Tannic acid modified polyethyleneimine compound, preparation method thereof and gene vector

A polyethylenimine and tannic acid technology, applied in the field of biomedicine, can solve the problems of restricting the development and application of gene carriers, unsatisfactory cytotoxicity, complex synthesis steps, etc., and achieves reduced synthesis cost, low toxicity, and fewer synthesis steps. Effect

Active Publication Date: 2020-07-10
WUHAN POLYTECHNIC UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the currently reported graft-modified PEI gene carriers are cationic copolymers obtained by modifying PEI using natural and synthetic polymer materials, such as PAMAM, PLL, and chitosan. The cytotoxicity is not ideal, and the synthesis steps are more complex, which also leads to higher synthesis costs, which limits the development and application of gene vectors

Method used

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  • Tannic acid modified polyethyleneimine compound, preparation method thereof and gene vector
  • Tannic acid modified polyethyleneimine compound, preparation method thereof and gene vector
  • Tannic acid modified polyethyleneimine compound, preparation method thereof and gene vector

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preparation example Construction

[0053] In the present embodiment, the preparation method of the tannic acid modified polyethyleneimine compound comprises the following steps:

[0054] Step S10, after mixing tannic acid, anhydrous tetrahydrofuran and triethylamine, adding chloroacetyl chloride, acetylation reaction to generate intermediate M;

[0055] Step S20, after mixing the intermediate M with anhydrous tetrahydrofuran, adding a tetrahydrofuran solution of polyethyleneimine, and stirring at 25-45°C to generate tannic acid-modified polyethyleneimine compound A;

[0056] Wherein, the intermediate M has the structure shown in the following structural formula (II):

[0057]

[0058] in,

[0059]

[0060] Its synthetic route is as follows:

[0061]

[0062] The method of the present invention uses tannic acid as a starting material, first prepares the intermediate M through chloroacetylation reaction, and then reacts the intermediate M with PEI to obtain a tannic acid-modified polyethyleneimine comp...

Embodiment 1

[0086] Add 2.0g of tannic acid, 25mL of anhydrous tetrahydrofuran, and 5mL of triethylamine into the round-bottomed flask in turn, and stir evenly. Under the condition of an ice-water bath, 28 mol of chloroacetyl chloride was slowly added dropwise to the above system. After the dropwise addition, the ice-water bath was removed, and the stirring reaction was continued at 35° C. for 20 h. The reaction system was transferred to a dialysis bag with a molecular weight cut-off of 2000, and dialyzed with running water for 24 hours, and then dialyzed with deionized water for 12 hours. During deionized water dialysis, the dialyzate was renewed every 2 hours. After the dialysis, the retentate was collected for low-temperature vacuum concentration, and then the concentrated product was pre-frozen at -20°C for 24 hours, and finally placed in a freeze dryer for 24 hours. , to obtain intermediate M.

[0087] Add 2.0 g of the above-obtained intermediate M and 25 mL of anhydrous tetrahydrofu...

Embodiment 2

[0090] Add 2.0g of tannic acid, 25mL of anhydrous tetrahydrofuran, and 5mL of triethylamine into the round-bottomed flask in turn, and stir evenly. Under the condition of ice-water bath, 28 mol of chloroacetyl chloride was slowly added dropwise to the above system. After the dropwise addition, the ice-water bath was removed, and the stirring reaction was continued at 25° C. for 24 h. The reaction system was transferred to a dialysis bag with a molecular weight cut-off of 2000, and dialyzed with running water for 24 hours, and then dialyzed with deionized water for 12 hours. During deionized water dialysis, the dialyzate was updated every 2 hours. After the dialysis, the retentate was collected for low-temperature vacuum concentration, and then the concentrated product was pre-frozen at -18°C for 26 hours, and finally placed in a freeze dryer for 24 hours. , to obtain intermediate M.

[0091] Add 2.0 g of the above-obtained intermediate M and 25 mL of anhydrous tetrahydrofuran...

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Abstract

The invention discloses a tannic acid modified polyethyleneimine compound, a preparation method thereof and a gene vector, and relates to the technical field of biological medicine. The tannic acid modified polyethyleneimine compound has a structure shown as the following structural formula (I). According to the invention, tannic acid is used as a modification group to modify polyethyleneimine soas to obtain a tannic acid modified polyethyleneimine compound with a structure shown as the structural formula (I). The tannic acid modified polyethyleneimine compound can effectively coagulate DNA to form a nano-composite, can be used as a gene vector to transport DNA, and has the advantages of low toxicity, good biocompatibility and good water solubility due to the adoption of natural polyphenol tannic acid with good biocompatibility and low cytotoxicity as the modification group. Besides, the compound can be obtained through two-step reaction, the synthesis steps are few, the reaction operation is simple, and the synthesis cost is reduced.

Description

technical field [0001] The invention relates to the technical field of biomedicine, in particular to a tannic acid-modified polyethyleneimine compound, a preparation method thereof and a gene carrier. Background technique [0002] Gene therapy refers to the introduction of normal genes or therapeutic genes into target cells to correct gene defects or exert therapeutic effects, so as to achieve the purpose of preventing or treating diseases. As a brand-new treatment method, gene therapy has the advantages of high targeting, high efficiency and small side effects, showing great application potential. Gene carrier is the key to limit the development of gene therapy. [0003] Polyethyleneimine (PEI) has a high content of amino groups in its molecular structure, and has primary, secondary and tertiary amines with different pKa values, which makes PEI have the ability to absorb protons under a wide range of pH conditions. That is, the proton sponge effect is conducive to the esc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G73/02C12N15/87
CPCC08G73/0206C12N15/87
Inventor 关金涛曾志伟刘梁付曼君
Owner WUHAN POLYTECHNIC UNIVERSITY
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