In this report we describe the development of an alternative approach to arylstannane chemistry for radiolabeling antibodies with radioiodine or astatine based on aryliodonium salts precursors. Bifunctional aryliodonium salts were designed and tested for the synthesis of ¹²⁵I and ²¹¹At labeled prosthetic groups for bioconjugation. The nature of the electron rich aryl group was varied and its impact on the regioselectivity of radiohalogenation was evaluated. Unexpectedly, whereas the 2-thienyl group provided the best regioselectivity towards the radioiodination of the aryl moiety of interest (98:2), it was less selective for astatination (87:13); the anisyl group providing the best regioselectivity of astatination (94:6). Under optimized conditions, both radioiodination and astatination could be performed very efficiently in mild conditions (radiochemical yields > 85%). The ionic nature of the precursors was exploited to develop an efficient purification approach: the HPLC step that is usually necessary in conventionnal approaches to optimize removal of organotin toxic precursors and side products was replaced by a filtration through a silica cartridge with a significantly reduced loss of radiolabeled product. The purified radioiodinated and astatinated prosthetic groups were then conjugated efficiently to an anti-CD138 monoclonal antibody (75–80% conjugation yield). By using this novel and simple radiohalogenation procedure, higher overall radiochemical yields of astatination were obtained in comparison with the use of an arylstannane precursor and procedures of the litterature for labeling the same antibody. Overall, due to their simplicity of use and high robustness, these new precursors should simplify the labeling of proteins of interest with iodine and astatine radioisotopes for imaging and therapeutic applications.

在本报告中，我们描述了一种基于芳基碘盐前体的，用放射性碘或antibodies标记放射性标记抗体的芳基锡烷化学替代方法的开发。设计并测试了双功能芳基碘鎓盐用于¹²⁵ I和²¹¹的合成在标记的修复基团上进行生物偶联。改变富电子芳基的性质，并评估其对放射性卤代区域选择性的影响。出乎意料的是，尽管2-噻吩基对感兴趣的芳基部分的放射性碘化具有最佳的区域选择性（98：2），但其对stat化的选择性较低（87:13）；茴香基提供了最佳的stat灭区域选择性（94：6）。在优化的条件下，在温和条件下（放射化学收率> 85％）可以非常有效地进行放射性碘化和静止化。利用前体的离子性质来开发有效的纯化方法：常规方法中通常需要的HPLC步骤，以优化去除有机锡有毒前体和副产物的方法，是通过硅胶滤筒进行过滤，而放射性标记产物的损失明显减少，从而代替了该步骤。然后将纯化的放射性碘化和a化的修复基团有效地偶联至抗CD138单克隆抗体（结合率达75–80％）。通过使用这种新颖且简单的放射性卤化方法，与使用芳基锡烷前体和标记相同抗体的文献法相比，可以获得更高的总体overall化放射化学产率。总体而言，由于其使用简单且坚固耐用，