Toxicity mechanisms of ionic liquids

1. Matzke M, Arning J, Johannes R, Jastorff B, Stolte S. Design of inherently safer ionic liquids: toxicology and biodegradation In: Wasserscheid P, Stark A, editors. Handbook of green chemistry. Vol. 6: Ionic liquids. Weinheim: Wiley-VCH Verlag GmbH & Co.; 2010. p. 235-98.10.1002/9783527628698.hgc069Search in Google Scholar

2. Das RN, Roy K. Advances in QSPR/QSTR models of ionic liquids for the design of greener solvents of the future. Mol Divers 2013;17:151-96. doi: 10.1007/s11030-012-9413-ySearch in Google Scholar

3. Thuy Pham TP, Cho CW, Yun YS. Environmental fate and toxicity of ionic liquids: a review. Water Res 2010;44:352-72. doi: 10.1016/j.waters.2009.09.030Search in Google Scholar

4. Cvjetko Bubalo M, Radošević K, Radojčić Redovniković I, Halambek J, Gaurina Srček V. A brief overview of the potential environmental hazards of ionic liquids. Ecotoxicol Environ Saf 2014;99:1-12. doi: 10.1016/j.ecoenv.2013.10.019Search in Google Scholar

5. Egorova KS, Ananikov VP. Toxicity of ionic liquids: eco(cyto)activity as complicated, but unavoidable parameter for task-specific optimization. ChemSusChem 2014;7:336-60. doi: 10.1002/cssc.201300459Search in Google Scholar

6. Kudłak B, Owczarek K, Namieśnik J. Selected issues related to the toxicity of ionic liquids and deep eutectic solvents-a review. Environ Sci Pollut Res 2015;22:11975-92. doi: 10.1007/s11356-015-4794-ySearch in Google Scholar

7. Costa SPF, Azevedo AMO, Pinto PCAG, Saraiva MLMFS. Environmental impact of ionic liquids: an overview of recent (eco)toxicological and (bio)degradability literature. ChemSusChem 2017;10:2321-47. doi:10.1002/ cssc.201700261Search in Google Scholar

8. Egorova KS, Gordeev EG, Ananikov VP. Biological activity of ionic liquids and their application in pharmaceutics and medicine. Chem Rev 2017;117:7132-89. doi: 10.1021/acs. chemrev.6b00562Search in Google Scholar

9. Cvjetko Bubalo M, Radošević K, Radojčić Redovniković I, Halambek J, Vorkapić-Furač J, Gaurina Srček V. Ionske kapljevine - razvoj i izazovi industrijske primjene [Ionic liquids - development and challenges in industrial application, in Croatian]. Kem ind 2014;63:163-71. doi: 10.15255/ KUI.2013.003Search in Google Scholar

10. Abu-Eishah IS. Ionic liquids recycling for reuse. In: Handy ST, editor. Ionic liquids - classes and properties. Rijeka: InTech; 2011. p. 239-72.Search in Google Scholar

11. Fatemi MH, Izadiyan P. Cytotoxicity estimation of ionic liquids based on their effective structural features. Chemosphere 2011;84:553-63. doi: 10.1016/j. chemosphere.2011.04.021Search in Google Scholar

12. Ranke J, Mölter K, Stock F, Bottin-Weber U, Poczobutt J, Hoffmann J, Ondruschka B, Filser J, Jastorff B. Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays. Ecotoxicol Environ Saf 2004;58:396-404. doi: 10.1016/S0147-6513(03)00105-2Search in Google Scholar

13. Cvjetko M, Radošević K, Tomica A, Slivac I, Vorkapić-Furač J, Gaurina Srček V. Cytotoxic effects of imidazolium ionic liquids on fish and human cell lines. Arh Hig Rada Toksikol 2012;63:15-9. doi: 10.2478/10004-1254-63-2012-2132Search in Google Scholar

14. Radošević K, Cvjetko M, Kopjar N, Novak R, Dumić J, Gaurina Srček V. In vitro cytotoxicity assessment of imidazolium ionic liquids: Biological effects in fish Channel Catfish Ovary (CCO) cell line. Ecotoxicol Environ Saf 2013;92:112-8. doi: 10.1016/j.ecoenv.2013.03.002Search in Google Scholar

15. Swatloski RP, Holbrey JD, Memon SB, Caldwell GA, Caldwell KA, Rogers RD. Using Caenorhabditis elegans to probe toxicity of 1-alkyl-3-methylimizolium chloride based ionic liquids. Chem Commun 2004;6:668-9. doi: 10.1039/ b316491hSearch in Google Scholar

16. Docherty KM, Kulpa CFJ. Toxicity and antimicrobial activity of imidazolium and pyridinium ionic liquids. Green Chem 2005;7:185-9. doi: 10.1039/B419172BSearch in Google Scholar

17. Kulacki KJ, Lamberti GA. Toxicity of imidazolium ionic liquids to freshwater algae. Green Chem 2008;10:104-10. doi: 10.1039/B709289JSearch in Google Scholar

18. Couling DJ, Bernot RJ, Docherty KM, Dixon JK, Maginn EJ. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem 2006;8:82-90. doi: 10.1039/B511333DSearch in Google Scholar

19. Petkovic M, Hartmann DO, Adamová G, Seddon KR, Rebelo LPN, Silva Pereira C. Unravelling the mechanism of toxicity of alkyltributylphosphonium chlorides in Aspergillus nidulans conidia. New J Chem 2012;36:56-63. doi: 10.1039/ C1NJ20470JSearch in Google Scholar

20. Cornmell RJ, Winder CL, Tiddy GJT, Goodacre R, Stephens G. Accumulation of ionic liquids in Escherichia coli cells. Green Chem 2008;10:836-41. doi: 10.1039/B807214KSearch in Google Scholar

21. Arning J, Stolte S, Boschen A, Stock F, Pitner WR, Welz- Biermann U, Jastorff B, Ranke J. Qualitative and quantitative structure activity relationships for the inhibitory effects of cationic head groups, functionalised side chains and anions of ionic liquids on acetylcholinesterase. Green Chem 2008;10:47-58. doi: 10.1039/B712109ASearch in Google Scholar

22. Dong X, Fan YC, Zhang H, Zhong YY, Yang Y, Miao J, Hua SF. Inhibitory effects of ionic liquids on the lactic dehydrogenase activity. Int J Biol Macromol 2016;86:155-61. doi: 10.1016/j.ijbiomac.2016.01.059Search in Google Scholar

23. Fan YC, Dong X, Li XJ, Zhong YY, Kong JC, Hua SF, Miao J, Li Y. Spectroscopic studies on the inhibitory effects of ionic liquids on lipase activity. Spectrochim Acta A Mol Biomol Spectrosc 2016;159:128-33. doi: 10.1016/j. saa.2016.01.047Search in Google Scholar

24. Latała A, Stepnowski P, Nędzi M, Mrozik W. Marine toxicity assessment of imidazolium ionic liquids: Acute effect on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. Aquat Toxicol 2005;73:91-8. doi: 10.1016/j. aquatox.2005.03.008Search in Google Scholar

25. Kumar M, Trivedi N, Reddy CR, Jha B. Toxic effects of imidazolium ionic liquids on the green seaweed Ulva lactuca: Oxidative stress and DNA damage. Chem Res Toxicol 2011;24:1882-90. doi: 10.1021/tx200228cSearch in Google Scholar

26. Cvjetko Bubalo M, Hanousek K, Radošević K, Gaurina Srček V, Jakovljević T, Radojčić Redovniković I. Imidiazolium based ionic liquids: Effects of different anions and alkyl chains lengths on the barley seedlings. Ecotoxicol Environ Saf 2014;101:116-23. doi: 10.1016/j.ecoenv.2013.12.022Search in Google Scholar

27. Jing CQ, Li XY, Zhang JH, Wang JJ. Responses of the antioxidant system in QGY-7701 cells to the cytotoxicity and apoptosis induced by 1-octyl-3-methylimidazolium chloride. J Biochem Mol Toxic 2013;27:330-6. doi: 10.1002/jbt.21495Search in Google Scholar

28. Žlender V. Apoptoza-programirana smrt stanice [Apoptosis - programmed cell death, in Croatian]. Arh Hig Rada Toksikol 2003;54:267-74.Search in Google Scholar

29. Li XY, Jing CQ, Zang XY, Yang S, Wang JJ. Toxic cytological alteration and mitochondrial dysfunction in PC12 cells induced by 1-octyl-3-methylimidazolium chloride. Toxicol in Vitro 2012;26:1087-92. doi: 10.1016/j.tiv.2012.07.006Search in Google Scholar

30. Paiva A, Craveiro R, Aroso I, Martins M, Reis RL, Duarte ARC. Natural deep eutectic solvents-solvents for the 21st century. ACS Sustainable Chem Eng 2014;2:1063-71. doi: 10.1021/sc500096jSearch in Google Scholar

31. Das NR, Roy K. Predictive modeling studies for the ecotoxicity of ionic liquids towards the green algae Scenedesmus vacuolatus. Chemosphere 2014;104:170-76. doi: 10.1016/j.chemosphere.2013.11.002Search in Google Scholar

32. Cvjetko Bubalo M, Radošević K, Gaurina Srček V, Das RN, Popelier P, Roy K. Cytotoxicity towards CCO cells of imidazolium ionic liquids with functionalized side chains. Predictive modeling of chemical toxicity using regression and classification based approaches. Ecotoxicol Environ Saf 2015;112:22-8. doi: 10.1016/j.ecoenv.2014.10.029Search in Google Scholar

33. Hou XD, Liu QP, Smith TJ, Li N, Zong MH. Evaluation of toxicity and biodegradability of cholinium amino acids ionic liquids. PLoS One 2013;8:e59145. doi: 10.1371/journal. pone.0059145Search in Google Scholar

34. Radošević K, Železnjak J, Cvjetko Bubalo M, Radojčić Redovniković I, Slivac I, Gaurina Srček V. Comparative in vitro study of cholinium-based ionic liquids and deep eutectic solvents toward fish cell line. Ecotoxicol Environ Saf 2016;131:30-6. doi: 10.1016/j.ecoenv.2016.05.005Search in Google Scholar