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.
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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