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硫化氢介导的硒硫醚的串联反应及其在荧光探针开发中的应用。

Hydrogen Sulfide Mediated Tandem Reaction of Selenenyl Sulfides and Its Application in Fluorescent Probe Development.

机构信息

Department of Chemistry , Washington State University , Pullman , Washington 99164 , United States.

Affiliated Cancer Hospital & Institute of Guangzhou Medical University , Guangzhou , Guangdong 510436 , China.

出版信息

Org Lett. 2019 Sep 20;21(18):7573-7576. doi: 10.1021/acs.orglett.9b02844. Epub 2019 Sep 6.

DOI:10.1021/acs.orglett.9b02844
PMID:31539932
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6756184/
Abstract

A unique reaction between HS and a selenenyl sulfide containing benzoate ester template was discovered. This reaction could be specifically triggered by HS and lead to ester bond cleavage. The reaction was not affected by the presence of thiols such as glutathione and cysteine. With this reaction, a series of fluorescent probes were synthesized and evaluated. The probes exhibited high sensitivity/selectivity for HS in both buffers and cells.

摘要

发现了 HS 与含有硒代亚磺酰基苯甲酸盐模板的独特反应。这种反应可以被 HS 特异性触发,并导致酯键断裂。该反应不受谷胱甘肽和半胱氨酸等硫醇的影响。利用该反应,合成并评价了一系列荧光探针。这些探针在缓冲液和细胞中对 HS 表现出高灵敏度/选择性。

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本文引用的文献

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A General Strategy for Development of Near-Infrared Fluorescent Probes for Bioimaging.用于生物成像的近红外荧光探针的通用发展策略。
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A practical guide to working with HS at the interface of chemistry and biology.在化学与生物学交叉领域运用高光谱成像技术的实用指南。 (注:原文中HS可能是Hyperspectral Imaging的缩写,直译为高光谱成像,这里结合语境意译为高光谱成像技术更合适,你可根据实际情况调整)
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Chemical probes for molecular imaging and detection of hydrogen sulfide and reactive sulfur species in biological systems.用于生物系统中硫化氢和活性硫物种分子成像与检测的化学探针。
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Emergence of hydrogen sulfide as an endogenous gaseous signaling molecule in cardiovascular disease.内源性气体信号分子硫化氢在心血管疾病中的作用。
Circ Res. 2014 Feb 14;114(4):730-7. doi: 10.1161/CIRCRESAHA.114.300505.
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Fluorescent probes based on nucleophilic substitution-cyclization for hydrogen sulfide detection and bioimaging.基于亲核取代-环化的荧光探针用于硫化氢的检测和生物成像。
Chemistry. 2014 Jan 20;20(4):1010-6. doi: 10.1002/chem.201303757. Epub 2013 Dec 11.
9
Physiological implications of hydrogen sulfide: a whiff exploration that blossomed.硫化氢的生理学意义:一个蓬勃发展的嗅探探索。
Physiol Rev. 2012 Apr;92(2):791-896. doi: 10.1152/physrev.00017.2011.
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Fluorescent probes for the detection of hydrogen sulfide in biological systems.用于检测生物系统中硫化氢的荧光探针。
Angew Chem Int Ed Engl. 2012 Mar 5;51(10):2282-4. doi: 10.1002/anie.201107025. Epub 2012 Jan 25.