Article Dans Une Revue Chemistry - A European Journal Année : 2022

211At and 125I‐labeling of (hetero)aryliodonium ylides: astatine wins again

Résumé

Despite the growing interest in radioiodine and 211 At-labeled radiopharmaceuticals, the search for radiolabeling reactions has been somewhat neglected, resulting in a limited number of available radiosynthetic strategies. Herein we report a comparative study of nucleophilic 125 I and 211 At-labeling of aryliodonium ylides. Whereas radioiodination efficiency was low, 211 At-labeling performed efficiently on a broad scope of precursors. The most activated aryliodonium ylides led rapidly to quantitative reactions at room temperature in acetonitrile. For deactivated precursors, heating up to 90 °C in glyme and addition of 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) as radical scavenger appeared essential to avoid precursor degradation and to achieve high radiochemical yields and molar activity. The approach was applied successfully to the preparation of 4-[211 At]astatophenylalanine (4-APA), an amino acid derivative increasingly studied as radiotherapeutic drug for cancers. This validated aryliodonium ylides as a valuable tool for nucleophilic 211 At-labeling and will complement the short but now growing list of available astatination reactions.

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hal-03507646 , version 1 (03-01-2022)

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Clémence Maingueneau, Marion Berdal, Romain Eychenne, Jöelle Gaschet, Michel Chérel, et al.. 211At and 125I‐labeling of (hetero)aryliodonium ylides: astatine wins again. Chemistry - A European Journal, 2022, 28 (11), ⟨10.1002/chem.202104169⟩. ⟨hal-03507646⟩
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