Liquid chromatography/tandem mass spectrometry utilizing ion-molecule reactions and collision-activated dissociation for the identification of N-oxide drug metabolites

Journal of Pharmaceutical and Biomedical Analysis

Volumn 51, Issue 4, 2010, Pages 805-811

  Habicht, Steven C ^a   Duan, Penggao ^a   Vinueza, Nelson R ^a   Fu, Mingkun ^a   Kenttämaa, Hilkka I ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

Ion molecule reactions; Liquid chromatography mass spectrometry (LC MS); N oxide; Structural elucidation; Tandem mass spectrometry (MSn)

Indexed keywords

3 HYDROXYLORATADINE; BORANE DERIVATIVE; BUFFER; CLOZAPINE; CLOZAPINE N OXIDE; DRUG METABOLITE; HELIUM; LORATADINE; LORATADINE EPOXIDE; LORATADINE N OXIDE; OLANZAPINE; OLANZAPINE N OXIDE; OXIDE; TRI(DIMETHYLAMINO)BORANE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; COLLISIONALLY ACTIVATED DISSOCIATION; CONTROLLED STUDY; DERIVATIZATION; DRUG DETERMINATION; DRUG STRUCTURE; ION TRAP MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTON TRANSPORT; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

BENZODIAZEPINES; BIOTRANSFORMATION; BUFFERS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MOLECULAR STRUCTURE; OXIDES; REPRODUCIBILITY OF RESULTS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 72149117373     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2009.09.047     Document Type: Article

References (26)

1. White R.E. High-throughput screening in drug metabolism and pharmacokinetic support of drug discovery. Annu. Rev. Pharmacol. Toxicol. 40 (2000) 133-157
2. Ma S., Chowdhury S.K., and Alton K.B. Application of mass spectrometry for metabolite identification. Curr. Drug Metab. 7 (2006) 503-523
3. Prakash C., Shaffer C.L., and Nedderman A. Analytical strategies for identifying drug metabolites. Mass Spectrom. Rev. 26 (2007) 340-369
4. Ma S., and Subramanian R. Detecting and characterizing reactive metabolites by liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 41 (2006) 1121-1139
5. Kamel A., and Prakash C. High performance liquid chromatography/atmospheric pressure ionization/tandem mass spectrometry (HPLC/API/MS/MS) in drug metabolism and toxicology. Curr. Drug Metab. 7 (2006) 837-852
6. Holcapek M., Kolarova L., and Nobilis M. High-performance liquid chromatography-tandem mass spectrometry in the identification and determination of Phase I and Phase II drug metabolites. Anal. Bioanal. Chem. 391 (2008) 59-78
7. King R.S. Biotransformations in drug metabolism. In: Nassar A.F., Hollenberg P.F., and Scatina J. (Eds). Drug Metabolism Handbook: Concepts and Applications (2009), Wiley, Hoboken, NJ 17-34
8. Ramanathan R., Su A.-D., Alvarez N., Blumenkrantz N., Chowdhury S.K., Alton K.B., and Patrick J.E. Liquid chromatography/mass spectrometry methods for distinguishing n-oxides from hydroxylated compounds. Anal. Chem. 72 (2000) 1352-1359
9. Tong W., Chowdhury S.K., Chen J.-C., Zhong R., Alton K.B., and Patrick J.E. Fragmentation of N-oxides (deoxygenation) in atmospheric pressure ionization: investigation of the activation process. Rapid Commun. Mass Spectrom. 15 (2001) 2085-2090
10. Ma S., Chowdhury S.K., and Alton K.B. Thermally induced N-to-O rearrangement of tert-N-oxides in atmospheric pressure chemical ionization and atmospheric pressure photoionization mass spectrometry: differentiation of N-oxidation from hydroxylation and potential determination of N-oxidation site. Anal. Chem. 77 (2005) 3676-3682
11. Peiris D.M., Lam W., Michael S., and Ramanathan R. Distinguishing N-oxide and hydroxyl compounds: impact of heated capillary/heated ion transfer tube in inducing atmospheric pressure ionization source decompositions. J. Mass Spectrom. 39 (2004) 600-606
12. Kulanthaivel P., Barbuch R.J., Davidson R.S., Yi P., Rener G.A., Mattiuz E.L., Hadden C.E., Goodwin L.A., and Ehlhardt W.J. Selective reduction of N-oxides to amines: application to drug metabolism. Drug Metab. Dispos. 32 (2004) 966-972
13. Ohashi N., Furuuchi S., and Yoshikawa M. Usefullness of the hydrogen-deuterium exchange method in the study of drug metabolism using liquid chromatography-tandem mass spectrometry. J. Pharm. Biomed. Anal. 18 (1998) 325-334
14. Liu D.Q., Hop C.E.C.A., Beconi M.G., Mao A., and Chiu S.-H.L. Use of on-line hydrogen/deuterium exchange to facilitate metabolite identification. Rapid Commun. Mass Spectrom. 15 (2001) 1832-1839
15. Lin S.-N., Walsh S.L., Moody D.E., and Foltz R.L. Detection and time course of cocaine N-oxide and other cocaine metabolites in human plasma by liquid chromatography/tandem mass spectrometry. Anal. Chem. 75 (2003) 4335-4340
16. Duan P., Fu M., Gillespie T.A., Winger B.E., and Kenttämaa H.I. Identification of aliphatic and aromatic tertiary N-oxide functionalities in protonated analytes via ion/molecule reactions and dissociation reactions in an FT-ICR mass spectrometer. J. Org. Chem. 74 (2009) 1114-1123
17. Watkins M.A., Winger B.E., Shea R.C., and Kenttämaa H.I. Ion-molecule reactions for the characterization of polyols and polyol mixtures by ESI/FT-ICR mass spectrometry. Anal. Chem. 77 (2005) 1385-1392
18. Pyatkivskyy Y., and Ryzhov V. Coupling of ion-molecule reactions with liquid chromatography on a quadrupole ion trap mass spectrometer. Rapid Commun. Mass Spectrom. 22 (2008) 1288-1294
19. Cerrada V., Matia-Martin M.P., Novella J.L., and Alvarez-Builla J. Synthesis of 2- and 4-hydroxymethyl loratadine: usual impurities in loratadine syrup formulations. ARKIVOC 9 (2005) 200-206
20. Habicht S.C., Vinueza N.R., Archibold E.F., Duan P., and Kenttämaa H.I. Identification of the carboxylic acid functionality by using electrospray ionization and ion-molecule reactions in a modified linear quadrupole ion trap mass spectrometer. Anal. Chem. 80 (2008) 3416-3421
21. Fu M., Duan P., Li S., Habicht S.C., Pinkston D.S., Vinueza N.R., and Kenttämaa H.I. Regioselective ion-molecule reactions for the mass spectrometric differentiation of protonated isomeric aromatic diamines. Analyst 133 (2008) 452-454
22. Lopez L.L., Tiller P.R., Senko M.W., and Schwartz J.C. Automated strategies for obtaining standardized collisionally induced dissociation spectra on a benchtop ion trap mass spectrometer. Rapid Commun. Mass Spectrom. 13 (1999) 663-668
23. Schwartz J.C., Syka J.E.P., and Quarmby S.T. Improving the fundamentals of MSn on 2D linear ion traps: new ion activation and isolation techniques. Proceedings of the 53rd ASMS Conference on Mass Spectrometry and Allied Topics. San Antonio, TX (2005)
24. Cunningham Jr. C., Glish G.L., and Burinsky D.J. High amplitude short time excitation: a method to form and detect low mass product ions in a quadrupole ion trap mass spectrometer. J. Am. Soc. Mass Spectrom. 17 (2006) 81-84
25. Clozapine Tablets, in: USP31-NF26, The United States Pharmacopeial Convention, Rockville, MD, 2008, p. 1833.
26. Loratadine Tablets, in: USP31-NF26, The United States Pharmacopeial Convention, Rockville, MD, 2008, p. 2550.