Kinetics improvement of protease-mediated formation of pyronin dyes. Issue 20 (16th May 2018)

• Record Type: Journal Article
• Authors: Debieu, Sylvain; Romieu, Anthony
• Is Part Of: Tetrahedron letters. Volume 59:Issue 20(2018)
• Page Start: 1940
• Page End: 1944
• Publication Date: 2018-05-16
• Subjects: Biocompatible reaction -- Covalent assembly -- Fluorescent probe -- Protease -- Pyronin -- Xanthene dyes; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2018.04.010
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A novel "covalent-assembly" type fluorogenic probe for detection of proteases. The probe also acts as a red-emissive fluorophore with AIE characteristics. The dicyanomethylidenyl moiety enables to obtain fast kinetics of pyronin formation. 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 ether2 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 ).