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O(6)-Benzylguanine

  Cat. No.:  DC33398   Featured
Chemical Structure
19916-73-5
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More than 5000 active chemicals with high quality for research!
Field of application
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.
Chemicals PropertiesBiological activity COA & MSDSRelated productsDatasheet
Cas No.: 19916-73-5
Chemical Name: 6-(benzyloxy)-1H-purin-2-amine
Synonyms: O(6)-Benzylguanine; CCRIS 9383; CCRIS9383; CCRIS-9383; NSC637037; NSC 637037; NSC-637037
SMILES: NC(N=C1OCC2=CC=CC=C2)=NC3=C1NC=N3
Formula: C12H11N5O
M.Wt: 241.25
Purity: >98%
Sotrage: 2 years -20°C Powder, 2 weeks 4°C in DMSO, 6 months -80°C in DMSO
Description: 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[1][2].
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)[2]. O6-Benzylguanine inhibits pancreatic cancer cell proliferation and induces tumor cell apoptosis in vivo[2]. Animal Model: Male athymic nude mice (NCI-nu) (bearing human pancreatic cancer L3.6pl cells)[2] Dosage: 100 μg Administration: i.p; daily for 35 days Result: Significantly decreased median tumor volume and weight.
In Vitro: 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[1][2].
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.
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