Quinone Methide Derivatives: Important Intermediates to DNA Alkylating and DNA Cross-linking Actions

Abstract

Induced DNA interstrand cross-links by chemical agents or photoactivation play very important roles for cancer therapy. Several important clinical drugs (e.g. cisplatin, psoralens, and mitomycin C) are known to induce DNA ISC formation, which can disrupt cell maintenance and replication. Among these anti-tumor agents, one mechanism was involved in quinone methide intermediate. Quinone methide derivative has played important roles in organic syntheses as well as in chemical and biological processes. This review is concerned with current efforts of quinone methide derivatives to DNA alkylation and DNA cross-links. The latest advances in this field will be reviewed in this article. The chemical and physical properties of quinone methide derivatives, the interactions between nucleobases and quinone methide derivatives, the reactions with phosphodiester, DNA alkylation and cross-link via quinone methide intermediate action will be discussed.

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“…14 QM se mogu generirati reakcijama u osnovnom stanju (termički), 15 kao i fotokemijskim metodama. 1 Osim u tu svrhu, u literaturi su opisane brojne druge primjene QM-a, npr. kao antimalarika, 16 inhibitora mitohondrijske respiracije, 17 inhibitora glukuronidaze 18 te za detekciju fiziološki važnih tiola.…”

Bioactivation I: Bioactivation by Cytochrome P450s

“…These intermediates are quite reactive (depending on the substituents on the aromatic ring) and the reactivity is ascribed to the presence of α,β-unsaturated carbonyl or imine moieties, that can react with biologically important nucleophiles via a 1,4-Michael addition reaction [148][149][150][151][152][153].…”