Tandem mass spectrometry approach for the investigation of the steroidal metabolism: Structure-fragmentation relationship (SFR) in anabolic steroids and their metabolites by ESI-MS/MS analysis

Steroids

Volumn 78, Issue 2, 2013, Pages 171-181

  Musharraf, Syed Ghulam ^a   Ali, Arslan ^a   Khan, Naik Tameem ^a   Yousuf, Maria ^a   Choudhary, Muhammad Iqbal ^a,b   Atta Ur Rahman, ^a  

^a UNIVERSITY OF KARACHI   (Pakistan)

^b KING SAUD UNIVERSITY   (Saudi Arabia)

Author keywords

Anabolic steroids; QTOF mass spectrometry; Steroid metabolite

Indexed keywords

11ALPHA HYDROXYANDROST 1,4 DIEN 3,17 DIONE; 11ALPHA HYDROXYMETHANDROSTENOLONE; 11ALPHA HYDROXYMETHYLTESTOSTERONE; 12BETA,15ALPHA DIHYDROXYMETHYLTESTOSTERONE; 15ALPHA HYDROXYMETHANDROSTENOLONE; 15ALPHA HYDROXYMETHYLTESTOSTERONE; 17BETA HYDROXYANDROST 4 EN 3,11 DIONE; 6BETA HYDROXYMETHANDROSTENOLONE; 6BETA HYDROXYMETHYLTESTOSTERONE; 7BETA HYDROXY ANDROSTERONE; 9ALPHA HYDROXY ADRENOSTERONE; ADRENOSTERONE; ANABOLIC AGENT; ANDROSTANEDIONE; ANDROSTANOLONE; ANDROSTERONE; METANDIENONE; METHYLTESTOSTERONE; TESTOSTERONE; TRANS ANDROSTERONE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DISSOCIATION; DRUG METABOLISM; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; FRAGMENTATION REACTION; HYDROXYLATION; OXIDATION; STEROID METABOLISM; TANDEM MASS SPECTROMETRY;

ANABOLIC AGENTS; ANDROSTENES; CHROMATOGRAPHY, LIQUID; FERMENTATION; METABOLIC NETWORKS AND PATHWAYS; METHYLTESTOSTERONE; REFERENCE STANDARDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STEROIDS; STRUCTURE-ACTIVITY RELATIONSHIP; TANDEM MASS SPECTROMETRY;

MACROPHOMINA PHASEOLINA;

EID: 84871461320     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.10.017     Document Type: Article

References (27)

1. A.T. Kicman, and D.B. Gower Anabolic steroids in sport: biochemical, clinical, and analytical perspectives Ann Clin Biochem 40 2003 321 356
2. M. Parssinen, and T. Seppala Steroid use and long-term health risks in former athletes Sports Med 32 2002 83 94
3. World Anti-Doping Agency, the World Anti-Doping Code - the 2012 Prohibited List. Available at: http://www.wada-ama.org/Documents/World-Anti- oping-Program/WADP-Prohibited-list/2012/WADA-Prohibited-List-2012-EN.pdf.
4. R. Draisci, L. Palleschi, E. Ferretti, L. Lucentini, and F.D. Quadri Confirmatory analysis of 17-boldenone, and androsta-1,4-diene-3,17-dione in bovine urine by liquid chromatography-tandem mass spectrometry J Chromatogr B Anal Technol Biomed Life Sci 789 2003 219 226
5. C.V. Poucke, and C.V. Peteghem Development and validation of a multi-analyte method for the detection of anabolic steroids in bovine urine with liquid chromatography-tandem mass spectrometry J Chromatogr B Anal Technol Biomed Life Sci 77 2002 211 217
6. C.V. Poucke, and C.V. Peteghem Development and validation of a multi-analyte method for the detection of anabolic steroids in bovine urine with liquid chromatography-tandem mass spectrometry J Chromatogr B Anal Technol Biomed Life Sci 77 2002 211 217
7. C.G. Georgakopoulos, A. Vonaparti, M. Stamou, P. Kiousi, E. Lyris, Y.S. Angelis, G. Tsoupras, B. Wuest, M.W.F. Nielen, I. Panderi, and M. Koupparis Preventive doping control analysis: liquid and gas chromatography time-of-flight mass spectrometry for detection of designer steroids Rapid Commun Mass Spectrom 21 2007 2439 2446
8. D.H. Catlin, M.H. Sekera, B.D. Ahrens, B. Starcevic, Y. Chang, and C.K. Hatton Tetrahydrogestrinone: discovery, synthesis, and detection in urine Rapid Commun Mass Spectrom 18 2004 1245 1249
9. F. Guan, L.R. Soma, Y. Luo, C.E. Uboh, and S. Peterman Collision-induced dissociation pathways of anabolic steroids by electrospray ionization tandem mass spectrometry J Am Soc Mass Spectrom 17 2006 477 489
10. F. Guan, C.E. Uboh, L.R. Soma, Y. You, Y. Liu, and X. Li Correlation of product ion profiles with molecular structures of androgenic and anabolic steroids in ESI-MS/MS J Mass Spectrom 45 2010 1261 1269
11. O.J. Pozo, P.V. Eenoo, K. Deventer, S. Grimalt, J.V. Sancho, F. Hernández, and F.T. Delbeke Collision-induced dissociation of 3-keto anabolic steroids and related compounds after electrospray ionization. Considerations for structural elucidation Rapid Commun Mass Spectrom 22 2008 4009 4024
12. M. Thevis, and W. Schänzer Mass spectrometric analysis of androstan-17 beta-ol-3-one and androstadiene-17 beta-ol-3-one isomers J Am Soc Mass Spectrom 16 2005 1660 1669
13. W. Schanzer, and M. Donike Metabolism of anabolic steroids in man: synthesis and use of reference substances for identification of anabolic steroid metabolites Anal Chim Acta 275 1993 23 48
14. E. Brzezowska, J. Dmochowska-Gladysz, and T. Kolek Biotransformation XXXIX. Metabolism of testosterone, androstenedione, progesterone and testosterone derivatives in Absidia coerulea culture J Steroid Biochem Mol Biol 57 1996 357 362
15. E. Huszcza, and J. Dmochowska-Gladysz Transformations of testosterone and related steroids by Botrytis cinerea Phytochemistry 62 2003 155 158
16. B. Songtao, D. Lianxiang, Z. Liming, and L. Fuping Bioconversion of methyl-testosterone in a biphasic system Process Biochem. 40 2005 3309 3313
17. O.J. Pozo, P.V. Eenoo, K. Deventer, L. Lootens, W.V. Thuyne, M.K. Parr, W. Schänzer, J.V. Sancho, F. Hernández, P. Meuleman, G. Leroux-Roels, and F.T. Delbeke Detection and characterization of new metabolite of 17α-methyltestosterone Drug Metab Dispos 37 2010 2153 2162
18. F. Guan, C.E. Uboh, L.R. Soma, Y. You, Y. Liu, and X. Li High-throughput UHPLC-MS/MS method for the detection, quantification and identification of fifty-five anabolic and androgenic steroids in equine plasma J Mass Spectrom 45 2010 1270 1279
19. O.J. Pozo, P.V. Eenoo, K. Deventer, and F.T. Delbeke Detection and characterization of anabolic steroids in doping analysis by LC-MS Trend Anal Chem 27 2008 657 671
20. E.A. Abourashed, A.M. Clark, and C.D. Hufford Microbial models of mammalian metabolism of xenobiotics: an updated review Curr Med Chem 6 1999 359 374
21. C. Moussa, P. Houziaux, B. Danree, and R. Azerad Microbial models of mammalian metabolism. Fungal metabolism of phenolic and nonphenolic p-cymene-related drugs and prodrugs. II. Metabolites of nonphenolic derivatives Drug Metab Dispos 25 1997 311 316
22. S.G. Musharraf, A. Ali, R.A. Ali, S. Yousuf, M.I. Choudhary, and Atta-ur-Rahman Analysis and development of structure-fragmentation relationships in withanolides using an electrospray ionization quadropole time-of-flight tandem mass spectrometry hybrid instrument Rapid Commun Mass Spectrom 25 2011 104 114
23. S.G. Musharraf, M. Goher, A. Ali, A. Adhikari, M.I. Choudhary, and Atta-ur-Rahman Rapid characterization and identification of steroidal alkaloids in Sarcococca coriacea using liquid chromatography coupled with electrospray ionization quadropole time-of-flight mass spectrometry Steroids 77 2012 138 148
24. S.G. Musharraf, M. Goher, P. Wafo, and R.S.T. Kamdem Electrospray tandem mass spectrometric analysis of duboscic acid, exploring the structural features of a new class of triterpenoids, dubosane Int J Mass Spectrom 310 2012 77 80
25. M.W.F. Nielen, J.P.C. Vissers, R.E.M. Fuchs, J.W. van Velde, and A. Lommen Screening for anabolic steroids and related compounds in illegal cocktails by liquid chromatography/time-of-flight mass spectrometry and liquid chromatography/quadrupole time-of-flight tandem mass spectrometry with accurate mass measurement Rapid Commun Mass Spectrom 15 2001 1577 1585
26. M.W.F. Nielen, T.F.H. Bovee, M.C.V. Engelen, P. Rutgers, A.R.M. Hamers, J.A.V. Rhijn, and L.A.P. Hoogenboom Urine testing for designer steroids by liquid chromatography with androgen bioassay detection and electrospray quadrupole time-of-flight mass spectrometry identification Anal Chem 78 2006 424 431
27. M.I. Choudhary, N.T. Khan, S.G. Musharraf, S. Anjum, and Atta-ur-Rahman Biotransformation of adrenosterone by filamentous fungus, Cunninghamella elegans Steroids 72 2007 923 929