Metabolism related toxicity of diclofenac in yeast as model system

Toxicology Letters

Volumn 200, Issue 3, 2011, Pages 162-168

  van Leeuwen, Jolanda S ^a   Vredenburg, Galvin ^a   Dragovic, Sanja ^a   Tjong, T F Jennifer ^a   Vos, J Chris ^a   Vermeulen, Nico P E ^a  

^a VU UNIVERSITY AMSTERDAM   (Netherlands)

Author keywords

Cytochrome P450; Diclofenac; Oxidative metabolism; Reactive oxygen species; Yeast

Indexed keywords

4' HYDROXYDICLOFENAC; 5 HYDROXYDICLOFENAC; CYTOCHROME P450; DICLOFENAC; DRUG METABOLITE; GLUTATHIONE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; DRUG METABOLISM; DRUG TOXICITY; FUNGUS GROWTH; IN VITRO STUDY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; SACCHAROMYCES CEREVISIAE;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIOTRANSFORMATION; BLOTTING, WESTERN; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DICLOFENAC; HYDROXYLATION; IMINES; OXIDATION-REDUCTION; PLASMIDS; QUINONES; REACTIVE OXYGEN SPECIES; SACCHAROMYCES CEREVISIAE; SOLUTIONS; SPECTROPHOTOMETRY, ULTRAVIOLET;

SACCHAROMYCES CEREVISIAE;

EID: 78651105830     PISSN: 03784274     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxlet.2010.11.010     Document Type: Article

References (40)

1. Aoyama T., Yamano S., Guzelian P.S., Gelboin H.V., Gonzalez F.J. 5 of 12 forms of vaccinia virus-expressed human hepatic cytochrome-P450 metabolically activate aflatoxin-B1. Proc. Natl. Acad. Sci. U.S.A. 1990, 87:4790-4793.
2. Blum W., Faigle J.W., Pfaar U., Sallmann A. Characterization of a novel diclofenac metabolite in human urine by capillary gas chromatography-negative chemical ionization mass spectrometry. J. Chromatogr. B: Biomed. Appl. 1996, 685:251-263.
3. Bort R., Ponsoda X., Jover R., Gomez-Lechon M.J., Castell J.V. Diclofenac toxicity to hepatocytes: a role for drug metabolism in cell toxicity. J. Pharmacol. Exp. Ther. 1999, 288:65-72.
4. Damsten M.C., van Vugt-Lussenburg B.M., Zeldenthuis T., de Vlieger J.S., Commandeur J.N., Vermeulen N.P. Application of drug metabolising mutants of cytochrome P450 BM3 (CYP102A1) as biocatalysts for the generation of reactive metabolites. Chem. Biol. Interact. 2008, 171:96-107.
5. Del Carratore M.R., Mezzatesta C., Hidestrand M., Neve P., Amato G., Gervasi P.G. Cloning and expression of rat CYP2E1 in Saccharomyces cerevisiae: detection of genotoxicity of N-alkylformamides. Environ. Mol. Mutagen. 2000, 36:97-104.
6. Ding S.H., Yao D.G., Burchell B., Wolf C.R., Friedberg T. High levels of recombinant CYP3A4 expression in Chinese hamster ovary cells are modulated by coexpressed human P450 reductase and hemin supplementation. Arch. Biochem. Biophys. 1997, 348:403-410.
7. Gomez-Lechon M.J., Ponsoda X., O'Connor E., Donato T., Castell J.V., Jover R. Diclofenac induces apoptosis in hepatocytes by alteration of mitochondrial function and generation of ROS. Biochem. Pharmacol. 2003, 66:2155-2167.
8. Gomez-Lechon M.J., Castell J.V., Donato M.T. Hepatocytes-the choice to investigate drug metabolism and toxicity in man: in vitro variability as a reflection of in vivo. Chem. Biol. Interact. 2007, 168:30-50.
9. Grillo M.P., Ma J., Teffera Y., Waldon D.J. A novel bioactivation pathway for diclofenac initiated by P450 mediated oxidative decarboxylation. Drug Metab. Dispos. 2008, 36:1740-1744.
10. Guo Y., Breeden L.L., Zarbl H., Preston B.D., Eaton D.L. Expression of a human cytochrome P450 in yeast permits analysis of pathways for response to and repair of aflatoxin-induced DNA damage. Mol. Cell Biol. 2005, 25:5823-5833.
11. Inoue A., Muranaka S., Fujita H., Kanno T., Tamai H., Utsumi K. Molecular mechanism of diclofenac-induced apoptosis of promyelocytic leukemia: dependency on reactive oxygen species, Akt, Bid, cytochrome and caspase pathway. Free Radic. Biol. Med. 2004, 37:1290-1299.
12. Kenny J.R., Maggs J.L., Meng X., Sinnott D., Clarke S.E., Park B.K., Stachulski A.V. Syntheses and characterization of the acyl glucuronide and hydroxy metabolites of diclofenac. J. Med. Chem. 2004, 47:2816-2825.
13. King C., Tang W., Ngui J., Tephly T., Braun M. Characterization of rat and human UDP-glucuronosyltransferases responsible for the in vitro glucuronidation of diclofenac. Toxicol. Sci. 2001, 61:49-53.
14. Klebe R.J., Harriss J.V., Sharp Z.D., Douglas M.G. A general method for polyethylene-glycol-induced genetic transformation of bacteria and yeast. Gene 1983, 25:333-341.
15. Komuro M., Higuchi T., Hirobe M. Application of chemical cytochrome-P-450 model systems to studies on drug-metabolism. 8. Novel metabolism of carboxylic-acids via oxidative decarboxylation. Bioorg. Med. Chem. 1995, 3:55-65.
16. Kretz-Rommel A., Boelsterli U.A. Diclofenac covalent protein-binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes. Toxicol. Appl. Pharmacol. 1993, 120:155-161.
17. Lafontaine D., Tollervey D. One-step PCR mediated strategy for the construction of conditionally expressed and epitope tagged yeast proteins. Nucleic Acids Res. 1996, 24:3469-3471.
18. Laine L., Goldkind L., Curtis S.P., Connors L.G., Yanqiong Z., Cannon C.P. How common is diclofenac-associated liver injury? Analysis of 17,289 arthritis patients in a long-term prospective clinical trial. Am. J. Gastroenterol. 2009, 104:356-362.
19. LeCluyse E.L. Human hepatocyte culture systems for the in vitro evaluation of cytochrome P450 expression and regulation. Eur. J. Pharm. Sci. 2001, 13:343-368.
20. Leemann T., Transon C., Dayer P. Cytochrome P450TB (CYP2C): a major monooxygenase catalyzing diclofenac 4′-hydroxylation in human liver. Life Sci. 1993, 52:29-34.
21. Lim M.S., Lim P.L., Gupta R., Boelsterli U.A. Critical role of free cytosolic calcium, but not uncoupling, in mitochondrial permeability transition and cell death induced by diclofenac oxidative metabolites in immortalized human hepatocytes. Toxicol. Appl. Pharmacol. 2006, 217:322-331.
22. Madsen K.G., Skonberg C., Jurva U., Cornett C., Hansen S.H., Johansen T.N., Olsen J. Bioactivation of diclofenac in vitro and in vivo: correlation to electrochemical studies. Chem. Res. Toxicol. 2008, 21:1107-1119.
23. Masubuchi Y., Yamada S., Horie T. Possible mechanism of hepatocyte injury induced by diphenylamine and its structurally related nonsteroidal anti-inflammatory drugs. J. Pharmacol. Exp. Ther. 2000, 292:982-987.
24. Masubuchi Y., Ose A., Horie T. Diclofenac-induced inactivation of CYP3A4 and its stimulation by quinidine. Drug Metab. Dispos. 2002, 30:1143-1148.
25. Menacho-Marquez M., Murguia J.R. Yeast on drugs: Saccharomyces cerevisiae as a tool for anticancer drug research. Clin. Transl. Oncol. 2007, 9:221-228.
26. Miyamoto G., Zahid N., Uetrecht J.P. Oxidation of diclofenac to reactive intermediates by neutrophils, myeloperoxidase, and hypochlorous acid. Chem. Res. Toxicol. 1997, 10:414-419.
27. Munro A.W., Leys D.G., McLean K.J., Marshall K.R., Ost T.W., Daff S., Miles C.S., Chapman S.K., Lysek D.A., Moser C.C., Page C.C., Dutton P.L. P450 BM3: the very model of a modern flavocytochrome. Trends Biochem. Sci. 2002, 27:250-257.
28. Naisbitt D.J., Sanderson L.S., Meng X.L., Stachulski A.V., Clarke S.E., Park B.K. Investigation of the immunogenicity of diclofenac and diclofenac metabolites. Toxicol. Lett. 2007, 168:45-50.
29. Pompon D., Gautier J.C., Perret A., Truan G., Urban P. Simulation of human xenobiotic metabolism in microorganisms - yeast a good compromise between E. coli and human cells. J. Hepatol. 1997, 26:81-85.
30. Poon G.K., Chen Q., Teffera Y., Ngui J.S., Griffin P.R., Braun M.P., Doss G.A., Freeden C., Stearns R.A., Evans D.C., Baillie T.A., Tang W. Bioactivation of diclofenac via benzoquinone imine intermediates - identification of urinary mercapturic acid derivatives in rats and humans. Drug Metab. Dispos. 2001, 29:1608-1613.
31. Raungrut P., Uchaipichat V., Elliot D.J., Janchawee B., Somogyi A.A., Miners J.O. In vitro-in vivo extrapolation predicts drug-drug interactions arising from inhibition of codeine glucuronidation by dextropropoxyphene, fluconazole, ketoconazole, and methadone in humans. J. Pharmacol. Exp. Ther. 2010, 334:609-618.
32. Renaud J.P., Peyronneau M.a., Urban P., Truan G., Cullin C., Pompon D., Beaune P., Mansuy D. Recombinant yeast in drug metabolism. Toxicology 1993, 82:39-52.
33. Shen S.J., Marchick M.R., Davis M.R., Doss G.A., Pohl L.R. Metabolic activation of diclofenac by human cytochrome P450 3A4: role of 5-hydroxydiclofenac. Chem. Res. Toxicol. 1999, 12:214-222.
34. Takeda S., Kitajima Y., Ishii Y., Nishimura Y., Mackenzie P.I., Oguri K., Yamada H. Inhibition of UDP-glucuronosyltransferase 2b7-catalyzed morphine glucuronidation by ketoconazole: dual mechanisms involving a novel noncompetitive mode. Drug Metab. Dispos. 2006, 34:1277-1282.
35. Tang W., Stearns R.A., Wang R.W., Chiu S.H., Baillie T.A. Roles of human hepatic cytochrome P450s 2C9 and 3A4 in the metabolic activation of diclofenac. Chem. Res. Toxicol. 1999, 12:192-199.
36. Tang W., Stearns R.A., Bandiera S.M., Zhang Y., Raab C., Braun M.P., Dean D.C., Pang J.M., Leung K.H., Doss G.A., Strauss J.R., Kwei G.Y., Rushmore T.H., Chiu S.H.L., Baillie T.A. Studies on cytochrome P450-mediated bioactivation of diclofenac in rats and in human hepatocytes: Identification of glutathione conjugated metabolites. Drug Metab. Dispos. 1999, 27:365-372.
37. van Leeuwen, J.S., Orij, R., Luttik, M.A., Smits, G.J., Vermeulen, N.P., Vos, J.C., 2010. Subunits Rip1p and Cox9p of the respiratory chain contribute to diclofenac-induced mitochondrial dysfunction. Microbiology, in press.
38. Van Vugt-Lussenburg B.M., Stjernschantz E., Lastdrager J., Oostenbrink C., Vermeulen N.P., Commandeur J.N. Identification of critical residues in novel drug metabolizing mutants of cytochrome P450 BM3 using random mutagenesis. J. Med. Chem. 2007, 50:455-461.
39. Wang E.J., Lew K., Casciano C.N., Clement R.P., Johnson W.W. Interaction of common azole antifungals with P glycoprotein. Antimicrob. Agents Chemother. 2002, 46:160-165.
40. Yan Z., Li J., Huebert N., Caldwell G.W., Du Y., Zhong H. Detection of a novel reactive metabolite of diclofenac: evidence for CYP2C9-mediated bioactivation via arene oxides. Drug Metab. Dispos. 2005, 33:706-713.