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Preparation method and application of curcumin chitosan-stearic acid graft micelle

A technology of chitosan and stearic acid, which is applied in the field of synthesis of polymer prodrugs, can solve the problems of curcumin's low water solubility, low absorption in the body, and low bioavailability

Inactive Publication Date: 2012-10-24
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] The object of the invention is to provide a kind of preparation method of curcumin chitosan-stearic acid graft micelle and its application

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  • Preparation method and application of curcumin chitosan-stearic acid graft micelle
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  • Preparation method and application of curcumin chitosan-stearic acid graft micelle

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preparation example Construction

[0019] The steps of the preparation method of curcumin chitosan stearic acid graft micelles are as follows:

[0020] (1) Synthesis of low molecular weight chitosan

[0021]Get the chitosan 60g that commercially available molecular weight is 450kDa deacetylation degree is 90%, join in the hydrochloric acid aqueous solution of 1.2% in 2000mL concentration by weight, stir 2 hours under the condition of 55 ℃, then add chitosanase 4g, in Perform enzymatic hydrolysis reaction at 55°C, filter with a Buchner funnel, stir at 80°C for half an hour, add 0.5 g of activated carbon, dilute, filter, treat the filtrate with a 0.45 μm microporous membrane, spray dry to obtain chitosan, and measure The weight-average molecular weight that obtains chitosan is 18kDa;

[0022] (2) Synthesis of chitosan-stearic acid graft

[0023] Take 0.8g of chitosan, add 40mL of distilled water and stir to dissolve, add 0.65g of carbodiimide, stir to dissolve, dissolve 0.1g of stearic acid in 20mL of etha...

Embodiment 1

[0029] (1) Synthesis of low molecular weight chitosan (CSO)

[0030] Get the chitosan 60g that commercially available molecular weight is 450kDa deacetylation degree is 90%, join in the hydrochloric acid aqueous solution of 1.2% in 2000mL concentration by weight, stir 2 hours under the condition of 55 ℃, then add chitosanase 4g, in Perform enzymolysis reaction at 55°C, filter with Buchner funnel, stir at 80°C for half an hour, add 0.5g of activated carbon, dilute, filter, treat the filtrate with a 0.45μm microporous membrane, spray dry to obtain chitosan, measure The weight-average molecular weight that obtains chitosan is 18kDa;

[0031] (2) Synthesis of chitosan-stearic acid graft (CSO-SA)

[0032] Take 0.8g of chitosan, add 40mL of distilled water and stir to dissolve, add 0.65g of carbodiimide, stir to dissolve, dissolve 0.1g of stearic acid in 20mL of ethanol solution, mix the above two solutions, and stir magnetically at 400rpm Under certain conditions, react ...

Embodiment 2

[0036] (1) Synthesis of low molecular weight chitosan

[0037] Get commercially available molecular weight is 450kDa deacetylation degree is 90% chitosan 60g, joins in the hydrochloric acid aqueous solution of 1.2% in 2000mL concentration by weight, stirs 2 hours under the condition of 55 ℃, then adds chitosanase 4g, in Perform enzymolysis reaction at 55°C, filter with a Buchner funnel, stir at 80°C for half an hour, add 0.5g of activated carbon, dilute, filter, process the filtrate with a 0.45μm microporous membrane, spray dry to obtain chitosan, and measure The weight-average molecular weight that obtains chitosan is 18kDa;

[0038] (2) Synthesis of chitosan-stearic acid graft

[0039] Take 0.8g of chitosan, add 40mL of distilled water and stir to dissolve, add 0.65g of carbodiimide, stir to dissolve, dissolve 0.1g of stearic acid in 20 mL of ethanol solution, mix the above two solutions, and magnetically Under stirring conditions, react at a constant temperature ...

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Abstract

The invention discloses a preparation method and application of a curcumin chitosan-stearic acid graft micelle. According to the invention, curcumin is used as a bulk drug, and a graft formed by chitosan oligosaccharide and stearic acid is used as a drug carrier; the preparation method comprises a first step of carrying out covalent binding on chitosan oligosaccharide and stearic acid under the action of the cross-linking agent of carbodiimide so as to form a chitosan oligosaccharide-stearic acid graft (CSO-SA) carrier and a second step of adding a certain amount of a curcumin DMSO solution into a solution of the CSO-SA carrier and carrying out complexation to form a CSO-SA / curcumin drug-loaded nanometer micelle. The micelle prepared in the invention has an average particle size of 114.7 nm and a Zeta potential of 18.5 mV. In-vivo and in- In-vivo tests show that CSO-SA / curcumin has strong cellular internalization capacity, can improve accumulation of curcumin in tumor cells and has a strong killing effect on MCF-7, MCF-7 / Adr and colorectal cancer cells. In-vivo administration enables selective inhibition of growth of tumor cells to be realized while no obvious toxic effect is exerted on mice.

Description

technical field [0001] The invention relates to the field of synthesis of polymer prodrugs, in particular to a preparation method and application of curcumin chitosan stearic acid graft micelles. Background technique [0002] Curcumin (Curcumin, Cur, 1,7-bis(4-hydroxy-5-methoxyphenyl))-1,6-heptadiene-3,5-dione), molecular formula C 21 h 20 o 6 , molecular weight 368.37, the main chain is unsaturated aliphatic and aromatic groups, easily soluble in methanol, ethanol, acetone, ethyl acetate and lye, insoluble in water, slightly soluble in benzene and ether, at high temperature or It has poor stability in strong acid and strong alkali environment. It is a highly photosensitive substance that needs to be stored away from light. It is mainly extracted and separated from the roots or stems of plants such as Curcuma longa, Curcuma longa, Curcuma longa, etc., especially in Asia. It has a long history of medicinal use in India and China, and is used as a natural phenolic food addi...

Claims

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Application Information

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IPC IPC(8): A61K9/10A61K47/36A61K31/12A61P35/00
Inventor 黄建王科胡富强吴先国
Owner ZHEJIANG UNIV
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