Synthesis and DNA cleavage activity of artificial receptor 1,4,7-triazacyclononane containing guanidinoethyl and hydroxyethyl side arms.
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.
Sheng
Xin
X
Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P.R. China.
Lu
Xiao-Min
XM
Zhang
Jing-Jing
JJ
Chen
Yue-Ting
YT
Lu
Guo-Yuan
GY
Shao
Ying
Y
Liu
Fang
F
Xu
Qiang
Q
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
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