Preparation method and application of covalent organic framework material containing acylhydrazone bonds and disulfide bonds

A covalent organic framework and acylhydrazone bond technology, applied in the field of covalent organic framework polymer porous materials, can solve the problems that COFs cannot respond to acidic and reducing microenvironments at the same time, restricting the application of COFs, etc., achieve high load capacity, easy Control, operation simple effect

Active Publication Date: 2019-08-30
TIANJIN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, some literatures have reported the preparation of COFs with different composition structures and their application in drug delivery, etc., but most of the exist...

Method used

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  • Preparation method and application of covalent organic framework material containing acylhydrazone bonds and disulfide bonds
  • Preparation method and application of covalent organic framework material containing acylhydrazone bonds and disulfide bonds
  • Preparation method and application of covalent organic framework material containing acylhydrazone bonds and disulfide bonds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1: Preparation of Covalent Organic Frameworks (COFs) Containing Acylhydrazone Bonds and Disulfide Bonds

[0028] Trimylene tricarbaldehyde (3.24mg, 0.20mmol) was placed in the reaction tube, followed by adding 5mL of mesitylene and dioxane (the volume ratio of mesitylene and dioxane was 3:1) in the reaction tube After the solution was mixed and fully dissolved, 4,4'-dithiodibenzohydrazide (100.2 mg, 0.3 mmol) was added to the tube. After fully dissolving, the catalyst aqueous acetic acid solution (0.6 mL, 5 mol / L) was added dropwise to the above solution. The sample was repeatedly cold-cut with liquid nitrogen-vacuum-thawed, then sealed under an anaerobic high vacuum, and placed in an oil bath at 120°C for 72 hours. After the reaction was completed, when the temperature of the system dropped to room temperature, precipitation appeared, and the solid product was separated by centrifugation, and washed repeatedly with tetrahydrofuran to remove unreacted monomers ...

Embodiment 2

[0034] Example 2: Preparation of covalent organic frameworks (COFs) containing acylhydrazone bonds and disulfide bonds

[0035] Trimylene tricarbaldehyde (3.24mg, 0.20mmol) was placed in the reaction tube, and 10mL of mesitylene and dioxane (the volume ratio of mesitylene and dioxane was 1:1) was added to the reaction tube After the solution was mixed and fully dissolved, 4,4'-dithiodibenzohydrazide (100.2 mg, 0.3 mmol) was added to the tube. After fully dissolving, the catalyst aqueous acetic acid solution (5 mL, 1 mol / L) was added dropwise to the above solution. The sample was repeatedly cold-cut with liquid nitrogen-vacuum-thawed, then sealed under anaerobic high vacuum, and placed in an oil bath at 150°C for 24 hours. After the reaction was completed, when the temperature of the system dropped to room temperature, precipitation appeared, and the solid product was separated by centrifugation, and washed repeatedly with tetrahydrofuran to remove unreacted monomers and solve...

Embodiment 3

[0036] Example 3: Preparation of Covalent Organic Frameworks (COFs) Containing Acylhydrazone Bonds and Disulfide Bonds

[0037] Trimylene tricarbaldehyde (3.24mg, 0.20mmol) was placed in the reaction tube, and 10mL of mesitylene and dioxane (the volume ratio of mesitylene and dioxane was 5:1) was added to the reaction tube After the solution was mixed and fully dissolved, 4,4'-dithiodibenzohydrazide (100.2 mg, 0.3 mmol) was added to the tube. After fully dissolving, the catalyst aqueous acetic acid solution (3 mL, 10 mol / L) was added dropwise to the above solution. The sample was repeatedly cold-cut with liquid nitrogen-vacuum-thawed, then sealed under an anaerobic high vacuum, and placed in an oil bath at 100°C for 48 hours. After the reaction was completed, when the temperature of the system dropped to room temperature, precipitation appeared, and the solid product was separated by centrifugation, and washed repeatedly with tetrahydrofuran to remove unreacted monomers and s...

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Abstract

The invention discloses a preparation method and application of a covalent organic framework material containing acylhydrazone bonds and disulfide bonds. The preparation method comprises the followingsteps: using 4, 4'-dithiodibenzoylhydrazide and 1, 3, 5-benzenetricarboxaldehyde as building units, using a mixed solution of mesitylene and dioxane as a solvent, and using acetic acid as a catalystto react at 100-150 DEG C for 24-72 h through a solvothermal method to obtain the covalent organic framework material, wherein the reaction is as shown in the following formula. The material has a porous structure with a covalent organic framework, a specific surface area (BET) of 300-350 m<2>/g, and relatively high drug loading capacity for antitumor hydrophobic drugs such as doxorubicin or paclitaxel; the prepared covalent organic framework material and a polymer surfactant can form a stable nanostructure through ultrasonic co-assembly; and the material can decompose and release loaded drugsin acidic and reductive microenvironments, and has relatively high application prospects in antitumor drug delivery and other aspects.

Description

technical field [0001] The invention belongs to the field of covalent organic framework (COFs) polymer porous materials. The invention relates to a preparation method and application of a covalent organic framework material containing an acylhydrazone bond and a disulfide bond, which is sensitive to acidic and reducing microenvironments. Background technique [0002] Environmentally sensitive materials refer to a class of intelligent materials that are perceptible and responsive to the environment. They can respond to various types of stimulus signals from the external environment (temperature, acid-base environment, redox environment, ion etc.) produce reversible or irreversible changes in physical properties and (or) chemical structures. This unique function can be used to prepare smart materials with adjustable functions, and has been widely used in many fields, such as controlled drug release, gene transfer, bioseparation, and protein purification. In particular, the p...

Claims

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Application Information

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IPC IPC(8): C08G12/10A61K47/34A61P35/00
CPCC08G12/10A61K47/34A61P35/00
Inventor 张建华郭睿威邓联东董岸杰
Owner TIANJIN UNIV
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