Abstract
Hydrogen sulfide (H2S) is an important biological messenger, but few biologically-compatible methods are available for its detection in aqueous solution. Herein, we report a highly water-soluble naphthalimide-based fluorescent probe (L1), which is a highly versatile building unit that absorbs and emits at long wavelengths and is selective for hydrogen sulfide over cysteine, glutathione, and other reactive sulfur, nitrogen, and oxygen species in aqueous solution. We describe turn-on fluorescent probes based on azide group reduction on the fluorogenic ‘naphthalene’ moiety to fluorescent amines and intracellular hydrogen sulfide detection without the use of an organic solvent. L1 and L2 were synthetically modified to functional groups with comparable solubility on the N-imide site, showing a marked change in turn-on fluorescent intensity in response to hydrogen sulfide in both PBS buffer and living cells. The probes were readily employed to assess intracellular hydrogen sulfide level changes by imaging endogenous hydrogen sulfide signal in RAW264.7 cells incubated with L1 and L2. Expanding the use of L1 to complex and heterogeneous biological settings, we successfully visualized hydrogen sulfide detection in the yolk, brain and spinal cord of living zebrafish embryos, thereby providing a powerful approach for live imaging for investigating chemical signaling in complex multicellular systems.
Highlights
Terms of their response rate, accuracy, and lack of real-time determination; the most important factor in sensing hydrogen sulfide is the lack of sensors and agents that allow for its rapid and accurate detection
Whereas azide derivatives typically display low fluorescence intensity, the on-off fluorescence response is obtained after reduction to the amine counterpart fluorescence, which is strongly based on the thiolate-triggered reaction in the presence of hydrogen sulfide[46,47]
The fluorescence intensity increased with increases in the NaHS concentration. These results demonstrate that L1 has potential in visualizing hydrogen sulfide in living cells, which can likely be extended to assays involving biological fluids such as serum, blood, or tissue homogenates
Summary
Terms of their response rate, accuracy, and lack of real-time determination; the most important factor in sensing hydrogen sulfide is the lack of sensors and agents that allow for its rapid and accurate detection. Substituted naphthalimide show strong intramolecular charge transfer (ICT) in the solution state arising from their planar architecture combined with the electron-withdrawing ability of the imide core. This naphthalimide-based fluorescent reporter has many undesirable properties such as low water solubility, minor changes in the environment such as temperature and oxygen concentration[34]. We report the use of a naphthalimide-based structure as an important class of organic fluorophores, which has a unique photophysical properties and has recently been applied to many areas of chemical and biological sensing[35,36,37,38], and to the determination of hydrogen sulfide in aqueous solution. We report the visualization of bright fluorescent signal through the exogenous-responsive hydrogen sulfide detection in live zebrafish
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