The synthesis of decyl-o-phenanthrolinium organic salt and a study of the impact of anion type on in vitro antibacterial activities

Abstract

According to evidence in the literature, organic salts have an affinity for biological membranes that makes them easily absorbed into cells and capable of having a wide range of biological effects, such as broad antibacterial potential and anticancer activity. The present work describes the preparation of three organic salts with a common decyl-1,10-phenanthrolinium cation ([C22H25N2]+) differing in the anions (Br−, PF6− and (CF3SO2)2N−). The synthesis was confirmed using spectrometry methods (NMR (1H 13C, 19F, 31P), ESI MS, Uv-Vis), CHNSBr elemental and thermal analysis as well as conductivity measurements. In vitro biological activities were tested on two Gram-positive (Staphylococcus aureus (S. aureus), Streptococci pyogenes (S. pyogenes)) and two Gram-negative (Escherichia coli (E. Coli) and Klebsiellae pneumoniae (K. Pneumoniae)) bacteria and compared with a commercial antibiotic (Gentamicin). The salt with the halide anion demonstrated better inhibition activities than the commercially available gentamicin. Their ion-conductivity in ethanol was found to decrease in the order [C22H25N2][PF6], [C22H25N2][(CF3SO2)2N] and [C22H25N2]Br while, their thermal stability was found to increase in the order [C22H29N2]Br, [C22H29N2][PF6], and [C22H29N2][(CF3SO2)2N]. The minimum inhibitory concentration (MIC) values show that the salts could inhibit bacterial growth at concentrations as low as 50 μg/L. Passing the cytotoxicity investigations, these salts can be considered as alternative antibiotics in combating the emerging drug resisting bacteria.

Keywords

• Organic salts
• 1,10-Phenanthroline
• Quaternization
• Anion exchange
• Antimicrobial activity