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Folic acid-chitosan-Cy7 polymer with tumor targeting ability and preparation method of polymer

A technology of tumor targeting and chitosan derivatives, which is applied in the field of biomedicine and can solve problems such as poor solubility of chitosan

Inactive Publication Date: 2017-09-15
FUZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the poor solubility of chitosan, it needs to be chemically modified

Method used

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  • Folic acid-chitosan-Cy7 polymer with tumor targeting ability and preparation method of polymer
  • Folic acid-chitosan-Cy7 polymer with tumor targeting ability and preparation method of polymer
  • Folic acid-chitosan-Cy7 polymer with tumor targeting ability and preparation method of polymer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Synthesis of Polymer CF7:

[0044] Step a: Weigh 800 mg of chitosan and dissolve in 60 mL of anhydrous DMF, then add 1.6 g of phthalic anhydride, under nitrogen protection, stir and heat in an oil bath at 120°C. When the reaction solution became clear, the reaction was terminated. The reaction solution was poured into an appropriate amount of ice water, and a white precipitate was precipitated. After suction filtration, the solid was washed three times with ether and acetone respectively to remove excess phthalic anhydride, and dried to obtain product 2.

[0045] Step b: Weigh 100 mg of product 2, add 10 mL of N-methylpyrrolidone (NMP), heat and stir to dissolve. When the solution was cooled and placed in ice water, 616 mg N-bromosuccinimide (NBS) and 902 mg triphenylphosphine (TPP) were added. React at 80°C for two hours under nitrogen protection. After the reaction was over, the mixture was poured into 100 mL of ethanol, and a solid was precipitated. The product ...

Embodiment 2

[0049] Synthesis of Chitosan-Cy7 Polymer (C7):

[0050] Weigh 10 mg of the product 4 of Example 1, dissolve it in 5 mL of dimethyl sulfoxide, and add 10 mg of ALK-Cy7. The flask was sealed with a rubber stopper and protected with nitrogen after evacuation. First add 2.5 mg copper sulfate pentahydrate (dissolved in 100 μL secondary water) dropwise to the flask with a 1 mL syringe, and then add 2 mg sodium ascorbate (dissolved in 100 μL secondary water) dropwise. The reactants were reacted at 50 °C for 72 h in the dark. After the reaction, the reaction solution was dialyzed for 72 hours with a 14000 dialysis bag. After dialysis, the product was lyophilized. According to infrared spectrogram analysis, the 6-position azido group in product 4 reacted with the alkynyl group in ALK-Cy7 to form a triazole ring. Such as figure 1 As shown, chitosan-Cy7 polymer (C7) at 2100 cm -1 There is no infrared absorption peak, indicating that the azido group has successfully reacted with th...

Embodiment 3

[0052] Synthesis of chitosan-FA polymer (CF):

[0053] Weigh 10 mg of the product 4 of Example 1, dissolve it in 5 mL dimethyl sulfoxide, and add 10 mg ALK-FA. The flask was sealed with a rubber stopper and protected with nitrogen after evacuation. First add 2.5 mg copper sulfate pentahydrate (dissolved in 100 μL secondary water) dropwise to the flask with a 1 mL syringe, and then add 2 mg sodium ascorbate (dissolved in 100 μL secondary water) dropwise. The reactants were reacted at 50 °C for 72 h in the dark. After the reaction, the reaction solution was dialyzed for 72 hours with a 14000 dialysis bag. After dialysis, the product was lyophilized. According to infrared spectrogram analysis, the azido group at position 6 in product 4 reacted with the alkynyl group in ALK-FA to form a triazole ring. Such as figure 1 As shown, chitosan-FA polymer (CF) at 2100 cm -1 There is no infrared absorption peak, indicating that the azido group has successfully reacted with the alkyn...

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Abstract

The invention discloses a novel folic acid-chitosan-Cy7 polymer (CF7) serving as a diagnosis and treatment agent and a preparation method of the polymer. 6-nitrine-6-deoxidation-N-phthaloyl-chitosan, alkynyl modified folic acid (ALK-FA) and alkynyl modified heptamethine cyanine Cy7 (ALK-Cy7) react to synthesize a derivative. The polymer CF7 can be self-assembled to form a nano-particle and can be used as the nano diagnosis and treatment agent for tumors, folic acid molecules coupled on a framework can recognize high-expression tumor cells of folic acid receptors in a targeting manner, and Cy7 molecules can be used for near-infrared fluorescent imaging and photodynamic therapy.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and relates to a folic acid-chitosan-Cy7 polymer (CF7) and its preparation method and application, as well as nanoparticles formed by the polymer, its preparation method and application. Background technique [0002] Cancer is one of the main causes of threats to human health today. Traditional drug chemotherapy can cause damage to normal cells and tissues, which has become the biggest difficulty in tumor treatment. Due to the significant difference in pathological and physiological characteristics between tumor tissue and normal tissue, the permeability of blood vessels in tumor sites is enhanced, and macromolecular drugs and nanocarriers can easily penetrate vascular endothelial cells into tumor tissue. Long-term, high-concentration accumulation at the tumor site, this effect is called the enhanced penetration and retention (EPR) effect (Ghaz-Jahanian, M. A.; Abbaspour-Aghdam, F.; Anarjan,...

Claims

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Application Information

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IPC IPC(8): A61K49/00A61K41/00A61K47/69A61K47/54A61P35/00
CPCA61K41/0057A61K49/0032A61K49/0052A61K49/0093
Inventor 陈海军张英英高瑜
Owner FUZHOU UNIV
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