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A multivariate data analysis approach for the investigation of in vitro derived metabolites of ACP-105 in comparison with human in vivo metabolites
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.ORCID iD: 0000-0002-2846-8938
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Analytical Pharmaceutical Chemistry.
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2023 (English)In: Journal of chromatography. B, ISSN 1570-0232, E-ISSN 1873-376X, Vol. 1231, article id 123927Article in journal (Refereed) Published
Abstract [en]

Selective androgen receptor modulators (SARMs) such as ACP-105 are prohibited in sports due to their anabolic properties. ACP-105 has in previous equine studies shown to undergo extensive metabolism, which makes its metabolite profile important to investigate in humans, since the metabolism is unknown in this species. The aims of the study were to systematically optimize in vitro microsome incubations for improved metabolite yield and to utilize a multivariate data analysis (MVDA) approach to aid the metabolite discovery. Microsomes together with S9 fractions were used at optimal conditions, both with and without phase II additives. Furthermore, the relevance of the in vitro derived metabolites was evaluated as analytical targets in doping control by comparison with results from a human post-administration urine sample collected after a single dose of 100 µg ACP-105. All samples were analyzed with liquid chromatography - Orbitrap mass spectrometry.

The use of the systematical optimization and MVDA greatly simplified the search and a total of 18 in vitro metabolites were tentatively identified. The yield of the two main monohydroxylated isomers increased by 24 and 10 times, respectively. In the human urine sample, a total of seven metabolites of ACP-105, formed by a combination of hydroxylations and glucuronic acid conjugations, were tentatively identified. The main metabolites were two monohydroxylated forms that are suggested as analytical targets for human doping control after hydrolysis. All the in vivo metabolites could be detected with the MVDA approach on the in vitro models, demonstrating its usefulness for prediction of the in vivo metabolite profile.

Place, publisher, year, edition, pages
Elsevier, 2023. Vol. 1231, article id 123927
Keywords [en]
ACP-105, Doping control, MVDA, Metabolites in vivo and in vitro, Microsomes, UHPLC-HRMS
National Category
Analytical Chemistry Pharmaceutical Sciences
Identifiers
URN: urn:nbn:se:uu:diva-517780DOI: 10.1016/j.jchromb.2023.123927ISI: 001112393600001PubMedID: 37972465OAI: oai:DiVA.org:uu-517780DiVA, id: diva2:1818928
Available from: 2023-12-12 Created: 2023-12-12 Last updated: 2024-02-05Bibliographically approved
In thesis
1. Metabolite Profiling of Drugs using Mass Spectrometry: Identification of analytical targets for doping control and improvements of the metabolite search process
Open this publication in new window or tab >>Metabolite Profiling of Drugs using Mass Spectrometry: Identification of analytical targets for doping control and improvements of the metabolite search process
2024 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

Doping is defined as the use of prohibited substances or methods by the World Anti-Doping Agency and the aim with doping control analysis is to detect the use of these illicit substances or methods. Substances that are prohibited in human or equine sports have either a positive or negative impact on the performance. Since administered drugs generally are metabolized to a varying degree and thereby not only excreted in their original form, their metabolite profiles are of high interest because drug metabolites may be present in the body for a longer time than the administered drug itself. Thereby detection of metabolites can improve the window of detection. Unfortunately, the metabolite profiles of non-approved drugs that are mainly available on the Internet, such as Selective Androgen Receptor Modulators (SARMs) are often unknown. 

This thesis consists of four papers that all encompass drug metabolite profiling either in vivo, in vitro or in a combination, utilizing separation with liquid chromatography and detection with high resolution mass spectrometry. In paper I and II, the equine in vivo metabolite profiles of the two SARMs ACP-105 and LGD-3303 were investigated and the results showed that using drug metabolites as analytical targets can prolong the detection time. For ACP-105, the in vivo metabolite profile was compared with different incubation models such as liver microsomes, S9 fractions and the fungus Cunninghamella elegans. The in vivo and in vitro metabolite profiles showed an interesting overlap for several metabolites, demonstrating the importance and usefulness for in vitro methods in doping control, especially since microsome incubates are allowed as reference material. An optimization of microsome incubation conditions utilizing experimental design was presented in paper III and IV, showing that the optimized conditions greatly impacted the yield of drug metabolites, but also that the optimal conditions are substance dependent. In paper III, a multivariate data analysis search tool utilizing OPLS-DA was presented, which greatly simplified the in vitro drug metabolite identification process of ACP-105 and the results showed relevance in comparison with human in vivo metabolites.

In conclusion, several new analytical targets with improved detectability for equine and human doping control have been presented, where the drug metabolite profile showed to be of great importance. All together, these new analytical targets, the optimized microsome incubation conditions for improved metabolite yield and the search tool that aids the metabolite investigation through multivariate data analysis, have made a positive contribution to the doping control area.

Place, publisher, year, edition, pages
Uppsala: Acta Universitatis Upsaliensis, 2024. p. 47
Series
Digital Comprehensive Summaries of Uppsala Dissertations from the Faculty of Pharmacy, ISSN 1651-6192 ; 348
Keywords
Mass spectrometry, UHPLC-HRMS, Doping control, Metabolite profile, SARM, Selective Androgen Receptor Modulator, MVDA, Microsomes, Experimental design
National Category
Pharmaceutical Sciences Analytical Chemistry
Research subject
Analytical Pharmaceutical Chemistry
Identifiers
urn:nbn:se:uu:diva-521781 (URN)978-91-513-2031-1 (ISBN)
Public defence
2024-03-22, room B42, BMC, Husargatan 3, Uppsala, 09:15 (English)
Opponent
Supervisors
Available from: 2024-02-29 Created: 2024-02-05 Last updated: 2024-02-29

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