New fluorescent probes for sulfane sulfurs and the application in bioimaging

Chen, Wei; Liu, Chunrong; Peng, Bo; Zhao, Yu; Pacheco, Armando; Xian, Ming

doi:10.1039/c3sc50754h

Cited by 201 publications

(141 citation statements)

References 31 publications

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“…The first one is designed to be used for the detection of sulfane sulfur levels in the cells. Chen et al (2013) based their discovery on an assumption that sulfane sulfurs are likely to react with the nucleophile components of a fluorescent probe, which could then undergo spontaneous and fast cyclization to release fluorophore. They successfully produced two probes, named SSP1 and SSP2, which could be easily used for intracellular detection of sulfane sulfur.…”

Section: Detection Of Sulfane Sulfursmentioning

confidence: 99%

Persulfidation (S-sulfhydration) and H2S

Filipovic

2015

Chemistry, Biochemistry and Pharmacology of Hydrogen Sulfide

160

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

Chemistry, Biochemistry and Pharmacology of Hydrogen Sulfide

160

152

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“…7,8 Fluorescein is also used as a platform for many kinds of fluorescent probes, including Ca 2+ indicators such as Fluo-3, Fluo-4, Calcium Green-1 and Oregon Green 488 BAPTA-1. [9][10][11][12][13][14][15][16][17][18][19][20][21] The chemical structure of fluorescein consists of two parts, i.e., the benzene moiety and the xanthene moiety (the fluorophore), as shown in Figure 1a, and these two parts are orthogonal to each other. 9 Interestingly, fluorescein shows a complex chemical equilibrium involving tautomerism in aqueous solutions between pH 3.0 and 11.0, as shown in Figure 1b, 22,23 because the presence of the carboxylic group at the 2-position of the benzene moiety makes it possible for the molecule to form an intramolecular spirolactone.…”

mentioning

confidence: 99%

Analysis of Chemical Equilibrium of Silicon-Substituted Fluorescein and Its Application to Develop a Scaffold for Red Fluorescent Probes

Hirabayashi¹,

Hanaoka²,

Takayanagi

et al. 2015

Anal. Chem.

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Fluorescein is a representative green fluorophore that has been widely used as a scaffold of practically useful green fluorescent probes. Here, we report synthesis and characterization of a silicon-substituted fluorescein, i.e., 2-COOH TokyoMagenta (2-COOH TM), which is a fluorescein analogue in which the O atom at the 10' position of the xanthene moiety of fluorescein is replaced with a Si atom. This fluorescein analogue forms a spirolactone ring via intramolecular nucleophilic attack of the carboxylic group in a pH-dependent manner. Consequently, 2-COOH TM exhibits characteristic large pH-dependent absorption and fluorescence spectral changes: (1) 2-COOH TM is colorless at acidic pH, whereas fluorescein retains observable absorption and fluorescence even at acidic pH, and the absorption maximum is also shifted; (2) the absorption spectral change occurs above pH 7.0 for 2-COOH TM and below pH 7.0 for fluorescein; (3) 2-COOH TM shows a much sharper pH response than fluorescein because of its pKa inversion, i.e., pKa1 > pKa2. These features are also different from those of a compound without the carboxylic group, 2-Me TokyoMagenta (2-Me TM). Analysis of the chemical equilibrium between pH 3.0 and 11.0 disclosed that 2-COOH TM favors the colorless and nonfluorescent lactone form, compared with fluorescein. Substitution of Cl atoms at the 4' and 5' positions of the xanthene moiety of 2-COOH TM to obtain 2-COOH DCTM shifted the equilibrium so that the new derivative exists predominantly in the strongly fluorescent open form at physiological pH (pH 7.4). To demonstrate the practical utility of 2-COOH DCTM as a novel scaffold for red fluorescent probes, we employed it to develop a probe for β-galactosidase.

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“…18−30 To date, only Xian's group reported two series of fluorescent probe with short emission wavelength for selective detection of exogenous H 2 S n in living cells. 31,32 As known, near-infrared (NIR) light can penetrate tissue more deeply and minimize the interference from background autofluorescence, which greatly facilitates in vivo imaging of molecular processes. Herein, we present the design, synthesis, and application of a NIR fluorescent probe, Mito-ss, which possesses enhanced sensitivity and cellular trappability to H 2 S n .…”

mentioning

confidence: 99%

Near-Infrared Fluorescent Probe for Imaging Mitochondrial Hydrogen Polysulfides in Living Cells and in Vivo

et al. 2015

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Hydrogen polysulfides (H 2 S n , n > 1), derived from hydrogen sulfide (H 2 S), have attracted increasing attention in biochemical research, which may perform as the actual signaling molecules during cell signaling processes. Because of the closed biological and chemical relationship between H 2 S and H 2 S n , it is of great value to develop sensitive and specific techniques to distinguish the intracellular level of H 2 S n . To improve the understanding of the physiological and pathological roles played by H 2 S n , we now develop a specific fluorescent probe Mito-ss for capturing H 2 S n in cells and in vivo. When triggered by H 2 S n , Mito-ss replies a turn-on fluorescence signal and exhibits a higher selectivity toward H 2 S n than other abundant competing biothiols, such as glutathione, cysteine and H 2 S. The probe Mito-ss can also be applied to visual H 2 S n in living cells, as well as in vivo, providing a potentially powerful approach for probing H 2 S n in biological systems.

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New fluorescent probes for sulfane sulfurs and the application in bioimaging

Cited by 201 publications

References 31 publications

Persulfidation (S-sulfhydration) and H2S

Persulfidation (S-sulfhydration) and H2S

Analysis of Chemical Equilibrium of Silicon-Substituted Fluorescein and Its Application to Develop a Scaffold for Red Fluorescent Probes

Near-Infrared Fluorescent Probe for Imaging Mitochondrial Hydrogen Polysulfides in Living Cells and in Vivo

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