A turn-on fluorescent probe with a dansyl fluorophore for hydrogen sulfide sensing

Yan, Y. J.; Chen, Lijuan; Liu, Renyong; Zheng, Yu; Wang, Suhua

doi:10.1039/c9ra04790e

Cited by 15 publications

(6 citation statements)

References 60 publications

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“…818 Wang reported a dansyl conjugate 807 (DNS-Cu), which provided a turn-on response to H 2 S and good selectivity over competing anions and was used to investigate H 2 S in different water samples. 819 In addition to the above Cu 2+ chelating motifs, a variety of platforms have also used derivatized quinoline ligands for Cu 2+ binding and subsequent H 2 S detection. Lin reported the NIR probe 808, which incorporates a cyanine dye and 8aminoquinoline motif (Figure 165).…”

Section: Metal Precipitationmentioning

confidence: 99%

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: Metal Precipitationmentioning

confidence: 99%

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

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Therefore, developing a reliable sensitive probe for the rapid detection of sulfide in aqueous media and biological systems has received enormous attention from research communities worldwide. Lately, numerous fluorescent probes have been reported for in situ H 2 S detection and imaging, via reduction of azide to amine on the fluorogenic moiety, copper precipitation, Michael addition reactions, dual nucleophilic reactions, and thiolysis of dinitrophenyl ether . For instance, the sulfide-mediated reduction of aryl azide has been recently reported by Henthorn and Pluth, , whereas Montoya and Pluth employed the reduction of the nitro group as a strategy for sulfide sensing .…”

Section: Introductionmentioning

confidence: 99%

Sulfide-Induced Concentration-Dependent Distinct Optical Response: Unique Chromogenic Probe Developed for Analyzing Fecal Contamination in Water and Intracellular Imaging Applications

Fernandes,

Ch,

Ghosh

et al. 2024

ACS Sustainable Chem. Eng.

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Herein, we report the design and synthesis of a red luminescent ruthenium (Ru) complex with imidazophenanthroline as the chelating ligand. The metal complex showed a unique concentration-dependent distinct optical response in the presence of the target analyte, Na 2 S. At the lower concentration (micromolar range), the addition of Na 2 S resulted in the decrease of absorption maximum with a diminution of luminescence intensity. On the contrary, a bathochromic shift in the UV−visible spectrum with a turn-on luminescence response was noticed upon the addition of excess Na 2 S (millimolar range). The detailed mechanistic investigation indicated the formation of a hydrogen-bonded complex with sulfide (HS̅ ) ions at lower concentrations involving imidazole nitrogen ends. On the other hand, excess Na 2 S led to the reduction of nitro to amino group, which facilitated the extent of intramolecular charge transfer. Furthermore, we used the Ru(II) complex for analyzing H 2 S in toilet water samples, as it is the indicator of fecal contamination. Also, it was observed that chemically modified paper strips could detect H 2 S in contaminated water samples without involving any sophisticated instruments (sustainable approach). Finally, the imaging of H 2 S inside living breast cancer cells (MCF-7) was achieved under various stimulated conditions. Moreover, H 2 S-induced, concentration-dependent alternation in the luminescence signal was also noticed under intracellular conditions.

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“…[31][32][33] Currently, many fluorescent probes have been developed for H 2 S, and their reaction mechanisms include azide or nitroso reduction reaction, nucleophilic addition reaction, copper ion precipitation or thiolysis reaction, etc. [34][35][36][37] However, many reported probes lack the ability to detect hydrogen sulfide in mitochondria. This is mainly due to defects such as short fluorescence emission wavelength, poor water solubility and lack of locating groups, which result in great damage to biological cells and inability to locate mitochondria.…”

Section: Introductionmentioning

confidence: 99%

A mitochondria-targeting “off–on” AIE probe with large Stokes shift for high-contrast H₂S imaging in living cells

Chen

Zhao

et al. 2023

New J. Chem.

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A turn-on fluorescent probe with a dansyl fluorophore for hydrogen sulfide sensing

Abstract: H2S turn on the fluorescence of DNS–Cu complex probe.

Cited by 15 publications

References 60 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

Sulfide-Induced Concentration-Dependent Distinct Optical Response: Unique Chromogenic Probe Developed for Analyzing Fecal Contamination in Water and Intracellular Imaging Applications

A mitochondria-targeting “off–on” AIE probe with large Stokes shift for high-contrast H₂S imaging in living cells

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A turn-on fluorescent probe with a dansyl fluorophore for hydrogen sulfide sensing

Abstract: H2S turn on the fluorescence of DNS–Cu complex probe.

Cited by 15 publications

References 60 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

Sulfide-Induced Concentration-Dependent Distinct Optical Response: Unique Chromogenic Probe Developed for Analyzing Fecal Contamination in Water and Intracellular Imaging Applications

A mitochondria-targeting “off–on” AIE probe with large Stokes shift for high-contrast H2S imaging in living cells

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A mitochondria-targeting “off–on” AIE probe with large Stokes shift for high-contrast H₂S imaging in living cells