The impact of variable selection on the modelling of oestrogenicity

SAR and QSAR in Environmental Research

Volumn 16, Issue 1-2, 2005, Pages 171-190

  Ghafourian, T ^a   Cronin, M T D ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

Descriptors; Oestrogen receptor binding; Oestrogenicity; PLS; QSAR; Variable selection

Indexed keywords

BINDING ENERGY; COMPUTATIONAL CHEMISTRY; GRAPH THEORY; LEAST SQUARES APPROXIMATIONS; MOLECULAR GRAPHICS; PRINCIPAL COMPONENT ANALYSIS; QUANTUM CHEMISTRY; QUANTUM THEORY;

BINDING AFFINITIES; DESCRIPTORS; ESTROGEN RECEPTOR BINDING; OESTROGENICITY; PARTIAL LEAST SQUARE ANALYSIS; PARTIAL LEAST SQUARES MODELS; PARTIAL LEAST-SQUARES; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; STEPWISE REGRESSION; VARIABLES SELECTIONS;

CLUSTER ANALYSIS;

EID: 18244371721     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360412331319808     Document Type: Conference Paper

References (23)

1. Elsby, R., Ashby, J., Sumper, J.P., Brooks, A.N., Pennie, W.D., Maggs, J.L., Lefevre, P.A., Odum, J., Beresford, N., Paton, D. and Park, B.K. (2000) "Obstacles to the prediction of estrogenicity from chemical structure: Assay-mediated metabolic transformation and the apparent promiscuous nature of the estrogen receptor", Biochem. Pharm. 60, 1519-1530.
2. Anstead, G.M., Carlson, K.E. and Katzenellenbogen, J.A. (1997) "The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site", Steroids 62, 268-303.
3. Keasling, H.H. and Schueler, F.W. (1950) "The relationship between estrogenic action and chemical constitution in a group of azomethine derivatives", J. Am. Pharm. Assoc. 39, 87-90.
4. Cronin, M.T.D., Walker, J.D., Jaworska, J.S., Comber, M.H.I., Watts, C.D. and Worth, A.P. (2003) "Use of QSARs in international decision-making frameworks to predict ecologic effects and environmental fate of chemical substances", Environ. Health Perspect. 111, 1376-1390.
5. Cronin, M.T.D., Jaworska, J.S., Walker, J.D., Comber, M.H.I., Watts, C.D. and Worth, A.P. (2003) "Use of QSARs in international decision-making frameworks to predict health effects of chemical substances", Environ. Health Perspect. 111, 1391-1401.
6. Saliner-Gallegos, A., Amat, L., Carbo-Dorca, R., Schultz, T.W. and Cronin, M.T.D. (2003) "Molecular quantum similarity analysis of estrogenic activity", J. Chem. Inf. Comput. Sci. 43, 1166-1176.
7. Shi, L.M., Fang, H., Tong, W., Wu, J., Perkins, R., Blair, R., Branham, W. and Sheehan, D.M. (2001) "QSAR models using a large diverse set of estrogens", J. Chem. Inf. Comput. Sci. 41, 186-195.
8. Blair, R.M., Fang, H., Branham, W.S., Hass, B., Dial, S.L., Moland, C.L., Tong, W., Shi, L., Perkins, R. and Sheehan, D.M. (2000) "The estrogen receptor relative binding affinities of 188 natural and xenochemicals: Structural diversity of ligands", Toxicol. Sci. 54, 138-153.
9. Branham, W.S., Dial, S.L., Moland, C.L., Hass, B., Blair, R., Fang, H., Shi, L., Tong, W., Perkins, R. and Sheehan, D.M. (2002) "Phytoestrogens and mycoestrogens bind to the rat uterine estrogen receptor", J. Nutr. 132, 658-664.
10. Tong, W., Fang, H., Hong, H., Xie, Q., Perkins, R. and Sheehan, D.M. (2004) "Receptor-mediated toxicity: QSARs for oestrogen receptor binding and priority setting of potential oestrogenic endocrine disrupters", In: Cronin, M.T.D. and Livingstone, D.J., eds, Predicting Chemical Toxicology and Fate (CRC Press, Boco Roton, FL), pp 285-314.
11. Fang, H., Tong, W., Shi, L.M., Blair, R., Perkins, R., Branham, W., Hass, B.S., Xie, Q., Dial, S.L., Moland, C.L. and Sheehan, D.M. (2001) "Structure-activity relationships for a large diverse set of natural, synthetic, and environmental oestrogens", Chem. Res. Toxicol. 14, 280-294.
12. Sippl, W. (2002) "Binding affinity prediction of novel estrogen receptor ligands using receptor-based 3-D QSAR methods", Bioorg. Med. Chem. 10, 3741-3755.
13. Kubinyi, H. (2002) "From narcosis to hyperspace: The history of QSAR", QSAR Comb. Chem. 21, 348-356.
14. Hawkins, D.M. (2004) "The problem of overfitting", J. Chem. Inf. Comput. Sci. 44, 1-12.
15. Tang, K. and Li, T. (2002) "Combining PLS with GA-GP for QSAR", Chemom. Intl. Lab. Sys. 64, 55-64.
16. Baroni, M., Clementi, S., Cruciani, G., Costantino, G., Riganelli, D. and Oberrauch, E. (1992) "Predictive ability of regression-models. 2. Selection of the best predictive PLS model", J. Chemom. 6, 347-356.
17. Blower, P., Fligner, M., Verducci, J. and Bjoraker, J. (2002) "On combining recursive partitioning and simulated annealing to detect groups of biologically active compounds", J. Chem. Inf. Comput. Sci. 42, 393-404.
18. Hawkins, D.M. and Kass, G.V. (1982) "Automatic interaction detection", In: Hawkins, D.H., ed., Topics in Applied Multivariate Analysis (Cambridge University Press, Cambridge, UK), pp 269-302.
19. Seibel, G.L. and Kollman, P.A. (1990) "Molecular mechanics and the modelling of drug structures", In: Ramsden, C.A., ed., Comprehensive Medicinal Chemistry, Quantitative Drug Design (Pergamon Press, Oxford), Vol. 4, pp 125-152.
20. Kubinyi, H. (1995) "The quantitative analysis of structure-activity relationships", In: Wolff, M.E., ed., Burger's Medical Chemistry and Drug Discovery, 5th Ed. (Wiley, New York), Vol. 1, pp 497-571.
21. Hall, L.H. and Kier, L.B. (1999) "The kappa indices for modeling molecular shape and flexibility", In: Devillers, J. and Balaban, A.T., eds, Topological Indices and Related Descriptors in QSAR and QSPR (Gordon and Breach, Reading, UK), pp 455-489.
22. De Sant'Annaa, C.M.R., de Alencastrob, R.B. and Barreiroc, E.J. (1999) "Toward a platelet-activating factor pseudoreceptor 2. Three-dimensional semiempirical models for agonist and antagonist binding", J. Mol. Struct. (Theochem) 490, 167-180.
23. Gao, H., Williams, C., Labute, P. and Bajorath, J. (1999) "Binary quantitative structure-activity relationship (QSAR) analysis of estrogen receptor ligands", J. Chem. Inf. Comput. Sci. 39, 164-168.