A fluorescence turn-on probe for hydrogen sulfide and biothiols based on PET & TICT and its imaging in HeLa cells

In this paper, a photoinduced electron transfer (PET)& twisted intramolecular charge transfer (TICT)-based fluorescent probe (1) for detecting biothiols (GSH/Cys/Hcy) and hydrogen sulfide with fluorescence turn on was developed. The probe could recognize hydrogen sulfide over primary ions and selectively detect GSH/Cys/Hcy over other amino acids with fluorescence turn-on (an ESIPT process). H2S can be distinguished from GSH/Cys/Hcy with wavelength shift by UV-Vis spectra. In addition, detection limits for H2S/GSH/Cys/Hcy of probe 1 were 1.42 mu M (0-100 mu M), 0.13 mu M (0-40 mu M), 0.27 (0-30 mu M), 0.22 mu M (0-40 mu M), respectively. The proposed thiolysis of the 2,4-dinitrochlorophenyl ether reaction in identification process was verified by the characteristic peak in H-1 NMR and HRMS spectra. Finally, the biological imaging experiments and low cytotoxicity investigations in HeLa cells demonstrated that probe 1 could provide a promising method for the determination of H2S and biothiols in aqueous solution and living cells. (C) 2020 Published by Elsevier B.V.

Automated summary

A fluorescent probe based on photoinduced electron transfer (PET) and twisted intramolecular charge transfer (TICT) was developed for detecting biothiols and hydrogen sulfide with fluorescence turn on. The probe showed selective recognition and detection capabilities in aqueous solution and HeLa cells, providing a promising method for determination of H2S and biothiols.