Identification of human and rabbit cytochromes P450 1A2 as major isoforms involved in thiabendazole 5-hydroxylation

Fundamental and Clinical Pharmacology

Volumn 12, Issue 2, 1998, Pages 225-235

  Coulet, M ^a   Dacasto, M ^b   Eeckhoutte, C ^a   Larrieu, G ^a   Sutra, J F ^a   Alvinerie, M ^a   Mace K ^c   Pfeifer, A M A ^c   Galtier, P ^a  

^a CEMAGREF   (France)

^b UNIVERSITY OF TURIN   (Italy)

^c NESTLÉ RESEARCH CENTER   (Switzerland)

Author keywords

Cytochromes P450; Drug drug interactions; Hepatocytes; Human cell lines; Metabolism; Thiabendazole

Indexed keywords

5 HYDROXYTHIABENDAZOLE; ANTHELMINTIC AGENT; BETA NAPHTHOFLAVONE; CLOFIBRATE; CYTOCHROME P450 ISOENZYME; DRUG METABOLITE; ETHOXYRESORUFIN; ETHOXYRESORUFIN DEETHYLASE; PHENOBARBITAL; RIFAMPICIN; TIABENDAZOLE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL LINE; CONTROLLED STUDY; DRUG HYDROXYLATION; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INDUCTION; EPITHELIUM CELL; HUMAN; HUMAN CELL; IN VITRO STUDY; LIVER CELL CULTURE; LIVER METABOLISM; MALE; NONHUMAN; PRIORITY JOURNAL; RABBIT;

EID: 0031968527     PISSN: 07673981     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1472-8206.1998.tb00946.x     Document Type: Article

References (44)

1. Aix L, Rey-Grobellet X, Larrieu G, Lesca P, Galtier P. Thiabendazole is an inducer of cytochrome P450 1A1 in cultured rabbit hepatocytes. Biochem Biophys Res Commun 1994 ; 202 : 1483-9
2. Alvinerie M, Sutra JF, Galtier P. Dosage par CHLP de deux médicaments à caractère basique (trimethoprim, thiabendazole) à l'aide d'une phase greffée avec désactivation des silanols libres. Analusis 1991 ; 19 : 224-8
3. Barcelo S, Macé K, Pfeifer AMA, Chipman JK. Production of DNA strand breaks by N-nitrosodimethylamine (NDMA) and 2-amino-3-methylimidazo[4,5-f]quinoline (IQ) in THLE cells expressing human CYP isoenzymes and inhibition by sulforaphane. Mut Res 1997 ; In press
4. Bauer LA, Raisys VA, Watts MT, Ballinger J. The pharmacokinetics of thiabendazole and its metabolites in an anephric patient undergoing hemodialysis and hemoperfusion. J Clin Pharmacol 1982 ; 22 : 276-80
5. Bergmeyer HU, Bernt E, Hess B. Lactic deshydrogenase. In: Bergmeyer HU, ed. Methods of Enzymatic Analysis. New York: Academic Press; 1963. p 736-41
6. Burke MD, Thompson RJ, Weaver CR, Wolf CR, Mayer RT. Cytochrome P450 specificities of alkoxyresorufin O-dealkylation in human and rat liver. Biochem Pharmacol 1994 ; 48 : 923-36
7. Cochin J, Axelrod J. Biochemical and pharmacological changes in the rat following chronic administration of morphine, nalorphine, and normorphine. J Pharmacol Exp Ther 1959 ; 125 : 105-15
8. Daujat M, Pichard L, Dalet C, Larroque, C, Bonfils C, Pompon D et al. Expression of five forms of microsomal cytochrome P450 in primary cultures of rabbit hepatocytes treated with various classes of inducers. Biochem Pharmacol 1987 ; 36 : 3597-606
9. Darbyshire JF, Iyer KR, Grogan J, Korzekwa KR, Trager WF. Selectively deuterated warfarin: Substrate probe for the mechanism of aromatic hydroxylation catalysed by cytochrome P450. Drug Metab Dispos 1996 ; 24 : 1038-945
10. Davidson RN, Weir WR, Kaye GL, McIntyre N. Intrahepatic cholestasis after thiabendazole. Trans R Soc Trop Med Hyg 1988 ; 82 : 620
11. Fujitani T, Yoneyama M, Ogata A, Ueta T, Mori K, Ichikawa H. New metabolites of thiabendazole and the metabolism of thiabendazole by mouse embryo in vivo and in vitro. Food Chem Toxicol 1991 ; 29 : 265-74
12. Gardiner JA, Kirkland JJ, Klopping HL, Sherman H. Fate of benomyl in animals. J Agric Food Chem 1974 ; 22 : 419-27
13. Henri P, Mosquet B, Hurault de Ligny B, Lacotte J, Cardinau E, Moulin M, Ryckelinck JP. Imputation d'une hypocoagulabilité à l'interaction thiabendazole-acénocoumarol. Therapie 1993 ; 48 : 483-501
14. Ioannides C, Parke DV. The cytochrome P4501 gene family of microsomal hemoproteins and their role in the metabolic activation of chemicals. Drug Metab Rev 1990; 22 : 1-85
15. Ioannides C, Parke DV. Induction of cytochrome P4501 as an indicator of potential chemical carcinogenesis. Drug Metab Rev 1993 ; 25 : 485-501
16. Kaminski LS, Demorais SMF, Faletto MB, Dunbar DA, Goldstein JA. Correlation of human cytochrome P450 substrate specificities with primary structure: Warfarine as a probe. Mol Pharmacol 1993 ; 43 : 234-9
17. Kocarek TA, Schuetz EG, Strom SC, Fisher RA, Guzelian PS. Comparative analysis of cytochrome P450 3A induced in primary cultures of rat, rabbit and human hepatocytes. Drug Metab Dispos 1995 ; 23 : 415-21
18. Laemmli UK. Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 1970 ; 227 : 680-5
19. Lake BJ. Preparation and characterisation of microsomal fraction for studies on xenobiotic metabolism. In: Snell K and Mullock B, eds. Biochemical Toxicology. Oxford: ICR; 1987. p 183-215
20. Lechner JF, La Veck MA. A serum-free method for culturing normal human bronchial epithelial cells at clonal density. J Tissue Culture Methods 1985 ; 9 : 43-8
21. Lew G, Murray WE, Lane JR, Haeger E. Theophylline-thiabendazole drug interaction. Clin Pharm 1989 ; 8 : 225-7
22. Macé K, Gonzalez FJ, Mcconell IR, Garner RC, Avanti O, Harris CC, Pfeifer AMA. Activation of promutagens in a human bronchial epithelial cell line stably expressing human cytochrome P450 1A2. Mol Carcinog 1994 ; 11 : 65-73
23. Macé K, Aguilar F, Wang JS, Vautravers P, Gomez-Lechon M, Gonzalez M et al. Aflatoxin B1-induced DNA adduct formation and p53 mutations in CYP450-expressing human liver cell lines. Carcinogenesis 1997; 18: 1291-7
24. Mizutani T, Ito K, Nomura H, Nakanishi K. Nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine. Food Chem Toxicol 1990 ; 28 : 169-77
25. Omura T, Sato RA. A new cytochrome in liver microsomes. J Biol Chem 1962 ; 237 : 1375-6
26. Pfeifer AMA, Macé K, Tromvoukis Y, Lipsky MM. Highly efficient establisment of immortalized cells from adult human liver. Meth Cell Science 1995 ; 17 : 83-9
27. Rendic S, Di Carlo FJ. Human cytochrome P450 enzymes: a status report summarizing their reactions, substrates, inducers, and inhibitors. Drug Metab Rev 1997 ; 29 : 413-580
28. Rex D, Lumeng L, Eble J, Rex L. Intrahepatic cholestasis and sicca complex after thiabendazole. Gastroenterology 1983 ; 85 : 718-21
29. Rey-Grobellet X, Eeckhoutte C, Sutra JF, Alvinerie M, Galtier P. Major involvement of rabbit liver cytochrome P450 IA in thiabendazole 5-hydroxylation. Xenobiotica 1996 ; 26(7) : 765-78
30. Roberts EA, Xie ZW, Yang S, Lipa J. Inducibility of enzyme activities associated with the cytochrome P450 IA family, ethoxyresorufin O-deethylase, and methoxyresorufin O-demethylase in human hepatocyte lines derived from normal liver tissue. Drug Metab Dispos 1993 ; 21 : 56-61
31. Roy MA, Warren Nugent MDF, Thomas Aretz MDH. Micronodular cirrhosis after thiabendazole. Dig Dis Sci 1989 ; 34 : 938-41
32. Schumaker JD, Bank JD, Lensmeyer GL, Graig WA. Thiaben-dazole treatment of severe strongyloidiosis in a hemodialized patient. Ann Int Med 1978 ; 89 : 644-5
33. Smith PK, Krohn RI, Hermason GT, Mallia AK, Gartner FH, Provenzo MD et al. Measurement of protein using bicinchoninic acid. Anal Biochem 1985 ; 150 : 76-85
34. Stone OJ, Mullins JF, Willis CJ. Comparison of thiabendazole and 5-hydroxy-thiabendazole. J Invest Dermatol 1965 ; 45 : 132-3
35. Tarbit MH, Bayliss MK, Herriott D, Hood SR, Hutson JL, Park GR, Serabjit-Singh CJ. Applications of molecular biology and in vitro technology to drug metabolism studies: an industrial perspective. Biochem Soc Trans 1993 ; 21 : 1018-23
36. Tocco DJ. The metabolic fate of thiabendazole in sheep. J Med Chem 1964; 7 : 399-405
37. Tocco DJ, Egerton JR, Bowers W, Christensen VW, Rosenblum C. Absorption, metabolism and elimination of thiabendazole in farm animals and a method for its estimation in biological materials. J Pharmacol Exp Ther 1965 ; 149 : 263-71
38. Tocco DJ, Rosenblum C, Martin CM, Robinson HJ. Absorption, metabolism, and excretion of thiabendazole in man and laboratory animals. Toxicol Appl Pharmacol 1966 ; 9 : 31-9
39. Towbin H, Staehelin T, Gordon J. Electrophoretic transfer of protein from polyacrylamide gels to nitrocellulose sheets: procedure and some application. Proc Natl Acad Sci USA 1979 ; 76 :4350-4
40. Tsuchiya T, Tanaka A, Fukukoa M, Sato M, Yamaha T. Metabolism of thiabendazole and teratogenic potential of its metabolites in pregnant mice. Chem Pharm Bull 1987 ; 35 : 2985-93
41. Van der Hoeven T, Coon MJ. Preparation and properties of partially purified cytochrome P450 and reduced nicotinamide adenine dinucleotide phosphate cytochrome P450 reductase from rabbit liver microsomes. J Biol Chem 1974 ; 249 : 6202-10
42. Wrighton A, Campanile C, Thomas PE, Maines SL, Watkins PB, Parker G et al. Identification of a human liver cytochrome P450 homologous to the major isosafrole-inducible cytochrome P450 in the rat. Mol Pharamacol 1986 ; 29 : 405-10
43. Yoneyama M, Ichikawa H. Irreversible in vivo and in vitro binding of thiabendazole to tissue proteins of pregnant mice. Food Chem Toxicol 1986 ; 24 : 1283-6
44. Zang ZI, Fasco MJ, Guengerich FP, Kaminsky LS. Warfarin metabolism by human P4501A1 and 1A2-noninvasive probe. ISSX Proceedings, 4th International ISSX Meeting; 1995 Aug 27-Sept 1; Seattle, WA. p 81