3’-O-(2-Nitrobenzenesulfonyl)- fluorescein as a Fluorescent Probe for Hydrogen Polysulfides by Straightforward One-Step Deprotection
3’-O-(2-Nitrobenzenesulfonyl)- fluorescein as a Fluorescent Probe for Hydrogen Polysulfides by Straightforward One-Step Deprotection
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3’-O-(2-硝基苯磺酰基)-荧光素作为多硫化氢荧光探针，通过简单的一步脱保护
DOI：
10.1002/anse.202200084
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发表时间：
2022
期刊：
影响因子：
--
通讯作者：
Hatsuo Maeda
中科院分区：
文献类型：
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作者：
Koji Tsukamoto;Hikaru Ohsawa;Ryousuke Nishiyama;Hatsuo Maeda
为了开发一种基于保护-去保护化学的多硫化氢（H2Sn,n≥2）荧光探针，我们用带有不同亲电活性取代基的硝基磺酰基保护荧光素，并评估了它们对H2Sn的响应性。与硫化氢和谷胱甘肽相比，3′‐O‐（2‐硝基苯磺酰基）荧光素（1c）对h2sn2的敏感性最好。进一步的评估表明，1 c是一种优秀的探针，可与迄今为止开发的最好的h2snprobe之一psp‐3相媲美。利用1c的吸引人的特点，合成了1c的乙酰化衍生物，该衍生物被证明具有细胞渗透性，适用于H2Snin HeLa细胞的荧光成像。
To develop a fluorescent probe for hydrogen polysulfides (H2Sn,n≥2) based on protection‐deprotection chemistry, we protected fluorescein with nitrobenzenesulfonyl groups bearing various substituents with different electrophilic reactivities, and evaluated their responsiveness toward H2Sn. 3′‐O‐(2‐Nitrobenzenesulfonyl)fluorescein (1 c) provided the best sensitivity toward H2Snand selectivity over hydrogen sulfide and glutathione. Further evaluation demonstrated that1 cwas an excellent probe, comparable withPSP‐3, one of the best H2Snprobes developed to date. The attractive features of1 cwere capitalized on by synthesizing the acetylated derivative from1 c, which was shown to be cell‐permeable and applicable to the fluorescent imaging of H2Snin HeLa cells.