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A kind of covalent organic polymer and its preparation method and application

A covalent organic and polymer technology, applied in the field of medicine, can solve the problems of unreported and rare cancer combination therapy, and achieve the effects of good reconstitution ability, good distribution, good water solubility and biocompatibility

Active Publication Date: 2018-11-02
SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the use of COP materials as carrier-free nano-drug delivery systems is still rare.
However, the use of covalent organic polymers as drug delivery vehicles in the combined treatment of cancer with photodynamic therapy and chemotherapy has never been reported.

Method used

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  • A kind of covalent organic polymer and its preparation method and application
  • A kind of covalent organic polymer and its preparation method and application
  • A kind of covalent organic polymer and its preparation method and application

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preparation example Construction

[0033] The present invention also provides a method for preparing a covalent organic polymer, comprising: mixing and reacting amino-terminated polyethylene glycol, a compound of formula (I) and a secondary amine to obtain a covalent organic polymer;

[0034]

[0035] According to the present invention, the present invention mixes amino-terminated polyethylene glycol, a compound of formula (I) and a secondary amine to obtain a covalent organic polymer; wherein, the amino-terminated polyethylene glycol is a monoamino-terminated Polyethylene glycol, namely The molecular weight of the amino-terminated polyethylene glycol is preferably 1KDa~10KDa, more preferably 3KDa~8KDa; the secondary amine is preferably 4,4-propylpiperidinylpiperidine, N,N'-dimethyl Ethylenediamine, N,N'-dibenzylethylenediamine, N,N'-bis(2-hydroxyethyl)ethylenediamine or 1,3-bis((trimethylol)methylamino)propane The solvent of the reaction is preferably dimethyl sulfoxide; the molar ratio of the compound of...

Embodiment 1

[0042] The preparation of acid-sensitive covalent organic polymer a-THPP-PEG specifically includes the following steps:

[0043] Dissolve 135.6mg of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin and 245mg of triethylamine in dried tetrahydrofuran, then add 217.2mg of acryloyl chloride dropwise to the system, and then Stir the reaction under nitrogen atmosphere for 12 hours; filter and concentrate the solution, dissolve it in dichloromethane, extract three times with 0.1M aqueous sodium carbonate solution, three times with saturated aqueous sodium chloride solution, combine the organic phases and wash with anhydrous sodium sulfate After drying for 2 hours, filter, concentrate the filtrate dropwise into ice n-hexane and centrifuge, take the solid at the bottom and dry it in vacuum to obtain 5,10,15,20-tetrakis(4-hydroxyphenyl) porphyrin with the structure of formula (I) Phenyl derivatives.

[0044] Dissolve 26mg of 5,10,15,20-tetrakis(4-hydroxyphenyl)porphyrin derivatives and 3...

Embodiment 2

[0049] Example 2: Degradation performance test of a-THPP-PEG in buffer solutions with different pH values

[0050] Because a-THPP-PEG can cleave the cross-linking of β-amino ester group through acid, it can dissociate under weak acidic conditions in the tumor microenvironment. In order to study the degradation of a-THPP-PEG under weakly acidic conditions, we tested the release of porphyrin and the particle size change of nanoparticles in buffers with different pH values.

[0051] Figure 6 It is the cumulative release curve figure of described a-THPP-PEG in the buffer solution of different pH values, as can be seen from the figure, along with the prolongation of time, in the buffer solution of pH 6.0, porphyrin cumulative release rate far exceeds Cumulative release rate in buffer at pH 7.4;

[0052] Figure 7 It is a graph showing the change in particle size of the a-THPP-PEG in buffers of different pH values; as can be seen from the figure, as time goes on, in the buffer s...

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Abstract

The invention provides a covalent organic polymer and a preparation method and application thereof. The covalent organic polymer is obtained by making amine-terminated polyethylene glycol, a compound with the structure shown in the formula (I) and secondary amine be mixed and react. The compound can crack under the acid condition by crosslinking the compound with the structure shown in the formula (I), the secondary amine and the amine-terminated polyethylene glycol through beta-amino ester. The compound has very good water solubility and biocompatibility, and obtained nanoparticles can generate singlet oxygen under irradiation of lasers, are disassociated under the weakly-acidic condition on tumor sites to release pre-loaded anticancer medicine, and have certain application in photodynamics therapy and chemotherapy combined treatment of tumors. The covalent organic polymer a-THPP-PEG can be used as a functional medicine conveying system, and use of additional carriers in the medicine is avoided.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a covalent organic polymer and its preparation method and application. Background technique [0002] Cancer is one of the major diseases that endanger human health. With the development of science and technology, photodynamic therapy (PDT) is an emerging tumor treatment method. Compared with traditional chemotherapy, radiotherapy and surgical treatment, photodynamic therapy Dynamic therapy has the advantages of safer, fewer complications, and less damage to the organism, so it has received more and more attention. Photodynamic therapy excites the photosensitive molecules enriched in the tumor site by light of a specific wavelength to generate cytotoxic reactive oxygen species, which causes tumor damage and death by damaging the genetic structure of tumor cells, thereby achieving the purpose of treatment. [0003] Covalent organic polymer (covalent organic polymer, COP) is a new type of p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/333A61K41/00A61K47/34A61P35/00
CPCA61K41/0042A61K41/0071A61K47/34C08G65/333C08G65/33317C08G65/33396C08G2650/04
Inventor 刘庄王海蓉
Owner SUZHOU INNOVATIVE BIOMATERIALS & PHARM CO LTD
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