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Issue 8, 2018
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Rosamine with pyronine-pyridinium skeleton: unique mitochondrial targetable structure for fluorescent probes

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Abstract

Two rosamine-based probes (1a–b) with pyronine-pyridinium skeleton were designed and prepared. Probe 1a bearing boron ester unit was oxidized and eliminated upon addition of hydrogen peroxide (H2O2), and the emission spectrum exhibited OFF–ON response accompanied by 33-fold fluorescent enhancement. In contrast, the fluorescence intensity of probe 1b enhanced 58 times after the dinitrophenyl ether part within the probe was removed by nucleophilic substitution with hydrosulfide (H2S). The design concept was based on the d-PET process in pyronine-pyridinium structures, and free 4-pyridinyl-substituted pyronine dye showing strong fluorescence was released followed by elimination. Furthermore, as biocompatible molecules, probes 1a–b have been successfully applied for imaging in live HeLa and Ges-1 cells, and all of them can serve as mitochondrial targetable probes in red channel for detecting independent species.

Graphical abstract: Rosamine with pyronine-pyridinium skeleton: unique mitochondrial targetable structure for fluorescent probes

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Publication details

The article was received on 18 Dec 2017, accepted on 26 Feb 2018 and first published on 27 Feb 2018


Article type: Paper
DOI: 10.1039/C7AN02041D
Citation: Analyst, 2018,143, 1813-1819
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    Rosamine with pyronine-pyridinium skeleton: unique mitochondrial targetable structure for fluorescent probes

    L. Yang, J. Niu, R. Sun, Y. Xu and J. Ge, Analyst, 2018, 143, 1813
    DOI: 10.1039/C7AN02041D

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