References
- H. Sütterlin, R. Alexy, A. Coker, K. Kümmerer, Mixtures
of quaternary ammonium compounds and anionic organic
compounds in the aquatic environment: elimination and
biodegradability in the closed bottle test monitored by
LC-MS/MS, Chemosphere, 72 (2008) 479–484.
- J. Pernak, M. Smiglak, S.T. Griffin, W.L. Hough, T.B. Wilson,
A. Pernak, J. Zabielska-Matejuk, A. Fojutowski, K. Kita, R.D.
Rogers, Long alkyl chain quaternary ammonium-based ionic
liquids and potential applications, Green Chem., 8 (2006)
798–806.
- J. Pernak, J. Nawrot, M. Kot, B. Markiewicz, M. Niemczak, Ionic
liquids based stored product insect antifeedants, RSC Adv., 3
(2013) 25019–25029.
- N. Kreuzinger, M. Fuerhacker, S. Scharf, M. Uhl, O. Gans, B.
Grillitsch, Methodological approach towards the environmental
significance of uncharacterized substances—quaternary
ammonium compounds as an example, Desalination., 215
(2007) 209–222.
- E. Martínez-Carballo, A. Sitka, C. González-Barreiro, N.
Kreuzinger, M. Fürhacker, S. Scharf, O. Gans, Determination
of selected quaternary ammonium compounds by liquid
chromatography with mass spectrometry. Part I. Application to
surface, waste and indirect discharge water samples in Austria,
Environ. Pollut., 145 (2007) 489–496.
- E. Martínez-Carballo, C. González-Barreiro, A. Sitka, N.
Kreuzinger, S. Scharf, O. Gans, Determination of selected
quaternary ammonium compounds by liquid chromatography
with mass spectrometry. Part II. Application to sediment and
sludge samples in Austria, Environ. Pollut., 146 (2007) 543–547.
- X. Li, B.J. Brownawell, Quaternary ammonium compounds
in urban estuarine sediment environments—a class of
contaminants in need of increased attention? Environ. Sci.
Technol., 44 (2010) 7561–7568.
- P. Bassarab, D. Williams, J.R. Dean, E. Ludkin, J.J. Perry,
Determination of quaternary ammonium compounds in
seawater samples by solid-phase extraction and liquid
chromatography-mass spectrometry, J. Chromatogr. A, 1218
(2011) 673–677.
- A. Van De Voorde, C. Lorgeoux, M.C. Gromaire, G. Chebbo,
Analysis of quaternary ammonium compounds in urban
stormwater samples, Environ. Pollut., 164 (2012) 150–157.
- C. Zhang, F. Cui, G. Zeng, M. Jiang, Z. Yang, Z. Yu, M. Zhu,
L. Shen, Quaternary ammonium compounds (QACs): a review
on occurrence, fate and toxicity in the environment, Sci. Total
Environ., 518–519 (2015) 352–362.
- J. Pernak, K. Sobaszkiewicz, I. Mirska, Anti-microbial activities
of ionic liquids, Green Chem., 5 (2003) 52–56.
- S.P.M. Ventura, C.S. Marques, A.A. Rosatella, C.A.M. Afonso,
F. Gonçalves, J.A.P. Coutinho, Toxicity assessment of various
ionic liquid families towards Vibrio fischeri marine bacteria,
Ecotoxicol. Environ. Saf., 76 (2011) 162–168.
- G. Jing, Z. Zhou, J. Zhuo, Quantitative structure-activity
relationship (QSAR) study of toxicity of quaternary ammonium
compounds on Chlorella pyrenoidosa and Scenedesmus
quadricauda, Chemosphere., 86 (2012) 76–82.
- R.J. Bernot, M.A. Brueseke, M.A. Evans-White, G.A. Lamberti,
Acute and chronic toxicity of imidazolium-based ionic liquids
on Daphnia magna, Environ. Toxicol. Chem., 24 (2005) 87–92.
- M. Matzke, S. Stolte, J. Arning, U. Uebers, J. Filser, Ionic liquids
in soils: effects of different anion species of imidazolium
based ionic liquids on wheat (Triticum aestivum) as affected by
different clay minerals and clay concentrations, Ecotoxicology.,
18 (2009) 197–203.
- M. El-Harbawi, Toxicity measurement of imidazolium ionic
liquids using acute toxicity test, Procedia Chem., 9 (2014) 40–52.
- M.M. Bailey, M.B. Townsend, P.L. Jernigan, J. Sturdivant, W.L.
Hough-Troutman, J.F. Rasco, R.P. Swatloski, R.D. Rogers, R.D.
Hood, Developmental toxicity assessment of the ionic liquid
1-butyl-3-methylimidazolium chloride in CD-1 mice, Green
Chem., 10 (2008) 1213–1217.
- Y. Cheng, S.H. Wright, M.J. Hooth, I.G. Sipes, Characterization
of the disposition and toxicokinetics of n-butylpyridinium
chloride in male F-344 rats and female B6C3F1 mice and its
transport by organic cation transporter 2, Drug Metab. Dispos.,
37 (2009) 909–916.
- T.P.T. Pham, C.W. Cho, Y.S. Yun, Environmental fate and toxicity
of ionic liquids: a review, Water Res., 44 (2010) 352–372.
- N. Gal, D. Malferarri, S. Kolusheva, P. Galletti, E. Tagliavini,
R. Jelinek, Membrane interactions of ionic liquids: possible
determinants for biological activity and toxicity, Biochim.
Biophys. Acta, 12 (2012) 2967–2974.
- X.Y. Li, Y.R. Luo, M.X. Yun, J. Wang, J.J. Wang, Effects of
1-methyl-3-octylimidazolium bromide on the anti-oxidant
system of earthworm, Chemosphere., 78 (2009) 853–858.
- X.Y. Li, C.Q. Jing, W.L. Lei, J. Li, J.J. Wang, Apoptosis caused
by imidazolium-based ionic liquids in PC12 cells, Ecotoxicol.
Environ. Saf., 83 (2012) 102–107.
- Z. Du, L. Zhu, M. Dong, J. Wang, J. Wang, X. Hui, T. Liu, Y. Guo,
Oxidative stress and genotoxicity of the ionic liquid 1-octyl-3-methylimidazolium bromide in zebrafish (Danio rerio), Arch.
Environ. Contam. Toxicol., 67 (2014) 261–269.
- J. Ma, X. Dong, Q. Fang, J. Wang, X. Li, Toxicity of imidazoliumbased
ionic liquids on Physa acuta and the snail antioxidant
stress response, J. Biochem. Mol. Toxicol., 28 (2014) 69–75.
- D.R. Livingstone, Contaminant-stimulated reactive oxygen
species production and oxidative damage in aquatic organisms,
Mar. Pollut. Bull., 42 (2001) 656–666.
- V.I. Lushchak, Environmentally induced oxidative stress in
aquatic animals, Aquat. Toxicol., 101 (2011) 13–30.
- A. Valavanidis, T. Vlahogianni, M. Dassenakis, M. Scoullos,
Molecular biomarkers of oxidative stress in aquatic organisms
in relation to toxic environmental pollutants, Ecotox. Environ.
Saf., 64 (2006) 178–189.
- OECD, Test No. 202: Daphnia sp. Acute Immobilisation Test,
OECD Guidelines for the Testing of Chemicals, Section 2, OECD
Publishing, Paris, 2004.
- ASTM E1440—91(2012), Standard Guide for Acute Toxicity
Test with the Rotifer Brachionus, ASTM International, West
Conshohocken, PA, 2012.
- OECD, Test No. 201: Freshwater Alga and Cyanobacteria,
Growth Inhibition Test, OECD Guidelines for the Testing of
Chemicals, Section 2, OECD Publishing, Paris, 2011.
- OECD, Test No. 221: Lemna sp. Growth Inhibition Test, OECD
Guidelines for the Testing of Chemicals, Section 2, OECD
Publishing, Paris, 2006.
- L. Góth, A simple method for determination of serum catalase
activity and revision of reference range, Clin. Chim. Acta, 196
(1991) 143–151.
- H.P. Misra, I. Fridovich, The role of superoxide anion in the
autoxidation of epinephrine and a simple assay for superoxide
dismutase, J. Biol. Chem., 247 (1972) 3170–3175.
- W.H. Habig, M.J. Pabst, W.B. Jakoby, The first enzymatic
step in mercapturic acid formation, J. Biol. Chem., 249 (1974)
7130–7139.
- Commission of the European Communities, Technical
Guidance Document in Support of Commission Directive
93/67/EEC on Risk Assessment for Existing Substances. Part
II—Environmental risk assessment, Brussels, Office for Official
Publications of the European Communities, 1996.
- K.S. Egorova, V.P. Ananikov, Toxicity of ionic liquids: eco(cyto)
activity as complicated, but unavoidable parameter for taskspecific
optimization, ChemSusChem, 7 (2014) 336–360.
- M.E. Heckenbach, F.N. Romero, M.D. Green, R.U. Halden, Metaanalysis
of ionic liquid literature and toxicology, Chemosphere,
150 (2016) 266–274.
- S.P. Denyer, G.S.A.B. Stewart, Mechanisms of action of
disinfectants, Int. Biodeterior. Biodegrad., 41 (1998) 261–268.
- G. Nałȩcz-Jawecki, E. Grabińska-Sota, P. Narkiewicz, The
toxicity of cationic surfactants in four bioassays, Ecotoxicol.
Environ. Saf., 54 (2003) 87–91.
- V. Tsarpali, S. Dailianis, Toxicity of two imidazolium ionic
liquids, [bmim][BF4] and [omim][BF4], to standard aquatic test
organisms: role of acetone in the induced toxicity, Ecotoxicol.
Environ. Saf., 117 (2015) 62–71.
- L. Campanella, F. Cubadda, M.P. Sammartino, A. Saoncella, An
algal biosensor for the monitoring of water toxicity in estuarine
environments, Water Res., 35 (2001) 69–76.
- D. van Wijk, M.G. van den Bos, I. Garttener-Arends, M. Geurts,
J. Kamstra, P. Thomas, Bioavailability and detoxification
of cationics: I. Algal toxicity of alkyltrimethyl ammonium
salts in the presence of suspended sediment and humic acid,
Chemosphere, 75 (2009) 303–309.
- D.J. Couling, R.J. Bernot, K.M. Docherty, J.K. Dixon, E.J. Maginn,
Assessing the factors responsible for ionic liquid toxicity
to aquatic organisms via quantitative structure–property
relationship modeling, Green Chem., 8 (2006) 82–90.
- M.T. García, I. Ribosa, T. Guindulain, J. Sánchez-Leal, J. Vives-
Rego, Fate and effect of monoalkyl quaternary ammonium
surfactants in the aquatic environment, Environ. Pollut., 111
(2001) 169–175.
- M. Sandbacka, I. Christianson, B. Isomaa, The acute toxicity of
surfactants on fish cells, Daphnia magna and fish—a comparative
study, Toxicol. Vitr., 14 (2000) 61–68.
- C. Pretti, C. Chiappe, I. Baldetti, S. Brunini, G. Monni, L. Intorre,
Acute toxicity of ionic liquids for three freshwater organisms:
Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio,
Ecotoxicol. Environ. Saf., 72 (2009) 1170–1176.
- Y. Wang, Y. Zhang, X. Li, M. Sun, Z. Wei, Y. Wang, A. Gao, D.
Chen, X. Zhao, X. Feng, Exploring the effects of different types
of surfactants on zebrafish embryos and larvae, Sci. Rep., 5
(2015) 10107.
- M. Yu, S.H. Wang, Y.R. Luo, Y.W. Han, X.Y. Li, B.J. Zhang, J.J.
Wang, Effects of the 1-alkyl-3-methylimidazolium bromide
ionic liquids on the antioxidant defense system of Daphnia
magna, Ecotoxicol. Environ. Saf., 72 (2009) 1798–1804.
- P. Luis, A. Garea, A. Irabien, Quantitative structure-activity
relationships (QSARs) to estimate ionic liquids ecotoxicity EC50
(Vibrio fischeri), J. Mol. Liq., 152 (2010) 28–33.
- E. Richter, A. Wick, T.A. Ternes, A. Coors, Ecotoxicity of
climbazole, a fungicide contained in antidandruff shampoo,
Environ. Toxicol. Chem., 32 (2013) 2816–2825.
- E. Sancho, M.J. Villarroel, C. Fernández, E. Andreu, M.D.
Ferrando, Short-term exposure to sublethal tebuconazole
induces physiological impairment in male zebrafish (Danio
rerio), Ecotoxicol. Environ. Saf., 73 (2010) 370–376.
- C.M. Messina, C. Faggio, V.A. Laudicella, M. Sanfilippo, F.
Trischitta, A. Santulli, Effect of sodium dodecyl sulfate (SDS)
on stress response in the Mediterranean mussel (Mytilus
ggalloprovincialis): regulatory volume decrease (Rvd) and
modulation of biochemical markers related to oxidative stress,
Aquat. Toxicol., 157 (2014) 94–100.
- J. Wang, J. Wang, C. Xu, R. Liu, Y. Chen, Molecular mechanism
of catalase activity change under sodium dodecyl sulfateinduced
oxidative stress in the mouse primary hepatocytes,
J. Hazard. Mater., 307 (2016) 173–183.
- B. Zhang, X. Li, D. Chen, J. Wang, Effects of 1-octyl-3-
methylimidazolium bromide on the antioxidant system of
Lemna minor, Protoplasma., 250 (2013) 103–110.
- M.I. Viseu, E.P. Melo, T.I. Carvalho, R.F. Correia, S.M.B. Costa,
Unfolding kinetics of beta-lactoglobulin induced by surfactant
and denaturant: a stopped-flow/fluorescence study., Biophys.
J., 93 (2007) 3601–3612.
- D.E. Otzen, P. Sehgal, P. Westh, α-Lactalbumin is unfolded by
all classes of surfactants but by different mechanisms, J. Colloid
Interface Sci., 329 (2009) 273–283.
- A. Lee, S.K.Y. Tang, C.R. Mace, G.M. Whitesides, Denaturation
of proteins by SDS and by tetra-alkylammonium dodecyl
sulfates, Langmuir, 27 (2011) 11560–11574.
- D. Otzen, Protein-surfactant interactions: a tale of many states,
Biochim. Biophys. Acta, Proteins Proteomics, 1814 (2011)
562–591.