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Oligomeric fucosylated glycosaminoglycan and preparation method thereof

A technology of glycosylated glycosylamine and polyfucus, which is applied in the field of medicine, can solve the problems of fucose substitution side chain shedding, high reaction temperature requirements, severe reaction conditions, etc., to reduce the difference between batches and shorten the reaction time course , the effect of improving the reaction speed

Active Publication Date: 2010-06-16
SHENZHEN NEPTUNUS PHARMA RES INST CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Non-selective cleavage of the main chain glycosidic bonds can form oligomeric FG products with different reducing ends, that is, there are higher levels of GlcUA and GalNAc ends at the same time, thus affecting the homogeneity of the product; and the cleavage of the side chain glycosidic bonds can lead to Detachment of fucose-substituted side chains
[0007] In addition, conventional H 2 o 2 The reaction conditions required for the depolymerization of FG by this method are relatively severe, the reaction temperature is high, and the reaction time is long, but the key defect is that the controllability and repeatability of the reaction are poor.

Method used

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  • Oligomeric fucosylated glycosaminoglycan and preparation method thereof
  • Oligomeric fucosylated glycosaminoglycan and preparation method thereof
  • Oligomeric fucosylated glycosaminoglycan and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] The peroxide depolymerization of the FG of embodiment 1 metal ion catalysis

[0047] 1.1 Materials:

[0048] FG: Fucosylated glycosaminoglycan derived from Apostichopus japonicus, extracted and prepared according to the literature method (J Biol Chem, 1991, 266(21): 13530-6). Purity 98% (HPGPC, area normalization method), molecular weight (Mw), 69800.

[0049] h 2 o 2 , CH 3 COONa·3H 2 O, NaCl, NaOH, CuCl 2 , FeCl 2 , ZnCl 2 Reagents used: All commercially available analytical reagents.

[0050] 1.2 Method:

[0051] Dissolve 5.0 g of each of the four parts of Apostichopus japonicus FG in 180 ml of water in a round bottom flask, keep warm in a water bath at 45 ° C and continue to stir evenly, add 10 ml of pure water or 20 mmol / L copper chloride (Cu 2+ ) solution, ferrous chloride (Fe 2+ ) solution or zinc chloride (Zn 2+ ) solution, within 2 hours, dropwise add 10% H at a rate of 15ml / h 2 o 2 During the reaction, 1N NaOH solution was used to control the p...

Embodiment 2

[0057] Embodiment 2 direct peroxide depolymerization method and metal ion catalyzed peroxide depolymerization method gained dFG product NMR spectrum detection

[0058] 2.1 Materials:

[0059] FG: Fucosylated glycosaminoglycan derived from Apostichopus japonicus, extracted and prepared according to the literature method (J Biol Chem, 1991, 266(21): 13530-6). Purity 98% (HPGPC, area normalization method), molecular weight (Mw), 69800.

[0060] h 2 o 2 , CH 3 COONa·3H 2 O, NaCl, NaOH, Cu(CH3COO) 2 ·H 2 Reagents used in O, etc.: All commercially available analytical reagents.

[0061] 2.2 Method:

[0062] Preparation of dFG: Dissolve 5.0g each of two parts of Apostichopus japonicus FG in 180ml of aqueous solution in a round bottom flask, keep warm in a water bath at 70°C and 35°C respectively and keep stirring evenly, then add 10ml of pure water or acetic acid at a concentration of 60mmol / L respectively Copper (Cu 2+ ) solution, and then drop 10% H at a rate of 10ml / h ...

Embodiment 3

[0082] Example 3 The direct peroxide depolymerization method and the dFG prepared by the metal ion catalyzed peroxide depolymerization method Repeatability and controllability comparison

[0083] 3.1 Materials:

[0084] Same as 2.1

[0085] 3.2 Method:

[0086] Depolymerization of FG by direct hydrogen peroxide method: Dissolve 300g of five parts of Apostichopus japonicus FG in 9L of water, keep warm in a water bath at 60°C and continue to stir evenly, then add 15% H2O at a rate of 0.6L / h within 2 hours 2 o 2 , During the reaction process, 1N NaOH solution was used to control the pH value range from 7.2 to 7.8. After continuously stirring and reacting for 6.5 hours under this condition, add 3.0 g of EDTA disodium salt to the reaction solution and mix well, cool with ice water, add 3 times the volume of 95% ethanol to precipitate the polysaccharide, centrifuge to obtain the precipitate, and use 0.6 L of 60% Washed twice with ethanol, then dissolved in 10L water and ultr...

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Abstract

The invention discloses a method for preparing oligomeric fucosylated glycosaminoglycan which is prepared by depolymerizing fucosylated glycosaminoglycan by a depolymerization method of peroxide catalyzed by a 4th period transition metal ion in an aqueous medium, and the preparation method has mild reaction condition, good reproducibility and stability, high pyrolysis selectivity and uniform and controllable product quality. The polysaccharide molecule number of the obtained oligomeric fucosylated glycosaminoglycan using GalNAc as a reducing end is not less than 80 percent, the weight average molecular weight is about 6, 000-20, 000Da, and the protein disulfide isomerase (PDI) is 1.0-2.0.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to an oligofucosylated glycosaminoglycan (dFG) and a preparation method thereof, as well as a pharmaceutical composition containing the oligofucosylated glycosaminoglycan. Background technique [0002] Fucosylated Glycosaminoglycan (Fucosylated Glycosaminoglycan, Fucose-branched Glycosamino-glycan or fucose-containing glycosaminoglycan, referred to as FG), or called Fucosylated chondroitin sulfate (Fucosylated chondroitin sulfate, FCS), refers to a class of Extracted from animal body wall or viscera, it has a glycosaminoglycan derivative similar to the main chain structure of chondroitin sulfate, but with fucose sulfate on the side chain (J Biol Chem, 1988, 263(34): 18176- 83 and J Biol Chem, 1991, 266(21):13530-6). [0003] Natural FG has anticoagulant activity (Fan Huizeng et al., Acta Pharmaceutica Sinica, 1980, 15: 267), which makes it a potential therapeutic effec...

Claims

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Application Information

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IPC IPC(8): C08B37/08A61K31/737A61P7/02
CPCC08B37/0063A61P7/02
Inventor 赵金华吴明一康晖曾伟珍梁慧李姿徐世民冯汉林于琳
Owner SHENZHEN NEPTUNUS PHARMA RES INST CO LTD
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