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2017•Angewandte ChemieRequires access

Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes

Sabrina Bernard, Davide Audisio, Margaux Riomet, Sarah Bregant, Antoine Sallustrau, Lucie Plougastel, Elodie Decuypère, Sandra Gabillet, R. Arun Kumar, Jijy Elyian, Minh Nguyet Trinh, Oleksandr Koniev, Alain Wagner, Sergii Kolodych, Frédéric Taran

Open publisher page 41 citations

Abstract

Abstract We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

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Abstract We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

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Available abstract

Abstract We report the discovery of a new bioorthogonal click‐and‐release reaction involving iminosydnones and strained alkynes. This transformation leads to two products resulting from the ligation and fragmentation of iminosydnones under physiological conditions. Optimized iminosydnones were successfully used to design innovative cleavable linkers for protein modification, thus opening up new areas in the fields of drug release and target‐fishing applications. This click‐and‐release technology offers the possibility of exchanging tags on proteins for functionalized cyclooctynes under mild and bioorthogonal conditions.

Key concepts: Bioorthogonal chemistry, Click chemistry, Chemistry, Combinatorial chemistry, Bioconjugation, Nanotechnology, Materials science

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