D5011

5′-Deoxy-5′-(methylthio)adenosine

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

• Synonym(s): Methylthioadenosine, MTA
• 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

Properties

• Product Name: 5′-Deoxy-5′-(methylthio)adenosine,
• biological source: synthetic (organic)
• Quality Segment: 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)

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.

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.

Safety Information

• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)