Synthesis and characterization of nitrile functionalized silver(I)-N-heterocyclic carbene complexes: DNA binding, cleavage studies, antibacterial properties and mosquitocidal activity against the dengue vector, Aedes albopictus

摘要

A series of four benzimidazolium based nitrile functionalized mononuclear Ag(I) N-heterocyclic carbene and binuclear Ag(I) N-heterocyclic carbene (Ag(I)-NHC) hexafluorophosphate complexes (5b-8b) were synthesized by reacting the corresponding hexafluorophosphate salts (1b-4b) with Ag2O in acetonitrile, respectively. These compounds were characterized by H-1 NMR, C-13 NMR, IR, UV-visible spectroscopic techniques, elemental analyses and molar conductivity. Additionally, 8b was structurally characterized by single crystal X-ray diffraction technique. Preliminary in vitro antibacterial evaluation was conducted for all the compounds against two standard bacteria; gram positive (Staphylococcus aureus) and gram negative (Escherichia coli) bacterial strains. Most of the Ag(I)-NHC complexes (5b-8b) showed moderate to good antibacterial activity with MIC values in the range of 12.5-100 mu g/mL. Especially, compound 8b exhibited promising anti Staphylococcus aureus activity with a low MIC value (12.5 mu g/mL). However, all the hexafluorophosphate salts (1b-4b) were inactive against the bacteria strains. The preliminary interactive investigation revealed that the most active compound, 8b, could effectively intercalate into DNA to form 8b-DNA complex which shows a better binding ability for DNA (K-b = 3.627 x 10(6)) than the complexes 5b-7b (2.177 x 10(6), 8.672 x 10(5) and 6.665 x 10(5), respectively). Nuclease activity of the complexes on plasmid DNA and Aedes albopictus genomic DNA was time dependent, although minimal. The complexes were larvicidal to the mosquito, with 5b, 6b and 8b being highly active. Developmental progression from the larval to the adult stage was affected by the complexes, progressively being toxic to the insect's development with increasing concentration. These indicate the potential use of these complexes as control agents against bacteria and the dengue mosquito Ae. albopictus. (C) 2018 Elsevier Masson SAS. All rights reserved.