Silver and selenium compounds of benzimidazolium salts containing fluorine substituents: Synthesis, characterization, and evaluation of anticancer potentials

The applications of fluorine in the field of drug design are expanding at a rapid pace. The development of synthetic methodologies has enabled the creation of new fluorinated motifs. Benzimidazolium salts represent a significant source of N-heterocyclic carbenes (NHCs), a distinctive class of ligands. These salts have a wide range of applications due to their notable qualities. The present study encompasses the synthesis of four novel benzimidazolium salts (1a-d) substituted with 2,6-difluorobenzyl moiety. Subsequently, the prepared salts were utilized in the synthesis of silver complexes (2a-d) and selenium compounds (3a-d). The structures of all compounds were elucidated by ¹H, ¹³C, ¹⁹F NMR, HRMS, FT-IR spectroscopies, and elemental analysis techniques. The incorporation of a fluorine atom into the molecular structure of a compound has been known to induce substantial alterations in the biological responses of mentioned compound. Therefore, the cytotoxic effect of these compounds was also evaluated using the MTT assay on HCT116 and L929 cell lines. Acridine orange (AO)/ethidium bromide (EB) staining were used for the detection of apoptosis. Notably, cytotoxicity assays showed that compound 3d displayed approximately 22-fold higher potency against HCT116 than cisplatin. Taken together, this enhanced efficacy signifies the promising role of silver and selenium compounds of benzimidazolium salts containing fluorine substituents in anticancer therapies.