A cell surface specific two-photon fluorescent probe for monitoring intercellular transmission of hydrogen sulfide

Extracellular vs Intracellular Delivery of CO: Does It Matter for a Stable, Diffusible Gasotransmitter?

“…Sulfonation can limit the cellular uptake of small molecules due to decreased lipophilicity and increased water solubility of the scaffold, , with some sulfonated molecules localizing at the external polar surface of the cell membrane . Hypothesizing that sulfonation of 1 (Figure ) could provide a water-soluble, extracellular analogue of photoCORM 1 , we pursued the preparation of such a molecule.…”

The design strategies and biological applications of probes for the gaseous signaling molecule hydrogen sulfide

“…29 Based on this, Fu's group developed a two-photon probe 2 (Fig. 2), i.e., 4-azido-6-sulfo-N-hex-adecyl-1,8-naphthalimide, sodium salt, which has cell surface specificity and could be used to investigate the extracellular release behaviors of H 2 S. 30 The authors linked the azide group directly to the 4-position of naphthalimide and formed a ''pull-pull'' system, which resulted in the fluorescence quenching of naphthalimide due to the intermolecular charge transfer (ICT) process being blocked. When reacted with H 2 S, the electron-withdrawing azido group of probe 2 was transformed into an electrondonating amino group and the ICT process was restored, with a significant fluorescence enhancement.…”

“…This excellent quality of probe 3 made it possible to monitor the exogenous/endogenous H 2 S in SW480 cells and the H 2 S content in red wine. 31 Also based on the ICT mechanism, Deng's group designed and synthesized probe 4, which was similar to probes 2 and 3, and introduced an azide group at the 4-position of naphthalimide. To target mitochondria, they further introduced the triphenylphosphonium cation (TPP) in probe 4 as a mitochondrial-targeting moiety.…”

“…This excellent quality of probe 3 made it possible to monitor the exogenous/endogenous H 2 S in SW480 cells and the H 2 S content in red wine. 31…”

Reaction-Based Luminescent Probes for Reactive Sulfur, Oxygen, and Nitrogen Species: Analytical Techniques and Recent Progress

“…Hydrogen sulfide has sparked vast creativity in the design of reaction-based triggers for this reactive analyte, and these can be generally categorized into reduction-based triggers, electrophilic triggers, copper-based triggers, and a few other interesting developments, including triggers incorporating molecular recognition (Figures – ). Reduction-based triggers include azides, − sulfonyl azides, , nitro groups, − nitroso groups, and quinones . A wide variety of electrophilic triggers that operate via hydrogen sulfide’s nucleophilicity have been developed including aldehyde-assisted ester cleavage, aldehyde-assisted conjugate addition, aldehyde-assisted dinitrophenyl cleavage, nucleophilic aromatic substitution, , nucleophilic addition to an imine, , nitrobenzoxadiazole with amine ,− or alcohol , leaving groups, vinyl chloride substitution alone or followed by cyclization, an aryl cyanate, disulfide-assisted ester cleavage, − diselenide-assisted ester cleavage,…”