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Water-soluble hyperbranched fluorescent polymer and preparation method and applications thereof

A fluorescent polymer, water-soluble technology, applied in the field of hyperbranched polymer synthesis, to achieve the effects of simple synthesis, broad biological application prospects, and simple product purification

Active Publication Date: 2014-01-29
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently synthesized hyperbranched polymers with peryleneimide derivatives as fluorescent cores have good water solubility and biocompatibility, however, such hyperbranched polymers with peryleneimides as cores are electrically neutral , there is no relevant report on applying them to drug carriers and gene carriers, etc.

Method used

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  • Water-soluble hyperbranched fluorescent polymer and preparation method and applications thereof
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  • Water-soluble hyperbranched fluorescent polymer and preparation method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1 Synthesis of water-soluble hyperbranched fluorescent polymer (PDI-HPAA) by Michael addition method

[0040] 1. Add 200.0mg of compound 1 (0.16mmol) and 246.5mg of N,N-methylenebisacrylamide (MBA) (1.6mmol) into 5mL of a mixed solvent of methanol and water with a volume ratio of 4:1, under nitrogen Stir at room temperature for 2 h under atmosphere, then react at 50°C for 50 h, wait for the reaction temperature to drop to room temperature, wash with 50 mL of a mixture of diethyl ether and n-hexane with a volume ratio of 3:1 repeatedly for 3 times, and dry in vacuo to obtain a red solid intermediate product 2. Yield 95%. 1 HNMR(400MHz,DMSO)δ8.62(d,J=51.8Hz,16H),7.94(s,4H),7.43(s,2H),7.25(s,12H),6.98(s,8H),6.17( d,J=45.1Hz,16H),5.59(s,8H),4.45(s,16H),3.38(s,16H),2.70(s,20H),2.24(s,16H),1.10(s,24H ).

[0041] 2. Add 248.5mg of intermediate product 2 (0.1mmol) and 129.0mg of aminoethylpiperazine (APEZ) (1.0mmol) to 6.0mL of a mixed solvent of methanol and water w...

Embodiment 2

[0047] Embodiment 2 live cell uptake experiment

[0048] The water-soluble hyperbranched fluorescent polymer synthesized in Example 1, namely compound 3, compound 4, and PDI-HPAA were incubated with living cells, and it was found that it took a long time for compounds 3 and 4 to enter living cells, while PDI-HPAA could quickly Efficiently enters living cells, exhibits good biocompatibility and low toxicity. 2μM carrier molecule PDI-HPAA can penetrate the cell membrane of living cells and enter the cells after incubation for about 1 hour.

Embodiment 3

[0049] Embodiment 3 gene transfection experiment

[0050] Using the water-soluble hyperbranched fluorescent polymer PDI-HPAA complexed DNA transfected in Example 1 to transfect living cells, the ratio of DNA and PDI-HPAA complexed, that is, the number of ammonium salts at the end of the hyperbranched macromolecule and the ratio of the phosphate radical of the DNA molecule were investigated. Effect of number ratio (N / P) on transfection experiments. By studying the DNA and PDI-HPAA complexes transfected cells with different N / P ratios (2:1, 4:1, 8:1), it was found that the carrier molecule PDI-HPAA was in all N / P ratio conditions All showed high transfection activity.

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Abstract

The invention discloses a water-soluble hyperbranched fluorescent polymer and a preparation method thereof, belonging to the field of hyperbranched polymer synthesis technology. The water-soluble hyperbranched fluorescent polymer serves as a genetic carrier for efficiently and quickly transfecting viable cells. An amino fuctional group-carrying hyperbranched fluorescent polymer is prepared by adopting a multi-step feeding method through a Michael addition reaction. The hyperbranched fluorescent polymer synthesized by adopting the method has excellent water solubility and biocompatibility, can enter viable cells, and can be combined with electronegative DNA or RNA through electrostatic acting force, and therefore as a genetic carrier, the hyperbranched fluorescent polymer is capable of carrying an exogenous nucleic acid member DNA or RNA into cells. The preparation method has the advantages of simple and convenient synthesis, high efficiency, simple product purification and the like, and the synthesized water-soluble hyperbranched fluorescent polymer is safe and low-toxicity, excellent in water solubility, and high in fluorescent quantum yield; and as an efficient genetic carrier, the water-soluble hyperbranched fluorescent polymer can be applied to scientific research and genetic therapy in the biomedical field,.

Description

technical field [0001] The invention belongs to the technical field of hyperbranched polymer synthesis, and particularly relates to a water-soluble hyperbranched fluorescent polymer and a preparation method thereof, which can be used as a gene carrier to efficiently and rapidly transfect living cells. Background technique [0002] With the development of advanced biotechnology therapies, gene transfer systems have become more important. At present, the commonly used gene delivery systems mainly include viral vectors and non-viral vectors. Viral vectors have poor safety due to their own structure, which can produce immune response and cytotoxicity, thus limiting their application range. The development of safe non-viral gene vectors has always been a hot research topic in the field of biomaterials. At present, the non-viral gene carrier systems that have been studied more mainly include cationic multi-polymer carriers, biodegradable polymer systems, multi-complex liposome sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G83/00C09K11/06C12N15/87
Inventor 尹梅贞许泽军何碧程刘柯兰沈杰
Owner BEIJING UNIV OF CHEM TECH
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