O6-Benzylguanine

O6-Benzylguanine, a guanine analog, is the DNA repair enzyme O6-alkylguanine-DNA alkyltransferase (MGMT/AGT) inhibitor. O6-Benzylguanine acts as an AGT substrate, which transfers its benzyl group to the AGT cysteine residue, thereby irreversibly inactivating AGT and preventing DNA repair. O6-Benzylguanine induces tumor cell apoptosis. Antineoplastic activity.

Product information

CAS Number: 19916-73-5

Molecular Weight: 241.25

Formula: C12H11N5O

Chemical Name: 6-(benzyloxy)-7H-purin-2-amine

Smiles: NC1=NC(OCC2C=CC=CC=2)=C2NC=NC2=N1

InChiKey: KRWMERLEINMZFT-UHFFFAOYSA-N

InChi: 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)

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 110 mg/mL (455.96 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

The L3.6pl cells are relatively sensitive to O6-Benzylguanine (24-72 hours) in a dose- and time-dependent manner. The IC50 is 50 μg (at 48 hours). O6-Benzylguanine (50 μg; 48 hours) modulates p53 downstream target protein expression, induces apoptosis, and decreases cell proliferation. O6-Benzylguanine (50 μg; 48 hours) significantly decreases the MGMT transcriptional activity in L3.6pl.

In Vivo:

O6-Benzylguanine (100 μg; i.p.; daily for 35 days) inhibits pancreatic cancer cell growth and increases pancreatic cell sensitivity to Gemcitabine (100 mg/kg). O6-Benzylguanine inhibits pancreatic cancer cell proliferation and induces tumor cell apoptosis in vivo.

References:

1. Rabik CA, Njoku MC, Dolan ME. Inactivation of O6-alkylguanine DNA alkyltransferase as a means to enhance chemotherapy. Cancer Treat Rev. 2006;32(4):261‐276.
2. Konduri, Santhi D et al. Blockade of MGMT expression by O6 benzyl guanine leads to inhibition of pancreatic cancer growth and induction of apoptosis. Clinical cancer research : an official journal of the American Association for Cancer Research vol. 15,19 (2009): 6087-95.

Products are for research use only. Not for human use.