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

التفاصيل البيبلوغرافية
العنوان: A Convenient Route to New (Radio)Fluorinated and (Radio)Iodinated Cyclic Tyrosine Analogs
المؤلفون: Maria Noelia Chao, Jean-Michel Chezal, Eric Debiton, Damien Canitrot, Tiffany Witkowski, Sophie Levesque, Françoise Degoul, Sébastien Tarrit, Barbara Wenzel, Elisabeth Miot-Noirault, Audrey Serre, Aurélie Maisonial-Besset
المصدر: Pharmaceuticals, Vol 15, Iss 2, p 162 (2022)
بيانات النشر: MDPI AG, 2022.
سنة النشر: 2022
المجموعة: LCC:Medicine
LCC:Pharmacy and materia medica
مصطلحات موضوعية: radioiodination, radiofluorination, tyrosine analogs, TIC(OH), PET/SPECT imaging, Medicine, Pharmacy and materia medica, RS1-441
الوصف: 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%).
نوع الوثيقة: article
وصف الملف: electronic resource
اللغة: English
تدمد: 1424-8247
Relation: https://www.mdpi.com/1424-8247/15/2/162; https://doaj.org/toc/1424-8247
DOI: 10.3390/ph15020162
URL الوصول: https://doaj.org/article/939943005baa4438ab347be942640403
رقم الأكسشن: edsdoj.939943005baa4438ab347be942640403
قاعدة البيانات: Directory of Open Access Journals
الوصف
تدمد:14248247
DOI:10.3390/ph15020162