Rational Design and Bioimaging Applications of Highly Selective Fluorescence Probes for Hydrogen Polysulfides

Liu, Chunrong; Chen, Wei; Shi, Wen; Peng, Bo; Zhao, Yu; Ma, Huimin; Xian, Ming

doi:10.1021/ja502968x

Cited by 204 publications

(131 citation statements)

References 33 publications

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“…They successfully produced two probes, named SSP1 and SSP2, which could be easily used for intracellular detection of sulfane sulfur. The same group improved the probes designing a new DSP-3 fluorescence sensor for hydrogen polysulfides (Liu et al 2014a).…”

Section: Detection Of Sulfane Sulfursmentioning

confidence: 99%

Persulfidation (S-sulfhydration) and H2S

Filipovic

2015

Handbook of Experimental Pharmacology

166

152

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The past decade has witnessed the discovery of hydrogen sulfide (H2S) as a new signalling molecule. Its ability to act as a neurotransmitter, regulator of blood pressure, immunomodulator or anti-apoptotic agent, together with its great pharmacological potential, is now well established. Notwithstanding the growing body of evidence showing the biological roles of H2S, the gap between the macroscopic descriptions and the actual mechanism(s) behind these processes is getting larger. The reactivity towards reactive oxygen and nitrogen species and/or metal centres cannot explain this plethora of biological effects. Therefore, a mechanism involving modification of protein cysteine residues to form protein persulfides is proposed. It is alternatively called S-sulfhydration. Persulfides are not particularly stable and show increased reactivity when compared to free thiols. Detection of protein persulfides is still facing methodological limitations, and mechanisms by which H2S causes this modification are still largely scarce. Persulfidation of protein such as KATP could contribute to H2S-induced vasodilation, while S-sulfhydration of GAPDH and NF-κB inhibits apoptosis. H2S regulates endoplasmic reticulum stress by causing persulfidation of PTP-1B. Several other proteins have been found to be regulated by this posttranslational modification of cysteine. This review article provides a critical overview of the current state of the literature addressing protein S-sulfhydration, with particular emphasis on the challenges and future research directions in this particular field.

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Section: Detection Of Sulfane Sulfursmentioning

confidence: 99%

Persulfidation (S-sulfhydration) and H2S

Filipovic

2015

Handbook of Experimental Pharmacology

166

152

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“…In 2014, we reported the first H 2 S n -specific probes ( DSP , Scheme 1) which employed a 2-fluoro-5-nitro-benzoic ester template to trap H 2 S n and promote an intramolecular cyclization to release a fluorophore. [8] DSP probes, such as DSP-3 , showed satisfactory sensitivity and selectivity for H 2 S n . Several other groups have adopted the same template to develop H 2 S n probes with interesting properties.…”

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confidence: 99%

The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides

et al. 2015

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Endogenous hydrogen polysulfides (H2Sn, n > 1) have been recognized as important regulators in sulfur-related redox biology. H2Sn can activate tumor suppressors, ion channels, and transcription factors with higher potency than H2S. While H2Sn are drawing increasing attention, their exact mechanisms of actions are still poorly understood. A major hurdle in this field is the lack of reliable and convenient methods for H2Sn detection. In this work we report a H2Sn-mediated benzodithiolone formation under mild conditions. This reaction takes advantage of the unique dual-reactivity of H2Sn as both a nucleophile and an electrophile. It opens a door for better understanding H2Sn's chemical biology. Based on this reaction, three fluorescent probes (PSP-1~3) were synthesized and evaluated. Among the probes prepared, PSP-3 showed a desirable off-on fluorescence response to H2Sn and high specificity. It was successfully applied in visualizing intracellular H2Sn.

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“…5a) (49). In this molecular design, the fluorophore is linked to 2-fluoro-5-nitrobenzoate via an ester bond.…”

Section: Development Of Fluorescent Probes For Hydropersulfide and Pomentioning

confidence: 99%

Fluorescent Probes and Selective Inhibitors for Biological Studies of Hydrogen Sulfide- and Polysulfide-Mediated Signaling

Takano

Echizen

Hanaoka

2017

Antioxidants & Redox Signaling

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Significance: Hydrogen sulfide (H2S) plays roles in many physiological processes, including relaxation of vascular smooth muscles, mediation of neurotransmission, inhibition of insulin signaling, and regulation of inflammation. Also, hydropersulfide (R−S−SH) and polysulfide (−S−Sn−S−) have recently been identified as reactive sulfur species (RSS) that regulate the bioactivities of multiple proteins via S-sulfhydration of cysteine residues (protein Cys−SSH) and show cytoprotection. Chemical tools such as fluorescent probes and selective inhibitors are needed to establish in detail the physiological roles of H2S and polysulfide.Recent Advances: Although many fluorescent probes for H2S are available, fluorescent probes for hydropersulfide and polysulfide have only recently been developed and used to detect these sulfur species in living cells.Critical Issues: In this review, we summarize recent progress in developing chemical tools for the study of H2S, hydropersulfide, and polysulfide, covering fluorescent probes based on various design strategies and selective inhibitors of H2S- and polysulfide-producing enzymes (cystathionine γ-lyase, cystathionine β-synthase, and 3-mercaptopyruvate sulfurtransferase), and we summarize their applications in biological studies.Future Directions: Despite recent progress, the precise biological functions of H2S, hydropersulfide, and polysulfide remain to be fully established. Fluorescent probes and selective inhibitors are effective chemical tools to study the physiological roles of these sulfur molecules in living cells and tissues. Therefore, further development of a broad range of practical fluorescent probes and selective inhibitors as tools for studies of RSS biology is currently attracting great interest. Antioxid. Redox Signal. 27, 669–683.

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Rational Design and Bioimaging Applications of Highly Selective Fluorescence Probes for Hydrogen Polysulfides

Cited by 204 publications

References 33 publications

Persulfidation (S-sulfhydration) and H2S

Persulfidation (S-sulfhydration) and H2S

The Development of Fluorescent Probes for Visualizing Intracellular Hydrogen Polysulfides

Fluorescent Probes and Selective Inhibitors for Biological Studies of Hydrogen Sulfide- and Polysulfide-Mediated Signaling

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