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
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
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.
| 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 |
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, GarcÃa-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.
