Methylthioadenosine
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MedKoo CAT#: 406435

CAS#: 2457-80-9

Description: 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.)

Chemical Structure

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Methylthioadenosine
CAS# 2457-80-9
Instruction

Theoretical Analysis

MedKoo Cat#: 406435
Name: Methylthioadenosine
CAS#: 2457-80-9
Chemical Formula: C11H15N5O3S
Exact Mass: 297.09
Molecular Weight: 297.334
Elemental Analysis: C, 44.43; H, 5.08; N, 23.55; O, 16.14; S, 10.78

Price and Availability

Size Price Availability Quantity
25mg USD 275 Ready to ship
50mg USD 450 2 Weeks
100mg USD 750 2 Weeks
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Synonym: Methylthioadenosine; MTA; 5Deoxy5(methylthio)adenosine; 5'-Deoxy-5'-(methylthio)adenosine

IUPAC/Chemical Name: (2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-((methylthio)methyl)tetrahydrofuran-3,4-diol

InChi Key: WUUGFSXJNOTRMR-IOSLPCCCSA-N

InChi Code: 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

SMILES Code: O[C@H]1[C@H](N2C=NC3=C(N)N=CN=C23)O[C@H](CSC)[C@H]1O

Appearance: Solid powder

Purity: >97% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 297.33 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bertino JR, Waud WR, Parker WB, Lubin M. Targeting tumors that lack methylthioadenosine phosphorylase (MTAP) activity: current strategies. Cancer Biol Ther. 2011 Apr 1;11(7):627-32. Epub 2011 Apr 1. Review. PubMed PMID: 21301207; PubMed Central PMCID: PMC3084968.

2: Parveen N, Cornell KA. Methylthioadenosine/S-adenosylhomocysteine nucleosidase, a critical enzyme for bacterial metabolism. Mol Microbiol. 2011 Jan;79(1):7-20. doi: 10.1111/j.1365-2958.2010.07455.x. Epub 2010 Nov 18. Review. PubMed PMID: 21166890; PubMed Central PMCID: PMC3057356.

3: Albers E. Metabolic characteristics and importance of the universal methionine salvage pathway recycling methionine from 5'-methylthioadenosine. IUBMB Life. 2009 Dec;61(12):1132-42. doi: 10.1002/iub.278. Review. PubMed PMID: 19946895.

4: Avila MA, García-Trevijano ER, Lu SC, Corrales FJ, Mato JM. Methylthioadenosine. Int J Biochem Cell Biol. 2004 Nov;36(11):2125-30. Review. PubMed PMID: 15313459.

5: Della Ragione F, Oliva A, Palumbo R, Russo GL, Zappia V. Enzyme deficiency and tumor suppressor genes: absence of 5'-deoxy-5'-methylthioadenosine phosphorylase in human tumors. Adv Exp Med Biol. 1993;348:31-43. Review. PubMed PMID: 8172020.

6: Della Ragione F, Oliva A, Fioretti M, Russo GL, Palumbo R, Zappia V. Physico-chemical and immunological properties of bovine liver 5'-deoxy-5'-methylthioadenosine phosphorylase. Adv Exp Med Biol. 1988;250:187-97. Review. PubMed PMID: 3151226.

7: Carson DA, Nobori T, Kajander EO, Carrera CJ, Kubota M, Yamanaka H. Methylthioadenosine (MeSAdo) phosphorylase deficiency in malignancy. Adv Exp Med Biol. 1988;250:179-85. Review. PubMed PMID: 3151225.

8: Zappia V, Della Ragione F, Pontoni G, Gragnaniello V, Cartenì-Farina M. Human 5'-deoxy-5'-methylthioadenosine phosphorylase: kinetic studies and catalytic mechanism. Adv Exp Med Biol. 1988;250:165-77. Review. PubMed PMID: 3151224.

9: Schlenk F. Methylthioadenosine. Adv Enzymol Relat Areas Mol Biol. 1983;54:195-265. Review. PubMed PMID: 6405586.

10: Williams-Ashman HG, Seidenfeld J, Galletti P. Trends in the biochemical pharmacology of 5'-deoxy-5'-methylthioadenosine. Biochem Pharmacol. 1982 Feb 1;31(3):277-88. Review. PubMed PMID: 6803807.