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A novel 3-hydroxychromone fluorescent probe for hydrogen sulfide based on an excited-state intramolecular proton transfer mechanism

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TLDR
The 3-hydroxychromone-based fluorescent probe A is based on a H2S-induced thiolysis reaction and an excited-state intramolecular proton transfer (ESIPT) process and shows high selectivity and sensitivity for the detection of H 2S over glutathione, cysteine and homocysteine.
Abstract
Hydrogen sulfide (H2S) is a signaling gasotransmitter that plays important roles in modulating the functions of different systems. We have designed and synthesized a 3-hydroxychromone-based fluorescent probe A for H2S detection. Probe A is based on a H2S-induced thiolysis reaction and an excited-state intramolecular proton transfer (ESIPT) process. The probe shows high selectivity and sensitivity for the detection of H2S over glutathione, cysteine and homocysteine. Moreover, this probe was successfully applied for imaging exogenous and endogenous H2S in living cells.

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Citations
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Journal ArticleDOI

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

TL;DR: The general approach for a reaction-based probe is to design and implement chemose-lective and biocompatible reactions, whereby a functional group on the probe molecule reacts with an analyte of inter-est with selectivity versus other biological molecules.
Journal ArticleDOI

A simple H2S fluorescent probe with long wavelength emission: Application in water, wine, living cells and detection of H2S gas

TL;DR: In this paper, a simple H2S selective fluorescent probe (L) has been designed and synthesized by two-step reactions using 4-diethylaminosalicylaldehyde and 1,4-dimethylpyridinium iodide as raw materials.
Journal ArticleDOI

Small-molecule fluorescent probes for H2S detection: Advances and perspectives

TL;DR: A recent review of small-molecule fluorescent probes for H2S imaging was presented in this paper, focusing on researches conducted between January 2018 and June 2020, and their structures and biological applications were highlighted.
Journal ArticleDOI

Regular tuning of the ESIPT reaction of 3-hydroxychromone-based derivatives by substitution of functional groups

TL;DR: In this paper, the photophysical properties of 3-hydroxychromone (HC)-based derivatives (BFHC, BTHC, BSeHC, BDTHC and BDSeHC) were explored systematically using density functional theory and time-dependent DFT (TD-DFT) methods.
Journal ArticleDOI

A near-infrared fluorescent probe based on SNAr reaction for H2S/GSH detection in living cells and zebrafish

TL;DR: The probe HZ-NBD, a near-infrared fluorescent probe based on SNAr reactions was exploited to achieve the sensitive and selective detection of H2S and glutathione (GSH) simultaneously in the same conditions and was successfully applied to bioimage H 2S and GSH in HepG2 cells and zebrafish.
References
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Journal ArticleDOI

A two-photon fluorescent probe for imaging hydrogen sulfide in living cells

TL;DR: In this article, a dinitrophenyl ether group was introduced into the 4 position of 1,8-naphthalimide, which acts as the H2S reactive site, to efficiently yield compound NI-NHS as a two-photo fluorescent probe for hydrogen sulfide.
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An easily accessible switch-on optical chemosensor for the detection of noxious metal ions Ni(II), Zn(II), Fe(III) and UO2(II)

TL;DR: In this article, two new highly selective colorimetric and fluoregenic aminopyridine Schiff bases (L1 and L2) were synthesized by simple refluxing method and characterised via standard NMR and HRMS techniques.
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New electrochemical sensor for the detection of hydrogen sulfide and other redox active species

TL;DR: In this article, a new electrochemical sensor for the detection of redox active species like H2S in aqueous solution was developed, which uses redox cycling of a redox mediator at electrodes in close proximity (thin-layer cell) to achieve high current signals and high S/N ratios.
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Hydrogen sulfide deactivates common nitrobenzofurazan-based fluorescent thiol labeling reagents.

TL;DR: These studies highlight the differential reactivity of thiols and H2S toward common thiol-labeling reagents and suggest that sufficient care must be taken when labeling or measuringThiols in cellular environments that produce H2 S due to the potential for both false-positive and eroded responses.
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Electrophilic Cyanate As a Recognition Motif for Reactive Sulfur Species: Selective Fluorescence Detection of H2S.

TL;DR: An ESIPT-based fluorescent dye, 3-hydroxyflavone, is chemically masked with an electrophilic cyanate motif in order to construct a fluorescent probe for cellular sulfur species that displays an extremely fast, highly sensitive and selective "turn-on" type fluorescent response toward H2S.
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