A bio-friendly biotin-coupled and azide-functionalized naphthalimide for real-time endogenous hydrogen sulfide...

Hydrogen sulfide (H₂S) is involved in various biological processes. Thereby, abnormal levels of H₂S are reported to be related to various human diseases including cancer. Currently, many fluorescent probes are pioneered to detect H₂S by taking advantages of naphthalimides' unique internal charge transfer (ICT) property. However, most probes often require a high content of organic solvents or surfactants, and are limited to the analysis of exogenous H₂S treated externally in live cell studies, and have difficulties in analyzing endogenous H₂S, thus limiting their practical use. In this study, we developed a bio-friendly biotin-coupled and azide-functionalized naphthalimide (1) as a fluorescent probe enabling real-time analysis of H₂S in living system. Probe was able to provide a fluorescence at 545 nm via H₂S-mediated azide reduction selectively without interference by biologically abundant constituents and pH effects. In a biological study using A549 cells, probe readily penetrated living cells without cytotoxicity, and unreacted probes showed almost no fluorescence, enabling real-time detection of H₂S in living cells without requiring separate washing process. More importantly, under stimulation with various H₂S inducers and inhibitors, probe was able to provide an effective fluorescence response against fluctuations in endogenous H₂S, a key requirement for H₂S studies. Probe 1 can be applied as a useful chemical tool and enables the analysis of H₂S and the study of H₂S-related cell functions in a variety of environments.