Rational design of a GSH silent fluorescent probe for simultaneous detection of H2S and Cys/Hcy from distinct channels

Liu, Xiangbao; Fu, Shuang; Zhang, Honggang; Li, Shuang; Zhu, Zhen; Chen, Song; Hou, Huiling; Chen, Wenqiang; Hou, Peipei

doi:10.1016/j.microc.2022.108187

Cited by 9 publications

(3 citation statements)

References 45 publications

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“…638 Hou used a similar approach using an NBD thioether in combination with an H 2 S responsive thiophene ester to develop 620 (COT-NBD), which provided responses to H 2 S and Cys/Hcy, but not GSH, in different channels. 639 These differentiated responses were further demonstrated in MCF-7 cells and zebrafish.…”

Section: Nitrobenzofurazan (Nbd) Cleavagementioning

confidence: 81%

“…Xi and Yi reported naphthalimide-based 619 , which also showed enhanced selectivity when compared to the monofunctionalized probes, and was used to image exogenous H 2 S in HEK293 cells . Hou used a similar approach using an NBD thioether in combination with an H 2 S responsive thiophene ester to develop 620 (COT-NBD), which provided responses to H 2 S and Cys/Hcy, but not GSH, in different channels . These differentiated responses were further demonstrated in MCF-7 cells and zebrafish.…”

Section: Electrophilic H2s 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: Nitrobenzofurazan (Nbd) Cleavagementioning

confidence: 81%

Section: Electrophilic H2s Probesmentioning

confidence: 99%

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

Fosnacht,

Pluth

2024

Chem. Rev.

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“…Although these techniques can be well implemented for the analysis of biothiols, they have the drawbacks of complex sample handling, low sensitivity and high cost that restrict their utilization in biological samples. Nevertheless, fluorescent probes, as a convenience assay method, are considered advantageous for detecting target bioanalytes, allowing non-destructive detection, high selectivity, excellent spatial and temporal resolution and good biocompatibility [14][15][16][17][18]. Based on the above outstanding properties, fa luorescent probe has a wide range of applications in pharmacology, medicine, physiology and biology.…”

Section: Introductionmentioning

confidence: 99%

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

Yan

Hou

et al. 2023

Molecules

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The well-known small-molecule biothiols have been used to maintain the normal metabolism of peroxy radicals, forming protein structures, resisting cell apoptosis, regulating metabolism, and protecting the homeostasis of cells in the organism. A large amount of research has found that abnormal levels of the above biothiols can cause some adverse diseases, such as changes in hair pigmentation, a slower growth rate, delayed response, excessive sleep and skin diseases. In order to further investigate the exact intracellular molecular mechanism of biothiols, it is imperative to explore effective strategies for real-time biothiol detection in living systems. In this work, a new near-infrared (NIR) emission fluorescence probe (probe 1) for sensitive and selective detection of biothiols was devised by combining dicyanoisophorone derivatives with the dinitrobenzenesulfonyl (DNBS) group. As expected, probe 1 could specifically detect biothiols (Cys, Hcy and GSH) through the dinitrobenzenesulfonyl group to form dye 2, which works as a signaling molecule for sensing biothiols in real samples. Surprisingly, probe 1 showed superior sensing characteristics and low-limit detection towards biothiols (36.0 nM for Cys, 39.0 nM for Hcy and 48.0 nM for GSH) with a large Stokes shift (134 nm). Additionally, the function of probe 1 as a platform for detecting biothiols was confirmed by confocal fluorescence imaging of biothiols in MCF-7 cells and zebrafish. More importantly, the capability of probe 1 in vivo has been further evaluated by imaging the overexpressed biothiols in tumor tissue. It is reasonable to believe that probe 1 can provide a valuable method to explore the relationship between biothiols and the genesis of tumor.

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Real-time monitoring of endogenous cysteine in LPS-induced oxidative stress process with a novel lysosome-targeted fluorescent probe

Yang,

Li,

et al. 2023

Analytica Chimica Acta

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Rational design of a GSH silent fluorescent probe for simultaneous detection of H2S and Cys/Hcy from distinct channels

Cited by 9 publications

References 45 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

Bioimaging and Sensing Thiols In Vivo and in Tumor Tissues Based on a Near-Infrared Fluorescent Probe with Large Stokes Shift

Real-time monitoring of endogenous cysteine in LPS-induced oxidative stress process with a novel lysosome-targeted fluorescent probe

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