Assessment of the metabolism and intrinsic reactivity of a novel catechol metabolite

Chemical Research in Toxicology

Volumn 21, Issue 5, 2008, Pages 1125-1133

  Hutzler, J Matthew ^a   Melton, Roger J ^a   Rumsey, Jeanne M ^a   Thompson, David C ^a   Rock, Dan A ^a,b   Wienkers, Larry C ^a,b  

^a PFIZER INC   (United States)

^b AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BENZODIOXOLE DERIVATIVE; 2 QUINONE; CATECHOL; CELL PROTEIN; CYTOCHROME P450 3A4; GLUTATHIONE; IMIDAZOLE DERIVATIVE; MONOPHENOL MONOOXYGENASE; PH 302; QUINONE DERIVATIVE; CATECHOL DERIVATIVE;

ANIMAL CELL; ARTICLE; CONCENTRATION RESPONSE; COVALENT BOND; CYTOTOXICITY; DEMETHYLATION; ELECTROPHILIC STRESS; GLUCURONIDATION; HUMAN; HUMAN CELL; LIQUID CHROMATOGRAPHY; LIVER CELL; LIVER MICROSOME; MASS SPECTROMETRY; METABOLITE; METHYLATION; NONHUMAN; OXIDATION; OXIDATION REDUCTION REACTION; RAT; SULFATION; ANIMAL; CELL CULTURE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; METABOLISM;

RATTUS;

ANIMALS; CATECHOLS; CELLS, CULTURED; GLUTATHIONE; HEPATOCYTES; HUMANS; MICROSOMES, LIVER; MOLECULAR STRUCTURE; MONOPHENOL MONOOXYGENASE; RATS;

EID: 47549098315     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700429v     Document Type: Article

References (39)

1. Salerno, L., Sorrenti, V., Di Giacomo, C., Romeo, G., and Siracusa, M. A. (2002) Progress in the development of selective nitric oxide synthase (NOS) inhibitors. Curr. Pharm. Des. 8, 177-200.
2. Blasko, E., Glaser, C. B., Devlin, J. J., Xia, W., Feldman, R. I., Polokoff, M. A., Phillips, G. B., Whitlow, M., Auld, D. S., McMillan, K., Ghosh, S., Stuehr, D. J., and Parkinson, J. F. (2002) Mechanistic studies with potent and selective inducible nitric oxide synthase dimerization inhibitors. J. Biol. Chem. 277, 295-302.
3. Hutzler, J. M., Melton, R. J., Rumsey, J. M., Schnute, M. E., Locuson, C. W., and Wienkers, L. C. (2006) Inhibition of cytochrome P450 3A4 by a pyrimidineimidazole: Evidence for complex heme interactions. Chem. Res. Toxicol. 19, 1650-1659.
4. O'Brien, P. J. (1991) Molecular mechanisms of quinone cytotoxicity. Chem.-Biol. Interact. 80, 1-41.
5. Bolton, J. L., Trush, M. A., Penning, T. M., Dryhurst, G., and Monks, T. J. (2000) Role of quinones in toxicology. Chem. Res. Toxicol. 13, 135-160.
6. Cavalieri, E. L., Li, K. M., Balu, N., Saeed, M., Devanesan, P., Higginbotham, S., Zhao, J., Gross, M. L., and Rogan, E. G. (2002) Catechol ortho-quinones: The electrophilic compounds that form depurinating DNA adducts and could initiate cancer and other diseases. Carcinogenesis 23, 1071-1077.
7. Liu, X., Pisha, E., Tonetti, D. A., Yao, D., Li, Y., Yao, J., Burdette, J. E., and Bolton, J. L. (2003) Antiestrogenic and DNA damaging effects induced by tamoxifen and toremifene metabolites. Chem. Res. Toxicol. 16, 832-837.
8. Bolton, J. L., Pisha, E., Zhang, F., and Qiu, S. (1998) Role of quinoids in estrogen carcinogenesis. Chem. Res. Toxicol. 11, 1113-1127.
9. Bolton, J. L., and Chang, M. (2001) Quinoids as reactive intermediates in estrogen carcinogenesis. Adv. Exp. Med. Biol. 500, 497-507.
10. Moridani, M. Y., Scobie, H., Salehi, P., and O'Brien, P. J. (2001) Catechin metabolism: Glutathione conjugate formation catalyzed by tyrosinase, peroxidase, and cytochrome P450. Chem. Res. Toxicol. 14, 841-848.
11. Carvalho, M., Remiao, F., Milhazes, N., Borges, F., Fernandes, E., Monteiro Mdo, C., Goncalves, M. J., Seabra, V., Amado, F., Carvalho, F., and Bastos, M. L. (2004) Metabolism is required for the expression of ecstasy-induced cardiotoxicity in vitro. Chem. Res. Toxicol. 17, 623-632.
12. 3H]dopamine: Impact of ascorbic acid and glutathione. J. Neurochem. 63, 1126-1132.
13. McMillan, K., Adler, M., Auld, D. S., Baldwin, J. J., Blasko, E., Browne, L. J., Chelsky, D., Davey, D., Dolle, R. E., Eagen, K. A., Erickson, S., Feldman, R. I., Glaser, C. B., Mallari, C., Morrissey, M. M., Ohlmeyer, M. H., Pan, G., Parkinson, J. F., Phillips, G. B., Polokoff, M. A., Sigal, N. H., Vergona, R., Whitlow, M., Young, T. A., and Devlin, J. J. (2000) Allosteric inhibitors of inducible nitric oxide synthase dimerization discovered via combinatorial chemistry. Proc. Natl. Acad. Sci. U.S.A. 97, 1506-1511.
14. Chen, Q., Ngui, J. S., Doss, G. A., Wang, R. W., Cai, X., DiNinno, F. P., Blizzard, T. A., Hammond, M. L., Stearns, R. A., Evans, D. C., Baillie, T. A., and Tang, W. (2002) Cytochrome P450 3A4-mediated bioactivation of raloxifene: Irreversible enzyme inhibition and thiol adduct formation. Chem. Res. Toxicol. 15, 907-914.
15. Bolton, J. L., Acay, N. M., and Vukomanovic, V. (1994) Evidence that 4-allyl-o-quinones spontaneously rearrange to their more electrophilic quinone methides: Potential bioactivation mechanism for the hepatocarcinogen safrole. Chem. Res. Toxicol. 7, 443-450.
16. Sugumaran, M., and Bolton, J. (1995) Direct evidence for quinone-quinone methide tautomerism during tyrosinase catalyzed oxidation of 4-allylcatechol. Biochem. Biophys. Res. Commun. 213, 469-474.
17. Tang, W., Stearns, R. A., Wang, R. W., Chiu, S. H., and Baillie, T. A. (1999) Roles of human hepatic cytochrome P450s 2C9 and 3A4 in the metabolic activation of diclofenac. Chem. Res. Toxicol. 12, 192-199.
18. 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.
19. Murray, M. (2000) Mechanisms of inhibitory and regulatory effects of methylenedioxyphenyl compounds on cytochrome P450-dependent drug oxidation. Curr. Drug Metab. 1, 67-84.
20. Beaumont, K. C., Causey, A. G., Coates, P. E., and Smith, D. A. (1996) Pharmacokinetics and metabolism of zamifenacin in mouse, rat, dog and man. Xenobiotica 26, 459-471.
21. Kumagai, Y., Wickham, K. A., Schmitz, D. A., and Cho, A. K. (1991) Metabolism of methylenedioxyphenyl compounds by rabbit liver preparations. Participation of different cytochrome P450 isozymes in the demethylenation reaction. Biochem. Pharmacol. 42, 1061-1067.
22. Zhang, F., Chen, Y., Pisha, E., Shen, L., Xiong, Y., van Breemen, R. B., and Bolton, J. L. (1999) The major metabolite of equilin, 4-hydroxyequilin, autoxidizes to an o-quinone which isomerizes to the potent cytotoxin 4-hydroxyequilenin-o-quinone. Chem. Res. Toxicol. 12, 204-213.
23. Zhang, F., Yao, D., Hua, Y., van Breemen, R. B., and Bolton, J. L. (2001) Synthesis and reactivity of the catechol metabolites from the equine estrogen, 8,9-dehydroestrone. Chem. Res. Toxicol. 14, 754-763.
24. Zhang, F., Fan, P. W., Liu, X., Shen, L., van Breeman, R. B., and Bolton, J. L. (2000) Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-Dihydroxytamoxifen-o-quinone. Chem. Res. Toxicol. 13, 53-62.
25. Monks, T. J., Bai, F., Miller, R. T., and Lau, S. S. (2001) Serotonergic neurotoxicity of methylenedioxyamphetamine and methylenedioxymetamphetamine. Adv. Exp. Med. Biol. 500, 397-406.
26. Carvalho, M., Milhazes, N., Remiao, F., Borges, F., Fernandes, E., Amado, F., Monks, T. J., Carvalho, F., and Bastos, M. L. (2004) Hepatotoxicity of 3,4-methylenedioxyamphetamine and α-methyldopamine in isolated rat hepatocytes: Formation of glutathione conjugates. Arch. Toxicol. 78, 16-24.
27. Carvalho, M., Hawksworth, G., Milhazes, N., Borges, F., Monks, T. J., Fernandes, E., Carvalho, F., and Bastos, M. L. (2002) Role of metabolites in MDMA (ecstasy)-induced nephrotoxicity: An in vitro study using rat and human renal proximal tubular cells. Arch. Toxicol. 76, 581-588.
28. 3H]paroxetine to human liver microsomes and S-9 fractions: Identification of an electrophilic quinone metabolite of paroxetine. Chem. Res. Toxicol. 20, 1649-1657.
29. Tang, W., Stearns, R. A., Bandiera, S. M., Zhang, Y., Raab, C., Braun, M. P., Dean, D. C., Pang, J., Leung, K. H., Doss, G. A., Strauss, J. R., Kwei, G. Y., Rushmore, T. H., Chiu, S. H., and Baillie, T. A. (1999) Studies on cytochrome P-450-mediated bioactivation of diclofenac in rats and in human hepatocytes: Identification of glutathione conjugated metabolites. Drug Metab. Dispos. 27, 365-372.
30. Thompson, D. C., Constantin-Teodosiu, D., and Moldeus, P. (1991) Metabolism and cytotoxicity of eugenol in isolated rat hepatocytes. Chem.-Biol. Interact. 77, 137-147.
31. Antonio, L., Xu, J., Little, J. M., Burchell, B., Magdalou, J., and Radominska-Pandya, A. (2003) Glucuronidation of catechols by human hepatic, gastric, and intestinal microsomal UDP-glucuronosyltransferases (UGT) and recombinant UGT1A6, UGT1A9, and UGT2B7. Arch. Biochem. Biophys. 411, 251-261.
32. Loureiro, A. I., Bonifacio, M. J., Fernandes-Lopes, C., Almeida, L., Wright, L. C., and Soares-Da-Silva, P. (2006) Human metabolism of nebicapone (BIA 3-202), a novel catechol-o-methyltransferase inhibitor: Characterization of in vitro glucuronidation. Drug Metab. Dispos. 34, 1856-1862.
33. Sadeghi-Aliabadi, H., Chan, K., Lehmler, H. J., Robertson, L. W., and O'Brien, P. J. (2007) Molecular cytotoxic mechanisms of catecholic polychlorinated biphenyl metabolites in isolated rat hepatocytes. Chem.-Biol. Interact. 167, 184-192.
34. Moridani, M. Y., Siraki, A., Chevaldina, T., Scobie, H., and O'Brien, P. J. (2004) Quantitative structure toxicity relationships for catechols in isolated rat hepatocytes. Chem.-Biol. Interact. 147, 297-307.
35. Yao, D., Zhang, F., Yu, L., Yang, Y., van Breemen, R. B., and Bolton, J. L. (2001) Synthesis and reactivity of potential toxic metabolites of tamoxifen analogues: Droloxifene and toremifene o-quinones. Chem. Res. Toxicol. 14, 1643-1653.
36. Chiba, M., Jin, L., Neway, W., Vacca, J. P., Tata, J. R., Chapman, K., and Lin, J. H. (2001) P450 interaction with HIV protease inhibitors: Relationship between metabolic stability, inhibitory potency, and P450 binding spectra. Drug Metab. Dispos. 29, 1-3.
37. Naish, S., Holden, J. L., Cooksey, C. J., and Riley, P. A. (1988) Major primary cytotoxic product of 4-hydroxyanisole oxidation by mushroom tyrosinase is 4-methoxy ortho-benzoquinone. Pigm. Cell Res. 1, 382-385.
38. Samuel, K., Yin, W., Stearns, R. A., Tang, Y. S., Chaudhary, A. G., Jewell, J. P., Lanza, T., Jr., Lin, L. S., Hagmann, W. K., Evans, D. C., and Kumar, S. (2003) Addressing the metabolic activation potential of new leads in drug discovery: A case study using ion trap mass spectrometry and tritium labeling techniques. J. Mass Spectrom. 38, 211-221.
39. Sanchez-Ferrer, A., Rodriguez-Lopez, J. N., Garcia-Canovas, F., and Garcia-Carmona, F. (1995) Tyrosinase: A comprehensive review of its mechanism. Biochim. Biophys. Acta 1247, 1-11.