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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 (2012-11-20)
Syed Ghulam Musharraf, Arslan Ali, Naik Tameem Khan, Maria Yousuf, Muhammad Iqbal Choudhary, Atta-ur-Rahman
ABSTRACT

Electrospray ionization tandem mass spectrometry (ESI-MS/MS) was used to investigate the effect of different substitutions introduced during metabolism on fragmentation patterns of four anabolic steroids including methyltestosterone, methandrostenolone, cis-androsterone and adrenosterone, along with their metabolites. Collision-induced dissociation (CID) analysis was performed to correlate the major product ions of 19 steroids with structural features. The analysis is done to portray metabolic alteration, such as incorporation or reduction of double bonds, hydroxylations, and/or oxidation of hydroxyl moieties to keto functional group on steroidal skeleton which leads to drastically changed product ion spectra from the respective classes of steroids, therefore, making them difficult to identify. The comparative ESI-MS/MS study also revealed some characteristic peaks to differentiate different steroidal metabolites and can be useful for the unambiguous identification of anabolic steroids in biological fluid. Moreover, LC-ESI-MS/MS analysis of fermented extract of methyltestosterone, obtained by Macrophomina phaseolina was also investigated.

MATERIALS
Product Number
Brand
Product Description

Supelco
17α-Methyltestosterone, VETRANAL®, analytical standard
Sigma-Aldrich
17α-Methyltestosterone, solid (photosensitive)
Sigma-Aldrich
Adrenosterone, 98%
Supelco
17α-Methyltestosterone solution, 1.0 mg/mL in 1,2-dimethoxyethane, ampule of 1 mL, certified reference material, Cerilliant®