O6-Benzylguanine

O6-Alkylguanine-DNA alkyltransferase (AGT, also known as methylguanine DNA methyltransferase, or MGMT) is a DNA repair protein that directly removes alkyl groups located on the O6-position of guanine from DNA, restoring DNA integrity in a single step. In the process, AGT is alkylated and irreversibly inactivated. O6-Benzylguanine is a guanine analog with antineoplastic activity. It serves as a pseudosubstrate for AGT, transferring a benzyl moiety to the active site cysteine of the enzyme. This leads to irreversible inactivation, with 40% reduction in alkyltransferase activity of recombinant human AGT achieved at 0.06 µM. O6-Benzylguanine is effective in vivo as well as in vitro. Inactivation of AGT increases the chemotherapeutic effectiveness of chloroethylating and methylating agents.Formal Name: 6-(phenylmethoxy)-9H-purin-2-amine. CAS Number: 19916-73-5. Synonyms: NSC 637037. Molecular Formula: C12H11N5O. Formula Weight: 241.2. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 30 mg/ml, DMSO: 30 mg/ml, DMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml, Ethanol: 5 mg/ml. lambdamax: 242, 284 nm. SMILES: NC1=NC(OCC2=CC=CC=C2)=C3C(NC=N3)=N1. InChi Code: InChI=1S/C12H11N5O/c13-12-16-10-9(14-7-15-10)11(17-12)18-6-8-4-2-1-3-5-8/h1-5,7H,6H2,(H3,13,14,15,16,17). InChi Key: KRWMERLEINMZFT-UHFFFAOYSA-N.