Sydnone-based prosthetic groups for radioiodination - Inserm - Institut national de la santé et de la recherche médicale
Article Dans Une Revue Bioorganic and Medicinal Chemistry Année : 2024

Sydnone-based prosthetic groups for radioiodination

Résumé

The potential of Strained-Promoted Sydnone-Alkyne Cycloaddition (SPSAC) for radioiodination was evaluated with model cyclooctyne-conjugated peptides. Starting with a series of sydnones with varying N 3 and C 4 substitution, a preliminary kinetic study with nonradioactive iodinated compounds highlighted the superiority of an arylsydnone substituted by a chlorine atom in C 4 position. Interestingly, reaction rate up to 11 times higher than using an azide was achieved with the best system. Access to 125 I-labelled sydnones was granted with high efficiency from arylboronic acid precursors by copper catalyzed nucleophilic substitution. Application of SPSAC on the model peptide in radiotracer conditions showed the same trend than in non-radioactive kinetic study and complete reactions could be achieved within less than an hour for the best systems. These results are favorable for use in the production of radiopharmaceuticals with heavy halogens and increase the diversity of available bioorthogonal reaction for nuclear imaging and therapy.
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Dates et versions

inserm-04688208 , version 1 (04-09-2024)
inserm-04688208 , version 2 (12-09-2024)

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Ludovic Le Saux, Ferid Haddad, Jean-François Gestin, Romain Eychenne, François Guérard. Sydnone-based prosthetic groups for radioiodination. Bioorganic and Medicinal Chemistry, 2024, 113, pp.117904. ⟨10.1016/j.bmc.2024.117904⟩. ⟨inserm-04688208v2⟩
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