Amphipathic chitosan-bile acid derivatives and preparation method thereof

A bile acid derivative, chitosan technology, applied in the field of biomedicine, can solve the problems of poor water solubility, no solubilization and emulsifying ability of chitosan, and achieve good surface activity, good biocompatibility, non-toxicity, good The effect of biocompatibility

Inactive Publication Date: 2013-04-24
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Aiming at the disadvantages of poor water solubility and no solubilizing and emulsifying ability of chitosan in the prior art, the invention provides a hydrophobically modified amphiphilic chitosan-bile acid derivative with good water solubility and a preparation method thereof

Method used

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  • Amphipathic chitosan-bile acid derivatives and preparation method thereof
  • Amphipathic chitosan-bile acid derivatives and preparation method thereof
  • Amphipathic chitosan-bile acid derivatives and preparation method thereof

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Embodiment 1

[0029] The amphiphilic chitosan-bile acid derivative general formula of the present embodiment is as described in the summary of the invention, wherein, R 2 , R 3 Both are -OH, R 4 for -CH 2 CHOHCH 3 .

[0030] The preparation method is as follows:

[0031] 1. Dissolve 1.0g of chitosan with 100ml of 1% acetic acid, then add 100ml of methanol solution containing 0.76g of cholic acid, stir well, add 0.072g of EDC and 0.086g of NHS and react at 25°C for 24h. The product was neutralized by adding 10ml of ammonia water, added with 200ml of methanol for precipitation, filtered, the filter cake was fully soaked in acetone for dehydration, then washed with acetone and then vacuum-dried to obtain cholic acid-chitosan.

[0032] 2. Disperse the cholic acid-chitosan prepared in step 1 in 10ml alkaline isopropanol solution for alkalization for 10h. The alkaline isopropanol solution is 35wt% NaOH and isopropanol in a volume ratio of 1:9 the mix of. Add 4.4ml of propylene oxide to the...

Embodiment 2

[0049] The amphiphilic chitosan-bile acid derivative general formula of the present embodiment is as described in the summary of the invention, wherein, R 2 for -H,R 3 for -OH, R 4 for -CH 2 CHOHCH 3 .

[0050] The preparation method is as follows:

[0051] 1. Dissolve 1.0g of chitosan with 100ml of 1% acetic acid, then add 100ml of methanol solution containing 0.73g of deoxycholic acid, stir well, add 0.072g of EDC and 0.086g of NHS and react at 25°C for 24h. The product was neutralized by adding 10 ml of ammonia water, added 200 ml of methanol to precipitate, filtered, the filter cake was fully soaked in acetone for dehydration, then washed with acetone and dried in vacuum to obtain deoxycholic acid-chitosan.

[0052] 2. Disperse the deoxycholic acid-chitosan prepared in step 1 in 10ml alkaline isopropanol solution for alkalization for 10h. The alkaline isopropanol solution is 35wt% NaOH and isopropanol in a volume ratio of 1:9 the mix of. Add 4.4ml of propylene oxide...

Embodiment 3

[0054] The amphiphilic chitosan-bile acid derivative general formula of the present embodiment is as described in the summary of the invention, wherein, R 2 , R 3 Both are -H, R 4 for -CH 2 CHOHCH 3 .

[0055] The preparation method is as follows:

[0056] 1. Dissolve 1.0g of chitosan with 100ml of 1% acetic acid, then add 100ml of methanol solution containing 0.70g of lithocholic acid, stir well, add 0.072g of EDC and 0.086g of NHS and react at 25°C for 24h. Add 10ml of ammonia water to the product, add 200ml of methanol to precipitate, filter, fully soak the filter cake in acetone for dehydration, then wash with acetone and vacuum dry to obtain lithocholic acid-chitosan.

[0057] 2, disperse the lithocholic acid-chitosan that step 1 makes in 10ml alkaline isopropanol solution and basify for 10h, the alkaline isopropanol solution is 35wt% NaOH and isopropanol in a volume ratio of 1:9 the mix of. Add 4.4ml of propylene oxide to the solution, reflux in a water bath at 45...

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Abstract

The invention relates to amphipathic chitosan-bile acid derivatives and a preparation method thereof. The amphipathic chitosan-bile acid derivatives have the structure shown as a general formula I; and in the formula, R1 refers to H or COCH3, R2 and R3 respectively refer to -H or -OH, and R4 refers to -CH2CHOHCH3. The preparation method comprises the following steps of: reacting chitosan with bile acid in the presence of activating reagents of EDC and NHS to obtain hydrophobic chitosan-bile acid; and reacting the hydrophobic chitosan-bile acid with epoxypropane under the alkaline condition toobtain the chitosan-bile acid derivatives with good water solubility. By the method, the amphipathic chitosan-bile acid derivatives with high surface activity, emulsifying property and hydrotropy canbe obtained, and can serve as medicine solubilizing and sustained-release carriers.

Description

technical field [0001] The invention relates to an amphiphilic chitosan-bile acid derivative and a preparation method thereof, belonging to the technical field of biomedicine. Background technique [0002] The application of many drugs used for treatment is greatly limited due to their poor solubility. Improving the solubility and bioavailability of drugs is an urgent problem to be solved in medicine. Amphiphilic polymers can undergo microphase separation in aqueous media to form supramolecular aggregates with a hydrophobic inner core and a hydrophilic outer shell. The disadvantages of unsatisfactory drug solubilization and high toxicity, its hydrophobic core can also protect the drug from degradation and control the slow release of the drug, while the hydrophilic shell helps micelles to circulate in the blood for a long time, Therefore, it is a research hotspot in the drug delivery system in recent years. [0003] Most of the polymer micelles used as drug solubilizing ca...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08
Inventor 隋卫平宋朋李国宝
Owner UNIV OF JINAN
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