A pseudosubstrate and inactivator of AGT
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O6-Benzylguanine

Item No. 16332

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMSO: 30 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 5 mg/ml
λmax
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 mg

    $36

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    50 mg

    $62

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    250 mg

    $253

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    1 g

    $769

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    Cayman Chemical
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    Product Description

    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.1,2 O6-Benzylguanine is effective in vivo as well as in vitro.3 Inactivation of AGT increases the chemotherapeutic effectiveness of chloroethylating and methylating agents.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Goodtzova, K., Crone, T.M., and Pegg, A.E. Activation of human O6-alkylguanine-DNA alkyltransferase by DNA. Biochemistry 33(28), 8385-8390 (1994).

    2. Elder, R.H., Margison, G.P., and Rafferty, J.A. Differential inactivation of mammalian and Escherichia coli O6-alkylguanine-DNA alkyltransferases by O6-benzylguanine. Biochem. J. 298, 231-235 (1994).

    3. Kreklau, E.L., Kurpad, C., Williams, D.A., et al. Prolonged inhibition of O6-methylguanine DNA methyltransferase in human tumor cells by O6-benzylguanine in vitro and in vivo. J. Pharmacol. Exp. Ther. 291(3), 1269-1275 (1999).

    4. Dolan, M.E., and Pegg, A.E. O6-Benzylguanine and its role in chemotherapy. Clin. Cancer Res. 3, 837-847 (1997).