Membrane partitioning of ionic liquid cations, anions and ion pairs – Estimating the bioconcentration potential of organic ions

Dołżonek, Joanna; Cho, Chul-Woong; Stepnowski, Piotr; Markiewicz, Marta; Thöming, Jorg; Stolte, Stefan

doi:10.1016/j.envpol.2017.04.079

Cited by 51 publications

(43 citation statements)

References 81 publications

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“…PFUnDA is the only outlier to this trend. A deviation from linearity in K mem/w with increasing number of carbon atoms in the side chain was reported in the literature for 1-alkyl-3-methylimidazolium derivatives . The so-called “cut-off effect” was supposedly caused by a reduced diffusibility due to the size and flexibility of the longer alkyl side chains.…”

Section: Resultsmentioning

confidence: 93%

Membrane/Water Partitioning and Permeabilities of Perfluoroalkyl Acids and Four of their Alternatives and the Effects on Toxicokinetic Behavior

Ebert

Allendorf

Berger

et al. 2020

Environ. Sci. Technol.

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The search for alternatives to bioaccumulative perfluoroalkyl acids (PFAAs) is ongoing. New, still highly fluorinated alternatives are produced in hopes of reducing bioaccumulation. To better estimate this bioaccumulative behavior, we performed dialysis experiments and determined membrane/ water partition coefficients, K mem/w , of six perfluoroalkyl carboxylic acids (PFCAs), three perfluoroalkanesulfonic acids, and four alternatives. We also investigated how passive permeation might influence the uptake kinetics into cells, measuring the passive anionic membrane permeability P ion through planar lipid bilayers for six PFAAs and three alternatives. Experimental K mem/w and P ion were both predicted well by the COSMO-RS theory (log RMSE 0.61 and 0.46, respectively). K mem/w values were consistent with the literature data, and alternatives showed similar sorption behavior as PFAAs. Experimental P ion values were high enough to explain observed cellular uptake by passive diffusion with no need to postulate the existence of active uptake processes. However, predicted pK a and neutral permeabilities suggest that also the permeation of the neutral species should be significant in case of PFCAs. This can have direct consequences on the steady-state distribution of PFAAs across cell membranes and thus toxicity. Consequently, we propose a model to predict pH-dependent baseline toxicity based on K mem/w , which considers the permeation of both neutral and anionic species.

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Section: Resultsmentioning

confidence: 93%

Membrane/Water Partitioning and Permeabilities of Perfluoroalkyl Acids and Four of their Alternatives and the Effects on Toxicokinetic Behavior

Ebert

Allendorf

Berger

et al. 2020

Environ. Sci. Technol.

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“…This occurred especially for more hydrophobic substances such as nonylphenol and triclosan, whereas, for weakly sorbing compounds, species-specific partitioning coefficients of the ionic species were at least one order of magnitude smaller. Whereas predictions solely based on the log K OW which is the classic parameter for estimating hydrophobicity fail to predict accumulation of ionic species [ 9 ], there is some evidence that polar species can accumulate within organisms as well and play an important role in bioaccumulation in fat [ 7 , 14 ]. In addition, carbon nanotubes can sorb ionic liquids [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

A combined experimental and modeling study to evaluate pH-dependent sorption of polar and non-polar compounds to polyethylene and polystyrene microplastics

et al. 2018

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BackgroundThe contamination of aquatic ecosystems with both anthropogenic pollutants and particles in particular (microscopic) plastic debris items is of emerging concern. Since plastic particles can accumulate contaminants and potentially facilitate their transport, it is important to properly investigate sorption mechanisms. This is especially required for a large variety of chemicals that can be charged under environmental conditions and for which interactions with particles may hence go beyond mere partitioning.ResultsIn this study, sorption experiments with two types of microplastic particles (polyethylene and polystyrene) and 19 different contaminants (pesticides, pharmaceuticals, and personal care products) were performed at three different pH values. We could show that sorption to plastic particles is stronger for hydrophobic compounds and that neutral species usually contribute more to the overall sorption. Bulk partitioning coefficients were in the same order of magnitude for polyethylene and polystyrene. Furthermore, our results confirm that partition coefficients for polar compounds can only be accurately determined if the solid-to-liquid ratio in batch experiments is more than 6–7 orders of magnitude higher than any plastic concentration detected in the environment. Consequently, only a minor fraction of pollutants in water bodies is associated with microplastics.ConclusionsAlthough neutral species primarily dominate the overall sorption, hydrophobic entities of ionic species cannot be neglected for some compounds. Notwithstanding, our results show that since microplastic concentrations as currently observed in the environment are very low, they are only a relevant sorbent for strongly hydrophobic but not for polar compounds.Electronic supplementary materialThe online version of this article (10.1186/s12302-018-0155-z) contains supplementary material, which is available to authorized users.

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“…Taking into consideration the in vitro studies conducted so far on the bioconcentration potential of ILs, partitioning experiments using phosphatidylocholine have been carried out. The study revealed that ILs may bind to the phospholipid membrane to a great extent (much greater than assumed before on the basis of the logKow) and hence can have a potential for bioaccumulation (Dołżonek et al 2017). Therefore, as a complementary study, it is necessary to assess their interaction with proteins so as to obtain more data for true bioconcentration estimations.…”

Section: Introductionmentioning

confidence: 81%

“…As it has been recently shown, the membrane-water partition coefficient (log K MW ) of the cation is altered by the concentration of anions [B(CN) 4 ] − and [(FSO 2 ) 2 N] − indicating stronger partitioning of [C( 12)mim] + probably due to ion pairing, reduction of repulsive interaction with choline by anion adsorption on bilayer surfaces, neutralization of the charge of choline and/or changes of lipid bilayer integrity (Dołżonek et al 2017). Furthermore, according to the study by Figueiredo et al (2013) organic anions are less hydrated compared to simple inorganic anions, and thus, their availability to interact with proteins could be higher.…”

Section: Evaluation Of the Influence Of Anions On The Affinity Of Cations Of Ionic Liquids To Proteinmentioning

confidence: 99%

Interaction of ionic liquids with human serum albumin in the view of bioconcentration: a preliminary study

et al. 2022

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Bioaccumulation potential is critical in PBT and risk assessment of chemicals. However, for ionic liquids (ILs), this aspect remains neglected. It is especially important to fill this gap, because for this group of compounds, existing data confirm their risk of being environmentally persistent and toxicity. Moreover, considering preliminary reports on the interactions of ILs with lipids, it may be assumed that ILs have a higher potential for bioaccumulation than indicated by previous estimations built upon octanol–water partition coefficients. Moreover, the bioconcentration of ionizable chemical compounds may also be strongly related to plasma protein contents. Therefore, in this work, the affinity of a set of imidazolium cations and organic anions, and their combination to human serum albumin (HSA) was determined. The obtained results reveal that both cations and anions can be strongly bound to HSA, and blood proteins might play an important role in overall bioaccumulation. Furthermore, it was observed that HSA binding properties towards IL cations depend on the hydrophobicity of cations. The obtained data also provide indication that cation–anion interaction may affect ILs ions affinity to HSA.

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Membrane partitioning of ionic liquid cations, anions and ion pairs – Estimating the bioconcentration potential of organic ions

Cited by 51 publications

References 81 publications

Membrane/Water Partitioning and Permeabilities of Perfluoroalkyl Acids and Four of their Alternatives and the Effects on Toxicokinetic Behavior

Membrane/Water Partitioning and Permeabilities of Perfluoroalkyl Acids and Four of their Alternatives and the Effects on Toxicokinetic Behavior

A combined experimental and modeling study to evaluate pH-dependent sorption of polar and non-polar compounds to polyethylene and polystyrene microplastics

Interaction of ionic liquids with human serum albumin in the view of bioconcentration: a preliminary study

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