Affiliations 

  • 1 School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia; Department of Chemical Sciences, Mountain Top University, KM 12, Lagos-Ibadan Express Way, Ogun State, Nigeria. Electronic address: poasekunowo@mtu.edu.ng
  • 2 School of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
  • 3 Molecular Entomology Research Group, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia; Entomology Division, Cocoa Research Institute of Ghana, P. O. Box 8, New Tafo-Akim, Ghana. Electronic address: wavicor@crig.org.gh
  • 4 Molecular Entomology Research Group, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Eur J Med Chem, 2018 Apr 25;150:601-615.
PMID: 29550733 DOI: 10.1016/j.ejmech.2018.03.029

Abstract

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 1H NMR, 13C 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 μg/mL. Especially, compound 8b exhibited promising anti-Staphylococcus aureus activity with a low MIC value (12.5 μg/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 (Kb = 3.627 × 106) than the complexes 5b-7b (2.177 × 106, 8.672 × 105 and 6.665 × 105, 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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.