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1-Methylinosine Sale

(Synonyms: 1-甲基肌苷; N1-Methylinosine) 目录号 : GC65038

1-亚甲基肌苷是在次黄嘌呤环上的位置 1带有甲基取代基的肌苷。它具有作为代谢物的作用。它在功能上与肌苷有关

1-Methylinosine Chemical Structure

Cas No.:2140-73-0

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10mM (in 1mL DMSO)
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10mg
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50mg
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产品描述

1-Methylinosine is a methylated purine nucleoside formed during the degradation of tRNA.1 Urinary levels of 1-methylinosine are increased in patients with acute myelomonocytic leukemia or large cell lung carcinoma. Urinary levels are also increased in patients with breast cancer and are associated with a reduced five-year survival rate.2

1.Mitchell, E.P., Evans, L., Schultz, P., et al.Modified nucleosides in human serumJ. Chromatogr.581(1)31-40(1992) 2.Sasco, A.J., Rey, F.A., Reynaud, C., et al.Breast cancer prognostic significance of some modified urinary nucleosidesCancer Lett.108(2)157-162(1996)

Chemical Properties

Cas No. 2140-73-0 SDF Download SDF
别名 1-甲基肌苷; N1-Methylinosine
分子式 C11H14N4O5 分子量 282.25
溶解度 DMSO : 20.83 mg/mL (73.80 mM; Need ultrasonic) 储存条件 Store at -20°C
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1 mM 3.543 mL 17.7148 mL 35.4296 mL
5 mM 0.7086 mL 3.543 mL 7.0859 mL
10 mM 0.3543 mL 1.7715 mL 3.543 mL
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Research Update

AtTrm5a catalyses 1-methylguanosine and 1-Methylinosine formation on tRNAs and is important for vegetative and reproductive growth in Arabidopsis thaliana

Nucleic Acids Res 2019 Jan 25;47(2):883-898.PMID:30508117DOI:10.1093/nar/gky1205.

Modified nucleosides on tRNA are critical for decoding processes and protein translation. tRNAs can be modified through 1-methylguanosine (m1G) on position 37; a function mediated by Trm5 homologs. We show that AtTRM5a (At3g56120) is a Trm5 ortholog in Arabidopsis thaliana. AtTrm5a is localized to the nucleus and its function for m1G and m1I methylation was confirmed by mutant analysis, yeast complementation, m1G nucleoside level on single tRNA, and tRNA in vitro methylation. Arabidopsis attrm5a mutants were dwarfed and had short filaments, which led to reduced seed setting. Proteomics data indicated differences in the abundance of proteins involved in photosynthesis, ribosome biogenesis, oxidative phosphorylation and calcium signalling. Levels of phytohormone auxin and jasmonate were reduced in attrm5a mutant, as well as expression levels of genes involved in flowering, shoot apex cell fate determination, and hormone synthesis and signalling. Taken together, loss-of-function of AtTrm5a impaired m1G and m1I methylation and led to aberrant protein translation, disturbed hormone homeostasis and developmental defects in Arabidopsis plants.

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.

A novel enzymatic pathway leading to 1-Methylinosine modification in Haloferax volcanii tRNA

Nucleic Acids Res 1995 Nov 11;23(21):4312-9.PMID:7501451DOI:10.1093/nar/23.21.4312.

Transfer RNAs of the extreme halophile Haloferax volcanii contain several modified nucleosides, among them 1-methylpseudouridine (m1 psi), pseudouridine (psi), 2'-0-methylcytosine (Cm) and 1-Methylinosine (m1l), present in positions 54, 55, 56 and 57 of the psi-loop, respectively. At the same positions in tRNAs from eubacteria and eukaryotes, ribothymidine (T-54), pseudouridine (psi-55), non-modified cytosine (C-56) and non-modified adenosine or guanosine (A-57 or G-57) are found in the so-called T psi-loop. Using as substrate a T7 transcript of Haloferax volcanii tRNA(Ile) devoid of modified nucleosides, the enzymatic activities of several tRNA modification enzymes, including those for m1 psi-54, psi-55, Cm-56 and m1l-57, were detected in cell extracts of H.volcanii. Here, we demonstrate that modification of A-57 into m1l-57 in H.volcanii tRNA(Ile) occurs via a two-step enzymatic process. The first step corresponds to the formation of m1A-57 catalyzed by a S-adenosylmethionine-dependent tRNA methyltransferase, followed by the deamination of the 6-amino group of the adenine moiety by a 1-methyladenosine-57 deaminase. This enzymatic pathway differs from that leading to the formation of m1l-37 in the anticodon loop of eukaryotic tRNA(Ala). In the latter case, inosine-37 formation preceeds the S-adenosylmethionine-dependent methylation of l-37 into m1l-37. Thus, enzymatic strategies for catalyzing the formation of 1-Methylinosine in tRNAs differ in organisms from distinct evolutionary kingdoms.

Archaebacterial tRNA contains 1-Methylinosine at residue 57 in T psi C-loop

Nucleic Acids Symp Ser 1982;(11):209-13.PMID:7183961doi

1-Methylinosine was isolated from unfractionated tRNAs of Sulfolobus acidocaldarius and Halobacterium volcani. The structure of 1-Methylinosine was characterized by ultraviolet absorption and mass spectral analysis. 1-Methylinosine found in these archaebacterial tRNAs was located at residue 57 in T psi C-loop, indicating that the presence of 1-Methylinosine is characteristic of archaebacteria.

Biological markers in breast carcinoma--clinical correlations with pseudouridine, N2,N2-dimethylguanosine, and 1-Methylinosine

J Surg Oncol 1980;14(3):267-73.PMID:7392649DOI:10.1002/jso.2930140313.

Urinary levels of the minor nucleosides, pseudouridine (psi),N2, N2-dimethylguanosine (m22G), and 1-Methylinosine (m1I), were investigated in patients with breast carcinoma. Elevated levels of psi were observed in 27/131 (20.6%) patients with metastatic disease, 1/14 (7.1%) preoperative patients, and 1/28 (3.6%) postoperative N+ patients. Elevated levels of m22G and M1I were observed, respectively, in 46/131 (35.1%) and 274131 (20.6%) patients with metastatic disease, 3/14 (21.4%) and 3/14 preoperative patients, and 6/28 (21.4%) and 2/28 (7.1%) postoperative N+ patients. There was no correlation between nucleoside levels and involvement of specific organ sites with metastatic disease, nor with chemotherapy response rate or time to treatment failure. During the treatment of metastatic disease there was a tendency for elevated pretherapy psi levels to decrease with attainment of a response and, if the levels subsequently rose to be associated with treatment failure. However, increasing levels of m22G and 71I occurred with both response and disease progression. These results suggest that routine measurement of the level of the urinary nucleosides would be of limited value for following the disease course in patients with breast cancer.