As an effort to improve 18F-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 18F-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 18F, with 51% radiochemical yield (nondecay-corrected). As a proof of concept, the 18F-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 104 minutes.

Lugato, B., Stucchi, S., Ciceri, S., Iannone, M., Turolla, E., Giuliano, L., et al. (2017). A novel versatile precursor suitable for 18F-radiolabeling via “click chemistry”. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 60(10), 466-480 [10.1002/jlcr.3529].

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

Lugato, B.;Iannone, M. N.;Turolla, E. A.;Giuliano, L.;Chinello, C.;Todde, S.;
2017

Abstract

As an effort to improve 18F-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 18F-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 18F, with 51% radiochemical yield (nondecay-corrected). As a proof of concept, the 18F-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 104 minutes.
Articolo in rivista - Articolo scientifico
18; F-radiolabeling; 1,2,3-triazole; click chemistry; CuAAc; l-propargylglycine; PET;
18F-radiolabeling; 1,2,3-triazole; click chemistry; CuAAc; l-propargylglycine; PET
English
2017
2017
60
10
466
480
reserved
Lugato, B., Stucchi, S., Ciceri, S., Iannone, M., Turolla, E., Giuliano, L., et al. (2017). A novel versatile precursor suitable for 18F-radiolabeling via “click chemistry”. JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 60(10), 466-480 [10.1002/jlcr.3529].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10281/183825
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