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Poly-valerolactone type amphiphilic polymer based on tetraphenyl ethylene as well as preparation method and application of poly-valerolactone type amphiphilic polymer

A technology of polyvalerolactone and tetraphenylethylene, which is applied in the field of polymer design and preparation, and can solve the problems of great difference in transfection efficiency and single function

Active Publication Date: 2019-12-03
BEIJING NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, their transfection efficiency is still far from that of viral vectors, and the polyester vectors reported so far have a single function, which is used as a DNA condensation and transport tool.

Method used

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  • Poly-valerolactone type amphiphilic polymer based on tetraphenyl ethylene as well as preparation method and application of poly-valerolactone type amphiphilic polymer
  • Poly-valerolactone type amphiphilic polymer based on tetraphenyl ethylene as well as preparation method and application of poly-valerolactone type amphiphilic polymer
  • Poly-valerolactone type amphiphilic polymer based on tetraphenyl ethylene as well as preparation method and application of poly-valerolactone type amphiphilic polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] A polyvalerolactone type amphiphilic polymer based on tetraphenylethylene, the structural formula (I) of the compound is as follows:

[0051]

[0052] In formula (I), R 1 is a sulfur-containing substituent, R 2 is a substituted macrocyclic polyamine [12]aneN 3 group, m, n are positive integers.

[0053] Among them, when R 1 for R2 for Denoted as polymer 1;

[0054] When R 1 for a=6, R 2 for Denoted as polymer 2;

[0055] When R 1 for a=10,R 2 for Denoted as polymer 3;

[0056] Concrete synthetic route is as follows:

[0057]

[0058]

[0059] The synthetic procedure of compound 1-1: have 3.0g (16.5mmol) [12]aneN to dissolve 3 Add 10.0 mL of 1,3-dibromopropane (98.5 mmol) to 30.0 mL of the precursor solution in acetonitrile, stir and reflux overnight; stop the reaction when a large amount of white solid appears in the bottle. Acetonitrile was removed by rotary evaporation under reduced pressure to obtain a yellow solid-liquid mixture. Ad...

Embodiment 2

[0066] Polymers 1, 2 and 3 were configured into aqueous solutions of different concentrations, and the fluorescence intensity of the aqueous solutions of polymers 1 to 3 was measured; the maximum value of the fluorescence intensity varied with the concentration (10 -6 ~10 -1 mg / mL) change trend graph, get figure 1 A~ figure 1 C, at figure 1 In A-1C, the X-axis is the solution concentration, and the Y-axis is the fluorescence intensity.

[0067] figure 1 A~1C are the determination diagrams of the critical micelle concentration of polymers 1~3 respectively, from figure 1 From A to 1C, it can be seen that the critical micelle concentrations of compounds 1 to 3 are very low, and the critical micelle concentrations of compounds 1 to 3 are 9.6 μg / mL, 0.5 μg / mL, and 1.1 μg / mL, respectively

Embodiment 3

[0069] Prepare solutions of different concentrations of 1 / DOPE, 2 / DOPE and 3 / DOPE (1:2, molar ratio), form complexes with pGL-3 plasmid DNA, incubate at 37°C for 0.5 hours, and then Add it into different gel wells, and carry out DNA agarose gel retardation experiment to obtain the aggregation of DNA by different concentrations of polymers.

[0070] figure 2 A~2C are respectively the agarose gel retardation experiment results of the pGL-3DNA of the polymers 1 / DOPE, 2 / DOPE and 3 / DOPE of the present invention; figure 2 It can be drawn that the tetraphenylethylene-based polyvalerolactone amphiphilic polymer of the present invention can effectively condense DNA to form nanoparticles, and the minimum blocking concentrations of polymers 1 to 3 are respectively: 40 μg / mL, 30 μg / mL and 40 μg / mL.

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Abstract

The invention discloses a poly-valerolactone type amphiphilic polymer based on tetraphenyl ethylene as well as a preparation method and an application of the poly-valerolactone type amphiphilic polymer. The disclosed compound is mainly prepared through a Michael reaction, an ROP reaction and a thio-ene click reaction, and the structure of the compound is confirmed by nuclear magnetism and mass spectrum. The poly-valerolactone type amphiphilic polymer has an aggregation-induced emission (AIE) effect, gel electrophoresis, dynamic light scattering, SEM and other test means prove that the polymercan aggregate DNA, and the diameter of formed nanoparticles is smaller than 200 nm. In-vitro transfection experiments prove that liposome formed by the poly-valerolactone type amphiphilic polymer anddioleoyl phosphatidyl ethanolamine (DOPE) can be used as a non-virogene vector.

Description

technical field [0001] The invention relates to the design and preparation of polymers, in particular to a tetraphenylethylene-based polyvalerolactone-type amphiphilic polymer and its preparation method and application. Background technique [0002] Gene therapy has received a lot of attention in diseases such as genetic defects and cancer. Because both DNA and cell membrane are negatively charged, there is electrostatic repulsion, and there are nucleolytic enzymes in the cytoplasm, it is very difficult for naked DNA to be taken up by cells. Therefore, it is particularly important to develop a safe and effective gene transport tool, that is, a gene carrier. At present, non-viral gene vectors have received more attention than viral vectors. Non-viral vectors include liposomes, polymers, nanoparticles, and the like. Cationic polymers have the advantages of good biocompatibility and safety, easy modification and large-scale production. However, it is limited by low transfec...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/688C08G63/91C08G63/08C08G63/78C09K11/06C12N15/88
CPCC08G63/08C08G63/6882C08G63/78C08G63/912C09K11/06C12N15/88
Inventor 卢忠林刘旭英杨静波马乐乐刘名轩
Owner BEIJING NORMAL UNIVERSITY
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