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.
Related Books
2-Deoxy-D-Glucose: Chemistry and Biology
Chiral Ionic Liquids: Applications in Chemistry and Technology
Basics of Organic Chemistry: A Textbook for Undergraduate Students
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
40