Detection and characterization of ticlopidine conjugates in rat bile using high-resolution mass spectrometry: Applications of various data acquisition and processing tools

Journal of Mass Spectrometry

Volumn 48, Issue 3, 2013, Pages 413-422

  Du, Fuying ^a   Ruan, Qian ^b   Zhu, Mingshe ^b   Xing, Jie ^a  

^a SHANDONG UNIVERSITY   (China)

^b BRISTOL MYERS SQUIBB   (United States)

Author keywords

conjugates; high resolution mass spectrometry; isotope pattern filter; mass defect filter; ticlopidine

Indexed keywords

CONJUGATES; HIGH RESOLUTION MASS SPECTROMETRY; ISOTOPE PATTERN; MASS DEFECT; TICLOPIDINE;

AMINO ACIDS; BIOMOLECULES; BODY FLUIDS; CHARACTERIZATION; CHROMATOGRAPHIC ANALYSIS; DATA ACQUISITION; DEFECTS; DISSOCIATION; ELECTRONIC DOCUMENT EXCHANGE; ISOTOPES; MASS SPECTROMETRY; METABOLISM; METABOLITES; PHYSIOLOGY; RATS;

PYRIDINE;

ACETYLCYSTEINE; CYSTEINE; CYSTEINYLGLYCINE; GLUCURONIDE; GLUTATHIONE; ISOTOPE; TICLOPIDINE;

ANIMAL TISSUE; ARTICLE; ATOM; BILE; COLLISIONALLY ACTIVATED DISSOCIATION; COMPARATIVE STUDY; CONJUGATE; DRUG METABOLISM; DRUG SCREENING; DRUG STRUCTURE; FILTER; IN VITRO STUDY; INFORMATION PROCESSING; ION PAIR CHROMATOGRAPHY; LIQUID CHROMATOGRAPHY; MALE; MASS SPECTROMETRY; METABOLIC ACTIVATION; NONHUMAN; PRIORITY JOURNAL; RAT; STRUCTURE ANALYSIS;

ANIMALS; BILE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MALE; PLATELET AGGREGATION INHIBITORS; RATS; RATS, WISTAR; TANDEM MASS SPECTROMETRY; TICLOPIDINE;

EID: 84875147820     PISSN: 10765174     EISSN: 10969888     Source Type: Journal    
DOI: 10.1002/jms.3170     Document Type: Article

References (23)

1. A. K. Jacobson,. Platelet ADP receptor antagonists: ticlopidine and clopidogrel. Best Pract. Res. Clin. Haematol. 2004, 17, 55.
2. T. R. Whetsel, D. M. Bell,. Rash in patients receiving ticlopidine after intracoronary stent placement. Pharmacotherapy 1999, 19, 228.
3. S. Noble, K. L. Goa,. Ticlopidine. A review of its pharmacology, clinical efficacy and tolerability in the prevention of cerebral ischaemia and stroke. Drugs Aging 1996, 8, 214.
4. Q. Ruan, M. S. Zhu,. Investigation of bioactivation of ticlopidine using linear ion trap/orbitrap mass spectrometry and an improved mass defect filtering technique. Chem. Res. Toxicol. 2010, 23, 909.
5. J. J. Bruno, B. A. Molony,. In New Drugs Annual: Cardiovascular Drugs, (Ed:, A. Scriabine,), Raven: New York, 1983, 295-316.
6. D. K. Dalvie, T. N. O'Connell,. Characterization of novel dihydrothienopyridinium and thienopyridinium metabolites of ticlopidine in vitro: role of peroxidases, cytochromes p450, and monoamine oxidases. Drug Metab. Dispos. 2004, 32, 49.
7. S. Shimizu, R. Atsumi, T. Nakazawa, Y. Fujimaki, K. Sudo, O. Okazaki,. Metabolism of ticlopidine in rats: identification of the main biliary metabolite as a glutathione conjugate of ticlopidine S-oxide. Drug Metab. Dispos. 2009, 37, 1904.
8. P. Valadon, P. M. Dansette, J. P. Girault, C. Amar, D. Mansuy,. 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. 1996, 9, 1403.
9. P. M. Dansette, G. Bertho, D. Mansuy,. First evidence that cytochrome P450 may catalyze both S-oxidation and epoxidation of thiophene derivatives. Biochem. Biophys. Res. Commun. 2005, 338, 450.
10. N.-T. Ha-Duong, S. Dijols, A.-C. Macherey, J. A. Goldstein, P. M. Dansette, D. Mansuy,. Ticlopidine as a selective mechanism-based inhibitor of human cytochrome P450 2C19. Biochemistry 2001, 40, 12112.
11. A. Garg, B. Prasad, H. Takwani, M. Jain, R. Jain, S. Singh,. Evidence of the formation of direct covalent adducts of primaquine, 2-tert-butylprimaquine (NP-96) and monohydroxy metabolite of NP-96 with glutathione and N-acetylcysteine. J. Chromatogr. B 2011, 879, 1.
12. M. Giorgi, G. Mengozzi, A. Raffaelli, A. Saba,. Characterization of in vivo plasma metabolites of tepoxalin in horses using LC-MS-MS. J. Pharm. Biomed. Anal. 2011, 56, 45.
13. F. Y. Du, T. Liu, T. Liu, Y. M. Wang, Y. K. Wan, J. Xing,. Metabolite identification of triptolide by data-dependent accurate mass spectrometric analysis in combination with online H/D exchange and multiple data mining techniques. Rapid Commun. Mass Spectrom. 2011, 25, 3167.
14. H.-K. Lim, J. Chen, K. Cook, C. Sensenhauser, J. Silva, D. C. Evans,. A generic method to detect electrophilic intermediates using isotopic pattern triggered data-dependent high-resolution accurate mass spectrometry. Rapid Commum. Mass. Spectrom. 2008, 22, 1295.
15. H. Y. Zhang, D. L. Zhang, K. Ray, M. S. Zhu,. Mass defect filter technique and its applications to drug metabolite identification by high-resolution mass spectrometry. J. Mass Spectrom. 2009, 44, 999.
16. Y. Liang, G. J. Wang, L. Xie, L. S. Sheng,. Recent development in liquid chromatography/mass spectrometry and emerging technologies for metabolite identification. Curr. Drug Metab. 2011, 12, 329.
17. L. Ma, B. Wen, Q. Ruan, M. S. Zhu,. Rapid screening of glutathione-trapped reactive metabolites by linear ion trap mass spectrometry with isotope pattern-dependent scanning and postacquisition data mining. Chem. Res. Toxicol. 2008, 21, 1477.
18. F. Cuyckens, R. Hurkmans, J. M. Castro-Perez, L. Leclecq, R. J. Mortishire-Smith,. Extracting metabolite ions out of a matrix background by combined mass defect, neutral loss and isotope filtration. Rapid Commun. Mass Spectrom. 2009, 23, 327.
19. K. Yoneda, R. Iwamura, H. Kishi, Y. Mizukami, K. Mogami, S. Kobayashi,. Identification of the active metabolite of ticlopidine from rat in vitro metabolites. Br. J. Pharmacol. 2004, 142, 551.
20. N. A. Farid, A. Kurihara, S. A. Wrighton,. Metabolism and disposition of the thienopyridine antiplatelet drugs ticlopidine, clopidogrel, and prasugrel in humans. J. Clin. Pharmacol. 2010, 50, 126.
21. T. Rousu, O. Pelkonen, A. Tolonen,. Rapid detection and characterization of reactive drug metabolites in vitro using several isotope-labeled trapping agents and ultra-performance liquid chromatography/time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2009, 23, 843.
22. J. C. Talakad, M. B. Shah, G. S. Walker, C. Xiang, J. R. Halpert, D. Dalvie,. Comparison of in vitro metabolism of ticlopidine by human cytochrome P450 2B6 and rabbit cytochrome P450 2B4. Drug Metab. Dispos. 2011, 39, 539.
23. B. Wen, L. Ma, S. D. Nelson, M. S. Zhu,. High-throughput screening and characterization of reactive metabolites using polarity switching of hybrid triple quadrupole linear ion trap mass spectrometry. Anal. Chem. 2008, 80, 1788.