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

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 mu M) by the fluorescence turn-on method. Chemodosimeter I 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 I 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. (C) 2014 Elsevier Ltd. All rights reserved.