Metabolism of the aryl hydrocarbon receptor agonist 3,3',4,4'- tetrachlorobiphenyl by the marine fish scup (Stenotomus chrysops) in vivo and in vitro

Drug Metabolism and Disposition

Volumn 25, Issue 5, 1997, Pages 564-572

  White, Renee D ^b   Shea, Damian ^b   Stegeman, John J ^a  

^a WOODS HOLE OCEANOGRAPHIC INSTITUTION   (United States)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

3,3',4,4' TETRACHLOROBIPHENYL; HYDROCARBON;

AEROBIC METABOLISM; ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; CATALYSIS; DATA ANALYSIS; DRUG DISPOSITION; DRUG DISTRIBUTION; DRUG LIVER LEVEL; DRUG METABOLISM; FISH; NONHUMAN; PRIORITY JOURNAL;

ANIMALS; BILE; CYTOCHROME P-450 CYP1A1; DOSE-RESPONSE RELATIONSHIP, DRUG; FISHES; MICROSOMES, LIVER; MUSCLES; NITROSAMINES; POLYCHLORINATED BIPHENYLS; RECEPTORS, ARYL HYDROCARBON; TISSUE DISTRIBUTION;

ANIMALIA; CHRYSOPS; STENOTOMUS CHRYSOPS;

EID: 0030996090     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (53)

1. S. Tanabe: PCB problems in the future: foresight from current knowledge. Environ. Poll. 50, 5-28 (1988).
2. R. W. Risebrough, P. Rieche, D. B. Peakall, S. G. Herman, and M. N. Kirven: Polychlorinated biphenyls in the global ecosystem. Nature 220, 1098-1102 (1968).
3. S. Safe: Toxicology, structure-function relationship, and human and environmental health impacts of polychlorinated biphenyls: progress and problems. Environ. Health Perspect. 100, 259-268 (1992).
4. V. A. McFarland and J. U. Clark: Environmental occurrence, abundance, and potential toxicity of polychlorinated biphenyl congeners: considerations for a congener-specific analysis. Environ. Health Perspect. 81, 225-239 (1989).
5. J. A. Goldstein and S. Safe: Mechanism of action and structure-activity relationships for the chlorinated dibenzo-p-dioxins and related compounds. In "Halogenated Biphenyls, Terphenyls, Naphthalenes, Dibenzodioxins and Related Products" (R. D. Kimbrough and A. A. Jensen, eds.) pp. 239-293. Elsevier Science Publishers, Biomedical Division, Amsterdam, 1989.
6. S. W. Fowler: Critical review of selected heavy metal and chlorinated hydrocarbon concentrations in the marine environment. Marine Environ. Res. 29, 1-64 (1990).
7. J. de Boer, C. J. N. Stronck, W. A. Traag, and J. van der Meer: Non-ortho and mono-ortho substituted chlorobiphenyls and chlorinated dibenzo-p-dioxins and dibenzofurans in marine and freshwater fish and shellfish from the Netherlands. Chemosphere 26, 1823-1842 (1993).
8. E. Monosson and J. J. Stegeman: Cytochrome P450E (P450IA) induction and inhibition in winter flounder by 3,3′,4,4′-tetrachlorobiphenyl: comparison of response in fish from Georges Bank and Narragansett Bay. Environ. Toxicol. Chem. 10, 765-774 (1991).
9. F. Cordle, R. Locke, and J. Springer: Risk assessment in a federal regulatory agency: an assessment of risk associated with the human consumption of some species of fish contaminated with PCBs. Environ. Health Perspect. 45, 177-182 (1982).
10. P. D. Guiney, R. E. Peterson, M. J. Melancon, and J. J. Lech: The distribution and elimination of 2,5,2′,5′-[14C]tetrachlorobiphenyl in rainbow trout (Salmo gairdneri). Toxicol. Appl. Pharmacol. 39, 329-338 (1977).
11. M. J. Vodicnik and R. E. Peterson: The enhancing effect of spawning on elimination of a persistent polychlorinated biphenyl from female yellow perch. Fundam. Appl. Toxicol. 5, 770-776 (1985).
12. J. M. O'Connor and J. C. Pizza: Dynamics of polychlorinated biphenyls in striped bass from the Hudson River. III. Tissue disposition and routes for elimination. Estuaries 10, 68-77 (1987).
13. O. Hutzinger, D. M. Nash, S. Safe, A. S. W. DeFreitas, R. J. Norstrom, D. J. Wildish, and V. Zitko: Polychlorinated biphenyls: metabolic behavior of pure isomers in pigeons, rats, and brook trout. Science 178, 312-313 (1972).
14. R. L. Metcalf, J. R. Sanborn, P.-Y. Lu, and D. Nye: Laboratory model ecosystem studies of the degradation and fate of radiolabeled tri-, tetra-, and pentachlorobiphenyl compared with DDE. Arch. Environ. Contam. Toxicol. 3, 151-165 (1975).
15. J. R. Sanborn, W. F. Childers, and R. L. Metcalf: Uptake of three polychlorinated biphenyls, DDT, and DDE by the green sunfish, Lepomis cyanellus Raf. Bull. Environ. Contam. Toxicol. 13, 209-217 (1975).
16. 14C-tetrachlorobiphenyl. Bull. Environ. Contam. Toxicol. 15, 181-188 (1976).
17. R. Hinz and F. Matsumura: Comparative metabolism of PCB isomers by three species of fish and the rat. Bull. Environ. Contam. Toxicol. 18, 631-639 (1977).
18. 14C by goldfish after a single water treatment. Chemosphere 3, 221-230 (1978).
19. A. J. Niimi and B. G. Oliver: Biological half-lives of polychlorinated biphenyl (PCB) congeners in whole fish and muscle of rainbow trout (Salmo gairdneri). Can. J. Fish. Aquat. Sci. 40, 1388-1394 (1983).
20. J. P. Boon, F. Eijgenraam, J. M. Everaarts, and J. C. Duinker: A structure-activity relationship (SAR) approach towards metabolism of PCBs in marine animals from different trophic levels. Marine Environ. Res. 27, 159-176 (1989).
21. A. A. Elskus, J. J. Stegeman, J. W. Gooch, D. E. Black, and R. J. Pruell: Polychlorinated biphenyl congener distributions in winter flounder as related to gender, spawning site, and congener metabolism. Environ. Sci. Technol. 28, 401-407 (1994).
22. A. Murk, D. Morse, J. Boon, and A. Brouwer: In vitro metabolism of 3,3′,4,4′-tetrachlorobiphenyl in relation to ethoxyresorufin-O-deethylase activity in liver microsomes of some wildlife species and rat. Eur. J. Pharmacol. 270, 253-261 (1994).
23. C. Ishida, N. Koga, N. Hanioka, H. K. Saeki, and H. Yoshimura: Metabolism in vitro of 3,4,3′,4′-and 2,5,2′,5′-tetrachlorobiphenyl by rat liver microsomes and highly purified cytochrome P450. J. Pharmacobiodyn. 14, 276-284 (1991).
24. L. S. Kaminsky, M. W. Kennedy, S. M. Adams, and F. P. Guengerich: Metabolism of dichlorobiphenyls by highly purified isozymes of rat liver cytochrome P-450. Biochemistry 20, 7379-7384 (1981).
25. R. A. Mills, C. D. Millis, G. A. Dannan, F. P. Guengerich, and S. D. Aust: Studies on the structure-activity relationships for the metabolism of polybrominated biphenyls by rat liver microsomes. Toxicol. Appl. Pharmacol. 78, 96-104 (1985).
26. J. F. Brown: Metabolic alterations of PCB residues in aquatic fauna: distributions of cytochrome P4501A-and P4502B-like activities. Marine Environ. Res. 34, 261-266 (1992).
27. 14C]biphenyl in pregnant mice: enrichment of phenol and methyl sulphone metabolites in late gestational fetuses. Xenobiotica 16, 295-306 (1986).
28. N. Koga, M. Beppu, C. Ishida, and H. Yoshimura: Further studies on metabolism in vivo of 3,3′,4,4′-tetrachlorobiphenyl in rats: identification of minor metabolites in rat faeces. Xenobiotica 19, 1307-1318 (1989).
29. E. Klasson Wehler, A. Bergman, I. Brandt, P. O. Darnerud, and C. A. Wachtmeister: 3,3′,4,4′-Tetrachlorobiphenyl excretion and tissue retention of hydroxylated metabolites in the mouse. Drug Metab. Dispos. 17, 441-448 (1989).
30. M. E. Hahn and J. J. Stegeman: Regulation of cytochrome P450IAI in teleosts: sustained induction of CYP1A1 mRNA, protein, and catalytic activity by 2,3,7,8-tetrachlorodibenzofuran in the marine fish Stenotomus chrysops. Toxicol. Appl. Pharmacol. 127, 187-198 (1994).
31. P. K. Smith, R. I. Krohn, G. T. Hermanson, A. K. Mallia, F. H. Gartner, M. D. Provenzano, E. K. Fujimoto, N. M. Goeke, B. J. Olson, and D. C. Klenk: Measurement of protein using bicinchoninic acid. Anal. Biochem. 150, 76-85 (1985).
32. K. Helrich: "Official Methods of Analysis of the Association of Official Analytical Chemists," (K. Helrich, ed.), 15th ed., pp. 283-284. Association of Official Analytical Chemists, Arlington, VA, p. 1990.
33. T. Omura and R. Sato: The carbon monoxide-binding pigment of liver microsomes. J. Biol. Chem. 239, 2370-2378 (1964).
34. J. J. Stegeman and R. L. Binder: High benzo[a]pyrene hydroxylase activity in the marine fish Sienotomus versicolor. Biochem. Pharmacol. 28, 1686-1688 (1979).
35. M. E. Hahn, T. M. Lamb, M. E. Schultz, R. M. Smolowitz, and J. J. Stegeman: Cytochrome P4501A induction and inhibition by 3,3′,4,4′-tetrachlorobiphenyl in an Ah receptor-containing fish hepatoma cell line (PLHC-1). Aquat. Toxicol. 26, 185-208 (1993).
36. P. J. Kloepper-Sams, S. S. Park, H. V. Gelboin, and J. J. Stegeman: Specificity and cross-reactivity of monoclonal and polyclonal antibodies against cytochrome P450E of the marine fish scup. Arch. Biochem. Biophys. 253, 268-278 (1987).
37. S. S. Park, H. Miller, A. V. Klotz, P. J. Kloepper-Sams, J. J. Stegeman, and H. V. Gelboin: Monoclonal antibodies to liver microsomal cytochrome P-450E of the marine fish Stenotomus chrysops (scup): cross-reactivity with 3-methylcholanthrene induced rat cytochrome P-450. Arch. Biochem. Biophys. 249, 339-350 (1986).
38. R. G. Schnellman, C. W. Putnam, and I. G. Sipes: Metabolism of 2,2′,3,3′,6,6′-hexachlorobiphenyl and 2,2′4,4′,5,5′-hexachlorobiphenyl by human hepatic microsomes. Biochem. Pharmacol. 32, 3233-3239 (1983).
39. J. J. Stegeman, R. L. Binder, and A. Orren: Hepatic and extrahepatic microsomal electron transport components and mixed-function oxygenases in the marine fish Stenotomus versicolor. Biochem. Pharmacol. 28, 3431-3439 (1979).
40. R. L. Binder: Xenobiotic Monooxygenase Activity and the Response to Inducers of Cytochrome P-450 during Embryonic and Larval Development in Fish. Ph.D. Dissertation, MIT/WHOI Joint Program, Woods Hole, MA, 1982.
41. A. V. Klotz, J. J. Stegeman, and C. Walsh: An alternative 7-ethoxyresorufin O-deethylase activity assay: a continuous visible spectrophotometric method for measurement of cytochrome P-450 monooxygenase activity. Anal. Biochem. 140, 138-145 (1984).
42. N. R. Orme-Johnson, D. R. Light, R. W. White-Stevens, and W. H. Orme-Johnson: Steroid binding properties of beef adrenal cortical cytochrome P450 which catalyzes the conversion of cholesterol into pregnenolone. J. Biol. Chem. 254, 2103-2111 (1979).
43. C. T. Chiou: Partition coefficients of organic compounds in lipid-water systems and correlations with fish bioconcentration factors. Environ. Sci. Technol. 19, 57-62 (1985).
44. B. Clark and D. A. Smith: An Introduction to Pharmacokinetics. Blackwell Scientific Publications, Oxford, 1981.
45. R. D. White, D. Shea, A. R. Solow, and J. J. Stegeman: Induction and post-transcriptional suppression of hepatic cytochrome P450 1A1 by 3,3′,4,4′,-tetrachlorobiphenyl. Biochem. Pharmacol. in press, 1997.
46. E. Klasson Wehler, B. Brunstrom, U. Rannug, and A. Bergman: 3,3′,4,4′-Tetrachlorobiphenyl: metabolism by the chick embryo in ovo and toxicity of hydroxylated metabolites. Chem.-Biol. Interact. 73, 121-132 (1990).
47. H. Yoshimura, Y. Yonemoto, H. Yamada, N. Koga, K. Oguri, and S. Saeki: Metabolism in vivo of 3,4,3′,4′-tetrachlorobiphenyl and toxicological assessment of the metabolites in rats. Xenobiotica 17, 897-910 (1987).
48. J. J. Stegeman, A. V. Klotz, B. R. Woodin, and A. M. Pajor: Induction of hepatic cytochrome P-450 in fish and the indication of environmental induction in scup. Aquat. Toxicol. 1, 197-212 (1981).
49. T. K. H. Chang, F. J. Gonzalez, and D. J. Waxman: Evaluation of triacetyloleandomycin, alpha-naphthoflavone and diethyldithiocarbamate as selective chemical probes for inhibition of human cytochromes P450. Arch. Biochem. Biophys. 311, 437-442 (1994).
50. N. Takahashi, C. L. Miranda, M. C. Henderson, D. R. Buhler, D. E. Williams, and G. S. Bailey: Inhibition of in vitro aflatoxin B1-DNA binding in rainbow trout by CYP1A inhibitors: α-naphthoflavone, β-naphthoflavone and trout CYP1A1 peptide antibody. Comp. Biochem. Physiol. 110C, 273-280 (1995).
51. J. R. Halpert, F. P. Guengerich, J. R. Bend, and M. A. Correia: Selective inhibitors of cytochromes P450. Toxicol. Appl. Pharmacol. 125, 163-175 (1994).
52. J. W. Gooch, A. A. Elskus, P. J. Kloepper-Sams, M. E. Hahn, and J. J. Stegeman: Effects of ortho and non-ortho substituted polychlorinated biphenyl congeners on the hepatic monooxygenase system in scup (Stenotomus chrysops). Toxicol. Appl. Pharmacol. 98, 422-433 (1989).
53. P. M. Warren and G. D. Bellward: Induction of aryl hydrocarbon hydroxylase by 3-methylcholanthrene in liver, lung and kidney of gonadectomized and sham-operated wistar rats. Biochem. Pharmacol 27, 2537-2541 (1978).