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Structural elucidation of major selective androgen receptor modulator (SARM) metabolites for doping control
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Chemical Biology for Biomarker Discovery. Uppsala University, Science for Life Laboratory, SciLifeLab.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Science. Nat Vet Inst SVA, Dept Chem Environm & Feed Hyg, SE-75189 Uppsala, Sweden..
Univ Calif Davis, Sch Vet Med, KL Maddy Equine Analyt Chem Lab, Davis, CA 95616 USA.;Univ Calif Davis, Sch Vet Med, Dept Vet Mol Biosci, Davis, CA 95616 USA..
Univ Calif Davis, Sch Vet Med, KL Maddy Equine Analyt Chem Lab, Davis, CA 95616 USA.;Univ Calif Davis, Sch Vet Med, Dept Vet Mol Biosci, Davis, CA 95616 USA..
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2018 (English)In: Organic and biomolecular chemistry, ISSN 1477-0520, E-ISSN 1477-0539, Vol. 16, no 5, p. 698-702Article in journal (Refereed) Published
Abstract [en]

Selective androgen receptor modulators (SARMs) are a class of androgen receptor drugs, which have a high potential to be performance enhancers in human and animal sports. Arylpropionamides are one of the major SARM classes and get rapidly metabolized significantly complicating simple detection of misconduct in blood or urine sample analysis. Specific drug-derived metabolites are required as references due to a short half-life of the parent compound but are generally lacking. The difficulty in metabolism studies is the determination of the correct regio and stereoselectivity during metabolic conversion processes. In this study, we have elucidated and verified the chemical structure of two major equine arylpropionamide-based SARM metabolites using a combination of chemical synthesis and liquid chromatography- mass spectrometry (LC-MS) analysis. These synthesized SARM-derived metabolites can readily be utilized as reference standards for routine mass spectrometry-based doping control analysis of at least three commonly used performance-enhancing drugs to unambigously identify misconduct.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2018. Vol. 16, no 5, p. 698-702
National Category
Basic Medicine
Identifiers
URN: urn:nbn:se:uu:diva-345712DOI: 10.1039/c7ob03030dISI: 000423787600004PubMedID: 29319101OAI: oai:DiVA.org:uu-345712DiVA, id: diva2:1190376
Funder
Science for Life Laboratory - a national resource center for high-throughput molecular bioscienceAvailable from: 2018-03-14 Created: 2018-03-14 Last updated: 2018-03-14Bibliographically approved

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Garg, NeerajHansson, AnnelieBondesson, UlfHedeland, MikaelGlobisch, Daniel

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Chemical Biology for Biomarker DiscoveryScience for Life Laboratory, SciLifeLabAnalytical Science
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