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A highly hyperbranched cationic polysaccharide derivative containing dendritic polyamide-amine groups and its preparation method

A technology of cationic polysaccharides and polysaccharide derivatives, applied in the field of biomedical engineering, can solve problems such as the difficulty of highly hyperbranched cationic polysaccharide derivatives

Active Publication Date: 2020-04-28
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the steric hindrance effect, it is still difficult to synthesize highly hyperbranched cationic polysaccharide derivatives.

Method used

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  • A highly hyperbranched cationic polysaccharide derivative containing dendritic polyamide-amine groups and its preparation method
  • A highly hyperbranched cationic polysaccharide derivative containing dendritic polyamide-amine groups and its preparation method
  • A highly hyperbranched cationic polysaccharide derivative containing dendritic polyamide-amine groups and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0069] 1. Preparation of highly hyperbranched cationic glycogen derivatives (Gly-D4) modified by 4th generation polyamide-amine

[0070] (1) Nitrogen protection in an ice-water bath, add 10 ml of methanol solution containing 4 g of propargylamine dropwise to 30 ml of methanol solution containing 13.6 g of methyl acrylate, stir for 3 hours, heat up to room temperature and stir for 24 hours, rotate Evaporate and dry in vacuo to obtain 0.5 generation polyamidoamine (D0.5); ice-water bath with nitrogen protection, 100 ml of methanol solution containing 16.2 g of 0.5 generation polyamidoamine was added dropwise to 100 ml of ethylenediamine containing 50 g In ml of methanol solution, stirred for 3 hours, heated to room temperature and stirred for 24 hours, 30°C rotary evaporation, 30°C vacuum-dried to obtain the first-generation polyamide-amine (D1);

[0071] (2) Nitrogen protection in an ice-water bath, 50 ml of methanol solution containing 18 g of 1st generation polyamide-amine wa...

Embodiment 2

[0085] 1. Preparation of highly hyperbranched cationic glycogen derivatives (Gly-D3) modified by 3rd generation polyamide-amine

[0086] (1) Nitrogen protection in an ice-water bath, drop 5 ml of methanol solution containing 0.1 g of propargylamine into 10 ml of methanol solution containing 1 g of methyl acrylate, stir for 2 hours, warm to room temperature and stir for 24 hours, 40 Rotary evaporation at ℃, vacuum drying at 40℃ to obtain 0.5-generation polyamidoamine (D0.5); nitrogen protection in ice-water bath, 15 ml methanol solution containing 1.2 g 0.5-generation polyamido-amine was added dropwise to 6 g of B Diamine in 20 ml of methanol solution, stirred for 2 hours, heated to room temperature, stirred for 24 hours, 40°C rotary evaporation, 40°C vacuum-dried to obtain 1st generation polyamide-amine (D1);

[0087] (2) Nitrogen protection in an ice-water bath, add 20 ml of methanol solution containing 2 grams of 1st generation polyamide-amine dropwise to 25 ml of methanol s...

Embodiment 3

[0093] 1. Preparation of highly hyperbranched cationic glycogen derivatives (Gly-D4) modified by 4th generation polyamide-amine

[0094] (1) Nitrogen protection in an ice-water bath, add 10 ml of methanol solution containing 1.5 g of propargylamine dropwise to 30 ml of methanol solution containing 12 g of methyl acrylate, stir for 1 hour, heat up to room temperature and stir for 24 hours, rotate Evaporate and dry in vacuo to obtain 0.5-generation polyamidoamine (D0.5); under nitrogen protection in an ice-water bath, 30 ml of methanol solution containing 5 g of 0.5-generation polyamido-amine was added dropwise to 50 ml of 15 g of ethylenediamine In methanol solution, stirred and reacted for 1 hour, heated to room temperature and stirred for 24 hours, 60°C rotary evaporation, 60°C vacuum-dried to obtain 1st generation polyamide-amine (D1);

[0095](2) Nitrogen protection in an ice-water bath, dropwise add 30 ml of methanol solution containing 6 g of 1st generation polyamide-amin...

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Abstract

The invention discloses a highly-hyperbranched cationic polysaccharide derivative containing a dendritic polyamidoamine group and a preparation method of the highly-hyperbranched cationic polysaccharide derivative. The highly-hyperbranched cationic polysaccharide derivative containing the dendritic polyamidoamine group has a structural formula shown by a formula (I); and the highly-hyperbranched cationic polysaccharide derivative is synthesized by selectively coupling dendritic polyamidoamine (PAMAM D3 or D4) to a hyperbranched polysaccharide chain through an efficient nitrine-alkyne click reaction method. The preparation method disclosed by the invention is mild in reaction condition and has high reaction efficiency and selectivity at the same time. The prepared cationic polysaccharide derivative containing the dendritic polyamidoamine group has a characteristic of a highly-hyperbranched structure, can well form an electropositive nano-composite with siRNA, is favorable for carrying siRNA to enter cells, can improve the transfection efficiency of siRNA to genes, is expected to be used as a gene carrier and has a great prospect of application.

Description

technical field [0001] The invention belongs to the technical field of biomedical engineering. More specifically, it relates to a highly hyperbranched cationic polysaccharide derivative containing dendritic polyamide-amine groups and a preparation method thereof. Background technique [0002] Gene therapy has been clinically used to treat and prevent a series of diseases (Ginn, S.L., et al. Journal of Gene Medicine, 2013, 15, 65-77), but the key technology of gene therapy is how to design an efficient Safe gene delivery vectors to compact and protect oligonucleotides from degradation by serum nucleases (Niven, R., et al. Journal of Pharmaceutical Sciences, 1998, 87, 1292-1299). Viral vectors have shown high efficiency in gene transfection of many cell lines, but their potential carcinogenicity, immunogenicity, limited DNA compression ability and difficulties in large-scale production limit their clinical application (Anderson, W.F. Nature, 1998, 392, 25-30). [0003] In r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/00C08B35/00C08G73/02C12N15/87
CPCC08B35/00C08B37/00C08G73/028C12N15/87
Inventor 潘成林张黎明杨立群
Owner SUN YAT SEN UNIV
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