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Salicylic-g-chitosan oligosaccharide grafts and synthesizing process

A technology of chitosan oligosaccharide and salicylic acid, which is applied in the field of salicylic acid-g-chitosan oligosaccharide graft and its synthesis, can solve the problems of poor solubility, troublesome handling, limitation and the like, and achieves abundant administration means. , Easy post-processing, good water solubility

Inactive Publication Date: 2008-12-03
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Wu Xuefen et al proposed a chitosan-g-salicylic acid and its synthetic method [Synthetic Chemistry, 2005, Volume 13, No. 5, Page 461-463]. The method is based on polymer chitosan and salicylic acid Acid is a raw material, and reacts by stirring or grinding in solvent-free or appropriate amount of solvent at a certain temperature, so that the amino group on chitosan and the carboxyl group of salicylic acid are automatically adsorbed and dehydrated to obtain chitosan-g-salicylic acid, but The post-processing of the product of this method is troublesome
And, because this method adopts high molecular weight chitosan as raw material, so the prepared chitosan-g-salicylic acid also inevitably brings some defects of chitosan itself, such as poor solubility etc., in application is limited

Method used

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  • Salicylic-g-chitosan oligosaccharide grafts and synthesizing process
  • Salicylic-g-chitosan oligosaccharide grafts and synthesizing process
  • Salicylic-g-chitosan oligosaccharide grafts and synthesizing process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] (1) Preparation of chitosan oligosaccharide

[0027] Take commercially available chitosan (70% degree of deacetylation) with a molecular weight of 550kDa, stir for 2 hours at 55°C and pH5. : 100 (w / w) cellulase (produced by Shanghai Boao Biotechnology Co., Ltd.) was added to degrade chitosan. The degree of degradation of chitosan was controlled by viscosity method. The resulting chitosan degradation solution is filtered to remove impurities, and ultrafiltration is used for fractionation using ultrafiltration membranes with molecular weights of 10 kDa and 30 kDa. The ultrafiltrate with a molecular weight between 10kDa and 30kDa was freeze-dried to obtain chitosan oligosaccharide with a deacetylation degree of 70% and a molecular weight of 18.0kDa.

[0028] (2) Preparation of salicylic acid-g-chitooligosaccharide graft

[0029] Accurately weigh 0.2756g carbodiimide (EDC) and 0.0397g salicylic acid (Salicycleacid, SA) and place in 3ml absolute ethanol (A liquid), then a...

Embodiment 2-5

[0031] Salicylic acid-g-chitooligosaccharide grafts were prepared according to the synthetic recipe listed in Table 1, and other conditions were the same as in Example 1.

[0032] Table 1: Synthetic formulations of salicylic acid-chitooligosaccharide (SA-g-CSO) with different molecular weights and grafting ratios

[0033] Example

[0034] molecular weight

Embodiment 6

[0035] Embodiment 6: Determination of physicochemical properties of salicylic acid-g-chitooligosaccharide graft

[0036] The salicylic acid-g-chitooligosaccharide grafts prepared in Examples 1-5 were used as test objects.

[0037] A. The amino substitution degree of the obtained salicylic acid-g-chitooligosaccharide graft was determined by trinitrobenzenesulfonic acid method.

[0038]Take certain molecular weight chitosan oligosaccharides (0.5-9mg) of different weights, accurately weighed, dissolve in 2ml of distilled water respectively, add 2ml of 4% (w / v) sodium bicarbonate solution and 0.1% (w / v) of Trinitrobenzenesulfonic acid 2ml, incubated at 37°C for 2h. Add 2ml of 2N hydrochloric acid, shake well, drive away the air bubbles by ultrasonic, measure the absorbance value (A) at 344nm wavelength, and obtain the amino substitution standard curve of the molecular weight chitosan oligosaccharide. Weigh 4 mg of the salicylic acid graft of an appropriate amount of the molecula...

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Abstract

The invention discloses salicylic acid-g-chitosan oligosaccharide graft and the synthetic method thereof. The salicylic acid-g-chitosan oligosaccharide graft, the general structure of which is shown in formula (I), is prepared from alicylic acid and chitosan oligosaccharide by graft polymerization. The molecular weight of chitosan oligosaccharide is 1-100kDa and the deacetylation degree thereof is 70%-100%. A part of amino groups on chitosan oligosaccharide chain in the salicylic acid-g-chitosan oligosaccharide graft are replaced by salicyl, and the substitution degree of the amino group is 1%-80%. The synthetic method is simple and convenient for post-treatment. The prepared salicylic acid-g-chitosan oligosaccharide graft employs hydrotropic compound salicylic acid as the hydrophobic part and chitosan oligosaccharide as the hydrophilic part to form salicylic acid-g-chitosan oligosaccharide micelle as an insoluble drug carrier in an aqueous medium by self-aggregation, thereby the administering means is greatly enriched and the curative effect is improved.

Description

(1) Technical field [0001] The invention relates to a salicylic acid-g-chitooligosaccharide graft and a synthesis method thereof. (2) Background technology [0002] Amphiphilic polymer micelles, as insoluble drug carrier materials, are a new means for improving the solubility of insoluble drugs in recent years. Polymer micelles are core-shell structures spontaneously formed by amphiphilic groups in solvents. Compared with commonly used surfactants, polymer micelles have a lower critical micelle concentration and stable spatial structure, and can exhibit unique biological stability. Through the selection and modification of the hydrophilic and hydrophobic two-part groups, different properties can be endowed to the polymer micelles to meet the requirements of different drug structures and administration sites. Nano-sized polymer micelles also have "enhanced penetration and retention", which is of special significance for tumor targeting therapy. [0003] Chitosan, is a natu...

Claims

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Application Information

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IPC IPC(8): C08B37/08C12P19/16A61K47/36
Inventor 胡富强魏晓红袁弘杜永忠
Owner ZHEJIANG UNIV
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