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D5011 Sigma-Aldrich

5′-Deoxy-5′-(methylthio)adenosine

Synonym: MTA, Methylthioadenosine

  • CAS Number 2457-80-9

  • Empirical Formula (Hill Notation) C11H15N5O3S

  • Molecular Weight 297.33

  •  Beilstein/REAXYS Number 42420

  •  MDL number MFCD00010533

  •  PubChem Substance ID 24893915

  •  NACRES NA.51

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Properties

Related Categories Bioactive Small Molecules for Epigenetic Research, Biochemicals and Reagents, Epigenetics, Histone Methylation Modulators, Molecular Biology,
Quality Level   200
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)

Description

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
RTECS 
AU7410000
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Epigenetics, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Peer-Reviewed Papers
15

References

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