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Issue 11, 2017
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Intramolecular substitution uncages fluorogenic probes for detection of metallo-carbapenemase-expressing bacteria

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Abstract

This work reports a novel caging strategy for designing fluorogenic probes to detect the activity of β-lactamases. The caging strategy uses a thiophenyl linker connected to a fluorophore caged by a good leaving group—dinitrophenyl. The uncaging proceeds in two steps through the sulfa-releasing and subsequent intramolecular substitution. The length of the linker has been examined and optimized to maximize the rate of intramolecular reaction and thus the rate of fluorescence activation. Finally based on this strategy, we prepared a green fluorogenic probe CAT-7 and validated its selectivity for detecting metallo-carbapenemases (VIM-27, IMP-1, NDM-1) in carbapenem-resistant Enterobacteriaceae (CRE) lysates.

Graphical abstract: Intramolecular substitution uncages fluorogenic probes for detection of metallo-carbapenemase-expressing bacteria

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Publication details

The article was received on 29 May 2017, accepted on 21 Sep 2017 and first published on 21 Sep 2017


Article type: Edge Article
DOI: 10.1039/C7SC02416A
Citation: Chem. Sci., 2017,8, 7669-7674
  • Open access: Creative Commons BY-NC license
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    Intramolecular substitution uncages fluorogenic probes for detection of metallo-carbapenemase-expressing bacteria

    A. Song, Y. Cheng, J. Xie, N. Banaei and J. Rao, Chem. Sci., 2017, 8, 7669
    DOI: 10.1039/C7SC02416A

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