A thiol-inducible and quick-response DNA cross-linking agent.

Affiliation

State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Gansu, Lanzhou 730000, China. Electronic address: [Email]

Abstract

Three new 2,4-dinitrobenzenesulfonyl derivatives 1-3 were successfully prepared for the first time using a simple process. They were efficiently triggered by thiols (glutathione and l-cysteine) to release the corresponding phenol derivatives (4-6) within 5 min. The quick response of 1-3 toward thiols was determined by 1H NMR and HPLC. Moreover, our results indicated that 1 could induce DNA cross-linking in the presence of glutathione, probably due to the quinone methide formation of phenol intermediate 4 followed by departure of 2,4-dinitrobenzenesulfonyl group.

Keywords

2,4-Dinitrobenzenesulfonyl,Antitumor agents,DNA cross-linking,Quinone methide,