Abstract
Abstract DNA interstrand cross-links (ICLs) are the sources of the cytotoxicity of many anticancer agents. DNA cross-linking agents are used as anticancer agents, for DNA damage and repair study, for nucleic acid detection, and for construction of DNA nanomaterials. This chapter summarizes various novel methods and chemical reagents recently developed for inducing DNA ICL formation, the mechanisms involved for DNA cross-linking, and their applications. It starts by presenting photoinduced DNA ICL formation via [2+2] cycloaddition reaction, quinone methide, or carbocation formation. It then discusses novel DNA cross-linking agents activated by various chemical agents, including the arylboronate or boronic acid derivatives activated by hydrogen peroxide, silyl-protected bifunctional phenol derivatives triggered by fluoride, and phenyl selenides or furan analogs activated by oxidation reagents. General mechanisms involved formation of alkylating species, including quinone methide, nitrogen mustard, methide analogs, and enal formation. Enzyme-activated DNA cross-linking agents and their application for targeting cancer cells are also explained. By the end of the chapter, DNA ICL formation induced by “click” chemistry is highlighted.
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