrometry-based metabonomic methodAnal. Bioanal. Chem.401(6)1899-1904(2011) 8.Tebib, J.G., Reynaud, C., Cedoz, J.P., et al.Relationship between urinary excretion of modified nucleosides and rheumatoid arthritis processBr. J. Rheumatol.36(9)990-995(1997)

Chemical Properties

Cas No. 15763-06-1 SDF
别名 1-甲基腺苷
Canonical SMILES OC[C@@H]1[C@H]([C@H]([C@H](N2C=NC3=C2N=CN(C)C3=N)O1)O)O
分子式 C11H15N5O4 分子量 281.27
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1 mM 3.5553 mL 17.7765 mL 35.553 mL
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Research Update

The epitranscriptome beyond m6A

Nat Rev Genet 2021 Feb;22(2):119-131.PMID:33188361DOI:10.1038/s41576-020-00295-8.

Following its transcription, RNA can be modified by >170 chemically distinct types of modifications - the epitranscriptome. In recent years, there have been substantial efforts to uncover and characterize the modifications present on mRNA, motivated by the potential of such modifications to regulate mRNA fate and by discoveries and advances in our understanding of N 6-methyladenosine (m6A). Here, we review our knowledge regarding the detection, distribution, abundance, biogenesis, functions and possible mechanisms of action of six of these modifications - pseudouridine (Ψ), 5-methylcytidine (m5C), N 1-Methyladenosine (m1A), N 4-acetylcytidine (ac4C), ribose methylations (Nm) and N 7-methylguanosine (m7G). We discuss the technical and analytical aspects that have led to inconsistent conclusions and controversies regarding the abundance and distribution of some of these modifications. We further highlight shared commonalities and important ways in which these modifications differ with respect to m6A, based on which we speculate on their origin and their ability to acquire functions over evolutionary timescales.

Metabolism of 1-Methyladenosine

Biochem Med Metab Biol 1987 Aug;38(1):69-73.PMID:3663399DOI:10.1016/0885-4505(87)90063-6.

1-[methyl-8-14C] Adenosine was synthesized and its metabolic fate was determined in intact rat. It was found that approximately 57% of 1-[methyl-8-14C] adenosine administered iv was excreted unchanged in the urine and 33% of the excreted radioactivity in the urine was associated with the major metabolite 1-methyl-hypoxanthine and about 4.5% was associated with 1-methylinosine. Very little adenosine or N6-methyladenosine was formed. It is concluded that 1-Methyladenosine is initially deaminated by adenosine deaminase to 1-methylinosine which is then cleaved by nucleoside phosphorylase to 1-methylhypoxanthine.

m1A Post-Transcriptional Modification in tRNAs

Biomolecules 2017 Feb 21;7(1):20.PMID:28230814DOI:10.3390/biom7010020.

To date, about 90 post-transcriptional modifications have been reported in tRNA expanding their chemical and functional diversity. Methylation is the most frequent post-transcriptional tRNA modification that can occur on almost all nitrogen sites of the nucleobases, on the C5 atom of pyrimidines, on the C2 and C8 atoms of adenosine and, additionally, on the oxygen of the ribose 2'-OH. The methylation on the N1 atom of adenosine to form 1-Methyladenosine (m1A) has been identified at nucleotide position 9, 14, 22, 57, and 58 in different tRNAs. In some cases, these modifications have been shown to increase tRNA structural stability and induce correct tRNA folding. This review provides an overview of the currently known m1A modifications, the different m1A modification sites, the biological role of each modification, and the enzyme responsible for each methylation in different species. The review further describes, in detail, two enzyme families responsible for formation of m1A at nucleotide position 9 and 58 in tRNA with a focus on the tRNA binding, m1A mechanism, protein domain organisation and overall structures.

N 1-Methyladenosine (m1A) RNA modification: the key to ribosome control

J Biochem 2020 Jun 1;167(6):535-539.PMID:32129871DOI:10.1093/jb/mvaa026.

RNA displays diverse functions in living cells. The presence of various chemical modifications of RNA mediated by enzymes is one of the factors that impart such functional diversity to RNA. Among more than 100 types of RNA modification, N1-methyladenosine (m1A) is found mainly in tRNA and rRNA of many living organisms and is known to be deeply implicated in the topology or function of the two classes of RNA. In this commentary article, we would like to deal with the functional significance of m1A in RNA, and also to describe one methyltransferase installing m1A in a large subunit rRNA, whose orthologue in Caenorhabditis elegans was discovered recently and was reported in this journal.

Transfer RNA demethylase ALKBH3 promotes cancer progression via induction of tRNA-derived small RNAs

Nucleic Acids Res 2019 Mar 18;47(5):2533-2545.PMID:30541109DOI:10.1093/nar/gky1250.

Transfer RNA is heavily modified and plays a central role in protein synthesis and cellular functions. Here we demonstrate that ALKBH3 is a 1-Methyladenosine (m1A) and 3-methylcytidine (m3C) demethylase of tRNA. ALKBH3 can promote cancer cell proliferation, migration and invasion. In vivo study confirms the regulation effects of ALKBH3 on growth of tumor xenograft. The m1A demethylated tRNA is more sensitive to angiogenin (ANG) cleavage, followed by generating tRNA-derived small RNAs (tDRs) around the anticodon regions. tDRs are conserved among species, which strengthen the ribosome assembly and prevent apoptosis triggered by cytochrome c (Cyt c). Our discovery opens a potential and novel paradigm of tRNA demethylase, which regulates biological functions via generation of tDRs.