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Fluorescent probe based on phenyl selenide group specific response Cys, and preparation method and application thereof

A fluorescent probe, ether-based technology, applied in the field of fluorescent probes, achieves the effects of convenient operation, strong pH stability and obvious detection signal

Active Publication Date: 2020-09-18
上海安能健生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of phenylselenide as a detection group to utilize the strong nucleophilicity of sulfhydryl groups has very few reports on active sulfides, especially the probes that specifically recognize Cys have not yet been reported.

Method used

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  • Fluorescent probe based on phenyl selenide group specific response Cys, and preparation method and application thereof
  • Fluorescent probe based on phenyl selenide group specific response Cys, and preparation method and application thereof
  • Fluorescent probe based on phenyl selenide group specific response Cys, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The preparation steps of the probe are as follows:

[0039] (1) Preparation of compound 1

[0040]

[0041] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:2 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0042] 1 H NMR (400 MHz, DMSO) δ 10.70 (s, 1H), 7.35 (d, J = 8.4 Hz, 2H), 6.89(d, J = 8.6 Hz, 2H), 6.76 (q, J = 16.5 Hz, 2H), 6.54 (s, 1H), 6.02 (s, 1H), 3.75 (s, 3H), 2.01 (s, 3H).

[0043] (2) Preparation of compound 2

[0044]

[0045] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1, stir at 25°C for 1 h, then remove the solv...

Embodiment 2

[0055] The preparation steps of the probe are as follows:

[0056] (1) Preparation of compound 1

[0057] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:2.5 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0058] (2) Preparation of compound 2

[0059] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1.3, stir at 25°C for 1-1.5h, and then remove the solvent under reduced pressure, Compound 2 was obtained by column chromatography separation;

[0060] (3) Preparation of compound 3

[0061] Dissolve compound 2 in dichloromethane, add 1.5 equivalents of ph...

Embodiment 3

[0065] The preparation steps of the probe are as follows:

[0066] (1) Preparation of compound 1

[0067] N 2 Under the protection of the ice-water bath, sodium hydride was added to the tetrahydrofuran solvent and mixed to obtain a mixed solvent, and acetonyl p-toluenesulfonate oxime ester and p-methoxystyryl methyl ketone were dissolved in the mixed solvent according to the ratio of 1:3 equivalent, Reacted at 50°C for 4 hours, quenched with ice water, extracted with dichloromethane, and separated by column chromatography to obtain compound 1;

[0068] (2) Preparation of compound 2

[0069] Dissolve compound 1 in tetrahydrofuran, add N,N-diisopropylethylamine and triphosgene or thiophosgene at an equivalent ratio of 1:1.5, stir at 25°C for 1.5h, then remove the solvent under reduced pressure, column layer Analysis and separation obtained compound 2;

[0070] (3) Preparation of compound 3

[0071] Dissolve compound 2 in dichloromethane, add 1.5 equivalents of phosphorus ox...

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PUM

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Abstract

The invention provides a fluorescent probe based on phenyl selenide group specific response Cys, and a preparation method and application thereof. According to the probe, BODIPY dye is selected as a fluorophore, and diphenyl selenide is selected as a recognition group. The detection mechanism is that Cys and diphenyl selenide are subjected to nucleophilic substitution-rearrangement reaction to cause fluorescence signal change. The probe detects Cys through ultraviolet and fluorescence spectrometers and is not interfered by other amino acids and active oxygen, the detection process is simple, convenient, rapid and sensitive, and the detection limit is 33 nM. More importantly, the probe can be used for detecting Cys in cells and has a good application prospect in the field of biological monitoring.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a fluorescent probe based on a phenyloselenide group that specifically responds to Cys, a preparation method and an application. Background technique [0002] Biosulfide plays an important role in the metabolism of animals, plants and microscopic organisms, food processing and so on. Small molecule thiols are part of biosulfides which include: cysteine ​​(Cys), homocysteine ​​(Hcy) and glutathione (GSH). Abnormal concentrations of the three thiols may lead to various diseases, such as liver damage, cardiovascular disease, Alzheimer's disease, cancer, etc. In animals, cysteine ​​(Cys) is a proteinogenic, semi-essential amino acid that stabilizes protein structure, increases protein rigidity, and regulates protein function by providing disulfide bonds in folded proteins. The precursor of Cys synthesis is Hcy, methionine is converted into homocysteine, and then combined with serine to form a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1055G01N21/6428G01N21/6458G01N2021/6432G01N2021/6439
Inventor 张健赵伟利陶远芳王楠楠王瀚岳金磊苏慧慧
Owner 上海安能健生物医药科技有限公司
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