title: N-propargyl-2-alkynylbenzothiazolium aza-enediynes: role of the 2-alkynylbenzothiazolium functionality in DNA cleavage.
abstract: The 2-alkynylbenzothiazolium salts 3a-d incorporating an N-propargyl moiety have been prepared as aza-enediyne analogues. While these aza-enediynes are shown to be modest DNA cleavage agents, DNA cleavage was also observed with the N-methyl-2-alkynylbenzothiazolium salt 4, which lacks the aza-enediyne moiety. The structural requirements for DNA cleavage, and the correlation of DNA cleavage efficiency with the propensity of these compounds to undergo nucleophilic addition by methanol support a proposed DNA cleavage mechanism involving DNA alkylation by appropriate 2-alkynyl-substituted benzothiazolium salts.
authors.affiliation: Division of Medicinal Chemistry, College of Pharmacy, University of Texas at Austin, Austin, TX 78712, USA.
authors.forename: D
authors.initials: D
authors.lastname: Kumar
authors.forename: W M
authors.initials: WM
authors.lastname: David
authors.forename: S M
authors.initials: SM
authors.lastname: Kerwin
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis / Q000494:pharmacology*; D004247:DNA / Q000737:chemistry / Q000187:drug effects*
chemical_list: D001372:Aza Compounds; D004247:DNA