Synthesis, Characterization, Antimicrobial Properties, and Antioxidant Activities of Silver-N-Heterocyclic Carbene Complexes

Abstract

The emergence of antimicrobial resistance has become a major handicap in the fight against bacterial infections, prompting researchers to develop new, more effective, and multimodal alternatives. Silver and its complexes have long been used as antimicrobial agents in medicine because of their lack of resistance to silver, their low potency at low concentrations, and their low toxicity compared to most commonly used antibiotics. N-Heterocyclic carbenes (NHCs) are widely used for coordination of transition metals, mainly in catalytic chemistry. In this study, several N-alkylated benzimidazolium salts 2a–j were synthesized. Then, the N-heterocyclic carbene (NHC) precursor was treated with Ag2O to give silver (I) NHC complexes (3a–j) at room temperature in dichloromethane for 48 h. Ten new silver-NHC complexes were fully characterized by nuclear magnetic resonance (NMR), Fourier transform infrared spectroscopy (FT-IR), elemental analysis, and LC-MSMS (for complexes) techniques. The antibacterial and antioxidant activities of salt 2 and its silver complex 3 were evaluated. All of these complexes were more effective against bacterial strains than comparable ligands. With MIC values ranging from 6.25 to 100 g/ml, the Ag-NHC complex effectively showed strong antibacterial activity. Antioxidant activity was also tested using conventional techniques, such as 2, 2-diphenyl-1-picrylhydrazine (DPPH) and hydrogen peroxide scavenging assays. In DPPH and ABTS experiments, compounds 3a, 3b, 3c, 3e, 3g, and 3i showed significant clearance.