Cytochrome P450 oxidation of the thiophene-containing anticancer drug 3-[(quinolin-4-ylmethyl)-amino]-thiophene-2-carboxylic acid (4-trifluoromethoxy- phenyl)-amide to an electrophilic intermediate

Chemical Research in Toxicology

Volumn 21, Issue 8, 2008, Pages 1570-1577

  Medower, Christine ^a,c   Wen, Lian ^a,b   Johnson, William W ^a  

^a OSI PHARMACEUTICALS INC   (United States)

^b ABC Laboratories Incorporated   (United States)

^c ABC Laboratories Inc ^*

Author keywords

[No Author keywords available]

Indexed keywords

3 [(QUINOLIN 4 YLMETHYL) AMINO] THIOPHENE 2 CARBOXYLIC ACID (4 TRIFLUOROMETHOXY PHENYL) AMIDE; ANTINEOPLASTIC AGENT; CYTOCHROME P450; DEUTERIUM; SULFOXIDE; THIOPHENE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MICHAEL ADDITION; MOLECULE; OXIDATION; PHYTOCHEMISTRY; TANDEM MASS SPECTROMETRY;

ANTINEOPLASTIC AGENTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CYTOCHROME P-450 ENZYME SYSTEM; DNA DAMAGE; DNA-BINDING PROTEINS; GLUTATHIONE; HALF-LIFE; HUMANS; LIVER; MICROSOMES, LIVER; OXIDATION-REDUCTION; PROTEIN BINDING; QUINOLINES; RECOMBINANT PROTEINS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFOXIDES; TANDEM MASS SPECTROMETRY; THIOPHENES;

RATTUS;

EID: 51449109566     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700430n     Document Type: Article

References (46)

1. Ebermann, R., Alth, G., Kreitner, M., and Kubin, A. (1996) Natural products derived from plants as potential drugs for the photodynamic destruction of tumor cells. J. Photochem. Photobiol. B 36 (2), 95-97.
2. Dyreborg, S., Arvin, E., and Broholm, K. (1996) Effects of creosote compounds on the aerobic bio-degradation of benzene. Biodegradation 7 (3), 191-201.
3. Dalvie, D. K., Kalgutkar, A. S., Khojasteh-Bakht, S. C., Obach, R. S., and O'Donnell, J. P. (2002) Biotransformation reactions of five-membered aromatic heterocyclic rings. Chem. Res. Toxicol. 15 (3), 269-299.
4. Dansette, P. M., Thang, D. C., el Amri, H., and Mansuy, D. (1992) Evidence for thiophene-S-oxide as a primary reactive metabolite of thiophene in vivo: Formation of a dihydrothiophene sulfoxide mercapturic acid. Biochem. Biophys. Res. Commun. 186, 1624-1630.
5. Mansuy, D., Valadon, P., Erdelmeier, I., Lopez-Garcia, P., Amar, C., Girault, J. P., and Dansette, P. M. (1991) Thiophene S-oxides as new reactive metabolites: Formation by cytochrome P-450 dependent oxidation and reaction with nucleophiles. J. Am. Chem. Soc. 113, 7825-7826.
6. Valadon, P., Dansette, P. M., Girault, J. P., Amar, C., and Mansuy, D. (1996) Thiophene sulfoxides as reactive metabolites: Formation upon microsomal oxidation of a 3-aroylthiophene and fate in the presence of nucleophiles in vitro and in vivo. Chem. Res. Toxicol. 9, 1403-1413.
7. Treiber, A., Dansette, P. M., El Amri, H., Girault, J. P., Ginderow, D., Mornon, J.-P., and Mansuy, D. (1997) Chemical and biological oxidation of thiophene: Preparation and complete characterization of thiophene S-oxide dimers and evidence for thiophene 5-oxide as an intermediate in thiophene metabolism in vivo and in vitro. J. Am. Chem. Soc. 119, 1565-1571.
8. Guengerich, F. P. (2003) Cytochromes P450, drugs, and diseases. Mol. Interv. 3 (4), 194-204.
9. Guengerich, F. P. (2005) Generation of reactive intermediates. J. Biochem. Mol. Toxicol. 19 (3), 173-174.
10. Guengerich, F. P. (2006) Cytochrome P450s and other enzymes in drug metabolism and toxicity. AAPS J. 8 (1), E101-E111.
11. Guengerich, F. P., and Macdonald, J. S. (2007) Applying mechanisms of chemical toxicity to predict drug safety. Chem. Res. Toxicol. 20 (3), 344-369.
12. Park, B. K., Kitteringham, N. R., Maggs, J. L., Pirmohamed, M., and Williams, D. P. (2005) The role of metabolic activation in drug-induced hepatotoxicity. Annu. Rev. Pharmacol. Toxicol. 45, 177-202.
13. Kaplowitz, N. (2005) Idiosyncratic drug hepatotoxicity. Nat. Rev. Drug Discovery 4 (6), 489-499.
14. Williams, D. P., O'Donnell, C. J., Maggs, J. L., Leeder, J. S., Uetrecht, J., Pirmohamed, M., and Park, B. K. (2003) Bioactivation of clozapine by murine cardiac tissue in vivo and in vitro. Chem. Res. Toxicol. 16 (10), 1359-1364.
15. Hinson, J. A., Pumford, N. R., and Roberts, D. W. (1995) Mechanisms of acetaminophen toxicity: immunochemical detection of drug-protein adducts. Drug Metab. Rev. 27 (1-2), 73-92.
16. Kretz-Rommel, A., and Boelsterli, U. A. (1994) Selective protein adducts to membrane proteins in cultured rat hepatocytes exposed to diclofenac: radiochemical and immunochemical analysis. Mol. Pharmacol. 45 (2), 237-244.
17. Pumford, N. R., Myers, T. G., Davila, J. C., Highet, R. J., and Pohl, L. R. (1993) Immunochemical detection of liver protein adducts of the nonsteroidal antiinflammatory drug diclofenac. Chem. Res. Toxicol. 6 (2), 147-150.
18. Munns, A. J., De Voss, J. J., Hooper, W. D., Dickinson, R. G., and Gillam, E. M. (1997) Bioactivation of phenytoin by human cytochrome P450: characterization of the mechanism and targets of covalent adduct formation. Chem. Res. Toxicol. 10 (9), 1049-1058.
19. Maggs, J. L., Grabowski, P. S., and Park, B. K. (1983) Drug protein conjugates-III. Inhibition of the irreversible binding of ethinylestradiol to rat liver microsomal protein by mixed-function oxidase inhibitors, ascorbic acid and thiols. J. Steroid Biochem. 19 (3), 1273-1278.
20. Chaudhary, A. K., Nokubo, M., Reddy, G. R., Yeola, S. N., Morrow, J. D., Blair, I. A., and Marnett, L. J. (1994) Detection of endogenous malondialdehyde-deoxyguanosine adducts in human liver. Science 265, 1580-1582.
21. Plastaras, J. P., Guengerich, F. P., Nebert, D. W., and Marnett, L. J. (2000) Xenobiotic-metabolizing cytochromes P450 convert prostaglandin endoperoxide to hydroxyheptadecatrienoic acid and the mutagen, malondialdehyde. J. Biol. Chem. 275, 11784-11790.
22. West, J. D., and Marnett, L. J. (2006) Endogenous reactive intermediates as modulators of cell signaling and cell death. Chem. Res. Toxicol. 19, 173-194.
23. Alderson, N. L., Wang, Y., Blatnik, M., Frizzell, N., Walla, M. D., Lyons, T. J., Alt, N., Carson, J. A., Nagai, R., Thorpe, S. R., and Baynes, J. W. (2006) S-(2-Succinyl) cysteine: A novel chemical modification of tissue proteins by a Krebs cycle intermediate. Arch. Biochem. Biophys. 450, 1-8.
24. Januszewski, A. S., Alderson, N. L., Jenkins, A. J., Thorpe, S. R., and Baynes, J. W. (2005) Chemical modification of proteins during peroxidation of phospholipids. J. Lipid Res. 46, 1440-1449.
25. Skordos, K. W., Skiles, G. L., Laycock, J. D., Lanza, D. L., and Yost, G. S. (1998) Evidence supporting the formation of 2,3-epoxy-3-methylindoline: a reactive intermediate of the pneumotoxin 3-methylindole. Chem. Res. Toxicol. 11 (7), 741-749.
26. Petti, F., Thelemann, A., Kahler, J., McCormack, S., Castaldo, L., Hunt, T., Nuwaysir, L., Zeiske, L., Haack, H., Sullivan, L., Garton, A., and Haley, J. D. (2005) Temporal quantitation of mutant Kit tyrosine kinase signaling attenuated by a novel thiophene kinase inhibitor OSI-930. Mol. Cancer Ther. 4, 1186-1197.
27. Garton, A. J., Crew, A. P., Franklin, M., Cooke, A. R., Wynne, G. M., Castaldo, L., Kahler, J., Winski, S. L., Franks, A., Brown, E. N., Bittner, M. A., Keily, J. F., Briner, P., Hidden, C., Srebernak, M. C., Pirrit, C., O'Connor, M., Chan, A., Vulevic, B., Henninger, D., Hart, K., Sennello, R., Li, A. H., Zhang, T., Richardson, F., Emerson, D. L., Castelhano, A. L., Arnold, L. D., and Gibson, N. W. (2006) OSI-930: A novel selective inhibitor of Kit and kinase insert domain receptor tyrosine kinases with antitumor activity in mouse xenograft models. Cancer Res. 66, 1015-1024.
28. Soglia, J. R., Harriman, S. P., Zhao, S., Barberia, J., Cole, M. J., Boyd, J. G., and Contillo, L. G. (2004) The development of a higher throughput reactive intermediate screening assay incorporating microbore liquid chromatography-micro-electrospray ionization-tandem mass spectrometry and glutathione ethyl ester as an in vitro conjugating agent. J. Pharm. Biomed. Anal. 36, 105-116.
29. Correia, M. A. (2003) Hepatic cytochrome P450 degradation: mechanistic diversity of the cellular sanitation brigade. Drug Metab. Rev. 35, 107-143.
30. Evans, D. C., Watt, A. P., Nicoll-Griffith, D. A., and Baillie, T. A. (2004) Drug-protein adducts: An industry perspective on minimizing the potential for drug bioactivation in drug discovery and development. Chem. Res. Toxicol. 17, 3-16.
31. Mansuy, D. (1997) Molecular structure and hepatotoxicity: compared data about two closely related thiophene compounds. J. Hepatol. 26 (Suppl. 2), 22-25.
32. Dansette, P. M., Amar, C., Smith, C., Pons, C., and Mansuy, D. (1990) Oxidative activation of the thiophene ring by hepatic enzymes. Hydroxylation and formation of electrophilic metabolites during metabolism of tienilic acid and its isomer by rat liver microsomes. Biochem. Pharmacol. 39 (5), 911-918.
33. Bonierbale, E., Valadon, P., Pons, C., Desfosses, B., Dansette, P. M., and Mansuy, D. (1999) Opposite behaviors of reactive metabolites of tienilic acid and its isomer toward liver proteins: Use of specific anti-tienilic acid-protein adduct antibodies and the possible relationship with different hepatotoxic effects of the two compounds. Chem. Res. Toxicol. 12, 286-296.
34. Dansette, P. M., Amar, C., Valadon, P., Pons, C., Beaune, P. H., and Mansuy, D. (1991) Hydroxylation and formation of electrophilic metabolites of tienilic acid and its isomer by human liver microsomes. Catalysis by a cytochrome P450 IIC different from that responsible for mephenytoin hydroxylation. Biochem. Pharmacol. 41, 553-560.
35. Homberg, J. C., Andre, C., and Abuaf, N. (1984) A new anti-liver-kidney microsome antibody (anti-LKM2) in tienilic acid-induced hepatitis. Clin. Exp. Immunol. 55, 561-570.
36. Lopez-Garcia, M. P., Dansette, P. M., and Mansuy, D. (1994) Thiophene derivatives as new mechanism-based inhibitors of cytochromes P-450: Inactivation of yeast-expressed human liver cytochrome P-450 2C9 by tienilic acid. Biochemistry. 33, 166-175.
37. Belghazi, M., Jean, P., Poli, S., Schmitter, J.-M., Mansuy, D., and Dansette, P. M. (2001) Use of Isotopes and LC-MS-TOF for Mechanistic Studies of Tienilic Acid Metabolic Activation. In Biological Reactive Intermediates VI (Dansette, P. M. et al., Eds.) Plenum Publishers, New York.
38. Koenigs, L. L., Peter, R. M., Hunter, A. P., Haining, R. L., Rettie, A. E., Friedberg, T., Pritchard, M. P., Shou, M., Rushmore, T. H., and Trager, W. F. (1999) Electrospray ionization mass spectrometric analysis of intact cytochrome P450: Identification of tienilic acid adducts to P450 2C9. Biochemistry 38, 2312-2319.
39. Fouda, H. G., Avery, M. J., Dalvie, D., Falkner, F. C., Melvin, L. S., and Ronfeld, R. A. (1997) Disposition and metabolism of tenidap in the rat. Drug Metab. Dispos. 25, 140-148.
40. Mori, Y., Kuroda, N., Sakai, Y., Yokoya, F., Toyoshi, K., and Baba, S. (1985) Species differences in the metabolism of suprofen in laboratory animals and man. Drug Metab. Dispos. 13, 239-245.
41. Nishikawa, T., Nagata, O., Tanbo, K., Yamada, T., Takahara, Y., Kato, H., and Yamamoto, Y. (1985) Absorption, excretion and metabolism of tiquizium bromide in dogs, and relationship between pharmacological effect and plasma levels of unchanged drug. Xenobiotica 15, 1053-1060.
42. Ha-Duong, N. T., Dijols, S., Macherey, A. C., Goldstein, J. A., Dansette, P. M., and Mansuy, D. (2001) Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 40, 12112-12122.
43. Treiber, A., Dansette, P. M., and Mansuy, D. (2002) Mechanism of the aromatic hydroxylation of thiophene by acid-catalyzed peracid oxidation. J. Org. Chem. 67, 7261-7266.
44. Dansette, P. M., Bertho, G., and Mansuy, D. (2005) First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives. Biochem. Biophys. Res. Commun. 338, 450-455.
45. O'Donnell, J. P., Dalvie, D. K., Kalgutkar, A. S., and Obach, R. S. (2003) Mechanism-based inactivation of human recombinant P450 2C9 by the nonsteroidal anti-inflammatory drug suprofen. Drug Metab. Dispos. 31, 1369-1377.
46. Johnson, W. W. (2008) Many drugs and phytochemicals can be activated to biological reactive intermediates. Curr. Drug Metab. 9, 344-351.