Predicting toxicity of ionic liquids in acetylcholinesterase enzyme by the quantitative structure-activity relationship method using topological indexes

Journal of Chemical and Engineering Data

Volumn 57, Issue 8, 2012, Pages 2252-2257

  Yan, Fangyou ^a   Xia, Shuqian ^a   Wang, Qiang ^b   Ma, Peisheng ^a  

^a TIANJIN UNIVERSITY   (China)

^b TIANJIN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINESTERASE; ATOM POSITIONS; AVERAGE ABSOLUTE ERROR; IMIDAZOLIUM; MULTIPLE LINEAR REGRESSION METHOD; PYRIDINIUM; PYRROLIDINIUM; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP METHODS; REGRESSION COEFFICIENT; TOPOLOGICAL INDEX;

AMMONIUM COMPOUNDS; CHEMICAL BONDS; ELECTRONEGATIVITY; ENZYMES; HYDROGEN; IONIC LIQUIDS; LINEAR REGRESSION; POSITIVE IONS; TOPOLOGY; TOXICITY;

ATOMS;

EID: 84864918220     PISSN: 00219568     EISSN: 15205134     Source Type: Journal    
DOI: 10.1021/je3002046     Document Type: Article

References (35)

1. Ito, S.; Zakeeruddin, S. M.; Comte, P.; Liska, P.; Kuang, D.; Gratzel, M. Bifacial dye-sensitized solar cells based on an ionic liquid electrolyte Nat. Photon. 2008, 2, 693-698
2. Kim, S. Y.; Kim, S.; Park, M. J. Enhanced proton transport in nanostructured polymer electrolyte/ionic liquid membranes under water-free conditions Nat. Commun. 2010, 1, 88
3. Lu, W.; Fadeev, A. G.; Qi, B.; Smela, E.; Mattes, B. R.; Ding, J.; Spinks, G. M.; Mazurkiewicz, J.; Zhou, D.; Wallace, G. G.; MacFarlane, D. R.; Forsyth, S. A.; Forsyth, M. Use of Ionic Liquids for φ-Conjugated Polymer Electrochemical Devices Science 2002, 297, 983-987 (Pubitemid 34856026)
4. Pârvulescu, V. I.; Hardacre, C. Catalysis in Ionic Liquids Chem. Rev. 2007, 107, 2615-2665 (Pubitemid 47029102)
5. Vygodskii, Y. S.; Sapozhnikov, D. A.; Shaplov, A. S.; Lozinskaya, E. I.; Ignat'ev, N. V.; Schulte, M.; Vlasov, P. S.; Malyshkina, I. A. New ionic liquids with hydrolytically stable anions as alternatives to hexafluorophosphate and tetrafluoroborate salts in the free radical polymerization and preparation of ion-conducting composites Polym. J. 2011, 43, 126-135
6. Zhao, H.; Holladay, J. E.; Brown, H.; Zhang, Z. C. Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural Science 2007, 316, 1597-1600 (Pubitemid 46982028)
7. Ogoshi, T.; Onodera, T.; Yamagishi, T.-A.; Nakamoto, Y.; Kagata, A.; Matsumi, N.; Aoi, K. Transparent ionic liquid-phenol resin hybrids with high ionic conductivity Polym. J. 2011, 43, 421-424
8. Cooper, E. R.; Andrews, C. D.; Wheatley, P. S.; Webb, P. B.; Wormald, P.; Morris, R. E. Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues Nature 2004, 430, 1012-1016 (Pubitemid 39128383)
9. Matsumi, N.; Nakamura, Y.; Aoi, K.; Watanabe, T.; Mizumo, T.; Ohno, H. Enhanced Ionic Conduction in Organoboron Ion Gels Facilely Designed via Condensation of Cellulose with Boric Acids in Ionic Liquids Polym. J. 2009, 41, 437-441
10. Rogers, R. D.; Seddon, K. R. Ionic Liquids - Solvents of the Future? Science 2003, 302, 792-793 (Pubitemid 37339605)
11. Thuy Pham, T. P.; Cho, C.-W.; Yun, Y.-S. Environmental fate and toxicity of ionic liquids: A review Water Res. 2010, 44, 352-372
12. Arning, J.; Stolte, S.; Boschen, A.; Stock, F.; Pitner, W.-R.; 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
13. Jastorff, B.; Molter, K.; Behrend, P.; Bottin-Weber, U.; Filser, J.; Heimers, A.; Ondruschka, B.; Ranke, J.; Schaefer, M.; Schroder, H.; Stark, A.; Stepnowski, P.; Stock, F.; Stormann, R.; Stolte, S.; Welz-Biermann, U.; Ziegert, S.; Thoming, J. Progress in evaluation of risk potential of ionic liquids-basis for an eco-design of sustainable products Green Chem. 2005, 7, 362-372 (Pubitemid 40745568)
14. Matzke, M.; Stolte, S.; Thiele, K.; Juffernholz, T.; Arning, J. A. R.; Ranke, J.; Welz-Biermann, U.; Jastorff, B. The influence of anion species on the toxicity of 1-alkyl-3-methylimidazolium ionic liquids observed in an (eco)toxicological test battery Green Chem. 2007, 9, 1198-1207
15. Ranke, J.; Stolte, S.; Störmann, R.; Arning, J.; Jastorff, B. Design of Sustainable Chemical ProductsThe Example of Ionic Liquids Chem. Rev. 2007, 107, 2183-2206 (Pubitemid 47029092)
16. Couling, D. J.; Bernot, R. J.; Docherty, K. M.; Dixon, J. K.; Maginn, E. J. Assessing the factors responsible for ionic liquid toxicity to aquatic organisms via quantitative structure-property relationship modeling Green Chem. 2006, 8, 82-90 (Pubitemid 43485029)
17. Luis, P.; Ortiz, I.; Aldaco, R.; Irabien, A. A novel group contribution method in the development of a QSAR for predicting the toxicity (Vibrio fischeri EC50) of ionic liquids Ecotoxicol. Environ. Saf. 2007, 67, 423-429 (Pubitemid 46836729)
18. Luis, P.; Garea, A.; Irabien, A. Quantitative structure-activity relationships (QSARs) to estimate ionic liquids ecotoxicity EC50 (Vibrio fischeri) J. Mol. Liq. 2010, 152, 28-33
19. García-Lorenzo, A.; Tojo, E.; Tojo, J.; Teijeira, M.; Rodriguez-Berrocal, F. J.; Gonzalez, M. P.; Martinez-Zorzano, V. S. Cytotoxicity of selected imidazolium-derived ionic liquids in the human Caco-2 cell line. Sub-structural toxicological interpretation through a QSAR study Green Chem. 2008, 10, 508-516 (Pubitemid 351637551)
20. Torrecilla, J. S.; Palomar, J.; Lemus, J.; Rodriguez, F. A quantum-chemical-based guide to analyze/quantify the cytotoxicity of ionic liquids Green Chem. 2010, 12, 123-134
21. Lacrama, A.-M.; Putz, M.; Ostafe, V. A Spectral-SAR Model for the Anionic-Cationic Interaction in Ionic Liquids: Application to Vibrio fischeri Ecotoxicity Int. J. Mol. Sci. 2007, 8, 842-863 (Pubitemid 47360760)
22. Alvarez-Guerra, M.; Irabien, A. Design of ionic liquids: an ecotoxicity (Vibrio fischeri) discrimination approach Green Chem. 2011, 13, 1507-1516
23. Torrecilla, J. S.; García, J.; Rojo, E.; Rodríguez, F. Estimation of toxicity of ionic liquids in Leukemia Rat Cell Line and Acetylcholinesterase enzyme by principal component analysis, neural networks and multiple lineal regressions J. Hazard. Mater. 2009, 164, 182-19
24. Ernesto, E. Generalization of topological indexes Chem. Phys. Lett. 2001, 336, 248-252
25. Wiener, H. Structural Determination of Paraffin Boiling Points J. Am. Chem. Soc. 1947, 69, 17-20
26. Schultz, H. P. Topological organic chemistry. 1. Graph theory and topological indexs of alkanes J. Chem. Inf. Comput. Sci. 1989, 29, 227-228
27. Randic, M. Characterization of molecular branching J. Am. Chem. Soc. 1975, 97, 6609-6615
28. Khadikar, P. V.; Kale, P. P.; Deshpande, N. V.; Karmarkar, S.; Agrawal, V. K.; Novel, P. I. Indexes of Hexagonal Chains J. Math. Chem. 2001, 29, 143-150
29. Alexandru, T. B. Highly discriminating distance-based topological index Chem. Phys. Lett. 1982, 89, 399-404
30. Hosoya, H. Topological index: A newly proposed quantity characterizing the topological nature of structural isomers of saturated hydrocarbons Bull. Chem. Soc. Jpn. 1971, 44, 2332-2339
31. Biye, R. Application of novel atom-type AI topological indexs to QSPR studies of alkanes Comput. Chem. 2002, 26, 357-369
32. Kier, L. B.; Hall, L. H. Structure-activity studies on hallucinogenic amphetamines using molecular connectivity J. Med. Chem. 1977, 20, 1631-1636 (Pubitemid 8231440)
33. Estrada, E. Edge adjacency relationships in molecular graphs containing heteroatoms: a new topological index related to molar volume J. Chem. Inf. Comput. Sci. 1995, 35, 701-707
34. Yan, F.; Xia, S.; Wang, Q.; Ma, P. Predicting the Decomposition Temperature of Ionic Liquids by the Quantitative Structure-Property Relationship Method Using a New Topological Index J. Chem. Eng. Data 2012, 57, 805-810
35. Yao, Y.; Xu, L.; Yang, Y.; Yuan, X. Study on structure-activity relationships of organic compounds: Three new topological indexes and their applications J. Chem. Inf. Comput. Sci. 1993, 33, 590-594