In vitro metabolism of polychlorinated biphenyls and cytochrome P450 monooxygenase activities in dietary-exposed Greenland sledge dogs

Comparative Biochemistry and Physiology - C Toxicology and Pharmacology

Volumn 150, Issue 1, 2009, Pages 91-100

  Verreault, Jonathan ^a,b   Letcher, Robert J ^a,b   Sonne, Christian ^c   Dietz, Rune ^c  

^a ENVIRONMENT CANADA   (Canada)

^b CARLETON UNIVERSITY   (Canada)

^c NATIONAL ENVIRONMENTAL RESEARCH INSTITUTE   (Denmark)

Author keywords

Biotransformation; Cytochrome P450; Dogs; Hepatic microsomes; Hydroxylated metabolites; In vitro; Polychlorinated biphenyls; Testosterone hydroxylase

Indexed keywords

ANDROSTENEDIONE; CARBON; CYTOCHROME P450; CYTOCHROME P450 2B; CYTOCHROME P450 2C; CYTOCHROME P450 3A; CYTOCHROME P450 ISOENZYME; ENZYME; ETHOXYRESORUFIN DEETHYLASE; ORGANOHALOGEN DERIVATIVE; POLYCHLORINATED BIPHENYL; TESTOSTERONE HYDROXYLASE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BINDING SITE; BIOTRANSFORMATION; CANIS FAMILIARIS; CATALYSIS; CONTROLLED STUDY; CORRELATION ANALYSIS; DIET; DOG; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME SPECIFICITY; FEMALE; IN VITRO STUDY; LIVER MICROSOME; METABOLISM; NONHUMAN; PRIORITY JOURNAL;

BALAENOPTERA ACUTOROSTRATA; CANIS FAMILIARIS;

EID: 67349136838     PISSN: 15320456     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.cbpc.2009.03.004     Document Type: Article

References (51)

1. Ariyoshi N., Koga N., Oguri K., and Yoshimura H. Metabolism of 2,4,5,2',4',5'-hexachlorobiphenyl with liver microsomes of phenobarbital-treated dog; the possible formation of PCB 2,3-arene oxide intermediate. Xenobiotica 22 (1992) 1275-1290
2. Ariyoshi N., Koga N., Yoshimura H., and Oguri K. Metabolism of 2,4,5,2',4',5'-hexachlorobiphenyl (PCB153) in guinea pig. Xenobiotica 27 (1997) 973-983
3. Borlakoglu J.T., and Wilkins J.P. Metabolism of di-, tri-, tetra-, penta- and hexachlorobiphenyls by hepatic microsomes isolated from control animals and animals treated with Aroclor 1254, a commercial mixture of polychlorinated biphenyls (PCBs). Comp. Biochem. Physiol., C 105 (1993) 95-106
4. Born S.L., Fraser D.J., Harlow G.R., and Halpert J.R. Escherichia coli expression and substrate specificities of canine cytochrome P450 3A12 and rabbit cytochrome P450 3A6. J. Pharmacol. Exp. Ther. 278 (1996) 957-963
5. Ciaccio P.J., and Halpert J.R. Characterization of a phenobarbital-inducible dog liver cytochrome P450 structurally related to rat and human enzymes of the P450IIIA (steroid-inducible) gene subfamily. Arch. Biochem. Biophys. 271 (1989) 284-299
6. Court M.H., Hay-Kraus B.L., Hill D.W., Kind A.J., and Greenblatt D.J. Propofol hydroxylation by dog liver microsomes: assay development and dog breed differences. Drug Metab. Dispos. 27 (1999) 1293-1299
7. de Wit C.A., Fisk A.T., Hobbs K.E., Muir D.C.G., Gabrielsen G.W., Kallenborn R., Krahn M.M., Norstrom R.J., and Skaare J.U. AMAP assessment 2002: persistent organic pollutants in the Arctic. Arctic Monitoring and Assessment Programme (AMAP), Oslo, Norway (2004)
8. Duignan D.B., Sipes I.G., Leonard T.B., and Halpert J.R. Purification and characterization of the dog hepatic cytochrome P-450 isozyme responsible for the metabolism of 2,2',4,4',5,5'-hexachlorobiphenyl. Arch. Biochem. Biophys. 255 (1987) 290-303
9. Duignan D.B., Sipes I.G., Ciaccio P.J., and Halpert J.R. The metabolism of xenobiotics and endogenous compounds by the constitutive dog liver cytochrome P450 PBD-2. Arch. Biochem. Biophys. 267 (1988) 294-304
10. Fisk A.T., de Wit C.A., Wayland M., Kuzyk Z.Z., Burgess N., Letcher R.J., Braune B.M., Norstrom R.J., Polischuk Blum S., Sandau C., Lie E., Larsen H.J.S., Skaare J.U., and Muir D.C.G. An assessment of the toxicological significance of anthropogenic contaminants in Canadian arctic wildlife. Sci. Total Environ. 351/352 (2005) 57-93
11. Fraser D.J., Feyereisen R., Harlow G.R., and Halpert J.R. Isolation, heterologous expression and functional characterization of a novel cytochrome P450 3A enzyme from a canine liver cDNA library. J. Pharmacol. Exp. Ther. 283 (1997) 1425-1432
12. Gebbink W.A., Sonne C., Dietz R., Kirkegaard M., Riget F.F., Born E.W., Muir D.C., and Letcher R.J. Tissue-specific congener composition of organohalogen and metabolite contaminants in East Greenland polar bears (Ursus maritimus). Environ. Pollut. 152 (2008) 621-629
13. Graham R.A., Downey A., Mudra D., Krueger L., Carroll K., Chengelis C., Madan A., and Parkinson A. In vivo and in vitro induction of cytochrome P450 enzymes in beagle dogs. Drug Metab. Dispos. 30 (2002) 1206-1213
14. Graves P.E., Elhag G.A., Ciaccio P.J., Bourque D.P., and Halpert J.R. cDNA and deduced amino acid sequences of a dog hepatic cytochrome P450IIB responsible for the metabolism of 2,2',4,4',5,5'-hexachlorobiphenyl. Arch. Biochem. Biophys. 281 (1990) 106-115
15. Hay Kraus B.L., Greenblatt D.J., Venkatakrishnan K., and Court M.H. Evidence for propofol hydroxylation by cytochrome P4502B11 in canine liver microsomes: breed and gender differences. Xenobiotica 30 (2000) 575-588
16. Hobbs K.E., Muir D.C.G., Born E.W., Dietz R., Haug T., Metcalfe T., Metcalfe C., and Øien N. Levels and patterns of persistent organochlorines in minke whale (Balaenoptera acutorostrata) from the North Atlantic and European Arctic. Environ. Pollut. 121 (2003) 239-252
17. Ishida C., Koga N., Hanioka N., Saeki H.K., and Yoshimura H. Metabolism in vitro of 3,4,3',4'- and 2,5,2',5'-tetrachlorobiphenyl by rat liver microsomes and highly purified cytochrome P-450. J. Pharmacobiodyn. 14 (1991) 276-284
18. Kamimura H. Genetic polymorphism of cytochrome P450s in beagles: possible influence of CYP1A2 deficiency on toxicological evaluations. Arch. Toxicol. 80 (2006) 732-738
19. Kawano M., Hasegawa J., Enomoto T., Onishi H., Nishio Y., Matsuda M., and Wakimoto T. Hydroxylated polychlorinated biphenyls (OH-PCBs): recent advances in wildlife contamination study. Environ. Sci. 12 (2005) 315-324
20. Kirkegaard M., Sonne C., Leifsson P.S., Dietz R., Born E.W., Muir D.C.G., and Letcher R.J. Histology of selected immunological organs in polar bear (Ursus maritimus) from East Greenland in relation to concentrations of organohalogen contaminants. Sci. Total Environ. 341 (2005) 119-132
21. Kleivane L., and Skaare J.U. Organochlorine contaminants in northeast Atlantic minke whales (Balaenoptera acutorostrata). Environ. Pollut. 101 (1998) 231-239
22. Koga N., Kikuichi-Nishimura N., Hara T., Harada N., Ishii Y., Yamada H., Oguri K., and Yoshimura H. Purification and characterization of a newly identified isoform of cytochrome P450 responsible for 3-hydroxylation of 2,5,2',5'-tetrachlorobiphenyl in hamster liver. Arch. Biochem. Biophys. 317 (1995) 464-470
23. Korytko P.J., Casey A.C., Bush B., and Quimby F.W. Induction of hepatic cytochromes P450 in dogs exposed to a chronic low dose of polychlorinated biphenyls. Toxicol. Sci. 47 (1999) 52-61
24. Kuiper R.V., Bergman A., Vos J.G., and van den Berg M. Some polybrominated diphenyl ether (PBDE) flame retardants with wide environmental distribution inhibit TCDD-induced EROD activity in primary cultured carp (Cyprinus carpio) hepatocytes. Aquat. Toxicol. 68 (2004) 129-139
25. Letcher R.J., Klasson-Wehler E., and Bergman Å. Methyl sulfone and hydroxylated metabolites of polychlorinated biphenyls. In: Paasivita J. (Ed). The Handbook of Environmental Chemistry - New Types of Persistent Halogenated Compounds. Part K vol. 3 (2000), Springer-Verlag, Heidelberg, Germany 315-359
26. Lewis D.F., Ioannides C., and Parke D.V. Molecular dimensions of the substrate binding site of cytochrome P-448. Biochem. Pharmacol. 35 (1986) 2179-2185
27. Liu Y.T., Hao H.P., Liu C.X., Wang G.J., and Xie H.G. Drugs as CYP3A probes, inducers and inhibitors. Drug Metab. Rev. 39 (2007) 699-721
28. Muir D.C.G., Backus S., Derocher A.E., Dietz R., Evans T.J., Gabrielsen G.W., Nagy J., Norstrom R.J., Sonne C., Stirling I., Taylor M.K., and Letcher R.J. Brominated Flame Retardants in Polar Bears (Ursus maritimus) from Alaska, the Canadian Arctic, East Greenland, and Svalbard. Environ. Sci. Technol. 40 (2006) 449-455
29. Nishibe Y., Wakabayashi M., Harauchi T., and Ohno K. Characterization of cytochrome P450 (CYP3A12) induction by rifampicin in dog liver. Xenobiotica 28 (1998) 549-557
30. Ohmori S., Taniguchi T., Rikihisa T., Kanakubo Y., and Kitada M. Species differences of testosterone 16-hydroxylases in liver microsomes of guinea pig, rat and dog. Xenobiotica 23 (1993) 419-426
31. Ohta C., Haraguchi K., Kato Y., and Koga N. In vitro metabolism of 2,2',3,4',5,5',6-heptachlorobiphenyl (CB187) by liver microsomes from rats, hamsters and guinea pigs. Xenobiotica 35 (2005) 319-330
32. Ryan D.E., and Levin W. Purification and characterization of hepatic microsomal cytochrome P-450. Pharmacol. Ther. 45 (1990) 153-239
33. Shou M., Norcross R., Sandig G., Lu P., Li Y., Lin Y., Mei Q., Rodrigues A.D., and Rushmore T.H. Substrate specificity and kinetic properties of seven heterologously expressed dog cytochromes p450. Drug Metab. Dispos. 31 (2003) 1161-1169
34. Sipes I.G., Slocumb M.L., Perry D.F., and Carter D.E. 2,4,5,2',4',5'-Hexachlorobiphenyl: distribution, metabolism, and excretion in the dog and the monkey. Toxicol. Appl. Pharmacol. 65 (1982) 264-272
35. Smithwick M., Muir D.C.G., Mabury S.A., Solomon K., Martin J.W., Sonne C., Born E.W., Dietz R., Derocher A.E., Evans T., Gabrielsen G.W., Nagy J.I., Stirling I., and Taylor M.K. A circumpolar study of perfluoroalkyl contaminants in polar bear hepatic tissue (Ursus maritimus). Environ. Sci. Technol. 39 (2005) 5517-5523
36. Sonne C., Dietz R., Leifsson P.S., Born E.W., Letcher R.J., Kirkegaard M., Muir D.C., Riget F.F., and Hyldstrup L. Do organohalogen contaminants contribute to histopathology in liver from East Greenland polar bears (Ursus maritimus)?. Environ. Health. Perspect. 113 (2005) 1569-1574
37. Sonne C., Dietz R., Larsen H.J., Loft K.E., Kirkegaard M., Letcher R.J., Shahmiri S., and Moller P. Impairment of cellular immunity in west Greenland sledge dogs (Canis familiaris) dietary exposed to polluted minke whale (Balaenoptera acutorostrata) blubber. Environ. Sci. Technol. 40 (2006) 2056-2062
38. Sonne C., Dietz R., Leifsson P.S., Born E.W., Kirkegaard M., Letcher R.J., Muir D.C., Riget F.F., and Hyldstrup L. Are organohalogen contaminants a cofactor in the development of renal lesions in East Greenland polar bears (Ursus maritimus)?. Environ. Toxicol. Chem. 25 (2006) 1551-1557
39. Sonne C., Leifsson P.S., Dietz R., Born E.W., Letcher R.J., Hyldstrup L., Riget F.F., Kirkegaard M., and Muir D.C. Xenoendocrine pollutants may reduce size of sexual organs in East Greenland polar bears (Ursus maritimus). Environ. Sci. Technol. 40 (2006) 5668-5674
40. Sonne C., Leifsson P.S., Dietz R., Kirkegaard M., Møller P., Jensen A.J., Letcher R.J., and Shahmiri S. Renal lesions in Greenland sledge dogs (Canis familiaris) exposed to a natural dietary cocktail of persistent organic pollutants. Toxicol. Environ. Chem. 89 (2007) 563-576
41. Sonne C., Fonfara S., Dietz R., Kirkegaard M., Letcher R.J., Shahmiri S., Andersen S., and Moller P. Multiple cytokine and acute-phase protein gene transcription in West Greenland sledge dogs (Canis familiaris) dietary exposed to organic environmental pollutants. Arch. Environ. Contam. Toxicol. 53 (2007) 110-118
42. Sonne C., Dietz R., Kirkegaard M., Letcher R.J., Shahmiri S., Andersen S., Moller P., Olsen A.K., and Jensen A.L. Effects of organohalogen pollutants on haematological and urine clinical-chemical parameters in Greenland sledge dogs (Canis familiaris). Ecotoxicol. Environ. Saf. 69 (2008) 381-390
43. Sonne C., Leifsson P.S., Dietz R., Kirkegaard M., Møller P., Jensen A.L., and Letcher R.J. Greenland sledge dogs (Canis familiaris) develop liver lesions when exposed to a chronic and dietary low dose of an environmental organohalogen cocktail. Environ. Res. 106 (2008) 72-80
44. Sonne C., Bossi R., Dietz R., Leifsson P.S., Riget F.F., and Born E.W. Potential correlation between perfluorinated acids and liver morphology in East Greenland polar bears (Ursus maritimus). Toxicol. Environ. Chem. 90 (2008) 275-283
45. Sonne C., Rigét F.F., Jensen J.E.B., Hyldstrup L., Teilmann J., Dietz R., Kirkegaard M., Andersen S., Letcher R.J., and Jakobsen J. Does the nutrition profile of vitamins, fatty acids and microelements counteract the negative impact from organohalogen pollutants on bone mineral density in Greenland sledge dogs (Canis familiaris)?. Environ. Int. 34 (2008) 811-820
46. Uchida T., Komori M., Kitada M., and Kamataki T. Isolation of cDNAs coding for three different forms of liver microsomal cytochrome P-450 from polychlorinated biphenyl-treated beagle dogs. Mol. Pharmacol. 38 (1990) 644-651
47. Verreault J., Muir D.C.G., Norstrom R.J., Stirling I., Fisk A.T., Gabrielsen G.W., Derocher A.E., Evans T.J., Dietz R., Sonne C., Sandala G.M., Gebbink W.A., Riget F.F., Born E.W., Taylor M.K., Nagy J., and Letcher R.J. Chlorinated hydrocarbon contaminants and metabolites in polar bears (Ursus maritimus) from Alaska, Canada, East Greenland, and Svalbard: 1996-2002. Sci. Total Environ. 351/352 (2005) 369-390
48. Verreault J., Dietz R., Sonne C., Gebbink W.A., Shahmiri S., and Letcher R.J. Comparative fate of organohalogen contaminants in two top carnivores in Greenland: captive sledge dogs and wild polar bears. Comp. Biochem. Physiol., Part C Toxicol. Pharmacol. 147 (2008) 306-315
49. Verreault J., Maisonneuve F., Dietz R., Sonne C., and Letcher R.J. Comparative hepatic activity of xenobiotic-metabolizing enzymes and concentrations of organohalogens and their hydroxylated analogues in captive Greenland sledge dogs (Canis familiaris). Environ. Toxicol. Chem. 28 (2009) 162-172
50. Verreault J., Letcher R.J., Sonne C., and Dietz R. Dietary, age and trans-generational effects on the fate of organohalogen contaminants in captive sledge dogs in Greenland. Environ. Int. 35 (2009) 56-62
51. Williams T.M., Kind A.J., and Hill D.W. Drug metabolism: in vitro biotransformation of anabolic steroids in canines. J. Vet. Pharmacol. Ther. 23 (2000) 57-66