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A novel pyrene-based dual multifunctional fluorescent probe for differential sensing of pH and HSO3 and their bioimaging in live cells

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Abstract

We designed and synthesized a new fluorescent probe for detecting pH and HSO3 using pyrene as an electron donor (D) and pyridine as an electron acceptor (A). The fluorescent probe for sensing pH and HSO3 could distinguish these by their spectral properties in different media. pH titrations indicated that the probe displayed a ratiometric emission (pH 7.10–1.36) with a pKa of 4.26, responded linearly to minor pH fluctuations within the acidic pH range of 3.00–5.50 in CH3CN/H2O (1/3, v/v), and exhibited a remarkable emission enhancement (pH 7.10–13.09) with a pKa of 10.91 and a linear response in the extremely alkaline pH range of 9.75–11.35 in CH3CN/H2O (1/19, v/v). Interestingly, the probe also responded to HSO3 with an obvious turn-off fluorescence signal in PBS buffer (pH = 5.00, 1.5% DMSO). This could be attributed to the Michael addition of HSO3 to the α,β-unsaturated ketone, which resulted in breaking of the conjugation. The detection limit (LOD) of the probe for HSO3 based on the definition by IUPAC was calculated to be 1.9 nM. Furthermore, the probe was employed successfully for the imaging of pH and HSO3 in live cells, which indicated that the probe was a suitable indicator for imaging the distribution of pH or HSO3 and tracking their changes.

Graphical abstract: A novel pyrene-based dual multifunctional fluorescent probe for differential sensing of pH and HSO3− and their bioimaging in live cells

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Publication details

The article was received on 14 Oct 2017, accepted on 16 Jan 2018 and first published on 17 Jan 2018


Article type: Paper
DOI: 10.1039/C7NJ03903D
Citation: New J. Chem., 2018, Advance Article
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    A novel pyrene-based dual multifunctional fluorescent probe for differential sensing of pH and HSO3 and their bioimaging in live cells

    J. Chao, H. Wang, Y. Zhang, C. Yin, F. Huo, J. Sun and M. Zhao, New J. Chem., 2018, Advance Article , DOI: 10.1039/C7NJ03903D

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