Effects of the antifungal imidazole ketoconazole on CYP1A and CYP3A in rainbow trout and killifish

Environmental Toxicology and Chemistry

Volumn 23, Issue 5, 2004, Pages 1326-1334

  Hegelund, Tove ^a   Ottosson, Karin ^a   Rådinger, Madeleine ^a   Tomberg, Peter ^a   Celander, Malin C ^a  

^a UNIVERSITY OF GOTHENBURG   (Sweden)

Author keywords

Cytochrome P450; Fish; Fungicides; Inhibition; Ketoconazole

Indexed keywords

CATALYST ACTIVITY; DNA; ENZYME INHIBITION; ENZYME KINETICS; METABOLISM;

BIOACCUMULATION; KILLFISH;

FUNGICIDES;

ANTIFUNGAL AGENT; BENZYL DERIVATIVE; BENZYLOXY 4 (TRIFLUOROMETHYL)COUMARIN O DEBENZYLOXYLASE; COUMARIN DERIVATIVE; CYTOCHROME P450; CYTOCHROME P450 1A; CYTOCHROME P450 3A; CYTOCHROME P450 INHIBITOR; ETHOXYRESORUFIN DEETHYLASE; FUNGICIDE; IMIDAZOLE; KETOCONAZOLE; MESSENGER RNA; OXIDOREDUCTASE; PROTEIN; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

DOSE-RESPONSE RELATIONSHIP; ECOTOXICOLOGY; FISH; INHIBITION; POLLUTION EXPOSURE; TOXICITY;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL TISSUE; CONFERENCE PAPER; CONTROLLED STUDY; CYPRINODONTIFORMES; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME INDUCTION; FEMALE; IN VITRO STUDY; MALE; MARINE ENVIRONMENT; NONHUMAN; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAINBOW TROUT;

ANIMALS; ANTIFUNGAL AGENTS; ARYL HYDROCARBON HYDROXYLASES; CYTOCHROME P-450 CYP1A1; CYTOCHROME P-450 CYP3A; DOSE-RESPONSE RELATIONSHIP, DRUG; ENZYME ACTIVATION; ENZYME INHIBITORS; FUNDULIDAE; HEPATOCYTES; INTESTINES; KETOCONAZOLE; LIVER; ONCORHYNCHUS MYKISS; OXIDOREDUCTASES, N-DEMETHYLATING; RNA, MESSENGER;

ANIMALIA; CYPRINODONTIFORMES; FUNDULUS HETEROCLITUS; ONCORHYNCHUS MYKISS; SALMONIDAE; STAPHYLOCOCCUS PHAGE 3A;

EID: 2442517393     PISSN: 07307268     EISSN: None     Source Type: Journal    
DOI: 10.1897/03-155     Document Type: Conference Paper

References (40)

1. Vanden Bossche H, Koymans L, Moereels H. 1995. P450 inhibitors of use in medical treatment: Focus on mechanisms of action. Pharmacol Ther 67:79-100.
2. Kan PB, Hirst MA, Feldman D. 1985. Inhibition of steroidogenic cytochrome P450 enzymes in rat testis by ketoconazole and related imidazole anti-fungal drugs. J Steroid Biochem 23:1023-1029.
3. Cummings AM, Hedge JL, Laskey J. 1997. Ketoconazole impairs early pregnancy and the decidual cell response via alterations in ovarian function. Fundam Appl Toxicol 40:238-246.
4. Venkatakrishnan K, von Moltke LL, Greenblatt DJ. 2000. Effects of the antifungal agents on oxidative drug metabolism. Clin Pharmacokinet 38:111-180.
5. Rodrigues AD, Waddell PR, Ah-Sing E, Morris BA, Wolf CR, Ioannides C. 1988. Induction of the rat hepatic microsomal mixed-function oxidases by 3 imidazole-containing antifungal agents: Selectivity for the cytochrome P450IIB and P450IIIA families of cytochrome P450. Toxicology 50:283-301.
6. Hostetler KA, Wrighton SA, Molowa DT, Thomas PE, Lewin W, Guzelian PS. 1989. Coinduction of multiple hepatic cytochrome P450 proteins and their mRNAs in rats treated with imidazole antimycotic agents. Mol Pharmacol 35:279-285.
7. Ronis MJJ, Ingelman-Sundberg M, Badger TM. 1994. Induction, suppression, and inhibition of multiple hepatic cytochrome P450 isoenzymes in the male rat and bobwhite quail (Colinus virginianus) by ergosterol biosynthesis inhibiting fungicides (EBIFs). Biochem Pharmacol 48:1953-1965.
8. Ronis MJJ, Badger TM. 1995. Toxic interactions between fungicides that inhibit ergosterol biosynthesis and phosphorothioate insecticides in the male rat and bobwhite quail (Colinus virginianus). Toxicol Appl Pharmacol 130:221-228.
9. Ronis MJJ, Celander M, Badger TM. 1998. Cytochrome P450 enzymes in the kidney of the bobwhite quail (Colinus virginianus): Induction and inhibition by ergosterol biosynthesis inhibiting fungicides. Comp Biochem Physiol 121:221-229.
10. Maurel P. 1996. The CYP3 family. In Ioannides C, ed, Cytochromes P450 Metabolic and Toxicological Aspects. CRC, Boca Raton, FL, USA, pp 241-270.
11. Parkinson A. 1996. Biotransformation of xenobiotics. In Klaassen CD, ed, Casarett & Doull's Toxicology: The Basic Science of Poisons, 5th ed. McGraw-Hill, New York, NY, USA, pp 113-186.
12. Guengerich FP. 1999. Cytochrome P450 3A4: Regulation and role in drug metabolism. Annu Rev Pharmacol Toxicol 39:1-17.
13. Maurice M, Pichard L, Daujat M, Fabre I, Joyeux H, Domergue J, Maurel P. 1992. Effects of imidazole derivatives on cytochromes P450 from human hepatocytes in primary culture. FASEB J 6:752-758.
14. Thummel KE, Wilkinson GR. 1998. In vitro and in vivo drug interactions involving human CYP3A. Annu Rev Pharmacol Toxicol 38:389-430.
15. Boxenbaum H. 1999. Cytochrome P450 3A4 in vivo ketoconazole competitive inhibition: Determination of Ki and dangers associated with high clearance drugs in general. Journal of Pharmacology and Pharmaceutical Sciences 2:45-52.
16. Miranda CL, Henderson MC, Buhler DR. 1998. Evaluation of chemicals as inhibitors of trout cytochrome P450s. Toxicol Appl Pharmacol 148:237-244.
17. Paine MF, Schmiedlin-Ren P, Watkins P. 1999. Cytochrome P-450 1A1 expression in human small bowel: Interindividual variation and inhibition of ketoconazole. Drug Metab Dispos 27:360-364.
18. Levine SL, Czosnyka H, Oris JT. 1997. Effect of the fungicide clotrimazole on bioconcentration of benzo[a]pyrene in gizzard shad (Dorosoma cepedianum): In vivo and in vitro inhibition of cytochrome P4501A activity. Environ Toxicol Chem 16:306-311.
19. Sturm A, Cravedi JP, Perdu E, Baradat M, Segner H. 2001. Effects of prochloraz and nonylphenol diethoxylate on hepatic biotransformation enzymes in trout: A comparative in vitro/in vivo-assessment using cultured hepatocytes. Aquat Toxicol 53:229-245.
20. Egaas E, Sandvik M, Fjeld E, Källqvist T, Goksoyr A, Svensen A. 1999. Some effects of the fungicide propiconazole on cytochrome P450 and glutathione S-transferase in brown trout (Salmo trutta). Comp Biochem Physiol C 112:337-344.
21. Stegeman JJ, Hahn ME. 1994. Biochemistry and molecular biology of monooxygenases: Current perspectives on forms, functions, and regulation of cytochrome P450 in aquatic species. In Ostrander GK, Malins D, eds, Aquatic Toxicology: Molecular, Biochemical, and Cellular Perspectives. Lewis, Boca Raton, FL, USA, pp 87-206.
22. Dresser GK, Spence JD, Bailey DG. 2000. Pharmacokinetic-pharmacodynamic consequences and clinical relevance of cytochrome P450 3A4 inhibition. Clin Pharmacokinet 38:41-57.
23. Berry MN, Friend DS. 1969. High-yield preparation of isolated rat parenchymal cells: A biochemical and fine structural study. J Cell Biol 43:506-520.
24. Pesonen M, Andersson T. 1991. Characterization and induction of xenobiotics metabolizing enzyme activities in a primary culture of rainbow trout hepatocytes. Xenobiotica 21:461-471.
25. Förlin L. 1980. Effects of Clophen A50, 3-methylcholanthrene, pregnenolone-16α-carbonotrile, and phenobarbital on the hepatic microsomal cytochrome P450 dependent mono-oxygenase system in rainbow trout, Salmo gairdneri, of different age and sex. Toxicol Appl Pharmacol 54:420-430.
26. Celander M, Hahn ME, Stegeman JJ. 1996. Cytochromes (CYP) in the Poeciliopsis lucida hepatocellular carcinoma cell line (PLHC-1). Dose- and time-dependent glucocorticoid potentiation of induction of CYP1A without induction of CYP3A. Arch Biochem Biophys 329:113-122.
27. Hahn ME, Lamb TM, Schultz ME, Smolowitz RM, Stegeman JJ. 1993. Cytochrome P4501A induction and inhibition by 3,3′,4,4′ -tetrachlorobiphenyl in an Ah receptor containing fish hepatoma cell line (PLHC-1). Aquat Toxicol 26:185-208.
28. Yawetz A, Woodin B, Stegeman JJ. 1998. Cytochromes P450 in liver of the turtle Chrysemys picta picta and the induction and partial purification of CYP1A-like proteins. Biochim Biophys Acta 1381:12-26.
29. Celander M, Buhler DR, Förlin L, Goksoyr A, Miranda CL, Woodin BR, Stegeman JJ. 1996. Immunochemical relationships of cytochrome P4503A-like proteins in teleost fish. Fish Physiol Biochem 15:323-332.
30. Celander M, Förlin L. 1991. Catalytic activity and immunochemical quantification of hepatic cytochrome P450 in β-naphthoflavone and isosafrol treated rainbow trout (Oncorhynchus mykiss). Fish Physiol Biochem 9:189-197.
31. Celander M, Ronis M, Förlin L. 1989. Initial Characterization of a constitutive cytochrome P450 isoenzyme in rainbow trout liver. Mar Environ Res 28:9-13.
32. Park SS, Miller H, Klotz AV, Kloepper-Sams PJ, Stegeman JJ, Gelboin HV. 1986. Monoclonal antibodies to liver microsomal cytochrome P450E of the marine fish Stenotomus chrysops (scup): Cross reactivity with 3-methylcholanthrene induced rat cytochrome P450. Arch Biochem Biophys 249:339-350.
33. Cambell PM, Devlin RH. 1996. Expression of CYP1A1 in livers and gonads of Pacific salmon: Quantitation of mRNA levels by RT-cPCR. Aquat Toxicol 34:47-69.
34. Pfaffl MW. 2001. A new mathematical model for relative quantification in real-time RT-PCR. Nucleic Acids Res 29:202-207.
35. The Swedish National Chemicals Inspectorate. 1988. Ämnen mot svampangrepp. PM Nr 6/98. Technical Report. Stockholm, Sweden.
36. Bertilsson G, Heidrich J, Svensson K, Asman M, Jendeberg L, Sydow-Bäckman M, Ohlsson R, Postlind H, Blomquist P, Berkenstam A. 1998. Identification of a human nuclear receptor defines a new signaling pathway for CYP3A induction. Proc Natl Acad Sci U S A 95:12208-12213.
37. Kliewer SA, Goodwin B, Willson TM. 2002. The nuclear pregnane X receptor: A key regulator of xenobiotic metabolism. Endocr Rev 23:687-702.
38. Hodgson E, Smart RC. 2001. Introduction to Biochemical Toxicology, 3rd ed. Wiley-Interscience, Indianapolis, IN, USA.
39. Turan VK, Mishin VM, Thomas PE. 2001. Clotrimazole is a selective and potent inhibitor of rat cytochrome P450 3A subfamily-related testosterone metabolism. Drug Metab Dispos 29:837-842.
40. Levine SL, Oris JT. 1999. Noncompetitive mixed-type inhibition of rainbow trout CYP1A catalytic activity by clotrimazole. Comp Biochem Physiol C 122:205-210.