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D5011

Sigma-Aldrich

5′-Deoxy-5′-(methylthio)adenosine

Synonym(s):

Methylthioadenosine, MTA

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About This Item

Empirical Formula (Hill Notation):
C11H15N5O3S
CAS Number:
2457-80-9
Molecular Weight:
297.33
Beilstein:
42420
MDL number:
MFCD00010533
UNSPSC Code:
41106305
PubChem Substance ID:
24893915
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

human ... ADORA2B(136) , ADORA3(140)
mouse ... Mtap(66902)
rat ... Adora1(29290) , Adora2a(25369)

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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.

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.

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

Certificates of Analysis (COA)

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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)
SET7/9 promotes hepatocellular carcinoma progression through regulation of E2F1
Gu Y, et al.
Oncology Reports, 40(4), 1863-1874 (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
Tobias J Erb et al.
Nature chemical biology, 8(11), 926-932 (2012-10-09)
Functional assignment of uncharacterized proteins is a challenge in the era of large-scale genome sequencing. Here, we combine in extracto NMR, proteomics and transcriptomics with a newly developed (knock-out) metabolomics platform to determine a potential physiological role for a ribulose-1,5-bisphosphate
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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Articles

Histone Modification and Chromatin Remodeling | Epigenetics

Epigenetic modifications are thought to occur through two key interconnected processes—DNA methylation and the covalent modification of histones.

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