TY - JOUR
T1 - Human cytotoxicity and octanol/water partition coefficients of fluorinated ionic liquids
AU - Vieira, Nicole S.M.
AU - Bastos, Joana C.
AU - Rebelo, Luís P. N.
AU - Matias, Ana
AU - Araújo, João M. M.
AU - Pereiro, Ana B.
N1 - Financial support from FCT/MCTES (Portugal), through: grant SFRH/BD/100563/2014 (N.S.M.V.) and PD/BD/135078/2017 (J.C.B.); Investigator FCT 2014 (IF/00190/2014 to A.B.P and IF/00210/2014 to J.M.M.A.); and projects PTDC/QEQ-EPR/5841/2014, PTDC/QEQ-FTT/3289/2014 and IF/00210/2014/CP1244/CT0003. This work was also supported by the Associate Laboratory for Green Chemistry LAQV which is financed by national funds from FCT/MCTES (UID/QUI/50006/2013) and co-financed by the ERDF under the PT2020 Partnership Agreement (POCI-01-0145-FEDER - 007265).
PY - 2019/2/1
Y1 - 2019/2/1
N2 - 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.
AB - 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.
KW - 1-Octanol/water partition coefficient
KW - Cytotoxicity
KW - Fluorinated ionic liquids
KW - Hydrophilic/lipophilic balance
UR - http://www.scopus.com/inward/record.url?scp=85055754667&partnerID=8YFLogxK
U2 - 10.1016/j.chemosphere.2018.10.159
DO - 10.1016/j.chemosphere.2018.10.159
M3 - Article
C2 - 30390588
AN - SCOPUS:85055754667
SN - 0045-6535
VL - 216
SP - 576
EP - 586
JO - Chemosphere
JF - Chemosphere
ER -