Synthesis of sydnonimines from sydnones and their use for bioorthogonal release of isocyanates in cells.

In this article, we report the synthesis of sydnonimines from sydnones and their use as dipoles for fast click-and-release reactions. The process relies on nucleophilic aromatic substitution of aliphatic and aromatic amines with triflated sydnones. This new methodology allowed the preparation of functionalised sydnonimine probes that are otherwise difficult to prepare. These probes were then used to release a drug and a fluorescent aromatic isocyanate inside living cells.

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Judith Baudet, Emilie Lesur, Maxime Ribéraud, Arnaud Chevalier, Timothée D'Anfray, Pierre Thuéry, Davide Audisio, Frédéric Taran. Synthesis of sydnonimines from sydnones and their use for bioorthogonal release of isocyanates in cells. Chemical communications (Cambridge, England). 2024 Mar 28;60(27):3657-3660

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PMID: 38451232

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