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

Abstract

The homeostasis of short-lived reactive species such as hydrogen sulfide/hypochlorous acid (H2S/HOCI) in biological systems is essential for maintaining intercellular balance. An unchecked increase in biological H2S concentrations impedes homeostasis. In this report, we present a molecular probe pyrenebased sulfonyl hydrazone derived from pyrene for the selective detection of H2S endogenously as well as exogenously through a "turn-off' response in water. The structure of the receptor is confirmed by Fourier-transform infrared spectroscopy, H-1 and C-13 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 H2S 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 H2S detection is not negatively impacted by other reactive sulfur species too. The sensing mechanism of H2S 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.