Comparison of electrotopological-state indices versus atomic charge and superdelocalisability indices in a QSAR study of the receptor binding properties of halogenated estradiol derivatives

Molecular Diversity

Volumn 8, Issue 4, 2004, Pages 343-355

  Ghafourian, Taravat ^a   Cronin, Mark T D ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

atomic charges; electrotopological index; estradiol; oestrogen receptor binding; oestrogenicity; QSAR; superdelocalisability index

Indexed keywords

ESTRADIOL; ESTRADIOL DERIVATIVE; ESTROGEN RECEPTOR; ETHINYLESTRADIOL;

ACCURACY; ARTICLE; ATOM; BINDING AFFINITY; CHEMICAL PARAMETERS; COMPARATIVE STUDY; DRUG STRUCTURE; HALOGENATION; HEALTH HAZARD; PREDICTION; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RECEPTOR BINDING; RISK ASSESSMENT;

ANIMALS; ELECTROPHYSIOLOGY; ESTRADIOL; ESTROGENS; LEAST-SQUARES ANALYSIS; MODELS, CHEMICAL; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTORS, ESTROGEN; REGRESSION ANALYSIS; REPRODUCIBILITY OF RESULTS; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 8544271631     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1023/B:MODI.0000047499.11033.83     Document Type: Article

References (63)

1. Colborn, T., vom Saal, F.S. and Soto, A.M., Development effects of endocrine disrupting chemicals in wildlife and humans, Environ. Health Perspect., 101 (1993) 378-384.
2. Williams, C.L. and Stancel, G.M., Estrogens and progestins, In Hardman, J.G. and Limbird, L.E. (Eds.), Goodman and Gillman's the Pharmacological Basis of Therapeutics, 9th ed., McGraw-Hill, New York, 1996, pp. 1411-1440.
3. Goldstein, S.R., Siddhanti, S., Ciaccia, A.V. and Plouffe, L., A pharmacological review of selective oestrogen receptor modulators, Hum. Reprod. Update, 6 (2000) 212-224.
4. Burger, H.G., Selective oestrogen receptor modulators, Horm. Res., 53 (2000) (Suppl. 3) 25-29.
5. Tsai, M.-J. and O'Malley, B.W., Molecular mechanisms of action of steroid/thyroid receptor superfamily members, Ann. Rev. Biochem., 63 (1994) 451-486.
6. Brzozowski, A.M., Pike, A.C.W., Dauter, Z., Hubbard, R.E., Bonn, T., Engstrom, O., Ohman, L., Greene, G.L., Gustafsson, J.A., Carlquist, M., Molecular basis of agonism and antagonism in the oestrogen receptor, Nature, 389 (1997) 753-758.
7. Pike, A.C.W., Brzozowski, A.M., Hubbard, R.E., Bonn, T., Thorsell, A.G., Engstrom, O., Ljunggren, J., Gustafsson, J.A. and Carlquist, M., Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist, EMBO J., 18 (1999) 4608-4618.
8. Hubbard, R.E., Pike, A.C.W., Brzozowski, A.M., Walton, J., Bonn, T., Gustafsson, J.A and Carlquist, M., Structural insights into the mechanisms of agonism and antagonism in oestrogen receptor isoforms, Eur. J. Cancer, 36 (2000) S13-S23.
9. Schultz, T.W., Sinks, G.D. and Cronin, M.T.D., Effect of substituent size and dimentionality on potency of phenolic xenoestrogenes evaluated with a recombinant yeast assay, Environ. Toxicol. Chem., 19 (2000) 2637-2642.
10. Saliner, A.G., Amat, L., Carbo-Dorca, R., Schultz, T.W. and Cronin, M.T.D., Molecular quantum similarity analysis of oestrogenic activity, J. Chem. Inf. Comp. Sci., 43 (2003) 1166-1176.
11. Schmieder, P.K., Aptula, A.O., Routledge, E.J., Sumpter, J.P. and Mekenyan, O.G., Oestrogenicity of alkylphenolic compounds: A 3-D structure-activity evaluation of gene activation, Environ. Toxicol. Chem., 19 (2000) 1727-1740.
12. Bradbury, S., Kamenska, V., Schmieder, P., Ankley, G. and Mekenyan, O., A computationally based identification algorithm for oestrogen receptor ligands: Part 1. Predicting hERα binding affinity, Toxicol. Sci., 58 (2000) 253-269.
13. Waller, C.L., Opera, T.I., Chae, K., Park, H.-K., Korach, K.S., Laws, S.C., Wiese, T.E., Kelce, W.R. and Gray, L.E., Ligand-based identi fication of environmental oestrogens, Chem. Res. Toxicol., 9 (1996) 1240-1248.
14. Shi, L.M., Fang, H., Tong, W., Wu, J., Perkins, R., Blair, R., Branham, W.S., Dial, S.L., Moland, C.L. and Sheehan, D.M., QSAR models using a large diverse set of oestrogens, J. Chem. Inf. Comput. Sci., 41 (2001) 186-195.
15. Dawson, D.A., Schultz, T.W., Baker, L.L. Mannar, A., Structure-activity relationships for osteolathyrism: Part III. Substituted thiosemicarbazides, J. App. Toxicol., 10 (1990) 59-64.
16. Saha, A., Roy, K., De, K. and Sengupta, C., QSAR with electrotopological state atom index: Part 3. Receptor binding affinity of oestrogens and non-steroidal oestrogen analogs, J. Indian Chem. Soc., 78 (2001) 92-97.
17. Singh, A.K., Development of QSAR models to predict oestrogenic, carcinogenic, and cancer protective effects of phytoestrogens, Cancer Invest., 19 (2001) 201-216.
18. Kier, L.B. and Hall, L.H., An electrotopological state index for atoms in molecules, Pharm. Res., 7 (1990) 801-807.
19. Hall, L.H., Mohney, B.K. and Kier, L.B., Comparison of electrotopological state indexes with molecular orbital parameters: Inhibition of MAO by hydrazides, Quant. Struct.Act. Relat., 12 (1993) 44-48.
20. Hall, L.H., Kier, L.B., Binding of salicylamides: QSAR analysis with electrotopological state indexes, Med. Res. Rev., 2 (1992) 497-502.
21. Maw, H.H. and Hall, L.H., E-state modeling of corticosteroids binding affinity validation of model for small dataset, J. Chem. Inf. Comput. Sci., 41 (2001) 1248-1254.
22. Grodnitzky, J.A. and Coats, J.R., QSAR evaluation of monoterpenoids' insecticidal activity, J. Agric. Food Chem., 50 (2002) 4576-4580.
23. Hall, L.H., Kier, L.B. and Brown, B.B., Molecular similarity based on novel atom-type electrotopological state indices, J. Chem. Inf. Comput. Sci., 35 (1995) 1074-1080.
24. Hall, L.H. and Kier, L.B., Electrotopological state indices for atom types: A novel combination of electronic, topological, and valence information, J. Chem. Inf. Comput. Sci., 35 (1995) 1039-1045.
25. Huuskonen, J., QSAR modelling with the electrotopological state indices: Predicting the toxicity of organic chemicals, Chemosphere, 50 (2003) 949-953.
26. Rose, K. and Hall, L.H., E-state modelling of fish toxicity independent of 3D structure information, SAR QSAR Environ. Res., 14 (2003) 113-129.
27. Hall, L.H. and Story, C.T., Boiling point and critical temperature of a heterogeneous dataset: QSAR with atom type electrotopological state indices using artificial neural networks, J. Chem. Inf. Comput. Sci., 36 (1996) 1004-1014.
28. Huuskonen, J., Rantanen, J. and Livingstone, D., Prediction of aqueous solubility for a diverse set of organic compounds based on atom-type electrotopological state indices, Eur. J. Med. Chem., 35 (2000) 1081-1088.
29. Hall, L.M., Hall, L.H. and Kier, L.B., QSAR modelling of β-lactam binding to human serum proteins, J. Comput. Aided Mol. Des., 17 (2003) 103-118.
30. Ghafourian, T. and Dearden, J.C., The use of atomic charges and orbital energies as hydrogen-bonding-donor parameters for QSAR studies: Comparison of MNDO, AM1 and PM3 methods, J. Pharm. Pharmacol., 52 (2000) 603-610.
31. Raevsky O.A., Fetisov, V.I., Trepalina, E.P., McFarland, J.W., Schaper, K.J., Quantitative estimation of drug absorption in humans for passively transported compounds on the basis of their physico-chemical parameters, Quant. Struct. Act. Relat., 19 (2000) 366-374.
32. Dearden, J.C. and Ghafourian, T., Hydrogen bonding parameters for QSAR: Comparison of indicator variables, hydrogen bond counts, molecular orbital and other parameters, J. Chem. Inf. Comput. Sci., 39 (1999) 231-235.
33. Liu, X., Wang, B., Huang, Z., Han, S. and Wang, L., Acute toxicity and quantitative structure-activity relationships of α-branched phenylsulfonyl acetates to Daphnia magna, Chemosphere, 50 (2003) 403-408.
34. Ghafourian, T. and Fooladi, S., The effect of structural QSAR parameters on skin penetration, Int. J. Pharm., 217 (2001) 1-11.
35. Wang, X., Sun, C., Wang, Y. and Wang, L., Quantitative structure-activity relationships for the inhibition toxicity to root elongation of Cucumis sativus of selected phenols and interspecies correlation with Tetrahymena pyriformis, Chemosphere, 46 (2002) 153-161.
36. Schmitt, H., Altenburger, R., Jastorff, B. and Schuurmann, G., Quantitative structure-activity analysis of the algae toxicity of nitroaromatic compounds, Chem. Res. Toxicol., 13 (2000) 441-450.
37. Alves, C.N., Pinheiro, J.C., Camargo, A.J., Ferreira, M.M.C. and da Silva, A.B.F., A structure-activity relationship study of HEPT-analog compounds with anti-HIV activity, J. Mol. Struct. (Theochem.), 530 (2000) 39-47.
38. Ghafourian, T. and Rashidi, M.R., Quantitative study of the structural requirements of phthalazine/quinazoline derivatives for interaction with human liver aldehyde oxidase, Chem. Pharm. Bull., 49 (2001) 1066-1071.
39. Richards, W.G., Quantum Chemistry, 2nd edn., London, Butterworths, 1983, pp. 153-155.
40. Cronin, M.T.D., Gregory, B.W. and Schultz, T.W., Quantitative structure-activity analyses of nitrobenzene toxicity to Tetrahymena pyriformis, Chem. Res. Toxicol., 11 (1998) 902-908.
41. Schultz, T.W., Structure-toxicity relationships for benzenes evaluated with Tetrahymena pyriformis, Chem. Res. Toxicol., 12 (1999) 1262-1267.
42. Karabunarliev, S., Mekenyan, O.G., Karcher, W., Russom, C.L. and Bradbury, S.P., Quantum-chemical descriptors for estimating the acute toxicity of substituted benzenes to the guppy (Poecilia reticulata) and the fathead minnow (Pimephales promelas), Quant. Struct. Act. Relat., 15 (1996) 311-320.
43. Cronin, M.T.D., Manga, N., Seward, J.R., Sinks, G.D. and Schultz, T.W., Parametrization of electrophilicity for the prediction of the toxicity of aromatic compounds, Chem. Res. Toxicol., 14 (2001) 1498-1505.
44. NAr electrophiles, Chem. Res. Toxicol., 10 (1997) 994-1000.
45. Bearden, A.P. and Schultz, T.W., Comparison of Tetrahymena and Pimephales toxicity based on mechanism of action, SAR QSAR Environ. Res., 9 (1998) 127-153.
46. Sheridan, P.L., Buckton, G. and Storey, D.E., The use of molecular-orbital indexes to predict the surface properties of pharmaceutical powders, Int. J. Pharm., 125 (1995) 141-149.
47. 50 values of epoxides to guppies, Sci. Total Environ., 109 (1991) 553-556.
48. Watkins, R.W., Lumley, J.A., Gill, E.L., Bishop, J.D., Langton, S.D., MacNicoll, A.D., Price, N.R. and Drew, M.G.B., Quantitative structure-activity relationships (QSAR) of cinnamic acid bird repellents, J. Chem. Ecol., 25 (1999) 2825-2845.
49. Gantchev, T.G., Ali, H., van Lier, J.E., Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives, J. Med. Chem., 37 (1994) 4164-4176.
50. Ali, H., Rousseau, J. and van Lier, J.E., Synthesis of A-ring fluorinated derivatives of (17a,20E/Z)-[125I]iodovinyl estradiols: Effect on receptor binding and receptor-mediated target tissue uptake, J. Med. Chem., 36 (1993) 3061-3072.
51. Ali, H., Rousseau, J., Ghaffari, M.A. and van Lier, J.E., Synthesis, receptor binding and tissue distribution of (17a,20E)- and (17a,20Z)-21-[125I] iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diol, J. Med. Chem., 31 (1988) 1946-1950.
52. Ali, H., Rousseau, J., Ghaffari, M.A. and van Lier, J.E., Synthesis, receptor binding and tissue distribution of 7a- and 11b-substituted (17a, 20E)- and (17a, 20Z)-21-[125I]iodo-19-norpregna-1,3,5(10),20-tetraene-3,17-diols, J. Med. Chem., 34 (1991) 854-860.
53. Ali, H., Rousseau, J. and van Lier, J.E., Synthesis, receptor binding and biodistribution of the Gem-21-chloro-21-iodovinylestradiol derivatives, J. Steroid Biochem. Mol. Biol., 46 (1993) 613-622.
54. Schneider, W. and Shyamala, G., Glucocorticoid receptors in primary culture of mouse mammary epithelial cells: characterization and modulation by prolactin and cortisol, Endocrinology, 116 (1982) 2656-2662.
55. Hall, L.H. and Kier, L.B., The kappa indices for modeling molecular shape and flexibility, In Devillers, J., Balaban, A.T. (Eds.), Topological Indices and Related Descriptors in QSAR and QSPR, Gordon and Breach, Reading, UK, 1999, pp. 455-489.
56. 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., Obstacles to the prediction of oestrogenicity from chemical structure: Assay-mediated metabolic transformation and the apparent promiscuous nature of the oestrogen receptor, Biochem. Pharm., 60 (2000) 1519-1530.
57. 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., Structure-activity relationships for a large diverse set of natural, synthetic, and environmental oestrogens, Chem. Res. Toxicol., 14 (2001) 280-294.
58. Roy, K., Chakraborty, S. and Saha, A., Exploring selectivity requirements for COX-2 versus COX-1 binding of 3,4-diaryloxazolones using E-state index, Bioorg. Med. Chem. Lett., 13 (2003) 3753-3757.
59. Lahsen, J., Schmidhammer, H., Spetea, M. and Rode, B.M., Quantitative electronic structure-activity relations: The influence of basis set selection on prediction quality, QSAR Comb. Sci., 22 (2003) 476-481.
60. Brauman, J.I. and Blair, L.K., Gas phase acidities of alcohols: Effects of alkyl groups, J. Am. Chem. Soc., 90 (1968) 6561-6562.
61. Deproft, F., Langenaeker, W. and Geerlings, P., Acidity of alkyl substituted alcohols - Are alkyl-groups electron-donating or electron-withdrawing, Tetrahedron, 51 (1995) 4021-4032.
62. Kubinyi, H., The quantitative analysis of structure-activity relationships, In Burger, A., Wolff, M.E (Eds.), Burger's Medicinal Chemistry and Drug Discovery, 5th edn., Vol. 1: Principles and Practice, Wiley, New York, 1995, pp. 497-571.
63. Hansch, C. and Leo, A., Substituent Constants for Correlation Analysis in Chemistry and Biology, John Wiley & Sons Inc., 1979, pp. 1-8, 49.