A novel versatile precursor suitable for F-18-radiolabeling via "click chemistry"

作者：Lugato B; Stucchi S; Ciceri S; Iannone M N; Turolla E A; Giuliano L; Chinello C; Todde S; Ferraboschi P^*

来源：Journal of Labelled Compounds and Radiopharmaceuticals, 2017, 60(10): 466-480.

DOI：10.1002/jlcr.3529

• 1,2,3-triazole
• F-18-radiolabeling
• click chemistry
• CuAAc
• L-propargylglycine
• PET

As an effort to improve F-18-radiolabeling of biomolecules in method robustness and versatility, we report the synthesis and radiolabeling of a new azido precursor potentially useful for the so-called click reaction, in particular the ligand-free version of the copper(I)-catalyzed alkyne-azide cycloaddition. The new azido precursor may help to overcome problems sometimes exhibited by most of the currently used analogues, as it is safe to handle and it displays long-term chemical stability, thus facilitating the development of new radiolabeling procedures. Moreover, the formed F-18-labeled 1,2,3-triazole is potentially metabolically stable and could enhance the in vivo circulation time. The above azido precursor was successfully radiolabeled with F-18, with 51% radiochemical yield (nondecay-corrected). As a proof of concept, the F-18-labeled azide was then tested with a suitable alkyne functionalized aminoacid (l-propargylglycine), showing 94% of conversion, and a final radiochemical yield of 27% (>99% radiochemical purity), nondecay-corrected, with a total preparation time of 104minutes.

• 出版日期2017-8