Fluorescent star-like polymer as well as preparation method and application thereof

A technology of star-shaped polymers and fluorescence, applied in other methods of inserting foreign genetic materials, chemical instruments and methods, luminescent materials, etc., can solve problems such as poor water solubility and affect applications, and achieve good biocompatibility and good applications value, low cytotoxic effect

Active Publication Date: 2013-06-26
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the disadvantage of poor water solubility directly affects its application in this field.

Method used

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  • Fluorescent star-like polymer as well as preparation method and application thereof
  • Fluorescent star-like polymer as well as preparation method and application thereof
  • Fluorescent star-like polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Example 1 Synthesis of star-shaped PAEMA (polyaminoethyl methacrylate) using ATRP polymerization method

[0045] 1.1 Synthesis of PDI-OH (compound 1)

[0046] 4Cl-PDI (1.70g, 2mmol), p-hydroxyphenethyl alcohol (2.76g, 20mmol) and K 2 CO 3 (1.38g, 10mmol) was added to a 250mL three-necked flask, and 80mL of NMP (N-methylpyrrolidone) was added to completely dissolve the reactant. Then pass nitrogen gas for 15 minutes, remove the air, put the flask into a 90°C oil bath to start the reaction, monitor the reaction degree by thin-layer chromatography, and stop the reaction after 24 hours. The reactant was precipitated in a mixed solution of water / methanol / concentrated hydrochloric acid (v / v / v=5:40:2), and NMP was removed by suction filtration to obtain a crude product. Using ethyl acetate as the eluent, it was separated by column chromatography to finally obtain 2.20 g of the product (compound 1), with a yield of 88%.

[0047]

[0048] Compound 1

[0049] 1.2 Synthesi...

Embodiment 2

[0078] Synthesis of embodiment 2 fluorescent star polymer 3 (n=50)

[0079]Add initiator compound 2 (17.6mg, 9.6μmol), catalyst CuBr (5.5mg, 38.4μmol), monomer Boc-AEMA (880mg, 3.84mmol) into a 25mL reaction tube, dissolve with 2mL 2-butanone, and process 3 times The freezing pumping process achieves the purpose of deoxygenation. The ligand DTB-bipy (20.6 mg, 76.8 μmol) is added under the protection of an inert gas, and then sealed with a rubber stopper. After stirring CuBr and the ligand are completely complexed, the reaction tube is Add to 65 ° C oil bath to start the reaction. After 50 minutes of reaction, the reactant passed through a neutral alumina column to remove the catalyst, and then precipitated three times in a mixed solvent of methanol and water (v:v=1:1), dried in vacuum to constant weight, and obtained 430 mg fluorescent star polymerization Object 3 (chain length n=50).

[0080] Deprotection of fluorescent star polymer 3 (n = 50): Take 400 mg fluorescent star ...

Embodiment 3

[0081] Synthesis of embodiment 3 fluorescent star polymer 3 (n=1)

[0082] Add initiator compound 2 (35.2 mg, 19.2 μmol), catalyst CuBr (11 mg, 76.8 μmol), monomer Boc-AEMA (880 mg, 3.84 mmol) into a 25 mL reaction tube, dissolve with 2 mL of 2-butanone, and freeze 3 times The pumping process achieves the purpose of deoxygenation. The ligand DTB-bipy (20.6 mg, 76.8 μmol) is added under the protection of an inert gas, and then sealed with a rubber stopper. After stirring CuBr and the ligand are completely complexed, the reaction tube is added The reaction was started in an oil bath at 65°C. After 5 minutes of reaction, the reactant was passed through a neutral alumina column to remove the catalyst, and then precipitated in a mixed solvent of methanol and water (v:v=1:1) for 3 times, and dried in vacuum to constant weight to obtain 52 mg fluorescent star polymerization Object 3 (chain length n=1).

[0083] Deprotection of fluorescent star polymer 3 (n = 1): Take 50 mg fluoresc...

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Abstract

The invention provides a method of a fluorescent star-like polymer which serves as a nucleic acid material carrier and is applied to live culture of cells and insects. A perylene derivative and an analogue thereof are taken as fluorescent nucleotides, and fluorescent star-like polymers which are in different generations and carries cation groups are prepared by adopting a 'divergent method'. The fluorescent star-like polymer has good biocompatibility and low cell toxicity, amino groups with positive charges can be carried at the periphery of a molecule, can enter live culture cells and can be combined with DNA or RNA with negative charges to form a stable complex, and the stable complex is taken as a carrier to carry and protect exogenous nucleic acid to enter live culture cells. Mixture of the carrier and the DNA or RNA is fed in food or injected into a body cavity, the carrier can quickly carry the DNA or RNA to enter cells of a live insect in vivo, and effect exertion of nucleic acid and normal expression of genes interfering insect targets are facilitated, so that insects are abnormal in development until the insects fall ill or die.

Description

technical field [0001] The invention relates to the field of compound preparation and gene carrier, in particular to a fluorescent star polymer, its preparation method and application. Background technique [0002] With the development of advanced biotechnology therapy, gene transfer system is becoming more and more important. At present, the commonly used gene vectors mainly include viral vectors and non-viral vectors. Although viral vectors have high transfection efficiency, they have safety problems such as immune response and cytotoxicity, which limit their application range. In recent years, the development of polymer materials in the gene drug carrier system is very rapid. As a new type of non-viral carrier, it overcomes the defects of viral vectors and opens up many new fields, which has attracted widespread attention. Among them, the non-viral vector system mainly includes cationic polymers, biodegradable polymers, multi-complex liposomes, thermosensitive polymers a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F120/36C08F8/00C07D471/06C09K11/06C12N15/87A01K67/033
Inventor 沈杰何碧程尤树森尹梅贞
Owner CHINA AGRI UNIV
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