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Boron-dipyrromethene derivative and nano-particle, preparation methods thereof, and applications of nano-particle

A dipyrromethene, nanoparticle technology, applied in the field of boron-dipyrromethene derivatives, preparation, and nanoparticles

Active Publication Date: 2019-01-11
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there are still few reports that can achieve ultra-fast imaging (Chem.Sci., 2018, 9, 3685-3693; J.Am.Chem.Soc., 2017, 139, 14792-14799), and red light with AIE properties The emitted BODIPY derivative nanoparticles achieve ultra-fast imaging and continuous imaging in cells for more than fifteen days, and long-term imaging of tumors in biological mice for more than fourteen days has not been reported

Method used

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  • Boron-dipyrromethene derivative and nano-particle, preparation methods thereof, and applications of nano-particle

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preparation example Construction

[0042] The present invention also provides a method for preparing boron-dipyrromethene derivatives, the method comprising:

[0043] Step 1: Dissolve 4-formyltriphenylamine and 2,4-dimethylpyrrole in a dichloromethane solution in a reaction vessel, add trifluoroacetic acid, and stir in the dark under nitrogen protection. The stirring temperature is preferably Room temperature, the stirring time is preferably 20-28h, more preferably 24h, then add chlorobenzoquinone to the solution to continue stirring, the stirring time is preferably 50-60min, then add triethylamine dropwise, the dropwise Add time is preferably 10-20min, more preferably 15min, continue to stir, said stirring time is preferably 10-20min, more preferably 15min, then add boron trifluoride diethyl ether drop by drop, said dropping time is preferably 10-20min, more preferably 15min, continue stirring, the stirring time is preferably 1-3h, more preferably 2h, after the reaction is finished, it is preferably dried over...

Embodiment 1

[0056] In a 250mL three-necked flask, 4-formyltriphenylamine (0.46g, 1.7mmol) and 2,4-dimethylpyrrole (0.35g, 3.7mmol) were dissolved in 150mL of dichloromethane solution, and 1 drop of ( 0.05mL) trifluoroacetic acid, under the protection of nitrogen, stir at room temperature for 24 hours in the dark, then add chlorobenzoquinone (0.42g, 1.7mmol) to the solution, continue to stir for 1 hour, then slowly add 5mL trichloroquinone dropwise within 15 minutes Ethylamine, and then continue to stir for 15 minutes, then slowly add 5 mL of boron trifluoride diethyl ether dropwise within 15 minutes, and continue to stir for 2 hours. After the reaction, extract with water, add anhydrous sodium sulfate to dry, filter, remove the solvent under reduced pressure, and separate and purify by column chromatography to obtain 1,3,5,7-tetramethyl-8-triphenylamino-BODIPY as a yellow solid.

[0057] Dissolve iodic acid (0.35g, 2mmol) in a small amount of water, then slowly add a solution of 1,3,5,7-t...

Embodiment 2

[0061] In a 250mL three-necked flask, 4-formyltriphenylamine (0.46g, 1.7mmol) and 2,4-dimethylpyrrole (0.35g, 3.7mmol) were dissolved in 150mL of dichloromethane solution, and 1 drop of ( 0.05mL) trifluoroacetic acid, under the protection of nitrogen, stir at room temperature for 24 hours in the dark, then add chlorobenzoquinone (0.42g, 1.7mmol) to the solution, continue to stir for 1 hour, then slowly add 5mL trichloroquinone dropwise within 15 minutes Ethylamine, and then continue to stir for 15 minutes, then slowly add 5 mL of boron trifluoride diethyl ether dropwise within 15 minutes, and continue to stir for 2 hours. After the reaction, extract with water, add anhydrous sodium sulfate to dry, filter, remove the solvent under reduced pressure, and separate and purify by column chromatography to obtain 1,3,5,7-tetramethyl-8-triphenylamino-BODIPY as a yellow solid.

[0062] Dissolve iodic acid (0.35g, 2mmol) in a small amount of water, then slowly add a solution of 1,3,5,7-t...

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Abstract

The invention provides a boron-dipyrromethene derivative and a nano-particle, preparation methods thereof, and applications of the nano-particle. The derivative is a 2,6-bis(triphenylamino)-1,3,5,7-tetramethyl-8-triphenylamino-boron-dipyrromethene derivative, and has a structure represented by formula I. The invention also provides the preparation method of the boron-dipyrromethene derivative. Theinvention further provides the nano-particle formed by packaging the boron-dipyrromethene derivative in an amphiphilic polymer distearoyl phosphoethanolamine-polyethylene glycol. The nano-particle has the characteristics of good water dispersibility, excellent stability and excellent biocompatibility, can rapidly enter HeLa cells and emit red fluorescence in the cells in several seconds, and canbe used in noninvasive cell tracking and long-term imaging of tumors in vivo as a long-term cell tracer to realize intracellular ultrafast imaging and long-term bioimaging.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis and cell imaging, and specifically relates to a boron-dipyrromethene derivative, nanoparticle, preparation method and application. Background technique [0002] Noninvasive cellular imaging, which facilitates diagnosis and monitors biological structures and processes in the intracellular environment, has proven to be an indispensable and powerful tool in clinical diagnosis and biological research. Therefore, many cell imaging techniques, such as magnetic resonance imaging, single photon emission computed tomography, positron emission tomography, and fluorescence techniques, are widely used. However, among these technologies, fluorescence technology has attracted more attention due to its advantages of good biocompatibility, high contrast, high sensitivity, low cost, real-time monitoring capability, and higher resolution at the cellular level. Fluorescent materials with red or near-infr...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09K11/02C09K11/06G01N21/64
CPCC07F5/022C09K11/025C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1055G01N21/6428
Inventor 朱东霞车伟龙肖骏张丽苹谢志刚苏忠民
Owner NORTHEAST NORMAL UNIVERSITY
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