title: Synthesis and DNA cleavage activity of artificial receptor 1,4,7-triazacyclononane containing guanidinoethyl and hydroxyethyl side arms.
abstract: A novel phosphodiester receptor 1-(2-guanidinoethyl)-4-(2-hydroxyethyl)-1,4,7-triazacyclononane hydrochloride 1 was synthesized. DNA cleavage efficiency of 1 exhibits remarkable increases compared with its ZnII complex and corresponding nonguanidinium compound N-(2-hydroxyethyl)-1,4,7-triazacyclononane and parent 1,4,7-triazacyclononane. Kinetic data of DNA cleavage promoted by 1 fit to a Michaelis-Menten-type equation with kmax of 0.160 h-1 giving 107-fold rate acceleration over uncatalyzed DNA. The acceleration is driven by the spatial proximity of the nucleophilic hydroxyl group and the electrophilic activation for the phosphodiester by the guanidinium group.
authors.affiliation: Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P.R. China.
authors.forename: Xin
authors.initials: X
authors.lastname: Sheng
authors.forename: Xiao-Min
authors.initials: XM
authors.lastname: Lu
authors.forename: Jing-Jing
authors.initials: JJ
authors.lastname: Zhang
authors.forename: Yue-Ting
authors.initials: YT
authors.lastname: Chen
authors.forename: Guo-Yuan
authors.initials: GY
authors.lastname: Lu
authors.forename: Ying
authors.initials: Y
authors.lastname: Shao
authors.forename: Fang
authors.initials: F
authors.lastname: Liu
authors.forename: Qiang
authors.initials: Q
authors.lastname: Xu
mesh_terms: D053938:DNA Fragmentation / Q000187:drug effects; D004278:DNA, Superhelical / Q000187:drug effects*; D019791:Guanidine / Q000737:chemistry; D006146:Guanidines / Q000138:chemical synthesis*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D009690:Nucleic Acid Conformation; D010957:Plasmids / Q000187:drug effects
chemical_list: C518837:1-(2-guanidinoethyl)-4-(2-hydroxyethyl)-1,4,7-triazacyclononane hydrochloride; D004278:DNA, Superhelical; D006146:Guanidines; D006571:Heterocyclic Compounds; C075712:1,4,7-triazacyclononane; D019791:Guanidine