Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity

Ranke, Johannes; Müller, Anja; Bottin‐Weber, Ulrike; Stock, Frauke; Stolte, Stefan; Arning, Jürgen; Störmann, Reinhold; Jastorff, Bernd

doi:10.1016/j.ecoenv.2006.08.008

Cited by 326 publications

(283 citation statements)

References 35 publications

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“…This phenomenon is known as chemical hormesis, which is characterised by low-dose stimulation and high-dose inhibition (17). A similar hormetic effect of 1-n-octylmethylimidazolium tetrafl uoroborate [C 8 6 ], which is consistent with the results reported by Ranke et al (18).…”

Section: Discussionsupporting

confidence: 82%

“…Mammalian cell lines are routinely used for basal cytotoxicity studies (4), while continuous fi sh cell lines are used in the ecotoxicological assessment of chemicals and environmental samples (5). It is suggested that cytotoxicity tests using dedifferentiated cancer cells provide a quick and convenient fi rst information about the toxic potential of chemical substances (6). The effects of ionic liquids on cell viability have already been reported in wellcharacterised tumour mammalian cell lines such as HeLa (7), CaCo-2 (8), MCF7 (9), and PC12 (10).…”

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confidence: 99%

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Cytotoxic Effects of Imidazolium Ionic Liquids on Fish and Human Cell Lines

Cvjetko

Radošević

Tomica

et al. 2012

Archives of Industrial Hygiene and Toxicology

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Ionic liquids bring a promise of a wide range of "green" applications that could replace conventional volatile solvents. However, before these applications become large-scale, their toxicity needs to be investigated in order to predict the impact on human health and environment. In this study we assessed the cytotoxicity of imidazolium ionic liquids (in the concentrations between 0.1 mmol L -1 and 10 mmol L -1 ) in the ovarian fi sh cell line CCO and the human tumour cell line HeLa using the MTT cell viability assay. Our results showed that the most cytotoxic ionic liquid was 1-n-butyl-3-methylimidazolium bis(trifl uoro methylsulphonyl)imide, [BMIM][Tf 2 N], followed by 1-n-butyl-3-methylimidazolium tetrafl uoroborate [BMIM] [BF 4 ], 1-n-butyl-3-methylimidazolium hexafluorophosphate [BMIM] [PF 6 ], and 1,3-dimethylimidazolium hexafl uorophosphate [MMIM] [PF 6 ]. Generally, the effects were concentrationdependent. They also depended on the type of anion and the n-alkyl chain length. The comparison between the fi sh CCO and human HeLa cell lines suggests that CCO cells provide a good biological system for initial toxicity testing of ionic liquids that could replace in vivo bioassays.

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Section: Discussionsupporting

confidence: 82%

mentioning

confidence: 99%

Cytotoxic Effects of Imidazolium Ionic Liquids on Fish and Human Cell Lines

Cvjetko

Radošević

Tomica

et al. 2012

Archives of Industrial Hygiene and Toxicology

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“…7,39 Despite the scarce number of studies reporting toxicity data for these non-aromatic and acyclic families, the same tendency here described was also identified in literature. 40 Maginn and co-workers 40 It is widely accepted in the literature 41,42 that the toxicities of ionic liquids are related with their hydrophobicities. The lower toxicity of the ammonium compounds supports that they present a lower hydrophobic nature (higher polarities) than their corresponding phosphonium counterparts, which is in agreement with the infinite dilution activity coefficients reported.…”

Section: Microtox R Toxicity Testsmentioning

confidence: 99%

Understanding the impact of the central atom on the ionic liquid behavior: Phosphonium vs ammonium cations

Carvalho

Ventura²,

Batista³

et al. 2014

The Journal of Chemical Physics

132

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Density relaxation and particle motion characteristics in a non-ionic deep eutectic solvent (acetamide + urea): Time-resolved fluorescence measurements and all-atom molecular dynamics simulations J. Chem. Phys. 142, 034505 (2015) The influence of the cation's central atom in the behavior of pairs of ammonium-and phosphoniumbased ionic liquids was investigated through the measurement of densities, viscosities, melting temperatures, activity coefficients at infinite dilution, refractive indices, and toxicity against Vibrio fischeri. All the properties investigated are affected by the cation's central atom nature, with ammonium-based ionic liquids presenting higher densities, viscosities, melting temperatures, and enthalpies. Activity coefficients at infinite dilution show the ammonium-based ionic liquids to present slightly higher infinite dilution activity coefficients for non-polar solvents, becoming slightly lower for polar solvents, suggesting that the ammonium-based ionic liquids present somewhat higher polarities. In good agreement these compounds present lower toxicities than the phosphonium congeners. To explain this behavior quantum chemical gas phase DFT calculations were performed on isolated ion pairs at the BP-TZVP level of theory. Electronic density results were used to derive electrostatic potentials of the identified minimum conformers. Electrostatic potential-derived CHelpG and Natural Population Analysis charges show the P atom of the tetraalkylphosphonium-based ionic liquids cation to be more positively charged than the N atom in the tetraalkylammonium-based analogous IL cation, and a noticeable charge delocalization occurring in the tetraalkylammonium cation, when compared with the respective phosphonium congener. It is argued that this charge delocalization is responsible for the enhanced polarity observed on the ammonium based ionic liquids explaining the changes in the thermophysical properties observed. © 2014 AIP Publishing LLC.

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“…Their introduction into industrial processes, together with their organic character, motivated the first studies of their interaction with biomolecules and bio-organisms (Petkovic et al 2011). As a result, several studies have highlighted their toxicity on living organisms (Pretti et al 2006;Bernot et al 2005;Ranke et al 2006Ranke et al , 2007aStolte et al 2007;Kulacki and Lamberti 2008). Toxicity is also a measure of the high affinity between RTILs and biosystems.…”

Section: Introductionmentioning

confidence: 99%

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

Benedetto

2017

Biophys Rev

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Room-temperature ionic liquids (RTIL) are a new class of organic salts whose melting temperature falls below the conventional limit of 100°C. Their low vapor pressure, moreover, has made these ionic compounds the solvents of choice of the so-called green chemistry. For these and other peculiar characteristics, they are increasingly used in industrial applications. However, studies of their interaction with living organisms have highlighted mild to severe health hazards. Since their cytotoxicity shows a positive correlation with their lipophilicity, several chemical-physical studies of their interactions with biomembranes have been carried out in the last few years, aiming to identify the molecular mechanisms behind their toxicity. Cation chain length and anion nature of RTILs have seemed to affect lipophilicity and, in turn, their toxicity. However, the emerging picture raises new questions, points to the need to assess toxicity on a case-by-case basis, but also suggests a potential positive role of RTILs in pharmacology, bio-medicine and bio-nanotechnology. Here, we review this new subject of research, and comment on the future and the potential importance of this emerging field of study.

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Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity

Cited by 326 publications

References 35 publications

Cytotoxic Effects of Imidazolium Ionic Liquids on Fish and Human Cell Lines

Cytotoxic Effects of Imidazolium Ionic Liquids on Fish and Human Cell Lines

Understanding the impact of the central atom on the ionic liquid behavior: Phosphonium vs ammonium cations

Room-temperature ionic liquids meet bio-membranes: the state-of-the-art

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