Phenyloboricacid-modified cationic polymer and composite method and application thereof

A technology of cationic polymers and phenylboronic acid, which is applied in the direction of introducing foreign genetic material using carriers and recombinant DNA technology, etc., can solve the problems of high cost and wide application, lack of safe and effective delivery system for gene drugs, etc., and achieve high-efficiency transfection , high transfection efficiency

Inactive Publication Date: 2009-12-09
常熟紫金知识产权服务有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the lack of a safe and effective delivery system for gene drugs is considered to be one of the biggest obstacles in clinical application.
Immunogenicity, potential carcinogenicity, and high cost of viral vectors limit its wide application

Method used

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  • Phenyloboricacid-modified cationic polymer and composite method and application thereof
  • Phenyloboricacid-modified cationic polymer and composite method and application thereof
  • Phenyloboricacid-modified cationic polymer and composite method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The present invention will be described in detail below in conjunction with the examples, but not limited to the content disclosed in the examples. Example 1: PEI 1800 -pPB 1.9 (PEI represents that the cationic polymer is polyethyleneimine; numbers such as 1800 represent the molecular weight of polyethyleneimine, the same below; PB represents different types of phenylboronic acid groups on the cationic polymer, and the specific structure of the phenylboronic acid group As described in the examples, the same below; o, m, p represent the relative positions of the R group and the boronic acid group on the phenylboronic acid, which are respectively ortho, meta, and para; 1.9 represents that there are 1.9 benzene on each polyethyleneimine molecule Boric acid group, the same below.)

[0027] Dissolve 1.1mmol of p-(bromomethyl)phenylboronic acid in 20ml of methanol to obtain a methanol solution of phenylboronic acid. Under stirring conditions, add the methanol solution of ph...

Embodiment 2

[0028] Example 2: PEI 1800 -pPB 3.2

[0029] Dissolve 2.2mmol of p-(bromomethyl)phenylboronic acid in 20ml of methanol, add the methanol solution of phenylboronic acid into 15ml of 0.56mmol PEI1800 in methanol under stirring, continue to stir and react at 20°C for 36 hours, and spin down under reduced pressure. steamed to remove most of the methanol, the crude product was added to precipitate in ether, after standing, the upper solution was poured off, the precipitate was collected, and after drying, the polyethyleneimine modified by phenylboronic acid was obtained. 1 H NMR (300MHz, D 2 O): δ7.41(d, 2H), 7.13(d, 2H), 2.68-2.50(m, NCH 2 CH 2 N, NCH 2 CHPB), determined by proton nuclear magnetic resonance spectrum, the final product is PEI 1800 -pPB 3.2 .

Embodiment 3

[0030] Example 3: PEI 1800 -pPB 5.4

[0031] Dissolve 4.4mmol of p-(bromomethyl)phenylboronic acid in 40ml of methanol, add the methanol solution of phenylboronic acid to 15ml of 0.56mmol PEI1800 in methanol under stirring, continue to stir and react at 50°C for 18 hours, and rotate under reduced pressure steamed to remove most of the methanol, the crude product was added to precipitate in ether, after standing, the upper solution was poured off, the precipitate was collected, and after drying, the polyethyleneimine modified by phenylboronic acid was obtained. 1 H NMR (300MHz, D 2 O): δ7.38(d, 2H), 7.10(d, 2H), 2.65-2.45(m, NCH 2 CH 2 N, NCH 2 CHPB), determined by proton nuclear magnetic resonance spectrum, the final product is PEI 1800 -pPB 5.4 .

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Abstract

The invention discloses a phenyloboricacid-modified cationic polymer, the structural formula is that (see lower right): wherein R is H or alkyl group containing one to ten carbons or substitution alkyl group containing nitrogen, oxygen, sulfur, chlorine, bromine or iodine; P is cationic polymer, the molecular weight Mw of P is from 400 to 500000, and n is more than or equal to 1 and less than or equal to 20. The preparation method is that: the phenyloboricacid with active groups and the cationic polymer are dissolved in methyl alcohol in N, N-dimethyl fomamide, and are reacted for 2-48 hours at the temperature of 20-60 DEG C for obtaining the phenyloboricacid-modified cationic polymer. The cationic polymer utilizes functional groups such as hydroxide radical and amino-group and the like in biomacromolecules such as phenyloboricacid group energy, protein, amylase, nucleic acid and the like to form reversible covalent-binding property, and improves the capacity of gene combination and cell carrying of carrier materials, so as to realize high-efficiency transfection of genes.

Description

technical field [0001] The invention relates to a cationic polymer modified by phenylboronic acid, its synthesis method and its application as a non-viral gene carrier. Background technique [0002] In recent years, genetic engineering has made remarkable achievements all over the world. This technology is to modify and recombine the gene of the organism by artificially "cutting" and "splicing" the DNA molecule outside the organism, and then introduce it into the recipient cell for asexual reproduction, so that the recombinant gene can be reproduced in the recipient cell. expression to produce the gene product required by humans. [0003] The application of genetic engineering in agricultural and animal husbandry production is mainly to cultivate new varieties of animals and plants with high yield, high quality or special purpose. Through genetic engineering technology, high-yield, stable yield and high-quality crops can be obtained, which can speed up the cultivation of n...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F26/02C08F8/42C08G69/48C08B37/08C12N15/63C12N15/82C12N15/85
Inventor 钟振林彭琪卓仁禧
Owner 常熟紫金知识产权服务有限公司
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