Cross-species comparison of conazole fungicide metabolites using rat and rainbow trout (Onchorhynchus mykiss) hepatic microsomes and purified human CYP 3A4

Environmental Science and Technology

Volumn 42, Issue 3, 2008, Pages 947-954

  Mazur, Christopher S ^a   Kenneke, John F ^a  

^a U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EXTRAPOLATION; FUNGI; METABOLITES; PROTEINS; RISK ASSESSMENT; TOXICITY;

CONAZOLE FUNGICIDE METABOLITES; CROSS-SPECIES; HEPATIC MICROSOMES;

FUNGICIDES;

AGRICULTURAL CHEMICAL; ALIPHATIC COMPOUND; CARBONYL DERIVATIVE; CYTOCHROME P450 3A4; DRUG ADDITIVE; FUNGICIDE; PYRROLE DERIVATIVE; XENOBIOTIC AGENT;

EXTRAPOLATION; FUNGI; FUNGICIDES; METABOLITES; PROTEINS; RISK ASSESSMENT; TOXICITY;

BIOTRANSFORMATION; COMPARATIVE STUDY; COMPLEXATION; ENZYME ACTIVITY; FUNGICIDE; METABOLITE; MICROCOSM; RISK ASSESSMENT; RODENT; SALMONID; TOXICITY; XENOBIOTICS;

ACUTE TOXICITY; AQUATIC SPECIES; ARTICLE; BIOTRANSFORMATION; CELL WALL; COMPLEX FORMATION; DRUG METABOLISM; ENZYME ACTIVITY; EXPOSURE; HYDROXYLATION; LIVER MICROSOME; MAMMAL; NONHUMAN; RAINBOW TROUT; RAT; REDUCTION; RISK ASSESSMENT;

ANIMALS; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 CYP3A; FUNGICIDES, INDUSTRIAL; HUMANS; MALE; MASS SPECTROMETRY; MICROSOMES, LIVER; ONCORHYNCHUS MYKISS; RATS; RATS, SPRAGUE-DAWLEY; REFERENCE STANDARDS; SPECIES SPECIFICITY; TRIAZOLES;

MAMMALIA; ONCORHYNCHUS MYKISS; RATTUS; SALMONIDAE;

EID: 38949088929     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es072049b     Document Type: Article

References (40)

1. Wilson, V. S.; Cardon, M. C.; Thornton, J.; Korte, J. J.; Ankley, G. T.; Welch, J.; Gray, L. E.; Hartig, P. C. Cloning and in vitro expression and characterization of the androgenreceptor and isolation of estrogen receptor from the fathead minnow (Pimephasles romelas). Environ. Sci. Technol. 2004, 38 (23), 6314-6321.
2. Dyer, S. D.; Versteeg, D. J.; Belanger, S. E.; Chaney, J. G.; Mayer, F. L. Interspeciescorrelation estimates predict protective environmental concentrations. Environ. Sci. Technol. 2006, 40 (9), 3102-3111.
3. Miracle, A. L.; Ankley, G. T. Ecotoxicogenomics: linkages between exposure andeffects in assessing risks of aquatic contaminants to fish. Reprod. Toxicol. 2005, 19, (3), 321-326.
4. Ohyama, K.; Maki, S.; Sato, K.; Kato, Y. In vitro metabolism of [C-14] methoxychlor inrat, mouse, Japanese quail and rainbow trout in precision-cut liver slices. Xenobiotica 2004, 34 (8), 741-754.
5. Sturm, A.; Cravedi, J. P.; Perdu, E.; Baradat, M.; Segner, H. Effects of prochlorazand nonylphenol diethoxylate on hepatic biotransformation enzymes in trout: acomparative in vitro/in vivo-assessment using cultured hepatocytes. Aquat. Toxicol. 2001, 53 (3-4), 229-245.
6. Goksoyr, A.; Forlin, L. The cytochrome P-450 system in fish, aquatic toxicology andenvironmental monitoring. Aquat. Toxicol. 1992, 22 (4), 287-311.
7. Bogaards, J. J. P.; Bertrand, M.; Jackson, P.; Oudshoorn, M. J.; Weaver, R. J.; Vasn Bladeren, P. J.; Walther, B. Determining the best animal model for human cytochrome P450 activities: a comparison of mouse, rat, rabbit, dog, micropig, monkey and man. Xenobiotica 2000, 30 (12), 1131-1152.
8. Riley, R. J.; Parker, A. J.; Trigg, S.; Manners, C. N. Development of a generalized,quantitative physicochemical model of CYP3A4 inhibition for use in early drug discovery. Pharm. Res. 2001, 18 (5), 652-655.
9. Austin, R. P.; Barton, P.; Cockroft, S. L.; Wenlock, M. C.; Riley, R. J. The influence of nonspecific microsomal binding on apparent intrinsic clearance, and its prediction from physicochemical properties. Drug Metab. Dispos. 2002, 30 (12), 1497-1503.
10. Lipscomb, J. C.; Kedderis, G. L. Incorporating human interin- dividualbiotransformation variance in health risk assessment. Sci. Total Environ. 2002, 288 (1-2), 13-21.
11. Goetz, A. K.; Bao, W.; Ren, H.; Schmid, J. E.; Tully, D. B.; Wood, C.; Rockett, J. C.; Narotsky, M. G.; Sun, G.; Lambert, G. R. Gene expression profiling in the liver of CD-1 mice to characterize the hepatotoxicity of triazole fungicides. Toxicol. Appl. Pharmacol. 2006, 215 (3), 274-284.
12. Tully, D. B.; Bao, W.; Goetz, A. K.; Blystone, C. R.; Ren, H.; Schmid, J. E.; Strader, L. F.; Wood, C. R.; Best, D. S.; Narotsky, M. G. Gene expression profiling in liver and testis of rats to characterize the toxicity of triazole fungicides. Toxicol. Appl. Pharmacol. 2006, 215 (3), 260-273.
13. Venkatakrishnan, K.; von Moltke, L. L.; Greenblatt, D. J. Effects of the anitfungalagents on oxidative drug metabolism. Clin. Pharmacokinet. 2000, 38 (2), 111-180.
14. Ankley, G. T.; Jensen, K. M.; Durhan, E. J.; Makynen, E. A.; Butterworth, B. C.; Kahl, M. D.; Villeneuve, D. L.; Linnum, A.; Gray, L. E.; Cardon, M.; Wilson, V. S. Effects of two fungicides with multiple modes of action on reproductive endocrine function in thefathead minnow (Pimephales promelas). Toxicol. Sci. 2005, 86 (2), 300-308.
15. Robbertse, B.; van der Rijst, M.; van Aarde, I. M. R.; Lennox, C.; Crous, P. W. DMIsensitivity and cross-resistance patterns of Rhynchosporium secalis isolatesfrom South Africa. Crop Prot. 2001, 20 (2), 97-102.
16. Zarn, J. A.; Bruschweiler, B. J.; Schlatter, J. R. Effects of azole fungicides on mammalian steroidogenesis by inhibiting sterol 14 alpha-demethylase and aromatase. Environ. Health Perspect. 2003, 1, 15.
17. Allen, J. W.; Wolf, D. C.; George, M. H.; Hester, S. D.; Guobin, S.; Sheau-Fung, T.; Delker, D. A.; Moore, T.; Jones, C.; Nelson, G.; Roop, B. C.; Leavitt, S.; Winkfield, E.; Ward, W. O.; Nesnow, S. Toxicity profiles in mice treated with hepatotumorigenic andnon-hepatotumorigenic triazole conazole fungicides: propiconazole, triadimefon, and myclobutanil. Toxicol. Pathol. 2006, 34 (7), 853-862.
18. Hester, S. D.; Wolf, D. C.; Nesnow, S.; Sheau-Fung, T. Transcriptional profiles in liver from rats treated with tumorigenic and non-tumorigenic triazole conazole fungicides: propiconazole, triadimefon, and myclobutanil. Toxicol. Pathol. 2006, 34 (7), 879-894.
19. U.S. Environmental Protection Agency. Determination of the Appropriate FQPA Safety Factor(S) in Tolerance Assessment-,February, 2002; Office of Pesticide Programs, U.S. EPA: Washington, D.C., 2002.
20. Nelson, D. R.; Zeldin, D. C.; Hoffman, S. M.; Maltais, L. J.; Wain, H. M.; Nebert, D. W. Comparison of cytochrome P450 (CYP) genes from the mouse and human genomes, including nomenclature recommendations for genes, pseudogenes and alternative-splice variants. Pharmacogenetics 2004, 14, 1-18.
21. Sun, G.; Thai, S.-F.; Tully, D. B.; Lambert, G. R.; Goetz, A. K.; Wolf, D. C.; Dix, D. J.; Nesnow, S. Propiconazole-induced cytochrome P450 gene expression and enzymatic activities in rat and mouse liver. Toxicol. Lett. 2005, 155 (2), 277-287.
22. Kolanczyk, R.; Schmieder, P.; Bradbury, S.; Spizzo, T. Biotransformation of 4-methoxyphenol in rainbowtrout (Oncorhynchus mykiss) hepatic microsomes. Aquat. Toxicol. 1999, 45 (1), 47-61.
23. Konwick, B. J.; Garrison, A. W.; Black, M. C.; Avants, J. K.; Fisk, A. T. Bioaccumulation, biotransformation, and metabolite formation of fipronil and chirallegacy pesticides in rainbow trout. Environ. Sci. Technol. 2006, 40 (9), 2930-2936.
24. Konwick, B. J.; Garrison, A. W.; Avants, J. K.; Fisk, A. T. Bioaccumulation and biotransformation of chiral triazole fungicides in rainbow trout (Oncorhynchus mykiss). Aquat. Toxicol. 2006, 80 (4), 372-381.
25. Makynen, E. A.; Kahl, M. D.; Jensen, K. M.; Tietge, J. E.; Wells, K. L.; Van DerKraak, G.; Ankley, G. T. Effects of the mammalian antiandrogen vinclozolin on developmentand reproduction of the fathead minnow (Pimephales promelas). Aquat. Toxicol. 2000, 48 (4), 461-475.
26. Sinclair, C. J.; Boxall, A. B. A. Assessing the ecotoxicity of pesticide transformationproducts. Environ. Sci. Technol. 2003, 37 (20), 4617-4625.
27. Smith, D. A.; Obach, R. S. Seeing through the mist: Abundance versus percentage. Commentary on metabolites in safety testing. Drug Metab. Dispos. 2005, 33 (10), 1409-1417.
28. Rogiers, V.; Adriaenssens, L.; Vandenberghe, Y.; Gepts, E.; Callaerts, A. Vercruysse. Critical evaluation of 7-ethoxycoumarin O-deethylase activity measurment in intact isolated rat hepatocytes. Xenobiotica 1986, 16 (9), 817-826.
29. Bradford, M. M. A rapid and sensitive method for the quantification of microgramquantities of protein utilizing protein-dye binding. Anal. Chem. 1976, 72, 248-254.
30. Estabrook, R.; Teterson, W. J.; Baron, J.; Hildebrandt, A. G. The spectrophotometric measurment of turbid suspensions of cytochromes associated withdrug metabolism. Methods Pharmacol. 1972, 2, 303-350.
31. Barton, H. A.; Tang, J.; Sey, Y. M.; Stanko, J. P.; Murrell, R. N.; Rockett, J. G.; Dix, D. J. Metabolism of myclobutanil and triadimefon by human and rat cytochrome P450 enzymes and liver microsomes. Xenobiotica 2006, 36 (9), 793-806.
32. Sun, G.; Grindstaff, R. D.; Thai, S. F.; Lambert, G. R.; Tully, D. B.; Dix, D. J.; Nesnow, S. Induction of cytochrome P450 enzymes in rat liver by two conazoles, myclobutanil and triadimefon. Xenobiotica 2007, 37 (2), 180-193.
33. Mazur, C. S.; Kenneke, J. F.; Tebes-Stevens, C.; Okino, M. S.; Lipscomb, J. C. In vitro metabolism of the fungicide and environmental contaminant trans-bromuconazole and implications for risk assessment. J. Toxicol. Environ. Health, Part A 2007, 70, (14), 1241-1250.
34. Kramer, H. J.; van den Berg, M.; Delang, R. J.; Brandsma, L.; Dejongh, J. Biotransformation rates of Ugilec 141(R) (tetrachlorobenzyltoluenes) in rat and trout microsomes. Chemosphere 2000, 40 (9-11), 1283-1288.
35. Nabb, D. L.; Mingoia, R. T.; Yang, C.-H.; Han, X. Comparison of basal level metabolic enzyme activities of freshly isolated hepatocytes from rainbow trout (Oncorhynchus mykiss) and rat. Aquat. Toxicol. 2006, 80 (1), 52-59.
36. Babin, M.; Casado, S.; Chana, A.; Herradon, B.; Segner, H.; Tarazona, J. V.; Navas, J.M. Cytochrome P4501A induction caused by the imidazole derivative prochloraz in arainbow trout cell line. Toxicol. In Vitro 2005, 19 (7), 899-902.
37. Hegelund, T.; Ottosson, K.; Radinger, M.; Tomberg, P.; Celander, M. C. Effects of the antifungal imidazole ketoconazole on CYPIA and CYP3A in rainbow trout and killifish. Environ. Toxicol. Chem. 2004, 23 (5), 1326-1334.
38. Wolf, D. C.; Allen, J. W.; George, M. H.; Hester, S. D.; Sun, G.; Moore, T.; Sheau-Fung, T.; Delker, D.; Winkfield, E.; Leavitt, S.; Nelson, G.; Roop, B. C.; Jones, C.; Thibodeaux, J.; Nesnow, S. Toxicity profiles in rats treated with tumorigenic and nontumorigenic triazole conazole fungicides: propiconazole, triadimefon, andmyclobutanil. Toxicol. Pathol. 2006, 34 (7), 895-902.
39. Levine, S. L.; Oris, J. T.; Denison, M. S. Modulation of CYP1A expression inrainbow trout by a technical grade formulation of propiconazole. Environ. Toxicol. Chem. 1999, 18 (11), 2565-2573.
40. Rosemond, M. J.; Walsh, J. S. Human carbonyl reduction pathways and a strategy for their study in vitro. Drug Metab. Rev. 2004, 36 (2), 335-361.