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Carboxybutyryl chitosan sulfuric ester and preparation method and use thereof

A technology of carboxybutyryl chitosan sulfate and chitosan sulfate, applied in the field of carboxybutyryl chitosan sulfate, can solve the problems of difficult sulfonation reaction, dissociation of carboxyl groups, etc. Control, less side reactions, mild reaction conditions

Inactive Publication Date: 2006-04-19
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the sulfation reaction is a heterogeneous reaction, groups such as carboxymethyl groups change the diffusion behavior of the sulfonation reagent in the polysaccharide molecular chain during the reaction, making the sulfonation reaction difficult to carry out; dissociation phenomenon

Method used

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  • Carboxybutyryl chitosan sulfuric ester and preparation method and use thereof
  • Carboxybutyryl chitosan sulfuric ester and preparation method and use thereof
  • Carboxybutyryl chitosan sulfuric ester and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 4.20g sulfur content is that the chitosan sulfate ester of 16.87% (weight ratio) is dissolved in the NaOH / glycine buffer solution (I=1mol / L) of 9.0 in 20ml pH, stirs at room temperature, divides and adds 0.6g butanediol in two times Acid anhydride (molar ratio of chitosan sulfate sugar unit to succinic anhydride 0.6) was stirred for 24 hours, and the pH was adjusted to 9.0-10.0; the reaction solution was put into a dialysis bag and dialyzed for 3 days, and concentrated to obtain 0.5 g of brown powder, which was N- Carboxybutyryl chitosan sulfate. The substitution degree of elemental analysis is 0.77mol / unit, gel chromatography proves that the difference between molecular weight and chitosan sulfate is very small, there is no degradation phenomenon in the reaction process, and the corresponding group characteristic absorption appears in infrared analysis, carboxyl (1560cm -1 and 1414cm -1 ) and amidocarbonyl (1640cm -1 ) without ester carbonyl absorption (1720cm -1 ),...

Embodiment 2

[0025] As in Example 1, the amount of succinic anhydride is 0.2g (the molar ratio of chitosan sulfate ester sugar unit to succinic anhydride is 0.2), and the elemental analysis degree of substitution is 0.18mol / unit. The activated partial thromboplastin time and thrombin time reached 1.1 times and 2 times of the corresponding chitosan sulfate respectively.

Embodiment 3

[0027] As in Example 1, the amount of succinic anhydride is 0.8g (the molar ratio of chitosan sulfate sugar unit to succinic anhydride is 0.8), and the elemental analysis degree of substitution is 0.77mol / unit. The activated partial thromboplastin time and thrombin time reached 0.5 times and 0.9 times of the corresponding chitosan sulfate respectively.

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Abstract

The present invention discloses carboxyl butyryl chitosan sulfate. It is prepared through dissolving chitosan sulfate with sulfur content of 3-20 wt% and molecular weight of 5000-20000 in distilled water to obtain 5-30 wt% concentration chitosan sulfate aqua in homogeneous phase condition; adding succinic anhydride, mixing and reaction through stirring at 20-30 deg.c; dialysis and freeze drying to obtain carboxyl butyryl chitosan sulfate. The present invention has the advantages of mild reaction condition, easily controlled carboxyl substituting degree, less side reaction, high selectivity, etc. The carboxyl butyryl chitosan sulfate of the present invention has very high anticoagulant activity and may be used in preparing blood coagulation resisting medicine.

Description

technical field [0001] The invention relates to carboxybutyryl chitosan sulfate and its preparation method and application. It belongs to the technical field of organic chemistry as well as to the field of biochemistry. Background technique [0002] Chitosan sulfate has obvious anticoagulant activity, and it is expected to replace heparin as a novel anticoagulant drug (J.Doczi, A.Fishman, amd j.A King, J.Am.chem.Soc., 75(1953 ), 1521-1513), and the introduction of carboxyl group can promote its anticoagulant activity. Literature reports when carboxyl group / sulfonic acid group is about 1: 1 carboxymethyl chitosan sulfate even strengthens (S.Nishimura, N.Nishi.S.Tokurn, Carbohydr. Res., 156 (1986): 286-292). At present, there are two ways to introduce carboxyl groups into chitosan sulfate: one is to react chitosan with chloroformic acid under alkaline conditions to generate carboxymethyl chitosan, and then generate carboxymethyl chitosan through sulfate esterification. Sul...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/08A61P7/02
Inventor 杜予民黄荣华杨建红
Owner WUHAN UNIV
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