A new fluorescent probe for sensing of biothiols and screening of acetylcholinesterase inhibitors,Organic & Biomolecular Chemistry

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A new fluorescent probe for sensing of biothiols and screening of acetylcholinesterase inhibitors
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2020/03/04 , DOI: 10.1039/d0ob00020e
Shengjun Wu _{1,

2,

3,

4} , Yuge Li _{4,

5,

6} , Tao Deng _{1,

2,

3,

4} , Xiaojuan Wang _{1,

2,

3,

4} , Shiyou Hu _{1,

2,

3,

4} , Guiyuan Peng _{4,

5,

6} , Xin-an Huang _{1,

2,

3,

4} , Yanwu Ling _{4,

7,

8,

9} , Fang Liu _{1,

2,

3,

4}

Affiliation

A new N₂O-type BODIPY probe (LF-Bop) has been proposed for the selective and sensitive detection of biologically relevant small molecular thiols. This detection is based on the Michael addition reaction between the thiol and nitrostyrene groups in the probe, which decreases the quenching effect from the nitro group, thus resulting in the recovery of the deep-red fluorescence from the BODIPY structure. The results show that LF-Bop is able to detect all tested free thiols through a fluorescence turn-on assay. The lowest limit of detection (LOD) for glutathione was found to be down to nanomolar levels (220 nM). Based on this probe, we have developed a new fluorescence assay for the screening of acetylcholinesterase inhibitors. In total, 11 natural and synthetic alkaloids have been evaluated. Both experimental measurements and theoretical molecular docking results reveal that both natural berberine and its synthetic derivative dihydroberberine are potential inhibitors of acetylcholinesterase.

中文翻译：

一种用于检测生物硫醇和筛选乙酰胆碱酯酶抑制剂的新型荧光探针

新的N ₂O型BODIPY探针（LF-Bop）已被提议用于生物相关的小分子硫醇的选择性和灵敏检测。该检测基于探针中硫醇和硝基苯乙烯基团之间的迈克尔加成反应，这降低了硝基的猝灭作用，从而从BODIPY结构中恢复了深红色荧光。结果表明，LF-Bop能够通过荧光开启测定法检测所有测试的游离硫醇。谷胱甘肽的最低检测限（LOD）被发现降至纳摩尔水平（220 nM）。基于该探针，我们开发了一种新的荧光测定法，用于筛选乙酰胆碱酯酶抑制剂。总共评估了11种天然和合成生物碱。

更新日期：2020-04-01

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