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Preparation method and application of graphene oxide derivative

A technology of graphene and derivatives, which is applied in the field of medicine, can solve the problem of non-targeting of chemotherapy technology, and achieve the effect of excellent biocompatibility

Inactive Publication Date: 2014-01-01
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of the above situation, in order to solve the defects of the prior art, the purpose of the present invention is to provide a method for the preparation and application of graphene oxide derivatives, which can effectively solve the non-targeting problems of traditional photothermia and chemotherapy techniques

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  • Preparation method and application of graphene oxide derivative

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Embodiment 1

[0025] The preparation method of the graphene oxide derivative is characterized in that the azo aromatic compound is covalently connected to the graphene oxide with an azo aromatic bond, comprising the following steps:

[0026] (1) Synthesis of 4-bromobutyryl chloride: Dissolve 100 mg of 4-bromobutyric acid in 15 ml of organic solvent toluene or tetrahydrofuran, add 87 μl of thionyl chloride and 1 drop of N,N-dimethylformamide, and stir at room temperature for 3 h , and then rotary evaporated under reduced pressure at 45°C, and cooled to obtain 4-bromobutyryl chloride;

[0027] (2) Synthesis of amidated azoaromatic compounds: take 65 mg of 4,4′-bis(N-methacryloyl-6-aminocaproylamide) azobenzene, 3,3′,5,5′-tetrabromo- 4,4,4,4′-Quadruple (methacrylamide) azobenzene or 4-(methacryloyl) azobenzene was dissolved in 50ml of dichloromethane, added 87μl of triethylamine, stirred at room temperature for 2h Finally, under ice-bath conditions, slowly add 77 μl of 4-bromobutyryl chloride...

Embodiment 2

[0032] The preparation method of the graphene oxide derivative is characterized in that the polysaccharide compound is covalently connected to the graphene oxide with a glycosidic bond, comprising the following steps:

[0033] (1) Synthesis of 4-bromobutyryl chloride: Dissolve 10-20mg of 4-bromobutyric acid in 10-20ml of organic solvent, add 41-91μl of thionyl chloride and 1-3 drops of pyridine, at room temperature 15-30℃ Stir for 2-5h, rotate under reduced pressure at 40-50°C, and cool to obtain 4-bromobutyryl chloride; the organic solvent is one of dichloromethane, chloroform, toluene, and tetrahydrofuran;

[0034] (2) Synthesis of amidated polysaccharide compound: take 50-70 mg of polysaccharide compound, add 30-50 ml of the mixed solution, drop 4-8 μl of 4-bromobutyryl chloride obtained in step (1) under ice bath conditions, 60- Heating and reflux at 80°C for 5-8h, the reaction is completed, the reaction solution is cooled and added to methanol, suction filtered, washed wi...

Embodiment 3

[0039] The preparation method of the graphene oxide derivative is characterized in that the polysaccharide compound is covalently connected to the graphene oxide with a glycosidic bond, comprising the following steps:

[0040] (1) Synthesis of 4-bromobutyryl chloride: Dissolve 10 mg of 4-bromobutyric acid in 10 ml of organic solvent, dichloromethane or chloroform, add 41 μl of thionyl chloride and 1 drop of pyridine, stir at room temperature for 2 h, spin at 45 °C under reduced pressure Steam and cool to get 4-bromobutyryl chloride;

[0041] (2) Synthesis of amidated polysaccharide compound: Take 50-55 mg of chitosan or konjac glucomannan, add 30 ml of the mixed solution, drop 4 μl of 4-bromobutyryl chloride obtained in step (1) under ice bath conditions, 60 Heating at reflux for 8 hours at ℃, the reaction is completed, the reaction solution is cooled and added to methanol, suction filtered, washed with methanol, and dried in vacuum to obtain the initial product, which is furt...

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Abstract

The invention relates to a preparation and application method of a graphene oxide derivative, which can effectively solve the problem of non-targeting in the traditional photothermal therapy and chemotherapy technologies. The method comprises the following step: performing covalent connection on an azo aromatic compound and graphene oxide by taking an azo aromatic bond as a connecting arm, or performing covalent connection on a polysaccharide compound and the graphene oxide by taking a glycosidic bond as a connecting arm, wherein the weight ratio of the azo aromatic compound or polysaccharide compound to the graphene oxide is (5:1)-(17:4); the height of the graphene oxide is 0.8-1.2 nm, and the dimension is 0.1-50 mu m; and the azo aromatic compound is one of 4,4'-azodiphenylamine, 4,4'-dimethylacrylamide azobenzene, 4,4'-di(N-methylacryloyl-6-aminohexanamide)azobenzene, 3,3',5,5'-tetrabromo-4,4,4,4'-tetra(methacrylamide)azobenzene and 4-(methylacryloyl)azobenzene. The graphene oxide derivative has fine biocompatibility water solubility and stability, can realize specific tumor targeting and is an innovation of medicaments for tumor therapy.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method and application of graphene oxide derivatives. Background technique [0002] Colon cancer is one of the most common malignant tumors of the digestive tract. The morbidity and mortality of colon cancer in both western developed countries and developing countries are on the rise. Therefore, timely detection and symptomatic treatment are of great significance. At present, surgical treatment, radiation therapy and chemical drug therapy together constitute the three major means of colon cancer treatment, and chemical drug therapy occupies an important position in the three means. The flora-triggered drug delivery system is a kind of oral colon-targeted drug delivery system. It is based on the unique flora distribution of the human colon and utilizes various specific enzymes such as azoreductase and glycosidase possessed by bacteria to be able to biologically Degrade the d...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08C08B37/02C08B37/00C08B37/06C07C245/08C08B33/04A61K47/36A61K47/18A61K9/06A61P35/00
Inventor 侯琳张振中蒋桂香冯倩华张红岭
Owner ZHENGZHOU UNIV
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