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

Donia Bensalah; Nevin Gurbuz; Ismail Özdemir; Rafik Gatri; Lamjed Mansour; Naceur Hamdi

doi:10.1155/2023/3066299

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

Bioinorg Chem Appl. 2023 May 26:2023:3066299. doi: 10.1155/2023/3066299. eCollection 2023.

Authors

Donia Bensalah¹, Nevin Gurbuz^{2

3}, Ismail Özdemir^{2

3}, Rafik Gatri⁴, Lamjed Mansour⁵, Naceur Hamdi⁶

Affiliations

¹ Research Laboratory of Environmental Sciences and Technologies (LR16ES09), Higher Institute of Environmental Sciences and Technology, University of Carthage, Hammam-Lif, Tunisia.
² İnönü University, Faculty of Science and Art, Department of Chemistry, Malatya 44280, Turkey.
³ İnönü University, Catalysis Research and Application Center, Malatya 44280, Turkey.
⁴ Laboratory of Selective and Heterocyclic Organic Synthesis Biological Evaluation (LR17ES01), Faculty of Sciences of Tunis, University of Tunis El Manar Campus, Tunis 1092, Tunisia.
⁵ Department of Zoology, College of Science, King Saud University, Riyadh, Saudi Arabia.
⁶ Department of Chemistry, College of Science and Arts at Arras, Qassim University, P.O. Box 53, Arras 51921, Saudi Arabia.

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.