Bioorthogonal Click and Release Reaction of Iminosydnones with Cycloalkynes.
Fiche publication
Date publication
décembre 2017
Journal
Angewandte Chemie (International ed. in English)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr WAGNER Alain, Dr KOLODYCH Sergii, Dr KONIEV Sasha
Tous les auteurs :
Bernard S, Audisio D, Riomet M, Bregant S, Sallustrau A, Plougastel L, Decuypere E, Gabillet S, Kumar RA, Elyian J, Trinh MN, Koniev O, Wagner A, Kolodych S, Taran F
Lien Pubmed
Résumé
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.
Mots clés
bioorthogonal reactions, chemical biology, cleavage reactions, click chemistry, mesoionic compounds
Référence
Angew. Chem. Int. Ed. Engl.. 2017 Dec 4;56(49):15612-15616