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A novel cationic polymer used as a non-viral gene carrier and its preparation method and use

A kind of cationic polymer and polymer technology, applied in the direction of using carrier to introduce foreign genetic material, gene therapy, medical preparations of non-active ingredients, etc., can solve problems such as degradation, in vivo application restrictions, and failure

Inactive Publication Date: 2011-11-30
SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

[0003] At present, the new cationic polymer gene delivery system has become the main direction of the design and development of gene non-viral vectors, for example, polylysine (PLL), polyethyleneimine (PEI), polyamide-amine dendrimers , polydimethylaminoethyl methacrylate, chitosan and polycationic cyclodextrin and other structurally modified derivatives, especially the research reports on PEI with high transfection efficiency due to its "proton sponge" effect Most, but its in vivo application is limited because it cannot be degraded in vivo and has great toxicity to cells

Method used

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  • A novel cationic polymer used as a non-viral gene carrier and its preparation method and use

Examples

Experimental program
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Embodiment 1

[0060] Embodiment 1 contains the synthesis of the alkynylated diethylenetriamine monomer (numbering A) of Boc

[0061] Diethylenetriamine (1.03g, 10mmol) was dissolved in dichloromethane DCM (50mL). After cooling in an ice bath, ethyl trifluoroacetate (2.95g, 21mmol) was added dropwise, and stirred in an ice bath for 1h. After the temperature of the reaction solution rose to room temperature and then stirred for 1 h, di-tert-butyl dicarbonate Boc dissolved in an appropriate amount of DCM was added dropwise. 2 O (3.28g, 15mmol) solution and triethylamine TEA (1.52g, 15mmol) solution were stirred at room temperature overnight. with saturated NaHCO 3 Washed with saturated brine, anhydrous Na 2 SO 4 dry. After concentration, it was recrystallized with DCM / n-hexane system. The recrystallized material (2.00g) contained K 2 CO 3 (1.80 g) was refluxed in methanol / water (volume ratio 20:1) system for 4 h, methanol was spin-dried, and the residue was extracted with DCM (3×100 mL)...

Embodiment 2

[0063] Embodiment 2 contains the synthesis of the alkynylated triethylenetetramine monomer (numbering B) of Boc

[0064] Triethylenetetramine (1.46g, 10mmol) was dissolved in DCM (50mL) solution, and after cooling in an ice bath, ethyl trifluoroacetate (2.95g, 21mmol) was added dropwise, and stirred in an ice bath for 1h. After the temperature of the reaction solution rose to room temperature and then stirred for 1 h, Boc dissolved in an appropriate amount of DCM was added dropwise. 2 O (5.68g, 26mmol) solution and TEA (2.63g, 26mmol) solution were stirred at room temperature overnight. with saturated NaHCO 3 Washed with saturated brine, anhydrous Na 2 SO 4 dry. After concentration, it was recrystallized with DCM / n-hexane system. The recrystallized material (2.00g) contained K 2 CO 3 (1.80 g) was refluxed in methanol / water (volume ratio 20:1) system for 4 h, methanol was spin-dried, and the residue was extracted with DCM (3×100 mL). The combined organic phases were was...

Embodiment 3

[0066] Synthesis of embodiment 3 azide diethylene glycol monomer (numbering 1)

[0067] Diethylene glycol (2.12 g, 20 mmol) was dissolved in DCM (250 mL) and cooled in an ice bath. Add p-toluenesulfonyl chloride (7.62g, 42mmol), TEA (4.25g, 42mmol) and 4-dimethylaminopyridine DMAP (0.12g, 0.1mmol) sequentially, stir in ice bath for 1h, and then stir at room temperature for 12h. The reaction solution was sequentially washed with saturated NaHCO 3 (2×300mL) and saturated brine (300mL) for washing, anhydrous Na 2 SO 4dry. After concentration, it was recrystallized with DCM / n-hexane system. Dissolve the recrystallized product (4.1 g, 10 mmol) in acetone, add sodium azide (1.9 g, 30 mmol), and reflux for 48 h. The solvent was concentrated, separated by silica gel column chromatography, and eluted with petroleum ether / ethyl acetate (volume ratio 2:1) to obtain monomer 1 ( 1 HNMR (DMSO-d 6 ): 2.87(s, 4H), 2.70(s, 4H)). The structural formula of monomer 1 is as follows:

[00...

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Abstract

The invention discloses a novel cationic polymer used for a non-virus type gene carrier, its preparation method and its purpose. The cationic polymer of the present invention has a following structure in a formula I. The method of the cationic polymer provided in the present invention comprises the following steps: polymerizing a monomer containing alkynyl group at an end thereof and a monomer containing azido group at an end thereof through a monovalent copper ions-catalyzed alkynyl-azido cycloaddition reaction, and simultaneously removing a protective group to generate the cationic polymer with a 1,2,3-triazolyl group structure. The polymer of the present invention reserves a high transfection efficiency equivalent with PEI, and substantially reduces the cytotoxicity of PEI, the non-virus type gene carrier prepared by the polymer has the characteristics of high biological compatibility, low toxicity, high transfection efficiency and the like.

Description

technical field [0001] The present invention relates to a novel cationic polymer and its preparation method and application, and also relates to the nanocomposite composed of the novel cationic polymer and nucleic acid as well as its preparation method and application. Background technique [0002] Gene therapy refers to the introduction of normal genes or genes with therapeutic effects into target cells in a certain way to correct gene defects or exert therapeutic effects, so as to achieve the purpose of treating diseases. Because of its many unique advantages, gene therapy has had a profound impact on the treatment of major human diseases since its inception. However, the core problem of gene therapy is that the ideal gene carrier has not been found yet. Gene vectors researched and developed so far are mainly divided into two categories: viral vectors and non-viral vectors. Among them, viral vectors, such as various retroviruses, adenoviruses, herpes viruses, and adeno-as...

Claims

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Application Information

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IPC IPC(8): C08G73/06C08L79/04C12N15/63A61K47/34A61K48/00
Inventor 李亚平高瑜张志文顾王文
Owner SHANGHAI INST OF MATERIA MEDICA CHINESE ACAD OF SCI
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