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An AIE-Active probe for detection and bioimaging of pH values based on lactone hydrolysis reaction

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Abstract

Cellular pH homeostasis is essential for many physiological and pathological processes. pH monitoring is helpful for the diagnosis, treatment and prevention of disorders and diseases. Herein, we developed a ratiometric fluorescent pH probe (TCC) based on a coumarin derivative containing a highly active lactone ring. TCC exhibited a typical AIE effect and emitted blue fluorescence under weak acidic condition. When under weak basic condition, the active lactone moiety underwent a hydrolysis reaction to afford a water-soluble product, which gave red-shifted emission. The emission color change from blue through cyan and then to yellow within pH 6.5–9.0 which is approximate to the biological pH range. And the fluorescence color change along with pH value is reversible. Furthermore, TCC was successfully utilized in the detection of the intracellular pH change of live HeLa cells, which indicated that TCC had practical potential in biomedical research.

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Availability of data and material

/ Data availability The crystallographic information files that have been deposited in the Cambridge Crystallographic Data Centre (CCDC 2,131,284) which are freely available for all. The link for CCDC: https://www.ccdc.cam.ac.uk/.

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Funding

This work is financially supported by Hainan Provincial Natural Science Foundation of China (222MS059), the National Natural Science Foundation of China (22061016) and Program for Innovative Research Team in University (IRT-16R19).

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Authors and Affiliations

  1. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education, Key Laboratory of Tropical Medicinal Plant Chemistry of Hainan Province, College of Chemistry & Chemical Engineering, Hainan normal University, 571158, Haikou, China

    Qiao Li, Zhigang Niu, Xuying Nan & Enju Wang

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  1. Qiao Li
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  2. Zhigang Niu
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  4. Enju Wang
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Contributions

EW contributed to the study conception and design, and was the major contributor in writing the manuscript. The synthesis, spectrum test, data analysis and so on were performed by QL with the assistance of XN. The X-ray diffraction data collection and structure determination was performed by ZN.

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Correspondence to Enju Wang.

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Li, Q., Niu, Z., Nan, X. et al. An AIE-Active probe for detection and bioimaging of pH values based on lactone hydrolysis reaction. J Fluoresc 32, 1611–1617 (2022). https://doi.org/10.1007/s10895-022-02967-6

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  • DOI: https://doi.org/10.1007/s10895-022-02967-6

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