Development of a Highly Selective Fluorescence Probe for Hydrogen Sulfide

Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Journal of the American Chemical Society (Impact Factor: 12.11). 11/2011; 133(45):18003-5. DOI: 10.1021/ja207851s
Source: PubMed


Hydrogen sulfide (H(2)S) has recently been identified as a biological response modifier. Here, we report the design and synthesis of a novel fluorescence probe for H(2)S, HSip-1, utilizing azamacrocyclic copper(II) ion complex chemistry to control the fluorescence. HSip-1 showed high selectivity and high sensitivity for H(2)S, and its potential for biological applications was confirmed by employing it for fluorescence imaging of H(2)S in live cells.

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    • "There are various methods for H 2 S detection such as gas chromatography [29], colorimetric assays [30], fluorescence probes and polarographic sensors [31]. The fluorescence probe based approach, because of its non-destructive and sensitive nature, is highly desirable for the selective analysis of H 2 S. Fluorescent probes for H 2 S are further subdivided into four different categories depending upon their reaction type [32], Azide-to-amine reduction approach [33] [34] [35], Nucleophilic addition approach [36] [37] [38] [39] [40] [41] [42] [43] [44], Copper displacement approach [45,46], Nitro-to-amine reduction approach [47]. Herein, we report a novel fluorescent probe based nucleophilic addition on the selective of HS − to a specific coumarin–hemicyanine derivative in medium of near neutral pH value (Scheme 1). "
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    ABSTRACT: A new selective colorimetric and fluorescent sensor for H2S, diethylaminocoumarin-hemicyanine dye has been designed, synthesized and evaluated. In CH3OH-HEPES (10 mM, pH 7.4) buffer solution containing the sensor, the addition of H2S made the UV-vis absorption of the sensor taking place blue-shift from red to yellow, and the fluorescence of the sensor also changed from red to green. Other analytes did not disturb the determination of H2S. The mechanism is based on the nucleophilic attack toward the polarized CN and an electron-poor CC bond of the sensor. Moreover, its adduct was proved by ESI-MS and NMR. The system was used to react with H2S in the cell, which can provide a potentially powerful approach for probing H2S chemistry in biological system.
    Full-text · Article · Nov 2014 · Sensors and Actuators B Chemical
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    • "We have utilized a variation of the lead acetate technique, optimized for tissue synthesis of H2S by methylene blue formation5. During 2011 a series of papers revealed new advances in applying highly selective fluorescence probes to measure H2S in living cells232425. We have combined the two techniques to investigate the regulation of leukocyte H2S synthesis. "
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    ABSTRACT: Hydrogen sulfide is an essential gasotransmitter associated with numerous pathologies. We assert that hydrogen sulfide plays an important role in regulating macrophage function in response to subsequent inflammatory stimuli, promoting clearance of leukocyte infiltrate and reducing TNF-α levels in vivo following zymosan-challenge. We describe two distinct methods of measuring leukocyte hydrogen sulfide synthesis; methylene blue formation following zinc acetate capture and a novel fluorescent sulfidefluor probe. Comparison of these methods, using pharmacological tools, revealed they were complimentary in vitro and in vivo. We demonstrate the application of sulfidefluor probe to spectrofluorimetry, flow cytometry and whole animal imaging, to monitor the regulation of hydrogen sulfide synthesis in vivo during dynamic inflammatory processes. Both methodologies revealed that granulocyte infiltration negatively affects hydrogen sulfide synthesis. Our report offers an insight into the profile of hydrogen sulfide synthesis during inflammation and highlight opportunities raised by the development of novel fluorescent hydrogen sulfide probes.
    Full-text · Article · Jul 2012 · Scientific Reports
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    ABSTRACT: Since being identified in mammalian brain, hydrogen sulfide (H2S), a well-known toxic gas with a smell of rotten eggs, was predicted to have physiological functions. Three H2S-producing enzymes have since been identified and their physiological regulation has been intensively studied. The effects of H2S on neuromodulation, smooth muscle relaxation, inflammation, and angiogenesis indicate that it functions as a signaling molecule. It also protects the nervous system and the cardiovascular system from oxidative insults, suggesting a cytoprotective role for the molecule. In contrast to these physiological functions, pathophysiological roles for H2S have also been demonstrated. Patients with ethylmalonic encephalopathy have mutations in mitochondrial dioxygenase, causing high levels of H2S to be produced, with consequent damage to the brain and skeletal muscle. Levels of cystathionine β-synthase (CBS), an H2S-producing enzyme, are 3 times higher in patients with Down’s syndrome compared to normal individuals. In this article, in addition to the basic properties of H2S, physiological and pathophysiological aspects of this important molecule are reviewed.
    No preview · Chapter · Jan 2012
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