title: 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.
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.
authors.affiliation: Dr. Panjwani Centre for Molecular Medicine and Drug Research, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan. musharraf1977@yahoo.com
authors.forename: Syed Ghulam
authors.initials: SG
authors.lastname: Musharraf
authors.forename: Arslan
authors.initials: A
authors.lastname: Ali
authors.forename: Naik Tameem
authors.initials: NT
authors.lastname: Khan
authors.forename: Maria
authors.initials: M
authors.lastname: Yousuf
authors.forename: Muhammad Iqbal
authors.initials: MI
authors.lastname: Choudhary
authors.lastname: Atta-ur-Rahman
mesh_terms: D045930:Anabolic Agents / Q000032:analysis* / Q000378:metabolism*; D000736:Androstenes / Q000032:analysis / Q000737:chemistry; D002853:Chromatography, Liquid; D005285:Fermentation; D053858:Metabolic Networks and Pathways; D008777:Methyltestosterone / Q000032:analysis / Q000737:chemistry; D012015:Reference Standards; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D013256:Steroids / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism*; D013329:Structure-Activity Relationship; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D045930:Anabolic Agents; D000736:Androstenes; D013256:Steroids; C011657:adrenosterone; D008777:Methyltestosterone