A highly selective fluorescent chemodosimeter for imaging hydrogen sulfide in living cells

•A 2-formylbenzoate-caged methylfluorescein chemodosimeter 1 was synthesized.•Chemodosimeter 1 could detect H2S in the range of 2.5–1000 μM.•Chemodosimeter 1 could serve as a “naked-eye” indicator for H2S.•1 exhibited high selectivity for H2S over various analytes including GSH.•1 could monitor H2S levels in living cells with low cytotoxicity.

A 2-formylbenzoate-caged methylfluorescein chemodosimeter (1) was designed and synthesized to detect hydrogen sulfide (H2S) in aqueous solution and living cells. Chemodosimeter 1 could quantificationally detect H2S in a wide concentration range (2.5–1000 μM) by the fluorescence turn-on method. Chemodosimeter 1 showed excellent selectivity toward H2S owing to its inherent two electrophilic reaction sites and the dual nucleophilicity of H2S. Additionally, chemodosimeter 1 exhibited the color changes from colorless to yellow-green upon addition of H2S. Thus, 1 can serve as a “naked-eye” indicator for H2S. Further, the recognition mechanism of chemodosimeter 1 for H2S was confirmed using electrospray ionization mass spectrometry. Finally, the preliminary biological imaging experiments and low cytotoxicity investigations demonstrated that our proposed chemodosimeter provided a promising method for the determination of H2S in aqueous solution and living cells.

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