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A kind of cell membrane targeted nitric oxide fluorescent probe and its preparation method and application

A nitric oxide, fluorescent probe technology, applied in chemical instruments and methods, fluorescence/phosphorescence, organic chemistry, etc., can solve problems such as the inability to detect NO, achieve significant changes in fluorescence intensity, efficient and sensitive detection, and simple synthesis methods Effect

Inactive Publication Date: 2016-08-17
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the role of NO released through the cell membrane into the extracellular space in physiological processes such as intercellular signal transmission, immune defense, and vasodilation cannot be underestimated, and the existing fluorescent probes cannot detect this part of NO.

Method used

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  • A kind of cell membrane targeted nitric oxide fluorescent probe and its preparation method and application
  • A kind of cell membrane targeted nitric oxide fluorescent probe and its preparation method and application
  • A kind of cell membrane targeted nitric oxide fluorescent probe and its preparation method and application

Examples

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Effect test

Embodiment 1

[0029] (1) Dissolve 308mg of 3,4-dinitrobenzoyl chloride in 150mL of anhydrous dichloromethane, drop into 300mg of 2-hexadecylpyrrole dissolved in 30mL of anhydrous dichloromethane under nitrogen protection, and stir at room temperature 48 hours; after the reaction was completed, the solvent was removed by rotary evaporation, and the resulting mixture was purified by silica gel column chromatography, and the obtained purified product was redissolved in 100 mL of anhydrous dichloromethane, cooled to -10 ° C, and dropped into 0.12 mL of 2,4-Dimethylpyrrole and 0.114mL phosphorus oxychloride, after the dropwise addition, stir at room temperature for 36 hours, then add 0.72mL triethylamine, stir at room temperature for 10 minutes, add 0.646mL boron trifluoride diethyl ether, and continue stirring for 30 minutes , The solvent was removed by rotary evaporation, and the resulting mixture was purified by silica gel column chromatography, and the eluent was dichloromethane / n-hexane (50 / ...

Embodiment 2

[0034] (1) Dissolve 355mg 3,4-dinitrobenzoyl chloride in 150mL of anhydrous dichloromethane, drop into 300mg of 2-dodecylpyrrole dissolved in 30mL of anhydrous dichloromethane under nitrogen protection, and stir at room temperature 30 hours. After the reaction was completed, the solvent was removed by rotary evaporation, and the resulting mixture was purified by silica gel column chromatography. The purified product was redissolved in 100 mL of anhydrous dichloromethane, cooled to -5 ° C, and dropped into 0.138 mL of 2,4- After adding dimethylpyrrole and 0.131mL phosphorus oxychloride dropwise, stir at room temperature for 24 hours, then add 0.72mL triethylamine, stir at room temperature for 10 minutes, add 0.724mL boron trifluoride ether, continue stirring for 30 minutes, spin The solvent was removed by evaporation. The resulting mixture was purified by silica gel column chromatography, and the eluent was dichloromethane / n-hexane (50 / 50, v / v) to obtain 292 mg of purple powde...

Embodiment 3

[0039] (1) Dissolve 429mg of 3,4-dinitrobenzoyl chloride in 150mL of anhydrous dichloromethane, drop into 300mg of 2-octalkylpyrrole dissolved in 30mL of anhydrous dichloromethane under nitrogen protection, and stir at room temperature for 24 Hour. After the reaction was completed, the solvent was removed by rotary evaporation, and the obtained mixture was purified by silica gel column chromatography. The obtained purified product was redissolved in 100 mL of anhydrous dichloromethane, cooled to 0 °C, and dropped into 0.165 mL of 2,4-dichloromethane under nitrogen protection. After adding methylpyrrole and 0.157mL phosphorus oxychloride dropwise, stir at room temperature for 12 hours, then add 0.714mL triethylamine, stir at room temperature for 10 minutes, add 0.638mL boron trifluoride diethyl ether, continue stirring for 30 minutes, spin evaporate The solvent was removed, and the resulting mixture was purified by silica gel column chromatography, and the eluent was dichlorome...

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Abstract

The invention discloses a cell membrane-targeted fluorescent probe for detecting the release of nitric oxide in cells and a preparation method thereof, belonging to the technical field of biological detection. The outstanding feature of the probe of the present invention is that it has the ability to target and mark on the surface of the cell membrane, and at the same time has a certain water solubility, and will not penetrate the cell membrane into the inside of the cell. The fluorescent probe itself has very weak fluorescence, and the background interference of biological media is small. It can selectively react with nitric oxide under physiological conditions to generate derivative products with strong fluorescence. The common active nitrogen oxides in organisms do not interfere. . The cell membrane-targeted fluorescent probe provided by the invention can perform visual analysis on the process of releasing nitric oxide from cells.

Description

technical field [0001] The invention relates to a cell membrane-targeted fluorescent probe for detecting the release of nitric oxide in cells through fluorescence imaging, a preparation method and application thereof, and belongs to the technical field of biological detection of nitric oxide. Background technique [0002] As one of the important signaling molecules in physiological processes, nitric oxide (NO) plays a pivotal role in the cardiovascular system, nervous system and immune system, so it is of great significance for the analysis and research of NO content in organisms. In recent years, many NO analysis methods have been developed, including chemiluminescence, colorimetry, electron spin resonance, electrochemical and fluorescence analysis, among which fluorescence analysis has been studied for its advantages of high selectivity and high sensitivity. Due to the attention of researchers, a series of small molecule fluorescent probes with o-phenylenediamine as the re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F5/02G01N21/64
Inventor 王红姚惠文郭小峰张华山
Owner WUHAN UNIV
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