2,3,7,8-Tetrafluorodibenzo-p-dioxin: A potent agonist of the murine dioxin receptor

Environmental Toxicology and Pharmacology

Volumn 3, Issue 2, 1997, Pages 105-113

  Schmitz, Hans Joachim ^a   Weber, Roland ^a   Hagenmaier, Andrea ^a   Hagenmaier, Hanspaul ^a   Poellinger, Lorenz ^b   Schrenk, Dieter ^a  

^a UNIVERSITY OF TÜBINGEN   (Germany)

^b KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

Author keywords

2,3,7,8 Tetrachlorodibenzo p dioxin; 2,3,7,8 Tetrafluorodibenzo p dioxin; Aryl hydrocarbon receptor; Cytochrome P4501A1 promoter; Mouse hepatocytes

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; AROMATIC HYDROCARBON RECEPTOR; CYTOCHROME P450 ISOENZYME; ORGANOHALOGEN DERIVATIVE;

AGONIST; ANIMAL CELL; ANIMAL EXPERIMENT; ARTICLE; CONTROLLED STUDY; ENZYME INDUCTION; HEPATOMA CELL; LIVER HOMOGENATE; MALE; MOUSE; NONHUMAN; PRIORITY JOURNAL; RECEPTOR BINDING; XENOBIOTIC METABOLISM;

EID: 0030961850     PISSN: 13826689     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1382-6689(96)00146-9     Document Type: Article

References (43)

1. Ahlborg, U.G., G.C. Becking, L.S. Birnbaum, A. Brouwer, H.J.G.M. Derks, M. Feeley, G. Golor, A. Hanberg, J.C. Larsen, A.K.D. Liem, S.H. Safe, C. Schlatter, F. Waern, M. Younes and E. Yrjängheikki, 1994, Toxic equivalency factors for dioxin-like PCBs, Chemosphere 28, 1049.
2. Birnbaum, L.S., 1991, Distribution and excretion of 2,3,7,8-tetrachlorodibenzo-p -dioxin in congenic strains of mice which differ at the Ah locus, Drug Metab. Dispos. 14, 34.
3. Birnbaum, L.S., R.E. Morrissey and H.W. Harris., 1991, Teratogenic effects of 2,3,7,8-tetra-bromodibenzo-p-dioxin and three polybrominated dibenzofurans in C57BL/6N mice, Toxicol. Appl. Pharmacol. 107, 141.
4. Burbach, K.M., A. Poland and C.A. Bradfield., 1992, Cloning of the Ah receptor cDNA reveals a distinctive ligand-activated transcription factor, Proc. Natl. Acad. Sci. USA 89, 8185.
5. Burke, M.D., S. Thompson, R.J. Weaver, C.R. Wolf and R.T. Mayer, 1994, Cytochrome P-450 specificities of alkoxyresorufin O-dealkylation in human and rat liver, Biochem. Pharmacol. 48, 923.
6. Cuthill, S., A. Wilhelmsson and L. Poellinger, 1991, Role of the ligand in intracellular receptor function: receptor affinity determines activation in vitro of the latent dioxin receptor to a DNA-binding form, Mol. Cell. Biol. 11, 401.
7. De Jongh, J., H.R. Buser and H. Poiger, 1993, The metabolism of 2,3,7,8-tetrabromodibenzo-dioxin in the rat, Xenobiotica 23, 19.
8. De Vito, M.J., W.E. Maier, J.J. Diliberto and L.S. Birnbaum, 1993, Comparative ability of various PCBs, PCDFs, and TCDD to induce cytochrome P450 1A1 and 1A2 activity following 4 weeks of treatment, Fund. Appl. Toxicol. 20, 125.
9. Ema, M., K. Sogawa, Y. Watanabe, Y. Chujoh, N. Matsushita, O. Gotoh, Y. Funae and Y. Fujii-Kuriyama, 1992, cDNA cloning and structure of mouse putative Ah receptor, Biochem. Biophys. Res. Commun. 184, 246.
10. Favreau, L.V. and C.B. Pickett, 1991, Transcriptional regulation of the rat NAD(P)H:quinone reductase gene: identification of regulatory elements controlling basal level expression and inducible expression by planar aromatic compounds and phenolic antioxidants, J. Biol. Chem. 266, 4556.
11. Fujisawa-Sehara, A., K. Sogawa, C. Nishi and Y. Fujii-Kuriyama, 1986, Regulatory DNA elements localized remotely upstream from the drug-metabolizing cytochrome P450c gene, Nucleic Acids Res. 14, 1465.
12. Fort, P., L. Marty, M. Piechaezyl, S.E. Sabrouty, C. Dani, P. Jeanteur and J.M. Blanchard, 1985, Various rat tissues express only one major mRNA species from the glyceraldehyde-3-phosphate-dehydrogenase multigenic family, Nucleic Acids Res. 13, 1431.
13. 1 mice, Drug Metab. Dispos. 11, 397.
14. 3-450, Gene 29, 281.
15. Ivens, I.A., E. Löser, M. Rinke, U. Schmidt and U. Mohr, 1993, Subchronic toxicity of 2,3,7,8-tetrabromodibenzo-p-dioxin in rats, Toxicology 83, 181-201.
16. Kedderis, L.B., J.J. Dilibert, P. Linko, J.A. Goldstein and L.S. Birnbaum, 1991, Disposition of 2,3,7,8-tetrabromodibenzo-p-dioxin and 2,3,7,8-tetrachlorodibenzo-p-dioxin in the rat: Biliary excretion and induction of cytochromes CYP1A1 and CYP1A2, Toxicol. Appl. Pharmacol. 111, 163.
17. Kende, A.S., J.J. Wade and A. Poland, 1974, Synthesis and Fourier transform carbon-13 nuclear magnetic resonance spectroscopy of new toxic polyhalodibenzo-p-dioxins, J. Org. Chem. 39, 931.
18. 14C]2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the mouse, Toxicol. Appl. Pharmacol. 73, 69.
19. Nagao, T., G. Golor, R. Krowke and D. Neubert, 1990, Comparison of cleft palate frequency induced by 2,3,7,8-tetrabromodibenzo-p-dioxin and 2,3,7,8-tetrachlorodibenzo-p-dioxin in mice, in: Organonohalogen Compounds, Vol. 1, eds. O. Hutzinger and H. Fiedler (Ecoinforma Press, Bayreuth) p. 317.
20. NATO/CCMS, 1988, Scientific Basis for the International Toxicity Equivalency Factors (I-TEF) Method for Risk Assessment of Complex Mixtures. Report no. 178, North Atlantic Treaty Organization, CCMS, New York.
21. Park, B.K. and N.R. Kitteringham, 1994, Effects of fluorine substitution on drug metabolism: pharmacological and toxicological implications, Drug Metab. Rev. 26, 605.
22. Paulson, K.E., J.E. Darnell Jr., T. Rushmore and C.B. Pickett, 1990, Analysis of the upstream elements of the xenobiotic compound-inducible and positionally regulated glutathione S-transferase Ya gene, Mol. Cell Biol. 10, 1841.
23. Perdew, G.H, 1988, Association of the Ah receptor with the 90 kDa heat shock protein, J. Biol. Chem. 263, 13 802.
24. Poellinger, L., M. Göttlicher and J.-Å. Gustafsson, 1992, The dioxin and peroxisome proliferator-activated receptors: nuclear receptors in search of endogenous ligands, Trends Pharm. Sci. 13, 241.
25. Poiger, H. and H.R. Buser, 1984, The metabolism of TCDD in the dog and rat, in: Biological Mechanisms of Dioxin Action, eds. A. Poland and R.D. Kimbrough, Banbury report no. 18, Cold Spring Harbor Laboratory, p. 39.
26. Poland A. and E. Glover, 1977, Chlorinated biphenyl induction of arylhydrocarbon hydroxylase activity: a study of the structure-activity relationship, Mol. Pharmacol. 13, 924.
27. Poland, A. and J.C. Knutson, 1982, 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: examination of the mechanism of toxicity, Annu. Rev. Pharmacol. Toxicol. 22, 517.
28. 125I]2-Iodo-3,7,8-trichlorodibenzo-p-dioxin-binding species in mouse liver induced by agonists for the Ah receptor: characterization and identification, Mol. Pharmacol. 36, 113.
29. Safe, S.H., 1986, Comparative toxicology and mechanism of action of polychlorinated dibenzo-p-dioxins and dibenzofurans, Annu. Rev. Pharmacol. Toxicol. 26, 371.
30. Safe, S., 1990, Polychlorinated biphenyls (PCBs), dibenzo-p-dioxins (PCDDs), dibenzofurans (PCDFs), and related compounds: environmental and mechanistic considerations which support the development of toxic equivalency factors, CRC Crit. Rev. Toxicol. 21, 51.
31. Sawahata, T., J.R. Olson and R.A. Neal, 1982, Identification of metabolites of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) formed on incubation with isolated rat hepatocytes, Biochem. Biophys. Res. Commun. 105, 341.
32. Sawyer, T.W. and S. Safe, 1982. PCB isomers and congeners: induction of aryl hydrocarbon hydroxylase and ethoxyresorufin O-deetylase enzyme activities in rat hepatoma cells, Toxicol. Lett. 13, 87.
33. Schmitz, H.-J., A. Hagenmaier, H. Hagenmaier, K.W. Bock and D. Schrenk, 1995, Potency of mixtures of polychlorinated biphenyls as inducers of dioxin receptor-regulated CYP1A activity in rat hepatocytes and H4IIE cells, Toxicology 99, 47.
34. Schrenk, D., H.-P. Lipp, T. Wiesmüller, H. Hagenmaier and K.W. Bock, 1991, Assessment of biological activities of mixtures of polychlorinated dibenzo-p-dioxins: comparison between defined mixtures and their constituents, Arch. Toxicol. 65, 114.
35. Schrenk, D., S. Schäfer and Bock, K.W, 1994a, 2,3,7,8-Tetrachlorodibenzo-p-dioxin as growth modulator in mouse hepatocytes with high and low affinity Ah receptor, Carcinogenesis 15, 27.
36. Schrenk, D., T.W. Gant, A. Michalke, A. Orzechowski, J.A. Silverman, N. Battula and S.S. Thorgeirsson, 1994b, Metabolic activation of 2-acetylaminofluorene is required for induction of multidrug resistance gene expression in rat liver cells, Carcinogenesis 15, 2541.
37. Waziers, I., H. de Cugnenc, C.S. Yang, J.-P. Leroux and P.H. Beaune, 1990, Cytochrome P-450 isoenzymes, epoxide hydrolase and glutathione transferases in rat and human hepatic and extrahepatic tissues, J. Pharmacol. Exp. Ther. 253, 387.
38. Weber, R., D. Schrenk, H.-J. Schmitz, A. Hagenmaier and H. Hagenmaier, 1995, Polyfluorinated dibenzodioxins and dibenzofurans - synthesis, analysis, formation and toxicology, Chemosphere 30, 629.
39. Whitelaw, M.L., I. Pongratz, A. Wilhelmsson, J.Å. Gustafsson and L. Poellinger, 1993a, Ligand-dependent recruitment of the Arnt coregulator determines DNA recognition by the dioxin receptor, Mol. Cell. Biol. 13, 2504.
40. Whitelaw, M.L., M. Göttlicher, J.Å. Gustafsson and L. Poellinger, 1993b, Definition of a novel ligand binding domain of a nuclear bHLH receptor: colocalization of ligand and hsp90 binding activities within rhe regulable inactivation domain of the dioxin receptor, EMBO J. 12, 4169.
41. Whitlock, J.P. Jr., 1993, Mechanistic aspects of dioxin action, Chem. Res. Toxicol. 6, 754.
42. Wilhelmsson, A., S. Cuthill, M. Denis, A.C. Wikström, J.-Å. Gustafsson, J.-Å. Gustafsson and L. Poellinger, 1990, The specific DNA binding activity of the dioxin receptor is modulated by the 90 kDa heat shock protein, EMBO J. 9, 69.
43. Wroblewski, V.J., and J.R. Olson, 1988, Effect of monooxygenase inducers and inhibitors on the hepatic metabolism of 2,3,7,8-tetrachlorodibenzo-p-dioxin in the rat and hamster, Drug Metab. Dispos. 16, 43.