5'-S-Methyl-5'-thioadenosine

Alkaloids

NP0501

2457-80-9

5'-S-Methyl-5'-thioadenosine

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.

Methylthioadenosine; MTA; 58242; -Deoxy-58242; -(methylthio)adenosine.

(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol

297.33

C11H15N5O3S

CSCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O

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

WUUGFSXJNOTRMR-IOSLPCCCSA-N

642.7°C at 760 mmHg

210-213°C (dec.)

98%

1.85 g/cm3

white solid powder

biological transmethylations.

Store at -20°C (under dark)

Yellow

Oil