- NitroxylFluor: A Thiol-Based Fluorescent Probe for Live-Cell Imaging of Nitroxyl
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Detection of nitroxyl (HNO), the transient one-electron reduced form of nitric oxide, is a significant challenge owing to its high reactivity with biological thiols (with rate constants as high as 109 M-1 s-1). To address this, we report a new thiol-based HNO-responsive trigger that can compete against reactive thiols for HNO. This process forms a common N-hydroxysulfenamide intermediate that cyclizes to release a masked fluorophore leading to fluorescence enhancement. To ensure that the cyclization step is rapid, our design capitalizes on two established physical organic phenomena; the alpha-effect and the Thorpe-Ingold effect. Using this new trigger, we developed NitroxylFluor, a selective HNO-responsive fluorescent probe. Treatment of NitroxylFluor with an HNO donor results in a 16-fold turn-on. This probe also exhibits excellent selectivity over various reactive nitrogen, oxygen, and sulfur species and efficacy in the presence of thiols (e.g., glutathione in mM concentrations). Lastly, we successfully performed live cell imaging of HNO using NitroxylFluor.
- Pino, Nicholas W.,Davis, Jerome,Yu, Zhengxin,Chan, Jefferson
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- THIOL-BASED FLUORESCENT PROBE FOR REACTIVE SPECIES
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Detection of nitroxyl (HNO), the transient one-electron reduced form of nitric oxide, is a significant challenge owing to its high reactivity with biological thiols (rate constants as high as 109M?1 s?1). Reported herein is a new thiol-based HNO-responsive trigger that can compete against reactive thiols for HNO. This process forms an N-hydroxysulfenamide intermediate which cyclizes to release a masked fluorophore leading to fluorescence enhancement. To ensure a rapid cyclization step, the disclosed design capitalizes on two established physical organic phenomena: the alpha-effect and the Thorpe-Ingold effect. Using this new trigger, NitroxylFluor was developed; a selective HNO-responsive fluorescent probe. Treatment of NitroxylFluor with an HNO donor results in a 16-fold turn-on. This probe also exhibits excellent selectivity over various reactive nitrogen, oxygen, and sulfur species and efficacy in the presence of thiols (e.g., glutathione in mM concentrations). Also, live cell imaging of HNO using NitroxylFluor was performed.
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Paragraph 0115; 0149; 0150
(2020/05/29)
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- Allyl Fluorescein Ethers as Promising Fluorescent Probes for Carbon Monoxide Imaging in Living Cells
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Recently, the fluorescent detection of carbon monoxide (CO) in living cells has attracted great attention. However, due to the lack of effective ways to construct fluorescent CO probes, fluorescent detection of CO in living cells is still in its infancy.
- Feng, Shumin,Liu, Dandan,Feng, Weiyong,Feng, Guoqiang
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p. 3754 - 3760
(2017/05/08)
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- Photoactivatable fluorescein derivatives caged with a (3-hydroxy-2- naphthalenyl)methyl group
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The (3-hydroxy-2-naphthalenyl)methyl (NQMP) group represents an efficient photocage for fluorescein-based dyes. Thus, irradiation of the 6-NQMP ether of 2'-hydroxymethylfluorescein with low-intensity UVA light results in a 4-fold increase in emission inte
- Nekongo, Emmanuel E.,Popik, Vladimir V.
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p. 7665 - 7671
(2014/09/17)
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- Development and applications of fluorogenic probes for mercury(II) based on vinyl ether oxymercuration
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Mercury is a major threat to the environment and to human health. It is highly desirable to develop a user-friendly kit for on-site mercury detection. Such a method must be able to detect mercury below the threshold levels for drinking water, 1-2 ppb. We developed a fluorescence method based on the oxymercuration of vinyl ethers to detect mercury in dental and environmental samples. Chloride ions interfered with the oxymercuration reaction, but the addition of AgNO3 solved this problem. Fine electronic and structural tuning led to the development of a more responsive probe that was less sensitive to chloride ion interference. This second-generation probe could detect 1 ppb mercury ions in water.
- Ando, Shin,Koide, Kazunori
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experimental part
p. 2556 - 2566
(2011/05/03)
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- Preparation of polystyrene fluorescent microspheres based on some fluorescent labels
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Five fluorescent labels were synthesized and used in the preparation of polystyrene fluorescent microspheres by the dispersion copolymerization and absorption method. Spectral properties of copolymerization fluorescent microspheres in tetrahydrofuran indicated these individual characteristics of labels should be maintained in the fluorescent microspheres. The differences of the fluorescent spectra between five fluorescent microspheres and their corresponding parent labels in ethanol have been investigated. These fluorescent microspheres were characterized by environmental scanning electron microscopy, laser scanning confocal microscopy and fluorescence spectrophotometry. They exhibited good dispersion and stable and high fluorescence intensity. Furthermore, copolymerization fluorescent microspheres were functionalized with amino groups. This means that a method for the preparation of copolymerization fluorescent microspheres was developed as a platform for the generation of functional fluorescent microspheres for diverse applications. The Royal Society of Chemistry 2009.
- Liu, Qing-Hao,Liu, Jia,Guo, Jin-Chun,Yan, Xi-Long,Wang, Dong-Hua,Chen, Lei,Yan, Fan-Yong,Chen, Li-Gong
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experimental part
p. 2018 - 2025
(2010/05/19)
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- NANOPARTICLES FOR DELIVERY OF A PHARMACOLOGICALLY ACTIVE AGENT
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Core-shell nanoparticles comprising: (a) a core which comprises a water insoluble polymer or copolymer, and (b) a shell which comprises a hydrophilic polymer or copolymer; said nanoparticles being obtainable by emulsion polymerization of a mixture compris
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Page/Page column 35
(2008/06/13)
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