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A kind of poly(beta-amino ester) type polymer gene carrier containing disulfide bond and its synthesis method and application

A technology of gene carrier and amino ester, which is applied in the field of cluster polymer non-viral gene carrier and its synthesis, can solve the problems of inability to fully release DNA in cells and increase cytotoxicity, and achieve improved transfection effect and cytotoxicity Effects of reducing and increasing transfection efficiency

Active Publication Date: 2018-12-14
NANJING UNIV OF SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In the past, the focus of high-efficiency transfection systems mainly focused on increasing the molecular weight, positive charge and branching degree of the polymer. However, if the positive charge is too high, the nanoparticles formed after encapsulating DNA will be too compact and cannot be absorbed in the cell after endocytosis. In addition, the large molecular weight will also lead to the increase of cytotoxicity

Method used

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  • A kind of poly(beta-amino ester) type polymer gene carrier containing disulfide bond and its synthesis method and application
  • A kind of poly(beta-amino ester) type polymer gene carrier containing disulfide bond and its synthesis method and application
  • A kind of poly(beta-amino ester) type polymer gene carrier containing disulfide bond and its synthesis method and application

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Experimental program
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Embodiment 1

[0038] Step 1. Dissolve 2-hydroxyethyl disulfide (3mmol) in THF solution (10mL), add isocyanoethyl acrylate (6mmol), add dropwise two drops of dibutyltin dilaurate (catalyst), at 40°C The reaction was stirred for 24h. After the reaction, the mixed solution was rotary evaporated to obtain a crude product, which was then purified by column chromatography (ethyl acetate / petroleum ether=1 / 1).

[0039] S (yield 95%): 1 H NMR (500MHz, DMSO) δ7.37 (t, J = 5.6Hz, 2H), 6.33 (dd, J = 17.3, 1.3Hz, 2H), 6.14 (dd, J = 17.3, 10.4Hz, 2H), 5.93 (dd,J=10.4,1.2Hz,2H),4.16(t,J=6.3Hz,4H),4.08(t,J=5.5Hz,4H),3.24(q,J=5.6Hz,4H),2.92 (t, J=6.3Hz, 4H).

[0040]Step 2, the diacrylate monomer compound S (2.2 mmol) synthesized in step 1 and 5-amino-1-pentanol (2 mmol) were stirred and reacted for 24 hours without solvent, and the reaction temperature was set at 70 ° C to generate acrylic acid Ester terminated poly(β-amino ester) SF. SF (yield 100%): 1 H NMR (500MHz, DMSO) δ6.35 (CH 2 =CH-), 6.14 (...

Embodiment 2

[0043] The difference between embodiment 2 and embodiment 1 is step 2, and step 1 and step 3 are the same as embodiment 1.

[0044] Step 2, the diacrylate monomer compound S (2.2 mmol) synthesized in step 1 and 5-amino-1-pentanol (2 mmol) were stirred and reacted for 48 hours without solvent, and the reaction temperature was set at 70 ° C to generate acrylic acid Ester terminated poly(β-amino ester) SF.

Embodiment 3

[0046] The difference between embodiment 3 and embodiment 1 is step 2, and step 1 and step 3 are the same as embodiment 1.

[0047] Step 2, the diacrylate monomer compound S (2.2 mmol) synthesized in step 1 and 5-amino-1-pentanol (2 mmol) were stirred and reacted for 24 hours without solvent, and the reaction temperature was set at 90 ° C to generate acrylic acid Ester terminated poly(β-amino ester) SF.

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Abstract

The invention discloses a disulfide bond containing poly(beta-amino ester) polymer gene carrier. The poly(beta-amino ester) polymer is a cationic polymer prepared through addition polymerization, is capable of being combined with plasmid DNA with negative charges through the electrostatic interaction, and thus delivers DNA into cells to realize genetic transmission. By introducing disulfide bonds into the poly(beta-amino ester) polymer, the poly(beta-amino ester) polymer has an oxidation-reduction responding mechanism in cells, thus the polymer degradation is assisted, and DNA can be fully released in the cells. The results of cytotoxicity tests and cell transfection experiments show that the disulfide bond containing poly(beta-amino ester) polymer gene carrier has low cytotoxicity and high transfection efficiency, which is obviously higher than that of common commercial gene transfection reagents. The provided poly(beta-amino ester) polymer gene carrier is a low toxic and high efficient non-virus gene carrier, and has a very good application prospect.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to a poly(β-amino ester) polymer non-viral gene carrier containing a disulfide bond and a synthesis method and application thereof. technical background [0002] Gene therapy refers to the introduction of normal foreign genes into target cells to correct or compensate diseases caused by gene defects and abnormalities, so as to achieve therapeutic purposes. The success of gene therapy depends largely on the appropriate gene delivery vehicle. Nowadays, most people use viral vectors to transfer genes in the gene therapy system. However, viral vectors have many shortcomings that cannot be ignored, including strong immune response, limited gene loading capacity, and difficulty in large-scale production. Therefore, non-viral vectors have attracted extensive attention and research as an alternative vector with easy preparation, high stability, small immune response, and strong pla...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G73/02C12N15/63A61K48/00
Inventor 杨莉刘玉成蒋伏林齐晓亮魏威董伟
Owner NANJING UNIV OF SCI & TECH
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