In-source formation of N-acetyl-p-benzoquinone imine (NAPQI), the putatively toxic acetaminophen (paracetamol) metabolite, after derivatization with pentafluorobenzyl bromide and GC-ECNICI-MS analysis

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences

Volumn 879, Issue 17-18, 2011, Pages 1476-1484

  Tsikas, Dimitrios ^a   Trettin, Arne ^a   Zörner, Alexander A ^a   Gutzki, Frank Mathias ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

Author keywords

Cytochrome P450; Derivatization; Electron capture negative ion chemical ionization; Electrospray ionization; Pentafluorobenzyl bromide

Indexed keywords

CYTOCHROME P450; DERIVATIZATIONS; ELECTRON-CAPTURE; ELECTROSPRAYS; PENTAFLUOROBENZYL BROMIDE;

ACETONITRILE; BROMINE; BROMINE COMPOUNDS; ELECTRONS; ETHERS; IONIZATION OF GASES; MASS SPECTROMETRY; METABOLISM; METABOLITES; METHANE; NEGATIVE IONS; NITROGEN COMPOUNDS; REACTION INTERMEDIATES; TOXIC MATERIALS;

ELECTROSPRAY IONIZATION;

ACETONITRILE; ANION; BENZYL BROMIDE; DRUG METABOLITE; ETHER DERIVATIVE; METHANE; N ACETYL 1,4 BENZOQUINONE IMINE; PARACETAMOL;

ARTICLE; DERIVATIZATION; ELECTRON CAPTURE DETECTION; ELECTROSPRAY; FLOW INJECTION ANALYSIS; GAS CHROMATOGRAPHY; HUMAN; ION MONITORING; MASS FRAGMENTOGRAPHY; PLASMA; PRIORITY JOURNAL; SENSITIVITY AND SPECIFICITY; TEMPERATURE; URINE;

ACETAMINOPHEN; ACETONITRILES; ANALGESICS, NON-NARCOTIC; BENZOQUINONES; FLUOROBENZENES; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; IMINES; METHANE;

EID: 79955608505     PISSN: 15700232     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jchromb.2011.01.025     Document Type: Article

References (28)

1. James L.P., Mayeux P.R., Hinson J.A. Drug Metab. Dispos. 2003, 31:1499.
2. Sun J., Schnackenberg L.K., Holland R.D., Schmitt T.C., Cantor G.H., Dragan Y.P., Beger R.D. J. Chromatogr. B 2008, 871:328.
3. Testa B., Krämer S.D. Chem. Biodivers. 2007, 4:257.
4. Calder I.C., Creek M.J., Williams P.J. J. Med. Chem. 1973, 16:499.
5. Miner D.J., Kissinger P.T. Biochem. Biopharmacol. 1979, 28:3285.
6. Blair I.A., Boobis A.R., Davies D.S. Tetrahedron Lett. 1980, 21:4947.
7. Dahlin D.C., Nelson S.D. J. Med. Chem. 1982, 25:885.
8. Lohmann W., Karst U. Anal. Bioanal. Chem. 2006, 386:1701.
9. Tsikas D. J. Chromatogr. B 1998, 717:201.
10. Tsikas D., Tewes K.S., Gutzki F.M., Schwedhelm E., Greipel J., Frölich J.C. J. Chromatogr. B 1998, 709:79.
11. Tsikas D. Anal. Chem. 2000, 72:4064.
12. Schwedhelm E., Tsikas D., Gutzki F.M., Frölich J.C. Anal. Biochem. 1999, 276:195.
13. Lakshmi V.M., Hsu F.F., Davis B.B., Zenser T.V. Chem. Res. Toxicol. 2000, 13:891.
14. Tsikas D., Schwedhelm E., Frölich J.C. J. Chromatogr. A 2005, 1067:337.
15. Grifoll M., Solanas A.M., Bayona J.M. Contam. Toxicol. 1990, 19:175.
16. van der Heeft E., de Jong A.P.J.M., van Ginkel L.A., van Rossum H.J., Zomer G. Biol. Mass Spectrom. 1991, 20:763.
17. Gutzki F.M., Tsikas D., Adelheid U., Frölich J.C. Biol. Mass Spectrom. 1992, 21:97.
18. Shen J., Xia X., Jiang H., Li C., Li J., Li X., Ding S. J. Chromatogr. B 2009, 877:1523.
19. Bader M., Rosenberger W., Gutzki F.M., Tsikas D. J. Chromatogr. B 2009, 877:1402.
20. Dawson J.H.J., Nibbering N.M.M. Int. J. Mass Spectrom. Ion Phys. 1980, 33:3-19.
21. Ingemann S., Nibbering N.M.M., Sullivan S.A., DePuy C.H. J. Am. Chem. Soc. 1982, 104:6520.
22. Büker H.H., Nibbering N.M.M., Espinosa D., Mongin F., Schlosser M. Tetrahedron Lett. 1997, 38:8519.
23. Langer W.D., Velusamy T., Kuiper T.B., Peng R., McCarthy M.C., Travers M.J., Kovacs A., Gottlieb C.A., Thaddeus P. Astrophys. J. 1997, 480:L63.
24. Zhu Y., Silverman R.B. Biochemistry 2008, 47:2231.
25. Shin N.Y., Liu Q., Stamer S.L., Liebler D.C. Chem. Res. Toxicol. 2007, 20:859.
26. Kalgutkar A.S., Vaz A.D.N., Lame M.E., Henne K.R., Soglia J., Zhao S.X., Abramaov Y.A., Lombardo F., Collin C., Hendsch Z.S., Hop C.E.C.A. Drug Metab. Dispos. 2005, 33:243.
27. McConkey S.E., Grant D.M., Cribb A.E. J. Vet. Pharmacol. Ther. 2009, 32:585.
28. Nakamura S., Takino M., Daihima S. Analyst 2001, 126:835.