New approaches to assess the transthyretin binding capacity of bioactivated thyroid hormone disruptors

Toxicological Sciences

Volumn 130, Issue 1, 2012, Pages 94-105

  Montaño, Mauricio ^a,b   Cocco, Emmanuelle ^a   Guignard, Cedric ^a   Marsh, Göran ^c   Hoffmann, Lucien ^a   Bergman, Åke ^c   Gutleb, Arno Christian ^a   Murk, Albertinka Jacoba ^b  

^a LUXEMBOURG INSTITUTE OF SCIENCE AND TECHNOLOGY   (Luxembourg)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c STOCKHOLM UNIVERSITY   (Sweden)

Author keywords

Competition; Endocrine disruption; In vitro metabolism; OH metabolites; POPs; Thyroid hormone transport

Indexed keywords

CHOLESTEROL; ENDOCRINE DISRUPTOR; POLYBROMINATED DIPHENYL ETHER; POLYCHLORINATED BIPHENYL; PREALBUMIN; SATURATED FATTY ACID; THYROID HORMONE; THYROXINE; UNSATURATED FATTY ACID;

ANIMAL TISSUE; ARTICLE; CHROMATOGRAPHY; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; EXTRACTION; FLUORESCENCE; HORMONE TRANSPORT; HYDROXYLATION; IN VITRO STUDY; NONHUMAN; POLLUTANT; PROTEIN BINDING; QUANTITATIVE ANALYSIS; RADIOASSAY; RAT;

ANIMALS; CHOLESTEROL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ENDOCRINE DISRUPTORS; ENVIRONMENTAL POLLUTANTS; FATTY ACIDS; FATTY ACIDS, UNSATURATED; MICROSOMES, LIVER; POLYBROMINATED BIPHENYLS; POLYCHLORINATED BIPHENYLS; PREALBUMIN; PROTEIN BINDING; RATS; RATS, SPRAGUE-DAWLEY; THYROXINE;

EID: 84867765495     PISSN: 10966080     EISSN: 10960929     Source Type: Journal    
DOI: 10.1093/toxsci/kfs228     Document Type: Article

References (42)

1. Ballschmiter, K., and Zell, M. (1980). Analysis of polychlorinated biphenyls (PCB) by glass capillary gas chromatography. Fresen. J. Anal. Chem. 302, 20-31.
2. Belina, H., Cooper, S. D., Farkas, R., and Feuer, G. (1975). Sex difference in the phospholipid composition of rat liver microsomes. Biochem. Pharmacol. 24, 301-303.
3. Cao, J., Guo, L. H., Wan, B., and Wei, Y. (2011). In vitro fluorescence displacement investigation of thyroxine transport disruption by bisphenol A. J. Environ. Sci. 23, 315-321.
4. Cao, J., Lin, Y., Guo, L. H., Zhang, A. Q., Wei, Y., and Yang, Y. (2010). Structurebased investigation on the binding interaction of hydroxylated polybrominated diphenyl ethers with thyroxine transport proteins. Toxicology 277, 20-28.
5. Cheng, S. Y., Pages, R. A., Saroff, H. A., Edelhoch, H., and Robbins, J. (1977). Analysis of thyroid hormone binding to human serum prealbumin by 8-anilinonaphthalene-1-sulfonate fluorescence. Biochemistry 16, 3707-3713.
6. Dingemans, M. M., van den Berg, M., and Westerink, R. H. (2011). Neurotoxicity of brominated flame retardants: (In)direct effects of parent and hydroxylated polybrominated diphenyl ethers on the (developing) nervous system. Environ. Health Perspect. 119, 900-907.
7. Escher, B. I., and Fenner, K. (2011). Recent advances in environmental risk assessment of transformation products. Environ. Sci. Technol. 45, 3835-3847.
8. Freitas, J., Cano, P., Craig-Veit, C., Goodson, M. L., Furlow, J. D., and Murk, A. J. (2011). Detection of thyroid hormone receptor disruptors by a novel stable in vitro reporter gene assay. Toxicol. In Vitro 25, 257-266.
9. Gebbink, W. A., Sonne, C., Dietz, R., Kirkegaard, M., Riget, F. F., Born, E. W., Muir, D. C., and Letcher, R. J. (2008). Tissue-specific congener composition of organohalogen and metabolite contaminants in East Greenland polar bears (Ursus maritimus). Environ. Pollut. 152, 621-629.
10. Gutleb, A. C., Cenijn, P., Velzen, M., Lie, E., Ropstad, E., Skaare, J. U., Malmberg, T., Bergman, A., Gabrielsen, G. W., and Legler, J. (2010). In vitro assay shows that PCB metabolites completely saturate thyroid hormone transport capacity in blood of wild polar bears (Ursus maritimus). Environ. Sci. Technol. 44, 3149-3154.
11. Hamers, T., Kamstra, J. H., Sonneveld, E., Murk, A. J., Kester, M. H., Andersson, P. L., Legler, J., and Brouwer, A. (2006). In vitro profiling of the endocrine-disrupting potency of brominated flame retardants. Toxicol. Sci. 92, 157-173.
12. Hamers, T., Kamstra, J. H., Sonneveld, E., Murk, A. J., Visser, T. J., Van Velzen, M. J., Brouwer, A., and Bergman, A. (2008). Biotransformation of brominated flame retardants into potentially endocrine-disrupting metabolites, with special attention to 2,2',4,4'-tetrabromodiphenyl ether (BDE-47). Mol. Nutr. Food Res. 52, 284-298.
13. Harju, M., Hamers, T., Kamstra, J. H., Sonneveld, E., Boon, J. P., Tysklind, M., and Andersson, P. L. (2007). Quantitative structure-activity relationship modeling on in vitro endocrine effects and metabolic stability involving 26 selected brominated flame retardants. Environ. Toxicol. Chem. 26, 816-826.
14. Hovander, L., Athanasiadou, M., Asplund, L., Jensen, S., and Wehler, E. K. (2000). Extraction and cleanup methods for analysis of phenolic and neutral organohalogens in plasma. J. Anal. Toxicol. 24, 696-703.
15. Kelly, B. C., Ikonomou, M. G., Blair, J. D., and Gobas, F. A. (2008). Bioaccumulation behaviour of polybrominated diphenyl ethers (PBDEs) in a Canadian Arctic marine food web. Sci. Total Environ. 401, 60-72.
16. Lans, M. C., Klasson-Wehler, E., Willemsen, M., Meussen, E., Safe, S., and Brouwer, A. (1993). Structure-dependent, competitive interaction of hydroxy-polychlorobiphenyls,-dibenzo-p-dioxins and-dibenzofurans with human transthyretin. Chem. Biol. Interact. 88, 7-21.
17. Lans, M. C., Spiertz, C., Brouwer, A., and Koeman, J. H. (1994). Different competition of thyroxine binding to transthyretin and thyroxine-binding globulin by hydroxy-PCBs, PCDDs and PCDFs. Eur. J. Pharm-Environ. 270, 129-136.
18. Marchesini, G. R., Meimaridou, A., Haasnoot, W., Meulenberg, E., Albertus, F., Mizuguchi, M., Takeuchi, M., Irth, H., and Murk, A. J. (2008). Biosensor discovery of thyroxine transport disrupting chemicals. Toxicol. Appl. Pharmacol. 232, 150-160.
19. Marchesini, G. R., Meulenberg, E., Haasnoot, W., Mizuguchi, M., and Irth, H. (2006). Biosensor recognition of thyroid-disrupting chemicals using transport proteins. Anal. Chem. 78, 1107-1114.
20. Marsh, G., Athanasiadou, M., Athanassiadis, I., and Sandholm, A. (2006). Identification of hydroxylated metabolites in 2,2',4,4'-tetrabromodiphenyl ether exposed rats. Chemosphere 63, 690-697.
21. Marsh, G., Stenutz, R., and Bergman, A. (2003). Synthesis of hydroxylated and methoxylated polybrominated diphenyl ethers-Natural products and potential polybrominated diphenyl ether metabolites. Eur. J. Org. Chem. 2003, 2566-2576.
22. Meerts, I. A., Assink, Y., Cenijn, P. H., Van Den Berg, J. H., Weijers, B. M., Bergman, A., Koeman, J. H., and Brouwer, A. (2002). Placental transfer of a hydroxylated polychlorinated biphenyl and effects on fetal and maternal thyroid hormone homeostasis in the rat. Toxicol. Sci. 68, 361-371.
23. Meerts, I. A., Letcher, R. J., Hoving, S., Marsh, G., Bergman, A., Lemmen, J. G., van der Burg, B., and Brouwer, A. (2001). In vitro estrogenicity of polybrominated diphenyl ethers, hydroxylated PDBEs, and polybrominated bisphenol A compounds. Environ. Health Perspect. 109, 399-407.
24. Meerts, I. A., van Zanden, J. J., Luijks, E. A., van Leeuwen-Bol, I., Marsh, G., Jakobsson, E., Bergman, A., and Brouwer, A. (2000). Potent competitive interactions of some brominated flame retardants and related compounds with human transthyretin in vitro. Toxicol. Sci. 56, 95-104.
25. Mills, S. A., III, Thal, D. I., and Barney, J. (2007). A summary of the 209 PCB congener nomenclature. Chemosphere 68, 1603-1612.
26. Möller, M., and Denicola, A. (2002). Study of protein-ligand binding by fluorescence. Biochem. Mol. Biol. Edu. 30, 309-312.
27. Morse, D. C., Groen, D., Veerman, M., van Amerongen, C. J., Koëter, H. B., Smits van Prooije, A. E., Visser, T. J., Koeman, J. H., and Brouwer, A. (1993). Interference of polychlorinated biphenyls in hepatic and brain thyroid hormone metabolism in fetal and neonatal rats. Toxicol. Appl. Pharmacol. 122, 27-33.
28. Morse, D. C., Wehler, E. K., van de Pas, M., de Bie, A. T., van Bladeren, P. J., and Brouwer, A. (1995). Metabolism and biochemical effects of 3,3',4,4'-tetrachlorobiphenyl in pregnant and fetal rats. Chem. Biol. Interact. 95, 41-56.
29. Murk, A., Morse, D., Boon, J., and Brouwer, A. (1994). 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. Pharm-Environ. 270, 253-261.
30. Murk, A. J., Legler, J., Denison, M. S., Giesy, J. P., van de Guchte, C., and Brouwer, A. (1996). Chemical-activated luciferase gene expression (CALUX): A novel in vitro bioassay for Ah receptor active compounds in sediments and pore water. Fundam. Appl. Toxicol. 33, 149-160.
31. Nilsson, S. F., and Peterson, P. A. (1975). Studies on thyroid hormone-binding proteins. I. The subunit structure of human thyroxine-binding globulin and its interaction with ligands. J. Biol. Chem. 250, 8543-8553.
32. Nilsson, S. F., Rask, L., and Peterson, P. A. (1975). Studies on thyroid hormone-binding proteins. II. Binding of thyroid hormones, retinol-binding protein, and fluorescent probes to prealbumin and effects of thyroxine on prealbumin subunit self association. J. Biol. Chem. 250, 8554-8563.
33. Schriks, M., Vrabie, C. M., Gutleb, A. C., Faassen, E. J., Rietjens, I. M., and Murk, A. J. (2006). T-screen to quantify functional potentiating, antagonistic and thyroid hormone-like activities of poly halogenated aromatic hydrocarbons (PHAHs). Toxicol. In Vitro 20, 490-498.
34. Shaw, W., Hubert, I. L., and Spierto, F. W. (1976). Interference of fatty acids in the competitive protein-binding assay for serum thyroxine. Clin. Chem. 22, 673-678.
35. Simon, E., Lamoree, M. H., Hamers, T., Weiss, J. M., Balaam, J., de Boer, J., and Leonards, P. E. (2010). Testing endocrine disruption in biota samples: A method to remove interfering lipids and natural hormones. Environ. Sci. Technol. 44, 8322-8329.
36. Simon, E., Bytingsvik, J., Jonker, W., Leonards, P. E. G., de Boer, J., Bjørn, M. J., Lie, E., Aars, J., Hamers, T., and Lamoree, M. H. (2011). Blood plasma sample preparation method for the assessment of thyroid hormone-disrupting potency in effect-directed analysis. Environ. Sci. Technol. 45, 7936-7944.
37. Sjödin, A., Hagmar, L., Klasson-Wehler, E., Björk, J., and Bergman, A. (2000). Influence of the consumption of fatty Baltic Sea fish on plasma levels of halogenated environmental contaminants in Latvian and Swedish men. Environ. Health Perspect. 108, 1035-1041.
38. Song, R., He, Y., Murphy, M. B., Yeung, L. W. Y., Yu, R. M. K., Lam, M. H. W., Lam, P. K. S., Hecker, M., Giesy, J. P., Wu, R. S. S., et al. (2008). Effects of fifteen PBDE metabolites, DE71, DE79 and TBBPA on steroidogenesis in the H295R cell line. Chemosphere 71, 1888-1894.
39. Tabachnick, M., and Korcek, L. (1986). Effect of long-chain fatty acids on the binding of thyroxine and triiodothyronine to human thyroxine-binding globulin. Biochim. Biophys. Acta Gen. Subj. 881, 292-296.
40. Waskell, L., Koblin, D., and Canova-Davis, E. (1982). The lipid composition of human liver microsomes. Lipids 17, 317-320.
41. Weiss, J. M., Andersson, P. L., Lamoree, M. H., Leonards, P. E., van Leeuwen, S. P., and Hamers, T. (2009). Competitive binding of poly-and perfluorinated compounds to the thyroid hormone transport protein transthyretin. Toxicol. Sci. 109, 206-216.
42. Yung, C. C., and Prusoff, W. H. (1973). Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem. Pharmacol. 22, 3099-3108.