Characterization of identity, metabolism and androgenic activity of 17-hydroxyandrosta-3,5-diene by GC-MS and a yeast transactivation system

Research output: Contribution to journalResearch articleContributedpeer-review

Contributors

Abstract

Anabolic-androgenic steroids are frequently misused compounds in sports, and they belong to the controlled substances according to the requirements of the World Anti-Doping Agency. The classical techniques of steroid detection are mass spectrometry coupled to gas or liquid chromatography. Biological methods that base on the ability of substances to bind the steroid receptor are not applied in routine doping control procedures so far, but they appear to be useful for characterization of steroid androgenic potential. In this study we used the yeast androgen receptor reporter system (YAS), which in the past has already successfully been applied to both various androgenic substances and also urine samples. Giving attention to the androgenic potential of steroidal dietary supplements, we exemplified the analysis using both mass spectrometry techniques and the YAS-based assay on the product "Syntrax Tetrabol" which was a confiscated dietary supplement and marketed as a steroid precursor. Identification, structure and the kinetic behavior of its excreted metabolites were analyzed by NMR, GC-MS and LC-MS/MS. The androgenic potential of the parent compound as well as its metabolites in urine was evaluated with the help of the YAS. The application of urine samples with a previous deconjugation and the inclusion of urine density values were carried out and led to increased responses on the YAS. Further, the possibility of a complementary application of structure-based instrumental analysis and biological detection of androgenicity with the help of the YAS seems to be desirable and is discussed.

Details

Original languageEnglish
Pages (from-to)1873-84
Number of pages12
JournalArchives of toxicology
Volume86
Issue number12
Publication statusPublished - Dec 2012
Peer-reviewedYes

External IDs

Scopus 84871191225

Keywords

Sustainable Development Goals

Keywords

  • Anabolic Agents/pharmacology, Androgens/pharmacology, Chromatography, High Pressure Liquid, Dihydrotestosterone/metabolism, Doping in Sports/methods, Gas Chromatography-Mass Spectrometry, Humans, Hydrolysis, Indicators and Reagents, Magnetic Resonance Spectroscopy, Male, Middle Aged, Saccharomyces cerevisiae/drug effects, Spectrometry, Mass, Electrospray Ionization, Substance Abuse Detection/methods, Transcriptional Activation/drug effects