{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T02:51:20Z","timestamp":1790823080978,"version":"4.1.0"},"reference-count":68,"publisher":"MDPI AG","issue":"2","license":[{"start":{"date-parts":[[2022,1,28]],"date-time":"2022-01-28T00:00:00Z","timestamp":1643328000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Pharmaceuticals"],"abstract":"<jats:p>The use of radiolabeled non-natural amino acids can provide high contrast SPECT\/PET metabolic imaging of solid tumors. Among them, radiohalogenated tyrosine analogs (i.e., [123I]IMT, [18F]FET, [18F]FDOPA, [123I]8-iodo-L-TIC(OH), etc.) are of particular interest. While radioiodinated derivatives, such as [123I]IMT, are easily available via electrophilic aromatic substitutions, the production of radiofluorinated aryl tyrosine analogs was a long-standing challenge for radiochemists before the development of innovative radiofluorination processes using arylboronate, arylstannane or iodoniums salts as precursors. Surprisingly, despite these methodological advances, no radiofluorinated analogs have been reported for [123I]8-iodo-L-TIC(OH), a very promising radiotracer for SPECT imaging of prostatic tumors. This work describes a convenient synthetic pathway to obtain new radioiodinated and radiofluorinated derivatives of TIC(OH), as well as their non-radiolabeled counterparts. Using organotin compounds as key intermediates, [125I]5-iodo-L-TIC(OH), [125I]6-iodo-L-TIC(OH) and [125I]8-iodo-L-TIC(OH) were efficiently prepared with good radiochemical yield (RCY, 51\u201378%), high radiochemical purity (RCP, &gt;98%), molar activity (Am, &gt;1.5\u20132.9 GBq\/\u00b5mol) and enantiomeric excess (e.e. &gt;99%). The corresponding [18F]fluoro-L-TIC(OH) derivatives were also successfully obtained by radiofluorination of the organotin precursors in the presence of tetrakis(pyridine)copper(II) triflate and nucleophilic [18F]F\u2212 with 19\u201328% RCY d.c., high RCP (&gt;98.9%), Am (20\u2013107 GBq\/\u00b5mol) and e.e. (&gt;99%).<\/jats:p>","DOI":"10.3390\/ph15020162","type":"journal-article","created":{"date-parts":[[2022,1,29]],"date-time":"2022-01-29T05:26:17Z","timestamp":1643433977000},"page":"162","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["A Convenient Route to New (Radio)Fluorinated and (Radio)Iodinated Cyclic Tyrosine Analogs"],"prefix":"10.3390","volume":"15","author":[{"given":"Maria","family":"Chao","sequence":"first","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7162-8450","authenticated-orcid":false,"given":"Jean-Michel","family":"Chezal","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Eric","family":"Debiton","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Damien","family":"Canitrot","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tiffany","family":"Witkowski","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Sophie","family":"Levesque","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"},{"name":"Department of Nuclear Medicine, Jean Perrin Comprehensive Cancer Centre, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0206-3350","authenticated-orcid":false,"given":"Fran\u00e7oise","family":"Degoul","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"S\u00e9bastien","family":"Tarrit","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7390-3575","authenticated-orcid":false,"given":"Barbara","family":"Wenzel","sequence":"additional","affiliation":[{"name":"Helmholtz-Zentrum Dresden-Rossendorf, Research Site Leipzig, Institute of Radiopharmaceutical Cancer Research, 04318 Leipzig, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Elisabeth","family":"Miot-Noirault","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Audrey","family":"Serre","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Aur\u00e9lie","family":"Maisonial-Besset","sequence":"additional","affiliation":[{"name":"Inserm, Imagerie Mol\u00e9culaire et Strat\u00e9gies Th\u00e9ranostiques, UMR 1240, Universit\u00e9 Clermont Auvergne, F-63000 Clermont-Ferrand, France"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"223S","DOI":"10.3945\/ajcn.113.070086","article-title":"Role of Amino Acid Transporters in Amino Acid Sensing","volume":"99","author":"Taylor","year":"2014","journal-title":"Am. 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