B2292

O⁶-Benzylguanine

≥98% (TLC), solid, O⁶-alkylguanine DNA alkyltransferase inhiitor

• Empirical Formula (Hill Notation): C₁₂H₁₁N₅O
• CAS Number: 19916-73-5
• Molecular Weight: 241.25
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278259
• NACRES: NA.77
• MDL number: MFCD00269931
• Assay: ≥98% (TLC)
• Form: solid

Properties

• Product Name: O⁶-Benzylguanine, ≥98% (TLC), solid
• Quality Segment: 200
• assay: ≥98% (TLC)
• form: solid
• solubility: methanol: 20 mg/mL
• storage temp.: room temp
• SMILES string: Nc1nc(OCc2ccccc2)c3nc[nH]c3n1
• 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
• Gene Information: human ... MGMT(4255)

Description

Application

O⁶-Benzylguanine has been used:

• as an inhibitor of methylguanine methyltransferase (MGMT) in glioblastoma stem cell
• as a O6-alkylguanine-alkyltransferase (AGT) enzyme inhibitor in embryonic stem cells prior to N-ethyl-N-nitrosourea(ENU) treatment
• as an inhibitor of AGT in growth inhibition assays of HL-60 human promyelocytic leukemia cells

Biochem/physiol Actions

O(6)-benzylguanine is an antineoplastic agent that binds the DNA repair enzyme O(6)-alkylguanine DNA alkyltransferase (AGT), resulting in inhibition of AGT-mediated DNA repair. It is widely used in various DNA repair mechanism studies and potentiates the effects of other chemotherapeutic agents that damage DNA.

O⁶-Benzylguanine (O6BG) inhibits methylguanine methyltransferase (MGMT) by blocking the active site through benzyl group transfer. The use of O6BG with bis-chloroethylnitrosourea (BCNU) or carmustine is effective in treating solid tumors including lymphomas, melanomas and sarcoma.

Safety Information

• pictograms: GHS07
• signalword: Warning
• Storage Class: 11 - Combustible Solids
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Gloves
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral