Human cytotoxicity and octanol/water partition coefficients of fluorinated ionic liquids

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 toxi...

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Published inChemosphere (Oxford) Vol. 216; pp. 576 - 586
Main Authors Vieira, Nicole S.M., Bastos, Joana C., Rebelo, Luís P.N., Matias, Ana, Araújo, João M.M., Pereiro, Ana B.
Format Journal Article
LanguageEnglish
Published England Elsevier Ltd 01.02.2019
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Summary: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 n = 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/w < 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. [Display omitted] •Human Cytotoxicity of FILs using MTS colorimetric assay.•Po/w of FILs using the experimental slow-stirring method.•FILs intrinsic tuneability allows to fine-tune the hydrophilic/lipophilic balance.•For all the FILs under study Po/w < 1.00 and consequently log BCF = 0.5.•Biocompatible FILs can be designed using short hydrogenated and fluorinated chains.
ISSN:0045-6535
1879-1298
DOI:10.1016/j.chemosphere.2018.10.159