Comparative in vitro metabolism of methoxychlor in male and female rats: Metabolism of demethylated methoxychlor metabolites by precision-cut rat liver slices

References

• Ankley GT, Jensen KM, Kahl MD, Korte JJ, Makynen EA. 2001. Description and evaluation of a short-term reproduction test with the fathead minnow (Pimephales promelas). Environmental Toxicology and Chemistry 20:1276–1290.
   PubMed Web of Science ®Google Scholar
• Barr J, Weir AJ, Brendel K, Sipes IG. 1991. Liver slices in dynamic organ culture. II. An in vitro cellular technique for the study of integrated drug metabolism using human tissue. Xenobiotica 21:341–350.
   Google Scholar
• Bradford MM. 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 72:248–254.
   PubMed Web of Science ®Google Scholar
• Bulger WH, Muccitelli R1\4, Kupfer D. 1978a. Studies on the in vivo and in vitro estrogenic activities of methoxychlor and its metabolites. Role of hepatic mono-oxygenase in methoxychlor activation. Biochemical Pharmacology 27:2417–2423.
   Google Scholar
• Bulger WH, Muccitelli RM, Kupfer D. 1978b. Interactions of methoxychlor, methoxychlor base-soluble contaminant, and 2,2-bis(p-hydroxypheny1)-1,1,1-trichloroethane with rat uterine estrogen receptor. Journal of Toxicology and Environmental Health 4:881–893.
   PubMed Web of Science ®Google Scholar
• Chapin RE, Harris MW, Davis BJ, Ward SM, Wilson RE, Mauney MA, Lockhart AC, Smialowicz RJ, Moser VC, Burka LT, Collins BJ. 1997. The effects of perinatal/juvenile methoxychlor exposure on adult rat nervous, immune, and reproductive system function. Fundamentals of Applied Toxicology 40:138–157.
   PubMedGoogle Scholar
• Davison KL, Feil VJ, Lamoureux CH. 1982. Methoxychlor metabolism in goats. Journal of Agriculture and Food Chemistry 30:130–137.
   PubMed Web of Science ®Google Scholar
• Davison KL,, Lamoureux CH, Feil VJ. 1983. Methoxychlor metabolism in goats. 2. Metabolites in bile and movement through skin. Journal of Agriculture and Food Chemistry 31:164–166.
   PubMed Web of Science ®Google Scholar
• Dehal SS, 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 Metabolism and Disposition 22:937–946.
   PubMed Web of Science ®Google Scholar
• Dogterom P. 1993. Development of a simple incubation system for metabolism studies with precision-cut liver slices. Drug Metabolism and Disposition 21:699–704.
   PubMed Web of Science ®Google Scholar
• Dogterom P, Rothuizen J. 1993. A species comparison of tolbutamide metabolism in precision-cut liver slices from rats and dogs. Qualitative and quantitative sex differences. Drug Metabolism and Disposition 21:705–709.
   PubMed Web of Science ®Google Scholar
• Ekins S. 1996. Past, present, and future applications of precision-cut liver slices for in vitro xenobiotic metabolism. Drug Metabolism Reviews 28:591–623.
   PubMed Web of Science ®Google Scholar
• Elsby R, Maggs JL, Ashby J, Paton D, Sumpter JP, Park BK. 2001. Assessment of the effects of metabolism on the estrogenic activity of xenoestrogens: A two-stage approach coupling human liver microsomes and a yeast estrogenicity assay. Journal of Pharmacology and Experimental Therapeutics 296:329–337.
   PubMed Web of Science ®Google Scholar
• Gaido KW, Leonard LS, Lovell S, Gould JC, Baba D, Portier CJ, McDonnell DP. 1997. Evaluation of chemicals with endocrine modulating activity in a yeast-based steroid hormone receptor gene transcription assay. Toxicology and Applied Pharmacology 143:205–212.
   PubMed Web of Science ®Google Scholar
• Gaido KW, Maness SC, McDonnell DP, Dehal SS, Kupfer D, Safe S. 2000. Interaction of methoxychlor and related compounds with estrogen receptor a and 13, and androgen receptor: Structure-activity studies. Molecular Pharmacology 58:852–858.
   PubMed Web of Science ®Google Scholar
• Gray LE Jr, Ostby J, Ferrell J, Rehnberg G, Linder R, Cooper R, Goldman J, Slott V, Laskey J. 1989. A dose-response analysis of methoxychlor-induced alterations of reproductive development and function in the rat. Fundamentals and Applied Toxicology 12:92–108.
   PubMedGoogle Scholar
• Hashemi E, Dobrota M, Till C, Ioannides C. 1999. Structural and functional integrity of precision-cut liver slices in xenobiotic metabolism: A comparison of the dynamic organ and multiwell plate culture procedures. Xenobiotica 29:11–25.
   PubMed Web of Science ®Google Scholar
• Hemmer MJ, Hemmer BL, Bowman CJ, Kroll KJ, Folmar LC, Marcovich D, Hoglund MD, Denslow ND. 2001. Effects of p-nonylphenol, methoxychlor, and endosulfan on vitellogenin induction and expression in sheepshead minnow (Cyprinodon variegatus). Environmental Toxicology and Chemistry 20:336–343.
   PubMed Web of Science ®Google Scholar
• Hu Y, Krausz K, Gelboin HV, Kupfer D. 2004. CYP2C subfamily, primarily CYP2C9, catalyses the enantioselective demethylation of the endocrine disruptor pesticide methoxychlor in human liver microsomes: Use of inhibitory monoclonal antibodies in P450 identification. Xenobiotica 34:117–132.
   PubMed Web of Science ®Google Scholar
• Hu Y, Kupfer D. 2002a. Metabolism of the endocrine disruptor pesticide methoxychlor by human P450s: Pathways involving a novel catechol metabolite. Drug Metabolism and Disposition 30:1035–1042.
   PubMed Web of Science ®Google Scholar
• Hu Y, Kupfer D. 2002b. Enantioselective metabolism of the endocrine disruptor pesticide methoxychlor by human cytochromes P450 (P450s): Major differences in selective enantiomer formation by various P450 isoforms. Drug Metabolism and Disposition 30:1329–1336.
   PubMed Web of Science ®Google Scholar
• Ichinose R, Nakayama M, Kuramoto J, Kurihara N. 1986. Synthesis of chiral [monomethyl-d3]methoxychlor and related deuterium-labeled compounds. Agricultural and Biological Chemistry 50:1331–1332.
   Web of Science ®Google Scholar
• Kapoor IP, Metcalf RL, Nystrom RF, Sangha GK. 1970. Comparative metabolism of methoxychlor, methiochlor, and DDT in mouse, insects, and in a model ecosystem. Journal of Agriculture and Food Chemistry 18:1145–1152.
   PubMed Web of Science ®Google Scholar
• Kishimoto D, Oku A, Kurihara N. 1995. Enantiotopic selectivity of cytochrome P450-catalysed oxidative demethylation of methoxychlor: Alteration of selectivity depending on isozymes and substrate concentrations. Pesticide Biochemistry and Physiology 51:12–19.
   Google Scholar
• Kurihara N, Ichinose R, Takao S. 1989. Demethylation of deuteriated methoxychlor in isolated rat hepatocytes. Journal of Pesticide Science 14:85–87.
   Google Scholar
• Kurihara N, Oku A. 1991. Effects of added protein (bovine serum albumin) on the rate and enantiotopic selectivity of oxidative O-demethylation of methoxychlor in rat liver microsomes. Pesticide Biochemistry and Physiology 40:227–235.
   Google Scholar
• Miyashita M, Shimada T, Nakagami S, Kurihara N, Miyagawa H, Akamatsu M. 2004. Enantioselective recognition of mono-demethylated methoxychlor metabolites by the estrogen receptor. Chemosphere 54:1273–1276.
   PubMedGoogle Scholar
• Ohyama K, Maki S, Sato K, Kato Y. 2004. In vitro metabolism of [14C]methoxychlor in rat, mouse, Japanese quail and rainbow trout in precision-cut liver slices. Xenobiotica 34:741–754.
   PubMed Web of Science ®Google Scholar
• Ohyama K, Maki S, Sato K, Kato Y. 2005. Comparative in vitro metabolism of the suspected pro-oestrogenic compound, methoxychlor in precision-cut liver slices from male and female rats. Xenobiotica 35:331–342.
   Google Scholar
• Ousterhout J, Struck RF, Nelson JA. 1981. Estrogenic activities of methoxychlor metabolites. Biochemical Pharmacology 30:2869–2871.
   PubMed Web of Science ®Google Scholar
• Pritchett jj, Kuester RK, Sipes IG. 2002. Metabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans. Drug Metabolism and Disposition 30:1180–1185.
   PubMedGoogle Scholar
• Shelby MD, Newblod RR, Tully DB, Chae K, Davis VL. 1996. Assessing environmental chemicals for estrogenicity using a combination of in vitro and in vivo assays. Environmental Health Perspectives 104:1296–1300.
   Google Scholar
• Steensma A, Beamand JA, Walters DG, Price RJ, Lake BG. 1994. Metabolism of coumarin and 7-ethoxycoumarin by rat, mouse, guinea pig, Cynomolgus monkey and human precision-cut liver slices. Xenobiotica 24:893–907.
   PubMed Web of Science ®Google Scholar
• Stresser DM, Kupfer D. 1998a. Prosubstrates of CYP3A4, the major human hepatic cytochrome P450. Transformation into substrates by other P450 isoforms. Biochemical Pharmacology 55:1861–1871.
   PubMed Web of Science ®Google Scholar
• Stresser DM, Kupfer D. 1998b. Human cytochrome P450-catalysed conversion of the proestrogenic pesticide methoxychlor into an estrogen. Role of CYP2C19 and CYP1A2 in O-demethylation. Drug Metabolism and Disposition 26:868–874.
   PubMed Web of Science ®Google Scholar
• Vickers AEM, Fischer V, Connors S, Fischer RL,, Baldeck JP, Maurer G, Brendel K. 1992. Cyclosporin a metabolism in human liver, kidney, and intestine slices. Comparison to rat and dog slices and human cell lines. Drug Metabolism and Disposition 20:802–809.
   Google Scholar
• Walsh JS, Patanella JE, Halm KA, Facchine KL. 1995. An improved HPLC assay for the assessment of liver slice metabolic viability using 7-ethoxycoumarin. Drug Metabolism and Disposition 23:869–874.
   PubMed Web of Science ®Google Scholar