A class of lipid droplet specific fluorescent probe and its synthesis method

A technology of fluorescent probe and synthesis method, which is applied in the field of lipid droplet-specific fluorescent probe and its synthesis, can solve the problems of narrow emission wavelength range and limited biological imaging application, and achieve broadened wavelength range, easy operation and wide application Effect

Active Publication Date: 2022-05-20
WEST CHINA HOSPITAL SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The present invention aims to provide a class of lipid droplet-specific fluorescent probes and its synthesis method to solve the technical problems that the emission wavelength range of existing lipid droplet-specific fluorescent probes is too narrow and its application in biological imaging is limited

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  • A class of lipid droplet specific fluorescent probe and its synthesis method
  • A class of lipid droplet specific fluorescent probe and its synthesis method
  • A class of lipid droplet specific fluorescent probe and its synthesis method

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Embodiment 1

[0039] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-targeted fluorescent probe, the chemical reaction formula of which is as follows:

[0040]

[0041]The specific steps are as follows: under the protection of argon, benzene borate (0.321g, 8.18mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (0.5g, 5mmol) and Bis(tri-tert-butylphosphine)palladium (0.0512 g, 1.95 mmol) was added to a 250 mL three-necked flask. Sonicated tetrahydrofuran (15 mL) and water (1.5 mL) were added, and the mixture was stirred at 75° C. for 24 hours under argon protection. Subsequently, it was concentrated, dissolved in dichloromethane and filtered. After further concentration, the product was separated by flash column chromatography to obtain 0.43 g of a reddish-brown product with a yield of 70.4%. figure 1 .

Embodiment 2

[0043] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-targeted fluorescent probe, the chemical reaction formula of which is as follows:

[0044]

[0045] The specific steps are as follows: under the protection of argon, methylphenylboronic acid (0.352g, 7.45mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (0.5g, 5mmol) ), bis(tri-tert-butylphosphine)palladium (0.0512g, 1.95mmol) was added to a 250mL there-necked flask. Sonicated tetrahydrofuran (15 mL) and water (1.5 mL) were added, and the mixture was stirred at 75° C. for 24 hours under argon protection. 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 0.49 g of a reddish-brown product with a yield of 75.3%. figure 2 .

Embodiment 3

[0047] A preferred embodiment of the present invention provides a method for synthesizing a lipid droplet-targeted fluorescent probe, the chemical reaction formula of which is as follows:

[0048]

[0049] The specific steps are as follows: under the protection of argon, methoxybenzeneboronic acid (0.37g, 7.13mmol), 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (0.5g, 5mmol), bis(tri-tert-butylphosphine)palladium (0.0512g, 1.95mmol) was added to a 250mL there-necked flask. Sonicated tetrahydrofuran (15 mL) and water (1.5 mL) were added, and the mixture was stirred at 75° C. for 24 hours under argon protection. Subsequently, it was concentrated, dissolved in dichloromethane and filtered. After further concentration, the product was separated by flash column chromatography to obtain 0.46 g of a reddish-brown product with a yield of 67%. image 3 .

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Abstract

The invention discloses a lipid droplet-specific fluorescent probe and a synthesis method thereof, and relates to the technical field of biomedicine. The synthetic method comprises the following steps: 4-chloro-7-nitrobenzo-2-oxa-1,3-oxadiazole (NBD-Cl) and phenylboronic acid and derivative compounds thereof are protected by an inert gas and under the action of a catalyst and a base , react in a solvent at 50-140°C for 1-72 hours, cool to room temperature, then add dichloromethane, filter, remove the solvent under reduced pressure, and separate and purify the product, wherein the phenylboronic acid compound consists of a benzene ring, R radicals and borate radicals , and the R radical and the borate radical are in the para-position of the benzene ring, and the R radical is four kinds of hydrogen atom, methyl group, methoxyl group or dimethylamino group. This kind of fluorescent probe provided by the present invention can adjust the structure of the fluorescent probe to realize the efficient control of the emitted light of the probe in the oil from blue light, green light to red light, and broaden the wavelength range of the emitted light to meet the needs of intracellular lipids. Broad application of droplet-specific fluorescence imaging.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a class of lipid droplet-specific fluorescent probes and a synthesis method thereof. Background technique [0002] Lipid droplets are intracellular lipid storage sites that contain lipids containing cholesteryl esters and triglycerides as the core surrounded by monolayer phospholipids. In recent years, lipid droplets have received increasing attention because of their involvement in various cellular physiological processes, such as: the formation of cell membranes, the transport of substances, and the intersection of proteins. The abnormal lipid droplets can lead to metabolic disorders, and cause diseases such as obesity, fatty liver, diabetes, and atherosclerosis. However, the role of lipid droplets in the pathological development of these diseases is still poorly understood. In recent years, fluorescence imaging has become an important tool to study the pathophysiology of...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D271/08C09K11/06G01N21/64
CPCC07D271/08C09K11/06G01N21/6428G01N21/6456C09K2211/1048
Inventor 陈之谦陈茂庄伟华李莉岚陈璟若
Owner WEST CHINA HOSPITAL SICHUAN UNIV
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