Hydrogen peroxide activated quinone methide precursors with enhanced DNA cross-linking capability and cytotoxicity towards cancer cells.

ABSTRACT: Quinone methide (QM) formation induced by endogenously generated H₂O₂ is attractive for biological and biomedical applications. To overcome current limitations due to low biological activity of H₂O₂-activated QM precursors, we are introducing herein several new arylboronates with electron donating substituents at different positions of benzene ring and/or different neutral leaving groups. The reaction rate of the arylboronate esters with H₂O₂ and subsequent bisquinone methides formation and DNA cross-linking was accelerated with the application of Br as a leaving group instead of acetoxy groups. Additionally, a donating group placed meta to the nascent exo-methylene group of the quinone methide greatly improves H₂

SUBMITTER: Wang Y 

PROVIDER: S-EPMC5652303 | biostudies-literature | 2017 Jun

REPOSITORIES: biostudies-literature