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.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.