Synthesis and characterization of polyamine-based biomimetic catalysts as artificial ribonuclease.
Several polyamine derivatives (I-V) conjugated with or without an intercalative moiety were prepared as ribonuclease mimics. Although no DNA-cleaving activity was observed for all compounds tested, mimics I, III, and V bearing an intercalative moiety along with the primary amine and/or imidazole moieties exhibited potent RNA-cleaving activity at near physiological pH. The RNA-cleaving reactions of the compounds show characteristic bell-shaped pH dependency, and the optimal pH values for III and V were well correlated to the pKa values of their active sites, primary amine, and imidazole moieties.
Shinozuka
K
K
Department of Chemistry, Faculty of Engineering, Gunma University, Kiryu City, Japan. sinozuka@chem.gunma-u.ac.jp
Nakashima
Y
Y
Shimizu
K
K
Sawai
H
H
D001665:Binding Sites; D002384:Catalysis; D006863:Hydrogen-Ion Concentration; D007093:Imidazoles / Q000737:chemistry; D018716:Molecular Mimicry; D011073:Polyamines / Q000138:chemical synthesis*; D012335:RNA, Ribosomal / Q000737:chemistry; D012260:Ribonucleases / Q000737:chemistry*
D007093:Imidazoles; D011073:Polyamines; D012335:RNA, Ribosomal; D012260:Ribonucleases