{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,8]],"date-time":"2026-06-08T19:37:09Z","timestamp":1780947429239,"version":"3.54.1"},"reference-count":25,"publisher":"Wiley","issue":"3","license":[{"start":{"date-parts":[[2023,3,1]],"date-time":"2023-03-01T00:00:00Z","timestamp":1677628800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["17K10383"],"award-info":[{"award-number":["17K10383"]}],"id":[{"id":"10.13039\/501100001691","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":[[2023,3]]},"abstract":"<jats:p>CuI\u2010mediated <jats:sup>11<\/jats:sup>C\u2010cyanation was evaluated by synthesizing [<jats:sup>11<\/jats:sup>C]perampanel ([<jats:sup>11<\/jats:sup>C]<jats:bold>5<\/jats:bold>) as a model compound and compared with previous reports. To a DMF solution with 5\u2032\u2010(2\u2010bromophenyl)\u20101\u2032\u2010phenyl\u2010[2,3\u2032\u2010bipyridin]\u20106\u2032(1\u2032H)\u2010one (<jats:bold>4<\/jats:bold>) and CuI, [<jats:sup>11<\/jats:sup>C]NH<jats:sub>4<\/jats:sub>CN in a stream of ammonia\/nitrogen (5:95, v\/v) gas was bubbled. Subsequently, the reaction mixture was heated at 180\u00b0C for 5\u00a0min. After HPLC purification, [<jats:sup>11<\/jats:sup>C]<jats:bold>5<\/jats:bold> was obtained in 7.2\u2009\u00b1\u20091.0% (<jats:italic>n<\/jats:italic>\u2009=\u20094) non\u2010decay corrected radiochemical yield with &gt;99% radiochemical purity and a molar activity of 98\u2009\u00b1\u200928\u2009GBq\/\u03bcmol. In vivo evaluations of [<jats:sup>11<\/jats:sup>C]<jats:bold>5<\/jats:bold> were performed using small animals. PET scans to check the kinetics of [<jats:sup>11<\/jats:sup>C]<jats:bold>5<\/jats:bold> in the whole body of mice suggested that [<jats:sup>11<\/jats:sup>C]<jats:bold>5<\/jats:bold> spreads rapidly into the brain, heart, and lungs and then accumulates in the small intestine. To evaluate the performance of CuI\u2010mediated <jats:sup>11<\/jats:sup>C\u2010cyanation reaction, bromobenzene (<jats:bold>6a<\/jats:bold>) was selected as the model compound; however, it failed. Therefore, optimization of the reaction conditions has been performed, and consequently, the addition of K<jats:sub>2<\/jats:sub>CO<jats:sub>3<\/jats:sub> and prolonging the reaction time improved the radiochemical yield about double. With this improved method, CuI\u2010mediated <jats:sup>11<\/jats:sup>C\u2010cyanation of various (hetero)aromatic bromides was performed to exhibit the tolerance of most functional groups and to provide <jats:sup>11<\/jats:sup>C\u2010cyanated products in good to moderate radiochemical yields.<\/jats:p>","DOI":"10.1002\/jlcr.4016","type":"journal-article","created":{"date-parts":[[2023,2,15]],"date-time":"2023-02-15T18:23:41Z","timestamp":1676485421000},"page":"95-107","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Evaluation and improvement of CuI\u2010mediated <sup>11<\/sup>C\u2010cyanation"],"prefix":"10.1002","volume":"66","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2408-4897","authenticated-orcid":false,"given":"Hideki","family":"Ishii","sequence":"first","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tomoteru","family":"Yamasaki","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7117-6917","authenticated-orcid":false,"given":"Toshimitsu","family":"Okamura","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yiding","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yusuke","family":"Kurihara","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"},{"name":"SHI Accelerator Service Ltd.  Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Masanao","family":"Ogawa","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"},{"name":"SHI Accelerator Service Ltd.  Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Nobuki","family":"Nengaki","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"},{"name":"SHI Accelerator Service Ltd.  Tokyo Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ming\u2010Rong","family":"Zhang","sequence":"additional","affiliation":[{"name":"Department of Advanced Nuclear Medicine Sciences, Institute for Quantum Medical Science National Institutes for Quantum Science and Technology  Chiba Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2023,3]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr0782426"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.202100651"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1039\/C7CC02886E"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.orglett.8b00242"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/C8OB02049C"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.nucmedbio.2021.09.002"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar00022a001"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/a804370a"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1MD00131K"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/9781118662083"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3540"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jmedchem.5b00712"},{"key":"e_1_2_8_14_1","unstructured":"Products CfHM.International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) Q3D on elemental impurities \u2010 Step 5 \u2010 Revision 1.2019;https:\/\/www.ema.europa.eu\/en\/documents\/scientific-guideline\/international-conference-harmonisation-technical-requirements-registration-pharmaceuticals-human-use_en-32.pdf. Accessed 12th May 2022."},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00259\u2010021\u201005269\u20104"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1093\/braincomms\/fcab011"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/jlcr.3965"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00259\u2010021\u201005235\u20100"},{"key":"e_1_2_8_19_1","unstructured":"EisaiCo. L.Eisai to Present Latest Data on Perampanel and E2730 at the 75th American Epilepsy Society Annual Meeting.2021;https:\/\/www.eisai.com\/news\/2021\/pdf\/enews202194pdf.pdf. Accessed May 17th 2022."},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1038\/srep28649"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1111\/j.1528\u20101167.2011.03109.x"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja512115s"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja104917t"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1002\/psp4.12466"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0299708"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr800270h"}],"container-title":["Journal of Labelled Compounds and Radiopharmaceuticals"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.4016","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/jlcr.4016","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/jlcr.4016","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,16]],"date-time":"2025-10-16T15:40:27Z","timestamp":1760629227000},"score":1,"resource":{"primary":{"URL":"https:\/\/analyticalsciencejournals.onlinelibrary.wiley.com\/doi\/10.1002\/jlcr.4016"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,3]]},"references-count":25,"journal-issue":{"issue":"3","published-print":{"date-parts":[[2023,3]]}},"alternative-id":["10.1002\/jlcr.4016"],"URL":"https:\/\/doi.org\/10.1002\/jlcr.4016","archive":["Portico"],"relation":{},"ISSN":["0362-4803","1099-1344"],"issn-type":[{"value":"0362-4803","type":"print"},{"value":"1099-1344","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,3]]},"assertion":[{"value":"2022-09-15","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-02-11","order":2,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2023-03-01","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}