{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,24]],"date-time":"2026-03-24T15:02:25Z","timestamp":1774364545177,"version":"3.50.1"},"reference-count":26,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2017,6,18]],"date-time":"2017-06-18T00:00:00Z","timestamp":1497744000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2017,7,30]]},"abstract":"<jats:sec>\n                    <jats:title>Rationale<\/jats:title>\n                    <jats:p>\n                      Selective androgen receptor modulators (SARMs) represent an emerging class of therapeutics targeting\n                      <jats:italic>inter alia<\/jats:italic>\n                      conditions referred to as cachexia and sarcopenia. Due to their anabolic properties, the use of SARMs is prohibited in sports as regulated by the World Anti\u2010Doping Agency (WADA), and doping control laboratories test for these anabolic agents in blood and urine. In order to accomplish and maintain comprehensive test methods, the characterization of new drug candidates is critical for efficient sports drug testing. Hence, in the present study the mass spectrometric properties of the SARM YK\u201011 were investigated.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Methods<\/jats:title>\n                    <jats:p>YK\u201011 was synthesized according to literature data and three different stable\u2010isotope\u2010labeled analogs were prepared to support the mass spectrometric studies. Using high\u2010resolution\/high\u2010accuracy mass spectrometry following electrospray ionization as well as electron ionization, the dissociation pathways of YK\u201011 were investigated, and characteristic features of its (product ion) mass spectra were elucidated. These studies were flanked by density functional theory (DFT) computation providing information on proton affinities of selected functional groups of the analyte.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>Results and Conclusions<\/jats:title>\n                    <jats:p>The steroidal SARM YK\u201011 was found to readily protonate under ESI conditions followed by substantial in\u2010source dissociation processes eliminating methanol, acetic acid methyl ester, and\/or ketene. DFT computation yielded energetically favored structures of the protonated species resulting from the aforementioned elimination processes particularly following protonation of the steroidal D\u2010ring substituent. Underlying dissociation pathways were suggested, supported by stable\u2010isotope labeling of the analyte, and diagnostic product ions for the steroidal nucleus and the D\u2010ring substituent were identified. Further, trimethylsilylated YK\u201011 and its deuterated analogs were subjected to electron ionization high\u2010resolution\/high\u2010accuracy mass spectrometry, complementing the dataset characterizing this new SARM. The obtained fragment ions resulted primarily from A\/B\u2010 and C\/D\u2010ring structures of the steroidal nucleus, thus supporting future studies e.g. concerning metabolic pathways of the substance. Copyright \u00a9 2017 John Wiley &amp; Sons, Ltd.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.7886","type":"journal-article","created":{"date-parts":[[2017,4,25]],"date-time":"2017-04-25T06:39:53Z","timestamp":1493102393000},"page":"1175-1183","source":"Crossref","is-referenced-by-count":19,"title":["Mass spectrometric characterization of the selective androgen receptor modulator (SARM) YK\u201011 for doping control purposes"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-1535-6451","authenticated-orcid":false,"given":"Mario","family":"Thevis","sequence":"first","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Thomas","family":"Piper","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Josef","family":"Dib","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"Lagojda","sequence":"additional","affiliation":[{"name":"Bayer AG  Alfred\u2010Nobel\u2010Str. 50 40789 Monheim Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Dirk","family":"K\u00fchne","sequence":"additional","affiliation":[{"name":"Bayer AG  Alfred\u2010Nobel\u2010Str. 50 40789 Monheim Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Lars","family":"Packschies","sequence":"additional","affiliation":[{"name":"Regional Computing Centre (RRZK) University of Cologne  Weyertal 121 50931 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hans","family":"Geyer","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"},{"name":"European Monitoring Center for Emerging Doping Agents (EuMoCEDA)  Cologne\/Bonn Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Wilhelm","family":"Sch\u00e4nzer","sequence":"additional","affiliation":[{"name":"Center for Preventive Doping Research \u2013 Institute of Biochemistry German Sport University Cologne  Am Sportpark M\u00fcngersdorf 6 50933 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2017,6,18]]},"reference":[{"key":"e_1_2_6_2_1","volume-title":"Anti\u2010Doping Testing Figures","year":"2015"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.forsciint.2011.07.014"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.1466"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/dta.1986"},{"key":"e_1_2_6_6_1","volume-title":"Anti\u2010Doping Testing Figures \u2013 Archives"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1097\/SPC.0000000000000015"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.2217\/fon.13.273"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncpendmet0120"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.2174\/156802606776173456"},{"key":"e_1_2_6_11_1","first-page":"162","article-title":"Development of selective androgen receptor modulators and their therapeutic applications","volume":"8","author":"Chen F.","year":"2002","journal-title":"Zhonghua Nan Ke Xue"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1124\/mi.5.3.7"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.drudis.2007.01.003"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm900280m"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.2217\/fon.09.106"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.4103\/1008-682X.122581"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1177\/1941738113502296"},{"key":"e_1_2_6_18_1","first-page":"821","article-title":"Selective androgen receptor modulators for frailty and osteoporosis","volume":"8","author":"Kilbourne E. 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