Combined chemical and biotechnological production of 20βOH-NorDHCMT, a long-term metabolite of Oral-Turinabol (DHCMT)
| Autor: | Xavier de la Torre, Jan Felix Joseph, Lei Chen, Francesco Botrè, Maria Kristina Parr, Alexandra Naß, Matthias Bureik, Jiaxin Liu, Anna Stoll, Gerhard Wolber |
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| Rok vydání: | 2018 |
| Předmět: |
0301 basic medicine
Metabolite Urine Anabolic androgenic steroids Pharmacology 01 natural sciences Biochemistry Gas Chromatography-Mass Spectrometry law.invention Inorganic Chemistry 03 medical and health sciences chemistry.chemical_compound Anabolic Agents Biotransformation law Schizosaccharomyces Doping Humans Testosterone Doping in Sports chemistry.chemical_classification Fission yeast Whole-cell biotransformation 010401 analytical chemistry Yeast strain Anabolic-Androgenic Steroids 0104 chemical sciences 030104 developmental biology Enzyme chemistry Recombinant DNA Biotechnology Human cytochrome |
| Zdroj: | Journal of Inorganic Biochemistry. 183:165-171 |
| ISSN: | 0162-0134 |
| Popis: | Anabolic androgenic steroids (AAS) are misused very frequently in sport competitions as performance enhancing agents. One of the doping compounds that has been detected with increased frequency in the last few years is dehydrochloromethyltestosterone (DHCMT, 4-chloro-17β-hydroxy-17α-methylandrosta-1,4-dien-3-one; brand name Oral Turinabol). The long-term DHCMT metabolite 20βOH-NorDHCMT (4-chloro-17β-hydroxymethyl-17α-methyl-18-norandrosta-1,4,13-trien-3-one) was reported earlier to be detectable in urine samples for more than 22 days after DHCMT administration; however, purified reference material was not available so far. In this study we demonstrate a successful combination of Wagner-Meerwein rearrangement of DHCMT to NorDHCMT (4-chloro-17,17-dimethyl-18-norandrosta-1,4,13-trien-3-one) and subsequent whole-cell biotransformation with a recombinant fission yeast strain expressing the human cytochrome P450 enzyme (CYP or P450) CYP21A2 for the synthesis of mg amounts of this metabolite. It was then used as reference for the analysis of a post administration urine of DHCMT. The availability of this reference compound will provide an incontestable proof for DHCMT abuse. |
| Databáze: | OpenAIRE |
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