Three-dimensional quantitative structure-activity relationships for androgen receptor ligands

Toxicology and Applied Pharmacology

Volumn 137, Issue 2, 1996, Pages 219-227

  Waller, Chris L ^a   Juma, Booker W ^a   Earl Gray Jr , L ^a   Kelce, William R ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DICHLORO 2,2 BIS(4 CHLOROPHENYL)ETHYLENE; ANDROGEN RECEPTOR; ANDROSTANEDIOL; ANDROSTANOLONE; ANDROSTENEDIONE; CHLORPHENOTANE; CORTICOSTERONE; DIETHYLSTILBESTROL; ESTRADIOL; HORMONE; HYDROXYFLUTAMIDE; HYDROXYPROGESTERONE; LIGAND; LINURON; METHOXYCHLOR; METRIBOLONE; MIBOLERONE; PREGNENOLONE; PROCYMIDONE; PROGESTERONE; TESTOSTERONE; VINCLOZOLIN;

ARTICLE; MODEL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 0029874114     PISSN: 0041008X     EISSN: None     Source Type: Journal    
DOI: 10.1006/taap.1996.0075     Document Type: Article

References (16)

1. 1A receptor ligands by the method of comparative molecular field analysis. J. Comp. Chem. 14, 237-245.
2. Clark, M. D. C. R., and Van Opdenbosch, N. (1989). Validation of the general purpose Tripos 5.2 force field. J. Comput. Chem. 10, 982-1012.
3. Cramer, R. D., Patterson, D. E., and Bunce, J. D. (1988). Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 110, 5959-5967.
4. DePriest, S. A., Mayer, D., Naylor, C. B., and Marshall, G. R. (1993). 3D-QSAR of angiotensin-converting enzyme and thermolysin inhibitors: A comparison of CoMFA models based on deduced and experimentally determined active site geometries. J. Am. Chem. Soc. 115, 5372-5384.
5. Dewar, M. J. S., Zoebisch, E. G., Healy, E. F., and Stewart, J. J. P. (1985). AM1: A new general purpose quantum mechanical molecular model. J. Am. Chem. Soc. 107, 3902-3909.
6. Gantchev, T. G., Ali, H., and van Lier, J. E. (1994). Quantitative structure-activity relationships/comparative molecular field analysis (QSAR/CoMFA) for receptor-binding properties of halogenated estradiol derivatives. J. Med. Chem. 37, 4164-4176.
7. Goldstein, R. A., Katzenellenbogen, J. A., Luthey-Schulten, Z. A., Seielstad, D. A., and Wolynes, P. G. (1993). Three-dimensional model for the hormone binding domains of steroid receptors. Proc. Natl. Acad. Sci. USA 90, 9949-9953.
8. Kelce, W. R., Monosson, E., Gamcsik, M. P., Laws, S. C., and Gray, L. E. (1994). Environmental hormone disruptors: Evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Toxicol. Appl. Pharmacol. 126, 276-285.
9. Kelce, W. R., Stone, C. R., Laws, S. C., Gray, L. E., Kemppainen, J. A., and Wilson, E. W. (1995). Persistent DDT metabolite p,p′-DDE is a potent androgen receptor antagonist. Nature 375, 581-585.
10. Loughney, D. A., and Schwender, C. F. (1992). A comparison of progestin and androgen receptor binding using the CoMFA technique. J. Comput. Aided Mol. Des. 6, 569-581.
11. Lubahn, D. B., Joseph, D. R., Sar, M., Tan, J. A., Higgs, H. N., Larson, R. E., French, F. S., and Wilson, E. M. (1988). The human androgen receptor: Complementary deoxyribonucleic acid cloning, sequence analysis and gene expression in prostate. Mol. Endocrinol. 2, 1265-1275.
12. McKinney, J. D., and Waller, C. L. (1994). Polychlorinated biphenyls as hormonally active structural analogs. Environ. Health Perspect. 102, 290-297.
13. Thomas, B. F., Compton, D. R., Martin, B. R., and Semus, S. F. (1991). Modeling the cannabinoid receptor: A three-dimensional quantitative structure-activity analysis. Mol. Pharmacol. 40, 656-665.
14. Waller, C. L., and McKinney, J. D. (1995a). Three-dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: Model validation and Ah receptor characterization. Chem. Res. Toxicol. 8, 847-858.
15. Waller, C. L., Minor, D. L., and McKinney, J. D. (1995b). Examination of the estrogen-receptor binding affinities of polychlorinated hydroxybiphenyls using three-dimensional quantitative structure-activity relationships. Environ. Health Perspect. 103, 702-707.
16. Waller, C. L., Oprea, T. I., Giolitti, A., and Marshall, G. R. (1994). 3D-QSAR of human immunodeficiency virus (I) protease inhibitors. I. A CoMFA study employing experimentally determined alignment rules. J. Med. Chem. 36, 4152-4160.