Investigational study of tamoxifen phase I metabolites using chromatographic and spectroscopic analytical techniques

Journal of Pharmaceutical and Biomedical Analysis

Volumn 55, Issue 3, 2011, Pages 518-526

  Teunissen, S F ^a   Rosing, H ^a   Seoane, M Dominguez ^b   Brunsveld, L ^b,c   Schellens, J H M ^a,d   Schinkel, A H ^a   Beijnen, J H ^a,d  

^a NETHERLANDS CANCER INSTITUTE   (Netherlands)

^b CHEMICAL GENOMICS CENTRE OF THE MAX PLANCK SOCIETY   (Germany)

^c EINDHOVEN UNIVERSITY OF TECHNOLOGY   (Netherlands)

^d UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Fragmentation; Identification; Liquid chromatography; Mass spectrometry; Metabolites; Tamoxifen; UV absorption

Indexed keywords

3',4'DIHYDROXYTAMOXIFEN; TAMOXIFEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CHEMICAL STRUCTURE; CLINICAL ARTICLE; DRUG SYNTHESIS; HUMAN; ION TRAP MASS SPECTROMETRY; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; QUALITATIVE ANALYSIS; TANDEM MASS SPECTROMETRY; ULTRAVIOLET SPECTROSCOPY;

ANTINEOPLASTIC AGENTS, HORMONAL; BREAST NEOPLASMS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FEMALE; HUMANS; METABOLIC DETOXICATION, PHASE I; MOLECULAR STRUCTURE; QUINONES; TAMOXIFEN; TANDEM MASS SPECTROMETRY;

EID: 79953185706     PISSN: 07317085     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jpba.2011.02.009     Document Type: Article

References (30)

1. Jordan V.C. New insights into the metabolism of tamoxifen and its role in the treatment and prevention of breast cancer. Steroids 2007, 72:829-842.
2. Schwartz J. Tamoxifen: an emerging preventive. Front. Biosci. 2004, 9:2827-2847.
3. Kool J., Ramautar R., van Liempd S.M., Beckman J., de Kanter F.J., Meerman J.H., Schenk T., Irth H., Commandeur J.N., Vermeulen N.P. Rapid on-line profiling of estrogen receptor binding metabolites of tamoxifen. J. Med. Chem. 2006, 49:3287-3292.
4. Boocock D.J., Maggs J.L., White I.N., Park B.K. Alpha-hydroxytamoxifen, a genotoxic metabolite of tamoxifen in the rat: identification and quantification in vivo and in vitro. Carcinogenesis 1999, 20:153-160.
5. Furr B.J., Jordan V.C. The pharmacology and clinical uses of tamoxifen. Pharmacol. Ther. 1984, 25:127-205.
6. Stearns V., Johnson M.D., Rae J.M., Morocho A., Novielli A., Bhargava P., Hayes D.F., Desta Z., Flockhart D.A. Active tamoxifen metabolite plasma concentrations after coadministration of tamoxifen and the selective serotonin reuptake inhibitor paroxetine. J. Natl. Cancer Inst. 2003, 95:1758-1764.
7. Lien E.A., Solheim E., Lea O.A., Lundgren S., Kvinnsland S., Ueland P.M. Distribution of 4-hydroxy-N-desmethyltamoxifen and other tamoxifen metabolites in human biological fluids during tamoxifen treatment. Cancer Res. 1989, 49:2175-2183.
8. Teunissen S.F., Rosing H., Koornstra R.H., Linn S.C., Schellens J.H., Schinkel A.H., Beijnen J.H. Development and validation of a quantitative assay for the analysis of tamoxifen with its four main metabolites and the flavonoids daidzein, genistein and glycitein in human serum using liquid chromatography coupled with tandem mass spectrometry. J. Chromatogr. B: Analyt. Technol. Biomed. Life Sci. 2009, 877:2519-2529.
9. Johnson M.D., Zuo H., Lee K.H., Trebley J.P., Rae J.M., Weatherman R.V., Desta Z., Flockhart D.A., Skaar T.C. Pharmacological characterization of 4-hydroxy-N-desmethyl tamoxifen, a novel active metabolite of tamoxifen. Breast Cancer Res. Treat. 2004, 85:151-159.
10. Dehal S.S., Kupfer D. Evidence that the catechol 3,4-dihydroxytamoxifen is a proximate intermediate to the reactive species binding covalently to proteins. Cancer Res. 1996, 56:1283-1290.
11. Lim C.K., Yuan Z.X., Lamb J.H., White I.N., De Matteis F., Smith L.L. A comparative study of tamoxifen metabolism in female rat, mouse and human liver microsomes. Carcinogenesis 1994, 15:589-593.
12. Zhang F., Fan P.W., Liu X., Shen L., van Breeman R.B., Bolton J.L. Synthesis and reactivity of a potential carcinogenic metabolite of tamoxifen: 3,4-dihydroxytamoxifen-o-quinone. Chem. Res. Toxicol. 2000, 13:53-62.
13. McMurry J.E. Titanium-induced dicarbonyl-coupling reactions. Acc. Chem. Res. 1983, 16:405-411.
14. Gauthier S., Mailhot J., Labrie F. New highly stereoselective synthesis of (Z)-4-hydroxytamoxifen and (Z)-4-hydroxytoremifene via McMurry reaction. J. Org. Chem. 1996, 61:3890-3893.
15. Teunissen S.F., Rosing H., Schinkel A.H., Schellens J.H., Beijnen J.H. Bioanalytical methods for determination of tamoxifen and its phase I metabolites: a review. Anal. Chim. Acta 2010, 683:21-37.
16. Buzdar A.U., Kau S., Hortobagyi G.N., Theriault R.L., Booser D., Holmes F.A., Walters R., Krakoff I.H. Phase I trial of droloxifene in patients with metastatic breast cancer. Cancer Chemother. Pharmacol. 1994, 33:313-316.
17. Poon G.K., Chui Y.C., McCague R., Lønning P.E., Feng R., Rowlands M.G., Jarman M. Analysis of phase I and phase II metabolites of tamoxifen in breast cancer patients. Drug Metab. Dispos. 1993, 21:1119-1124.
18. Lim C.K., Chow L.C., Yuan Z.X., Smith L.L. High performance liquid chromatography of tamoxifen and metabolites in plasma and tissues. Biomed. Chromatogr. 1993, 7:311-314.
19. Claude B., Morin P., Bayoudh S., de Ceaurriz J. Interest of molecularly imprinted polymers in the fight against doping. Extraction of tamoxifen and its main metabolite from urine followed by high-performance liquid chromatography with UV detection. J. Chromatogr. A 2008, 1196-1197:81-88.
20. Griffin T.J., Xie H., Bandhakavi S., Popko J., Mohan A., Carlis J.V., Higgins L. iTRAQ reagent-based quantitative proteomic analysis on a linear ion trap mass spectrometer. J. Proteome Res. 2007, 6:4200-4209.
21. Foster A.B., Jarman M., Leung O.T., McCague R., Leclercq G., Devleeschouwer N. Hydroxy derivatives of tamoxifen. J. Med. Chem. 1985, 28:1491-1497.
22. McCague R., Seago A. Aspects of metabolism of tamoxifen by rat liver microsomes. Identification of a new metabolite: E-1-[4-(2-dimethylaminoethoxy)-phenyl]-1,2-diphenyl-1-buten-3-ol N-oxide. Biochem. Pharmacol. 1986, 35:827-834.
23. Crewe H.K., Notley L.M., Wunsch R.M., Lennard M.S., Gillam E.M. Metabolism of tamoxifen by recombinant human cytochrome P450 enzymes: formation of the 4-hydroxy, 4'-hydroxy and N-desmethyl metabolites and isomerization of trans-4-hydroxytamoxifen. Drug Metab. Dispos. 2002, 30:869-874.
24. Krueger S.K., Vandyke J.E., Williams D.E., Hines R.N. The role of flavin-containing monooxygenase (FMO) in the metabolism of tamoxifen and other tertiary amines. Drug Metab. Rev. 2006, 38:139-147.
25. John B.A., Brodie R.R., Baldock G.A., McBurney A., Chasseaud L.F., Jank P., Von Nieciecki A. Pharmacokinetics and metabolism of the anti-oestrogen droloxifene in female human subjects. Xenobiotica 2002, 32:699-713.
26. Jones R.M., Yuan Z.X., Lamb J.H., Lim C.K. On-line high-performance liquid chromatographic-electrospray ionization mass spectrometric method for the study of tamoxifen metabolism. J. Chromatogr. A 1996, 722:249-255.
27. Notley L.M., De Wolf C.J., Wunsch R.M., Lancaster R.G., Gillam E.M. Bioactivation of tamoxifen by recombinant human cytochrome p450 enzymes. Chem. Res. Toxicol. 2002, 15:614-622.
28. Lim C.K., Yuan Z.X., Jones R.M., White I.N., Smith L.L. Identification and mechanism of formation of potentially genotoxic metabolites of tamoxifen: study by LC-MS/MS. J. Pharm. Biomed. Anal. 1997, 15:1335-1342.
29. Lien E.A., Anker G., Lønning P.E., Ueland P.M. Determination of droloxifene and two metabolites in serum by high-pressure liquid chromatography. Ther. Drug Monit. 1995, 17:259-265.
30. Mazzarino M., Fiacco I., de la Torre X., Botre F. A mass spectrometric approach for the study of the metabolism of clomiphene, tamoxifen and toremifene by liquid chromatography time-of-flight spectroscopy. Eur. J. Mass Spectrom. (Chichester, Eng.) 2008, 14:171-180.