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Active oxygen triggered charge annihilation type supercharge cationic polymer transfection reagent, and preparation method and application thereof

A cationic polymer and transfection reagent technology, applied in the field of biomedicine, can solve the problems of lack of degradation mechanism, release of difficult biological drugs, induced cytotoxicity, etc., and achieve the effects of improving water solubility, promoting rapid release, and easy purification

Pending Publication Date: 2021-05-28
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing cationic polymer carriers still have certain defects: commonly used cationic polymers such as polyethyleneimine, polylysine, polyene polyamine, chitosan, etc. are rich in amino structures, and their charge density is affected by the environment. The pH has a great influence, and it is difficult to achieve rapid release of biopharmaceuticals in the cell; there is no effective degradation mechanism, and the excess positive charge after compression of biopharmaceuticals often induces cytotoxicity, etc.

Method used

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  • Active oxygen triggered charge annihilation type supercharge cationic polymer transfection reagent, and preparation method and application thereof
  • Active oxygen triggered charge annihilation type supercharge cationic polymer transfection reagent, and preparation method and application thereof
  • Active oxygen triggered charge annihilation type supercharge cationic polymer transfection reagent, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Embodiment 1: the synthesis of polymer a

[0067] Weigh 5.75g of formic acid into a 150mL round-bottomed flask, slowly add 1.08g of PEI (Mw=10kDa) under cooling in an ice-water bath, and fully dissolve to obtain a clear solution. Add 5.62mL of 37% formaldehyde solution, reflux reaction for 12h under heating conditions, during which the reaction temperature is controlled at 90-100°C. Subsequently, the reaction product is separated and purified. 12.5 mL of hydrochloric acid (4mol / L) is added to the reaction solution, and after fully mixing, it is evaporated to dryness. The resulting solid is dissolved in 10 mL of water, and 6.25 mL of sodium hydroxide solution (18 mol / L) is added to separate The upper organic phase was taken out, the lower aqueous phase was extracted three times with 6 mL of benzene, the organic phases were combined, anhydrous sodium carbonate particles were added to remove water, and the benzene was removed by rotary evaporation to obtain a PEI derivativ...

Embodiment 2

[0076] Embodiment 2: the synthesis of polymer b

[0077] Weigh 4.60g of formic acid in a 150mL round-bottomed flask, slowly add 2.56g of polylysine under cooling in an ice-water bath, and fully dissolve to obtain a clear solution. 8.19 mL of 37% formaldehyde solution was added, and the reaction was refluxed for 12 hours under heating conditions, during which the reaction temperature was controlled at 80-90°C. Subsequently, the reaction product is separated and purified. 12.5 mL of hydrochloric acid (4mol / L) is added to the reaction solution, and after fully mixing, it is evaporated to dryness. The resulting solid is dissolved in 10 mL of water, and 6.25 mL of sodium hydroxide solution (18 mol / L) is added to separate The upper organic phase was taken out, the lower aqueous phase was extracted three times with 6 mL of benzene, the organic phases were combined, anhydrous sodium carbonate particles were added to remove water, and the benzene was removed by rotary evaporation to ob...

Embodiment 3

[0085] Embodiment 3: the synthesis of polymer c

[0086] Weigh 4.60g of formic acid into a 150mL round-bottomed flask, slowly add 0.86g of polyene polyamine under ice-water bath cooling, fully dissolve to obtain a clear solution. 8.19 mL of 37% formaldehyde solution was added, and the reaction was refluxed for 12 hours under heating conditions, during which the reaction temperature was controlled at 80-90°C. Subsequently, the reaction product is separated and purified. 12.5 mL of hydrochloric acid (4mol / L) is added to the reaction solution, and after fully mixing, it is evaporated to dryness. The resulting solid is dissolved in 10 mL of water, and 6.25 mL of sodium hydroxide solution (18 mol / L) is added to separate The upper organic phase was taken out, the lower aqueous phase was extracted three times with 6 mL of benzene, the organic phases were combined, anhydrous sodium carbonate particles were added to remove water, and the benzene was removed by rotary evaporation to obt...

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Abstract

The invention belongs to the technical field of biological medicine, and particularly relates to an active oxygen triggered charge annihilation type supercharge cationic polymer transfection reagent, and a preparation method and application thereof. The transfection reagent is composed of a supercharge cationic polymer and a transfection reagent working solution, and the supercharge cationic polymer is a fatty amine polymer and is obtained by modifying a polyamine polymer with an active oxygen response group and quaternizing. The supercharge cationic polymer transfection reagent prepared by the invention is high in charge density, and can provide high-quantity loading of biological macromolecular drugs; and under the action of active oxygen, the supercharge cationic polymer is quickly oxidized and hydrolyzed, positive charges are annihilated, the compressed medicine is quickly released, and the transfection efficiency is high. The transfection reagent is suitable for transfection of nucleic acid, polypeptide and protein biomacromolecules and derivatives thereof, and is high in loading capacity, small in reagent dosage, low in toxicity, simple and convenient to operate, low in raw material cost and simple in preparation process.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to an active oxygen-triggered charge annihilation type supercharged cationic polymer transfection reagent and its preparation and application. Background technique [0002] Biopharmaceuticals mainly include nucleic acids, peptides, proteins, etc. Because of their high specificity and target diversity, they have received extensive attention in the treatment of major diseases such as malignant tumors, cardiovascular and cerebrovascular diseases, and neurodegenerative diseases in recent years. , is one of the most promising areas of drug development in the 21st century. Although biopharmaceuticals have many advantages in terms of curative effect, their inherent poor stability, cell uptake barrier and other property defects severely limit their clinical application. Therefore, the development of efficient biomolecular packaging and delivery vehicles to achieve targeted ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C08G69/48C08B37/08C08G83/00A61K9/51A61K47/34A61K47/36A61K31/7105C12N15/87
CPCC08G73/0226C08G69/48C08B37/003C08G73/0293C08G83/004C12N15/87A61K9/5146A61K9/5161A61K31/7105
Inventor 丁杨周建平程皓张华清盛钰
Owner CHINA PHARM UNIV
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