D5011

5′-Deoxy-5′-(methylthio)adenosine

• Synonym(s): Methylthioadenosine, MTA
• Empirical Formula (Hill Notation): C₁₁H₁₅N₅O₃S
• CAS Number: 2457-80-9
• Molecular Weight: 297.33
• Beilstein: 42420
• MDL number: MFCD00010533
• UNSPSC Code: 41106305
• PubChem Substance ID: 24893915
• NACRES: NA.51

Properties

• 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)

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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves