Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part I: Phase I metabolites excreted free, as glucuronide and sulfate conjugates, and released after alkaline treatment of the urine

Drug Testing and Analysis

Volumn 4, Issue 10, 2012, Pages 775-785

  Gomez C ^a,b   Pozo, O J ^a   Fabregat, A ^a,b   Marcos, J ^a,b   Deventer, K ^c   Van Eenoo, P ^c   Segura, J ^a,b   Ventura, R ^a,b  

^a HOSPITAL DEL MAR   (Spain)

^b UNIVERSITAT POMPEU FABRA   (Spain)

^c GHENT UNIVERSITY   (Belgium)

Author keywords

Anabolic agents; Boldione; LC MS MS; Metabolism

Indexed keywords

BIOMOLECULES; BODY FLUIDS; CONTROLLED DRUG DELIVERY; DRUG PRODUCTS; GLUCOSE; HYDROXYLATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLITES; PHYSIOLOGY; SULFUR COMPOUNDS; TARGETED DRUG DELIVERY;

ALKALINE TREATMENT; ANABOLIC AGENTS; BOLDENONE; BOLDIONE; HYDROXYLATED METABOLITES; I-PHASE; LC-MS-MS; LC.MS/MS; TESTOSTERONE; URINARY METABOLITES;

METABOLISM;

1,4-ANDROSTADIENE-3,17-DIONE; ANDROSTANE DERIVATIVE; GLUCURONIDE; SULFATE;

ADULT; HUMAN; LIQUID CHROMATOGRAPHY; MALE; METABOLISM; TANDEM MASS SPECTROMETRY; URINE;

ADULT; ANDROSTADIENES; CHROMATOGRAPHY, LIQUID; GLUCURONIDES; HUMANS; MALE; SULFATES; TANDEM MASS SPECTROMETRY;

EID: 84868210632     PISSN: 19427603     EISSN: 19427611     Source Type: Journal    
DOI: 10.1002/dta.1433     Document Type: Article

References (30)

1. F. Hartgens, H. Kuipers. Effects of androgenic-anabolic steroids in athletes. Sport Med 2004, 34, 513.
2. WADA 2012 prohibited list. Available at: http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf June 2012.
3. WADA 2010 laboratory statistics. Available at: http://www.wada-ama.org/Documents/Resources/Statistics/Laboratory_Statistics/WADA_2010_Laboratory_Statistics_Report.pdf June 2012.
4. W. Schänzer. Metabolism of anabolic androgenic steroids. Clin. Chem. 1996, 42, 1001.
5. W. Schänzer, M Donike. Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites. Anal. Chim. Acta 1993, 275, 23.
6. P. van Eenoo, F.T. Delbeke. Metabolism and excretion of anabolic steroids in doping control - New steroids and new insights. J. Steroid Biochem. Mol. Biol. 2006, 101, 161.
7. O.J. Pozo, J. Marcos, J. Segura, R. Ventura. Recent developments in MS for small molecules: application to human doping control analysis. Bioanalysis 2012, 4, 197.
8. B.G. Wolthers, G.P.B. Kraan. Clinical applications of gas chromatography and gas chromatography-mass spectrometry of steroids. J. Chromatogr. A 1999, 843, 247.
9. O.J. Pozo, P. Van Eenoo, K. Deventer, F.T. Delbeke. Detection and characterization of anabolic steroids in doping analysis by LC-MS. TrAC, Trends Anal. Chem. 2008, 27, 657.
10. O.J. Pozo, K. Deventer, P. Van Eenoo, F.T. Delbeke. Detection and characterization of a new metabolite of 17α-methyltestosterone. Anal. Chem. 2008, 80, 1709.
11. O.J. Pozo, R. Ventura, N. Monfort, J. Segura, F.T. Delbeke. Evaluation of different scan methods for the urinary detection of corticosteroid metabolites by liquid chromatography tandem mass spectrometry. J. Mass Spectrom. 2009, 44, 929.
12. C. Gomez, O.J. Pozo, H. Geyer, J. Marcos, M. Thevis, W. Schänzer, et al. New potential markers for the detection of boldenone misuse. J. Steroid Biochem. Mol. Biol. 2012, 132, 239.
13. F. Badoud, E. Grata, J. Boccard, D. Guillarme, J.L. Veuthey, S. Rudaz, et al. Quantification of glucuronidated and sulfated steroids in human urine by ultra-high pressure liquid chromatography quadrupole time-of-flight mass spectrometry. Anal. Bioanal. Chem. 2011, 400, 503.
14. D.J. Borts, L.D. Bowers. Direct measurement of urinary testosterone and epitestosterone conjugates using high-performance liquid chromatography/tandem mass spectrometry. J. Mass Spectrom. 2000, 35, 50.
15. L. Hintikka, T. Kuuranne, A. Leinonen, M. Thevis, W. Schänzer, J. Halket, et al. Liquid chromatographic-mass spectrometric analysis of glucuronide-conjugated anabolic steroid metabolites: method validation and interlaboratory comparison. J. Mass Spectrom. 2008, 43, 965.
16. V.P. Uralets, P.A. Gilette, New anabolic steroids available as nutritional supplements: 5-alpha-androtan-3, 17-diol, 1, 4-androstandien-3, 17-dione and 5-alpha-androst-1-en-17-ol-3-one, in Recent advances in Doping analysis (10) Proceedings of the 20th Cologne Workshop on Dope Analysis Sport und Buch Strauss, (Eds: W. Schänzer, H. Geyer, A. Gotzmann, U. Mareck). Cologne, Germany, 2002, 73.
17. M.A. Popot, S. Boyer, L. Menaut, P. García, Y. Bonnaire, D. Lesage. Boldenone, testosterone and 1, 4-androstadiene-3, 17-dione determination in faeces from horses, untreated and after administration of androsta-1, 4-diene-3, 17-dione (boldione). Biomed. Chromatogr. 2008, 22, 662.
18. B. Destrez, E. Bichon, L. Rambaud, F. Courant, F. Monteau, G. Pinel, et al. Criteria to distinguish between natural situations and illegal use of boldenone, boldenone esters and boldione in cattle 2. Direct measurement of 17beta-boldenone sulpho-conjugate in calf urine by liquid chromatography-high resolution and tandem mass spectrometry. Steroids 2009, 74, 803.
19. K. Verheyden, H. Noppe, L. Vanhaecke, K. Wille, J. Vanden Bussche, K. Bekaert, et al. Excretion of endogenous boldione in human urine: influence of phytosterol consumption. J. Steroid Biochem. Mol. Biol. 2009, 117, 8.
20. O.J. Pozo, J. Marcos, R. Ventura, A. Fabregat, J. Segura. Testosterone metabolism revisited: discovery of new metabolites. Anal Bional. Chem. 2010, 398, 1759.
21. A. Fabregat, O.J. Pozo, J. Marcos, J. Segura, R. Ventura. Alternative markers for the long-term detection of oral testosterone misuse. Steroids 2011, 76, 1367.
22. Y. Kim, M. Jun, W. Lee. Characterization of boldione and its metabolites in human urine by liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 9.
23. W. Schänzer, M. Donike. Metabolism of boldenone in man: gas chromatographic/mass spectrometric identification of urinary excreted metabolites and determination of excretion rates. Biol. Mass Spectrom. 1992, 21, 3.
24. O.J. Pozo, C. Gómez, J. Marcos, J. Segura, R. Ventura. Detection and characterization of urinary metabolites of boldione by LC-MS/MS. Part II: conjugates with cysteine and N-acetylcysteine. Drug Test. Anal. 2012, 4, 786.
25. R. Ventura, M. Roig, N. Monfort, P. Sáez, R. Bergés, J. Segura. High-throughput and sensitive screening by ultra-performance liquid chromatography tandem mass spectrometry of diuretics and other doping agents. Eur. J. Mass Spectrom. 2008, 14, 191.
26. O.J. Pozo, P. Van Eenoo, K. Deventer, S. Grimalt, J.V. Sancho, F. Hernandez, et al. Collision-induced dissociation of 3-keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation. Rapid Commun. Mass Spectrom. 2008, 22, 4009.
27. M. Thevis, H. Geyer, U. Mareck, W. Schänzer. Screening for unknown synthetic steroids in human urine by liquid chromatography-tandem mass spectrometry. J. Mass Spectrom. 2005, 40, 955.
28. M. Thevis, U. Bommerich, G. Opfermann, W. Schänzer. Characterization of chemically modified steroids for doping control purposes by electrospray ionization tandem mass spectrometry. J. Mass Spectrom. 2005, 40, 494.
29. K. Verheyden, B. Le Bizec, D. Courtheyn, V. Mortier, M. Vandewiele, W. Gillis, et al. Mass spectrometric detection of and similarities between 1-androgens. Anal. Chim. Acta 2007, 586, 57.
30. L. Yi, J. Dratter, C. Wang, J.A. Tunge, H. Desaire. Identification of sulfation sites of metabolites and prediction of the compounds' biological effects. Anal. Bioanal. Chem. 2006, 386, 666.