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Sulfhydrylated chitosan and preparation method thereof

A technology of thiolated chitosan and hydroxybutyl chitosan, which is applied in the field of medical materials and can solve problems such as poor antioxidant capacity and insufficient tissue adhesion

Pending Publication Date: 2021-12-21
HANGZHOU SINGCLEAN MEDICAL PROD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] However, as a polymer with temperature-sensitive gel-forming properties, hydroxybutyl chitosan is limited by insufficient tissue adhesion and poor antioxidant capacity in practical applications.

Method used

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  • Sulfhydrylated chitosan and preparation method thereof
  • Sulfhydrylated chitosan and preparation method thereof
  • Sulfhydrylated chitosan and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1, prepare hydroxybutyl chitosan HBC

[0023] (1) Weigh 20g chitosan, dissolve in 1000ml 1% HCl aqueous solution, filter, add dropwise 1mol / L NaOH solution to the filtrate to obtain a precipitate, wash with distilled water until neutral, desalinate with 70% ethanol, 95% Dehydrated with ethanol and dried at 50°C to obtain a purified chitosan sample.

[0024] (2) Take 3 g of purified chitosan and disperse it in 30 ml of 50% NaOH aqueous solution, stir for 24 hours, filter, and squeeze out excess lye to obtain a solid. Gained solid is added to 60ml isopropanol aqueous solution (V 异丙醇 :V 水 =10:10), stir evenly, heat up to 60°C, add 80ml of 1,2-epoxybutane dropwise, and react for 24h. After cooling to room temperature, 10% HCl aqueous solution was added dropwise to the reaction liquid to adjust the pH of the system to neutral. Filter out the insoluble matter, add 3 times the volume of ethanol to precipitate, centrifuge, and dry the precipitate to obtain hydrox...

Embodiment 2

[0026] Embodiment 2, the preparation of thiolated chitosan HBC-SH

[0027] Accurately weigh 0.5g of HBC prepared in Example 1, dissolve in 100mL of 0.05% aqueous acetic acid, add 5mmol of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDC .HCl and N-hydroxysuccinimide NHS, stirred at room temperature in the dark for 0.5h; then added 5mmol L-cysteine ​​hydrochloride Cys.HCl, stirred at room temperature in the dark for 0.5h; adjusted the reaction liquid with 1M sodium hydroxide pH to 5, react at room temperature in the dark for 24 hours; after the reaction, dialyze with purified water in the dark for 3 days; freeze-dry the obtained dialysate to obtain thiolated chitosan HBC-SH-1.

Embodiment 3

[0028] Embodiment 3, the preparation of thiolated chitosan HBC-SH

[0029] Accurately weigh 0.5g of HBC prepared in Example 1, dissolve in 100mL of 0.05% aqueous acetic acid, add 5mmol of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride EDC .HCl and N-hydroxysuccinimide NHS, stirred at room temperature in the dark for 0.5h; then added 10mmol L-cysteine ​​hydrochloride Cys.HCl, stirred at room temperature in the dark for 0.5h; adjusted the reaction liquid with 1M sodium hydroxide pH to 5, react at room temperature in the dark for 24 hours; after the reaction, dialyze with purified water in the dark for 3 days; freeze-dry the obtained dialysate to obtain thiolated chitosan HBC-SH-2.

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Abstract

The invention discloses sulfhydrylated chitosan and a preparation method thereof. The sulfhydrylated chitosan is chitosan jointly modified by hydroxybutyl and sulfydryl. The preparation method comprises the following steps: firstly, introducing hydroxybutyl on a chitosan molecular chain; secondly, in the sulfydryl part, free amino of hydroxybutyl chitosan and carboxyl of L-cysteine are subjected to condensation reaction to introduce sulfydryl; an aqueous solution of the sulfhydrylated chitosan is in a solution state at low temperature and can be subjected to flow injection, and when the temperature is raised to about 37 DEG C, hydrogel can be formed. Due to the introduction of sulfydryl, the oxidation resistance and tissue adhesion ability of the material are improved. The sulfhydrylated chitosan prepared by the method possibly has wide application prospects in the aspects of tissue engineering, drug delivery systems, cell culture, cosmetics and the like.

Description

technical field [0001] The invention belongs to the technical field of medical materials, and relates to a mercaptolylated chitosan and a preparation method thereof. Background technique [0002] Chitosan is the only alkaline polysaccharide among natural polysaccharides, widely used in food additives, textiles, agriculture, environmental protection, beauty care, cosmetics, antibacterial agents, medical fibers, medical dressings, artificial tissue materials, drug slow-release materials, gene transfer Conductors, biomedical fields, medical absorbable materials, tissue engineering carrier materials, medical and drug development and other daily chemical industries. Hydroxybutyl chitosan is a chitosan derivative with water solubility and temperature responsiveness. The aqueous solution of hydroxybutyl chitosan has temperature sensitivity, and it is in a solution state at low temperature, and forms a gel when the temperature rises. [0003] However, hydroxybutyl chitosan, as a p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 伍飞飞陈忠毅蒋婉君李杰马矢徒胡梦君
Owner HANGZHOU SINGCLEAN MEDICAL PROD