title: DNA cleavage potency, cytotoxicity, and mechanism of action of a novel class of enediyne prodrugs.
abstract: We have discovered a novel class of (E)-3-acyloxy-4-(arylmethylidene)cyclodeca-1,5-diynes which exhibit promising enediyne-like DNA cleavage and cytotoxic activities. LC-MS analysis of the incubation mixture (pH 8.5, 37 degrees C) confirmed formation of 10-membered ring enediyne presumably via an allylic cation and suggested that the 1,4-benzenoid diradical might be one of the active species for DNA damage and cytotoxicity.
authors.forename: Wei-Min
authors.initials: WM
authors.lastname: Dai
authors.forename: Kwong Wah
authors.initials: KW
authors.lastname: Lai
authors.forename: Anxin
authors.initials: A
authors.lastname: Wu
authors.forename: Wataru
authors.initials: W
authors.lastname: Hamaguchi
authors.forename: Mavis Yuk Ha
authors.initials: MY
authors.lastname: Lee
authors.forename: Ling
authors.initials: L
authors.lastname: Zhou
authors.forename: Atsushi
authors.initials: A
authors.lastname: Ishii
authors.forename: Sei-ichi
authors.initials: S
authors.lastname: Nishimoto
mesh_terms: D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D004278:DNA, Superhelical / Q000737:chemistry*; D006844:Hydrocarbons, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011355:Prodrugs / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D000480:Alkynes; D000970:Antineoplastic Agents; D004278:DNA, Superhelical; D006844:Hydrocarbons, Cyclic; D011355:Prodrugs