Quantum chemistry based quantitative structure-activity relationships for modeling the (sub)acute toxicity of substituted mononitrobenzenes in aquatic systems

Environmental Toxicology and Chemistry

Volumn 25, Issue 9, 2006, Pages 2313-2321

  Zvinavashe, Elton ^a   Murk, Albertinka J ^a   Vervoort, Jacques ^a   Soffers, Ans E M F ^a   Freidig, Andreas ^a,b   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b TNO   (Netherlands)

Author keywords

Acute toxicity; Octanol water partition coefficient; Quantitative structure activity relationships; Quantum mechanics; Substituted mononitrobenzene

Indexed keywords

ALGAE; BACTERIA; ENVIRONMENTAL PROTECTION; FISHERIES; TOXICITY; WATER POLLUTION;

ACUTE TOXICITY; OCTANOL/WATER PARTITION COEFFICIENTS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS; SUBSTITUTED MONONITROBENZENE;

QUANTUM THEORY;

MONONITROBENZENE DERIVATIVE; NITROBENZENE DERIVATIVE; OCTANOL; UNCLASSIFIED DRUG;

ALGA; AQUATIC ECOSYSTEM; BACTERIUM; BENZENE; DATA SET; EXPERIMENTAL STUDY; PROTOZOAN; TOXICITY; YEAST;

ALGA; AQUATIC ENVIRONMENT; CARP; CHLORELLA; CHLORELLA VULGARIS; CONFERENCE PAPER; DAPHNIA; PARTITION COEFFICIENT; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY; SACCHAROMYCES CEREVISIAE; SCENEDESMUS; TETRAHYMENA PYRIFORMIS; ANIMAL; ARTICLE; BACTERIUM; BIOLOGICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYPRINODONTIFORMES; DRUG EFFECT; ECOSYSTEM; ENVIRONMENTAL MONITORING; METHODOLOGY; PHYSIOLOGY; SPECIES DIFFERENCE; TETRAHYMENA; WATER POLLUTANT;

ALGAE; CHLORELLA PYRENOIDOSA; CYPRINUS CARPIO; DAPHNIA MAGNA; DAPHNIIDAE; PHOTOBACTERIUM PHOSPHOREUM; POECILIA RETICULATA; PROTOZOA; SACCHAROMYCES CEREVISIAE; SCENEDESMUS OBLIQUUS; TETRAHYMENA PYRIFORMIS;

ANIMALS; BACTERIA; CARPS; CHLORELLA; COMBINATORIAL CHEMISTRY TECHNIQUES; DAPHNIA; ECOSYSTEM; ENVIRONMENTAL MONITORING; MODELS, BIOLOGICAL; NITROBENZENES; POECILIA; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SACCHAROMYCES CEREVISIAE; SCENEDESMUS; SPECIES SPECIFICITY; TETRAHYMENA; WATER POLLUTANTS, CHEMICAL;

EID: 33750597408     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/05-678R.1     Document Type: Conference Paper

References (40)

1. European Union. 2001. White paper: Strategy for a future chemicals policy. COM(2001) 88 final. Commission of the European Committees, Brussels, Belgium.
2. Worth AP, Van Leeuwen CJ, Hartung T. 2004. The prospects for using (Q)SARs in a changing political environment-High expectations and a key role for the European Commission's joint research centre. SAR and QSAR in Environmental Research 15: 331.
3. U.S. Environmental Protection Agency. 2002. Endocrine disruptor screening program, proposed chemical selection approach for initial round of screening; request for comment. FRL-7286-6. Washington, DC.
4. Netherlands Health Council. 2001. Toxicity testing: A more efficient approach. Publication 2001/24E. The Hague, The Netherlands.
5. Abraham MH, Chadha HS, Martins F, Mitchell RC, Bradbury MW, Gratton JA. 1999. Hydrogen bonding part 46: A review of the correlation and prediction of transport properties by an LFER method: Physicochemical properties, brain penetration and skin permeability. Pestic Sci 55:78.
6. Hansch C, Fujita T. 1964. A method for the correlation of biological activity and chemical structure. J Am Chem Soc 86:1616-1626.
7. Soffers AEMF, Boersma MG, Vaes WHJ, Vervoort J, Tyrakowska B, Hermens JLM, Rietjens IMCM. 2001. Computer-modeling-based SARs for analyzing experimental data on biotransformation and toxicity. Toxicol In Vitro 15:539-551.
8. Friedig AP, Hermens JL. 2000. Narcosis and chemical reactivity QSARs for acute fish toxicity. Quant Struct-Act Relat 19:547-553.
9. Cronin MT, Gregory BW, Schultz TW. 1998. Quantitative structure-activity analyses of nitrobenzene toxicity to Tetrahymena pyriformis. Chem Res Toxicol 11:902-908.
10. Bohac M, Loeprecht B, Damborsky J, Schüürmann G. 2002. Impact of orthogonal signal correction (OSC) on the predictive ability of CoMFA models for the ciliate toxicity of nitrobenzenes. Quant Struct-Act Relat 21:3-11.
11. Wang X, Yin C, Wang L. 2002. Structure-activity relationships and response-surface analysis of nitroaromatics toxicity to the yeast (Saccharomyces cerevisiae). Chemosphere 46:1045-1051.
12. O'Brien PJ, Wong WC, Silva J, Khan S. 1990. Toxicity of nitrobenzene compounds towards isolated hepatocytes: Dependence on reduction potential. Xenobiotica 20:945-955.
13. Zhao Y-H, Yuan X, Ji G-D, Sheng L-X, Wang L-S. 1997. Quantitative structure-activity relationships of nitroaromatic compounds to four aquatic organisms. Chemosphere 34:1837-1844.
14. Deneer JW, Sinnige TL, Seinen W, Hermens JLM. 1987. Quantitative structure-activity relationships for the toxicity and bio-concentration factor of nitrobenzene derivatives towards the guppy (Poecilia reticulata). Aquat Toxicol 10:115-129.
15. Deneer JW, van Leeuwen CJ, Seinen W, Maas-Diepeveen JL, Hermens JLM. 1989. QSAR study of the toxicity of nitrobenzene derivatives towards Daphnia magna, Chlorella pyrenoidosa, and Photobacterium phosphoreum. Aquat Toxicol 15:83-98.
16. Lu G-H, Yuan X, Zhao Y-H. 2001. QSAR study on the toxicity of substituted benzenes to the algae (Scenedesmus obliquus). Chemosphere 44:437-440.
17. Netzeva TI, Dearden JC, Edwards R, Worgan ADP, Cronin MTD. 2004. QSAR analysis of the toxicity of aromatic compounds to Chlorella vulgaris in a novel short-term assay. J Chem Inf Comput Sci 44:258-265.
18. Leo A. 1993. Calculating log Poet from structures. Chem Rev 93:1281-1306.
19. Tetko IV, Tanchuk VY. 2002. Application of associative neural networks for prediction of lipophilicity in ALOGPS 2.1 program. J Chem Inf Comput Sci 42:1136-1145.
20. Meylan WM, Howard PH. 1995. Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 84:83-92.
21. Petrauskas AA, Kolovanov EA. 2000. ACD/Log P method description. Perspect Drug Discov Des 19:99-116.
22. Weininger D. 1988. SMILES 1. Introduction and Encoding Rules. J Chem Inf Comput Sci 28:31.
23. Dewar M, Zoebisch E, Healy E, Stewart J. 1985. AM1: A new general purpose quantum mechanical molecular model. J Am Chem Soc 107:3902-3909.
24. Tropsha A, Gramatica P, Gombar VK. 2003. The importance of being earnest: Validation is the absolute essential for successful application and interpretation of QSPR models. QSAR & Combinatorial Science 22:69-77.
25. Eriksson L, Jaworska J, Worth AP, Cronin MT, McDowell RM, Gramatica P. 2003. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ Health Perspect 111:1361-1375.
26. Diamantidis NA, Karlis D, Giakoumakis EA. 2000. Unsupervised stratification of cross-validation for accuracy estimation. Artificial Intelligence 116:1-16.
27. Khadikar PV, Karmarkar S, Singh S, Shrivastava A. 2002. Use of the PI index in predicting toxicity of nitrobenzene derivatives. Bioorg Med Chem 10:3163-3170.
28. Cronin MTD, Schultz TW. 2003. Pitfalls in QSAR. Journal of Molecular Structure: THEOCHEM 622:39-51.
29. Van Leeuwen CJ, Van der Zandt PTJ, Aldenberg T, Verhaar HJM, Hermens JLM. 1992. Application of QSARs, extrapolation and equilibrium partitioning in aquatic effects assessment. I. Narcotic industrial pollutants. Environ Toxicol Chem 11:267-282.
30. Organization for Economic Cooperation and Development. 2004. The report from the expert group on (quantitative) structure-activity relationship ((Q)SARs) on the principles for the validation of (Q)SARS. ENV/JM/MONO(2004)24. Paris, France.
31. Hall LH, Kier LB. 1995. Electrotopological state indices for atom types: A novel combination of electronic, topological, and valence state information. J Chem Inf Comput Sci 35:1039-1045.
32. Ghose A, Pritchett A, Crippen G. 1988. Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships III: Modeling hydrophobic interactions. Journal of Computational Chemistry 9:80-90.
33. ow based QSARs: Application to nitro compounds. Environ Toxicol Chem 12:1847-1849.
34. Vaes WH, Ramos EU, Verhaar HJ, Cramer CJ, Hermens JL. 1998. Understanding and estimating membrane/water partition coefficients: Approaches to derive quantitative structure property relationships. Chem Res Toxicol 11:847-854.
35. Katritzky AR, Oliferenko P, Oliferenko A, Lomaka A, Karelson M. 2003. Nitrobenzene toxicity: QSAR correlations and mechanistic interpretations. Journal of Physical Organic Chemistry 16:811-817.
36. Roy K, Ghosh G. 2004. QSTR with extended topochemical atom indices. 4. Modeling of the acute toxicity of phenylsulfonyl carboxylates to Vibrio fischeri using principal component factor analysis and principal component regression analysis. QSAR & Combinatorial Science 23:526.
37. Xu JB, Jing TS, Pauli W, Berger S. 2002. Quantitative structure-activity relationships for the toxicity of nitrobenzenes to Tetrahymena thermophila. J Environ Sci Health Part A Toxic Hazard Subst Environ Eng 37:563.
38. Organization for Economic Cooperation and Development. 2001. Guidance document on the use of the harmonized system for the classification of chemicals which are hazardous to the aquatic environment. ENV/JM/MOMO (2001)8. Technical Report. Paris, France.
39. Verhaar HJM, van Leeuwen CJ, Hermens JLM. 1992. Classifying environmental pollutants. Chemosphere 25:471-491.
40. European Commission. 2002. Guidance document on aquatic ecology. Sanco/3268/2001. Technical Report. Brussels, Belgium.