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A Novel Biscarbazole-Xanthene Hybrid Fluorescent Probe for Selective and Sensitive Detection of Cu2+ and Applications in Bioimaging

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Abstract

A new biscarbazole-fused xanthene hybrid dye MeBCX has been prepared by CH3SO3H-promoted condensation of 4-hydroxycarbazole and o-phthalic anhydride, followed by esterification with methanol, which exhibits good cell membrane permeability. Taking advantage of the spiro-controlled xanthene platform of the dye, a Cu2+-selective fluorescence “off-on” probe BCX-Cu has been successfully prepared with excellent performances in selectivity and sensitivity, and the detection limit is calculated to be 88.7 nM. The sensing mechanism is confirmed to involve a specific cascade reactions of Cu2+-induced spirolactam ring-opening and hydrolysis. In addition, living L929 cell imaging demonstrates the probe has living cell membrane permeability and shows great potential for tracing intracellular Cu2+ through fluorescence imaging technology.

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Acknowledgements

The authors thank the financial support of Doctoral Scientific Research Start-up Foundation of China West Normal University (18Q022), the National Natural Science Foundation of China (21671159), Meritocracy Research Funds of China West Normal University (17YC030) and Key Laboratory of Chemical Synthesis and Pollution Control of Sichuan Province (CSPC201802).

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Authors and Affiliations

  1. Key Laboratory of Chemical Synthesis and Pollution Control of Sichuan Province, School of Chemistry and Chemical Engineering, China West Normal University, Nanchong, 637002, People’s Republic of China

    Kun Huang, Defang Han, Xianglin Li, Mengni Peng, Qi Qiu & Dabin Qin

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  1. Kun Huang
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  2. Defang Han
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  3. Xianglin Li
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Correspondence to Kun Huang or Dabin Qin.

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Huang, K., Han, D., Li, X. et al. A Novel Biscarbazole-Xanthene Hybrid Fluorescent Probe for Selective and Sensitive Detection of Cu2+ and Applications in Bioimaging. J Fluoresc 29, 727–735 (2019). https://doi.org/10.1007/s10895-019-02393-1

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