Enantioselective recognition of mono-demethylated methoxychlor metabolites by the estrogen receptor

Chemosphere

Volumn 54, Issue 8, 2004, Pages 1273-1276

  Miyashita, Masahiro ^a,b   Shimada, Takahiro ^a,b   Nakagami, Shizuka ^b   Kurihara, Norio ^c   Miyagawa, Hisashi ^a   Akamatsu, Miki ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^c Japan Radioisotope Association   (Japan)

Author keywords

Endocrine disruption; Estrogenic activity; Hydrogen bond; Metabolic activation; Receptor binding

Indexed keywords

BINDING ENERGY; CHEMICAL ACTIVATION; ETHANE; METABOLITES;

CHIRAL COMPOUNDS; ESTROGENIC ACTIVITY;

HORMONES;

BISHYDROXYMETHOXYCHLOR; CARBON; ESTROGEN; ESTROGEN RECEPTOR; HYDROXYMETHOXYCHLOR; METHOXYCHLOR; METHOXYCHLOR DERIVATIVE; UNCLASSIFIED DRUG;

ESTROGENIC COMPOUND; METABOLITE;

ARTICLE; CHIRALITY; ENANTIOMER; ENANTIOSELECTIVITY; ESTROGEN ACTIVITY; HUMAN; IC 50; IN VITRO STUDY; MEASUREMENT; METABOLITE; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NONHUMAN; POLLUTANT; RACEMIC MIXTURE; RECEPTOR BINDING;

EID: 1642435400     PISSN: 00456535     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemosphere.2003.10.035     Document Type: Article

References (21)

1. Anstead, G.M., Carlson, K.E., 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.
2. Brzozowski, A.M., Pike, A.C., Dauter, Z., Hubbard, R.E., Bonn, T., Engstrom, O., Ohman, L., Greene, G.L., Gustafsson, J.A., Carlquist, M., 1997. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389, 753-758.
3. Bulger, W.H., Muccitelli, R.M., Kupfer, D., 1978. Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites. Role of hepatic mono-oxygenase in methoxychlor activation. Biochem. Pharmacol. 27, 2417-2423.
4. Colborn, T., vom Saal, F.S., Soto, A.M., 1993. Developmental effects of endocrine-disrupting chemicals in wildlife and humans. Environ. Health Perspect. 101, 378-384.
5. Fang, H., Tong, W., Shi, L.M., Blair, R., Perkins, R., Branham, W., Hass, B.S., Xie, Q., Dial, S.L., Moland, C.L., Sheehan, D.M., 2001. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem. Res. Toxicol. 14, 280-294.
6. Gust, R., Keilitz, R., Schmidt, K., von Rauch, M., 2002. (4R,5S)/(4S,5R)-4,5-bis(4-hydroxyphenyl)-2-imidazolines: ligands for the estrogen receptor with a novel binding mode. J. Med. Chem. 45, 3356-3365.
7. Hoekstra, P.F., Burnison, B.K., Neheli, T., Muir, D.C., 2001. Enantiomer-specific activity of o,p′-DDT with the human estrogen receptor. Toxicol. Lett. 125, 75-81.
8. Hu, Y., Kupfer, D., 2002. Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes p450 (p450s): major differences in selective enantiomer formation by various p450 isoforms. Drug Metab. Dispos. 30, 1329-1336.
9. 3]methoxychlor and related deuterium-labeled compounds. Agric. Biol. Chem. 50, 1331-1332.
10. Kishimoto, D., Oku, A., Kurihara, N., 1995. Enantiotopic selectivity of cytochrome p450-catalyzed oxidative demethylation of methoxychlor-alteration of selectivity depending on isozymes and substrate concentrations. Pest. Biochem. Phys. 51, 12-19.
11. Koda, T., Soya, Y., Negishi, H., Shiraishi, F., Morita, M., 2002. Improvement of a sensitive enzyme-linked immunosorbent assay for screening estrogen receptor binding activity. Environ. Toxicol. Chem. 21, 2536-2541.
12. Korach, K.S., Chae, K., Levy, L.A., Duax, W.L., Sarver, P.J., 1989. Diethylstilbestrol metabolites and analogs. Stereochemical probes for the estrogen receptor binding site. J. Biol. Chem. 264, 5642-5647.
13. Krishnan, A.V., Stathis, P., Permuth, S.F., Tokes, L., Feldman, D., 1993. Bisphenol-A: an estrogenic substance is released from polycarbonate flasks during autoclaving. Endocrinology 132, 2279-2286.
14. McBlain, W.A., 1987. The levo enantiomer of o,p′-DDT inhibits the binding of 17β-estradiol to the estrogen receptor. Life Sci. 40, 215-221.
15. Mueller, S.O., Hall, J.M., Swope, D.L., Pedersen, L.C., Korach, K.S., 2003. Molecular determinants of the stereoselectivity of agonist activity of estrogen receptors (ER) α and β. J. Biol. Chem. 278, 12255-12262.
16. 3H]estradiol binding to rat uterine receptor. Biochem. Pharmacol. 23, 447-451.
17. Ousterhout, J., Struck, R.F., Nelson, J.A., 1981. Estrogenic activities of methoxychlor metabolites. Biochem. Pharmacol. 30, 2869-2871.
18. Shiau, A.K., Barstad, D., Loria, P.M., Cheng, L., Kushner, P.J., Agard, D.A., Greene, G.L., 1998. The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 95, 927-937.
19. Shiau, A.K., Barstad, D., Radek, J.T., Meyers, M.J., Nettles, K.W., Katzenellenbogen, B.S., Katzenellenbogen, J.A., Agard, D.A., Greene, G.L., 2002. Structural characterization of a subtype-selective ligand reveals a novel mode of estrogen receptor antagonism. Nat. Struct. Biol. 9, 359-364.
20. Soto, A.M., Justicia, H., Wray, J.W., Sonnenschein, C., 1991. p-Nonyl-phenol: an estrogenic xenobiotic released from "modified" polystyrene. Environ. Health Perspect. 92, 167-173.
21. Uchida, M., Naka, H., Irie, Y., Fujita, T., Nakajima, M., 1974. Insecticidal and neuroexciting actions of DDT analogs. Pest. Biochem. Physiol. 4, 451-455.