Oxidation of 4-chlorobiphenyl metabolites to electrophilic species by prostaglandin H synthase

Chemical Research in Toxicology

Volumn 22, Issue 1, 2009, Pages 64-71

  Wangpradit, Orarat ^a   Mariappan, S V Santhana ^b   Teesch, Lynn M ^a   Duffel, Michael W ^a   Norstrom, Karin ^a   Robertson, Larry W ^a   Luthe, Gregor ^a,c  

^a UNIVERSITY OF IOWA   (United States)

^b E11 SSH   (United States)

^c SAXION UNIVERSITY OF APPLIED SCIENCES   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROBIPHENYL; ACETYLCYSTEINE; BIPHENYL DERIVATIVE; CARBON; ELECTROPHILE; HYDROGEN; POLYCHLORINATED BIPHENYL; PROSTAGLANDIN H2; PROSTAGLANDIN SYNTHASE; PROTEIN; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DNA DAMAGE; HETERONUCLEAR NUCLEAR MAGNETIC RESONANCE; HUMAN; IN SITU HYBRIDIZATION; ISOLATION PROCEDURE; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITE; OXIDATION; OXIDATION REDUCTION REACTION; POLLUTANT; SUBSTITUTION REACTION;

ACETYLCYSTEINE; BIPHENYL COMPOUNDS; CHROMATOGRAPHY, LIQUID; DNA DAMAGE; ENVIRONMENTAL POLLUTANTS; MASS SPECTROMETRY; OXIDATION-REDUCTION; POLYCHLORINATED BIPHENYLS; PROSTAGLANDIN-ENDOPEROXIDE SYNTHASES; QUINONES;

EID: 61849120129     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx800300t     Document Type: Article

References (39)

1. Carson, R. (1962) Silent Spring, Houghton Mifflin, Boston.
2. Fiedler, H. (2001) Global and local disposition of PCBs. In Recent Advances in Environmental Toxicology and Health Effects (Robertson, L. W., and Hansen, L. G., Eds.) pp 11 - 15, University Press of Kentucky, Lexington, KY.
3. Ludewig, G.; Esch, H., and Robertson, L. W. (2007) Polyhalogenierte Bi- und Terphenyle. In Handbuch der Lebensmitteltoxikologie (Dunkel-berg, H.; Gabel, T., and Hartwig, A., Ed.) Chapter 20, pp 1031-1094, Wiley-VCH, Weinheim, Germany.
4. Vogel, C., Boerboom, A. M., Baechle, C., El-Bahay, C., Kahl, R., Degen, G. H., and Abel, J. (2000) Regulation of prostaglandin endoperoxide H synthase-2 induction by dioxin in rat hepatocytes: Possible c-Src-mediated pathway. Carcinogenesis 21, 2267-2274.
5. Smith, W. L., DeWitt, D. L., and Garavito, R. M. (2000) Cyclooxy-genases: Structural, cellular, and molecular biology. Annu. Rev. Biochem. 69, 145-182.
6. Kurumbail, R. G., Kiefer, J. R., and Marnett, L. J. (2001) Cyclooxy-genase enzymes: Catalysis and inhibition. Curr. Opin. Struct. Biol. 11, 752-760.
7. Malkowski, M. G., Ginell, S. L., Smith, W. L., and Garavito, R. M. (2000) The productive conformation of arachidonic acid bound to prostaglandin synthase. Science 289, 1933-1937.
8. Brant, K., and Caruso, R. L. (2005) Late-gestation rat myometrial cells express multiple isoforms of phospholipase A2 that mediate PCB 50-induced release of arachidonic acid with coincident prostaglandin production. Toxicol. Sci. 88, 222-230.
9. Bezdecny, S. A., Roth, R. A., and Ganey, P. E. (2005) Effects of 2,2′,4,4′-tetrachlorobiphenyl on granulocytic HL-60 cell function and expression of cyclooxygenase-2. Toxicol. Sci. 84, 328-334.
10. McLean, M. R., Bauer, U., Amaro, A. R., and Robertson, L. W. (1996) Identification of catechol and hydroquinone metabolites of 4-monochlo- robiphenyl. Chem. Res. Toxicol. 9, 158-164.
11. Espandiari, P., Glauert, H. P., Lehmler, H. J., Lee, E. Y., Srinivasan, C., and Robertson, L. W. (2004) Initiating activity of 4-chlorobiphenyl metabolites in the resistant hepatocyte model. Toxicol. Sci. 79, 41-46.
12. Prince, M. M., Ruder, A. M., Hein, M. J., Waters, M. A., Whelan, E. A., Nilsen, N., Ward, E. M., Schnorr, T. M., Laber, P. A., and Davis-King, K. E. (2006) Mortality and exposure response among 14,458 electrical capacitor manufacturing workers exposed to poly-chlorinated biphenyls (PCBs). Environ. Health Perspect. 114, 1508-1514.
13. Ritchie, J. M., Vial, S. L., Fuortes, L. J., Guo, H., Reedy, V. E., and Smith, E. M. (2003) Organochlorines and risk of prostate cancer. J. Occup. Environ. Med. 45, 692-702.
14. Ptak, A., Ludewig, G., Lehmler, H. J., Wojtowicz, A. K., Robertson, L. W., and Gregoraszczuk, E. L. (2005) Comparison of the actions of 4-chlorobiphenyl and its hydroxylated metabolites on estradiol secretion by ovarian follicles in primary cells in culture. Reprod. Toxicol. 20, 57-64.
15. Ptak, A., Ludewig, G., Kapiszewska, M., Magnowska, Z., Lehmler, H. J., Robertson, L. W., and Gregoraszczuk, E. L. (2006) Induction of cytochromes P450, caspase-3 and DNA damage by PCB3 and its hydroxylated metabolites in porcine ovary. Toxicol. Lett. 166, 200-211.
16. Lin, C. H., and Lin, P. H. (2006) Induction of ROS formation, poly(ADP-ribose) polymerase-1 activation, and cell death by PCB 126 and PCB153 in human T47D and MDA-MB-231 breast cancer cells. Chem.-Biol. Interact. 162, 181-194.
17. Oakley, G. G., Devanaboyina, U., Robertson, L. W., and Gupta, R. C. (1996) Oxidative DNA damage induced by activation of polychlori-nated biphenyls (PCBs): Implications for PCB-induced oxidative stress in breast cancer. Chem. Res. Toxicol. 9, 1285-1292.
18. Oakley, G. G., Robertson, L. W., and Gupta, R. C. (1996) Analysis of polychlorinated biphenyl-DNA adducts by 32P-postlabeling. Carcinogenesis 17, 109-114.
19. McLean, M. R., Robertson, L. W., and Gupta, R. C. (1996) Detection of PCB adducts by the 32P-postlabeling technique. Chem. Res. Toxicol. 9, 165-171.
20. Srinivasan, A., Lehmler, H. J., Robertson, L. W., and Ludewig, G. (2001) Production of DNA strand breaks in vitro and reactive oxygen species in vitro and in HL-60 cells by PCB metabolites. Toxicol. Sci. 60, 92-102.
21. Amaro, A. R., Oakley, G. G., Bauer, U., Spielmann, H. P., and Robertson, L. W. (1996) Metabolic activation of PCBs to quinones: reactivity toward nitrogen and sulfur nucleophiles and influence of superoxide dismutase. Chem. Res. Toxicol. 9, 623-629.
22. Moridani, M., Scobie, H., Salehi, P., and O'Brien, P. J. (2001) Catechin metabolism: Glutathione conjugate formation catalyzed by tyrosinase, peroxidase and cytochrome P450. Chem. Res. Toxicol. 14, 841-848.
23. Iverson, S. L., Shen, L., Anlar, N., and Bolton, J. L. (1996) Bioactivation of estrone and its catechol metabolites to quinoid-glutathione conjugates in rat liver microsomes. Chem. Res. Toxicol. 9, A92-A99.
24. McGirr, L. G., Subrahamanyam, V. V., Moore, G. A., and O'Brien, P. J. (1986) Peroxidase-catalyzed 3-(gluatathion-S-yl)-p,p'-biphenol formation. Chem.-Biol. Interact. 60, 85-99.
25. Josephy, P. D., and Iwaniw, D. C. (1985) Identification of the N-acetylcysteine conjugate of benzidine formed in the peroxidase activation system. Carcinogenesis 6, 155-158.
26. Pereg, D., Tampal, N., Espandiari, P., and Robertson, L. W. (2001) Distribution and macromolecular binding of benzo[a]pyrene and two polychlorinated biphenyl congeners in female mice. Chenu-Biol. Interact. 137, 243-258.
27. Bauer, U., Amaro, A. R., and Robertson, L. W. (1995) A new strategy for the synthesis of polychlorinated biphenyl metabolites. Chem. Res. Toxicol. 8, 92-95.
28. Van Weemen, B. K., and Schuurs, A. H. (1971) Immunoassay using antigen-enzyme conjugates. FEBS Lett. 15, 232-236.
29. Engvall, E., and Perlman, P. (1971) Enzyme-linked immunosorbent assay (ELISA). Quantitative assay of immunoglobulin G. Immu-nochemistry 8, 871-874.
30. Cayman Chemical (2002) EIA. EIA Workshop, Cayman Chemical, Ann Arbor, MI.
31. Gans, K. R., Galbraith, W., Roman, R. J., Haber, S. B., Kerr, J. S., Schmidt, W. K., Smith, C., Hewes, W. E., and Ackerman, N. R. (1990) Anti-inflammatory and safety profile of DuP 697, a novel orally effective prostaglandin synthesis inhibitor. J. Pharmacol. Exp. Ther. 254, 180-187.
32. Marnett, L. J., Johnson, J. T., and Bienkowski, M. J. (1979) Arachidonic acid-dependent metabolism of 7,8-dihydroxy-7,8-dihydro-benzo[a]pyrene by ram seminal vesicles. FEBS Lett. 106, 13-16.
33. Marnett, L. J., and Bienkowski, M. J. (1980) Hydroperoxide-dependent oxygenation of (ran.s-7,8-dihydroxy-7,8-dihydro benzo[a]pyrene by ram seminal vesicle microsomes. Source of the oxygen. Biochem. Biophys. Res. Commun. 96, 639-647.
34. Marnett, L. J., Rowlinson, S. W., Goodwin, D. C., Kalgutkar, A. S., and Lanzo, C. A. (1999) Arachidonic acid oxygenation by COX-1 and COX-2. Mechanisms of catalysis and inhibition. J. Biol. Chem. 274, 22903-22906.
35. Luthe, G.; Ariese, F., and Brinkman, U. A. Th. (2002) Monofluorinated polycyclic aromatic hydrocarbons: standards in environmental chemistry and biochemical applications. In Handbook of Environmental Chemistry: Organic Fluorine Compounds (Neilson, A. H., Ed.) pp 249-275, Springer Verlag, Berlin, Germany.
36. Luthe, G., Garcia-Boy, R., Jacobus, J., Smith, B., Rahaman, A., Robertson, L. W., and Ludewig, G. (2008) Xenobiotic geometry and media pH determine cytotoxicity through solubility. Chem. Res. Toxicol. 21, 1017-1027.
37. Gottlieb, H. E., Kotlyar, V., and Nudelman, A. (1997) NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 62, 7512-7515.
38. Gunther, H. (1995) NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry, 2nd ed., John Wiley & Sons, New York.
39. Tyszka, J. M., Fraser, S. E., and Jacobs, R. E. (2005) Magnetic resonance microscopy: recent advances and applications. Curr. Opin. Biotechnol. 16, 93-99.