Copper-mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide
Copper-mediated radioiodination reaction through aryl boronic acid or ester precursor and its application to direct radiolabeling of a cyclic peptide
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DOI：
10.1002/jlcr.3925
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发表时间：
2021-05-24
影响因子：
1.8
通讯作者：
Yasui, Hiroyuki
中科院分区：
文献类型：
--
作者：
Kondo, Yuto;Kimura, Hiroyuki;Yasui, Hiroyuki
使用芳基硼酸前体的铜介导的放射性碘化作为氧化性碘脱锡和镍介导的放射性碘化缺点的解决方案而引起关注。铜介导的放射性标记方法允许在室温下用稳定的芳基硼酸前体进行放射性碘化，而无需制备复杂的起始材料或试剂，并且可以在暴露于空气的反应容器中进行。该方法在放射化学中具有很好的应用前景，但目前对含硼前体铜介导的放射性碘化反应的研究还不够。特别是，很少有报道表明保护基团对放射性标记效率的影响。因此，研究了芳基硼酸保护基对铜介导的放射性碘标记反应的影响。此外，该方法不需要加热，预期可用于肽的直接放射性标记。因此，我们尝试了c（RGDyk）的直接放射性碘化作为例子。所得的放射性碘化方法在各种底物中耐受良好，并且不受频哪醇酯型保护基的影响。此外，c（RGDyk）通过使用芳基硼酸前体的铜介导的放射性碘化用I-125标记。与间接法相比，反应时间和收率均有所提高。此外，硼酸前体和放射性标记的化合物之间的极性差异很大，有利于纯化。
A copper-mediated radioiodination using aryl boronic precursors is attracting attention as a solution to oxidative iododestannylation and nickel-mediated radioiodination drawbacks. The copper-mediated radiolabeling method allows radioiodination at room temperature with stable aryl boronic precursors without preparing complex starting materials or reagents and can be performed in a reaction vessel exposed to air. This method has good potential in radiochemistry; however, studies on the scope of copper-mediated radioiodination through boronic precursors are insufficient. In particular, few reports have demonstrated the effect of protecting groups on radiolabeling efficiency. Therefore, the effect of the protecting group of aryl boronic acids on the copper-mediated radioiodination was investigated. In addition, this method, which does not require heating, is expected to be useful for direct radiolabeling of peptides. Thus, we attempted direct radioiodination of c(RGDyk) as an example. The resulting radioiodination method was well tolerated in various substrates and was unaffected by the pinacol ester-type protecting group. Also, c(RGDyk) was labeled with I-125 via copper-mediated radioiodination using an aryl boronic acid precursor. The reaction time and yield were improved, compared with the indirect method. Furthermore, the large difference in polarity between the boronic acid precursor and the radiolabeled compound facilitated purification.