Highly Selective Fluorescent Probe for Imaging H₂Se in Living Cells and in Vivo Based on the Disulfide Bond

Abstract

Hydrogen selenide (HSe) is an important metabolite of dietary Se compounds and has been implicated in various pathological and physiological processes. The development of highly sensitive and selective methods for the sensing of HSe is therefore very important. Herein, we developed a fluorescent probe (hemicyanine (Hcy)-HSe) for detecting HSe based on a new HSe-specific receptor unit, 1,2-dithiane-4,5-diol. Hcy-HSe showed high selectivity toward HSe over thiols (RSH), hydrogen sulfide (HS), and selenocysteine (Sec) and was further exploited for the fluorescence imaging of HSe both in living cells and in vivo. Furthermore, with the aid of Hcy-HSe, we demonstrated that HSe can be generated and gradually accumulated in HepG2 cells under hypoxic conditions and in the solid tumor after treatment with NaSeO.

A fast and specific fluorescent probe for thioredoxin reductase that works via disulphide bond cleavage

“…However, under our experimental conditions, we only observed a marginal reduction of 1,2-dithianes (compounds 6 and 7 ) by GSH. The previous work studying the direct reaction between GSH and oxidized dithiothreitol 48 and the recent work from the Tang group 25 also supported that GSH has little effect on the reduction of the 1, 2-dithiane moiety.…”

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

“…First, Butora used DTT phosphoesters to release phosphate cargos after reduction, which was stated to occur by reaction with GSH; 30,42 this approach was since used by, e.g., Urata. 43 Second, Xu and Tang used an aniline carbamate of DTT to release aniline cargos after reduction, which was stated to occur by reaction with H 2 Se; 44 Fang also applied this approach, but contradicting Butora, stated that neither TrxR nor GSH caused release. 35 Third, Ziv disclosed phenolic carbamate prodrugs of 4-amino-1,2-dithiane, intended to release the phenol cargo after reduction, though this was only described as occurring through the "ambient reductive environment" of the cell.…”

Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis

“…31,[39][40][41][42][43] Depending on the ring size, cyclic disuldes/diselenides suffer from signicant ring tension and display different reactivity from acyclic disuldes/diselenides. [44][45][46][47] Encouraged by the recent work on employing a cyclic disulde moiety to construct uorescent probes and prodrugs, 24,44,[48][49][50] we report herein the construction of a seleno-prodrug Se-Gem ( Fig. 1) by introducing a 1,2-diselenolane (ve-membered cyclic diselenide) moiety into the anticancer drug gemcitabine (Gem; Fig.…”