Catalyst-free thia-Diels-Alder click reaction for the labeling of peptides for imaging applications

IF 1.4 4区化学 Q4 CHEMISTRY, INORGANIC & NUCLEAR

Phosphorus, Sulfur, and Silicon and the Related Elements Pub Date : 2023-01-01 DOI:10.1080/10426507.2023.2165659

Timothé Maujean , Patrice Marchand , Patrick Wagner , Stéphanie Riché , Frédéric Boisson , Nicolas Girard , Julie Karpenko , Dominique Bonnet , Mihaela Gulea

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Abstract

A thia-Diels-Alder reaction between a phosphonodithioester and a highly reactive exocyclic diene for the chemoselective labeling of peptides under catalyst-free mild conditions is described. An efficient method to introduce the dithioester function into a model tripeptide was first developed and then applied to two bioactive peptides, PSMA and apelin-13. The tripeptide-dithioester was used to optimize the cycloaddition with dienes bearing fluorine-18 or a fluorophore. Then, the cycloaddition of the PSMA-dithioester with the ¹⁸F-diene led to a new PSMA-radiotracer, which was used for in vivo Positron Emission Tomography (PET) imaging. In the same way, a fluorescent apelin-13 probe was obtained from the apelin-dithioester and a squaraine-linked diene before beingused for in cellulo optical imaging.

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无催化剂的thia-Diels-Alder点击反应用于成像应用的肽标记

在无催化剂的温和条件下，描述了磷酸二硫酯和高活性外环二烯之间的硫-迪尔斯-阿尔德反应，用于肽的化学选择性标记。首先建立了一种将二硫酯功能引入模型三肽的有效方法，然后将其应用于两种生物活性肽PSMA和apelin-13。用三肽二硫酯优化了含氟-18或含氟基团的二烯的环加成反应。然后，psma -二硫酯与18f -二烯的环加成得到一种新的psma放射性示踪剂，该示踪剂用于体内正电子发射断层扫描(PET)成像。以同样的方式，在用于纤维素光学成像之前，从飞尾蛋白二硫酯和方烷连接的二烯中获得荧光飞尾蛋白13探针。

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来源期刊

Phosphorus, Sulfur, and Silicon and the Related Elements 化学-无机化学与核化学

CiteScore

2.60

自引率

7.70%

发文量

103

审稿时长

2.1 months

期刊介绍： Phosphorus, Sulfur, and Silicon and the Related Elements is a monthly publication intended to disseminate current trends and novel methods to those working in the broad and interdisciplinary field of heteroatom chemistry.