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Hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier as well as preparation method and application thereof

A technology of hyaluronic acid and polyethylene glycol, which is applied in the direction of pharmaceutical formulations, medical preparations with non-active ingredients, medical preparations containing active ingredients, etc., can solve the problems of normal cell damage and limit the clinical application of chemotherapy drugs, etc. Achieve the effect of increasing long cycle time, easy operation and uniform particle size

Active Publication Date: 2014-03-05
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, in addition to killing tumor cells, chemotherapy drugs also damage normal cells to a certain extent, which greatly limits the clinical application of chemotherapy drugs.

Method used

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  • Hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier as well as preparation method and application thereof
  • Hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier as well as preparation method and application thereof
  • Hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1 Synthesis of hyaluronic acid-hydroxypropyl-β-cyclodextrin (HA-HP-β-CD) (cyclodextrin substitution degree is 20%)

[0036] Hyaluronic acid (0.2g, -COOH, 0.62mM, M=7000) was dissolved in 50mL of anhydrous formamide, heated in a 40°C water bath with magnetic stirring to dissolve, and cooled to room temperature. EDC (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) (0.2 g) was added and magnetically stirred for 3 h. Then HP-β-CD (0.22g, -OH, 1.8mM) was dissolved in 5mL of anhydrous formamide, and slowly added dropwise to the HA mixture. The addition was completed within 10 minutes, and stirring was continued at room temperature for 24h. The reaction mixture was dialyzed in distilled water for 2 days, filtered, and freeze-dried to obtain a white powder.

[0037] Determination by NMR 1 HNMR hydrogen spectrum is determined the structure of embodiment 1 compound, and the solvent of selection is D 2 O, the result is as figure 1 . 5.3-5.2ppm is H in hyd...

Embodiment 2

[0038] Example 2 Synthesis of hyaluronic acid-hydroxypropyl-β-cyclodextrin (HA-HP-β-CD) (the degree of substitution of cyclodextrin is 40%)

[0039] Hyaluronic acid (0.2g, -COOH, 0.62mM, M=7000) was dissolved in 50mL of anhydrous formamide, heated in a 40°C water bath with magnetic stirring to dissolve, and cooled to room temperature. EDC (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) (0.2 g) was added and magnetically stirred for 3 h. Then HP-β-CD (0.4g, -OH, 3.5mM) was dissolved in 5mL of anhydrous formamide, and slowly added dropwise to the HA mixture. The addition was completed within 10 minutes, and stirring was continued at room temperature for 24h. The reaction mixture was dialyzed in distilled water for 2 days, filtered, and freeze-dried to obtain a white powder.

[0040] Determination by NMR 1 HNMR hydrogen spectrum is determined the structure of embodiment 1 compound, and the solvent of selection is D 2 O, 5.3-5.2ppm is H in hydroxypropyl cyclodextr...

Embodiment 3

[0041] Example 3 Synthesis of hyaluronic acid-hydroxypropyl-β-cyclodextrin (HA-HP-β-CD) (the degree of substitution of cyclodextrin is 50%)

[0042] Hyaluronic acid (0.2g, -COOH, 0.62mM, M=7000) was dissolved in 50mL of anhydrous formamide, heated in a 40°C water bath with magnetic stirring to dissolve, and cooled to room temperature. EDC (1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride) (0.2 g) was added and magnetically stirred for 3 h. Then HP-β-CD (1.5g, -OH, 6.6mM) was dissolved in 5mL of anhydrous formamide, and slowly added dropwise to the HA mixture. The addition was completed within 10 minutes, and stirring was continued at room temperature for 24h. The reaction mixture was dialyzed in distilled water for 2 days, filtered, and freeze-dried to obtain a white powder.

[0043] Determination by NMR 1 HNMR hydrogen spectrum is determined the structure of embodiment 1 compound, and the solvent of selection is D 2 O. 5.2-5.1ppm is H in hydroxypropyl cyclodext...

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Abstract

The invention belongs to a novel pharmaceutical preparation form and the novel technical field, specifically relates to a hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier as well as a preparation method and application thereof, and simultaneously provides a nano drug delivery system which is self-assembled by taking hyaluronic acid-cyclodextrin-adamantane polyethylene glycol as the carrier and utilizing clathration force of the cyclodextrin to cover hydrophobic guest molecules. The hyaluronic acid- cyclodextrin-adamantane polyethylene glycol carrier has the advantages that the nano drug administration system not only can passively transmit drugs to tumor tissues by virtue of an EPR (Ethylene-Propylene Rubber) effect, but also can improve an anti-tumor effect of the drugs by virtue of a tumor-targeting effect of the hyaluronic acid. PEG (Polyethylene Glycol) molecules on the surface can be effectively prevented from being absorbed by a reticuloendothelial system, and in-vivo circulating time can be prolonged.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical preparations, and relates to a hyaluronic acid-cyclodextrin-adamantane polyethylene glycol carrier and its preparation method and application, in particular to the application of this type of compound in a drug delivery system. Background technique [0002] Tumors are a serious threat to human health, and chemotherapy is currently the main means of treating cancer. However, in addition to killing tumor cells, chemotherapy drugs also damage normal cells to a certain extent, which greatly limits the clinical application of chemotherapy drugs. Therefore, the development of new nano drug delivery system for anti-tumor drugs has attracted more and more attention. For example, paclitaxel albumin nanoparticles and doxorubicin liposomes have been successfully used in clinical practice. The outstanding advantage of nano-preparation lies in its nano-scale particle size, which can use the EPR effect ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K47/48A61P35/00A61P29/00C08G81/00C08B37/08C08B37/14C08G65/48A61K31/704
Inventor 孙进何仲贵韩晓鹏张天虹
Owner SHENYANG PHARMA UNIVERSITY
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