Isolation and characterization of a beta-glucuronide of hydroxylated SARM S1 produced using a combination of biotransformation and chemical oxidation

Rydevik, AxelUppsala universitet,Avdelningen för analytisk farmaceutisk kemi (författare)

In this study, using mass spectrometry and nuclear magnetic resonance (NMR) spectroscopy, it has been confirmed that biotransformation with the fungus Cunninghamella elegans combined with chemical oxidation with the free radical tetramethylpiperidinyl-1-oxy (TEMPO) can produce drug glucuronides of beta-configuration. Glucuronic acid conjugates are a common type of metabolites formed by the human body. The detection of such conjugates in doping control and other kinds of forensic analysis would be beneficial owing to a decrease in analysis time as hydrolysis can be omitted. However the commercial availability of reference standards for drug glucuronides is poor. The selective androgen receptor modulator (SARM) SARM Si was incubated with the fungus C elegans. The sample was treated with the free radical TEMPO oxidizing agent and was thereafter purified by SPE. A glucuronic acid conjugate was isolated using a fraction collector connected to an ultra high performance liquid chromatographic (UHPLC) system. The isolated compound was characterized by NMR spectroscopy and mass spectrometry and its structure was confirmed as a glucuronic acid beta-conjugate of hydroxylated SARM Si bearing the glucuronide moiety on carbon C-10.

Lagojda, AndreasBayer CropScience AG (författare)
Thevis, MarioInstitute of Biochemistry and Center for Preventive Doping Research, German Sport University, Cologne (författare)
Bondesson, UlfUppsala universitet,Avdelningen för analytisk farmaceutisk kemi(Swepub:uu)ulfbonde (författare)
Hedeland, MikaelUppsala universitet,Avdelningen för analytisk farmaceutisk kemi(Swepub:uu)mikahede (författare)
Uppsala universitetAvdelningen för analytisk farmaceutisk kemi (creator_code:org_t)

Ingår i:Journal of Pharmaceutical and Biomedical Analysis: Elsevier BV98, s. 36-390731-70851873-264X

Av författaren/redakt...: Rydevik, Axel; Lagojda, Andreas; Thevis, Mario; Bondesson, Ulf; Hedeland, Mikael

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