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Acyclovir-chitosan-stearic acid grafting, synthetic method and application thereof

A technology of stearic acid and chitosan, which is applied in the application field of preparing anti-hepatitis B virus drugs, can solve the problems of limited drug loading capacity and difficult loading, and achieve the effects of increasing drug concentration, increasing intake, and reducing toxic and side effects

Inactive Publication Date: 2010-08-04
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, graft micelles also have some potential limitations, such as limited drug loading capacity, difficulty in encapsulating hydrophilic drugs, etc.

Method used

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  • Acyclovir-chitosan-stearic acid grafting, synthetic method and application thereof
  • Acyclovir-chitosan-stearic acid grafting, synthetic method and application thereof
  • Acyclovir-chitosan-stearic acid grafting, synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Embodiment 1: the synthesis of acyclovir-chitosan-stearic acid graft

[0021] (1) Synthesis of acyclovir-succinic acid intermediate: 562.5mg (2.5mmol) acyclovir, 500.0mg (5.0mmol) succinic anhydride and 0.355mL triethylamine were dissolved in 37.5mL dry N , N-dimethylformamide, 60 ℃ water bath reaction 21h. After the reaction solution was cooled, most of the volatile components were evaporated under reduced pressure, 25 mL of ice water was added, and 2N hydrochloric acid was added to adjust the pH to 2. The white precipitate was collected by filtration, washed thoroughly with ice water, and dried at 40°C. Put the white precipitate into a round-bottomed flask, add a small amount of methanol, stir in a water bath at 70°C, reflux with a condenser, slowly add methanol dropwise until the solids are completely dissolved, let stand overnight at room temperature, filter with suction to obtain white crystals, and dry at 40°C to obtain Acyclovir-succinic acid intermediate.

[...

Embodiment 2

[0026] Embodiment 2: the synthesis of acyclovir-chitosan-stearic acid graft

[0027] (1) Synthesis of acyclovir-succinic acid intermediate: 562.5mg (2.5mmol) acyclovir, 500.0mg (5.0mmol) succinic anhydride and 0.355mL triethylamine were dissolved in 37.5mL dry N , N-dimethylformamide, 60 ℃ water bath reaction 21h. After the reaction solution was cooled, most of the volatile components were evaporated under reduced pressure, 25 mL of ice water was added, and 2N hydrochloric acid was added to adjust the pH to 2. The white precipitate was collected by filtration, washed thoroughly with ice water, and dried at 40°C. Put the white precipitate into a round-bottomed flask, add a small amount of methanol, stir in a water bath at 70°C, reflux with a condenser, slowly add methanol dropwise until the solids are completely dissolved, leave it at room temperature overnight, filter with suction to obtain white crystals, and dry at 40°C to obtain Acyclovir-succinic acid intermediate.

[0...

Embodiment 3

[0036] Embodiment 3: the synthesis of acyclovir-chitosan-stearic acid graft

[0037] (1) Synthesis of acyclovir-succinic acid intermediate: 562.5mg (2.5mmol) acyclovir, 500.0mg (5.0mmol) succinic anhydride and 0.355mL triethylamine were dissolved in 37.5mL dry N , N-dimethylformamide, 60 ℃ water bath reaction 21h. After the reaction solution was cooled, most of the volatile components were evaporated under reduced pressure, 25 mL of ice water was added, and 2N hydrochloric acid was added to adjust the pH to 2. The white precipitate was collected by filtration, washed thoroughly with ice water, and dried at 40°C. Put the white precipitate into a round-bottomed flask, add a small amount of methanol, stir in a water bath at 70°C, reflux with a condenser, slowly add methanol dropwise until the solids are completely dissolved, let stand overnight at room temperature, filter with suction to obtain white crystals, and dry at 40°C to obtain Acyclovir-succinic acid intermediate.

[...

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Abstract

The invention provides a hydrophilic antiviral drug, namely acyclovir-chitosan-stearic acid grafting, which is beneficial to the load of the drug by a target carrier material through chemical grafting by the synthesis of an acyclovir-succinic acid midbody. On the basis, by adopting the load of the antiviral drug in cells of a molecular target mark for a chitosan-stearic acid grafting micelle with high-efficiency cellular uptake and low toxicity, the drug uptake of virus cells is greatly increased, and the drug concentration of the drug molecular target mar position is increased. The acyclovir-chitosan-stearic acid grafting increases the drug uptake of virus cells, is beneficial to reducing the distribution of the drug in normal tissues or cells and reduces the toxic side effect of the drug; and the drug concentration increase of the drug molecular target mark position is beneficial to increasing the healing effect of the antiviral drug. The acyclovir-chitosan-stearic acid grafting has the chemical general formula (disclosed in the specification).

Description

technical field [0001] The invention relates to an antiviral acyclovir prodrug and its synthesis method and application, specifically acyclovir-chitosan-stearic acid graft and its synthesis method, acyclovir-chitosan -Application of stearic acid graft in preparation of anti-hepatitis B virus medicine. Background technique [0002] As an infectious disease, viral diseases have become one of the main threats to human health. Chronic hepatitis B is a serious viral infectious disease and the main cause of liver fibrosis, liver cirrhosis and liver cancer. More than 500,000 people die from primary liver cancer every year in the world, and as many as 80% of the primary liver cancers are caused by chronic hepatitis B. Since the existing antiviral drugs cannot completely inhibit and clear the virus, there are problems of large dosage, low curative effect, toxic side effects and easy drug resistance. Therefore, for the treatment of viral diseases, especially the treatment of chronic...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61K31/522C08B37/08A61P1/16A61P31/20A61K47/61
Inventor 胡富强杜永忠袁弘
Owner ZHEJIANG UNIV
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