Maleimide-based acyclic enediyne for efficient DNA-cleavage and tumor cell suppression. Issue 16 (9th March 2015)

• Record Type: Journal Article
• Authors: Song, Depeng; Sun, Shiyuan; Tian, Yu; Huang, Shuai; Ding, Yun; Yuan, Yuan; Hu, Aiguo
• Is Part Of: Journal of materials chemistry. Volume 3:Issue 16(2015)
• Page Start: 3195
• Page End: 3200
• Publication Date: 2015-03-09
• Subjects: Materials -- Periodicals; Chemistry, Analytic -- Periodicals; Biomedical materials -- Research -- Periodicals; 543.0284
• DOI: 10.1039/c4tb02018a
• Languages: English
• ISSNs: 2050-750X

Abstract

Abstract : A pH-sensitive acyclic enediyne (1 ) was synthesized for efficient DNA-cleavage and tumor cell suppression. Abstract : A pH-sensitive acyclic enediyne (1 ) was synthesized for efficient DNA-cleavage and tumor cell suppression. Unlike other acyclic enediynes, this novel enediyne transforms into a highly reactive enediyne (2 ) in an acidic environment only, which undergoes Bergman cyclization spontaneously at ambient temperature. An EPR study on the enediyne2 confirmed the generation of free radicals through Bergman cyclization. The activated enediyne induced DNA-cleavage and exhibited cytotoxicity towards various tumor cells under the action of diradicals arising from spontaneous Bergman cyclization at physiological temperature. These findings suggest a novel strategy of anticancer drug design, where the activation of the silent compound takes place under the acidic environment inside the tumor cells.