{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,19]],"date-time":"2025-10-19T06:07:04Z","timestamp":1760854024303,"version":"build-2065373602"},"reference-count":18,"publisher":"Wiley","issue":"14","license":[{"start":{"date-parts":[[2018,11,4]],"date-time":"2018-11-04T00:00:00Z","timestamp":1541289600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000065","name":"National Institute of Neurological Disorders and Stroke","doi-asserted-by":"publisher","award":["U01NS092495"],"award-info":[{"award-number":["U01NS092495"]}],"id":[{"id":"10.13039\/100000065","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["analyticalsciencejournals.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Labelled Comp Radiopharmac"],"published-print":{"date-parts":[[2018,12]]},"abstract":"O\u2010(1\u2010Fluoropropan\u20102\u2010yl)\u2010O\u2010(4\u2010nitrophenyl) methylphosphonate is a reactive organophosphate ester (OP) developed as a surrogate of the chemical warfare agent sarin that forms a similar covalent adduct at the active site serine of acetylcholinesterase. The radiolabeled O\u2010(1\u2010[18<\/jats:sup>F]fluoropropan\u20102\u2010yl)\u2010O\u2010(4\u2010nitrophenyl) methylphosphonate ([18<\/jats:sup>F] fluorosarin surrogate) has not been previously prepared. In this paper, we report the first radiosynthesis of this tracer from the reaction of bis<\/jats:italic>\u2010(4\u2010nitrophenyl) methylphosphonate with 1\u2010[18<\/jats:sup>F]fluoro\u20102\u2010propanol in the presence of DBU. The 1\u2010[18<\/jats:sup>F]fluoro\u20102\u2010propanol was prepared by reaction of propylene sulfite with Kryptofix 2.2.2 and [18<\/jats:sup>F] fluoride ion. The desired tracer O\u2010(1\u2010[18<\/jats:sup>F]fluoropropan\u20102\u2010yl)\u2010O\u2010(4\u2010nitrophenyl) methylphosphonate was obtained in a >98% radiochemical purity with a 2.4%\u00a0\u00b1\u00a00.6% yield (n\u00a0=\u00a05, 65\u00a0minutes from start of synthesis) based on starting [18<\/jats:sup>F] fluoride ion and a molar activity of 49.9\u00a0GBq\/\u03bcmol (1.349\u00a0\u00b1\u00a00.329\u00a0Ci\/\u03bcmol, n\u00a0=\u00a03). This new facile radiosynthesis routinely affords sufficient quantities of [18<\/jats:sup>F] fluorosarin surrogate in high radiochemical purity, which will further enable the tracer development as a novel radiolabeled OP acetylcholinesterase inhibitor for assessment of OP modes of action with PET imaging in vivo.<\/jats:p>","DOI":"10.1002\/jlcr.3688","type":"journal-article","created":{"date-parts":[[2018,10,22]],"date-time":"2018-10-22T18:10:46Z","timestamp":1540231846000},"page":"1089-1094","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Radiosynthesis of O\u2010(1\u2010[18<\/sup>F]fluoropropan\u20102\u2010yl)\u2010O\u2010(4\u2010nitrophenyl)methylphosphonate: A novel PET tracer surrogate of sarin"],"prefix":"10.1002","volume":"61","author":[{"given":"Thomas R.","family":"Hayes","sequence":"first","affiliation":[{"name":"Department of Radiology and Biomedical Imaging University of California, San Francisco San Francisco CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Charles M.","family":"Thompson","sequence":"additional","affiliation":[{"name":"Department of Biomedical and Pharmaceutical Sciences University of Montana Missoula MT USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Joseph E.","family":"Blecha","sequence":"additional","affiliation":[{"name":"Department of Radiology and Biomedical Imaging University of California, San Francisco San Francisco CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"John M.","family":"Gerdes","sequence":"additional","affiliation":[{"name":"Department of Biomedical and Pharmaceutical Sciences University of Montana Missoula MT USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2849-0841","authenticated-orcid":false,"given":"Henry F.","family":"VanBrocklin","sequence":"additional","affiliation":[{"name":"Department of Radiology and Biomedical Imaging University of California, San Francisco San Francisco CA USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,11,4]]},"reference":[{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccc.2005.05.010"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0196-0644(05)81036-4"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0065-2423(04)38006-6"},{"volume-title":"Organophosphorus Pesticides; Organic and Biological Chemistry","year":"1974","author":"Eto M","key":"e_1_2_7_5_1"},{"key":"e_1_2_7_6_1","doi-asserted-by":"crossref","DOI":"10.1007\/978-3-642-97876-0","volume-title":"The Chemistry of Organophosphorus Pesticides; Reactivity, Synthesis, Mode of Action, Toxicology","author":"Fest C","year":"1973"},{"key":"e_1_2_7_7_1","first-page":"161","volume-title":"Goodman & Gilman's the Pharmacological Basis of Therapeutics","author":"Taylor P","year":"1996"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.2174\/138955707780619581"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.2174\/1568026611209061775"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1081\/CLT-120015840"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.pharmthera.2013.04.009"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.2174\/0929867033456314"},{"key":"e_1_2_7_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.chemrestox.6b00160"},{"key":"e_1_2_7_14_1","first-page":"323","article-title":"A novel high affinity F\u201018 organophosphonate tracer for CNS acetylcholinesterase","volume":"54","author":"Gerdes JM","year":"2013","journal-title":"J Nucl Med"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/cn500024c"},{"key":"e_1_2_7_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3511"},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cbi.2018.06.019"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-1993-25982"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bmcl.2013.02.010"}],"container-title":["Journal of Labelled Compounds and Radiopharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fjlcr.3688","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.3688","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T15:30:24Z","timestamp":1760628624000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jlcr.3688"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,4]]},"references-count":18,"journal-issue":{"issue":"14","published-print":{"date-parts":[[2018,12]]}},"alternative-id":["10.1002\/jlcr.3688"],"URL":"https:\/\/doi.org\/10.1002\/jlcr.3688","archive":["Portico"],"relation":{},"ISSN":["0362-4803","1099-1344"],"issn-type":[{"type":"print","value":"0362-4803"},{"type":"electronic","value":"1099-1344"}],"subject":[],"published":{"date-parts":[[2018,11,4]]},"assertion":[{"value":"2018-07-18","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-10-15","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2018-11-04","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}