Development of ecotoxicity QSAR models based on partial charge descriptors for acrylate and related compounds

SAR and QSAR in Environmental Research

Volumn 23, Issue 7-8, 2012, Pages 731-749

  Furuhama, A ^a   Aoki, Y ^a   Shiraishi, H ^a  

^a NATIONAL INSTITUTE FOR ENVIRONMENTAL STUDIES   (Japan)

Author keywords

acrylate, acute fish and Daphnia toxicities; ecotoxicity predictions; partial charges; PEOE; , unsaturated carbonyl compounds

Indexed keywords

CHEMICAL BONDS; COMPUTATIONAL CHEMISTRY; ELECTRONEGATIVITY; FISH; KETONES; MOLECULAR GRAPHICS; TOXICITY; UNSATURATED COMPOUNDS;

ACRYLATE, ACUTE FISH AND DAPHNIA TOXICITY; DAPHNIA; ECOTOXICITY; ECOTOXICITY PREDICTION; EQUALISATION; ORBITALS; PARTIAL CHARGES; PARTIAL EQUALIZATION OF ORBITAL ELECTRONEGATIVITY; UNSATURATED CARBONYL COMPOUNDS; Α,Β-UNSATURATED CARBONYL COMPOUND;

FORECASTING;

EID: 84869473298     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2012.719542     Document Type: Article

References (40)

1. OECD, OECD Environment Monographs No. 58, Report of the OECD workshop on quantitative structure activity relationships (QSARs) in aquatic effects assessment, Paris, 1992. Available athttp://www.oecd.org/dataoecd/19/27/35220377.pdf
2. Netzeva, TI, Pavan, M and Worth, AP. 2008. Review of (quantitative) structure-activity relationships for acute aquatic toxicity. QSAR Comb. Sci., 27: 77-90.
3. Worth, A, Netzeva, TI and Patlewicz, G. 2007. "10. Predicting toxicological and ecotoxicological endpoints". In Risk assessment of chemicals: an introduction, Edited by: Van Leeuwen, F.W. and Vermeire, T.G. 576-578. The Netherlands, Dordrecht: Springer-Verlag.
4. OECD, OECD Environment health and safety publications series on testing and assessment No. 58, Report on the regulatory uses and applications in OECD member countries of (quantitative) structure-activity relationship [(Q)SAR] models in the assessment of new and existing chemicals, Paris, 2006. Available athttp://www.oecd.org/dataoecd/55/22/38131728.pdf
5. OECD, OECD Environment health and safety publications series on testing and assessment No. 69, Guidance document on the validation of (quantitative) structure-activity relationships [(Q)SAR] models, Paris, 2007. Available athttp://www.oecd.org/dataoecd/55/35/38130292.pdf
6. OECD, OECD Quantitative structure-activity relationships project [(Q)SARs], Paris. Available athttp://www.oecd.org/env/hazard/qsar
7. ECOSAR. Available athttp://www.epa.gov/oppt/newchems/tools/21ecosar.htm
8. Verhaar, HJM, Vanleeuwen, CJ and Hermens, JLM. 1992. Classifying environmental pollutants. 1: Structure-activity relationships for prediction of aquatic toxicity. Chemosphere, 25: 471-491.
9. KATE, KAshinou Tool for Ecotoxicity (KATE) is an ecotoxicity QSAR modeling system researched and developed by the Research Center for Environmental Risk at the National Institute for Environmental Studies under contract from the Ministry of the Environment from FY 2004 to FY2010. Available athttp://kate.nies.go.jp
10. Furuhama, A, Toida, T, Nishikawa, N, Aoki, Y, Yoshioka, Y and Shiraishi, H. 2010. Development of an ecotoxicity QSAR model for the KAshinhou Tool for Ecotoxicity (KATE) system, March 2009 version. SAR QSAR Environ. Res., 21: 403-413.
11. Furuhama, A, Hasunuma, K, Aoki, Y, Yoshioka, Y and Shiraishi, H. 2011. Application of chemical reaction mechanistic domains to an ecotoxicity QSAR model, KAshinhou Tool for Ecotoxicity (KATE). SAR QSAR Environ. Res., 22: 505-523.
12. Ministry of the Environment in Japan, Results of eco-toxicity tests data conducted by Ministry of the Environment in Japan. Available athttp://www.env.go.jp/chemi/sesaku/02e.pdf
13. US EPA, US Environmental Protection Agency's fathead minnow database. Available athttp://www.epa.gov/med/Prods_Pubs/fathead_minnow.htm
14. Dimitrov, S, Pavlov, T, Veith, G and Mekenyan, O. 2011. Simulation of chemical metabolism for fate and hazard assessment. I. Approach for simulating metabolism. SAR QSAR Environ. Res., 22: 699-718.
15. Dimitrov, S, Pavlov, T, Dimitrova, N, Georgieva, D, Nedelcheva, D, Kesova, A, Vasilev, R and Mekenyan, O. 2011. Simulation of chemical metabolism for fate and hazard assessment. II CATALOGIC simulation of abiotic and microbial degradation. SAR QSAR Environ. Res., 22: 719-755.
16. Dimitrov, S, Dimitrova, N, Georgieva, D, Vasilev, K, Hatfield, T, Straka, J and Mekenyan, O. 2012. Simulation of chemical metabolism for fate and hazard assessment. III. New developments of the bioconcentration factor base-line model. SAR QSAR Environ. Res., 23: 17-36.
17. Dimitrov, S, Dimitrova, N, Parkerton, T, Comber, M, Bonnell, M and Mekenyan, O. 2005. Base-line model for identifying the bioaccumulation potential of chemicals. SAR QSAR Environ. Res., 16: 531-554.
18. Dimitrov, SD, Dimitrova, NC, Walker, JD, Veith, GD and Mekenyan, OG. 2003. Bioconcentration potential predictions based on molecular attributes-an early warning approach for chemicals found in humans, birds, fish and wildlife. QSAR Comb. Sci., 22: 58-68.
19. Moosus, M and Maran, U. 2011. Quantitative structure-activity relationship analysis of acute toxicity of diverse chemicals to Daphnia magna with whole molecule descriptors. SAR QSAR Environ. Res., 22: 757-774.
20. Furuhama, A, Aoki, Y and Shiraishi, H. 2012. Consideration of reactivity to acute fish toxicity of α,β- unsaturated carbonyl ketones and aldehydes. SAR QSAR Environ. Res., 23: 169-184.
21. Schwöbel, JAH, Koleva, YK, Enoch, SJ, Bajot, F, Hewitt, M, Madden, JC, Roberts, DW, Schutz, TW and Cronin, MTD. 2011. Measurement and estimation of electrophilic reactivity for predictive toxicology. Chem. Rev., 111: 2562-2596.
22. Schultz, TW, Netzeva, TI, Roberts, DW and Cronin, MTD. 2005. Structure-toxicity relationships for the effects to Tetrahymena pyriformis of aliphatic, carbonyl-containing, alpha, beta-unsaturated chemicals. Chem. Res. Toxicol., 18: 330-341.
23. Yarbrough, JW and Schultz, TW. 2007. Abiotic sulfhydryl reactivity: A predictor of aquatic toxicity for carbonyl-containing alpha, beta-unsaturated compounds. Chem. Res. Toxicol., 20: 558-562.
24. Roberts, DW and Natsch, A. 2009. High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of Michael acceptor electrophiles. Chem. Res. Toxicol., 22: 592-603.
25. Schwöbel, JAH, Wondrousch, D, Koleva, YK, Madden, JC, Cronin, MTD and Schüürmann, G. 2010. Prediction of Michael-type acceptor reactivity toward glutathione. Chem. Res. Toxicol., 23: 1576-1585.
26. Gasteiger, J and Marsili, M. 1980. Iterative partial equalization of orbital electronegativity-a rapid access to atomic charges. Tetrahedron, 36: 3219-3228.
27. Russom, CL, Bradbury, SP, Broderius, SJ, Hammermeister, DE and Drummond, RA. 1997. Predicting modes of toxic action from chemical structure: Acute toxicity in the fathead minnow (Pimephales promelas). Environ. Toxicol. Chem., 16: 948-967.
28. Molecular Operating Environment (MOE), 2008.1002, Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada H3A 2R7, 2008
29. Frisch, MJ, Trucks, GW, Schlegel, HB, Scuseria, GE, Robb, MA, Cheeseman, JR, Scalmani, G, Barone, V, Mennucci, B, Petersson, GA, Nakatsuji, H, Caricato, M, Li, X, Hratchian, HP, Izmaylov, AF, Bloino, J, Zheng, G, Sonnenberg, JL, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Vreven, T, Montgomery, J.A. Jr, Peralta, JE, Ogliaro, F, Bearpark, M, Heyd, JJ, Brothers, E, Kudin, KN, Staroverov, VN, Kobayashi, R, Normand, J, Raghavachari, K, Rendell, A, Burant, JC, Iyengar, SS, Tomasi, J, Cossi, M, Rega, N, Millam, JM, Klene, M, Knox, JE, Cross, JB, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, RE, Yazyev, O, Austin, AJ, Cammi, R, Pomelli, C, Ochterski, JW, Martin, RL, Morokuma, K, Zakrzewski, VG, Voth, GA, Salvador, P, Dannenberg, JJ, Dapprich, S, Daniels, AD, Farkas, O, Foresman, JB, Ortiz, JV, Cioslowski, J and Fox, DJ. 2009. Gaussian 09, Revision A.02, Wallingford CT: Gaussian, Inc.
30. Sadowski, J, Gasteiger, J and Klebe, G. 1994. Comparison of automatic 3-dimensional model builders using 639 X-Ray structures. J. Chem. Inf. Comput. Sci., 34: 1000-1008.
31. CORINA, The 3D structure generator CORINA. Information is available at http://www.molecular-networks.com, Molecular Networks GmbH, Erlangen, Germany
32. Weininger, D. 1988. SMILES, A chemical language and information-system. 1. Introduction to methodology and encoding rules. J. Chem. Inf. Comput. Sci., 28: 31-36.
33. PEOE_PC- in MOE. Available athttp://www.chemcomp.com/journal/descr.htm#Charge
34. Jensen, F. 2007. Wave function analysis, in Introduction to computational chemistry, 293-314. Chichester: John Wiley & Sons Ltd.
35. Gasteiger, J. 2003. "Empirical approaches to the calculation of properties". In Chemoinformatics: A Textbook, Edited by: Gasteiger, J. and Engel, T. 320-337. KGaA, Weinheim: WILEY-VHC GmbH & Co.
36. R Development Core Team, R: A Language and Environment for Statistical Computing, The R foundation for statistical Computing, Vienna, Austria, 2008
37. Putz, MV. 2010. On absolute aromaticity within electronegativity and chemical hardness reactivity pictures. MARCH, 64: 391-418.
38. Putz, MV. 2006. Systematic formulations for electronegativity and hardness and their atomic scales within density functional softness theory. Int. J. Quantum. Chem., 106: 361-389.
39. Chicu, SA and Putz, MV. 2009. Koln-Timisoara molecular activity combined models toward interspecies toxicity assessment. Int. J. Mol. Sci., 10: 4474-4497.
40. ClogP, See the CLOGP reference manual at http://www.daylight.com/dayhtml/doc/clogp/index.html. The underlying program of CLOGP is copyrighted by Pomona College and BioByte, Inc. (Claremont, CA)