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
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