PMID: 11906255Mar 22, 2002Paper

Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of methyltestosterone (17 alpha-methylandrost-4-en-17 beta-ol-3-one) and nandrolone (estr-4-en-17 beta-ol-3-one) metabolites

Bioconjugate Chemistry
T KuuranneRisto Kostiainen

Abstract

A new and useful method based on enzyme-assisted synthesis was developed for producing 3 alpha-O-beta-D-glucuronide conjugates from synthetic phase I metabolites of methyltestosterone and nandrolone. The formed glucuronide conjugates of 17 alpha-methyl-5 alpha-androstane-3 alpha,17 beta-diol (I), 17 alpha-methyl-5 beta-androstane-3 alpha,17 beta-diol (II), 5 alpha-estran-3 alpha-ol-17-one (III), and 5 beta-estran-3 alpha-ol-17-one (IV) are urinary metabolites, indicating the human misuse of the above-mentioned anabolic androgenic steroids (AAS). The common lack of reference material precludes the use and validation of these biomarkers in human doping control. Liver microsomes from Aroclor 1254-induced rats were used as a highly active source of mammalian UDP-glucuronosyltransferases (UGT, EC 2.4.1.17). After purification by protein precipitation, liquid-liquid extraction (dichloromethane), C-18 solid-phase extraction, and lyophilization, the steroid glucuronide structures were characterized by (1)H and (13)C NMR spectroscopy and tandem mass spectrometry. The enzymatic method was highly stereoselective, producing a single major conjugate from the parent steroids I-IV. The stereochemically pure steroid glucuronide conjugates were...Continue Reading

References

Aug 1, 1983·Journal of Steroid Biochemistry·P I Mackenzie, I S Owens
May 1, 1996·The Journal of Steroid Biochemistry and Molecular Biology· Sanaullah, L D Bowers
Jul 1, 1997·European Journal of Drug Metabolism and Pharmacokinetics·G M PacificiL Giuliani
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Citations

Mar 12, 2003·Journal of Pharmacological and Toxicological Methods·Matthew G SoarsSteven A Wrighton
Mar 26, 2011·Bioconjugate Chemistry·Jinda FanEvan D Kharasch
Sep 29, 2011·Cancer Biotherapy & Radiopharmaceuticals·Feray KoçanFikriye G Gümüşer
May 19, 2009·European Journal of Pharmaceutical Sciences : Official Journal of the European Federation for Pharmaceutical Sciences·Anna AlonenRisto Kostiainen
Nov 27, 2010·Applied Radiation and Isotopes : Including Data, Instrumentation and Methods for Use in Agriculture, Industry and Medicine·Reyhan YeşilağaçF Z Biber Müftüler
Aug 19, 2008·European Journal of Mass Spectrometry·Tiia KuuranneRisto Kostiainen
Oct 23, 2010·Drug Testing and Analysis·James P ScarthTiia Kuuranne
Aug 16, 2003·Drug Metabolism and Disposition : the Biological Fate of Chemicals·Tiia KuuranneRisto Kostiainen
Apr 30, 2003·Journal of Mass Spectrometry : JMS·R KostiainenS Auriola

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