5'-Deoxy-5'-methylthioadenosine-d3

5'-Deoxy-5'-methylthioadenosine-d₃ (MTA-d₃) is intended for use as an internal standard for the quantification of MTA by GC- or LC-MS. MTA is an intermediate in the generation of adenine and methionine that is produced by the decarboxylation of S-adenosylmethionine.¹ This nucleoside is a potent agonist of adenosine receptors (K_is = 0.15, 1.13, 13.9, and 0.68 μM for A₁, A_2A, A_2B, and A₃, respectively).² At higher concentrations, MTA inhibits several enzymes, including protein carboxylmethyltransferase (K_i = 41 μM), S-adenosylhomocysteine hydrolase, SET methyltransferases, and spermidine and spermine synthases.^3,1,4,5

1.Huang, S.Histone methyltransferases, diet nutrients and tumour suppressorsNat. Rev. Cancer2(6)469-476(2002) 2.Kehraus, S., Gorzalka, S., Hallmen, C., et al.Novel amino acid derived natural products from the ascidian Atriolum robustum: Identification and pharmacological characterization of a unique adenosine derivativeJ. Med. Chem.47(9)2243-2255(2004) 3.Oliva, A., Galletti, P., Zappia, V., et al.Studies on substrate specificity of S-adenosylmethionine: Protein-carboxyl methyltransferase from calf brainEur. J. Biochem.104(2)595-602(1980) 4.Cole, P.A.Chemical probes for histone-modifying enzymesNat. Chem. Biol.4(10)590-597(2008) 5.Lee, S.H., and Cho, Y.D.Induction of apoptosis in leukemia U937 cells by 5'-deoxy-5'-methylthioadenosine, a potent inhibitor of protein carboxylmethyltransferaseExp. Cell Res.240(2)282-292(1998)