{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,30]],"date-time":"2026-05-30T02:16:28Z","timestamp":1780107388067,"version":"3.54.0"},"reference-count":16,"publisher":"Wiley","issue":"9-10","license":[{"start":{"date-parts":[[2025,7,23]],"date-time":"2025-07-23T00:00:00Z","timestamp":1753228800000},"content-version":"vor","delay-in-days":22,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2025,7]]},"abstract":"<jats:title>ABSTRACT<\/jats:title><jats:p><jats:italic>N<\/jats:italic>\u2010((1<jats:italic>R<\/jats:italic>,4<jats:italic>R<\/jats:italic>)\u20104\u2010(3\u2010Chloro\u20104\u2010cyanophenoxy)cyclohexyl)\u20106\u2010(4\u2010((4\u2010(2\u2010(2,6\u2010dioxopiperidin\u20103\u2010yl)\u20106\u2010fluoro\u20101,3\u2010dioxoisoindolin\u20105\u2010yl)piperazin\u20101\u2010yl)methyl)piperidin\u20101\u2010yl)pyridazine\u20103\u2010carboxamide (ARV\u2010110) is a proteolysis\u2010targeting chimera (PROTAC) designed against the androgen receptor (AR), which shows great potential for treating AR\u2010dependent diseases, such as prostate cancer. To support preclinical safety evaluations as well as studies of drug metabolism and pharmacokinetics, two versions of carbon\u201014\u2010labeled ARV\u2010110 were synthesized: <jats:italic>N<\/jats:italic>\u2010((1<jats:italic>R<\/jats:italic>,4<jats:italic>R<\/jats:italic>)\u20104\u2010(3\u2010chloro\u20104\u2010cyanophenoxy)cyclohexyl)\u20106\u2010(4\u2010((4\u2010(2\u2010(2,6\u2010dioxopiperidin\u20103\u2010yl)\u20106\u2010fluoro\u20101,3\u2010[1,3\u2010<jats:sup>14<\/jats:sup>C2]dioxoisoindolin\u20105\u2010yl)piperazin\u20101\u2010yl)methyl)piperidin\u20101\u2010yl)pyridazine\u20103\u2010carboxamide (<jats:sup>14<\/jats:sup>C\u2010ARV\u2010110\u2010<jats:bold>a<\/jats:bold>) and <jats:italic>N<\/jats:italic>\u2010((1<jats:italic>R<\/jats:italic>,4<jats:italic>R<\/jats:italic>)\u20104\u2010(3\u2010chloro\u20104\u2010[<jats:italic>cyano<\/jats:italic>\u2010<jats:sup>14<\/jats:sup>C]cyanophenoxy)cyclohexyl)\u20106\u2010(4\u2010((4\u2010(2\u2010(2,6\u2010dioxopiperidin\u20103\u2010yl)\u20106\u2010fluoro\u20101,3\u2010dioxoisoindolin\u20105\u2010yl)piperazin\u20101\u2010yl)methyl)piperidin\u20101\u2010yl)pyridazine\u20103\u2010carboxamide (<jats:sup>14<\/jats:sup>C\u2010ARV\u2010110\u2010<jats:bold>b<\/jats:bold>). The synthesis of <jats:sup>14<\/jats:sup>C\u2010ARV\u2010110\u2010<jats:bold>a<\/jats:bold> was initiated from 1,2\u2010dibromo\u20104,5\u2010difluorobenzene and zinc cyanide\u2010<jats:sup>14<\/jats:sup>C (Zn(<jats:sup>14<\/jats:sup>CN)\u2082), while <jats:sup>14<\/jats:sup>C\u2010ARV\u2010110\u2010<jats:bold>b<\/jats:bold> was prepared from 2\u2010chloro\u20104\u2010fluoro[<jats:italic>cyano<\/jats:italic>\u2010<jats:sup>14<\/jats:sup>C]benzonitrile.<\/jats:p>","DOI":"10.1002\/jlcr.4154","type":"journal-article","created":{"date-parts":[[2025,7,24]],"date-time":"2025-07-24T05:38:33Z","timestamp":1753335513000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis of Two Versions of Carbon\u201014\u2010Labeled ARV\u2010110: An Androgen Receptor PROTAC Degrader for Prostate Cancer"],"prefix":"10.1002","volume":"68","author":[{"given":"Xiang\u2010Sheng","family":"Dai","sequence":"first","affiliation":[{"name":"Institute of Nuclear\u2010Agricultural Science, Key Laboratory of Nuclear Agricultural Sciences of Ministry of Agriculture Zhejiang University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bin","family":"Dong","sequence":"additional","affiliation":[{"name":"Science &amp; Technology Innovation Center, Zhejiang Isotope Technologies Co., Ltd  Hangzhou Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0009-0005-3595-5725","authenticated-orcid":false,"given":"Lei","family":"Xu","sequence":"additional","affiliation":[{"name":"Institute of Nuclear\u2010Agricultural Science, Key Laboratory of Nuclear Agricultural Sciences of Ministry of Agriculture Zhejiang University  Hangzhou China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zheng\u2010Min","family":"Yang","sequence":"additional","affiliation":[{"name":"Science &amp; Technology Innovation Center, Zhejiang Isotope Technologies Co., Ltd  Hangzhou Zhejiang Province China"},{"name":"Zhejiang Isotope Labeled Compounds Co., Ltd  Jiaxing Zhejiang Province China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,7,23]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1200\/JCO.2019.37.7_suppl.259"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/bies.201700247"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1146\/annurev\u2010cancerbio\u2010030617\u2010050430"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201507978"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aab1433"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1038\/nature14610"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aal3755"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.2928"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2008.08.095"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2009.03.028"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.scitotenv.2010.02.006"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3085"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.2174\/1381612003399941"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2007.02.018"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3646"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/B978-0-12-382161-4.00003-0"}],"container-title":["Journal of Labelled Compounds and Radiopharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.4154","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T19:22:21Z","timestamp":1760642541000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jlcr.4154"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7]]},"references-count":16,"journal-issue":{"issue":"9-10","published-print":{"date-parts":[[2025,7]]}},"alternative-id":["10.1002\/jlcr.4154"],"URL":"https:\/\/doi.org\/10.1002\/jlcr.4154","archive":["Portico"],"relation":{},"ISSN":["0362-4803","1099-1344"],"issn-type":[{"value":"0362-4803","type":"print"},{"value":"1099-1344","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,7]]},"assertion":[{"value":"2025-04-12","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-08","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-07-23","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e4154"}}