Porphyrin-based temperature-responsive self-healing hydrogel, preparation method, use method and application thereof

A temperature-responsive, self-healing technology, applied in the field of medical polymer materials and functional polymer materials, to achieve the effect of simple preparation method, good injectability, and good mechanical properties

Active Publication Date: 2020-10-30
SHANGHAI TENTH PEOPLES HOSPITAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

There are no reports or patent applications for self-healing hydrogels prepared by combining porphyrin with thermosensitivity

Method used

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  • Porphyrin-based temperature-responsive self-healing hydrogel, preparation method, use method and application thereof
  • Porphyrin-based temperature-responsive self-healing hydrogel, preparation method, use method and application thereof
  • Porphyrin-based temperature-responsive self-healing hydrogel, preparation method, use method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Dissolve 0.1 g of 5,10,15,20-tetra-p-hydroxyphenylporphyrin (THPP) in dichloromethane; add 0.27 g of 2-bromoisobutyryl bromide and 0.12 g of triethylamine, and react at 0°C for 48 hours , remove residual 2-bromoisobutyryl bromide, triethylamine and dichloromethane to obtain THPP(-Br) 4 Initiator (Product 1).

[0042] Dissolve 0.08 g of product 1 in N,N-dimethylformamide, add 4.22 g of 2-methyl-2-acrylic acid-2-(2-methoxyethoxy)ethyl ester, 0.59 g of oligo(ethyl) Diol) methyl ether methacrylate, 0.16 g of hydroxyethyl methacrylate; under the action of the catalyst cuprous bromide / pentamethyldiethylenetriamine, the system reacts under the protection of inert gas such as argon or nitrogen, The reaction temperature was 60° C., and the reaction time was 6 hours. After removing the catalyst, it was precipitated in petroleum ether, filtered and dried to constant weight to obtain THPP(-MEO 2 MA-co-OEGMA-co-HEMA) 4 (Product 2).

[0043] Add 0.11 gram of p-aldehyde benzoic ac...

Embodiment 2

[0046] Dissolve 0.1 g of 5,10,15,20-tetra-p-hydroxyphenylporphyrin (THPP) in chloroform; add 0.42 g of 2-bromoisobutyryl bromide and 0.21 g of triethylamine, and react at 3°C ​​for 36 hours , remove residual 2-bromoisobutyryl bromide, triethylamine and chloroform to obtain THPP(-Br) 4 Initiator (Product 1).

[0047] Dissolve 0.08 g of product 1 in toluene, add 4.22 g of 2-methyl-2-acrylic acid-2-(2-methoxyethoxy)ethyl ester, 1.18 g of oligo(ethylene glycol) methyl ether methyl ester Acrylate, 0.30 g hydroxyethyl methacrylate; under the action of catalyst cuprous bromide / pentamethyldiethylenetriamine, the system reacts under the protection of inert gas such as argon or nitrogen, the reaction temperature is 80 °C, and the reaction time For 10 hours, after removing the catalyst, it was precipitated in n-hexane, filtered and dried to constant weight to obtain THPP(-MEO 2 MA-co-OEGMA-co-HEMA) 4 (Product 2).

[0048] 0.22 g of p-aldehyde benzoic acid was added to 1 g of product ...

Embodiment 3

[0050] Dissolve 0.1 g of 5,10,15,20-tetra-p-hydroxyphenylporphyrin (THPP) in tetrahydrofuran; add 0.40 g of 2-bromoisobutyryl bromide and 0.12 g of pyridine, and react at 5°C for 40 hours to remove residual 2 -bromoisobutyryl bromide and pyridine and tetrahydrofuran to give THPP(-Br) 4 Initiator (Product 1).

[0051] Dissolve 0.08 g of product 1 in N,N-dimethylformamide, add 4.22 g of 2-methyl-2-acrylic acid-2-(2-methoxyethoxy)ethyl ester, 1.0 g of oligo(ethoxy) diol) methyl ether methacrylate, 0.28 g of hydroxyethyl methacrylate; under the action of the catalyst cuprous chloride / pentamethyl diethylene triamine, the system reacts under the protection of inert gas such as argon or nitrogen, The reaction temperature was 80°C, and the reaction time was 12 hours. After removing the catalyst, it was precipitated in diethyl ether, filtered and dried to constant weight to obtain THPP(-MEO 2 MA-co-OEGMA-co-HEMA) 4 (Product 2).

[0052] Add 0.11 gram of p-aldehyde benzoic acid to 1...

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PUM

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Abstract

The invention relates to a porphyrin-based temperature-responsive self-healing hydrogel, a preparation method, a use method and application thereof. The preparation method comprises the following steps of: forming a Schiff base bond with a dynamic covalent bond characteristic between an aldehyde group contained in a star copolymer THPP (-MEO2MA-co-OEGMA-co-HEMA-CHO)4 and an amino group contained in branched polyethyleneimine (PEI), thereby obtaining the self-healing hydrogel. The porphyrin-based temperature-responsive self-healing hydrogel prepared by the preparation method disclosed by the invention has the advantages of injectability, photodynamic therapy, fluorescence imaging functionality, temperature responsiveness, specific recognition and enrichment of tumors and the like, and can be used as a wound dressing, a tumor drug carrier material, a stem cell carrier material, a gene vector material, fluorescence imaging, a photodynamic therapy product and the like. The structural formula of the self-healing hydrogel is shown as formula (i), wherein m is 90, n is 5-15, x is 5-10, and y is 24.

Description

technical field [0001] The invention relates to the technical field of medical polymer materials and functional polymer materials, in particular to a temperature-responsive self-healing hydrogel based on porphyrin and its preparation, use and application. Background technique [0002] Hydrogels also have the advantages of good self-healing properties, mechanical properties, adhesion properties, and biocompatibility, and are widely used in many fields, especially in the field of biomedicine. However, common hydrogels often cannot balance self-healing properties and mechanical properties, which affects their practical applications. Self-healing hydrogels are injectable and self-healing, and their self-healing properties through dynamic covalent bonds are particularly valuable. Based on the dynamic coupling reaction between tyrosine hydrochloride catalyzed by enzymes, Wang Jianxin et al. used a catalyst to induce a coupling reaction between tyrosine hydrochloride derivatives, ...

Claims

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Application Information

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IPC IPC(8): C08G81/02C08G73/04C08F220/28C08F220/20C08J3/075C08L87/00
CPCC08G81/024C08G73/02C08F220/282C08J3/075C08J2387/00C08F2438/01C08F220/286C08F220/20
Inventor 李茂全谢晓云袁伟忠康黎
Owner SHANGHAI TENTH PEOPLES HOSPITAL
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