PMID: 6538490Feb 1, 1984Paper

Alkylation of DNA by the new anticancer agent 3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone (AZQ)

European Journal of Cancer & Clinical Oncology
C L KingT L Loo

Abstract

The bifunctional cross-linking activity of 3,6-diaziridinyl-2,5-bis(carboethoxyamino)-1,4-benzoquinone (AZQ, NSC 182986) on isolated calf thymus DNA was studied, using ethidium bromide fluorescence assay. Between 1 and 350 microM AZQ produced a dose-dependent cross-linking effect in the presence of a 10-fold excess of sodium borohydride. No cross-linking was observed in the absence of the reducing agent. AZQ can also be activated by NADH and NADPH at pH 4. The AZQ cross-linking activity exhibited a strong pH dependency, highest at acidic pH, lower at alkaline pH and not seen under neutral conditions. It was also significantly inhibited under anaerobic conditions. At pH 5 the binding ratio was 1 molecule of AZQ per 191 bases at an AZQ dose of 300 microM. Our results suggest that reduced AZQ behaved like a bifunctional alkylating agent.

References

Feb 1, 1979·Journal of Pharmaceutical Sciences·J S DriscollR I Geran
Nov 1, 1976·Journal of Medicinal Chemistry·F ChouJ S Driscoll
Nov 29, 1963·Science·H S SCHWARTZF S PHILIPS

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Citations

Jan 1, 1987·Pharmacology & Therapeutics·G Powis
Jan 1, 1989·Free Radical Biology & Medicine·G Powis
May 1, 1988·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·B NguyenP L Gutierrez
Jan 1, 1987·Chemico-biological Interactions·P L GutierrezP S Callery
Dec 24, 2018·Chemical Society Reviews·Amit SharmaJong Seung Kim
Jun 1, 1989·Ophthalmic Paediatrics and Genetics·L WhiteV Tobias
Jan 1, 1989·Free Radical Biology & Medicine·P L Gutierrez

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