Fluorescent probe for detecting polarity of lipid droplet and application thereof

A fluorescent probe and polarity technology, applied in the field of organic small molecule fluorescent probes, can solve the problems of inconvenient wide application, invasive operation, etc., and achieve good specific response to polarity, high yield, and simple synthesis steps. Effect

Inactive Publication Date: 2019-07-19
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the diagnosis of cancer by tumor markers has become a hotspot. Although some existing tumor markers have greatly improved the diagnostic rate of cancer, their widespread application is limited due to their invasiveness and inconvenient operation.

Method used

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  • Fluorescent probe for detecting polarity of lipid droplet and application thereof
  • Fluorescent probe for detecting polarity of lipid droplet and application thereof
  • Fluorescent probe for detecting polarity of lipid droplet and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Synthesis of Fluorescent Probes

[0036] (1) Synthesis of compound 3-amino-7-diethylaminocoumarin: 3-nitro-7-diethylaminocoumarin (1) is stirred with tin chloride in concentrated hydrochloric acid (the molar ratio is 1:3), reacted for 6 hours, neutralized by adding sodium hydroxide solution until the solution was neutral, and a yellow precipitate was precipitated, filtered by suction, and purified to obtain the compound 3-amino-7-diethylaminocoumarin (2):

[0037] ;

[0038] (2) Synthesis of compound 3-(bis-4-nitrophenyl)amino-7-diethylaminocoumarin: 3-amino-7-diethylaminocoumarin (2) and p-fluoronitro Stir benzene in dimethyl sulfoxide (molar ratio is 1:2), react for 1 hour, add catalyst-cesium fluoride, react for 12 hours, precipitate yellow precipitate with deionized water, and purify by suction filtration to obtain compound 3-( Bis-4-nitrophenyl)amino-7-diethylaminocoumarin (3):

[0039] ;

[0040] (3) Synthesis of fluorescent probe: 3-(bis-4-nitro...

Embodiment 2

[0043] Example 2 UV spectra of fluorescent probes in different polar solvents

[0044] A fluorescent probe stock solution with a concentration of 1 mM was prepared as a spare, and dimethyl sulfoxide was used as a solvent. Add 10 μL of probe master solution to 2 mL of solvents of different polarities, and the final probe concentration is 5 μM. The solvents are listed in descending order of polarity: toluene, 1,4-dioxane, tetrahydrofuran, methylene chloride, dimethyl sulfoxide, methanol, and deionized water. Detect the ultraviolet absorption spectrum of each solvent, such as figure 2 Shown: The probe has different maximum absorption wavelengths in different polar solvents.

Embodiment 3

[0045] Example 3 Fluorescence spectra of fluorescent probes in solvents of different polarities

[0046] Prepare 10 mL of the fluorescent probe mother solution obtained in the example with a concentration of 1 mM as a spare, and use dimethyl sulfoxide as the solvent. Add 20 μL of the probe master solution to 2 mL of solvents of different polarities, and the final concentration of the probe is 10 μM. The solvents are listed in descending order of polarity: toluene, 1,4-dioxane, tetrahydrofuran, methylene chloride, dimethyl sulfoxide, methanol, and deionized water. The excitation wavelength is 415nm, and the fluorescence spectrum of the fluorescent probe in each solvent is detected, such as image 3 shown. Depend on image 3 It can be seen that with the increase of polarity, the maximum emission wavelength of the probe presents an obvious trend of red shift.

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Abstract

The invention provides a fluorescent probe for detecting the polarity in a cell lipid droplet. The fluorescent probe has a chemical structural formula as shown in the specification. The fluorescent probe emits relatively strong fluorescence in a lipid droplet environment of a cancer cell with relatively small polarity, and emits weak fluorescence in the lipid droplet environment of a normal cell with relatively large polarity, therefore, normal cells and cancer cells can be distinguished; the fluorescent probe can be accurately positioned in lipid droplets, and has relatively high sensitivity,good optical stability and specific polarity response, so that detection of the polarity of lipid droplets in cells can be realized. By utilizing the probe provided by the invention, the content of lipid droplets in cells can be evaluated and studied by fluorescence imaging technology, and the probe has a potential application value for studying and obtaining the physiological function of lipid droplets in cells. At the same time, synthesis steps of the probe are simple, the purification is convenient, and the yield is high.

Description

technical field [0001] The invention belongs to the field of small organic molecule fluorescent probes, in particular to a fluorescent probe for detecting lipid droplet polarity and its application. Background technique [0002] Due to its special structure and physiological functions, lipid droplets have recently attracted the attention of many researchers. Lipid droplets are ubiquitous in eukaryotic cells as lipid-rich subcellular organelles consisting of a core of neutral lipids surrounded by a monolayer of phospholipids that house associated proteins. In addition to serving as energy stores, lipid droplets are also involved in various physiological processes, including cell activation, migration, proliferation, apoptosis, etc. Accumulating evidence has linked abnormalities in lipid droplets to cancer development. It has been reported that the number of lipid droplets in cancer cells is higher than that in normal cells, because the large amount of energy provided by lip...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D311/16G01N21/64
CPCC07D311/16C09K11/06C09K2211/1007C09K2211/1014C09K2211/1088G01N21/6428
Inventor 林伟英张宇左育静杨婷新
Owner UNIV OF JINAN
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