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Volumn 30, Issue 12, 2002, Pages 1329-1336

Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes P450 (P450s): Major differences in selective enantiomer formation by various P450 isoforms

Author keywords

[No Author keywords available]

Indexed keywords

CYTOCHROME P450; METHOXYCHLOR; PESTICIDE; INSECTICIDE; ISOENZYME;

EID: 0036892632     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: 10.1124/dmd.30.12.1329     Document Type: Article
Times cited : (42)

References (29)
  • 2
    • 0021987828 scopus 로고
    • Role of hepatic monooxygenases in generating estrogenic metabolites from methoxychlor and from its identified contaminants
    • Bulger WH, Feil VJ, and Kupfer D (1985) Role of hepatic monooxygenases in generating estrogenic metabolites from methoxychlor and from its identified contaminants. Mol Pharmacol 27:115-124.
    • (1985) Mol Pharmacol , vol.27 , pp. 115-124
    • Bulger, W.H.1    Feil, V.J.2    Kupfer, D.3
  • 3
    • 0018009080 scopus 로고
    • Interactions of methoxychlor, methoxychlor base-soluble contaminant and 2,2-bis-(p-hydroxy phenyl)-1,1,1-trichloroethane with rat uterine estrogen receptor
    • Bulger WH, Muccitelli RM, and Kupfer D (1978a) Interactions of methoxychlor, methoxychlor base-soluble contaminant and 2,2-bis-(p-hydroxy phenyl)-1,1,1-trichloroethane with rat uterine estrogen receptor. J Toxicol Environ Health 4:881-893.
    • (1978) J Toxicol Environ Health , vol.4 , pp. 881-893
    • Bulger, W.H.1    Muccitelli, R.M.2    Kupfer, D.3
  • 4
    • 0018078757 scopus 로고
    • Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites. Role of hepatic mono-oxygenases in methoxychlor activation
    • Bulger WH, Muccitelli RM, and Kupfer D (1978b) Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites. Role of hepatic mono-oxygenases in methoxychlor activation. Biochem Pharmacol 27:2417-2423.
    • (1978) Biochem Pharmacol , vol.27 , pp. 2417-2423
    • Bulger, W.H.1    Muccitelli, R.M.2    Kupfer, D.3
  • 6
    • 0030728930 scopus 로고    scopus 로고
    • Tissue distribution and quantitative analysis of estrogen receptor-alpha (ERalpha) and estrogen receptor-beta (ERbeta) messenger ribonucleic acid in the wild-type and ERalpha-knockout mouse
    • Couse JF, Lindzey J, Grandien K, Gustafsson JA, and Korach KS (1997) Tissue distribution and quantitative analysis of estrogen receptor-alpha (ERalpha) and estrogen receptor-beta (ERbeta) messenger ribonucleic acid in the wild-type and ERalpha-knockout mouse. Endocrinology 138:4613-4621.
    • (1997) Endocrinology , vol.138 , pp. 4613-4621
    • Couse, J.F.1    Lindzey, J.2    Grandien, K.3    Gustafsson, J.A.4    Korach, K.S.5
  • 7
    • 0030797394 scopus 로고    scopus 로고
    • Methoxychlor as a model for environmental estrogens
    • Cummings AM (1997) Methoxychlor as a model for environmental estrogens. Crit Rev Toxicol 27:367-379.
    • (1997) Crit Rev Toxicol , vol.27 , pp. 367-379
    • Cummings, A.M.1
  • 8
    • 0024573314 scopus 로고
    • Antifertility effect of methoxychlor in female rats: Dose- and time-dependent blockade of pregnancy
    • Cummings AM and Gray LE Jr (1989) Antifertility effect of methoxychlor in female rats: Dose- and time-dependent blockade of pregnancy. Toxicol Appl Pharmacol 97:454-462.
    • (1989) Toxicol Appl Pharmacol , vol.97 , pp. 454-462
    • Cummings, A.M.1    Gray L.E., Jr.2
  • 9
    • 0027351313 scopus 로고
    • Effect of methoxychlor on ovarian steroidogenesis: Role in early pregnancy loss
    • Cummings AM and Laskey J (1993) Effect of methoxychlor on ovarian steroidogenesis: Role in early pregnancy loss. Reprod Toxicol 7:17-23.
    • (1993) Reprod Toxicol , vol.7 , pp. 17-23
    • Cummings, A.M.1    Laskey, J.2
  • 10
    • 0027946075 scopus 로고
    • Metabolism of the proestrogenic pesticide methoxychlor by hepatic P450 monooxygenases in rats and humans. Dual pathways involving novel ortho ring-hydroxylation by CYP2B
    • Dehal SS and Kupfer D (1994) Metabolism of the proestrogenic pesticide methoxychlor by hepatic P450 monooxygenases in rats and humans. Dual pathways involving novel ortho ring-hydroxylation by CYP2B. Drug Metab Dispos 22:937-946.
    • (1994) Drug Metab Dispos , vol.22 , pp. 937-946
    • Dehal, S.S.1    Kupfer, D.2
  • 11
    • 0035912903 scopus 로고    scopus 로고
    • Tissue-specific expression of human ERalpha and ERbeta in the male
    • Denger S, Reid G, Brand H, Kos M, and Gannon F (2001) Tissue-specific expression of human ERalpha and ERbeta in the male. Mol Cell Endocrinol 178:155-160.
    • (2001) Mol Cell Endocrinol , vol.178 , pp. 155-160
    • Denger, S.1    Reid, G.2    Brand, H.3    Kos, M.4    Gannon, F.5
  • 12
    • 0033802882 scopus 로고    scopus 로고
    • Interaction of methoxychlor and related compounds with estrogen receptor alpha and beta and androgen receptor: Structure-activity studies
    • Gaido KW, Maness SC, McDonnell DP, Dehal SS, Kupfer D, and Safe S (2000) Interaction of methoxychlor and related compounds with estrogen receptor alpha and beta and androgen receptor: Structure-activity studies. Mol Pharmacol 58:852-858.
    • (2000) Mol Pharmacol , vol.58 , pp. 852-858
    • Gaido, K.W.1    Maness, S.C.2    McDonnell, D.P.3    Dehal, S.S.4    Kupfer, D.5    Safe, S.6
  • 13
    • 0011745446 scopus 로고
    • National Research Council of Canada; Associate Committee on Scientific Criteria for Environmental Quality. Publication NRCC No. 14102, Ottawa, Canada
    • Gardner DR and Bailey JR (1975) Methoxychlor: Its Effects on Environmental Quality. National Research Council of Canada; Associate Committee on Scientific Criteria for Environmental Quality. Publication NRCC No. 14102, Ottawa, Canada.
    • (1975) Methoxychlor: Its Effects on Environmental Quality
    • Gardner, D.R.1    Bailey, J.R.2
  • 14
    • 0024232259 scopus 로고
    • Methoxychlor induces estrogen-like alterations of behavior and the reproductive tract in the female rat and hamster: Effects on sex behavior, running wheel activity and uterine morphology
    • Gray LE Jr, Ostby JS, Ferrell JM, Sigmon ER, and Goldman JM (1988) Methoxychlor induces estrogen-like alterations of behavior and the reproductive tract in the female rat and hamster: Effects on sex behavior, running wheel activity and uterine morphology. Toxicol Appl Pharmacol 96:525-540.
    • (1988) Toxicol Appl Pharmacol , vol.96 , pp. 525-540
    • Gray L.E., Jr.1    Ostby, J.S.2    Ferrell, J.M.3    Sigmon, E.R.4    Goldman, J.M.5
  • 15
    • 0036707621 scopus 로고    scopus 로고
    • Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: Pathways involving a novel catechol metabolite
    • Hu Y and Kupfer D (2002) Metabolism of the endocrine disruptor pesticide-methoxychlor by human P450s: Pathways involving a novel catechol metabolite. Drug Memb Dispos 30:1035-1042.
    • (2002) Drug Memb Dispos , vol.30 , pp. 1035-1042
    • Hu, Y.1    Kupfer, D.2
  • 16
    • 0030235940 scopus 로고    scopus 로고
    • Effects of cytochrome P450 antibodies on the oxidative demethylation of methoxychlor catalyzed by rat liver cytochrome P450 isozymes: Isozyme specificity and alteration of enantiotopic selectivity
    • Kishimoto D and Kurihara N (1996) Effects of cytochrome P450 antibodies on the oxidative demethylation of methoxychlor catalyzed by rat liver cytochrome P450 isozymes: Isozyme specificity and alteration of enantiotopic selectivity. Pestic Biochem Physiol 56:44-52.
    • (1996) Pestic Biochem Physiol , vol.56 , pp. 44-52
    • Kishimoto, D.1    Kurihara, N.2
  • 17
    • 0002761456 scopus 로고
    • Enantioselectivity of cytochrome P450-catalyzed oxidative demethylation of methoxychlor-alteration of selectivity depending on isozymes and substrate concentration
    • Kishimoto D, Oku A, and Kurihara N (1995) Enantioselectivity of cytochrome P450-catalyzed oxidative demethylation of methoxychlor-alteration of selectivity depending on isozymes and substrate concentration. Pestic Biochem Physiol 51:12-19.
    • (1995) Pestic Biochem Physiol , vol.51 , pp. 12-19
    • Kishimoto, D.1    Oku, A.2    Kurihara, N.3
  • 18
    • 0030811096 scopus 로고    scopus 로고
    • Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms
    • Ko J-W, Sukhova N, Thacker D, Chen P, and Flockhart DA (1997) Evaluation of omeprazole and lansoprazole as inhibitors of cytochrome P450 isoforms. Drug Metab Dispos 25:853-862.
    • (1997) Drug Metab Dispos , vol.25 , pp. 853-862
    • Ko, J.-W.1    Sukhova, N.2    Thacker, D.3    Chen, P.4    Flockhart, D.A.5
  • 19
    • 0031039888 scopus 로고    scopus 로고
    • Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta
    • Kuipper GG, Carlsson B, Grandien K, Enmark E, Haggblad J, Nilsson S, and Gustafsson JA (1997) Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138:863-870.
    • (1997) Endocrinology , vol.138 , pp. 863-870
    • Kuipper, G.G.1    Carlsson, B.2    Grandien, K.3    Enmark, E.4    Haggblad, J.5    Nilsson, S.6    Gustafsson, J.A.7
  • 20
    • 0018667377 scopus 로고
    • A novel in vitro method for demonstrating proestrogens. Metabolism of methoxychlor and o,p′-DDT by liver microsomes in the presence of uteri and effects of intracellular distribution of estrogen receptors
    • Kupfer D and Bulger WH (1979) A novel in vitro method for demonstrating proestrogens. Metabolism of methoxychlor and o,p′-DDT by liver microsomes in the presence of uteri and effects of intracellular distribution of estrogen receptors. Life Sci 25:975-984.
    • (1979) Life Sci , vol.25 , pp. 975-984
    • Kupfer, D.1    Bulger, W.H.2
  • 21
    • 0025248895 scopus 로고
    • Metabolism of methoxychlor by hepatic P-450 monooxygenases in rat and human. Characterization of a novel catechol metabolite
    • Kupfer D, Bulger WH, and Theoharides AD (1990) Metabolism of methoxychlor by hepatic P-450 monooxygenases in rat and human. Characterization of a novel catechol metabolite. Chem Res Toxicol 3:8-16.
    • (1990) Chem Res Toxicol , vol.3 , pp. 8-16
    • Kupfer, D.1    Bulger, W.H.2    Theoharides, A.D.3
  • 22
    • 0000586168 scopus 로고
    • Effects of added protein on the rate and enantiotopic selectivity of oxidative O-demethylation of methoxychlor in rat liver microsomes
    • Kurihara N and Oku A (1991) Effects of added protein on the rate and enantiotopic selectivity of oxidative O-demethylation of methoxychlor in rat liver microsomes. Pestic Biochem Physiol 40:227-235.
    • (1991) Pestic Biochem Physiol , vol.40 , pp. 227-235
    • Kurihara, N.1    Oku, A.2
  • 23
    • 0001880140 scopus 로고
    • Metcalf RL and McKelevey JJ eds, John Wiley and Sons, New York
    • Metcalf RL (1976) The Future of Insecticides (Metcalf RL and McKelevey JJ eds) pp 223-285, John Wiley and Sons, New York.
    • (1976) The Future of Insecticides , pp. 223-285
    • Metcalf, R.L.1
  • 26
    • 0034990627 scopus 로고    scopus 로고
    • Quantitative analysis of estrogen receptor proteins in rat mammary gland
    • Saji S, Sakaguchi H, Andersson S, Warner M, and Gustafsson J (2001) Quantitative analysis of estrogen receptor proteins in rat mammary gland. Endocrinology 142:3177-3186.
    • (2001) Endocrinology , vol.142 , pp. 3177-3186
    • Saji, S.1    Sakaguchi, H.2    Andersson, S.3    Warner, M.4    Gustafsson, J.5
  • 27
    • 0035155252 scopus 로고    scopus 로고
    • Interactions of delavirdine with human liver microsomal cytochrome P450: Inhibition of CYP2C9,i Cyp2C19 and CYP2D6
    • Voorman RL, Payne NA, Wienkers LC, Hauer MJ, and Sanders PE (2001) Interactions of delavirdine with human liver microsomal cytochrome P450: Inhibition of CYP2C9, Cyp2C19 and CYP2D6. Drug Metab Dispos 29:41-47.
    • (2001) Drug Metab Dispos , vol.29 , pp. 41-47
    • Voorman, R.L.1    Payne, N.A.2    Wienkers, L.C.3    Hauer, M.J.4    Sanders, P.E.5
  • 28
    • 0034871380 scopus 로고    scopus 로고
    • Differential gene expression in response to methoxychlor and estradiol through ERalpha. ERbeta and AR in reproductive tissues of female mice
    • Waters KM, Safe S, and Gaido KW (2001) Differential gene expression in response to methoxychlor and estradiol through ERalpha. ERbeta and AR in reproductive tissues of female mice. Toxicol Sci 63:47-56.
    • (2001) Toxicol Sci , vol.63 , pp. 47-56
    • Waters, K.M.1    Safe, S.2    Gaido, K.W.3
  • 29
    • 0036194969 scopus 로고    scopus 로고
    • Combined effects of dietary phytoestrogen and synthetic endocrine-active compound on reproductive development in Sprague-Dawley rats: Genistein and methoxychlor
    • You L, Casanova M, Bartolucci EJ, Fryczynski MW, Dorman DC, Everitt JI, Gaido KW, Ross SM, and Heck Hd H (2002) Combined effects of dietary phytoestrogen and synthetic endocrine-active compound on reproductive development in Sprague-Dawley rats: Genistein and methoxychlor. Toxicol Sci 66:91-104.
    • (2002) Toxicol Sci , vol.66 , pp. 91-104
    • You, L.1    Casanova, M.2    Bartolucci, E.J.3    Fryczynski, M.W.4    Dorman, D.C.5    Everitt, J.I.6    Gaido, K.W.7    Ross, S.M.8    Heck, Hd.H.9


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