An efficient approach to sulfate metabolites of polychlorinated biphenyls

Environment International

Volumn 36, Issue 8, 2010, Pages 843-848

  Li, Xueshu ^a   Parkin, Sean ^b   Duffel, Michael W ^a   Robertson, Larry W ^a   Lehmler, Hans Joachim ^a  

^a UNIVERSITY OF IOWA   (United States)

^b UNIVERSITY OF KENTUCKY   (United States)

Author keywords

2,2,2 Trichloroethyl (TCE) group; Biaryls; Metabolites; Polychlorinated biphenyls (PCBs); Sulfates

Indexed keywords

CHLORINE; HYDROXYLATION; METABOLITES; POLYCHLORINATED BIPHENYLS; SALTS; SULFUR COMPOUNDS; X RAY DIFFRACTION;

2,2,2-TRICHLOROETHYL (TCE) GROUP; BIARYLS; BORON TRIBROMIDE; CHLORINATED BENZENES; PERSISTENT ORGANIC POLLUTANT (POP); POLYCHLORINATED BIPHENYL (PCBS); QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP STUDIES; SULFATES;

ORGANIC POLLUTANTS;

2,2,2 TRICHLOROETHYL CHLOROSULFATE; ANISOLE DERIVATIVE; BORON TRIBROMIDE; BORONIC ACID DERIVATIVE; POLYCHLORINATED BIPHENYL DERIVATIVE; SULFATE; SULFURIC ACID 4' CHLOROBIPHENYL 4 YL 2,2,2 TRICHLOROETHYL ESTER; SULFURIC ACID MONO(4' CHLOROBIPHENYL 4 YL)ESTER; UNCLASSIFIED DRUG;

CRYSTAL STRUCTURE; METABOLITE; PCB; SULFATE; X-RAY DIFFRACTION;

ARTICLE; BROMINATION; CHEMICAL BOND; CHEMICAL COMPOSITION; CHLORINATION; CROSS COUPLING REACTION; CRYSTAL STRUCTURE; DEMETHYLATION; DETOXIFICATION; HYDROXYLATION; METABOLITE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SULFATION; SYNTHESIS; X RAY DIFFRACTION;

EID: 77957244029     PISSN: 01604120     EISSN: 18736750     Source Type: Journal    
DOI: 10.1016/j.envint.2009.02.005     Document Type: Article

References (40)

1. Bergman A., Klasson-Wehler E., Kuroki H. Selective retention of hydroxylated PCB metabolites in blood. Environ Health Perspect 1994, 102:464-469.
2. 6S. J Mol Struct 2005, 734:205-209.
3. Gunnarsson G.T., Desai U.R. Interaction of designed sulfated flavanoids with antithrombin: lessons on the design of organic activators. J Med Chem 2002, 45:4460-4470.
4. Gunnarsson G.T., Desai U.R. Exploring new non-sugar sulfated molecules as activators of antithrombin. Bioorg Med Chem Lett 2003, 13:679-683.
5. Hansen L.G. The ortho side of PCBs: occurrence and disposition 1999, Kluwer Academic Publishers, Boston.
6. Hanson S.R., Whalen L.J., Wong C.H. Synthesis and evaluation of general mechanism-based inhibitors of sulfatases based on (difluoro)methyl phenyl sulfate and cyclic phenyl sulfamate motifs. Bioorg Med Chem 2006, 14:8386-8395.
7. 35S-labelled aryl sulphate esters for metabolic studies. Biochem Pharmacol 1969, 18:173-180.
8. Hedayatu M., Leveque J.C., Denivell L. Action of sulfuryl chloride on some phenols and alcohols - alkylated and arylated phenol chlorosulfates. C R Acad Sci, Paris Ser C 1971, 273:1444-1447.
9. Hovander L., Linderholm L., Athanasiadou M., Athanassiadis I., Bignert A., Faengstroem B., et al. Levels of PCBs and their metabolites in the serum of residents of a highly contaminated area in eastern Slovakia. Environ Sci Technol 2006, 40:3696-3703.
10. James M.O. Polychlorinated biphenyls: metabolism and metabolites. PCBs: recent advances in environmental toxicology and health effects 2001, 35-46. University of Kentucky Press, Lexington, KY. L.W. Robertson, L.G. Hansen (Eds.).
11. Kester M.H.A., Bulduk S., Tibboel D., Meinl W., Glatt H., Falany C.N., et al. Potent inhibition of estrogen sulfotransferase by hydroxylated PCB metabolites: a novel pathway explaining the estrogenic activity of PCBs. Endocrinology 2000, 141:1897-1900.
12. Kodavanti P.R.S. Intracellular signaling and developmental neurotoxicity. Molecular neurotoxicology: environmental agents and transcription-transduction coupling 2004, 151-182. CRC press, Boca Roton, FL. N.H. Zawia (Ed.).
13. Lehmler H.J., Robertson L.W. Synthesis of hydroxylated PCB metabolites with the Suzuki-coupling. Chemosphere 2001, 45:1119-1127.
14. Lehmler H.-J., Parkin S., Robertson L.W. The three-dimensional structure of 3,3',5'-trichloro-4-methoxybiphenyl, a "coplanar" polychlorinated biphenyl (PCB) derivative. Chemosphere 2002, 46:485-488.
15. Letcher R.J., Klasson-Wehler E., Bergman A. Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. The handbook of environmental chemistry Vol. 3 Part K: new types of persistent halogenated compounds 2000, 315-359. Springer Verlag, Berlin Heidelberg. J. Paasivirta (Ed.).
16. Liu Y., Lien I.F.F., Ruttgaizer S., Dove P., Taylor S.D. Synthesis and protection of aryl sulfates using the 2,2,2-trichloroethyl moiety. Org Lett 2004, 6:209-212.
17. Liu Y., Apak T.I., Lehmler H.-J., Robertson L.W., Duffel M.W. Hydroxylated polychlorinated biphenyls are substrates and inhibitors of human hydroxysteroid sulfotransferase SULT2A1. Chem Res Toxicol 2006, 19:1420-1425.
18. McLean M.R., Bauer U., Amaro A.R., Robertson L.W. Identification of catechol and hydroquinone metabolites of 4-monochlorobiphenyl. Chem Res Toxicol 1996, 9:158-164.
19. Nishino T., Nagumo T. Anticoagulant and antithrombin activities of oversulfated fucans. Carbohydr Res 1992, 229:355-362.
20. Otwinowski Z., Minor W. Processing of X-ray diffraction data collected in oscillation mode. In: Carter Jr. CW, Sweet RM, editors. Methods in enzymology 1997, 307-326. Academic Press.
21. Park J.-S., Linderholm L., Charles M.J., Athanasiadou M., Petrik J., Kocan A., et al. Polychlorinated biphenyls and their hydroxylated metabolites (OH-PCBs) in pregnant women from Eastern Slovakia, Environ. Health Perspect 2007, 115:20-27.
22. Petitou M., van Boeckel C.A.A. A synthetic antithrombin III binding pentasaccharide is now a drug! What comes next?. Angew Chem Int Ed 2004, 43:3118-3133.
23. Pires L., Gorin P.A.J., Reicher F., Sierakowski M.R. An active heparinoid obtained by sulphation of a galactomannan extracted from the endosperm of Senna macranthera seeds. Carbohydr Polymers 2001, 46:165-169.
24. Ragan M.A. Phenol sulfate esters-ultraviolet, infrared, H-1 and C-13 nuclear magnetic-resonance spectroscopic investigation. Can J Chem 1978, 56:2681-2685.
25. Robertson L.W., Hansen L.G. Recent advances in the environmental toxicology and health effects of PCBs 2001, University Press of Kentucky, Lexington.
26. Sacco J.C., James M.O. Sulfonation of environmental chemicals and their metabolites in the polar bear (Ursus maritimus). Drug Metab Dispos 2005, 33:1341-1348.
27. Santos G.A.G., Murray A.P., Pujol C.A., Damonte E.B., Maier M.S. Synthesis and antiviral activity of sulfated and acetylated derivatives of 2',3'-dihydroxy-5'-cholestane. Steroids 2003, 68:125-132.
28. Schuur A.G., Brouwer A., Bergman, Coughtrie M.W.H., Visser T.J. Inhibition of thyroid hormone sulfation by hydroxylated metabolites of polychlorinated biphenyls. Chem-Biol Interact 1998, 109:293-297.
29. Schuur A.G., Legger F.F., van Meeteren M.E., Moonen M.J.H., van Leeuwen-Bol I., Bergman A., et al. In vitro inhibition of thyroid hormone sulfation by hydroxylated metabolites of halogenated aromatic hydrocarbons. Chem Res Toxicol 1998, 11:1075-1081.
30. Schuur A.G., van Leeuwen-Bol I., Jong W.M.C., Bergman A., Coughtrie M.W.H., Brouwer A., et al. In vitro inhibition of thyroid hormone sulfation by polychlorobiphenylols: isozyme specificity and inhibition kinetics. Toxicol Sci 1998, 45:188-194.
31. Sheldrick G.M. A short history of SHELX. Acta Cryst 2008, A64:112-122.
32. Silberhorn E.M., Glauert H.P., Robertson L.W. Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs. Crit Rev Toxicol 1990, 20:439-496.
33. Simpson L.S., Widlanski T.S. A comprehensive approach to the synthesis of sulfate esters. J Am Chem Soc 2006, 128:1605-1610.
34. Tampal N., Lehmler H.-J., Espandiari P., Malmberg T., Robertson L.W. Glucuronidation of hydroxylated polychlorinated biphenyls (PCBs). Chem Res Toxicol 2002, 15:1259-1266.
35. van den Hurk P., Kubiczak G.A., Lehmler H.J., James M.O. Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo[a]pyrene. Environ Health Perspect 2002, 110:343-348.
36. Vyas S.M., Parkin S., Lehmler H.-J. 2,2',3,4,4',5,5'-Heptachlorobiphenyl (PCB 180). Acta Cryst 2006, E62:o2905-o2906.
37. Vyas S.M., Parkin S., Lehmler H.-J. 2,5-Dichloro-4'-methoxybiphenyl. Acta Cryst 2006, E62:o4162-o4163.
38. Wang L.-Q., Lehmler H.-J., Robertson L.W., Falany C.N., James M.O. In vitro inhibition of human hepatic and cDNA-expressed sulfotransferase activity with 3-hydroxybenzo[a]pyrene by polychlorobiphenylols. Environ Health Perspect 2005, 113:680-687.
39. Wang L.-Q., Lehmler H.-J., Robertson L.W., James M.O. Polychlorobiphenylols are selective inhibitors of human phenol sulfotransferase 1A1 with 4-nitrophenol as a substrate. Chem Biol Interact 2006, 159:235-246.
40. Wilson A.J.C. International tables for crystallography. Vol C: mathematical, physical and chemical tables 1992, Kluwer Academic Publishers, Holland.