Binding of polycyclic aromatic hydrocarbons (PAHs) to teleost aryl hydrocarbon receptors (AHRs)

Comparative Biochemistry and Physiology - B Biochemistry and Molecular Biology

Volumn 133, Issue 1, 2002, Pages 55-68

  Billiard, Sonya M ^a,e   Hahn, Mark E ^b   Franks, Diana G ^b   Peterson, Richard E ^c   Bols, Niels C ^d   Hodson, Peter V ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b WOODS HOLE OCEANOGRAPHIC INSTITUTION   (United States)

^c UNIVERSITY OF WISCONSIN MADISON   (United States)

^d UNIVERSITY OF WATERLOO   (Canada)

^e DUKE UNIVERSITY   (United States)

Author keywords

AHR; Binding affinity; CYP1A induction; PAH; TCDD

Indexed keywords

2,3,7,8 TETRACHLORODIBENZO PARA DIOXIN; CYTOCHROME P450 1A; POLYCYCLIC AROMATIC HYDROCARBON; RECEPTOR; AROMATIC HYDROCARBON RECEPTOR; COMPLEMENTARY DNA; CYTOCHROME P450 1A1; PHENANTHRENE DERIVATIVE; RETENE;

ANIMAL CELL; ARTICLE; BINDING AFFINITY; CELL LINE; HEPATOMA CELL; IN VITRO STUDY; JUVENILE; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAINBOW TROUT; RECEPTOR BINDING; STIMULUS RESPONSE; TELEOST; ANIMAL; BIOSYNTHESIS; CELL CULTURE; DANGEROUS GOODS; DRUG EFFECT; FISH; GENE EXPRESSION REGULATION; GENETICS; METABOLISM; RADIOASSAY;

ONCORHYNCHUS MYKISS; SALMONIDAE; TELEOSTEI;

ANIMALS; CYTOCHROME P-450 CYP1A1; DNA, COMPLEMENTARY; FISHES; GENE EXPRESSION REGULATION; HAZARDOUS SUBSTANCES; ONCORHYNCHUS MYKISS; PHENANTHRENES; POLYCYCLIC HYDROCARBONS, AROMATIC; RADIOLIGAND ASSAY; RECEPTORS, ARYL HYDROCARBON; TETRACHLORODIBENZODIOXIN; TUMOR CELLS, CULTURED;

EID: 0036752895     PISSN: 10964959     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1096-4959(02)00105-7     Document Type: Article

References (62)

1. Andreasen E.A., Tanguay R.L., Peterson R.E., Heideman W. Identification of a critical amino acid in the aryl hydrocarbon receptor. J. Biol. Chem. 277:2002;13210-13218.
2. Abnet C.C., Tanguay R.L., Hahn M.E., Heideman W., Peterson R.E. Two forms of aryl hydrocarbon receptor type 2 in rainbow trout (Oncorhynchus mykiss). Evidence for differential expression and enhancer specificity. J. Biol. Chem. 274:(21):1999a;15159-15166.
3. Abnet C.C., Tanguay R.L., Heideman W., Peterson R.E. Transactivation activity of human, zebrafish, and rainbow trout aryl hydrocarbon receptors expressed in COS-7 cells: greater insight into species differences in toxic potency of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners. Toxicol. Appl. Pharmacol. 159:(1):1999b;41-51.
4. Basu N., Billiard S., Fragoso N., Omoike A., Tabash S., Brown S., Hodson P. Ethoxyresorufin-O-deethylase induction in trout exposed to mixtures of polycyclic aromatic hydrocarbons. Environ. Toxicol. Chem. 20:(6):2001;1244-1251.
5. Behrens A., Schirmer K., Bols N.C., Segner H. Polycyclic aromatic hydrocarbons as inducers of cytochrome P4501A enzyme activity in the rainbow trout liver cell line, RTL-W1, and in primary cultures of rainbow trout hepatocytes. Environ. Toxicol. Chem. 20:(3):2001;632-643.
6. Billiard, S., Hodson, P., Bols., N., 1998. Relative potency of PAH for inducing CYP1A1 in juvenile trout. Paper presented at the 19th Annual SETAC Meeting, Charlotte, NC, USA.
7. Billiard S., Querbach K., Hodson P. Toxicity of retene to early life stages of two freshwater fish species. Environ. Toxicol. Chem. 18:(9):1999;2070-2077.
8. Billiard, S., Hodson, P., 2001. Toxicity of PAH to early life stages of rainbow trout. Paper presented at the 22nd Annual SETAC Meeting, Baltimore, MD, USA.
9. Billiard, S.M., 2002. Toxicological Significance of CYP1A Induction in Teleosts Exposed to Polycyclic Aromatic Hydrocarbons (PAH). Ph.D. thesis, Queen's University.
10. Bols N.C., Schirmer K., Joyce E.M., Dixon D.G., Greenberg B.M., Whyte J.J. Ability of polycyclic aromatic hydrocarbons to induce 7-ethoxyresorufin-o-deethylase activity in a trout liver cell line. Ecotoxicol. Environ. Saf. 44:(1):1999;118-228.
11. 125I]2-iodo-7,8-dibromodibenzo-p-dioxin. Mol. Pharmacol. 34:1988;229-237.
12. Brown M.M., Schneider U.A., Petrulis J.R., Bunce N.J. Additive binding of polychlorinated biphenyls and 2,3,7,8-tetrachlorodibenzo-p-dioxin to the murine hepatic Ah receptor. Toxicol. Appl. Pharmacol. 129:1994;243-251.
13. Celander M., Bremer J., Hahn M.E., Stegeman J.J. Glucocorticoid-xenobiotic interactions: dexamethasone potentiation of cytochrome P4501A induction by β-naphthoflavone in a fish hepatoma cell line (PLHC-1). Environ. Toxicol. Chem. 16:1997;900-907.
14. Dabestani R., Ivanov I.N. A compilation of physical, spectroscopic and photophysical properties of polycyclic aromatic hydrocarbons. Photochem. Photobiol. 70:(1):1999;10-34.
15. Denison M.S., Heath-Pagliuso S. The Ah receptor: a regulator of the biochemical and toxicological actions of structurally diverse chemicals. Bull. Environ. Contam. Toxicol. 61:(5):1998;557-568.
16. Dold K.M., Greenlee W.F. Filtration assay for quantitation of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) specific binding to whole cells in culture. Anal. Biochem. 184:1990;67-73.
17. Elonen G.E., Spehar R.L., Holcombe G.W., Johnson R.D., Fernandez J.D., Erickson R.J., Tietge J.E., Cook P.M. Comparative toxicity of 2,3,7,8-tetrachlorodibenzo-p-dioxin to seven freshwater fish species during early life-stage development. Environ. Toxicol. Chem. 17:(3):1998;472-483.
18. Farrell K., Safe S. Absence of positive co-operativity in the binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin to its cytosolic receptor protein. Biochem. J. 244:1987;539-546.
19. Gaddum J.H. The quantitative aspects of antagonistic drugs. J. Physiol. 89:1937;7P.
20. Gonzalez F.J., Fernandez-Salguero P. The aryl hydrocarbon receptor: studies using the AHR-null mice. Drug Metab. Dispos. 26:(12):1998;1194-1198.
21. Guiney P.D., Smolowitz R.M., Peterson R.E., Stegeman J.J. Correlation of 2,3,7,8-tetrachlorodibenzo-p-dioxin induction of cytochrome P4501A in vascular endothelium with toxicity in early life stages of lake trout. Toxicol. Appl. Pharmacol. 143:1997;256-273.
22. Hahn M.E., Lamb T.M., Schultz M.E., Smolowitz R.M., Stegeman J.J. Cytochrome P4501A induction and inhibition by 3,3,4,4-tetrachlorobiphenyl in an Ah receptor-containing fish hepatoma cell line (PLHC-1). Aquat. Toxicol. 26:1993;185-208.
23. Hahn M.E., Poland A., Glover E., Stegeman J.J. Photoaffinity labeling of the Ah receptor: phylogenetic survey of diverse vertebrate and invertebrate species. Arch. Biochem. Biophys. 310:(1):1994;218-228.
24. Hahn M.E., Woodward B.L., Stegeman J.J., Kennedy S.W. Rapid assessment of induced cytochrome P4501A (CYP1A) protein and catalytic activity in fish hepatoma cells grown in multi-well plates: Response to TCDD, TCDF, and two planar PCBs. Environ. Toxicol. Chem. 15:1996;582-591.
25. Hahn M.E. Dioxin toxicology and the aryl hydrocarbon receptor: insights from fish and other non-traditional models. Mar. Biotechnol. Suppl. 3:(1):2001;S224-S238.
26. Hankinson O. The aryl hydrocarbon receptor complex. Annu. Rev. Pharmacol. Toxicol. 35:1995;307-340.
27. Harvey R.G. Polycyclic Aromatic Hydrocarbons. 1997;667 Wiley-VCH, Inc, New York, USA.
28. Heilmann L.J., Sheen Y.Y., Bigelow S.W., Nebert D.W. The trout P450IA1: cDNA and deduced protein sequence, expression in liver, and evolutionary significance. DNA. 7:1988;379-387.
29. Hestermann, E.V., 1999. Mechanisms of Action for Aryl Hydrocarbon Receptor Ligands in the PLHC-1 Cell Line. Ph.D. thesis, Woods Hole Oceanographic Institution/Massachusetts Institute of Technology.
30. Hestermann E.V., Stegeman J.J., Hahn M.E. Relative contributions of affinity and intrinsic efficacy to aryl hydrocarbon receptor ligand potency. Toxicol. Appl. Pharmacol. 168:(2):2000;160-172.
31. Hestermann E.V., Stegeman J.J., Hahn M.E. Relationships among the cell cycle, cell proliferation, and aryl hydrocarbon receptor expression in PLHC-1 cells. Aquat. Toxicol. 58:(3-4):2002;201-213.
32. Hightower L.E., Renfro J.L. Recent applications of fish cell culture to biomedical research. J. Exp. Zool. 248:(3):1988;290-302.
33. Jensen B.A., Hahn M.E. cDNA cloning and characterization of a high affinity aryl hydrocarbon receptor in a cetacean, the beluga, Delphinapterus leucas. Toxicol. Sci. 64:2001;41-56.
34. Karchner S.I., Powell W.H., Hahn M.E. Identification and functional characterization of two highly divergent aryl hydrocarbon receptors (AHR1 and AHR2) in the teleost Fundulus heteroclitus. Evidence for a novel subfamily of ligand-binding basic helix loop helix-Per-ARNT-Sim (bHLH-PAS) factors. J. Biol. Chem. 274:(47):1999;33814-33824.
35. Kiparissis, Y., Blazeski, S., Hodson, P., Cai, X., Snieckus, V., 2001. Embryotoxicity of alkyl-substituted PAHs. Poster presented at the 22nd Annual SETAC Meeting, Baltimore, MD, USA.
36. Lahvis G.P., Lindell S.L., Thomas R.S., et al. Portosystemic shunting and persistent fetal vascular structures in aryl hydrocarbon receptor-deficient mice. Proc. Natl. Acad. Sci. 97:(19):2000;10442-10447.
37. Lee L.E.J., Clemons J.H., Bechtel D.G., et al. Development and characterization of a rainbow trout liver cell line expressing cytochrome P450-dependent monooxygenase activity. Cell Biol. Toxicol. 9:1993;279-294.
38. 3H]2,3,7,8-tetrachlordibenzo-p-dioxin binding to Ah receptor in a rainbow trout hepatoma cell line. Toxicol. Appl. Pharmacol. 106:(1):1990;53-62.
39. Ma Q., Whitlock J.P. Jr. A novel cytoplasmic protein that interacts with the Ah receptor, contains tetratricopeptide repeat motifs, and augments the transcriptional response to 2,3,7,8-tetrachlorodibenzo-p-dioxin. J. Biol. Chem. 272:(14):1997;8878-8884.
40. Martin R.G., Ames B.N. A method for determining the sedimentation behaviour of enzymes: application to protein mixtures. J. Biol. Chem. 236:1961;1372-1379.
41. Marty G.D., Short J.W., Dambach D.M., et al. Histopathology and cytogenetic evaluation of Pacific herring larvae exposed to petroleum hydrocarbons in the laboratory or in Prince William Sound, Alaska, after the Exxon Valdez oil spill. Can. J. Zool. 75:1997;989-1007.
42. McElroy A.E., Farrington J.W., Teal J.M. Bioavailability of polycyclic aromatic hydrocarbons in the aquatic environment. Varanasai U., Metabolism of Polycyclic Aromatic Hydrocarbons in the Aquatic Environment. 1989;CRC Press Inc, USA.
43. Piskorska-Pliszczynska J., Keys B., Safe S., Newman M.S. The cytosolic receptor binding affinities and AHH induction potencies of 29 polynuclear aromatic hydrocarbons. Toxicol. Lett. 34:1986;67-74.
44. Poland A., Knutson J.C. 2,3,7,8-Tetrachlorodibenzo-p-dioxin and related halogenated aromatic hydrocarbons: Examination of the mechanism of toxicity. Annu. Rev. Pharmacol. Toxicol. 22:1982;517-554.
45. Poland A., Glover E. 2,3,7,8-Tetrachlorodibenzo-p-dioxin: Segregation of toxicity with the Ah locus. Mol. Pharmacol. 17:1979;86-94.
46. Pollenz R.S., Necela B. Characterization of two continuous cell lines derived from Onchorhynchus mykiss for models of aryl-hydrocarbon-receptor-mediated signal transduction. Direct comparison to the mammalian Hepa-1c1c7 cell line. Aquat. Toxicol. 41:1998;31-49.
47. Readman J.W., Mantoura R.F., Rhead M.M., Brown L. Aquatic distribution and heterotrophic degradation of polycyclic aromatic hydrocarbons (PAH) in the Tamar estuary. Est. Coast. Shelf Sci. 14:1982;369.
48. Riddick D.S., Huang Y., Harper P.A., Okey A.B. 2,3,7,8-Tetrachlorodibenzo-p-dioxin versus 3-methycholanthrene-comparative studies of Ah receptor binding, transformation, and induction of CYP1A1. J. Biol. Chem. 269:1994;12118-12128.
49. Roy N.K., Wirgin I. Characterization of the aromatic hydrocarbon receptor gene and its expression in Atlantic tomcod. Arch. Biochem. Biophys. 344:(2):1997;373-386.
50. Safe S. Limitations of the toxic equivalency factor approach for risk assessment of TCDD and related compounds. Teratog. Carcinog. Mutagen. 17:(4-5):1998;285-304.
51. Schmidt J.V., Bradfield C.A. Ah receptor signaling pathways. Annu. Rev. Cell Dev. Biol. 12:1996;55-89.
52. Schneider U.A., Brown M.M., Logan R.A., Millar L.C., Bunce N.J. Screening assay for dioxin-like compounds based on competitive binding to the murine hepatic Ah receptor. 1. Assay development. Environ. Sci. Technol. 29:1995;2595-2602.
53. Smith P.K., Krohn R.I., Hermanson G.T., et al. Measurement of protein using bicinchoninic acid. Anal. Biochem. 150:1985;76-85.
54. Stegeman J.J., Miller M.R., Hinton D.E. Cytochrome P450IA1 induction and localization in endothelium of vertebrate (teleost) heart. Mol. Pharmacol. 36:(5):1989;723-729.
55. Stegeman J.J., Hahn M.E. Biochemistry and molecular biology of monooxygenases: current perspectives on forms, functions, and regulation of cytochrome P450 in aquatic species. Malins D.C., Ostrander G.K., Aquatic Toxicology: Molecular, Biochemical, and Cellular Perspectives. 1994;87-206 Lewis Publishers, Boca Raton, FL, USA.
56. 125I]iodo-7,8-dibromodibenzo-p-dioxin in cell culture. Toxicol. Lett. 58:(1):1991;85-95.
57. Tanguay R.L., Abnet C.C., Heideman W., Peterson R.E. Cloning and characterization of the zebrafish (Danio rerio) aryl hydrocarbon receptor. Biochim. Biophys. Acta. 1444:(1):1999;35-48.
58. Tsui H.W., Okey A.B. Rapid vertical tube rotor gradient assay for binding of 2,3,7,8-tetrachlorodibenzo-p-dioxin to the Ah receptor. Can. J. Physiol. Pharmacol. 59:(9):1981;927-931.
59. Van den Berg M., Birnbaum L., Bosveld A.T.C., et al. Toxic equivalency factors (TEFs) for PCBs, PCDDs, PCDFs for humans and wildlife. Environ. Health Perspect. 106:(12):1998;775-792.
60. Villeneuve D.L., Khim J.S., Kannan K., Giesy J.P. Relative potencies of individual polycyclic aromatic hydrocarbons to induce dioxin-like and estrogenic responses in three cell lines. Environ. Toxicol. 17:2002;128-137.
61. Walker M.K., Peterson R.E. Potencies of polychlorinated dibenzo-p-dioxin, dibenzofuran, and biphenyl congeners, relative to 2,3,7,8-tetrachlorodibenzo-p-dioxin, for producing early life stage mortality in rainbow trout (Oncorhynchus mykiss). Aquat. Toxicol. 21:1991;219-238.
62. Willett K., Steinberg M., Thomsen J., et al. Exposure of killifish to benzo[a]pyrene: comparative metabolism, DNA adduct formation and aryl hydrocarbon (Ah) receptor agonist activities. Comp. Biochem. Physiol. 112B:1995;93-103.