|(2R,3R,4S,5S)-2-(6-氨基-9H-嘌呤-9-基)-5-(甲硫基)甲基)四氢呋喃-3,4-二醇|CsnPharm

CAS No.: 2457-80-9

(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol Catalog No. CSN25521

Synonyms: 5'-(Methylthio)-5'-deoxyadenosine;5'-Deoxy-5'-(methylthio)adenosine;5'-S-Methyl-5'-thioadenosine

5'-Methylthioadenosine is produced from S-adenosylmethionine and behaves as a powful inhibitory product and has been used as a protein methylation inhibitor to reduce E2F transcription factor 1 (E2F1) protein abundance in hepatocellular carcinoma (HCC) cells.

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技术信息

生物活性

描述5'-Methylthioadenosine (MTA) is a nucleoside generated from S-adenosylmethionine (SAM) during polyamine synthesis. Pretreatment with MTA (96 μmol/kg, intraperitoneal) significantly improved liver function, attenuated hepatic ischemia-reperfusion injury (IRI) by downregulating TNF-α level and suppressing inflammatory reaction after liver transplantation. Moreover, MTA also inhibited the IκBα degradation, NF-κB transcriptional activity, and the activation of MAPK signal. MTA protected against hepatic IRI by suppressing inflammatory reaction following liver transplantation^[1]. MTA suppresses tumors by inhibiting tumor cell proliferation, invasion, and the induction of apoptosis while controlling the inflammatory micro-environments of tumor tissue^[2]. Excess MTA will protect normal MTAP+ cells from purine analogue toxicity because MTAP catalyzes the conversion of MTA to adenine, which then inhibits the conversion of purine base analogues into nucleotides. MTA protected against both 6TG and 2FA toxicity in an MTAP-dependent manner, shifting the IC50 concentration by one to three orders of magnitude^[3]. MTA reduced the neuronal cell death in pilocarpine-induced status epilepticus and the size of the lesion in global but not focal ischemic brain damage, it was ineffective in preserving dopaminergic neurons of the substantia nigra in the 1-methyl-4-phenyl-1,2,3,6-tetrahydro-pyridine (MPTP)-mice model. MTA may potentially offer therapeutic neuroprotection^[4].
参考文献

[1] Tang Y, Zhang W, Zhang Y, Wang W, Yao F, Yan J, Wan C. 5'-Methylthioadenosine attenuates ischemia reperfusion injury after liver transplantation in rats. Inflammation. 2014 Oct;37(5):1366-73
[2] Li Y, Wang Y, Wu P. 5'-Methylthioadenosine and Cancer: old molecules, new understanding. J Cancer. 2019 Jan 29;10(4):927-936
[3] Tang B, Lee HO, An SS, Cai KQ, Kruger WD. Specific Targeting of MTAP-Deleted Tumors with a Combination of 2'-Fluoroadenine and 5'-Methylthioadenosine. Cancer Res. 2018 Aug 1;78(15):4386-4395
[4] Moreno B, Lopez I, Fernández-Díez B, Gottlieb M, Matute C, Sánchez-Gómez MV, Domercq M, Giralt A, Alberch J, Collon KW, Zhang H, Parent JM, Teixido M, Giralt E, Ceña V, Posadas I, Martínez-Pinilla E, Villoslada P, Franco R. Differential neuroprotective effects of 5'-deoxy-5'-methylthioadenosine. PLoS One. 2014 Mar 5;9(3):e90671

实验方案

计算器摩尔计算器总药量计算器工作液计算器
储存液制备
- 1 mg
- 5 mg
- 10 mg
- 1 mM
- 3.3632 mL
- 16.8161 mL
- 33.6323 mL
- 5 mM
- 0.6726 mL
- 3.3632 mL
- 6.7265 mL
- 10 mM
- 0.3363 mL
- 1.6816 mL
- 3.3632 mL

技术信息

CAS号

2457-80-9

储存条件

粉末: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

液体: -20°C:3-6 月 -80°C:12月

分子式

C11H15N5O3S

运输

蓝冰

分子量

297.33

别名

5'-(Methylthio)-5'-deoxyadenosine;5'-Deoxy-5'-(methylthio)adenosine;5'-S-Methyl-5'-thioadenosine;MTA;NSC 335422;Vitamin L2;Methylthioadenosine;5Deoxy5(methylthio)adenosine;甲硫腺苷

溶解度

DMSO	50.0 mg/mL (168.2 mM) warming
Water	1.0 mg/mL (3.4 mM) warming
DMF	2.5 mg/mL (8.4 mM) warming

动物实验配方

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(2R,3R,4S,5S)-2-(6-Amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol Catalog No. CSN25521

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