Abstract
In this review, we discuss the advances in understanding the reactivity of quinone methide (QM) intermediates and the reversibility of DNA alkylation by QMs in the past two decades. QMs react with strong nucleophiles of DNA under kinetic control but reversibly. The effective lifetime of QMs can be extended through repeated capture and release from DNA adducts. A QM-acridine conjugate DNA cross-linking agent remains dynamic and “migrates” among DNA strands through multiple strand exchange reactions until forming stable adducts irreversibly. Self-adducts of QM-biopolymer conjugates exhibit strong capability to alkylate complementary DNA strands in a sequence specific manner.
Keywords: Alkylation, Cross-linking, Nucleic Acids, Peptide Nucleic Acids, Quinone Methide, Reversibility, Sequence Specificity, Strand Exchange.
Current Organic Chemistry
Title:Quinone Methides and Their Biopolymer Conjugates as Reversible DNA Alkylating Agents
Volume: 18 Issue: 1
Author(s): Huan Wang
Affiliation:
Keywords: Alkylation, Cross-linking, Nucleic Acids, Peptide Nucleic Acids, Quinone Methide, Reversibility, Sequence Specificity, Strand Exchange.
Abstract: In this review, we discuss the advances in understanding the reactivity of quinone methide (QM) intermediates and the reversibility of DNA alkylation by QMs in the past two decades. QMs react with strong nucleophiles of DNA under kinetic control but reversibly. The effective lifetime of QMs can be extended through repeated capture and release from DNA adducts. A QM-acridine conjugate DNA cross-linking agent remains dynamic and “migrates” among DNA strands through multiple strand exchange reactions until forming stable adducts irreversibly. Self-adducts of QM-biopolymer conjugates exhibit strong capability to alkylate complementary DNA strands in a sequence specific manner.
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Cite this article as:
Wang Huan, Quinone Methides and Their Biopolymer Conjugates as Reversible DNA Alkylating Agents, Current Organic Chemistry 2014; 18 (1) . https://dx.doi.org/10.2174/138527281801140121122736
DOI https://dx.doi.org/10.2174/138527281801140121122736 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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