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Volumn 111, Issue 4, 2003, Pages 545-552

Interaction of organophosphate pesticides and related compounds with the androgen receptor

Author keywords

Androgen receptor; Fenitrothion; HepG2 cells; Homology model; Organophosphates; Structure activity relationships

Indexed keywords

ALKYL GROUP; ANDROGEN RECEPTOR; ANTIANDROGEN; ENVIRONMENTAL CHEMICAL; FENITROTHION; FLUTAMIDE; HORMONE ANTAGONIST; HYDROXYFLUTAMIDE; LINURON; LUCIFERASE; ORGANOPHOSPHATE PESTICIDE; PARATHION; PARATHION METHYL; PHENYL GROUP;

EID: 0038408658     PISSN: 00916765     EISSN: None     Source Type: Journal    
DOI: 10.1289/ehp.5671     Document Type: Review
Times cited : (48)

References (49)
  • 1
    • 0031059270 scopus 로고    scopus 로고
    • The estradiol pharmacophore: Ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site
    • Anstead GM, Carlson KE, Katzenellenbogen JA. 1997. The estradiol pharmacophore: ligand structure-estrogen receptor binding affinity relationships and a model for the receptor binding site. Steroids 62:268-303.
    • (1997) Steroids , vol.62 , pp. 268-303
    • Anstead, G.M.1    Carlson, K.E.2    Katzenellenbogen, J.A.3
  • 2
    • 17744378148 scopus 로고    scopus 로고
    • Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function
    • Buchanan G, Yang M, Harris HM, Nahm HS, Han G, Moore N, et al. 2001. Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function. Mol Endocrin 15:46-56.
    • (2001) Mol. Endocrin. , vol.15 , pp. 46-56
    • Buchanan, G.1    Yang, M.2    Harris, H.M.3    Nahm, H.S.4    Han, G.5    Moore, N.6
  • 4
    • 0031039480 scopus 로고    scopus 로고
    • Functional in vivo interaction between the amino-terminal, transactivation domain and the ligand binding domain of the androgen receptor
    • Doesburg P, Kuil CW, Berrevoets CA, Steketee K, Faber PW, Mulder E, et al. 1997. Functional in vivo interaction between the amino-terminal, transactivation domain and the ligand binding domain of the androgen receptor. Biochemistry 36:1052-1064.
    • (1997) Biochemistry , vol.36 , pp. 1052-1064
    • Doesburg, P.1    Kuil, C.W.2    Berrevoets, C.A.3    Steketee, K.4    Faber, P.W.5    Mulder, E.6
  • 6
    • 0035085038 scopus 로고    scopus 로고
    • Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens
    • Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W, et al. 2001. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem Res Toxicol 14:280-294.
    • (2001) Chem. Res. Toxicol. , vol.14 , pp. 280-294
    • Fang, H.1    Tong, W.2    Shi, L.M.3    Blair, R.4    Perkins, R.5    Branham, W.6
  • 9
    • 0342646942 scopus 로고    scopus 로고
    • The estrogenic and antiandrogenic pesticide methoxychlor alters the reproductive tract and behavior without affecting pituitary size or LH and prolactin secretion in male rats
    • Gray LE Jr, Ostby J, Cooper RL, Kelce WR. 1999a. The estrogenic and antiandrogenic pesticide methoxychlor alters the reproductive tract and behavior without affecting pituitary size or LH and prolactin secretion in male rats. Toxicol Ind Health 15:37-47.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 37-47
    • Gray L.E., Jr.1    Ostby, J.2    Cooper, R.L.3    Kelce, W.R.4
  • 10
    • 0343962125 scopus 로고    scopus 로고
    • Environmental antiandrogens: Low doses of the fungicide vinclozolin alter sexual differentiation of the male rat
    • Gray LE Jr, Ostby J, Monosson E, Kelce WR. 1999b. Environmental antiandrogens: low doses of the fungicide vinclozolin alter sexual differentiation of the male rat. Toxicol Ind Health 15:48-64.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 48-64
    • Gray L.E., Jr.1    Ostby, J.2    Monosson, E.3    Kelce, W.R.4
  • 11
    • 0343090362 scopus 로고    scopus 로고
    • Administration of potentially antiandrogenic pesticides (procymidone, linuron, iprodione, chlozolinate, p,p′-DDE, and ketoconazole) and toxic substances (dibutyl- and diethylhexyl phthalate, PCB 169, and ethane dimethane sulphonate) during sexual differentiation produces diverse profiles of reproductive malformations in the male rat
    • Gray LE Jr, Wolf C, Lambright C, Mann P, Price M, Cooper RL, et al. 1999c. Administration of potentially antiandrogenic pesticides (procymidone, linuron, iprodione, chlozolinate, p,p′-DDE, and ketoconazole) and toxic substances (dibutyl- and diethylhexyl phthalate, PCB 169, and ethane dimethane sulphonate) during sexual differentiation produces diverse profiles of reproductive malformations in the male rat. Toxicol Ind Health 15:94-118.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 94-118
    • Gray L.E., Jr.1    Wolf, C.2    Lambright, C.3    Mann, P.4    Price, M.5    Cooper, R.L.6
  • 12
    • 0002488167 scopus 로고
    • The steroid hormone receptor superfamily-molecular mechanisms of action
    • (Weintraub B, ed). New York:Raven Press
    • Ing NH, O'Malley BW. 1995. The steroid hormone receptor superfamily-molecular mechanisms of action. In: Molecular Endoclinology: Basic Concepts and Clinical Correlations (Weintraub B, ed). New York:Raven Press, 195-215.
    • (1995) Molecular Endoclinology: Basic Concepts and Clinical Correlations , pp. 195-215
    • Ing, N.H.1    O'Malley, B.W.2
  • 13
    • 0028228821 scopus 로고
    • Environmental hormone disruptors: Evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites
    • Kelce WR, Monosson E, Gamcsik MP, Laws SC, Gray LE Jr. 1994. Environmental hormone disruptors: evidence that vinclozolin developmental toxicity is mediated by antiandrogenic metabolites. Toxicol Appl Pharmacol 126:276-285.
    • (1994) Toxicol. Appl. Pharmacol. , vol.126 , pp. 276-285
    • Kelce, W.R.1    Monosson, E.2    Gamcsik, M.P.3    Laws, S.C.4    Gray L.E., Jr.5
  • 16
    • 0027032097 scopus 로고
    • A comparison of progestin and androgen receptor binding using the CoMFA technique
    • Loughney DA, Schwender CF. 1992. A comparison of progestin and androgen receptor binding using the CoMFA technique. J Comput Aided Mol Des 6:569-581.
    • (1992) J. Comput. Aided Mol. Des. , vol.6 , pp. 569-581
    • Loughney, D.A.1    Schwender, C.F.2
  • 17
    • 0031752451 scopus 로고    scopus 로고
    • Inhibition of androgen receptor-dependent transcriptional activity by DDT isomers and methoxychlor in HepG2 human hepatoma cells
    • Maness SC, McDonnell DP, Gaido KW. 1998. Inhibition of androgen receptor-dependent transcriptional activity by DDT isomers and methoxychlor in HepG2 human hepatoma cells. Toxicol Appl Pharmacol 151:135-142.
    • (1998) Toxicol. Appl. Pharmacol. , vol.151 , pp. 135-142
    • Maness, S.C.1    McDonnell, D.P.2    Gaido, K.W.3
  • 18
    • 0035942522 scopus 로고    scopus 로고
    • Homology modeling using multiple molecular dynamics simulations and docking studies of the human androgen receptor ligand binding domain bound to testosterone and nonsteroidal ligands
    • Marhefka CA, Moore BM, Bishop TC, Kirkovsky L, Mukherjee A, Dalton J, et al. 2001. Homology modeling using multiple molecular dynamics simulations and docking studies of the human androgen receptor ligand binding domain bound to testosterone and nonsteroidal ligands. J Med Chem 44:1729-1740.
    • (2001) J. Med. Chem. , vol.44 , pp. 1729-1740
    • Marhefka, C.A.1    Moore, B.M.2    Bishop, T.C.3    Kirkovsky, L.4    Mukherjee, A.5    Dalton, J.6
  • 20
    • 0034714276 scopus 로고    scopus 로고
    • Structural evidence for ligand specificity in the binding domain of the human androgen receptor. Implications for pathogenic gene mutations
    • Matias PM, Donner P, Coelho R, Thomaz M, Peixoto C, Macedo S, et al. 2000. Structural evidence for ligand specificity in the binding domain of the human androgen receptor. Implications for pathogenic gene mutations. J Biol Chem 275:26164-26171.
    • (2000) J. Biol. Chem. , vol.275 , pp. 26164-26171
    • Matias, P.M.1    Donner, P.2    Coelho, R.3    Thomaz, M.4    Peixoto, C.5    Macedo, S.6
  • 22
    • 0028344926 scopus 로고
    • Polychlorinated biphenyls as hormonally active structural analogues
    • McKinney JD, Waller CL. 1994. Polychlorinated biphenyls as hormonally active structural analogues. Environ Health Perspect 102:290-297.
    • (1994) Environ. Health Perspect. , vol.102 , pp. 290-297
    • McKinney, J.D.1    Waller, C.L.2
  • 23
    • 0031458685 scopus 로고    scopus 로고
    • COREPA: A new approach for the elucidation of Common Reactivity Patterns of chemicals. I. Stereoelectronic requirements for androgen receptor binding
    • Mekenyan OG, Ivanov JM, Karabunarliev SH, Bradbury SP, Ankley GT, Karcher W. 1997. COREPA: A new approach for the elucidation of Common Reactivity Patterns of chemicals. I. Stereoelectronic requirements for androgen receptor binding. Environ Sci Technol 31:3702-3711.
    • (1997) Environ. Sci. Technol. , vol.31 , pp. 3702-3711
    • Mekenyan, O.G.1    Ivanov, J.M.2    Karabunarliev, S.H.3    Bradbury, S.P.4    Ankley, G.T.5    Karcher, W.6
  • 24
    • 0033360298 scopus 로고    scopus 로고
    • Peripubertal exposure to the antiandrogenic fungicide, vinclozolin, delays puberty, inhibits the development of androgen-dependent tissues, and alters androgen receptor function in the male rat
    • Monosson E, Kelce WR, Lambright C, Ostby J, Gray LE Jr. 1999. Peripubertal exposure to the antiandrogenic fungicide, vinclozolin, delays puberty, inhibits the development of androgen-dependent tissues, and alters androgen receptor function in the male rat. Toxicol Ind Health 15:65-79.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 65-79
    • Monosson, E.1    Kelce, W.R.2    Lambright, C.3    Ostby, J.4    Gray L.E., Jr.5
  • 25
    • 84948047740 scopus 로고
    • Studies on the organophosphorus insecticides. VI. Development of new low toxic phosphorus insecticides
    • Nishizawa Y, Nakagawa M, Suzuki H, Sakamoto H, Mizutani T. 1961. Studies on the organophosphorus insecticides. VI. Development of new low toxic phosphorus insecticides. Agricul Biol Chem 25:597-610.
    • (1961) Agricul. Biol. Chem. , vol.25 , pp. 597-610
    • Nishizawa, Y.1    Nakagawa, M.2    Suzuki, H.3    Sakamoto, H.4    Mizutani, T.5
  • 26
    • 0033363929 scopus 로고    scopus 로고
    • The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro
    • Ostby J, Kelce WR, Lambright C, Wolf CJ, Mann P, Gray LE Jr. 1999. The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro. Toxicol Ind Health 15:80-93.
    • (1999) Toxicol. Ind. Health , vol.15 , pp. 80-93
    • Ostby, J.1    Kelce, W.R.2    Lambright, C.3    Wolf, C.J.4    Mann, P.5    Gray L.E., Jr.6
  • 27
    • 0033198735 scopus 로고    scopus 로고
    • Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist
    • Pike ACW, Brzozowski AM, Hubbard RE, Bonn T, Thorsell AG, Engstrom O, et al. 1999. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO J 18:4608-4618.
    • (1999) EMBO J. , vol.18 , pp. 4608-4618
    • Pike, A.C.W.1    Brzozowski, A.M.2    Hubbard, R.E.3    Bonn, T.4    Thorsell, A.G.5    Engstrom, O.6
  • 28
    • 0034604620 scopus 로고    scopus 로고
    • Specific recognition of androgens by their nuclear receptor. A structure-function study
    • Poujol N, Wurtz JM, Tahiri B, Lumbroso S, Nicolas JC, Moras D, et al. 2000. Specific recognition of androgens by their nuclear receptor. A structure-function study. J Biol Chem 275:24022-24031.
    • (2000) J. Biol. Chem. , vol.275 , pp. 24022-24031
    • Poujol, N.1    Wurtz, J.M.2    Tahiri, B.3    Lumbroso, S.4    Nicolas, J.C.5    Moras, D.6
  • 29
    • 0029643780 scopus 로고
    • Crystal structure of the RAR-gamma ligand-binding domain bound to all-trans retinoic acid
    • Renaud JP, Rochel N, Ruff M, Vivat V, Chambon P, Gronemeyer H, et al. 1995. Crystal structure of the RAR-gamma ligand-binding domain bound to all-trans retinoic acid, Nature 378:681-689.
    • (1995) Nature , vol.378 , pp. 681-689
    • Renaud, J.P.1    Rochel, N.2    Ruff, M.3    Vivat, V.4    Chambon, P.5    Gronemeyer, H.6
  • 30
    • 0035942197 scopus 로고    scopus 로고
    • Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone
    • Sack JS, Kish KF, Wang C, Attar RM, Kiefer SE, An Y, et al. 2001. Crystallographic structures of the ligand-binding domains of the androgen receptor and its T877A mutant complexed with the natural agonist dihydrotestosterone. Proc Natl Acad Sci USA 98:4904-4909.
    • (2001) Proc. Natl. Acad. Sci. USA , vol.98 , pp. 4904-4909
    • Sack, J.S.1    Kish, K.F.2    Wang, C.3    Attar, R.M.4    Kiefer, S.E.5    An, Y.6
  • 31
    • 0030637651 scopus 로고    scopus 로고
    • Organochlorine exposure and risk for breast cancer
    • Safe SH, Zacharewski T. 1997. Organochlorine exposure and risk for breast cancer. Prog Clin Biol Res 396:133-145.
    • (1997) Prog. Clin. Biol. Res. , vol.396 , pp. 133-145
    • Safe, S.H.1    Zacharewski, T.2
  • 32
    • 0034121290 scopus 로고    scopus 로고
    • Androgen receptor antagonists (antiandrogens): Structure activity relationships
    • Singh MS, Gauthier S, Labrie F. 2000. Androgen receptor antagonists (antiandrogens): structure activity relationships. Curr Med Chem 7:211-247.
    • (2000) Curr. Med. Chem. , vol.7 , pp. 211-247
    • Singh, M.S.1    Gauthier, S.2    Labrie, F.3
  • 33
    • 84988129057 scopus 로고    scopus 로고
    • Optimization of parameters for semiempirical methods. I. Method
    • Stewart JJP. 1998. Optimization of parameters for semiempirical methods. I. Method. J Comp Chem 10:209-220.
    • (1998) J. Comp. Chem. , vol.10 , pp. 209-220
    • Stewart, J.J.P.1
  • 36
    • 0032568527 scopus 로고    scopus 로고
    • Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains
    • Tanenbaum DM, Wang Y, Williams SP, Sigler PB. 1998. Crystallographic comparison of the estrogen and progesterone receptor's ligand binding domains. Proc Natl Acad Sci USA 95:5998-6003.
    • (1998) Proc. Natl. Acad. Sci. USA , vol.95 , pp. 5998-6003
    • Tanenbaum, D.M.1    Wang, Y.2    Williams, S.P.3    Sigler, P.B.4
  • 37
    • 0033152164 scopus 로고    scopus 로고
    • Selection for androgen receptor mutations in prostate cancers treated with androgen antagonist
    • Taplin ME, Bubley GJ, Ko YJ, Small EJ, Upton M, Rajeshkumar B, et al. 1999. Selection for androgen receptor mutations in prostate cancers treated with androgen antagonist. Cancer Res 59:2511-2515.
    • (1999) Cancer Res. , vol.59 , pp. 2511-2515
    • Taplin, M.E.1    Bubley, G.J.2    Ko, Y.J.3    Small, E.J.4    Upton, M.5    Rajeshkumar, B.6
  • 38
  • 39
    • 0031410762 scopus 로고    scopus 로고
    • Quantitative structure-activity relationships (QSARs) for estrogen binding to the estrogen receptor: Predictions across species
    • Tong W, Perkins R, Strelitz R, Collantes ER, Keenan S, Welsh WJ, et al. 1997a. Quantitative structure-activity relationships (QSARs) for estrogen binding to the estrogen receptor: predictions across species. Environ Health Perspect 105:1116-1124.
    • (1997) Environ. Health Perspect. , vol.105 , pp. 1116-1124
    • Tong, W.1    Perkins, R.2    Strelitz, R.3    Collantes, E.R.4    Keenan, S.5    Welsh, W.J.6
  • 40
    • 0030795434 scopus 로고    scopus 로고
    • QSAR models for binding of estrogenic compounds to estrogen receptor alpha and beta subtypes
    • Tong W, Perkins R, Xing L, Welsh WJ, Sheehan DM. 1997b. QSAR models for binding of estrogenic compounds to estrogen receptor alpha and beta subtypes. Endocrinology 138:4022-4025.
    • (1997) Endocrinology , vol.138 , pp. 4022-4025
    • Tong, W.1    Perkins, R.2    Xing, L.3    Welsh, W.J.4    Sheehan, D.M.5
  • 41
    • 0032109698 scopus 로고    scopus 로고
    • Evaluation of quantitative structure-activity relationship methods for large-scale prediction of chemicals binding to the estrogen receptor
    • Tong W, Lowis DR, Perkins R, Chen Y, Welsh WJ, Goddette DW, et al. 1998. Evaluation of quantitative structure-activity relationship methods for large-scale prediction of chemicals binding to the estrogen receptor. J Chem Inf Comput Sci 38:669-677.
    • (1998) J. Chem. Inf. Comput. Sci. , vol.38 , pp. 669-677
    • Tong, W.1    Lowis, D.R.2    Perkins, R.3    Chen, Y.4    Welsh, W.J.5    Goddette, D.W.6
  • 42
    • 0023893448 scopus 로고
    • Nonsteroidal antiandrogens. Synthesis and structure-activity relationships of 3-substituted derivatives of 2-hydroxypropionanilides
    • Tucker H, Crook JW, Chesterson GJ. 1988. Nonsteroidal antiandrogens. Synthesis and structure-activity relationships of 3-substituted derivatives of 2-hydroxypropionanilides. J Med Chem 31:954-959.
    • (1988) J. Med. Chem. , vol.31 , pp. 954-959
    • Tucker, H.1    Crook, J.W.2    Chesterson, G.J.3
  • 43
    • 0029874114 scopus 로고    scopus 로고
    • Three-dimensional quantitative structure-activity relationships for androgen receptor ligands
    • Waller CL, Juma BW, Gray LE Jr, Kelce WR. 1996a. Three-dimensional quantitative structure-activity relationships for androgen receptor ligands. Toxicol Appl Pharmacol 137:219-227.
    • (1996) Toxicol. Appl. Pharmacol. , vol.137 , pp. 219-227
    • Waller, C.L.1    Juma, B.W.2    Gray L.E., Jr.3    Kelce, W.R.4
  • 45
    • 0028322347 scopus 로고
    • Molecular modeling of steroidal estrogens: Novel conformations and their role in biological activity
    • Wiese TE, Brooks SC. 1994. Molecular modeling of steroidal estrogens: novel conformations and their role in biological activity. J Steroid Biochem Mol Biol 50:61-73.
    • (1994) J. Steroid Biochem. Mol. Biol. , vol.50 , pp. 61-73
    • Wiese, T.E.1    Brooks, S.C.2
  • 46
    • 0028801268 scopus 로고
    • Environmental organochlorine exposure as a potential etiologic factor in breast cancer
    • Wolff MS, Toniolo PG. 1995. Environmental organochlorine exposure as a potential etiologic factor in breast cancer. Environ Health Perspect 103(suppl 7):141-145.
    • (1995) Environ. Health Perspect , vol.103 , Issue.SUPPL. 7 , pp. 141-145
    • Wolff, M.S.1    Toniolo, P.G.2
  • 47
    • 0029123855 scopus 로고
    • Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamide
    • Wong C, Kelce WR, Sar M, Wilson EM. 1995. Androgen receptor antagonist versus agonist activities of the fungicide vinclozolin relative to hydroxyflutamide. J Biol Chem 270:19998-20003.
    • (1995) J. Biol. Chem. , vol.270 , pp. 19998-20003
    • Wong, C.1    Kelce, W.R.2    Sar, M.3    Wilson, E.M.4
  • 49
    • 0025644325 scopus 로고
    • A mutation in the ligand binding domain of the androgen receptor of human LNCaP cells affects steroid binding characteristics and response to anti-androgens
    • Veldscholte J, Ris-Stalpers C, Kuiper GG, Jenster G, Berrevoets C, Claassen E, et al. 1990. A mutation in the ligand binding domain of the androgen receptor of human LNCaP cells affects steroid binding characteristics and response to anti-androgens. Biochem Biophys Res Commun 173:534-540.
    • (1990) Biochem. Biophys. Res. Commun. , vol.173 , pp. 534-540
    • Veldscholte, J.1    Ris-Stalpers, C.2    Kuiper, G.G.3    Jenster, G.4    Berrevoets, C.5    Claassen, E.6


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