Kinetics improvement of protease-mediated formation of pyronin dyes

Abstract : A fluorescent probe for protease sensing and based on the “covalent-assembly” principle is reported. The basic rational for this unusual class of chemodosimeters proposed by the Anslyn and Yang groups entails the synthesis of non-fluorophore caged precursors full-stable and reactive towards the targeted analyte. Unlike the first generation of protease-sensitive “covalent-assembly” type probes recently published by ourselves (Org. Biomol. Chem.2017, 15, 2575–2584), the availability of dicyanomethylidenyl and enzyme-labile phenylacetamide moieties within the core structure of mixed bis-aryl ether 2 enables its rapid conversion into a fluorescent pyronin dye at physiological pH and upon activation with penicillin G acylase (PGA). This is real progress towards the practical implementation of this ingenious activation mechanism to the detection of enzymes in their native environment (in cellulo or in vivo).
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Soumis le : samedi 29 juin 2019 - 15:25:21
Dernière modification le : vendredi 5 juillet 2019 - 07:27:58

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Sylvain Debieu, Anthony Romieu. Kinetics improvement of protease-mediated formation of pyronin dyes. Tetrahedron Letters, Elsevier, 2018, 59 (20), pp.1940 - 1944. ⟨10.1016/j.tetlet.2018.04.010⟩. ⟨hal-01856701⟩

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