260585

5′-Deoxy-5′-methylthioadenosine

A cell-permeable, reversible, and ATP-competitive naturally-occurring co-product of polyamine biosynthesis that acts as an endogenous substrate of methylthioadenosine phosphorylase (MTAP).

• Synonym(s): 5′-Deoxy-5′-methylthioadenosine, MTA, MeSAdo
• Empirical Formula (Hill Notation): C₁₁H₁₅N₅O₃S
• CAS Number: 2457-80-9
• Molecular Weight: 297.33
• UNSPSC Code: 12352208

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze
• color: white
• solubility: DMF: 25 mg/mL; DMSO: soluble
• shipped in: ambient
• storage temp.: −20°C
• 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)
• InChI key: WUUGFSXJNOTRMR-UHFFFAOYSA-N

Description

General description

A cell-permeable, reversible, and ATP-competitive naturally-occurring co-product of polyamine biosynthesis that acts as an endogenous substrate of methylthioadenosine phosphorylase (MTAP). Potently inhibits the protein carboxymethyltransferase and induces apoptosis in leukemia U937 cells. Also inhibits FGF-2 receptor tyrosine kinase activity as well as the proliferation of human astrocytes and glioma cells.

A naturally occurring co-product of polyamine biosynthesis that acts as an endogenous substrate of methylthioadenosine phosphorylase (MTAP). A cell-permeable, reversible, and ATP-competitive inhibitor of protein carboxymethyltransferase and induces apoptosis in leukemia U937 cells. Also acts as an inhibitor of NGF-induced tyrosine phosphorylation in PC12 cells and blocks FGF-2 receptor tyrosine kinase in astrocytes and glioma cells.

Biochem/physiol Actions

Primary Target
protein carboxymethyltranferase

Secondary Target
FGF-2receptor tyrosine kinase activity

Packaging

Packaged under inert gas

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze at -20°C. Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Lee, S.H., and Cho, Y.D. 1998. Exp. Cell Res.240, 282.
Smalheiser, N.R. 1998. Brain Res. Dev. Brain Res.51, 53.
Joy, A., et al. 1997. Oncogene14, 171.
Riscoe, M.K., et al. 1984. Biochem. Pharmacol.33, 3639.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable