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Lipid droplet targeting fluorescent probe and synthesis method and application thereof

The technology of a fluorescent probe and a synthesis method is applied in the field of lipid droplet targeting fluorescent probe and its synthesis, and achieves the effects of simple preparation method, easy availability of raw materials, and improved sensitivity and signal-to-noise ratio.

Active Publication Date: 2021-02-05
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a large number of fluorescent probes have been reported, the fluorescent probes for lipid droplet-specific imaging still need to be further developed, especially lipid droplet targets that have no fluorescence at all in aqueous or organic solvents but have strong fluorescent signals in lipid droplets. Directional fluorescent probes urgently need to be developed

Method used

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  • Lipid droplet targeting fluorescent probe and synthesis method and application thereof
  • Lipid droplet targeting fluorescent probe and synthesis method and application thereof
  • Lipid droplet targeting fluorescent probe and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet targeting fluorescent probe, the specific steps are as follows:

[0039]

[0040] Under argon protection, triphenylamine borate (2.00g, 6.92mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (1.31g, 6.56mmol), tetrakis( Triphenylphosphine)palladium (0.25g, 0.22mol) and sodium carbonate (2.09g, 19.69mmol) were added into a 250mL three-necked flask. Then sonicated toluene (100 mL), ethanol (30 mL) and water (10 mL) were added, and stirred at 110° C. for 24 hours under the protection of argon. Subsequent concentration, dissolution with dichloromethane and filtration, further concentration and isolation of the product by flash column chromatography yielded 1.93 g of reddish-brown product, 70.4% yield. 1 H NMR (400MHz, CDCl 3 ):δ=7.12-7.24(m,8H),7.32-7.39(t,4H),7.62-7.67(d,1H),7.98-8.04(dd,2H),8.53-8.57(d,1H)ppm.

Embodiment 2

[0042] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet targeting fluorescent probe, the specific steps are as follows:

[0043]

[0044]Under argon protection, triphenylamine borate (2.00g, 6.92mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (1.31g, 6.56mmol), di( Tri-tert-butylphosphine)palladium (67.10mg, 0.13mol) and potassium carbonate (2.72g, 19.69mmol) were added into a 250mL three-neck flask. Added sonicated toluene (50 mL) and methanol (50 mL), stirred at 75° C. for 24 hours under the protection of argon. Subsequent concentration, dissolution with dichloromethane and filtration, further concentration and isolation of the product by flash column chromatography yielded 2.28 g of a reddish-brown product with a yield of 85.1%.

Embodiment 3

[0046] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet targeting fluorescent probe, the specific steps are as follows:

[0047]

[0048] Under argon protection, B-4-[bis(4-methylphenyl)amino]phenyl]boronic acid (1.00g, 3.15mmol), 4-chloro-7-nitrobenzo-2-oxa -1,3-oxadiazole (0.63g, 3.15mmol), tetrakis(triphenylphosphine)palladium (0.15g, 0.13mol) and sodium carbonate (1.00g, 9.46mmol) were added into a 250mL three-necked flask. Then sonicated toluene (100 mL), ethanol (30 mL) and water (10 mL) were added, and stirred at 110° C. for 24 hours under the protection of argon. After the reaction was completed, it was concentrated, dissolved in dichloromethane and filtered. After further concentration, the product was separated by flash column chromatography to obtain 0.85 g of a reddish-brown product with a yield of 61.8%. 1 H NMR (400MHz, CDCl 3 ):δ=2.33-2.38(s,6H),7.06-7.13(m,6H),7.13-7.19(d,4H),7.56-7.64(d,1H),7.96-8.02(dd,2H...

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Abstract

The invention discloses a lipid droplet targeting fluorescent probe and a synthesis method and application thereof. The synthetic method comprises the following steps of enabling a triphenylamine phenylboronic acid compound and 4-chloro-7-nitrobenzo-2-oxa-1, 3-diazole to react for 10-50 h in an organic solvent at the temperature of 60-120 DEG C under the protection of inert gas and the action of acatalyst and alkali, cooling the reaction product to the room temperature, adding dichloromethane, filtering, decompressing to remove the solvent, separating and purifying the product, and drying theproduct. The fluorescent probe provided by the invention has no fluorescence in an aqueous solution, basically has no fluorescence in an organic solvent, has very strong fluorescence in grease, and can specifically target lipid droplets in cells.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a lipid droplet targeting fluorescent probe, a synthesis method and application thereof. Background technique [0002] Lipid droplets are the main storage place of intracellular lipids and an important energy storage center of cells. Not only that, lipid droplet is also a complex, dynamically changing multifunctional organelle, which plays a very important role in intracellular lipid metabolism and storage, protein degradation, signal transduction, and membrane transport. And the development of many diseases is also closely related to lipid droplets, such as atherosclerosis, fatty liver and obesity. The content of lipid droplets in various types of cells and the dynamic process of lipid droplets are of great significance to the study of lipid droplet-related diseases. Therefore, developing a class of lipid droplet-specific fluorescent probes to visually observe ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D271/12C09K11/06G01N21/64
CPCC07D271/12C09K11/06G01N21/6428G01N21/6458C09K2211/1014C09K2211/1048G01N2021/6439Y02P20/55
Inventor 李淑芬
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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