ABSTRACT
The use of fluorinated ionic liquids (FILs) as novel materials in biological and pharmaceutical applications is an emerging research field. The knowledge of their cytotoxicity and that of 1-octanol/water partition coefficients are essential to assess their environmental risks, to estimate their toxicity and activity, or the hydrophilic/lipophilic balance, as well as to explore their properties as solvents in extraction processes or for successful drug design. The study of the cytotoxicity in four different human cell lines and the experimental measurement of the partition coefficient between 1-octanol and water (Po/w), using the slow-stirring method, were carried out for several FILs. In both studies, the effect of the cation ([C2C1Im]+, [C2C1py]+, [C4C1pyr]+, [N1112(OH)]+, or [N4444]+), the cationic alkyl side-chain length ([CnC1Im]+, with nâ¯=â¯2, 6, 8 or 12), and the anionic fluorinated chain length/anionic fluorinated domain size ([C4F9SO3]¯, [C8F17SO3]¯, or [N(C4F9SO3)2]¯) were analysed. The results reveal that both toxicity and partition properties are mainly influenced by the size of the cationic hydrogenated alkyl side-chain and that of the anionic fluorinated domain. The intrinsic tuneability of the FILs allows for their selection according to the lipophilic or hydrophilic character of the target biological system under consideration. The toxicity studies corroborate the biocompatible nature of some FILs tested in this work. Along, for all the FILs under study Po/wâ¯<â¯1.00. Accordingly, a decadic logarithm of the bioconcentration factor in fish of 0.5 would be estimated, which is below the regulatory endpoint used by regulatory agencies.
Subject(s)
Halogenation , Human Umbilical Vein Endothelial Cells/pathology , Ionic Liquids/adverse effects , Keratinocytes/pathology , Octanols/chemistry , Water/chemistry , Caco-2 Cells , Cell Survival , Cells, Cultured , Hep G2 Cells , Human Umbilical Vein Endothelial Cells/drug effects , Humans , Hydrophobic and Hydrophilic Interactions , Keratinocytes/drug effectsABSTRACT
We demonstrate that fluorinated ionic liquids reduce the impact of the addition of water upon the ionic liquid's H-bond acceptance ability. This is a key factor to obtain functionalized materials to be used e.g. in the dissolution of biomolecules, extraction processes or material engineering.
