Endoplasmic reticulum targeted fluorescent probe for the detection of hydrogen sulfide based on a twist-blockage strategy

Abstract

An ER-targeted fluorescent probe based on a twist-blockage strategy was developed for both endogenous and exogenous H2S detection.

H2S Sensors: Synthesis, Optical Properties, and Selected Biomedical Applications under Visible and NIR Light

“…There are many kinds of H 2 S probes which have been designed and synthesized to date [ 57 , 58 , 59 ]. In the subsequent sections, we summarize two different mechanisms of H 2 S detection reported over the last 7 years [ 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 ]. These include probes ( Table 2 ) based on the principles of nucleophilic attack [ 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 ] and reduction of azide groups [ 75 , 76 , 77 , 78 , 79 , 80 ].…”

“…In this way, cyanine dyes were able to detect H 2 S. Such a mechanism has four different modes of signal transduction. These include intramolecular charge transfer (ICT) [ 61 , 62 , 63 ], twisted intramolecular charge transfer [ 64 , 65 , 66 ] (TICT), fluorescence resonance energy transfer (FRET) [ 67 , 68 , 69 ], and photoinduced electron transfer (PET) [ 72 , 73 , 74 ]. Each of these processes involves the transfer of energy within the probe in the presence of the analyte.…”

“…The excited molecular structure becomes twisted and then relaxes to the ground state, emitting light at a longer wavelength. Many TICT-based fluorescent probes are potential detectors for some small biological molecules [ 64 , 65 , 66 ].…”

Emerging analytical tools for the detection of the third gasotransmitter H2S, a comprehensive review

“…: rapid response time (4 min), 32-fold fluorescence enhancement, good quantum yield (0.45); good sensitivity (LOD = 150 nM) linear range 0 – 100 µM, pH range (5 – 10), aqueous detection medium (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid buffer) Disadv. : GSH reacts with the probe but at a lesser extent (slower rate) than sulfide Application: target endoplasmic reticulum, endogenous & exogenous H 2 S imaging in living cells [167] F14 Adv. : NIR fluorescent probe, linear range (12–38 μM), large Stokes shift (97 nm, λ ex/em = 543 nm / 640 nm) Disadv.…”

An Endoplasmic Reticulum-Targeted Ratiometric Fluorescent Probe for the Sensing of Hydrogen Sulfide in Living Cells and Zebrafish

“…Particularly, H 2 S can effectually reduce endothelial–mesenchymal transition by inhibiting ER stress . In recent years, many H 2 S fluorescent probes have been reported. − Additionally, several of them have realized organelle-targeted H 2 S levels of detection such as in mitochondria − and lysosomes. − However, only a few single-emission ER-targetable fluorescent probes have been reported for H 2 S detection. − Therefore, it is of extraordinary significance and value to design a facile ratiometric fluorescent probe for detecting H 2 S in the ER, which can avoid interference from the concentration of the probe and the microenvironment around the probe, photobleaching, etc. − …”