5'-S-Methyl-5'-thioadenosine

For Research Use Only.
Category
Alkaloids
Cat.No.
NP0501
CAS
2457-80-9
Product Name
5'-S-Methyl-5'-thioadenosine
Structure

Product Details

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.
Synonyms
Methylthioadenosine; MTA; 58242; -Deoxy-58242; -(methylthio)adenosine.
IUPAC Name
(2R,3R,4S,5S)-2-(6-aminopurin-9-yl)-5-(methylsulfanylmethyl)oxolane-3,4-diol
Molecular Weight
297.33
Molecular Formula
C11H15N5O3S
Canonical SMILES
CSCC1C(C(C(O1)N2C=NC3=C2N=CN=C3N)O)O
InChI
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
InChIKey
WUUGFSXJNOTRMR-IOSLPCCCSA-N
Boiling Point
642.7°C at 760 mmHg
Melting Point
210-213°C (dec.)
Purity
98%
Density
1.85 g/cm3
Appearance
white solid powder
Application
biological transmethylations.
Storage
Store at -20°C (under dark)
Color
Yellow
Form
Oil
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