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Quaternary grating material and preparation method and application thereof

A technology of structural unit, chitosan oligosaccharide, applied in the field of compound and its synthesis, can solve the problems of insufficient lipophilicity, insufficient drug-carrying capacity, affecting cell transport function, etc.

Inactive Publication Date: 2010-07-14
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the lack of lipophilicity in its molecular chain affects its cell transport function as a drug carrier
The inventor's previous experimental research found that after stearic acid was grafted on the chitooligosaccharide, the obtained chitooligosaccharide stearic acid graft could self-aggregate in an aqueous medium to form micelles, which had the loading function of hydrophobic drugs and the rapid growth of tumor cells. The function of ingestion (Chinese invention patent ZL200710069117.5); Chitooligosaccharide stearic acid graft has the function of long circulation in the body after polyethylene glycol modification (Chinese invention patent application number: 200810062568.0); Both fatty acid grafts and PEG-modified chitooligosaccharide stearic acid grafts have the problem of insufficient drug-loading capacity, especially for antitumor drugs such as paclitaxel and camptothecin.

Method used

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  • Quaternary grating material and preparation method and application thereof
  • Quaternary grating material and preparation method and application thereof
  • Quaternary grating material and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Add 6 g of chitosan (average molecular weight 450,000) into 200 mL of 1.25 (v / v) hydrochloric acid aqueous solution, stir and dissolve at 55-60 ° C, and adjust the pH to 5.0 with dilute ammonia water or dilute hydrochloric acid. Cellulase was added at a ratio of cellulase to chitosan of 0.5:100 (w / w). After controlling the reaction time for 24 hours, the reaction product was -1 Centrifuge for 10 minutes. The supernatant was pretreated with a 0.45 μm microporous membrane, fractionated with ultrafiltration membranes of different molecular weights, and the ultrafiltrate was freeze-dried to obtain chitosan oligosaccharides with a certain molecular weight. By gel permeation chromatography, the average molecular weight of chitosan oligosaccharide was determined to be 1000Da.

[0023]Take by weighing 1.0g of chitosan oligosaccharide obtained above, add 160mL double-distilled water and stir to dissolve; in addition, weigh end carboxylated poly(lactic acid-glycolic acid) (mole...

Embodiment 2

[0027] Add 6 g of chitosan (average molecular weight 450,000) into 200 mL of 1.25 (v / v) hydrochloric acid aqueous solution, stir and dissolve at 55-60 ° C, and adjust the pH to 5.0 with dilute ammonia water or dilute hydrochloric acid. Cellulase was added at a ratio of cellulase to chitosan of 0.5:100 (w / w). After controlling the reaction time for 18 hours, the reaction product was -1 Centrifuge for 10 minutes. The supernatant was pretreated with a 0.45 μm microporous membrane, fractionated with ultrafiltration membranes of different molecular weights, and the ultrafiltrate was freeze-dried to obtain chitosan oligosaccharides with a certain molecular weight. By gel permeation chromatography, the average molecular weight of chitosan oligosaccharide was determined to be 5000Da.

[0028] Take by weighing 1.0g of chitosan oligosaccharide obtained above, add 160mL double-distilled water and stir to dissolve; in addition, take carboxylated poly(lactic acid-glycolic acid) (molecula...

Embodiment 3

[0032] Add 6 g of chitosan (average molecular weight 450,000) into 200 mL of 1.25 (v / v) hydrochloric acid aqueous solution, stir and dissolve at 55-60 ° C, and adjust the pH to 5.0 with dilute ammonia water or dilute hydrochloric acid. Cellulase was added at a ratio of cellulase to chitosan of 0.5:100 (w / w). After controlling the reaction time for 18 hours, the reaction product was -1 Centrifuge for 10 minutes. The supernatant was pretreated with a 0.45 μm microporous membrane, fractionated with ultrafiltration membranes of different molecular weights, and the ultrafiltrate was freeze-dried to obtain chitosan oligosaccharides with a certain molecular weight. By gel permeation chromatography, the average molecular weight of chitosan oligosaccharide was determined to be 5000Da.

[0033] Take by weighing 1.0g of chitosan oligosaccharide obtained above, add 160mL double-distilled water and stir to dissolve; in addition, take carboxylated poly(lactic acid-glycolic acid) (molecula...

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Abstract

The invention provides a polyethylene glycol-chitooligosaccharide-fatty acid-poly (lactic acid-glycolic acid) quaternary grafting material. Certain free amino radicals on the chains of the chitooligosaccharide are substituted by fatty acid, polyethylene glycol and poly (lactic acid-glycolic acid). The preparation method comprises synthesis of a chitooligosaccharide-fatty acid-poly (lactic acid-glycolic acid) ternary grating material through formation of an amido link by carboxyl-amino reaction of amino on the chitooligosaccharide, carboxyl-terminated poly (lactic acid-glycolic acid) and carboxy on the fatty acid, and reaction of the chitooligosaccharide-fatty acid-poly (lactic acid-glycolic acid) ternary grating material and formyl-terminated polyethylene glycol, thereby obtaining solid powder of the quaternary grafting material. The quaternary grafting material provided by the invention has the property of forming micelles self-aggregation in the aqueous medium, and the critical micelle concentration of the polyethylene glycol modified chitooligosaccharide-fatty acid grating material is 10-100mug / ml, which is significantly lower than the critical micelle concentration of general surfactants, thereby significantly improving the drug loading capacity. Moreover, the quaternary grafting material has the capability of taking in tumor cells, and can be used as a carrier material for application in preparation of anti-tumor drugs so as to realize the safe and effective drug treatment.

Description

technical field [0001] The present invention belongs to compound and its synthesis method, relates to polyethylene glycol-chitooligosaccharide-fatty acid-poly(lactic acid-glycolic acid) graft and its synthesis method, and polyethylene glycol-chitooligosaccharide-fatty acid-poly( Application of lactic acid-glycolic acid) graft in the preparation of antitumor drugs. Background technique [0002] Tumor has always been a major disease that directly threatens human health. Due to the lack of molecular targeting of the drug itself, tumor chemotherapy has major treatment problems such as low cure rate and huge toxic side effects. Directly targeting drugs to diseased tissues (organs) and cells through appropriate carrier technology is one of the important means to solve the low cure rate and toxic side effects of cancer chemotherapy. At present, scientists at home and abroad have made some progress in the tissue (organ) and cell targeting of tumor drugs through carrier technology, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G81/00C08G63/91C08G65/48A61K47/36A61P35/00
Inventor 杜永忠胡富强袁弘
Owner ZHEJIANG UNIV
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