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A Convenient Route to New (Radio)Fluorinated and (Radio)Iodinated Cyclic Tyrosine Analogs

Authors :
Croce, Sabrina
Devouassoux-Shisheboran, Mojgan
Pautier, Patricia
Ray-Coquard, Isabelle
Treilleux, Isabelle
Neuville, Agnès
Arnould, Laurent
Just, Pierre-Alexandre
Belda, Marie Aude Le Frere
Averous, Gerlinde
Leroux, Agnès
Mery, Eliane
Loussouarn, Delphine
Weinbreck, Nicolas
Le Guellec, Sophie
Mishellany, Florence
Morice, Philippe
Guyon, Frédéric
Genestie, Catherine
Imagerie Moléculaire et Stratégies Théranostiques (IMoST)
Institut National de la Santé et de la Recherche Médicale (INSERM)-Université Clermont Auvergne (UCA)
Source :
Pharmaceuticals; Volume 15; Issue 2; Pages: 162, Pharmaceuticals, Pharmaceuticals, 2022, 15 (2), pp.162. ⟨10.3390/ph15020162⟩
Publication Year :
2021

Abstract

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, 51–78%), high radiochemical purity (RCP, >98%), molar activity (Am, >1.5–2.9 GBq/µmol) and enantiomeric excess (e.e. >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− with 19–28% RCY d.c., high RCP (>98.9%), Am (20–107 GBq/µmol) and e.e. (>99%).

Details

ISSN :
14248247
Volume :
15
Issue :
2
Database :
OpenAIRE
Journal :
Pharmaceuticals (Basel, Switzerland)
Accession number :
edsair.doi.dedup.....309d2865cc29f5642ef5fe93ad6bac37