Evidence of a reverse side-chain effect of tris(pentafluoroethyl)trifluorophosphate [FAP]-based ionic liquids against pathogenic bacteria

• Published in: Ecotoxicology and environmental safety 2018-02, Vol.148, p.467-472
• Main Authors: Weyhing-Zerrer, Nadine, Kalb, Roland, Oßmer, Rolf, Rossmanith, Peter, Mester, Patrick
• Format: Article
• Language: English
• Subjects: Antimicrobial activity; Bacteria; Gram-Negative Bacteria - drug effects; Hydrocarbons, Fluorinated - pharmacology; Hydrophobic and Hydrophilic Interactions; Ionic liquids; Ionic Liquids - pharmacology; Microbial Sensitivity Tests; Reverse side-chain effect; Solvents - chemistry; Structure-activity relationship (SAR); Toxicity
• ISSN: 0147-6513; 1090-2414
• DOI: 10.1016/j.ecoenv.2017.10.059

Increased interest in ionic liquids (ILs) is due to their designable and tunable unique physicochemical properties, which are utilized for a wide variety of chemical and biotechnological applications. ILs containing the tris(pentafluoroethyl)trifluorophosphate ([FAP]) anion have been shown to have excellent hydrolytic, electrochemical and thermal stability and have been successfully used in various applications. In the present study the influence of the cation on the toxicity of the [FAP] anion was investigated. Due to the properties of [FAP] ILs, the IL-toxicity of seven cations with [FAP] compared to [Cl] was examined by determination of minimum inhibitory (MIC) and minimum bactericidal concentrations (MBC) on six Gram-positive and six Gram-negative clinically-relevant bacteria. For the first time, to our knowledge, the results provide evidence for a decrease in toxicity with increasing alkyl side-chain length, indicating that the combination of both ions is responsible for this ‘reverse side-chain effect’. These findings could portend development of new non-toxic ILs as green alternatives to conventional organic solvents. [Display omitted] •Evidence of a ‘reverse side-chain effect’.•Increasing cation hydrophobicity leads to overall decreased toxicity of [FAP] ILs.•Non-toxic cations alter the toxicity of the toxic [FAP] anion.•Toxic cations in combination with the toxic [FAP] anion results in less- or non-toxic ILs.