Nanomolar Detection of H2S in an Aqueous Medium: Application in Endogenous and Exogenous Imaging of HeLa Cells and Zebrafish

摘要

The homeostasis of short-lived reactive species such as hydrogen sulfide/hypochlorous acid (H_(2)S/HOCl) in biological systems is essential for maintaining intercellular balance. An unchecked increase in biological H_(2)S concentrations impedes homeostasis. In this report, we present a molecular probe pyrene-based sulfonyl hydrazone derived from pyrene for the selective detection of H_(2)S endogenously as well as exogenously through a “turn-off” response in water. The structure of the receptor is confirmed by Fourier-transform infrared spectroscopy, ~(1)H and ~(13)C nuclear magnetic resonance spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction studies. The receptor shows excellent green emission in both the aqueous phase and solid state. Quenching of green emission of the receptor is observed only when H_(2)S is present in water with a detection limit of 18 nM. Other competing anions and cations do not have any influence on the receptor’s optical properties. The efficiency of H_(2)S detection is not negatively impacted by other reactive sulfur species too. The sensing mechanism of H_(2)S follows a chemodosimetric reductive elimination of sulfur dioxide, which is supported by product isolation. The receptor is found to be biocompatible, as evident by the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay, and its utility is extended to endogenous and exogenous fluorescence imaging of HeLa cells and zebrafish.