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A cationic polymer that responds to decharge by oxidation, its preparation method and application

A technology of cationic polymers and compounds, applied in other methods of inserting foreign genetic materials, medical preparations of non-active ingredients, drug combinations, etc., can solve undisclosed problems and achieve convenient preparation and strong lysosome escape ability , the effect of simple structure

Active Publication Date: 2021-10-15
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] However, it is not disclosed in the prior art whether the above two polymers can escape from lysosomes and avoid DNA degradation; therefore, it is necessary to design a carrier that can respond to the intracellular microenvironment, release nucleic acid drugs quickly, and avoid DNA degradation. Improve the efficacy of nucleic acid drugs

Method used

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  • A cationic polymer that responds to decharge by oxidation, its preparation method and application
  • A cationic polymer that responds to decharge by oxidation, its preparation method and application
  • A cationic polymer that responds to decharge by oxidation, its preparation method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0049] The synthesis of embodiment 1, B-PIEMA

[0050]

[0051]1-(2-Hydroxyethyl)imidazole (5.0g, 44.59mmol) was dissolved in dry dichloromethane and placed in an ice-water bath, and methacryloyl chloride (5.6g, 53.57mmol) was dissolved in dry dichloromethane Chloromethane was slowly added dropwise using a constant pressure dropping funnel. After the dropwise addition was completed, the ice-water bath was removed and the temperature was raised slowly, and the reaction was carried out overnight at room temperature. After the completion of the reaction as detected by TLC, the reaction solution was diluted with dichloromethane, washed three times with saturated aqueous sodium bicarbonate solution and saturated saline, the organic phase was collected, dried over anhydrous sodium sulfate, the filtrate was collected by filtration, and the organic solvent was removed by rotary evaporation. The crude product was separated and purified by silica gel column (ethyl acetate / n-hexane) ...

Embodiment 2

[0054] The NMR characterization of embodiment 2, B-PIEMA

[0055] The proton NMR characterization of B-PIEMA is as follows: 1 H-NMR,D 2 O: δ=8.7-9.1(1H, -NCHN-), δ=7.2-8.2(7H, ArH, -NCHCHN-), δ=5.4-5.8(2H, ArHCH 2 N-),δ=4.2-4.7(4H,-NCH 2 CH 2 OOCCH-),δ=2.3-2.6(1H,-CH 2 CH-),δ=1.6-2.2(-CH 2 CH-),δ=0.8-1.4(CH 3 -).

Embodiment 3

[0056] Example 3, B-PIEMA charge change under oxidation conditions

[0057] A certain amount of B-PIEMA was weighed and dissolved in HEPES buffer solution (pH 7.4, 10mM) at a concentration of 3mg / mL, and the final concentration of hydrogen peroxide solution was added to 80mM. Always maintain the pH value of the solution at 7.4, incubate at 37°C, and measure the Zeta potential of the solution at different times. Test results such as figure 1 As shown, the Zeta potential of B-PIEMA dropped from 30mV to 20mV quickly, and then the charge decreased slowly with time, and could drop to 10mv in 30h.

[0058] Experiments have proved that the charge of B-PIEMA will change under the treatment of active oxygen, thereby reducing the force with DNA and releasing DNA.

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Abstract

The invention discloses an oxidation-responsive decharge cationic polymer and its preparation method and application. It is obtained by quaternization of phenylboronic acid and PIEMA. Different from the commonly used gene delivery carrier, the cationic polymer synthesized by the present invention has a large amount of positive charge and can wrap DNA well, but after entering the cell, it can change the charge under the oxidation condition in the cell and release the DNA quickly Carry out transfection; the nanocomplex carrying plasmid DNA prepared by the cationic polymer of the present invention can quickly escape from lysosomes and avoid DNA degradation. The carrier has the characteristics of high efficiency and low toxicity, and has good application prospects.

Description

technical field [0001] The invention relates to the fields of macromolecules and biotechnology, in particular to an oxidation-responsive decharged cationic polymer, a preparation method and an application as a gene delivery carrier. Background technique [0002] Gene therapy refers to the introduction of exogenous normal genes into target cells to correct or compensate for diseases caused by defects and abnormal genes, so as to achieve therapeutic purposes. For tumors, especially liver cancer, which lacks targeted drugs, gene therapy is considered to be one of the most promising therapeutic methods. Currently commonly used delivery vectors can be divided into viral vectors and non-viral vectors. [0003] Non-viral vectors include cationic liposomes, polymers, dendrimers, etc. Compared with viral vectors, they have the advantages of good safety, low immunogenicity, biocompatibility and low cost of mass production. However, compared with viral vectors, the lower transfection...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08F120/34C08F8/42A61K47/32A61K48/00A61P35/00C12N15/87
CPCA61K47/32A61K48/0041A61P35/00C08F8/42C08F120/34C12N15/87
Inventor 徐骁相佳佳陶耀业王建国申有青柯庆宏岑贝妮
Owner ZHEJIANG UNIV
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