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D5011

5′-Deoxy-5′-(methylthio)adenosine

Name: 5&#8242;-Deoxy-5&#8242;-(methylthio)adenosine
Brand: SIGMA

≥98% (HPLC), synthetic (organic), powder

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

NACRES:

NA.51

PubChem Substance ID:

24893915

UNSPSC Code:

41106305

MDL number:

MFCD00010533

Beilstein/REAXYS Number:

42420

Assay:

≥98% (HPLC)

Biological source:

synthetic (organic)

Form:

powder

Solubility:

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

Storage temp.:

−20°C

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Product Name

5′-Deoxy-5′-(methylthio)adenosine,

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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Biochemicals

Nucleosides and Nucleotides

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

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000549788

0000529004

0000493642

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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)

Small-molecule inhibitor binding to an N-acyl-homoserine lactone synthase.

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

Characterizing DNA methyltransferases with an ultrasensitive luciferase-linked continuous assay.

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

Metabolomic profile of hepatitis C virus-infected hepatocytes.

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

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Global Trade Item Number

SKU	GTIN
D5011-1G	04061826690574
D5011-100MG	04061833585948
D5011-25MG	04061833585955
D5011-250MG	04061833047941

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