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Water-soluble degradable live cell fluorescent imaging material of non-conjugated structure as well as preparation method and application thereof

A fluorescent imaging and non-conjugated technology, which is applied in the direction of luminescent materials, material analysis and material analysis through optical means, can solve the problem that PCG does not have any fluorescent properties, achieve simple preparation methods, improve biological activity, and improve fluorescent properties Effect

Pending Publication Date: 2018-11-30
XI AN JIAOTONG UNIV
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Problems solved by technology

Poly-1,8-octanediol citrate-polyethylene glycol (PCG) is a polymer formed by condensation of citric acid, 1,8-octanediol and polyethylene glycol under high temperature conditions. Non-toxic, good biocompatibility, simple reaction and no introduction of impurities, and since citric acid has three carboxyl groups, it can be further modified, but unmodified PCG does not have any fluorescent properties, so if it can be modified , so that it has the ability to emit fluorescence, and its application in biological imaging will be greatly improved

Method used

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  • Water-soluble degradable live cell fluorescent imaging material of non-conjugated structure as well as preparation method and application thereof
  • Water-soluble degradable live cell fluorescent imaging material of non-conjugated structure as well as preparation method and application thereof
  • Water-soluble degradable live cell fluorescent imaging material of non-conjugated structure as well as preparation method and application thereof

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preparation example Construction

[0034] The invention is committed to preparing a water-soluble non-conjugated structure degradable living cell fluorescence imaging material with good biocompatibility and fluorescence characteristics, so that it has the ability of living cell fluorescence labeling. The preparation method comprises the following steps:

[0035] 1) Preparation of PCG prepolymer: thermally polymerize citric acid and diol with a molar ratio of 1:1 at 140-160°C under nitrogen or vacuum conditions to obtain PCG prepolymer. The diols are 1,8-octanediol and polyethylene glycol (PEG). The structural formula of PCG prepolymer is as follows (as figure 1 ):

[0036]

[0037] 2) Preparation of PCGA polymer: react PCG prepolymer and amino acid with a molar ratio of 1:(3~10) in 50mM MES buffer solution with pH 5~6, using EDC and NHS as catalysts to obtain PCGA polymer. The amino acids are L-arginine and polylysine. The structural formula is as follows

[0038]

[0039] Preparation of PCGS polyme...

Embodiment 1

[0045] 1) Preparation of PCG prepolymer: Add citric acid, 1,8-octanediol and polyethylene glycol into a round bottom flask at a molar ratio of 1:0.7:0.3, stir in an oil bath at 160°C under nitrogen Melting; after the reaction monomers citric acid, 1,8-octanediol and polyethylene glycol are all melted, the temperature is immediately lowered to 140°C, and the reaction is carried out under vacuum for 5 hours. The reaction product was dialyzed and purified in deionized water for 2 days, and freeze-dried for later use;

[0046] 2) Preparation of PCGR (3) polymer: Weigh 1 mmol of polycitrate (PCG) in 30 mL, 50 mM, pH 5-6 MES buffer and stir to dissolve completely, then add 4 mmol of EDC, and stir at room temperature for 30 min , followed by adding 4mmol NHS, stirring at room temperature for 12h, finally adding 3mmol L-arginine, stirring at room temperature for 12h, the product was purified by dialysis in deionized water for 2 days to remove unreacted monomers and catalysts EDC and N...

Embodiment 2

[0049] 1) Preparation of PCG prepolymer: Add citric acid, 1,8-octanediol and polyethylene glycol into a round bottom flask at a molar ratio of 1:0.7:0.3, stir in an oil bath at 160°C under nitrogen Melting; after the reaction monomers citric acid, 1,8-octanediol and polyethylene glycol are all melted, the temperature is immediately lowered to 140°C, and the reaction is carried out under vacuum for 5 hours. The reaction product was dialyzed and purified in deionized water for 2 days, and freeze-dried for later use;

[0050] 2) Preparation of PCGR (5) polymer: Weigh 1 mmol of polycitrate (PCG) in 30 mL, 50 mM, pH 5-6 MES buffer and stir to dissolve completely, then add 4 mmol of EDC, and stir at room temperature for 30 min , followed by adding 4mmol NHS, stirring at room temperature for 12h, finally adding 5mmol L-arginine, stirring at room temperature for 12h, the product was purified by dialysis in deionized water for 2 days to remove unreacted monomers and catalysts EDC and N...

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Abstract

The invention discloses a water-soluble degradable live cell fluorescent imaging material of a non-conjugated structure as well as a preparation method and application thereof. The method comprises the steps that citric acid, 1,8-octanediol and polyethylene glycol are subjected to thermal polymerization so as to obtain a PCG prepolymer; and then certain amino acids or silane derivatives are grafted to the PCG prepolymer for synthesis so as to obtain a polymer. The preparation method has the advantages of being simple and environmentally friendly, the synthetic raw materials are low in cost andnon-toxic, the prepared polymer has good blood compatibility and cytocompatibility, meanwhile, the material also shows good fluorescence characteristics and optical stability, and therefore the method has a good application prospect in live cell imaging.

Description

technical field [0001] The invention belongs to the technical field of degradable biomedical materials, and in particular relates to a preparation method and application of a water-soluble non-conjugated degradable living cell fluorescence imaging material. Background technique [0002] In recent years, with the application of various new technologies and methods, life science has developed rapidly. For example, through the use of fluorescence microscopy, people can understand the fine structure of cells, the interaction between cells, cell signal transduction, and the role of macromolecular proteins. However, the autofluorescence of cells in the visible light region conceals the signal from fluorescent materials and the photobleaching of fluorescent organic dye molecules is easy to occur. These two problems hinder the development and research of fluorescent imaging technology and fluorescent probes. Therefore, as science and technology With the continuous development, some...

Claims

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Application Information

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IPC IPC(8): C08G69/44C08G77/445C08G77/26C08G77/14C08G63/668C09K11/06G01N21/64G01N33/533G01N33/569
CPCG01N21/6428G01N21/6456G01N33/533G01N33/56966C09K11/06C08G63/668C08G69/44C08G77/14C08G77/26C08G77/445C09K2211/14G01N2021/6439
Inventor 雷波王敏郭旖
Owner XI AN JIAOTONG UNIV
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