Gadolinium-series contrast agent with carboxylated short single-walled carbon nanotube modified by hyaluronic acid as carrier as well as preparation method and application of gadolinium-series contrast agent

A single-walled carbon nanotube and hyaluronic acid modification technology, which is applied in the field of medicine, can solve the problems of low relaxation efficiency, large toxic and side effects, and short half-life, and achieve high relaxation rate, low toxicity, and high targeting Effect

Inactive Publication Date: 2013-12-18
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] In view of the above situation, to overcome the defects of the prior art, the purpose of the present invention is to provide a preparation method of gadolinium contrast agent with carboxylated short single-walled carbon nanotubes modified by hyaluronic acid as the carrier, which can effectively solve the problem of traditional magnetic resonance imaging. Poor drug targeting, short half-life, low relaxation efficiency, large toxic and side effects, etc.

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  • Gadolinium-series contrast agent with carboxylated short single-walled carbon nanotube modified by hyaluronic acid as carrier as well as preparation method and application of gadolinium-series contrast agent

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Embodiment 1

[0017] The preparation method of the present invention can be realized by the following steps in concrete implementation:

[0018] (1) Synthesis of carboxylated short single-walled carbon nanotubes: Put 80 mg of short single-walled carbon nanotubes into 40 mL of mixed acid, react for 3 hours under ultrasonic conditions with a power of 180 W, vacuum filter to obtain a solid product, and wash repeatedly with ultrapure water The product is neutralized to obtain short single-walled carbon nanotube carboxylation products;

[0019] (2) Synthesis of aminated hyaluronic acid: 95 mg hyaluronic acid, 254 mg 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC) and 150 mg N-hydroxysuccinyl Imine (NHS), dissolved in 8mL formamide, stirred at room temperature for 30min to obtain a reaction solution, within 1h under ice-bath conditions, the reaction solution was dropped into 0.4mL ethylenediamine formamide solution, raised to room temperature and reacted for 6h , after the react...

Embodiment 2

[0023] The preparation method of the present invention can be realized by the following steps in concrete implementation:

[0024] (1) Synthesis of carboxylated short single-walled carbon nanotubes: Put 90 mg of short single-walled carbon nanotubes into 45 mL of mixed acid, react for 3.5 hours under ultrasonic conditions with a power of 190 W, vacuum filter to obtain a solid product, and repeat with ultrapure water Wash the product to neutrality to obtain short single-walled carbon nanotube carboxylation products;

[0025] (2) Synthesis of aminated hyaluronic acid: Dissolve 100mg of hyaluronic acid, 259mg of EDC and 155mg of NHS in 10mL of N,N-dimethylformamide, stir at room temperature for 30min to obtain a reaction solution, and keep in ice bath for 1h Inside, drop the reaction liquid into 0.5mL ethylenediamine formamide solution, rise to room temperature and react for 24h. After the reaction, add 50ml of acetone, vacuum filter to get precipitate, add ultrapure water to redi...

Embodiment 3

[0029] The preparation method of the present invention can be realized by the following steps in concrete implementation:

[0030] (1) Synthesis of carboxylated short single-walled carbon nanotubes: Put 100 mg of short single-walled carbon nanotubes into 50 mL of mixed acid, react for 4 hours under ultrasonic conditions with a power of 200 W, vacuum filter to obtain solid products, and repeat with ultrapure water Wash the product to neutrality to obtain the carboxylation product of short single-walled carbon nanotubes;

[0031] (2) Synthesis of aminated hyaluronic acid: Dissolve 105mg of hyaluronic acid, 264mg of EDC and 160mg of NHS in 12ml of dimethyl sulfoxide, and stir at room temperature for 30min to obtain a reaction solution. The reaction solution was dropped into 0.6ml of ethylenediamine formamide solution, raised to room temperature and reacted for 48 hours. After the reaction, 50ml of acetone was added, and the precipitate was obtained by vacuum filtration. The preci...

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Abstract

The invention relates to the field of pharmacy and particularly relates to a gadolinium-series contrast agent with a carboxylated short single-walled carbon nanotube modified by hyaluronic acid as a carrier as well as a preparation method and an application of the gadolinium-series contrast agent, which can effectively solve the problem that an existing contrast agent is poor in technical targeting property, short in half-life peroid, low in relaxation efficacy and large in toxic and side effects. According to the technical scheme, the preparation method comprises the following steps: covalently connecting hyaluronic acid containing natural polysaccharide molecules with a carboxylated short single-walled carbon nanotube through taking alkylene diamine as a connecting arm, then adhering gadolinium trichloride onto the modified carbon nanotube in a physical method, and forming a nanosuspension with water, thus obtaining the gadolinium-series contrast agent with the carboxylated short single-walled carbon nanotube modified by hyaluronic acid as the carrier. The gadolinium-series contrast agent with the carboxylated short single-walled carbon nanotube modified by hyaluronic acid as the carrier has good chemical stability and good biocompatibility, can be effectively used as a magnetic resonance contrast agent in tumor diagnosis and is an innovation on a tumor contrast agent.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a preparation method of a gadolinium-based contrast agent with carboxylated short single-walled carbon nanotubes modified by hyaluronic acid as a carrier. Background technique [0002] Malignant tumors are a group of frequently occurring diseases that seriously endanger human health. According to the statistics of the World Health Organization, malignant tumors have surpassed cardiovascular diseases to become the leading cause of human death. In recent years, although the treatment methods have been improved and the survival rate has been improved, the mortality rate is still high. Therefore, more effective and safe means are needed to realize the early diagnosis and treatment of tumors. Since Lauterbur first realized magnetic resonance imaging technology in 1973, it has rapidly developed into an indispensable reference for assisting clinical diagnosis due to its strong soft tissue resolu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K49/12A61K49/18
Inventor 侯琳张振中王丽丽王亚婷张慧娟张红岭
Owner ZHENGZHOU UNIV
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