N-Heterocyclic Carbenes as Ligands to (198)Au(I)-Radiolabeled Compounds: A New Platform for Radiopharmaceutical Design

N-杂环卡宾作为(198)Au(I)放射性标记化合物的配体:放射性药物设计的新平台

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Abstract

The radionuclide (198)Au, with a half-life of 2.7 days, emits γ radiation ideal for diagnostic purposes and generates β(-) particles suitable for effective cancer radiotherapy, making it a perfect nuclide for "theranostics". However, the application of coordination compounds of Au(I)/Au(III) in medicine is limited by their instability in vivo. Here, we explore N-heterocyclic carbene (NHC) organometallic chemistry to stabilize (198)Au(I) in radiopharmaceuticals. Thus, Au(I) NHC compounds featuring different scaffolds were selected for (198)Au radiolabeling. Eventually, two compounds featuring imidazole (AuNHC-1) and theophylline (AuTMX(2)) scaffolds were successfully radiolabeled (radiochemical purity = 92.9% and 40.2%, respectively). Instead, two peptidic Au(I) benzimidazolylidene derivatives, capable of blood-brain barrier translocation in vitro, were subjected to ligand exchange reactions under the applied radiolabeling conditions. The obtained proof-of-concept results showed that NHCs are suitable ligands to achieve isotope exchange in Au(I) complexes. Overall, our work reveals the still untapped potential of organometallic chemistry in radiopharmaceutical design.

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