Merck
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D5011

Sigma-Aldrich

5′-Deoxy-5′-(methylthio)adenosine

Synonym(s):
MTA, Methylthioadenosine
Empirical Formula (Hill Notation):
C11H15N5O3S
CAS Number:
Molecular Weight:
297.33
Beilstein:
42420
MDL number:
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

assay

≥98% (HPLC)

form

powder

solubility

DMF: 50 mg/mL, clear to very slightly hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

CSC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n2cnc3c(N)ncnc23

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

InChI key

WUUGFSXJNOTRMR-IOSLPCCCSA-N

Gene Information

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Application

5′-Deoxy-5′-(methylthio)adenosine has been used as a protein methylation inhibitor to reduce E2F transcription factor 1 (E2F1) protein abundance in hepatocellular carcinoma (HCC) cells. It has also been used to inhibit histone methylation modification and study its role in hypoxia inducible factor-1 (Hif-1) nuclear transport.

Packaging

1 g in poly bottle
25, 100, 250 mg in poly bottle

Biochem/physiol Actions

5′-Deoxy-5′-(methylthio)adenosine (Methylthioadenosine) may be used as a substrate to study the specificity and kinetics of 5′-methylthioadenosinephosphorylase (MTAP) (EC2.4.2.28), a tumor suppressor gene expressed enzyme that supports the S-adenosylmethionine (AdoMet) and methionine salvage pathways.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. D5011.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

SET7/9 promotes hepatocellular carcinoma progression through regulation of E2F1
Gu Y, et al.
Oncology Reports, 40(4), 1863-1874 (2018)
Histone methylation regulates Hif-1 signaling cascade in activation of hepatic stellate cells
Hong F, et al.
FEBS Open Bio, 8(3), 406-415 (2018)
Jiwoung Chung et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(29), 12089-12094 (2011-07-07)
Quorum sensing (QS) controls certain behaviors of bacteria in response to population density. In gram-negative bacteria, QS is often mediated by N-acyl-L-homoserine lactones (acyl-HSLs). Because QS influences the virulence of many pathogenic bacteria, synthetic inhibitors of acyl-HSL synthases might be
Barbara Roe et al.
PloS one, 6(8), e23641-e23641 (2011-08-20)
Hepatitis C virus (HCV) is capable of disrupting different facets of lipid metabolism and lipids have been shown to play a crucial role in the viral life cycle. The aim of this study was to examine the effect HCV infection
Ivan Hemeon et al.
Analytical chemistry, 83(12), 4996-5004 (2011-05-07)
DNA (cytosine-5)-methyltransferases (DNMTs) catalyze the transfer of a methyl group from S-adenosyl-L-methionine (AdoMet) to the 5-position of cytosine residues and thereby silence transcription of regulated genes. DNMTs are important epigenetic targets. However, isolated DNMTs are weak catalysts and are difficult

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