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Epoxy compound and cationic polymer and their preparation method

A technology of cationic polymers and epoxy compounds, applied in the direction of organic chemistry, can solve the problems of limited application, high cytotoxicity, and reduced transfection efficiency, and achieve the effects of improving stability, reducing cytotoxicity, and high transfection efficiency

Active Publication Date: 2014-10-22
SICHUAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Among them, polyethyleneimine (PEI) is a kind of cationic polymer gene carrier widely studied. Dendritic polyethyleneimine (bPEI 25KDa) with a molecular weight of 25kDa has a high transfection efficiency and has been used as an evaluation of cationic polymer gene carrier. The reference standard for high and low transfection efficiency, but because the cytotoxicity of the gene carrier is relatively high, and the transfection efficiency under the condition of serum will be reduced to 1 / 2 of that under the condition of no serum, thus limiting its clinical application application

Method used

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  • Epoxy compound and cationic polymer and their preparation method
  • Epoxy compound and cationic polymer and their preparation method
  • Epoxy compound and cationic polymer and their preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] (1) Add 0.02mmol (2.96g) of N,N'-dihydroxyethylethylenediamine and 0.048mmol (4.84g) of triethylamine into 100mL of dichloromethane, and stir in an ice-water bath until they are completely dissolved. Then, 0.044 mmol (8.72 g) of di-tert-butyl dicarbonate completely dissolved in 50 mL of dichloromethane was added dropwise at a speed of 3 s / drop. Ester recrystallization and column separation yielded 3.56 g of a pure white intermediate compound N,N'-2Boc-N,N'-dihydroxyethylethylenediamine with the following structure, with a yield of 51%:

[0054]

[0055] 1 H NMR (400 MHz, DMSO, TMS): δ = 1.39 (s, 18H, -Boc), 3.18 (m, J = 4 Hz, 4H, -CH 2 CH 2 OH), 3.29 (m, J = 12Hz, 4H, -CH 2 CH 2 -), 3.45 (m, J = 4 Hz, 4H, -CH 2 CH 2 OH), 4.66 (S,2H,-OH).

[0056] 13 C NMR (DMSO, 100 MHz): δ 28.02, 49.93, 55.99, 58.95, 78.38, 154.55.

[0057] HR-MS (ESI): Calcd for: C 16 h 32 N 2 o 6 : 371.2158[M+Na] + ; Found: 371.2156[M+Na] + ;

[0058] (2) At room temperature, mix 1...

Embodiment 2

[0064] (1) Add 0.02mmol (2.96g) of N,N'-dihydroxyethylethylenediamine and 0.042mmol (4.25g) of triethylamine into 100mL of dichloromethane, and stir in an ice-water bath until they are completely dissolved. Then, 0.042 mmol (9.16 g) of di-tert-butyl dicarbonate completely dissolved in 50 mL of dichloromethane was added dropwise at a rate of 2 s / drop. Ester recrystallization and column separation yielded 3.22 g of pure white intermediate compound N,N'-2Boc-N,N'-dihydroxyethylethylenediamine with a yield of 46%:

[0065]

[0066] (2) At room temperature, mix 6.3 mmol (2.2g) N,N'-2Boc-N,N'-dihydroxyethylethylenediamine, 37.9mmol (3.5g) epichlorohydrin, 37.9mmol (1.5g ) Sodium hydroxide, 0.31mmol (100mg) tetrabutylammonium bromide, 30ml dichloromethane and 1.1 mmol (20mg) water were stirred and mixed together, after the solid matter was basically dissolved, heated to 40°C for 6h, cooled to room temperature, Suction filtration, then wash the filter cake with dichloromethane and...

Embodiment 3

[0069](1) Add 0.02mmol (2.96g) N,N'-dihydroxyethylethylenediamine and 0.05mmol (5.05g) triethylamine into 100mL dichloromethane, and stir in an ice-water bath until they are completely dissolved, Then, 0.05 mmol (10.91 g) of di-tert-butyl dicarbonate completely dissolved in 50 mL of dichloromethane was added dropwise at a speed of 4 s / drop. Ester recrystallization and column separation yielded 3.99 g of pure white intermediate compound N,N'-2Boc-N,N'-dihydroxyethylethylenediamine with a yield of 57%:

[0070]

[0071] (2) At room temperature, mix 5 mmol (1.7g) N,N'-2Boc-N,N'-dihydroxyethylethylenediamine, 50mmol (4.6g) epichlorohydrin, 50mmol (2.0g) hydrogen Sodium oxide, 0.5mmol (160mg) tetrabutylammonium bromide, 20ml dichloromethane and 1mmol (18mg) water were stirred and mixed together, after the solid matter was basically dissolved, heated to 45°C for 8 hours, cooled to room temperature, and suction filtered. The filter cake was washed with dichloromethane and suction...

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Abstract

The invention discloses an epoxy compound and a cationic polymer obtained from ring opening polymerization of the epoxy. A structural formula or a general structural formula of each of the epoxy compound and the cationic polymer is as shown in the description. The invention further discloses preparations method of the epoxy compound and the cationic polymer. The cationic polymer provided by the invention can be in electrostatic bonding with electronegative DNA (deoxyribose nucleic acid) under a physiological condition to form compound particles suitable for nano size and potential for gene transfection, so that a compound can enter cells through endocytosis, the cytotoxicity of the cells is low, the transfection efficiency is high in the presence of serum or not, and the cationic polymer has the potential of clinical application; and meanwhile, the cationic polymer has certain cell selectivity so as to provide possibility for clinical targeted therapy. The preparation methods provided by the invention are simple and mature as well as easy to master and control.

Description

technical field [0001] The invention belongs to the technical field of epoxy compounds and cationic polymers and their preparation, and in particular relates to an epoxy compound and cationic polymers and their preparation methods. Background technique [0002] With the continuous development of biochemistry and molecular biology, people's understanding of the functions of nucleic acids (DNA, RNA) has been deepened, and the molecular mechanisms that cause various diseases have also been further understood. Thousands of known human diseases are gene-related, the main causes of which are gene defects and gene deletions. Now people have explored, by introducing appropriate exogenous genes into human cells to make up for gene defects or deletions, and express corresponding proteins to fundamentally eliminate the internal factors that produce disease symptoms, thus creating a new The treatment method is called gene therapy. Gene therapy has brought hope to many common and diffi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D303/27C07D301/28C08G59/50C08G59/28
Inventor 余孝其张琴芳张骥
Owner SICHUAN UNIV
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