Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control

Sulfate metabolites have been described as long-term metabolites for some anabolic androgenic steroids (AAS). 4-chlorometandienone (4Cl-MTD) is one of the most frequently detected AAS in sports drug testing and it is commonly detected by monitoring metabolites excreted free or conjugated with glucur...

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Authors: Balcells Aribau, Georgina, 1987-, Gómez, Cristina, Garrostas, Lorena, Pozo Mendoza, Óscar J., 1975-, Ventura Alemany, Rosa
Format: article
Status:Versión aceptada para publicación
Publication Date:2017
Country:España
Institution:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
Repository:Recercat. Dipósit de la Recerca de Catalunya
OAI Identifier:oai:recercat.cat:10230/32509
Online Access:http://hdl.handle.net/10230/32509
http://dx.doi.org/10.1002/dta.2101
Access Level:Open access
Keyword:Dopatge en els esports -- Control
Metabòlits
Sulfats
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spelling Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping controlBalcells Aribau, Georgina, 1987-Gómez, CristinaGarrostas, LorenaPozo Mendoza, Óscar J., 1975-Ventura Alemany, RosaDopatge en els esports -- ControlMetabòlitsSulfatsSulfate metabolites have been described as long-term metabolites for some anabolic androgenic steroids (AAS). 4-chlorometandienone (4Cl-MTD) is one of the most frequently detected AAS in sports drug testing and it is commonly detected by monitoring metabolites excreted free or conjugated with glucuronic acid. Sulfation reactions of 4Cl-MTD have not been studied. The aim of this work was to evaluate the sulfate fraction of 4Cl-MTD metabolism by liquid chromatography-tandem mass spectrometry (LC-MS/MS) to establish potential long-term metabolites valuable for doping control purposes. 4Cl-MTD was administered to two healthy male volunteers and urine samples were collected up to 8 days after administration. A theoretical selected reaction monitoring (SRM) method working in negative mode was developed. Ion transitions were based on ionization and fragmentation behaviour of sulfate metabolites as well as specific neutral losses (NL of 15 Da and NL of 36 Da) of compounds with related chemical structure. Six sulfate metabolites were detected after the analysis of excretion study samples. Three of the identified metabolites were characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and gas chromatography-tandem mass spectrometry (GC-MS/MS). Results showed that five out of the six identified sulfate metabolites were detected in urine up to the last collected samples from both excretion studies. Copyright © 2016 John Wiley & Sons, Ltd.The financial support received from the World Anti-Doping Agency WADA (12A21RV), Ministerio de Economía y Competividad (Gobierno de España) (Project number DEP2012-35612) and Generalitat de Catalunya (Consell Català de l’Esport, DIUE 2014SGR 692) is gratefully acknowledgedWiley20172017info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfapplication/pdfhttp://hdl.handle.net/10230/32509http://dx.doi.org/10.1002/dta.2101reponame:Recercat. Dipósit de la Recerca de Catalunyainstname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)InglésDrug Testing and Analysis. 2017;9(7):983-93info:eu-repo/grantAgreement/ES/3PN/DEP2012-35612This is the peer reviewed version of the following article: Balcells G, Gómez C, Garrostas L, Pozo ÓJ, Ventura R. Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control. Drug Test Anal. 2016 Sep 30. [Epub ahead of print] , which has been published in final form at http://dx.doi.org/10.1002/dta.2101. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archivinginfo:eu-repo/semantics/openAccessoai:recercat.cat:10230/325092026-05-29T05:05:01Z
dc.title.none.fl_str_mv Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
title Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
spellingShingle Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
Balcells Aribau, Georgina, 1987-
Dopatge en els esports -- Control
Metabòlits
Sulfats
title_short Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
title_full Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
title_fullStr Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
title_full_unstemmed Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
title_sort Sulfate metabolites as alternative markers for the detection of 4-chlorometandienone misuse in doping control
dc.creator.none.fl_str_mv Balcells Aribau, Georgina, 1987-
Gómez, Cristina
Garrostas, Lorena
Pozo Mendoza, Óscar J., 1975-
Ventura Alemany, Rosa
author Balcells Aribau, Georgina, 1987-
author_facet Balcells Aribau, Georgina, 1987-
Gómez, Cristina
Garrostas, Lorena
Pozo Mendoza, Óscar J., 1975-
Ventura Alemany, Rosa
author_role author
author2 Gómez, Cristina
Garrostas, Lorena
Pozo Mendoza, Óscar J., 1975-
Ventura Alemany, Rosa
author2_role author
author
author
author
dc.subject.none.fl_str_mv Dopatge en els esports -- Control
Metabòlits
Sulfats
topic Dopatge en els esports -- Control
Metabòlits
Sulfats
description Sulfate metabolites have been described as long-term metabolites for some anabolic androgenic steroids (AAS). 4-chlorometandienone (4Cl-MTD) is one of the most frequently detected AAS in sports drug testing and it is commonly detected by monitoring metabolites excreted free or conjugated with glucuronic acid. Sulfation reactions of 4Cl-MTD have not been studied. The aim of this work was to evaluate the sulfate fraction of 4Cl-MTD metabolism by liquid chromatography-tandem mass spectrometry (LC-MS/MS) to establish potential long-term metabolites valuable for doping control purposes. 4Cl-MTD was administered to two healthy male volunteers and urine samples were collected up to 8 days after administration. A theoretical selected reaction monitoring (SRM) method working in negative mode was developed. Ion transitions were based on ionization and fragmentation behaviour of sulfate metabolites as well as specific neutral losses (NL of 15 Da and NL of 36 Da) of compounds with related chemical structure. Six sulfate metabolites were detected after the analysis of excretion study samples. Three of the identified metabolites were characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS) and gas chromatography-tandem mass spectrometry (GC-MS/MS). Results showed that five out of the six identified sulfate metabolites were detected in urine up to the last collected samples from both excretion studies. Copyright © 2016 John Wiley & Sons, Ltd.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10230/32509
http://dx.doi.org/10.1002/dta.2101
url http://hdl.handle.net/10230/32509
http://dx.doi.org/10.1002/dta.2101
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Drug Testing and Analysis. 2017;9(7):983-93
info:eu-repo/grantAgreement/ES/3PN/DEP2012-35612
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:Recercat. Dipósit de la Recerca de Catalunya
instname:Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
instname_str Varias* (Consorci de Biblioteques Universitáries de Catalunya, Centre de Serveis Científics i Acadèmics de Catalunya)
reponame_str Recercat. Dipósit de la Recerca de Catalunya
collection Recercat. Dipósit de la Recerca de Catalunya
repository.name.fl_str_mv
repository.mail.fl_str_mv
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