In silico modelling for predicting the cationic hydrophobicity and cytotoxicity of ionic liquids towards the Leukemia rat cell line, Vibrio fischeri and Scenedesmus vacuolatus based on molecular interaction potentials of ions

SAR and QSAR in Environmental Research

Volumn 24, Issue 10, 2013, Pages 863-882

  Cho, C W ^a   Ranke, J ^a   Arning, J ^a   Thoming J ^a   Preiss, U ^b   Jungnickel, C ^c   Diedenhofen, M ^d   Krossing, I ^e   Stolte, S ^a  

^a UNIVERSITY OF BREMEN   (Germany)

^b RUHR UNIVERSITY BOCHUM   (Germany)

^c GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

^d COSMOlogic GmbH and Co KG ^*  (Germany)

^e UNIVERSITY OF FREIBURG   (Germany)

Author keywords

COSMO RS; density functional theory (DFT); ionic liquids; linear free energy relationship (LFER); quantitative structure activity relationship (QSAR); toxicity prediction

Indexed keywords

ALGAE; BACTERIA; CELL CULTURE; COMPUTATIONAL CHEMISTRY; CYTOTOXICITY; DESIGN FOR TESTABILITY; DISEASES; FORECASTING; FREE ENERGY; HYDROGEN; HYDROGEN BONDS; HYDROPHOBICITY; IONIC LIQUIDS; POSITIVE IONS; STATISTICAL TESTS;

COSMO-RS; DENSITY FUNCTIONAL THEORY; DENSITY-FUNCTIONAL-THEORY; LINEAR FREE ENERGY RELATIONSHIP; LINEAR FREE ENERGY RELATIONSHIPS; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; STANDARD ERRORS; TOXICITY PREDICTIONS; VIBRIO FISCHERI;

DENSITY FUNCTIONAL THEORY;

BACTERIA (MICROORGANISMS); CHLOROPHYTA; RATTUS; SCENEDESMUS; SCENEDESMUS VACUOLATUS; VIBRIO FISCHERI;

IONIC LIQUID;

ALIIVIBRIO FISCHERI; ANIMAL; ARTICLE; BONE MARROW CELL; CELL SURVIVAL; CHEMICAL PHENOMENA; CHEMISTRY; DRUG EFFECT; RAT; SCENEDESMUS; STATISTICAL MODEL; TUMOR CELL LINE;

ALIIVIBRIO FISCHERI; ANIMALS; CELL LINE, TUMOR; CELL SURVIVAL; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; IONIC LIQUIDS; MODELS, STATISTICAL; MYELOID CELLS; RATS; SCENEDESMUS;

EID: 84888014978     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2013.821092     Document Type: Article

References (76)

1. Plechkova, N.V. and Seddon, K.R. 2008. Applications of ionic liquids in the chemical industry. Chem. Soc. Rev., 37: 123 - 150.
2. Cho, C.-W., Preiss, U., Jungnickel, C., Stolte, S., Arning, J., Ranke, J., Klamt, A., Krossing, I. and Thöming, J. 2011. Ionic liquids: Predictions of physicochemical properties with experimental and/or DFT-calculated LFER parameters to understand molecular interactions in solution. J. Phys. Chem. B, 115: 6040 - 6050.
3. Gardas, R.L. and Coutinho, J.A.P. 2009. Group contribution methods for the prediction of thermophysical and transport properties of ionic liquids. Aiche J., 55: 1274 - 1290.
4. R. Kato and J. Gmehling, Systems with ionic liquids: Measurement of VLE and gamma-infinite data and prediction of their thermodynamic behavior using original UNIFAC, mod. UNIFAC(Do) and COSMO-RS(Ol), J. Chem. Therm. 37 (2005), pp. 603-619.
5. Slattery, J.M., Daguenet, C., Dyson, P.J., Schubert, T.J.S. and Krossing, I. 2007. How to predict the physical properties of ionic liquids: A volume-based approach. Angew. Chem. Int. Edit, 46: 5384 - 5388.
6. Sprunger, L., Clark, M., Acree, W.E. Jr. and Abraham, M.H. 2007. Characterization of room-temperature ionic liquids by the Abraham model with cation-specific and anion-specific equation coefficients. J. Chem. Inf. Model., 47: 1123 - 112.
7. Ranke, J., Mölter, K., Stock, F., Bottin-Weber, U., Poczobutt, J., Hoffmann, J., Ondruschka, B., Filser, J. and Jastorff, B. 2007. Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotox. Environ. Safe., 58: 430 - 438.
8. Stolte, S., Matzke, M., Arning, J., Böschen, A., Pitner, W.R., Welz-Biermann, U. and Jastorff, B. 2007. Effects of different head groups and functionalised side chains on the aquatic toxicity of ionic liquids. Green Chem., 9: 1170 - 1179.
9. Docherty, K.M. and Kulpa, C.F. Jr. 2005. Toxicity and antimicrobial effects of imidazolium and pyridinium ionic liquids. Green Chem., 7: 185 - 189.
10. Samori, C., Pasteris, A., Galletti, P. and Tagliavini, E. 2007. Acute toxicity of oxygenated and nonoxygenated imidazolium. Environ. Toxicol. Chem., 26: 2379 - 2382.
11. Romero, A., Santos, A., Tojo, J. and Rodríguez, A. 2008. Toxicity and biodegradability of imidazolium ionic liquids. J. Hazard. Mater., 151: 268 - 273.
12. Cho, C.-W., Pham, T.P.T., Jeon, Y.-C., Vijayaragvahan, K., Choe, W.S. and Yun, Y.-S. 2007. Toxicity of imidazolium salt with anion bromide to a phytoplankton Selenastrum capricornutum: Effect of alkyl-chain length. Chemosphere, 69: 1003 - 1007.
13. Cho, C.-W., Pham, T.P.T., Jeon, Y.-C. and Yun, Y.-S. 2008. Influence of anions on the toxic effect of ionic liquids to a phytoplankton Selenastrum capricornutum. Green Chem., 10: 67 - 72.
14. Cho, C.-W., Pham, T.P.T., Jeon, Y.-C., Vijayaragvahan, K. and Yun, Y.-S. 2008. The ecotoxicity of ionic liquids and traditional organic solvents on microalga Selenastrum capricornutum. Ecotox. Environ. Safe., 71: 166 - 171.
15. Latała, A., Stepnowski, P., Ne{ogonek}dzi, M. and Mrozik, W. 2005. Marine toxicity assessment of imidazolium ionic liquids: acute effects on the Baltic algae Oocystis submarina and Cyclotella meneghiniana. Aqua. Toxicol., 73: 91 - 98.
16. Kulacki, K.J. and Lamberti, G.A. 2008. Toxicity of imidazolium ionic liquids to freshwater algae. Green Chem., 10: 104 - 110.
17. Pham, T.P.T., Cho, C.-W., Min, J. and Yun, Y.-S. 2008. Alkyl-chain length effects of imidazolium and pyridinium ionic liquids on photosynthetic response of Pseudokirchneriella subcapitata. J. Biosci. Bioeng., 105: 425 - 428.
18. Pham, T.P.T., Cho, C.-W., Vijayaghavan, K., Min, J. and Yun, Y.-S. 2008. Effect of imidazolium-based ionic liquids on the photosynthetic activity and growth rate of Selenastrum capricornutum. Environ. Toxicol. Chem., 27: 1583 - 1589.
19. Pretti, C., Chiappe, C., Baldetti, I., Brunini, S., Monni, G. and Intorre, L. 2009. Acute toxicity of ionic liquids for three freshwater organisms: Pseudokirchneriella subcapitata, Daphnia magna and Danio rerio. Ecotox. Environ. Safe., 72: 1170 - 1176.
20. Latała, A., Ne{ogonek}dzi, M. and Stepnowski, P. 2010. Toxicity of imidazolium ionic liquids towards algae. Influence of salinity variations. Green Chem., 12: 60 - 64.
21. Stepnowski, P., Skladanowski, A.C., Ludwiczak, A. and Laczyńska, E. 2004. Evaluating the cytotoxicity of ionic liquids using human cell line HeLa. Hum. Exp. Toxicol., 23: 513 - 517.
22. Wang, X., Andre Ohlin, C.A., Lu, Q., Fei, Z., Hu, J. and Dyson, P.J. 2007. Cytotoxicity of ionic liquids and precursor compounds towards human cell line HeLa. Green Chem., 9: 1191 - 1197.
23. Frade, R.F.M., Matias, A., Branco, L.C., Afonso, C.A.M. and Duarte, C.M.M. 2007. Effect of ionic liquids on human colon carcinoma HT-29 and Caco-2cell lines. Green Chem., 9: 873 - 877.
24. Garcia-Lorenzo, A., Tojo, E., Tojo, J., Teijeira, M., Rodriguez-Berrocal, F.J., Gonzalez, M.P. and Martinez-Zorzano, V.S. 2008. Cytotoxicity of selected imidazolium-derived ionic liquids in the human Caco-2 cell line. Sub-structural toxicological interpretation through a QSAR study. Green Chem., 10: 508 - 516.
25. Bernot, R.J., Brueseke, M.A., Evans-White, M.A. and Lamberti, G.A. 2005. Acute and chronic toxicity of imidazolium-based ionic liquids on Daphnia magna. Environ. Toxicol. Chem., 24: 87 - 92.
26. Ranke, J., Mueller, A., Bottin-Weber, U., Stock, F., Stolte, S., Arning, J., Störmann, R. and Jastorff, B. 2007. Lipophilicity parameters for ionic liquid cations and their correlation to in vitro cytotoxicity. Ecotox. Environ. Safe., 67: 430 - 438.
27. Couling, C.J., Bernot, R.J., Docherty, K.M., Dixon, J.K. and Maginn, E.J. 2006. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling. Green Chem., 8: 82 - 90.
28. Petkovic, M., Seddon, K.R., Rebelo, L.P.N. and Pereira, C.S. 2011. Ionic liquids a pathway to environmental acceptability. Chem. Soc. Rev., 40: 1383 - 1403.
29. Ranke, J., Stolte, S., Störmann, R., Arning, J. and Jastorff, B. 2007. Design of sustainable chemical products - the example of ionic liquids. Chem. Rev., 107: 2183 - 2206.
30. Pham, T.P.T., Cho, C.-W. and Yun, Y.-S. 2010. Environmental fate and toxicity of ionic liquids: A review. Water Res., 44: 352 - 372.
31. Zhao, D.B., Liao, Y.C. and Zhang, Z.D. 2007. Toxicity of ionic liquids. Clean-Soil Air Water, 35: 42 - 48.
32. Boethling, R.S., Sommer, E. and DiFiore, D. 2007. Designing small molecules for biodegradability. Chem. Rev., 107: 2207 - 2227.
33. Coleman, D. and Gathergood, N. 2010. Biodegradation studies of ionic liquids. Chem. Soc. Rev., 39: 600 - 637.
34. Stolte, S., Steudte, S., Igartua, A. and Stepnowski, P. 2011. The biodegradation of ionic liquids-the view from a chemical structure perspective. Curr. Org. Chem., 15: 1946 - 1973.
35. Luis, P., Ortiz, I., Aldaco, R. and Irabien, A. 2007. A novel group contribution method in the development of a QSAR for predicting the toxicity (Vibrio fischeri EC50) of ionic liquids. Ecotox. Environ. Safe., 67: 423 - 429.
36. Luis, P., Garea, A. and Irabien, A. 2010. Quantitative structure-activity relationship (QSARs) to estimate ionic liquids ecotoxicity EC50 (Vibrio fischeri). J. Mol. Liq., 152: 28 - 33.
37. Torrecilla, J.S., Garcia, J., Rojo, E. and Rodríguez, F. 2009. Estimation of toxicity of ionic liquids in Leukemia Rate Cell Line and Acetylcholinesterase enzyme by principal component analysis, neural networks and multiple linear regressions. J. Hazard. Mat., 164: 182 - 194.
38. Torrecilla, J.S., Ralomar, J., Lemus, J. and Rodríguez, F. 2010. A quantum-chemical-based guide to analyze/quantify the cytotoxicity of ionic liquids. Green Chem., 12: 123 - 134.
39. Fatemi, M.H. and Izadiyan, P. 2011. Cytotoxicity estimation of ionic liquids based on their effective structural features. Chemosphere, 84: 553 - 563.
40. Alvarez-Guerra, M. and Irabien, A. 2011. Design of ionic liquids: an ecotoxicity (Vibrio fischeri) discrimination approach. Green Chem., 13: 1507 - 1516.
41. Centre for Environmental Research and Sustainable Technology (UFT). Available at http://chemuftuni-bremende/il-eco/. Accessed 01 Nov 2011.
42. Luis, P., Afonso, C.A.M., Coelhoso, I.M., Creso, J. and Irabien, A. 2008. Proceedings of the 23rd European symposium on Applied Thermodynamics Congress, France: Cannes.
43. Abraham, M.H., Ibrahim, A. and Zissimos, A.M. 1037. Determination of sets of solute descriptors from chromatographic measurements. J. Chromatogr. A, 2004: 29 - 47.
44. Abraham, M.H., Chadha, H.S., Whiting, G.S. and Mitchell, R.C. 1994. Hydrogen bonding. 32. An analysis of water-octanol and water alkane partitioning and the delta log P parameters of seiler. J. Pharm. Sci., 83: 1085 - 1100.
45. Sprunger, L., Proctor, A., Acree, W.E. Jr. and Abraham, M.H. 2007. Characterization of the sorption of gaseous and organic solutes onto polydimethyl siloxane solid-phase microextraction surfaces using the Abraham model. J. Chromatog. A, 1175: 162 - 173.
46. Gunatilleka, A.D. and Poole, C.F. 1999. Models for estimating the non-specific aquatic toxicity of organic compounds. Anal. Commun., 36: 235 - 242.
47. Hoover, H.R., Acree, W.E. Jr. and Abraham, M.H. 2005. Chemical toxicity correlations for several protozoas, bacteria, and water fleas based on the Abraham solvation parameters model. Chem. Res. Toxicol., 18: 1497 - 1505.
48. Sprunger, L.M., Proctor, A., Acree, W.E. Jr. and Abraham, M.H. 2008. LFER correlations for room temperature ionic liquids: Separation of equation coefficients into individual cation-specific and anion-specific contributions. Fluid Phase Equilibr., 265: 104 - 111.
49. Klamt, A. and Schüürmann, G. 1993. COSMO: A new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkin. Trans., 2: 799 - 805.
50. O'Boyle, N.M., Banck, M., James, C.A., Morley, C., Vandermeersch, T. and Hutshison, G.R. 2011. Open Bable: An open chemical toolbox. J. Cheminformatics, 3: 33
51. Cho, C.-W., Jungnickel, C., Stolte, S., Preiss, U., Arning, J., Ranke, J., Krossing, I. and Thöming, J. 2012. Determination of LFER descriptors of 30 cations of ionic liquids - progress in understanding their molecular interaction potentials. ChemPhysChem, 13: 780 - 787.
52. Zissimos, A.M., Abraham, M.H., Klamt, A., Eckert, F. and Wood, J. 2002. A comparison between the two general sets of linear free energy descriptors of Abraham and Klamt. J. Chem. Inf. Comput. Sci., 42: 1320 - 1331.
53. Klamt, A., Eckert, F. and Hornig, M. 2001. COSMO-RS: A novel view to physiological solvation and partition questions. J. Comput. Aid. Mol. Des., 15: 355 - 365.
54. TURBOMOLE V510, (2008) a development of University of Karlsruhe, 1989-2007, TURBOMOLE GmbH, since 2007. Available at http://wwwturbomolecom.
55. Perdew, J.P. 1986. Density-functional approximation for the correlation energy of the inhomogeneous electron gas. Phys. Rev. B, 33: 8822 - 8824.
56. Deglmann, P., Furche, F. and Ahlrichs, R. 2002. An efficient implementation of second analytical derivatives for density functional methods. Chem. Phys. Lett., 362: 511 - 518.
57. Deglmann, P. and Furche, F. 2002. Efficient characterization of stationary points on potential ennergy surfaces. J. Chem. Phys., 117: 9535 - 9538.
58. Schäfer, A., Huber, C. and Ahlrichs, R. 1994. Fully optimized contracted Gaussian basis sets of triple zeta valence quality for atoms Li to Kr. J. Chem. Phys., 100: 5829 - 5835.
59. Stepnowski, P. and Storoniak, P. 2005. Lipophilicity and metabolic route prediction of imidazolium ionic liquids. Environ. Sci. Poll. Res., 12: 199 - 204.
60. Eadsforth, C.V. and Moser, P. 1983. Assessment of reverse phase chromatographic methods for determining partition coefficient. Chemosphere, 12: 1459 - 1475.
61. Klein, W., Kördel, W., Weiss, M. and Poremski, H.J. 1988. Updating of the OECD test guideline 107 partitioning-coefficient N-Octanol Water - OECD laboratory intercomparison test on the HPLC method. Chemosphere, 17: 361 - 386.
62. OECD guidelines for the test of chemicals No 117 - Partitioning Coefficient (n-octanol/water) High Performance Liquid Chromatography (HPLC) Method (2004).
63. Stolte, S., Arning, J., Bottin-Weber, U., Müller, A., Pitner, W.R., Welz-Biermann, U., Jastorff, B. and Ranke, J. 2007. Effects of different head groups and functionalised side chains on the cytotoxicity of ionic liquids. Green Chem., 9: 760 - 767.
64. Ranke, J., Othman, A., Fan, P. and Müller, A.B. 2009. Explaining ionic liquid water solubility in terms of cation and anion hydrophobicity. J. Mol. Sci., 10: 1271 - 1289.
65. Arning, J., Stolte, S., Böschen, A., Stock, F., Pitner, W.-R., Welz-Biermann, U., Jastorff, B. and Ranke, J. 2008. 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., 10: 47 - 58.
66. J. Ranke, K Mölter, F. Stock, U. Bottin-Weber, J Poczbutt, J. Hoffmann, B. Ondruschka, J. Filser, and B. Jastorff, Biological effects of imidazolium ionic liquids with varying chain lengths in acute Vibrio fischeri and WST-1 cell viability assays, Ecotox. Environ. Safe. 58 (2004), pp. 396-404.
67. Dearden, J.C., Cronin, M.T.D. and Kaiser, K.L.E. 2009. How to develop a quantative structure-activity or structure-property relationship (QSAR/QSPR). SAR QSAR Environ. Res., 20: 241 - 266.
68. Esher, B.I., Eggen, R.L., Schreiber, U., Schreiber, Z., Vye, E., Wisner, B. and Schwarzenbach, R.P. 2002. Baseline toxicity (narcosis) or organic chemicals determined by in vitro membrane potential measurements in energy-transducing membranes. Environ. Sci. Technol., 36: 1971 - 1979.
69. Könemann, H. 1981. Quantitative structure-activity relationship in fish toxicity studies Part 1: Relationship for 50 industrial pollutants. Toxicology, 19: 209 - 221.
70. P. Mayer and F. Reichenberg Can highly hydrophobic organic substances cause aquatic baseline toxicity and can they contribute to mixture toxicity? Environ. Toxicol. Chem. 25 (2006), pp. 2639-2644.
71. Łuczak, J., Jungnickel, C., Ła{ogonek}cka, I. and Stolte, S. 2010. Antimicrobial and surface activity of 1-alkyl-3-methylimidazolium derivatives. Green Chem., 12: 593 - 601.
72. Łuczak, J., Jungnickel, C., Joskowska, M., Thöming, J. and Hupka, J. 2009. Thermodynamics of micellization of imidazolium ionic liquids in aqueous solutions. J. Colloid. Interf. Sci., 336: 111 - 116.
73. Dong, B., Zhao, X., Zheng, L., Zhang, J., Li, N. and Inoue, T. 2008. Aggregation behavior of long-chain imidazolium ionic liquids in aqueous solution: Micellization and characterization of micelle microenvironment. Colloids Surf. A: Physicochem. Eng. Aspects, 317: 666 - 672.
74. Matzke, M., Stolte, S., Böschen, A. and Filser, J. 2008. Mixture effects and predictability of combination effects of imidazolium based ionic liquids as well as imidazolium based ionic liquids and cadmium on terrestrial plants (Triticum aestivum) and limnic green algae (Scenedesmus vacuolatus). Green Chem., 10: 784 - 792.
75. Zhang, J., Liu, S.S., Dou, R.N., Liu, H.L. and Zhang, J. 2011. Evaluation on the toxicity of ionic liquid mixture with antagonism and synergism to Vibrio qinghaiensis sp. -Q67. Chemosphere, 82: 1024 - 1029.
76. Anastas, P.T. and Warner, N.C. 1988. Green Chemistry: Theory and Practice, New York, NY: Oxford University Press.