Study of the fragmentation mechanism of protonated 6-hydroxychlorzoxazone: Application in simultaneous analysis of CYP2E1 activity with major human cytochrome P450s

Analytical Chemistry

Volumn 75, Issue 3, 2003, Pages 469-478

  Anari, M Reza ^a   Bakhtiar, Ray ^a   Franklin, Ronald B ^a   Pearson, Paul G ^a   Baillie, Thomas A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE IONIZATION (API);

ATMOSPHERIC PRESSURE; IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES;

ORGANIC COMPOUNDS;

6 HYDROXYCHLORZOXAZONE; CHLORZOXAZONE; CYTOCHROME P450 2E1; DEUTERIUM; RESERPINE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; ATMOSPHERIC PRESSURE; CHEMICAL COMPOSITION; DISSOCIATION CONSTANT; ENZYME ACTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ION EXCHANGE; LIQUID CHROMATOGRAPHY; PH; PROTON TRANSPORT; QUALITY CONTROL; TANDEM MASS SPECTROMETRY;

CHLORZOXAZONE; CHROMATOGRAPHY, LIQUID; CYTOCHROME P-450 CYP2E1; CYTOCHROME P-450 ENZYME SYSTEM; HUMANS; MASS SPECTROMETRY; PEPTIDE FRAGMENTS; REPRODUCIBILITY OF RESULTS;

EID: 0037316961     PISSN: 00032700     EISSN: None     Source Type: Journal    
DOI: 10.1021/ac026157m     Document Type: Article

References (46)

1. Ding, X. X.; Koop, D. R.; Crump, B. L.; Coon, M. J. Mol. Pharmacol. 1986, 30, 370-378.
2. de Waziers, I.; Cugnenc, P. H.; Yang, C. S.; Leroux, J. P.; Beaune, P. H. J. Pharmacol. Exp. Ther. 1990, 253, 387-394.
3. Guengerich, F. P.; Kim, D. H.; Iwasaki, M. Chem. Res. Toxicol. 1991, 4, 168-179.
4. Guengerich, F. P.; Turvy, C. G. J. Pharmacol. Exp. Ther. 1991, 256, 1189-1194.
5. Porter, T. D.; Khani, S. C.; Coon, M. J. Mol. Pharmacol. 1989, 36, 61-65.
6. Kim, R. B.; O'Shea, D. Clin. Pharmacol. Ther. 1995, 57, 645-655.
7. Coon, M. J.; Koop, D. R. Arch. Toxicol. 1987, 60, 16-21.
8. Funae, Y.; Imaoka, S.; Shimojo, N. Biochem. Int. 1988, 16, 503-509.
9. Salazar, D. E.; Sorge, C. L.; Corcoran, G. B. Biochem. Biophys. Res. Commun. 1988, 157, 315-320.
10. Tindberg. N.; Ingelman-Sundberg, M. Biochemistry 1989, 28, 4499-4504.
11. Morimoto, M.; Hagbjork, A. L.; Nanji, A. A.; Ingelman-Sundberg, M.; Lindros. K. O.; Fu. P. C.; Albano. E.; French, S. W. Alcohol 1993, 10, 459-464.
12. O'Shea, D.; Davis, S. N.; Kim, R. B.; Wilkinson, G. R. Clin. Pharmacol. Ther. 1994, 56, 359-367.
13. Zand, R.; Nelson, S. D.; Slattery, J. T.; Thummel, K. E.; Kalhorn, T. F.; Adams, S. P.; Wright, J. M. Clin. Pharmacol. Ther. 1993, 54, 142-149.
14. Kharasch, E. D.; Thummel, K. E. Anesthesiology 1993, 79, 795-807.
15. Garton, K. J.; Yuen, P.; Meinwald, J.; Thummel, K. E.; Kharasch, E. D. Drug Metab. Dispos. 1995, 23, 1426-1430.
16. Peter, R.; Bocker, R.; Beaune, P. H.; Iwasaki, M.; Guengerich, F. P.; Yang, C. S. Chem. Res. Toxicol. 1990, 3, 566-573.
17. Mishin, V. M.; Rosman, A. S.; Basu, P.; Kessova, I.; Oneta, C. M.; Lieber, C. S. Am. J. Gastroenterol. 1998, 93, 2154-2161.
18. Lucas, D.; Menez, J. F.; Berthou, F. Methods Enzymol. 1996, 272, 115-123.
19. Dreisbach, A. W.; Ferencz, N.; Hopkins, N. E.; Fuentes, M. G.; Rege, A. B.; George, W. J.; Lertora, J. J. Clin. Pharmacol. Ther. 1995, 58, 498-505.
20. Bachmann, K.; Sarver, J. G. Pharmacology 1996, 52, 169-177.
21. Rodrigues, A. D.; Lin, J. H. Curr. Opin. Chem. Biol. 2001, 5, 396-401.
22. Davit, B.; Reynolds, K.; Yuan, R.; Ajayi, F.; Conner, D.; Fadiran, E.; Gillespie, B.; Sahajwalla, C.; Huang, S. M.; Lesko, L. J. J. Clin. Pharmacol. 1999, 39, 899-910.
23. Lucas, D.; Berthou, F.; Girre, C.; Poitrenaud, F.; Menez, J. F. J. Chromatogr. 1993, 622, 79-86.
24. Frye, R. F.; Stiff, D. D. J. Chromatogr., B 1996, 686, 291-296.
25. Draper, A. J.; Madan, A.; Latham, J.; Parkinson, A. Drug Metab. Dispos. 1998, 26, 305-312.
26. Tanaka, E. J. Pharm. Biomed. Anal. 1998, 16, 899-904.
27. Weaver, R. J. Xenobiotica 2001, 31, 499-538.
28. Miller, V. P.; Stresser, D. M.; Blanchard, A. P.; Turner, S.; Crespi, C. L. Ann, N. Y. Acad. Sci. 2000, 919, 26-32.
29. Crespi, C. L. Pharm. Sci. Technol. Today 1999, 2, 119-120.
30. Ayrton, J.; Plumb, R.; Leavens, W. J.; Mallett, D.; Dickins, M.; Dear, G. J. Rapid Commun. Mass Spectrom. 1998, 12, 217-224.
31. Scott, R. J.; Palmer, J.; Lewis, I. A.; Pleasance, S. Rapid Commun. Mass Spectrom. 1999, 13, 2305-2319.
32. Bu, H. Z.; Magis, L.; Knuth, K.; Teitelbaum, P. Rapid Commun. Mass Spectrom. 2000, 14, 1619-1624.
33. Kronbach, T.; Mathys, D.; Umeno, M.; Gonzalez, F. J.; Meyer, U. A. Mol. Pharmacol. 1989, 36, 89-96.
34. Gut, J.; Gasser, R.; Dayer, P.; Kronbach, T.; Catin, T.; Meyer, U. A. FEBS Lett. 1984, 173, 287-290.
35. Goldstein, J. A.; Faletto, M. B.; Romkes-Sparks, M.; Sullivan, T.; Kitareewan, S.; Raucy, J. L.; Lasker, J. M.; Ghanayem, B. I. Biochemistry 1994, 33, 1743-1752.
36. Leemann, T.; Transom, C.; Dayer, P. Life Sci. 1993, 52, 29-34.
37. Rahman, A.; Korzekwa, K. R.; Grogan, J.; Gonzalez, F. J.; Harris, J. W. Cancer Res. 1994, 54, 5543-5546.
38. Kawashima, H.; Kusunose, E.; Kikuta, Y.; Kinoshita, H.; Tanaka, S.; Yamamoto, S.; Kishimoto, T.; Kusunose, M. J. Biochem. (Tokyo) 1994, 116, 74-80.
39. Distlerath, L. M.; Reilly, P. E.; Martin, M. V.; Davis, G. G.; Wilkinson, G. R.; Guengerich, F. P. J Biol. Chem. 1985, 260, 9057-9067.
40. McLafferty, F. W., Turecek, F., Eds. Interpretation of mass spectra, 4th ed.; University Science Books: Sausalito, CA, 1993.
41. Cerny, R. L.; Tomer, K. B.; Gross, M., L.; Grotjahn, L. Anal. Biochem. 1987, 15, 175-182.
42. McLafferty, F. W., Turecek, F., Eds. Interpretation of mass spectra, 4th ed.; University Science Books: Sausalito, CA, 1993; pp 348-350.
43. Beynon, J. H. Mass Spectrometry and Its Applications to Organic Chemistry; Elsevier Science: Amsterdam, 1960.
44. Wszolek, P.; McLafferty, F. W.; Brewster, J. H. Org. Mass Spectrom. 1968, 1, 127.
45. Wilkinson, G. R. In Drugs and Pharmaceutical Sciences: Drug-Drug Interactions; Rodrigues, A. D., Ed.; Marcel Dekker: New York, 2002; Vol. 116, pp 439-504.
46. Fairbrother, K. S.; Grove, J.; de Waziers, I.; Steimel, D. T.; Day, C. P.; Crespi, C. L.; Daly, A. K. Pharmacogenetics 1998, 8, 543-552.