Detection of covalent adducts to cytochrome P450 3A4 using liquid chromatography mass spectrometry

Chemical Research in Toxicology

Volumn 17, Issue 10, 2004, Pages 1356-1361

  Bateman, Kevin P ^a   Baker, Jennifer ^a   Wilke, Mark ^a   Lee, Justin ^a   LeRiche, Tammy ^a   Seto, Carmai ^a   Day, Stephen ^a   Chauret, Nathalie ^a   Quellet, Marc ^a   Nicoll Griffith, Deborah A ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

6',7' DIHYDROXYBERGAMOTTIN; APOPROTEIN; BERGAMOT OIL; CYTOCHROME P450 3A4; L 754394; PROTEIN; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING SITE; COVALENT BOND; DNA ADDUCT; ISOTOPE LABELING; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METHODOLOGY; PROTEIN ANALYSIS; PROTEIN BINDING; STOICHIOMETRY;

CYTOCHROME P-450 ENZYME SYSTEM; DRUG DESIGN; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; INDANS; MOLECULAR WEIGHT; NADP; PIPERAZINES; PSORALENS; TIME FACTORS;

EID: 6344265447     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx0498861     Document Type: Article

References (42)

1. Nelson, S. D. (2001) Molecular mechanisms of adverse drug reactions. Curr. Ther. Res, 62, 885-899.
2. 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.
3. Osawa, Y., and Pohl, L. R (1989) Covalent bonding of the prosthetic heme to protein: A potential mechanism for the suicide inactivation or activation of hemoproteins. Chem. Res. Toxicol. 2, 131-141.
4. Pohl, L. R., Pumford, N. R., and Martin, J. L. (1996) Mechanisms, chemical structures and drug metabolism. Eur. J. Haematol. 57 (Suppl.), 98-104.
5. Tornqvist, M., Fred, C., Haglund, J., Helleberg, H., Paulsson, B., and Rydberg, R. (2002) Protein adducts: Quantitative and qualitative aspects of their formation, analysis and applications. J. Chromatogr. B 778, 279-308.
6. Zhou, S. (2003) Separation and detection methods for covalent drug-protein adducts. J. Chromatogr. B 797, 63-90.
7. 3H-labeled 2-ethynylnaphthalene-inactivated P450 2B1 and 2B4 using amino acid sequencing and mass spectrometry. Biochemistry 33, 3766-3771.
8. Roberts, E. S., Hopkins, N. E., Zaluzec, E. J., Gage, D. A., Alworth, W. L., and Hollenberg, P. F. (1995) Mechanism-based inactivation of cytochrome P450 2B1 by 9-ethnylphenanthrene. Arch. Biochem. Biophys. 323, 295-302.
9. Chiba, M., Nishime, J. A., and Lin, J. H. (1995) Potent and selective inactivation of human liver microsomal cytochrome P-450 isoforms by L-754,394, an investigational human immune deficiency virus protease inhibitor. J. Pharmacol. Exp. Ther. 275, 1527-1534.
10. Chauret, N., Nicoll-Griffith, D., Friesen, R., Li, C., Trimble, L., Dube, D., Fortin, R., Girard, Y., and Yergey, J. (1995) Microsomal metabolism of the 5-lipoxygenase inhibitors L-746,530 and L-739,010 to reactive intermediates that covalently bind to protein: The role of the 6,8-dioxabicyclo[3.2.1]octanyl moiety. Drug Metab. Dispos. 23, 1325-1334.
11. He, K., Falick, A. M., Chen, B., Nilsson, F., and Correia, M. A. (1996) Identification of the heme adduct and an active site peptide modified during mechanism-based inactivation of rat liver cytochrome P450 2B1 by secobarbital. Chem. Res. Toxicol. 9, 614-622.
12. Zhang, K. E., Naue, J. A., Arison, B., and Vyas, K. P. (1996) Microsomal metabolism of the 5-lipoxygenase inhibitor L-739,010: Evidence for furan bioactivation. Chem. Res. Toxicol. 9, 547-554.
13. Munns, A. J., De Voss, J. J., Hooper, W. D., Dickinson, R. G., and Gillam, E. M. J. (1997) Bioactivation of phenytoin by human cytochrome P450: Characterization fo the mechanism and targets of covalent adduct formation. Chem. Res. Toxicol. 10, 1049-1058.
14. Roberts, E. S., Alworth, W. L., and Hollenberg, P. F. (1998) Mechanism-based inactivation of cytochromes P450 2E1 and 2B1 by 5-phenyl-1-pentyne. Arch. Biochem. Biophys. 354, 295-302.
15. Lin, H.-L., Kent, U. M., and Hollenberg, P. F. (2002) Mechanism-based inactivation of cytochrome P450 3A4 by 17α-ethnylestradiol: Evidence for heme destruction and covalent binding to protein. J. Pharmacol. Exp. Ther. 301, 160-167.
16. Alvarez-Diez, T. M., and Zheng, J. (2004) Mechanism-based inactivation of cytochrome P450 3A4 by 4-ipomeanol. Chem. Res. Toxicol. 17, 150-157.
17. Koenigs, L. L., and Trager, W. F. (1998) Mechanism-based inactivation of cytochrome P450 2B2 by 8-methoxypsoralen and several other furanocoumarins. Biochemistry 37, 13184-13193.
18. Regal, K. A., Schrag, M. L., Kent, U. M., Wienkers, L. C., and Hollenberg, P. F. (2000) Mechanism-based inactivation of cytochrome P450 2B1 by 7-ethynylcoumarin: Verification of apo-P450 adduction by electrospray ion trap mass spectrometry. Chem. Res. Toxicol. 13, 262-270.
19. 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. Electrospray ionization mass spectrometric analysis of intact cytochrome P450: Identification of tienilic acid adducts to P450 2C9. Biochemisty 38, 2312-2319.
20. Moreno, R. L., Goosen, T., Kent, U. M., Chung, F.-L., and Hollenberg, P. F. Differential effects of naturally occurring isothiocyanates on the activities of cytochrome P450 2E1 and the mutant P450 2E1 T303A. Arch. Biochem. Biophys. 391, 99-110.
21. Blobaum, A. L., Kent, U. M., Alworth, W. L., and Hollenberg, P. F. (2002) Mechanism-based inactivation of cytochromes P450 2E1 and 2E1 T303A by tert-butyl acetylenes: Characterization of reactive intermediate adducts to the heme and apoprotein. Chem. Res. Toxicol. 15, 1561-1571.
22. Jushchyshyn, M. I., Kent, U. M., and Hollenberg, P. F. (2003) The mechanism-based inactivation of human cytochrome P450 2B6 by phencyclidine. Drug Metab. Dispos. 31, 46-52.
23. Hutzler, J. M., Steenwyk, R. C., Smith, E. B., Walker, G. S., and Wienkers, L. C. (2004) Mechanism-based inactivation of cytochrome 450 2D6 by 1-[(2-ethyl-4-methyl-1H-imidazol-5-yl)-methyl]-4-[4-(trifluoromethyl) -2-pyridinyl]piperazine: Kinetic characterization and evidence for apoprotein adduction. Chem. Res. Toxicol. 17, 174-184.
24. Danielson, P. B. (2002) The cytochrome P450 superfamily: Biochemistry, evolution and drug metabolism in humans. Curr. Drug. Metab. 3, 561-597.
25. Nerbert, D. W., and Russell, D. W. (2002) Clinical importance of the cytochromes P450. Lancet 360, 1155-1162.
26. Lightning, L. K., Jones, J. P., Friedberg, T., Pritchard, M. P., Shou, M., Rushmore, T. H., and Trager, W. F. (2000) Mechanism-based inactivation of cytochrome P450 3A4 by L-754,394. Biochemistry 39, 4276-4287.
27. He, K., Iyer, K. R., Hayes, R. N., Sinz, M. W., Woolf, T. F., and Hollenberg, P. F. (1998) Inactivation of cytochrome P450 3A4 by bergamottin, a component of grapefruit juice. Chem. Res. Toxicol. 11, 232-259.
28. Nelson, J. R., Reider, P. J., Rossen, K., Sager, J. W., Volante, R. P., Dorsey, B. D., Hoffman, J. M., Jr., Joseph, S. A., and McDaniel, S. L. (1995) A practical synthesis of S-(chloromethyl)furo[2,3-b]-pyridine, a key intermediate for the HIV protease inhibitor, L-754,394. J. Hetercycl. Chem. 32, 1283-1287.
29. Edwards, D. J., Bellevue, F. H., III, and Woster, P. M. (1996) Identification of 6′,7′-dihydroxybergamottin, a cytochrome P450 inhibitor, in grapefruit juice. Drug Metab. Dispos. 24, 1287-1290.
30. Stresser, D. M., Turner, S. D., Blanchard, A. P., Miller, V. P., and Crespi, C. L. (2002) Cytochrome P450 fluorometric substrates: Identification of isoform-selective probes for rat CYP2D6 and human CYP3A4. Drug Metab Dispos. 30, 845-852.
31. Sahali-Sahly, Y., Balami, S. K., Lin, J. H., and Baillie, T. A. (1996) In vitro studies on the metabolic activation of the furanopyridine L-754,394, a highly potent and selective mechanism-based inhibitor of cytochrome P450 3A4. Chem. Res. Toxicol. 9, 1007-1012.
32. Bellevue, F. H., III, Woster, P. M., Edwards, D. J., He, K., and Hollenberg, P. F. (1997) Synthesis and biological evaluation of 6′,7′-dihydroxybergamottin (6,7-DHB), a naturally occurring inhibitor of cytochrome P450 3A4. Bioorg. Med. Chem. Lett. 7, 2593-2598.
33. Puntarulo, S., and Cederbaum, A. I. (1998) Production of reactive oxygen species by microsomes enriched in specific human cytochrome P450 enzymes. Free Radical Biol. Med. 24, 1324-1330.
34. Miller, L. Panvera, personal communication (now Invitrogen). Molecular weight calculated from cDNA.
35. Tarabelsi, L. BD Gentest, personal communication. Molecular weight calculated from cDNA.
36. Labbe, G., Descatiore, V., Beaune, P., Letteron, P., Larrey, D., and Passayre, D. (1989) Suicide inactivation of cytochrome P-450 by methoxsalen: Evidence for the covalent binding of a reactive intermediate to the protein moiety. J. Pharmacol. Exp. Ther. 250, 1034-1042.
37. Cai, Y., Baer-Dubowska, W., Ashwood-Smith, M. J., Ceska, O., Tachibana, S., and DiGiovanni, J. (1996) Mechanism-based inactivation of hepatic ethoxyresorufin O-dealkylation activity by naturally occurring coumarins. Chem. Res. Toxicol. 9, 729-736.
38. Hosea, N. A., Miller, G. P., and Guengerich, F. P. (2000) Elucidation of distinct ligand binding sites for cytochrome P450 3A4. Biochemistry 39, 5929-5939.
39. Schrag, M. L., and Wienkers, L. C. (2001) Covalent alteration of the CYP3A4 active site: Evidence for multiple substrate binding domains. Arch. Biochem. Biophys. 391, 49-55.
40. Dabrowski, M. J., Schrag, M. L., Wienkers, L. C., and Atkins, W. M. (2002) Pyrene-pyrene complexes at the active site of cytochrome P450 3A4: Evidence for a multiple substrate binding site. J. Am. Chem. Soc. 124, 11866-11867.
41. Yano, J. K., Wester, M. R., Schoch, G. A., Griffin, K. J., Stout, C. D., and Johnson, E. F. (2004) The structure of human microsomal cytochrome P450 3A4 determined by X-ray crystallography to 2.05 Å resolution. J. Biol. Chem. Epub ahead of print.
42. Williams, P. A., Cosme, J., Vinkovic, D. M., Ward, A., Angove, H. C., Day, P. J., Vonrhein, C., Tickle, I. J., and Jhoti, H. (2004) Crystal structures of human cytochrome P450 3A4 bound to metyrapone and progesterone. Science Epub ahead of print.