WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H208169
CAS#: 19916-73-5
Description: O6-Benzylguanine provides a means to effectively inactivate the AGT protein and increase the chemotherapeutic effectiveness of chloroethylating and methylating agents in vitro and in human tumor xenograft models. Altered AGT proteins resistant to O6-benzylguanine generated from point mutations in the mammalian alkyltransferase gene have been expressed in animal models using retroviral transduction techniques. It is anticipated that the successful application of this approach in humans may provide a means to increase the therapeutic index of O6-benzylguanine and 1, 3-bis(2-chloroethyl)-1-nitrosourea
Hodoodo Cat#: H208169
Name: O6-Benzylguanine
CAS#: 19916-73-5
Chemical Formula: C12H11N5O
Exact Mass: 241.10
Molecular Weight: 241.250
Elemental Analysis: C, 59.74; H, 4.60; N, 29.03; O, 6.63
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Synonym: O6-Benzylguanine, O6-Benzylguanine
IUPAC/Chemical Name: O6BG; BnG; 6-O-Benzylguanine; 6-Phenylmethoxy-7H-purin-2-amine
InChi Key: KRWMERLEINMZFT-UHFFFAOYSA-N
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)
SMILES Code: NC1=NC(N=CN2)=C2C(OCC3=CC=CC=C3)=N1
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: To be determined
Shelf Life: >2 years if stored properly
Drug Formulation: To be determined
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
More Info:
| Biological target: | |
| In vitro activity: | |
| In vivo activity: |
The following data is based on the product molecular weight 241.25 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
| Formulation protocol: | |
| In vitro protocol: | |
| In vivo protocol: |
1: Dolan ME, Pegg AE. O6-benzylguanine and its role in chemotherapy. Clin Cancer Res. 1997 Jun;3(6):837-47. PMID: 9815757.
2: Zhang J, Stevens MF, Bradshaw TD. Temozolomide: mechanisms of action, repair and resistance. Curr Mol Pharmacol. 2012 Jan;5(1):102-14. doi: 10.2174/1874467211205010102. PMID: 22122467.
3: Hindle A, Koneru B, Makena MR, Lopez-Barcons L, Chen WH, Nguyen TH, Reynolds CP. The O6-methyguanine-DNA methyltransferase inhibitor O6-benzylguanine enhanced activity of temozolomide + irinotecan against models of high-risk neuroblastoma. Anticancer Drugs. 2021 Mar 1;32(3):233-247. doi: 10.1097/CAD.0000000000001020. PMID: 33323683; PMCID: PMC9255907.
4: Davis BM, Koç ON, Reese JS, Gerson SL. O6-benzylguanine-resistant mutant MGMT genes improve hematopoietic cell tolerance to alkylating agents. Prog Exp Tumor Res. 1999;36:65-81. doi: 10.1159/000061986. PMID: 10386065.
5: Friedman HS, Keir S, Pegg AE, Houghton PJ, Colvin OM, Moschel RC, Bigner DD, Dolan ME. O6-benzylguanine-mediated enhancement of chemotherapy. Mol Cancer Ther. 2002 Sep;1(11):943-8. PMID: 12481416.
6: Tacastacas JD, Chan DV, Carlson S, Gerson SL, Dowlati A, Fu P, Lu K, Groft S, Rosenjack J, Honda K, McCormick TS, Cooper KD. Evaluation of O6-Benzylguanine- Potentiated Topical Carmustine for Mycosis Fungoides: A Phase 1-2 Clinical Trial. JAMA Dermatol. 2017 May 1;153(5):413-420. doi: 10.1001/jamadermatol.2016.5793. Erratum in: JAMA Dermatol. 2017 May 1;153(5):479. PMID: 28199478; PMCID: PMC5817489.
7: Tserng KY, Ingalls ST, Boczko EM, Spiro TP, Li X, Majka S, Gerson SL, Willson JK, Hoppel CL. Pharmacokinetics of O6-benzylguanine (NSC637037) and its metabolite, 8-oxo-O6-benzylguanine. J Clin Pharmacol. 2003 Aug;43(8):881-93. doi: 10.1177/0091270003256060. PMID: 12953345.
8: Ramalho MJ, Loureiro JA, Coelho MAN, Pereira MC. Factorial Design as a Tool for the Optimization of PLGA Nanoparticles for the Co-Delivery of Temozolomide and O6-Benzylguanine. Pharmaceutics. 2019 Aug 10;11(8):401. doi: 10.3390/pharmaceutics11080401. PMID: 31405159; PMCID: PMC6722980.
9: Pegg AE, Kanugula S, Edara S, Pauly GT, Moschel RC, Goodtzova K. Reaction of O6-benzylguanine-resistant mutants of human O6-alkylguanine-DNA alkyltransferase with O6-benzylguanine in oligodeoxyribonucleotides. J Biol Chem. 1998 May 1;273(18):10863-7. doi: 10.1074/jbc.273.18.10863. PMID: 9556560.
10: Dolan ME, Roy SK, Fasanmade AA, Paras PR, Schilsky RL, Ratain MJ. O6-benzylguanine in humans: metabolic, pharmacokinetic, and pharmacodynamic findings. J Clin Oncol. 1998 May;16(5):1803-10. doi: 10.1200/JCO.1998.16.5.1803. PMID: 9586894.
