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Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry

Oscar Juan Pozo Mendoza UGent, Peter Van Eenoo UGent, Koen Deventer UGent, Leen Lootens UGent, Grimalt Susana, Juan V Sancho, Felix Hernández, Philip Meuleman UGent, Geert Leroux-Roels UGent and Frans Delbeke UGent (2009) STEROIDS. 74(10-11). p.837-852
abstract
The applicability of LC-MS/MS in precursor ion scan mode for the detection of urinary stanozolol metabolites has been studied. The product ion at m/z 81 has been selected as specific for stanozolol metabolites without a modification in A- or N-rings and the product ions at m/z 97 and 145 for the metabolites hydroxylated in the N-ring and 4-hydroxy-stanozolol metabolites, respectively. Under these conditions, the parent drug and up to 15 metabolites were found in a positive doping test sample. The study of a sample from a chimeric uPA-SCID mouse collected after the administration of stanozolol revealed the presence of 4 additional metabolites. The information obtained from the product ion spectra was used to develop a SRM method for the detection of 19 compounds. This SRM method was applied to several doping positive samples. All the metabolites were detected in both the uPA-SCID mouse sample and positive human samples and were not detected in none of the blank samples tested; confirming the metabolic nature of all the detected compounds. In addition, the application of the SRM method to a single human excretion study revealed that one of the metabolites (4 xi,16 xi-dihydroxy-stanozolol) could be detected in negative ionization mode for a longer period than those commonly used in the screening for stanozolol misuse (3'-hydroxy-stanozolol, 16 beta-hydroxy-stanozolol and 4 beta-hydroxy-stanozolol) in doping analysis. The application of the developed approach to several positive doping samples confirmed the usefulness of this metabolite for the screening of stanozolol misuse. Finally, a tentative structure for each detected metabolite has been proposed based on the product ion spectra measured with accurate masses using UPLC-QTOF MS. (C) 2009 Elsevier Inc. All rights reserved.
Please use this url to cite or link to this publication:
author
organization
year
type
journalArticle (original)
publication status
published
subject
keyword
QTOF MS, Precursor ion scan, COLLISION-INDUCED DISSOCIATION, Chimeric mice, ANABOLIC-STEROIDS, ION-TRAP, ELECTROSPRAY-IONIZATION, SCREENING METHOD, MAJOR METABOLITES, DOPING ANALYSIS, HUMAN LIVER, EQUINE URINE, Metabolites, Anabolic steroids, Doping analysis, IDENTIFICATION
journal title
STEROIDS
Steroids
volume
74
issue
10-11
pages
837 - 852
Web of Science type
Article
Web of Science id
000269040400008
JCR category
BIOCHEMISTRY & MOLECULAR BIOLOGY
JCR impact factor
2.905 (2009)
JCR rank
121/281 (2009)
JCR quartile
2 (2009)
ISSN
0039-128X
DOI
10.1016/j.steroids.2009.05.004
language
English
UGent publication?
yes
classification
A1
copyright statement
I have transferred the copyright for this publication to the publisher
id
770709
handle
http://hdl.handle.net/1854/LU-770709
date created
2009-10-29 10:16:48
date last changed
2011-05-24 09:07:19
@article{770709,
  abstract     = {The applicability of LC-MS/MS in precursor ion scan mode for the detection of urinary stanozolol metabolites has been studied. The product ion at m/z 81 has been selected as specific for stanozolol metabolites without a modification in A- or N-rings and the product ions at m/z 97 and 145 for the metabolites hydroxylated in the N-ring and 4-hydroxy-stanozolol metabolites, respectively. Under these conditions, the parent drug and up to 15 metabolites were found in a positive doping test sample. The study of a sample from a chimeric uPA-SCID mouse collected after the administration of stanozolol revealed the presence of 4 additional metabolites. The information obtained from the product ion spectra was used to develop a SRM method for the detection of 19 compounds. This SRM method was applied to several doping positive samples. All the metabolites were detected in both the uPA-SCID mouse sample and positive human samples and were not detected in none of the blank samples tested; confirming the metabolic nature of all the detected compounds. In addition, the application of the SRM method to a single human excretion study revealed that one of the metabolites (4 xi,16 xi-dihydroxy-stanozolol) could be detected in negative ionization mode for a longer period than those commonly used in the screening for stanozolol misuse (3'-hydroxy-stanozolol, 16 beta-hydroxy-stanozolol and 4 beta-hydroxy-stanozolol) in doping analysis. The application of the developed approach to several positive doping samples confirmed the usefulness of this metabolite for the screening of stanozolol misuse. Finally, a tentative structure for each detected metabolite has been proposed based on the product ion spectra measured with accurate masses using UPLC-QTOF MS. (C) 2009 Elsevier Inc. All rights reserved.},
  author       = {Pozo Mendoza, Oscar Juan and Van Eenoo, Peter and Deventer, Koen and Lootens, Leen and Susana, Grimalt and Sancho, Juan V and Hern{\'a}ndez, Felix and Meuleman, Philip and Leroux-Roels, Geert and Delbeke, Frans},
  issn         = {0039-128X},
  journal      = {STEROIDS},
  keyword      = {QTOF MS,Precursor ion scan,COLLISION-INDUCED DISSOCIATION,Chimeric mice,ANABOLIC-STEROIDS,ION-TRAP,ELECTROSPRAY-IONIZATION,SCREENING METHOD,MAJOR METABOLITES,DOPING ANALYSIS,HUMAN LIVER,EQUINE URINE,Metabolites,Anabolic steroids,Doping analysis,IDENTIFICATION},
  language     = {eng},
  number       = {10-11},
  pages        = {837--852},
  title        = {Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry},
  url          = {http://dx.doi.org/10.1016/j.steroids.2009.05.004},
  volume       = {74},
  year         = {2009},
}

Chicago
Pozo Mendoza, Oscar Juan, Peter Van Eenoo, Koen Deventer, Leen Lootens, Grimalt Susana, Juan V Sancho, Felix Hernández, Philip Meuleman, Geert Leroux-Roels, and Frans Delbeke. 2009. “Detection and Structural Investigation of Metabolites of Stanozolol in Human Urine by Liquid Chromatography Tandem Mass Spectrometry.” Steroids 74 (10-11): 837–852.
APA
Pozo Mendoza, O. J., Van Eenoo, P., Deventer, K., Lootens, L., Susana, G., Sancho, J. V., Hernández, F., et al. (2009). Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry. STEROIDS, 74(10-11), 837–852.
Vancouver
1.
Pozo Mendoza OJ, Van Eenoo P, Deventer K, Lootens L, Susana G, Sancho JV, et al. Detection and structural investigation of metabolites of stanozolol in human urine by liquid chromatography tandem mass spectrometry. STEROIDS. 2009;74(10-11):837–52.
MLA
Pozo Mendoza, Oscar Juan, Peter Van Eenoo, Koen Deventer, et al. “Detection and Structural Investigation of Metabolites of Stanozolol in Human Urine by Liquid Chromatography Tandem Mass Spectrometry.” STEROIDS 74.10-11 (2009): 837–852. Print.