Quinone methide derivatives: important intermediates to DNA alkylating and DNA cross-linking actions.
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.
Wang
Ping
P
College of Chemistry and Molecular Sciences, Wuhan University, Hubei, Wuhan 430072, P. R. of China. zhouxiang65@hotmail.com
Song
Yang
Y
Zhang
Lixia
L
He
Hanping
H
Zhou
Xiang
X
D000477:Alkylating Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D000478:Alkylation / Q000187:drug effects; D003432:Cross-Linking Reagents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D004247:DNA / Q000737:chemistry; D018736:DNA Adducts / Q000737:chemistry; D006801:Humans; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D008956:Models, Chemical; D013678:Technology, Pharmaceutical / Q000379:methods / Q000639:trends
D000477:Alkylating Agents; D003432:Cross-Linking Reagents; D018736:DNA Adducts; D045563:Indolequinones; C068040:quinone methide; D004247:DNA