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A peroxynitrite fluorescent probe based on dicoumarin derivatives, preparation method and application

A peroxynitrite and fluorescent probe technology, applied in the field of fluorescent probes, can solve the problems of insufficient response speed, complex synthesis and low sensitivity, and achieve high selectivity, high selectivity and strong anti-interference ability. Effect

Active Publication Date: 2020-12-01
BIOLOGY INST OF SHANDONG ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are still some problems with the fluorescent probes reported so far, including insufficient selectivity, insufficient response speed, complex synthesis, low sensitivity, etc., and potential interference with the detection of peroxynitrite due to other substances in the living body.

Method used

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  • A peroxynitrite fluorescent probe based on dicoumarin derivatives, preparation method and application
  • A peroxynitrite fluorescent probe based on dicoumarin derivatives, preparation method and application
  • A peroxynitrite fluorescent probe based on dicoumarin derivatives, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of formula (II) compound

[0047]The synthetic design route is as follows:

[0048]

Embodiment approach 1

[0049] Embodiment 1: Dissolve 280 mg (1 mmol) of dicoumarin-based fluorophore compounds in 5 mL of dimethylformamide, then add 297 mg (1 mmol) of 4-(bromomethyl) phenylboronic acid pinacol ester and stir at room temperature for 10 h. After the reaction was completed, the crude product was obtained by rotary evaporation. If a purer product is to be obtained, the crude product can be separated by a chromatographic column with a mixed system of dichloromethane and methanol (volume ratio of 100:1) to obtain a pure product. About 396mg of pure product was obtained, the yield was 80%.

Embodiment approach 2

[0050] Embodiment 2: Dissolve 140 mg (1 mmol) of dicoumarin-based fluorophore compounds in 5 mL of ethanol, then add 371 mg (1.25 mmol) of 4-(bromomethyl) phenylboronic acid pinacol ester and stir for 8 hours at room temperature until the reaction is complete Afterwards, the crude product was obtained by rotary evaporation. If a purer product is to be obtained, the crude product can be separated by a chromatographic column with a mixed system of dichloromethane and methanol (volume ratio of 100:1) to obtain a pure product. About 376mg of pure product was obtained, the yield was 76%.

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Abstract

The invention relates to a dicoumarin derivative-based nitrite peroxide fluorescent probe as well as a preparation method and application of the dicoumarin derivative-based nitrite peroxide fluorescent probe. Specifically, the probe provided by the invention is a fluorescent probe based on a dicoumarin derivative, can be used as a nitrite peroxide fluorescent probe, and is used for measuring, detecting or screening nitrite peroxide and living cell fluorescence imaging. The dicoumarin derivative-based nitrite peroxide fluorescent probe can achieve at least one of the following technical effects: highly selective recognition function on nitrite peroxide, rapid response on nitrite peroxide, the ultra-sensitive analysis capacity on nitrite peroxide, detection capacity on nitrite peroxide underthe physiological level conditions, and strong anti-interference ability, simple synthesis and stable property are achieved.

Description

technical field [0001] The invention belongs to the field of fluorescent probes, in particular to a peroxynitrite fluorescent probe based on dicoumarin derivatives and its application in measuring, detecting or screening peroxynitrite and living cell fluorescence imaging methods ; The present invention also provides a method for preparing the fluorescent probe. Background technique [0002] Peroxynitrite is a typical reactive oxygen / nitrogen species, which is produced by the rapid reaction of nitric oxide and superoxide radicals, and has a short half-life under physiological conditions. Because peroxynitrite has strong oxidizing and nitrifying abilities, it plays a key role in many physiological and pathological processes. For example, peroxynitrite plays an important role in cell signal transduction pathways. However, due to its strong oxidation and nitrification capabilities, peroxynitrite can also cause damage to many biological macromolecules in cells, such as DNA and ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/025C09K11/06C09K2211/1007C09K2211/1088C09K2211/1096G01N21/6428G01N21/643
Inventor 盛文龙刘可春靳梦王雪陈锡强王利振
Owner BIOLOGY INST OF SHANDONG ACAD OF SCI