5’-Deoxy-5’-methylthioadenosine

  • CAT Number: R056852
  • CAS Number: 2457-80-9
  • Molecular Formula: C11H15N5O3S
  • Molecular Weight: 297.333
  • Purity: ≥95%
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Methylthioadenosine, also known as MTA and 5/’- Methylthioadenosine, is a naturally occurring sulfur-containing nucleoside present in all mammalian tissues. In vitro experiments showed that MTA treatment inhibited melanoma cell proliferation and viability in a dose dependent manner, where BRAF mutant melanoma cell lines appear to be more sensitive. Importantly, MTA was effective inhibiting in vivo tumor growth. The molecular analysis of tumor samples and in vitro experiments indicated that MTA induces cytostatic rather than pro-apoptotic effects inhibiting the phosphorylation of Akt and S6 ribosomal protein and inducing the down-regulation of cyclin D1. ( BMC Cancer . 2010 Jun 8;10:265.)

Catalog Number R056852
CAS Number 2457-80-9
Molecular Formula

C11H15N5O3S

Purity 95%
Target Nucleoside Antimetabolite/Analogue
Solubility Soluble in DMSO
Storage Store at -20C
IUPAC Name (2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
InChI InChI=1S/C11H15N5O3S/c1-20-2-5-7(17)8(18)11(19-5)16-4-15-6-9(12)13-3-14-10(6)16/h3-5,7-8,11,17-18H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChIKey WUUGFSXJNOTRMR-IOSLPCCCSA-N
SMILES CSCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
Reference

</br>1:Purification and characterization of antioxidant components from the fruiting bodies of Pleurotus abalonus including 9-beta-d-ribofuranosidoadenine, 5/’-deoxy-5/’-(methylthio)adenosine, and a triterpenoid. Zhang YN, Song M, Ng TB, Zhao L, Liu F.Environ Toxicol Pharmacol. 2013 Sep;36(2):689-96. doi: 10.1016/j.etap.2013.06.007. Epub 2013 Jun 28. PMID: 23892470 </br>2:Radical SAM activation of the B12-independent glycerol dehydratase results in formation of 5/’-deoxy-5/’-(methylthio)adenosine and not 5/’-deoxyadenosine. Demick JM, Lanzilotta WN.Biochemistry. 2011 Feb 1;50(4):440-2. doi: 10.1021/bi101255e. Epub 2011 Jan 5. PMID: 21182298 </br>3:Direct and tumor microenvironment mediated influences of 5/’-deoxy-5/’-(methylthio)adenosine on tumor progression of malignant melanoma. Stevens AP, Spangler B, Wallner S, Kreutz M, Dettmer K, Oefner PJ, Bosserhoff AK.J Cell Biochem. 2009 Feb 1;106(2):210-9. doi: 10.1002/jcb.21984. PMID: 19097084 </br>4:Novel trypanocidal analogs of 5/’-(methylthio)-adenosine. Sufrin JR, Spiess AJ, Marasco CJ Jr, Rattendi D, Bacchi CJ.Antimicrob Agents Chemother. 2008 Jan;52(1):211-9. Epub 2007 Oct 22. PMID: 17954686 Free PMC Article</br>5:Antimicrobial and antiviral activity of xylosyl-methylthio-adenosine, a naturally occurring analogue of methylthio-adenosine from Doris verrucosa. Pani A, Marongiu ME, Obino P, Gavagnin M, La Colla P.Experientia. 1991 Dec 1;47(11-12):1228-9. PMID: 1765135 </br>6:Targeting 5/’-deoxy-5/’-(methylthio)adenosine phosphorylase by 5/’-haloalkyl analogues of 5/’-deoxy-5/’-(methylthio)adenosine. Sufrin JR, Spiess AJ, Kramer DL, Libby PR, Miller JT, Bernacki RJ, Lee YH, Borchardt RT, Porter CW.J Med Chem. 1991 Aug;34(8):2600-6. PMID: 1908523 </br>7:Synthesis and antiproliferative effects of novel 5/’-fluorinated analogues of 5/’-deoxy-5/’-(methylthio)adenosine. Sufrin JR, Spiess AJ, Kramer DL, Libby PR, Porter CW.J Med Chem. 1989 May;32(5):997-1001. Erratum in: J Med Chem 1990 Apr;33(4):1270. PMID: 2496231 </br>8:Mutagenic and comutagenic action of 5/’-deoxy-5/’-(methylthio)adenosine. Näslund M, Kláŝterská I, Kolman A, Ehrenberg L.Mutat Res. 1986 Jun;161(1):1-7. PMID: 3517630 </br>9:Analogs of 5/’-deoxy-5/’-(methylthio)adenosine. Montgomery JA, Shortnacy AT, Thomas HJ.J Med Chem. 1974 Nov;17(11):1197-207. No abstract available. PMID: 4412000

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