Construction of DCM-based NIR fluorescent probe for visualization detection of H2S in solution and nanofibrous film

Jin, Xilang; Ma, Xuehao; Zhou, Hongwei; Chen, Jiawei; Li, Minzhi; Yang, Jun; Bai, Haiyan; She, Mengyao

doi:10.1016/j.saa.2021.119764

Cited by 16 publications

(7 citation statements)

References 41 publications

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“…Li also incorporated an ortho -aldehyde to prepare 378 (2-CHO-OH), which provided good selectivity for H 2 S over competing analytes in 50% DMSO in buffer and used to image exogenous and Cys-derived H 2 S in HeLa cells . Jin and She reported related isomer 379 (DCM-NO), which provided a fluorescent response to H 2 S at 672 nm and showed moderate selectivity for H 2 S over thiols . This probe was used to image exogenous H 2 S in HeLa cells and also to prepare PMMA nanofibrous films containing the probe, which were used to measure H 2 S in water samples.…”

Section: Electrophilic H2s Probesmentioning

confidence: 99%

“…411 Jin and She reported related isomer 379 (DCM-NO), which provided a fluorescent response to H 2 S at 672 nm and showed moderate selectivity for H 2 S over thiols. 412 This probe was used to image exogenous H 2 S in HeLa cells and also to prepare PMMA nanofibrous films containing the probe, which were used to measure H 2 S in water samples. Using a naphthalene core, Zhao reported 380 (AZ-NO 2 ), which provided moderate selectivity for H 2 S over competing thiols in 50% DMSO in buffer at 620 nm.…”

Section: Electrophilic H 2 S Probesmentioning

confidence: 99%

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Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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Hydrogen sulfide (H 2 S) is not only a well-established toxic gas but also an important small molecule bioregulator in all kingdoms of life. In contemporary biology, H 2 S is often classified as a "gasotransmitter," meaning that it is an endogenously produced membrane permeable gas that carries out essential cellular processes. Fluorescent probes for H 2 S and related reactive sulfur species (RSS) detection provide an important cornerstone for investigating the multifaceted roles of these important small molecules in complex biological systems. A now common approach to develop such tools is to develop "activitybased probes" that couple a specific H 2 S-mediated chemical reaction to a fluorescent output. This Review covers the different types of such probes and also highlights the chemical mechanisms by which each probe type is activated by specific RSS. Common examples include reduction of oxidized nitrogen motifs, disulfide exchange, electrophilic reactions, metal precipitation, and metal coordination. In addition, we also outline complementary activity-based probes for imaging reductant-labile and sulfane sulfur species, including persulfides and polysulfides. For probes highlighted in this Review, we focus on small molecule systems with demonstrated compatibility in cellular systems or related applications. Building from breadth of reported activity-based strategies and application, we also highlight key unmet challenges and future opportunities for advancing activity-based probes for H 2 S and related RSS.

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Section: Electrophilic H2s Probesmentioning

confidence: 99%

Section: Electrophilic H 2 S Probesmentioning

confidence: 99%

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Fluorescence turn-on probes have acquired more attention than titrimetric, electrochemical, and ion chromatography methods for sensing these anions because of their high sensitivity, selectivity, and appropriate application in bioimaging. − Many chromogenic and fluorogenic sensors for these anions have been reported in previous years. Various modes of interactions such as CN – coordination, hydrogen bonding interactions, deprotonation, , and nucleophilic reactivity − have been incorporated to monitor cyanide ions, whereas cleavage of the alkoxyl bond (R–O), − cleavage of the S–O bond, , Michael addition, , displacement from metal ion complexes, − and reduction of azide − and nitro groups − have been utilized for the detection of sulfide, hydrosulfide ions, and hydrogen sulfide. Nowadays, the development of a multi-ion-responsive unimolecular system is one of the principal interests and not an easy task in the chemosensor field. , Among the different modes of host–guest interactions, the nucleophilic addition of anions exhibits more advantages than those of other methods such as reactivity in aqueous medium, neutral to basic pH, etc., but the main drawback is the poor selectivity due to the interference of other anions.…”

Section: Introductionmentioning

confidence: 99%

Dual-Responsive Benzo-Hemicyanine-Based Fluorescent Probe for Detection of Cyanide and Hydrogen Sulfide: Real-Time Application in Identification of Food Spoilage

Magesh

Vijay

et al. 2023

J. Agric. Food Chem.

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Colorimetric and fluorescent probes have received a lot of attention for detecting lethal analytes in realistic systems and in living things. Herein, a dual-approachable Benzo-hemicyaninebased red-emitting fluorescent probe PBiSMe, for distinct and instantaneous detection of CN– and HS– was synthesized. The PBiSMe emitted red fluorescence (570 nm) can switch to turn-off (570 nm) and blue fluorescence (465 nm) in response to CN– and HS–, respectively. Other nucleophilic reagents, such as reactive sulfur species (RSS) and anions, have no contact or interference with the probe; instead, a unique approach is undertaken to exclusively interact with CN– and HS– over a wide pH range. The measured detection limits for CN– (0.43 μM) and HS– (0.22 μM) ions are lower than the World Health Organization’s (WHO) recommended levels in drinking water. We confirmed 1:1 stoichiometry ratio using Job’s plot and observed good quantum yield for both analytes. The probe-coated paper strips were used to detect the H2S gas produced by food spoilage (such as eggs, raw meat, and fish) via an eye-catching visual response. Moreover, fluorescence bioimaging studies of living cells was done to confirm the probe’s potential by monitoring the presence of CN– and HS– in a living system.

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“…In the past few decades, dicyanomethylene-4 H -chromene (DCM) derivatives have been widely investigated as chromophores for their excellent properties and easy modification. 18–20 DCM has been extensively used in molecular probes, nano-drug delivery, and other fields. 21–23 The common DCM derivatives can be divided into oxygen-substituted, sulfur-substituted, and selenium-substituted DCM.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and application of near-infrared dyes based on sulfur-substituted dicyanomethylene-4H-chromene and diarylethene

Wang¹,

Chen

et al. 2022

New J. Chem.

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Construction of DCM-based NIR fluorescent probe for visualization detection of H2S in solution and nanofibrous film

Cited by 16 publications

References 41 publications

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Activity-Based Fluorescent Probes for Hydrogen Sulfide and Related Reactive Sulfur Species

Dual-Responsive Benzo-Hemicyanine-Based Fluorescent Probe for Detection of Cyanide and Hydrogen Sulfide: Real-Time Application in Identification of Food Spoilage

Synthesis and application of near-infrared dyes based on sulfur-substituted dicyanomethylene-4H-chromene and diarylethene

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