O6-Benzylguanine sodium | CAS#19916-73-5 | MGMT inhibitor

MedKoo Cat#: 208169 | Name: O6-Benzylguanine sodium

Description:

WARNING: This product is for research use only, not for human or veterinary use.

O(6)-Benzylguanine is an MGMT inhibitor that prevents the repair of DNA damage induced by chemotherapeutics. It allows apoptosis and other mechanisms of cell death to occur. 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.

Chemical Structure

O6-Benzylguanine sodium

CAS#100994-97-6 (sodium)

Theoretical Analysis

MedKoo Cat#: 208169

Name: O6-Benzylguanine sodium

CAS#: 100994-97-6 (sodium)

Chemical Formula: C12H10N5NaO

Exact Mass: 241.0964

Molecular Weight: 263.24

Elemental Analysis: C, 54.75; H, 3.83; N, 26.61; Na, 8.73; O, 6.08

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

100994-97-6 (sodium) 19916-73-5 (free)

Synonym

O6-Benzylguanine, O6-Benzylguanine

IUPAC/Chemical Name

6-O-Benzylguanine; 6-Phenylmethoxy-7H-purin-2-amine sodium

InChi Key

CLONCOXJHKAGAL-UHFFFAOYSA-N

InChi Code

InChI=1S/C12H10N5O.Na/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,(H2-,13,14,15,16,17);/q-1;+1

SMILES Code

NC1=NC(OCC2=CC=CC=C2)=C3N=C[N-]C3=N1.[Na+]

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 263.24 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

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.