Structure-activity relationships for hydroxylated polychlorinated biphenyls as inhibitors of the sulfation of dehydroepiandrosterone catalyzed by human hydroxysteroid sulfotransferase SULT2A1

Chemical Research in Toxicology

Volumn 24, Issue 10, 2011, Pages 1720-1728

  Ekuase, Edugie J ^a   Liu, Yungang ^a   Lehmler, Hans Joachim ^a   Robertson, Larry W ^a   Duffel, Michael W ^a  

^a UNIVERSITY OF IOWA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCHLORINATED BIPHENYL; POLYCHLORINATED BIPHENYL DERIVATIVE; PRASTERONE; SULFOTRANSFERASE; SULFOTRANSFERASE 2A1; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL INTERACTION; CONTROLLED STUDY; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; NONHUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SULFATION;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DEHYDROEPIANDROSTERONE; ENVIRONMENTAL POLLUTANTS; HUMANS; HYDROXYLATION; POLYCHLORINATED BIPHENYLS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECOMBINANT PROTEINS; SULFATES; SULFOTRANSFERASES;

MAMMALIA;

EID: 80054762464     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx200260h     Document Type: Article

References (49)

1. Hansen, L. G. (1998) Stepping backward to improve assessment of PCB congener toxicities Environ. Health Perspect. 106 (Suppl. 1) 171-189 (Pubitemid 28196043)
2. Holoubek, I., Kocan, A., Holoubkova, I., Kohoutek, J., and Falandysz, J. (2001) Contaminated Sites Worldwide: The Case of the Central and Eastern European Countries, in PCBs: Recent Advances in Environmental Toxicology and Health Effects (Robertson, L. W. and Hansen, L. G., Eds.) pp 81-83, University of Kentucky Press, Lexington, KY.
3. Hornbuckle, K. and Robertson, L. (2010) Polychlorinated biphenyls (PCBs): sources, exposures, toxicities Environ. Sci. Technol. 44, 2749-2751
4. Ludewig, G., Esch, H., and Robertson, L. W. (2007) Polyhalogenierte Bi- und Terphenyle, Chapter 20, Wiley-VCH, Weinheim, Germany.
5. Safe, S. H. (1994) Polychlorinated biphenyls (PCBs): environmental impact, biochemical and toxic responses, and implications for risk assessment Crit. Rev. Toxicol. 24, 87-149 (Pubitemid 24186961)
6. Safe, S. (1984) Polychlorinated biphenyls (PCBs) and polybrominated biphenyls (PBBs): biochemistry, toxicology, and mechanism of action Crit. Rev. Toxicol. 13, 319-395 (Pubitemid 14005347)
7. Currado, G. M. and Harrad, S. (1998) Comparison of polychlorinated biphenyl concentrations in indoor and outdoor air and the potential significance of inhalation as a human exposure pathway Environ. Sci. Technol. 32, 3043-3047 (Pubitemid 28485235)
8. Harrad, S., Hazrati, S., and Ibarra, C. (2006) Concentrations of polychlorinated biphenyls in indoor air and polybrominated diphenyl ethers in indoor air and dust in Birmingham, United Kingdom: implications for human exposure Environ. Sci. Technol. 40, 4633-4638 (Pubitemid 44157198)
9. Herrick, R. F., McClean, M. D., Meeker, J. D., Baxter, L. K., and Weymouth, G. A. (2004) An unrecognized source of PCB contamination in schools and other buildings Environ. Health Perspect. 112, 1051-1053 (Pubitemid 39029157)
10. Hu, D., Martinez, A., and Hornbuckle, K. C. (2008) Discovery of non-aroclor PCB (3,3′-dichlorobiphenyl) in Chicago air Environ. Sci. Technol. 42, 7873-7877
11. Martinez, A., Wang, K., and Hornbuckle, K. C. (2010) Fate of PCB congeners in an industrial harbor of Lake Michigan Environ. Sci. Technol. 44, 2803-2808
12. Wethington, D. M., III and Hornbuckle, K. C. (2005) Milwaukee, WI, as a source of atmospheric PCBs to Lake Michigan Environ. Sci. Technol. 39, 57-63 (Pubitemid 40066273)
13. Ludewig, G., Lehmann, L., Esch, H., and Robertson, L. W. (2008) Metabolic Activation of PCBs to Carcinogens in Vivo: A Review Environ. Toxicol. Pharmacol. 25, 241-246
14. James, M. O. (2001) Polychlorinated Biphenyls: Metabolism and Metabolites, in PCBs: Recent Advances in Environmental Toxicology and Health Effects (Robertson, L. W. and Hansen, L. G., Eds.) pp 35-46, The University Press of Kentucky, Lexington, KY.
15. Bergman, A., Klasson-Wehler, E., and Kuroki, H. (1994) Selective retention of hydroxylated PCB metabolites in blood Environ. Health Perspect. 102, 464-469 (Pubitemid 24200106)
16. Dirtu, A. C., Jaspers, V. L., Cernat, R., Neels, H., and Covaci, A. (2010) Distribution of PCBs, their hydroxylated metabolites, and other phenolic contaminants in human serum from two European countries Environ. Sci. Technol. 44, 2876-2883
17. Fängström, B., Athanasiadou, M., Grandjean, P., Weihe, P., and Bergman, Å. (2002) Hydroxylated PCB metabolites and PCBs in serum from pregnant Faroese women Environ. Health Perspect. 110, 895-899
18. Gabrio, T., Piechotowski, I., Wallenhorst, T., Klett, M., Cott, L., Friebel, P., Link, B., and Schwenk, M. (2000) PCB-blood levels in teachers, working in PCB-contaminated schools Chemosphere 40, 1055-1062 (Pubitemid 30120713)
19. Park, J. S., Bergman, A., Linderholm, L., Athanasiadou, M., Kocan, A., Petrik, J., Drobna, B., Trnovec, T., Charles, M. J., and Hertz-Picciotto, I. (2008) Placental transfer of polychlorinated biphenyls, their hydroxylated metabolites and pentachlorophenol in pregnant women from eastern Slovakia Chemosphere 70, 1676-1684
20. Sandau, C. D., Ayotte, P., Dewailly, E., Duffe, J., and Norstrom, R. J. (2000) Analysis of hydroxylated metabolites of PCBs (OH-PCBs) and other chlorinated phenolic compounds in whole blood from Canadian inuit Environ. Health Perspect. 108, 611-616 (Pubitemid 30657866)
21. 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 (Pubitemid 23205415)
22. Schuur, A. G., Brouwer, A., Bergman, A., Coughtrie, M. W., and Visser, T. J. (1998) Inhibition of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls Chem.-Biol. Interact 109, 293-297 (Pubitemid 28161121)
23. Schuur, A. G., van Leeuwen-Bol, I., Jong, W. M., Bergman, A., Coughtrie, M. W., Brouwer, A., and Visser, T. J. (1998) In vitro inhibition of thyroid hormone sulfation by polychlorobiphenylols: isozyme specificity and inhibition kinetics Toxicol. Sci. 45, 188-194 (Pubitemid 28516659)
24. Kester, M. H., Bulduk, S., Tibboel, D., Meinl, W., Glatt, H., Falany, C. N., Coughtrie, M. W., Bergman, A., Safe, S. H., Kuiper, G. G., Schuur, A. G., Brouwer, A., and Visser, T. J. (2000) Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs Endocrinology 141, 1897-1900 (Pubitemid 32274420)
25. Falany, C. N., Comer, K. A., Dooley, T. P., and Glatt, H. (1995) Human dehydroepiandrosterone sulfotransferase. Purification, molecular cloning, and characterization Ann. N.Y. Acad. Sci. 774, 59-72 (Pubitemid 26140360)
26. Falany, C. N., Vazquez, M. E., and Kalb, J. M. (1989) Purification and characterization of human liver dehydroepiandrosterone sulphotransferase Biochem. J. 260, 641-646 (Pubitemid 19155657)
27. Otterness, D. M., Wieben, E. D., Wood, T. C., Watson, R. W. G., Madden, B. J., McCormick, D. J., and Weinshilboum, R. M. (1992) Human liver dehydroepiandrosterone sulfotransferase: molecular cloning and expression of cDNA Mol. Pharmacol. 41, 865-872 (Pubitemid 23023329)
28. Liu, Y., Apak, T. I., Lehmler, H. J., Robertson, L. W., and Duffel, M. W. (2006) Hydroxylated polychlorinated biphenyls are substrates and inhibitors of human hydroxysteroid sulfotransferase SULT2A1 Chem. Res. Toxicol. 19, 1420-1425 (Pubitemid 44863483)
29. Lehmler, H. J. and Robertson, L. W. (2001) Synthesis of hydroxylated PCB metabolites with the Suzuki coupling Chemosphere 45, 1119-1127 (Pubitemid 32963482)
30. Sekura, R. D. (1981) Adenosine 3′-phosphate 5′-phosphosulfate Methods Enzymol. 77, 413-415
31. Sheng, J. J. and Duffel, M. W. (2003) Enantioselectivity of human hydroxysteroid sulfotransferase ST2A3 with naphthyl-1-ethanols Drug Metab. Dispos. 31, 697-700 (Pubitemid 36617655)
32. Gulcan, H. O., Liu, Y., and Duffel, M. W. (2008) Pentachlorophenol and other chlorinated phenols are substrates for human hydroxysteroid sulfotransferase hSULT2A1 Chem. Res. Toxicol. 21, 1503-1508
33. Bensadoun, A. and Weinstein, D. (1976) Assay of proteins in the presence of interfering materials Anal. Biochem. 70, 241-250
34. Sekura, R. D. and Jakoby, W. B. (1979) Phenol Sulfotransferases J. Biol. Chem. 254, 5658-5663
35. Sheng, J., Sharma, V., and Duffel, M. W. (2001) Measurement of Aryl and Alcohol Sulfotransferase Activity, Current Protocols in Toxicology, pp 4.5.1-4.5.9, John Wiley and Sons, Inc., New York.
36. Gulcan, H. O. and Duffel, M. W. (2011) Substrate inhibition in human hydroxysteroid sulfotransferase SULT2A1: studies on the formation of catalytically non-productive enzyme complexes Arch. Biochem. Biophys. 507, 232-240
37. Duffel, M. W., Binder, T. P., and Rao, S. I. (1989) Assay of purified aryl sulfotransferase suitable for reactions yielding unstable sulfuric acid esters Anal. Biochem. 183, 320-324 (Pubitemid 20016266)
38. Cramer, R. D., III, Patterson, D. E., and Bunce, J. D. (1988) Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins J. Am. Chem. Soc. 110, 5959-5967
39. Duffel, M. W. (2010) Sulfotransferases, In Comprehensive Toxicology (Guengerich, F. P. and McQueen, C. A., Eds.) Vol. 4, Biotransformation, pp 367-384, Elsevier, Oxford.
40. Duffel, M. W., Marshall, A. D., McPhie, P., Sharma, V., and Jakoby, W. B. (2001) Enzymatic aspects of the phenol (aryl) sulfotransferases Drug Metab. Rev. 33, 369-395 (Pubitemid 33136269)
41. Gamage, N., Barnett, A., Hempel, N., Duggleby, R. G., Windmill, K. F., Martin, J. L., and McManus, M. E. (2006) Human sulfotransferases and their role in chemical metabolism Toxicol. Sci. 90, 5-22 (Pubitemid 43264722)
42. Glatt, H., Boeing, H., Engelke, C. E., Ma, L., Kuhlow, A., Pabel, U., Pomplun, D., Teubner, W., and Meinl, W. (2001) Human cytosolic sulphotransferases: genetics, characteristics, toxicological aspects Mutat. Res. 482, 27-40 (Pubitemid 32787079)
43. Pacifici, G. M. and Coughtrie, M. W., Eds. (2005) Human Cytosolic Sulfotransferases, CRC Press, Boca Raton, FL.
44. Blat, Y. (2010) Non-competitive inhibition by active site binders Chem. Biol. Drug. Des. 75, 535-540
45. Cook, I. T., Leyh, T. S., Kadlubar, S. A., and Falany, C. N. (2010) Lack of substrate inhibition in a monomeric form of human cytosolic SULT2A1 Horm. Mol. Biol. Clin. Invest. 3, 357-366
46. Cook, I. T., Leyh, T. S., Kadlubar, S. A., and Falany, C. N. (2010) Structural rearrangement of SULT2A1: effects on dehydroepiandrosterone and raloxifene sulfation Horm. Mol. Biol. Clin. Invest. 1, 81-87
47. Zhou, M., Rehse, P., Chang, H. J., Luu-The, V., and Lin, S. X. (2001) Crystallization and preliminary crystallographic results of apo and complex forms of human dehydroepiandrosterone sulfotransferase Acta Crystallogr., Sect. D 57, 1630-1633 (Pubitemid 33037727)
48. Labrie, F., Belanger, A., Cusan, L., Gomez, J.-L., and Candas, B. (1997) Marked decline in serum concentrations of adrenal C19 sex steroid precursors and conjugated androgen metabolites during aging J. Clin. Endocrinol. Metab. 82, 2396-2402 (Pubitemid 27337846)
49. Guvenius, D. M., Aronsson, A., Ekman-Ordeberg, G., Bergman, A., and Noren, K. (2003) Human prenatal and postnatal exposure to polybrominated diphenyl ethers, polychlorinated biphenyls, polychlorobiphenylols, and pentachlorophenol Environ. Health Perspect. 111, 1235-1241 (Pubitemid 36939407)