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Issue 12, 2017
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In situ formation of pyronin dyes for fluorescence protease sensing

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Abstract

We report a reaction-based strategy for the fluorogenic detection of protease activity. Based on the “covalent-assembly” probe design principle recently put forward by the Yang group for detection of Sarin related threats (J. Am. Chem. Soc., 2014, 136, 6594–6597), we have designed two unusual non-fluorescent caged precursors (mixed bis-aryl ethers) which are readily converted into a fluorescent unsymmetrical pyronin dye through a domino cyclisation–aromatisation reaction triggered by penicillin G acylase (PGA) or leucine aminopeptidase (LAP). Fluorescence-based in vitro assays and HPLC-fluorescence/-MS analyses support the claimed activation mechanism whose the further implementation to “smart” imaging agents for the study of protease function in vivo is expected.

Graphical abstract: In situ formation of pyronin dyes for fluorescence protease sensing

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Publication details

The article was received on 15 Feb 2017, accepted on 28 Feb 2017 and first published on 28 Feb 2017


Article type: Paper
DOI: 10.1039/C7OB00370F
Citation: Org. Biomol. Chem., 2017,15, 2575-2584
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    In situ formation of pyronin dyes for fluorescence protease sensing

    S. Debieu and A. Romieu, Org. Biomol. Chem., 2017, 15, 2575
    DOI: 10.1039/C7OB00370F

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