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A fluorescent probe based on N-butylbenzene-1,2-diamine for Cu(II) and its imaging in living cells

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Abstract

A fluorescent probe LZ-N with naphthalimide as fluorophore and N-butylbenzene-1,2-diamine as a new recognition moiety for copper ion was designed and synthesized. The probe LZ-N exhibits high selectivity for Cu2+ ion in aqueous media (CH3CN:H2O = 1:1) over all the other metal ions in our study, more than 20-fold fluorescence enhancement by coordinating with Cu2+, and the maximum emission intensity independence in the range of pH 2.06–9.25. The results of 1H-NMR titration, time-resolved fluorescence decay measurement, and computational optimization illuminate the mechanisms of Cu2+ and probe LZ-N. Confocal fluorescence images and cell viability values test show the high fluorescence enhancement of probe LZ-N for exogenous Cu2+ in living cells.

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Acknowledgments

We thank financial support from the National Key Project for Basic Research of China (2009CB724706).

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Authors and Affiliations

  1. State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian, 116012, China

    Chunyan Zou, Lingzhi Gao, Tianyu Liu & Jingnan Cui

  2. Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China

    Zhaochao Xu

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  1. Chunyan Zou
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  2. Lingzhi Gao
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  5. Jingnan Cui
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Correspondence to Jingnan Cui.

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Zou, C., Gao, L., Liu, T. et al. A fluorescent probe based on N-butylbenzene-1,2-diamine for Cu(II) and its imaging in living cells. J Incl Phenom Macrocycl Chem 80, 383–390 (2014). https://doi.org/10.1007/s10847-014-0424-4

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