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D5011

5′-Deoxy-5′-(methylthio)adenosine

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

Synonym(s):

Methylthioadenosine, MTA

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$81.80

100 MG

$245.00

250 MG

$434.00

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$1,260.00

$81.80

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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,

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

SMILES string

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

InChI key

WUUGFSXJNOTRMR-IOSLPCCCSA-N

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

Quality Level

200

Gene Information

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

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1 of 4

This Item
D8668D5782D7400
5′-Deoxy-5′-(methylthio)adenosine

Sigma-Aldrich

D5011

5′-Deoxy-5′-(methylthio)adenosine

2′-Deoxyadenosine monohydrate powder, BioReagent, suitable for cell culture

Sigma-Aldrich

D8668

2′-Deoxyadenosine monohydrate

2′,3′-Dideoxycytidine ≥98% (HPLC)

Sigma-Aldrich

D5782

2′,3′-Dideoxycytidine

2′-Deoxyadenosine monohydrate ≥99%

Sigma-Aldrich

D7400

2′-Deoxyadenosine monohydrate

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

assay

≥98% (HPLC)

assay

≥99% (HPLC)

assay

≥98% (HPLC)

assay

≥99%

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

solubility

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

solubility

H2O: soluble 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

solubility

water: 50 mg/mL, clear, colorless to faintly yellow

solubility

water: 25 mg/mL, clear to slightly hazy, colorless to faintly yellow

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.[1] It has also been used to inhibit histone methylation modification and study its role in hypoxia inducible factor-1 (Hif-1) nuclear transport.[2]

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
0000529004
0000529004
0000493642
0000493641
0000493639

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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)
Ishari Waduwara-Jayabahu et al.
Plant physiology, 158(4), 1728-1744 (2012-02-22)
5'-Methylthioadenosine (MTA) is the common by-product of polyamine (PA), nicotianamine (NA), and ethylene biosynthesis in Arabidopsis (Arabidopsis thaliana). The methylthiol moiety of MTA is salvaged by 5'-methylthioadenosine nucleosidase (MTN) in a reaction producing methylthioribose (MTR) and adenine. The MTN double
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
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