Sydnone-based prosthetic groups for radioiodination

IF 3.3 3区 医学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioorganic & Medicinal Chemistry Pub Date : 2024-09-03 DOI:10.1016/j.bmc.2024.117904
Ludovic Le Saux , Ferid Haddad , Jean-François Gestin , Romain Eychenne , François Guérard
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Abstract

The potential of Strained-Promoted Sydnone-Alkyne Cycloaddition (SPSAC) for radioiodination was evaluated with model cyclooctyne-conjugated peptides. Starting with a series of sydnones with varying N3 and C4 substitution, a preliminary kinetic study with non-radioactive iodinated compounds highlighted the superiority of an arylsydnone substituted by a chlorine atom in C4 position. Interestingly, reaction rate up to 11 times higher than using an azide was achieved with the best system. Access to 125I-labelled sydnones was granted with high efficiency from arylboronic acid precursors by copper catalyzed nucleophilic substitution. Application of SPSAC on the model peptide in radiotracer conditions showed the same trend than in non-radioactive kinetic study and complete reactions could be achieved within less than an hour for the best systems. These results are favorable for use in the production of radiopharmaceuticals with heavy halogens and increase the diversity of available bioorthogonal reaction for nuclear imaging and therapy.

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基于西地那非的放射碘化修复基团
我们利用环辛炔共轭肽模型评估了应变促进昔多酮-醇炔环加成法(SPSAC)在放射性碘化方面的潜力。从一系列具有不同 N3 和 C4 取代度的茜酮开始,对非放射性碘化化合物进行了初步动力学研究,结果表明在 C4 位被一个氯原子取代的芳基茜酮具有优越性。有趣的是,最佳体系的反应速率比叠氮化物高出 11 倍。通过铜催化的亲核取代反应,从芳基硼酸前体中高效地获得了 125I 标记的sydnones。在放射性示踪剂条件下,将 SPSAC 应用于模型肽显示出与非放射性动力学研究相同的趋势,最佳体系可在不到一小时内完成反应。这些结果有利于使用重卤素生产放射性药物,并增加了用于核成像和治疗的生物正交反应的多样性。
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来源期刊
Bioorganic & Medicinal Chemistry
Bioorganic & Medicinal Chemistry 医学-生化与分子生物学
CiteScore
6.80
自引率
2.90%
发文量
413
审稿时长
17 days
期刊介绍: Bioorganic & Medicinal Chemistry provides an international forum for the publication of full original research papers and critical reviews on molecular interactions in key biological targets such as receptors, channels, enzymes, nucleotides, lipids and saccharides. The aim of the journal is to promote a better understanding at the molecular level of life processes, and living organisms, as well as the interaction of these with chemical agents. A special feature will be that colour illustrations will be reproduced at no charge to the author, provided that the Editor agrees that colour is essential to the information content of the illustration in question.
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