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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/REAXYS Number:
42420
MDL number:
MFCD00010533
UNSPSC Code:
41106305
PubChem Substance ID:
24893915
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
View All Related Papers

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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