Imidazole and Imidazolium Antibacterial Drugs Derived from Amino Acids.

The antibacterial activity of imidazole and imidazolium salts is highly dependent upon their lipophilicity, which can be tuned through the introduction of different hydrophobic substituents on the nitrogen atoms of the imidazole or imidazolium ring of the molecule. Taking this into consideration, we have synthesized and characterized a series of imidazole and imidazolium salts derived from -valine and -phenylalanine containing different hydrophobic groups and tested their antibacterial activity against two model bacterial strains, Gram-negative and Gram-positive . Importantly, the results demonstrate that the minimum bactericidal concentration (MBC) of these derivatives can be tuned to fall close to the cytotoxicity values in eukaryotic cell lines.