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Oxidized graphene modified by hyaluronic acid and preparation method and application of medicinal composition of oxidized graphene modified by hyaluronic acid

A hyaluronic acid modification, hyaluronic acid technology, applied in the field of medicine, can solve the problems of single photothermal therapy, limited involvement, complex carrier structure, etc., to achieve tumor-specific targeting, excellent biocompatibility, high-efficiency light The effect of thermal therapeutic activity

Inactive Publication Date: 2013-04-10
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, such synthesis steps are relatively cumbersome, and the stability, compatibility and targeting requirements cannot be met at the same time with a single molecule, resulting in a complex carrier structure
In addition, at this stage, the research on graphene oxide is mostly focused on single photothermal therapy, or simply used as a carrier of chemotherapy drugs, and the involvement of "photothermal combined chemotherapy" is limited. Therefore, the improvement and innovation of anti-tumor drug carriers is an urgent need to be solved question

Method used

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  • Oxidized graphene modified by hyaluronic acid and preparation method and application of medicinal composition of oxidized graphene modified by hyaluronic acid
  • Oxidized graphene modified by hyaluronic acid and preparation method and application of medicinal composition of oxidized graphene modified by hyaluronic acid
  • Oxidized graphene modified by hyaluronic acid and preparation method and application of medicinal composition of oxidized graphene modified by hyaluronic acid

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Experimental program
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Embodiment 1

[0021] The preparation method of the graphene oxide modified by described hyaluronic acid comprises the following steps:

[0022] (1) Synthesis of ammoniated hyaluronic acid: 95 mg of hyaluronic acid, 254 mg of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and N-hydroxysuccinyl Dissolve 150 mg of amine in 8 ml of organic solvent, stir at room temperature for 30 min to obtain a reaction solution, slowly drop the reaction solution into 0.4 ml of ethylenediamine formamide solution, add dropwise in an ice bath for 1 h, rise to room temperature for 6 h, and react After the end, add 50ml of acetone to precipitate, filter with suction to obtain a precipitate, add water to redissolve the precipitate, dialyze for 2 days, and freeze-dry to obtain ammoniated hyaluronic acid; the organic solvent is formamide, N,N-dimethyl One of methyl formamide and dimethyl sulfoxide;

[0023] (2) Synthesis of hyaluronic acid-modified graphene oxide: Dissolve 13 mg of graphene oxide in ...

Embodiment 2

[0025] The preparation method of the graphene oxide modified by described hyaluronic acid comprises the following steps:

[0026] (1) Synthesis of ammoniated hyaluronic acid: 100 mg of hyaluronic acid, 259 mg of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 155 mg of N-hydroxysuccinimide, Dissolve in 10ml of organic solvent, stir at room temperature for 30 minutes to obtain a reaction solution, slowly drop the reaction solution into 0.5ml of ethylenediamine formamide solution, add dropwise in an ice bath for 1 hour, rise to room temperature and react for 3 hours, after the reaction, Add 50ml of acetone to precipitate, filter with suction to obtain a precipitate, add water to redissolve the precipitate, dialyze for 2 days, and freeze-dry to obtain ammoniated hyaluronic acid; the organic solvent is formamide, N,N-dimethylformamide , a kind of dimethyl sulfoxide;

[0027] (2) Synthesis of hyaluronic acid-modified graphene oxide: Dissolve 15 mg of graphene ...

Embodiment 3

[0029] The preparation method of the graphene oxide modified by described hyaluronic acid comprises the following steps:

[0030] (1) Synthesis of ammoniated hyaluronic acid: 105 mg of hyaluronic acid, 264 mg of 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 160 mg of N-hydroxysuccinimide, Dissolve in 12ml of organic solvent, stir at room temperature for 30 minutes to obtain a reaction solution, slowly drop the reaction solution into 0.6ml of ethylenediamine formamide solution, add dropwise in an ice bath for 1 hour, rise to room temperature and react for 48 hours, after the reaction, Add 50ml of acetone to precipitate, filter with suction to obtain a precipitate, add water to redissolve the precipitate, dialyze for 2 days, and freeze-dry to obtain ammoniated hyaluronic acid; the organic solvent is formamide, N,N-dimethylformamide , a kind of dimethyl sulfoxide;

[0031](2) Synthesis of hyaluronic acid-modified graphene oxide: Dissolve 17mg graphene oxide i...

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Abstract

The invention relates to oxidized graphene modified by hyaluronic acid and a preparation method and an application of a medicinal composition of the oxidized graphene modified by the hyaluronic acid and can effectively solve the problem of non-targeting property of conventional photothermal therapy and chemotherapy technology. For solving the problem, the invention adopts the technical scheme that the hyaluronic acid is in covalent linkage with oxidized graphene by alkylene diamine which is used as a link arm and a nano layer can be formed in a water medium; the hyaluronic acid is low molecular weight hyaluronic acid of which the molecular weight is equal to or less than 400 kD and is equal to or higher than 500 Daltons; and the link arm is alkylene diamine of which the carbon number is 2 to 12. The oxidized graphene modified by the hyaluronic acid has excellent biocompatibility, water solubility and stability and is an innovation on cancer treatment medicaments.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method and application of hyaluronic acid-modified graphene oxide and a pharmaceutical composition thereof. Background technique [0002] Malignant tumors have surpassed cardiovascular diseases and become the leading cause of death for urban residents, seriously threatening human life and health. At present, surgery, radiotherapy, and chemotherapy constitute the three major means of tumor treatment. However, surgery can only remove tumors that are visible to the naked eye, but it is difficult to remove invisible subclinical lesions; traditional chemotherapy often has the problems of poor targeting and dose-limiting toxicity. A new type of treatment. [0003] Graphene oxide is a derivative of graphene, which consists of two regions: an unoxidized aromatic region where carbon atoms are connected to each other by sp2 hybridization and an aliphatic six-membered ring where ca...

Claims

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Application Information

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IPC IPC(8): C01B31/04A61K47/36A61K47/04A61K41/00A61K45/00A61P35/00C01B32/198
Inventor 侯琳张振中胡志军张红岭冯倩华王亚婷
Owner ZHENGZHOU UNIV
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