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Methacrylic ester polymer, compounds thereof as well as preparation methods and application of all

A technology of methacrylate and compound, which is applied in the field of preparation method and its application as a gene carrier, can solve problems such as difficulty in determining possible toxicity

Inactive Publication Date: 2010-03-03
SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The possible toxicity of colloidal gold is difficult to ascertain due to the very small amount of colloidal gold used for delivery

Method used

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  • Methacrylic ester polymer, compounds thereof as well as preparation methods and application of all
  • Methacrylic ester polymer, compounds thereof as well as preparation methods and application of all
  • Methacrylic ester polymer, compounds thereof as well as preparation methods and application of all

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0039] Example 1: Synthesis of ethyl xanthate

[0040] Add 100 mL of chloroform, 0.1 mol of bromoethane, and 0.11 mol of ethyl xanthate sodium into a 500 mL round-bottomed flask, stir at room temperature for 72 hours, separate by filtration under reduced pressure, wash with chloroform, and saturated sodium bicarbonate. Dry over magnesium sulfate and distill off the solvent to obtain a yellow oily liquid, which is separated by silica gel column chromatography, and the eluent is a mixed solvent of hexane and ethyl acetate (volume ratio 90:10) to obtain ethyl xanthate.

[0041] 1 H NMR (CDCl 3 ): 1.11, 3.57, 2.91, 1.31

[0042] 13 C NMR (CDCl 3 ): 13.5, 60.5, 72.0, 24.5, 15.5

[0043] synthetic route:

example 2

[0044] Example 2: Synthesis of xanthate-based poly-2-dimethylaminoethyl methacrylate (OPDMAEMA)

[0045] Add 1 g of 2-dimethylaminoethyl methacrylate (DMAEMA), 4 mg of azobisisobutyronitrile (AIBN), 80 mg of ethyl xanthate, and 2 mL of tetrahydrofuran into a 5 mL round bottom flask, [ethyl yellow Ethyl orthoate]: [AIBN]=20. Freeze with liquid nitrogen to remove oxygen, then seal under reduced pressure and remove oxygen, and react in a water bath at 70°C for 48 hours. After cooling to room temperature, excess hexane was added to precipitate and isolate the polymer-xanthate-based poly(2-dimethylaminoethyl)methacrylate (OPDMAEMA). for polymer 1 H NMR characterization, D 4 -Methanol and D-chloroform as solvents.

[0046] 1 H NMR (CDCl 3 ): 1.11, 3.57, 1.69, 1.33, 0.96, 2.27, 4.18, 2.64

[0047] 13 C NMR (CDCl 3 ): 13.5, 60.5, 172.0, 50.6, 39.7, 16.4, 14, 22.1, 41.2, 58.2, 66.1, 174.5

example 3

[0048] Example 3: Preparation of mercapto-terminated poly-2-dimethylaminoethyl methacrylate (MPDMAEMA) by OPDMAEMA

[0049] Dissolve OPDMAEMA in tetrahydrofuran solution, add a few drops of ammonium persulfate solution, fill with nitrogen for 30 minutes, add n-butylamine, and stir for 5 hours under nitrogen protection. The reaction mixture was added into a 10-fold excess of hexane, precipitated and filtered to obtain mercapto-terminated poly 2-dimethylaminoethyl methacrylate (MPDMAEMA).

[0050] 1 H NMR (CDCl 3 ): 1.5, 1.9, 1.33, 0.96, 1.69, 4.18, 2.64, 2.27

[0051] 13 C NMR (CDCl 3 ): 44.9, 42.4, 16.4, 13.6, 24.3, 174.5, 65.7, 58.2, 41.2

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Abstract

The invention discloses a mercaptyl-terminated (2-dimethylamino ethyl) polymethacrylic ester polymer, a self-assembled and modified nano-gold compound (PDMAEMAGNPs) of the polymer as well as a compound of the polymer and plasmid DNA; and the invention also discloses preparation methods of the polymer and the compounds as well as the application of all in carrier as genes. When the concentration ofthe compounds of PDMAEMAGNPs and GFP DNA (green fluorescent protein expression DNA) is 30Mug / mL, the transfection efficiency to HEK 293T cell is 30 percent, and the survival rate to HEK 293T cell, HeLa cell and 293 cell is more than 80 percent. The PDMAEMAGNPs / CpG ODN (human CpG oligodeoxynucleotide) compound has remarkable effects in gene therapy in vitro and in vivo. The suppression ratio to tumor growth of the PDMAEMAGNPs / p53 DNA (tumor suppressor gene) is 30-37 percent.

Description

technical field [0001] The present invention relates to a kind of methacrylate polymer, the nano-gold complex of the polymer and the complex of plasmid DNA thereof, and the present invention also relates to the preparation method of these polymers, the complex and their application as gene carriers . Background technique [0002] Gold nanoparticles have been studied for 150 years. Gold nanoparticles have the advantages of strong oxidation resistance, good biocompatibility, high density and good photoelectric properties. Bioanalysis methods based on gold nanoparticles have achieved many results. Gold nanoclusters (Au 2 MPCs) interact with biological substances such as nucleic acids, proteins, and cell membranes, and can be applied to various research fields of biomedicine. [0003] CytImmune Sciences of the United States and OctoPlus of the Netherlands have cooperated to develop colloidal gold nanoparticles as a possible delivery technology for the anti-cancer protein TNF ...

Claims

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Application Information

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IPC IPC(8): C08F120/34C08F8/34C08F8/42C12N15/63
Inventor 于伯章
Owner SHANGHAI INST OF APPLIED PHYSICS - CHINESE ACAD OF SCI
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