QSAR modeling of bioconcentration factor by theoretical molecular descriptors

QSAR and Combinatorial Science

Volumn 22, Issue 3, 2003, Pages 374-385

  Gramatica, Paola ^a   Papa, Ester ^a  

^a UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

BCF; External validation; Genetic Algorithms; QSAR; Theoretical molecular descriptors

Indexed keywords

AQUATIC ORGANISMS; BIOACCUMULATION; COMPUTATIONAL CHEMISTRY; LINEAR REGRESSION; THREE DIMENSIONAL COMPUTER GRAPHICS;

BIO-CONCENTRATION FACTORS; CHEMICAL CONCENTRATIONS; ECOTOXICOLOGICAL; EXTERNAL VALIDATION; LOG KOW; MOLECULAR CONNECTIVITY; MOLECULAR DESCRIPTORS; QSAR; QSAR MODELING; THEORETICAL MOLECULAR DESCRIPTOR;

GENETIC ALGORITHMS;

ALGORITHM; AQUATIC ENVIRONMENT; BIOACCUMULATION; BIOCONCENTRATION FACTOR; CONFERENCE PAPER; ECOTOXICOLOGY; LINEAR REGRESSION ANALYSIS; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; STATISTICAL MODEL; THEORY; VALIDATION PROCESS;

EID: 0037709858     PISSN: 1611020X     EISSN: None     Source Type: Journal    
DOI: 10.1002/qsar.200390027     Document Type: Conference Paper

References (60)

1. Veith, G. D., DeFoe, D. L., and Bergstedt, B.V., Measuring and estimating the bioconcentration factor of chemicals in fish, J. Fish Res. Board Can. 36, 1040-1048 (1979).
2. Barron, M. G., Bioconcentration, Environ. Sci. Technol. 24, 1612-1618 (1990).
3. U.S. E.P.A. Fish BCF, OPPTS 850.1730. EPA/712-C-96-129, Washington, DC 1996.
4. U.S. E.P.A. Oyster BCF, OPPTS 850.1710. EPA/712-96-127, Washington, DC 1996.
5. European Centre for Ecotoxicology and Toxicology of Chemicals, The Role of Bioaccumulation in Environmental Risk Assessment: The Aquatic Environment and Related Food Webs, Technical report 67, ECETOC, Brussels (Belgium) 1996, p.112.
6. OECD. Guidelines for testing of chemicals. Proposal for updating Guidelines 305, 1996, Paris.
7. Neely, B. W., Branson, D. R., and Blau, G. E., Partition Coefficient to Measure Bioconcentration Potential of Organic Chemicals in Fish, Environ. Sci. Technol. 8, 1113-1115 (1974).
8. Kanazawa, J., Measurement of the Bioconcentration Factors of Pesticides by Freshwater Fish and their Correlation with Physicochemical Properties or Acute Toxicities, Pestic. Sci.12, 417-424 (1981).
9. Mackay, D., Correlation of Bioconcentration Factors, Environ. Sci. Technol. 16, 274-278 (1982).
10. Veith, G. D., and Kosian, P., Estimating Bioconcentration Potential from Octanol/Water Partition Coefficients, in: Mackay, D. et al. (Ed), Physical Behaviour of PCBs in the Great Lakes, Ann Arbor Science Pub., Ann Arbor, MI, (USA) 1983, pp.269-282.
11. Isnard, P., and Lambert, S., Estimating Bioconcentration Factors from Octanol-Water Partition Coefficient and Aqueous Solubility, Chemosphere 17, 21-34 (1988).
12. Schüürmann, G., and Klein, W., Advances in Bioconcentration Prediction, Chemosphere 17, 1551-1574 (1988).
13. Dimitrov, S. V., Mekenyan, O. G., and Walker, J. D., Non-Linear Modeling of Bioconcentration Using Partition Coefficients for Narcotic Chemicals, SAR QSAR Environ. Res. 13, 177-184 (2002).
14. Bintein, S., Devillers, J., and Karcher, W., Nonlinear Dependence of Fish Bioconcentration on n-Octanol/Water Partition Coefficient, SAR QSAR Environ. Res. 1, 29-39 (1993).
15. Kubinyi, H., Nonlinear Dependence of Biological activity on Hydrophobic Character, J. Med. Chem. 20, 625-629 (1977).
16. ow/logBCF Correlations, in: R. Nagel and R. Loskill, (Ed), Bioaccumulation in Aquatic Systems, VCH, Weinheim 1991. pp. 43-66.
17. Connell, D. W., and Hawker, D. W., Use of Polynomial Expression to describe the Bioconcentration of Hydrophobic Chemicals by Fish, Ecotox. Environ. Safety 16, 242-257 (1988).
18. Devillers, J., Bintein, S., and Domine, D., Comparison of BCF Models Based on LogP, Chemosphere 33, 1047-1065 (1996).
19. Meylan, W. M., Howard, P. H., Boethling, R. S., Aronson, D., Printup, H., and Gouichie, S., Improved Method for Estimating Bioconcentration/Bioaccumulation Factor from Octanol/Water Partition Coefficient, Environ. Toxicol. Chem. 18, 664-672 (1999).
20. Mackay, D., and Fraser, A., Bioaccumulation of Persistent Organic Chemicals: Mechanisms and Models, Environ. Pollution 110, 375-391 (2000).
21. Davies, R. P., and Dobbs, A. J., The Prediction of Bioconcentration in Fish, Water Res. 18, 1253-1262 (1984).
22. Kenaga, E. E., and Goring, C. A. I., Relationship between Water Solubility, Soil Sorption, Octanol-Water Partitioning and Bioconcentration of Chemicals in Biota, in: Eaton J. G., Parrish P. R., Hendricks A. C. (Ed), Aquatic Toxicology, ASTM STP707 1980, pp. 78-115.
23. Sabljic, A., and Protic, M., Molecular Connectivity: A Novel Method for Prediction of Bioconcentration Factor of Hazardous Chemicals, Chem. Biol. Interact. 42, 301-310 (1982).
24. Connell, D. W, and Schüürmann, G., Evaluation of Various Molecular Parameters as Predictors of Bioconcentrations in Fish, Ecotox. Environ. Safety. 15, 324-335 (1988).
25. Lu, X., Tao, S., Cao, J., and Dawson, R. W., Prediction of Fish Bioconcentration Factors of Nonpolar Organic Pollutants Based on Molecular Connectivity Indices, Chemosphere 39, 987-999 (1999).
26. Tao, S. Hu, H., Lu, X., Dawson, R. W., and Xu, F., Fragment Constant Method for Prediction of Fish Bioconcentration Factors of Non-Polar Chemicals, Chemosphere 41, 1563-1568 (2000).
27. Lu, X., Tao, S., Hu, H., and Dawson, R. W., Estimation of Bioconcentration Factors of Nonionic Organic Compounds in Fish by Molecular Connectivity Indices and Polarity Correction Factors, Chemosphere 41, 1675-1688 (2000).
28. Nishihara, T., Saito, S., and Matsuo, M., Bioconcentration of Organic Chemicals in Fish: Mechenism and Structure Activity Relationship (SAR), in: Ecological Issues and Environmental Impact Assessment, 1997. pp. 707-764.
29. Todeschini, R., and Consonni, V., DRAGON-Software for the Calculation of Molecular Descriptors, rel.1.12 for Windows (2001).
30. HYPERCHEM, rel.4 for Windows, Autodesk, Inc., Sausalito. CA (USA), (1995).
31. Todeschini, R., Lasagni, M., and Marengo, E., New Molecular Descriptors for 2D and 3D Structures, J. Chemometrics 8, 263-273 (1994).
32. Todeschini, R., and Gramatica, P., 3D-modelling and prediction by WHIM descriptors. Part 5. Theory development and chemical meaning of the WHIM descriptors, Quant. Struct.-Act.Relat. 16, 113-119 (1997).
33. Consonni, V., Todeschini, R., and Pavan, M., Structure/Response Correlation and Similarity/Diversity Analysis by GETAWAY Descriptors. Part 1. Theory of the Novel 3D Molecular Descriptors, J. Chem. Inf. Comput. Sci. 42, 682-692 (2002).
34. Consonni, V., Todeschini, R., Pavan, M., and Gramatica, P., Structure/Response Correlations and Similarity/Diversity Analysis by GETAWAY descriptors. Part 2. Application of the novel 3D-molecular descriptors to QSAR/QSPR studies, J. Chem. Inf. Comput. Sci. 42, 693-705 (2002).
35. Todeschini, R., and Consonni, V., Handbook of Molecular Descriptors, Wiley-VCH, Weinheim (Germany) 2000, pp. 667.
36. CHEM 3D-Cambridge Soft, MA, USA, (1997).
37. BCFWIN v. 2.14 in U.S.EPA, EPIWIN Package, 2000.
38. Todeschini, R., MOBY DIGS-Software for Multilinear Regression Analysis and Variable Subset Selection by Genetic Algorithm, rel. 2.1 for Windows, Talete srl, Milan (Italy), (1997).
39. Leardi, R., Boggia, R., and Terrile, M., Genetic Algorithms as a Strategy for Feature Selection, J. Chemom. 6, 267-281 (1992).
40. Todeschini, R., Mauri, A., DOLPHIN-Software for Optimal Distance-Based Experimental Design rel. 1.1 for Windows, Talete srl, Milan (Italy), (2000).
41. SCAN-Software for Chemometric Analysis, rel.1.1 for Windows, Minitab (USA), (1995).
42. Davis, L., Handbook of Genetic Algorithms, Van Nostrand Reinhold, N.Y. (USA) 1991.
43. Devillers, J., Genetic Algorithms in Molecular Modelling, Academic Press Ltd., London 1996.
44. Todeschini, R., and Gramatica P., 3D-Modelling and Prediction by WHIM Descriptors. Part 6. Applications of WHIM Descriptors in QSAR Studies., Quant.Struct.-Act.Relat. 16, 120-125 (1997).
45. Gramatica, P., Navas, N., and Todeschini, R., 3D-Modelling and Prediction by WHIM Descriptors. Part 9. Chromatographic Relative Retention Time and Physico-Chemical Properties of Polychlorinated Biphenyls (PCBs), Chemom. Intell. Lab. Sys. 40, 53-63 (1998).
46. Gramatica, P., Consonni, V., and Todeschini, R., QSAR Study on the Tropospheric Degradation of Organic Compounds, Chemosphere 38, 371-1378 (1999).
47. Gramatica, P., Corradi, M., and Consonni, V., Modelling and Prediction of Soil Sorption Coefficients of non-ionic organic pesticides by different sets of molecular descriptors, Chemosphere 41, 763-777 (2000).
48. Atkinson, A. C., Plots, Transformations and Regression, Clarendon Press, Oxford (UK) 1985, pp.282.
49. Gombar, V. K., and Enslein, K., Assessment of n-Octanol/Water Partition Coefficient: When is the Assessment Reliable?, J. Chem. Inf. Comput. Sci. 36, 1127-1134 (1996).
50. Todeschini, R., Maiocchi, A., and Consonni, V., The K correlation Index: Theory Development and its Application in Chemometrics, Chemom. Int. Lab. Syst. 46, 13-29 (1999).
51. Wold, S., and Eriksson, L., Chemometric Methods in Molecular Design, VCH, Germany 1995, pp. 309-318.
52. Shi, L. M., Fang, H., Tong, W., Wu, J., Perkins, R., Blair, R. M., Branham, W. S., Dial, S. L., Moland, C. L., and Sheehan, D. M., QSAR Models Using a Large Diverse Set of Estrogens, J. Chem. Inf. Comput. Sci. 41, 186-195 (2001).
53. Cramer, R. D., Patterson, D. E., and Bunce, J. D., Comparative Molecular Field Analysis (CoMFA). 1. Effect of Shape on Binding of Steroids to Carrier Proteins, J. Am. Chem. Soc. 110, 5959-5967 (1988).
54. 2!, J. Mol. Graph and Mod. 20, 269-276 (2002).
55. Bonchev, D., Information Theoretic Indices for Characterization of Chemical Structures, Research Studies Press, Chichester (U.K.) 1983, pp. 249.
56. Moran, P. A. P., Notes on Continuous Stochastic Phenomena, Biometrika 37, 17-23 (1950).
57. Geary, R. C., The Contiguity Ratio and Statistical Mapping, Incorp. Statist. 5, 115-145 (1954).
58. Devillers, J., QSAR Modeling of Large Heterogeneous Sets of Molecules, SAR QSAR Environ. Res. 12, 515-528 (2001).
59. Kaiser, K. L. E., Dearden, J. C., Klein, W., Schultz, T. W., A Note of Caution to Users of ECOSAR, Water Qual. Res. J. Canada 34, 179-182 (1999).
60. ECOSAR, Version 0.99f, in U.S. EPA, EPIWIN package, 2000.