阅读说明：本技术 一种羧甲基壳聚糖衍生物及其制备方法 (Carboxymethyl chitosan derivative and preparation method thereof ) 是由 李征征 候冰娜 于 2019-09-24 设计创作，主要内容包括：一种己酰化羧甲基壳聚糖衍生物及其制备方法。该羧甲基壳聚糖为含己酰基的羧甲基壳聚糖衍生物,由羧甲基壳聚糖和正己酸酐通过己酰化反应制得,反应物正己酸酐与羧甲基壳聚糖氨基葡萄糖单元的摩尔比为1∶1～1∶5。本发明方法反应条件较温和,操作简单安全,更易于被研究人员接受。反应所得的己酰化羧甲基壳聚糖是一种天然的高分子材料,具有良好的水溶性且安全无毒,可以作为药物递送的载体。此外,本材料具有良好的温敏性和生物相容性,在药物合成、吸附材料、药物载体材料、抗菌材料等众多领域都有广泛的应用前景。(A hexanoyl carboxymethyl chitosan derivative and its preparation method are provided. The carboxymethyl chitosan is a hexanoyl-containing carboxymethyl chitosan derivative and is prepared by hexanoylation reaction of carboxymethyl chitosan and n-hexyl anhydride, and the molar ratio of the reactant n-hexyl anhydride to the carboxymethyl chitosan glucosamine unit is 1: 1-1: 5. The method has mild reaction conditions, simple and safe operation and easy acceptance by researchers. The hexanoyl carboxymethyl chitosan obtained by the reaction is a natural high molecular material, has good water solubility, is safe and nontoxic, and can be used as a carrier for drug delivery. In addition, the material has good temperature sensitivity and biocompatibility, and has wide application prospects in a plurality of fields such as drug synthesis, adsorption materials, drug carrier materials, antibacterial materials and the like.)

1. A hexanoyl carboxymethyl chitosan derivative and its preparation method are provided. The carboxymethyl chitosan is a hexanoyl-containing carboxymethyl chitosan derivative and is prepared by hexanoylation reaction of carboxymethyl chitosan and n-hexyl anhydride, and the molar ratio of the reactant n-hexyl anhydride to the carboxymethyl chitosan glucosamine unit is 1: 1-1: 5.

2. The method for preparing the acylated carboxymethyl chitosan derivative according to claim 1, wherein the method comprises the following steps:

dispersing carboxymethyl chitosan powder in 25 ml of deionized water, wherein the concentration is 0.5-5%, placing the mixture on a magnetic stirrer at room temperature and stirring the mixture until the carboxymethyl chitosan powder is completely dissolved, then adding 25 ml of anhydrous methanol, stirring the mixture at room temperature for 15-30 minutes, taking a certain amount of n-hexyl anhydride by using a liquid-transferring gun and adding the n-hexyl anhydride into the mixed solution, wherein the mass ratio of carboxymethyl chitosan to the n-hexyl anhydride is 1: 0.5-1: 5, reacting the mixture at room temperature for 24-48 hours, then pouring the mixture into a dialysis bag and dialyzing the mixture with the deionized water for 48 hours, and drying the mixture in a vacuum drying box until the weight is constant to obtain the water-soluble caproylated carboxymethyl chitosan derivative.

Technical Field

The invention relates to a hexanoyl carboxymethyl chitosan derivative and a preparation method thereof, in particular to a temperature-sensitive carboxymethyl chitosan derivative based on n-hexanoic anhydride and carboxymethyl chitosan as raw materials and a preparation method thereof.

Background

The carboxymethyl chitosan is a chitosan derivative prepared by performing carboxymethylation reaction on chitosan, compared with chitosan, the water solubility of the carboxymethyl chitosan is greatly improved, and the biocompatibility of the chitosan is kept. According to the different positions of carboxymethyl, carboxymethyl chitosan can be classified into O-carboxymethyl chitosan, N-carboxymethyl chitosan and N, O-carboxymethyl chitosan. Carboxymethyl chitosan has good biocompatibility and very low cytotoxicity and blood toxicity, and can be degraded in vivo, so that the carboxymethyl chitosan is widely used as a tissue repair material, a drug sustained-release material and the like. After the carboxymethyl chitosan is hexanoated and modified, a hydrophobic group is introduced into carboxymethyl chitosan molecules to prepare an amphiphilic polymer, the aqueous solution of the amphiphilic polymer has temperature sensitivity, and sol-gel conversion can occur to prepare temperature-sensitive hydrogel, so that the carboxymethyl chitosan has wider application in the field of biomedicine, and the hexanoation modification of the carboxymethyl chitosan is provided.

Disclosure of Invention

The invention aims to solve the problem that carboxymethyl chitosan does not have temperature sensitivity, and provides a carboxymethyl chitosan derivative with temperature sensitivity and a preparation method thereof.

The technical scheme of the invention is as follows:

a hexanoyl carboxymethyl chitosan derivative and its preparation method are provided. The carboxymethyl chitosan is a hexanoyl-containing carboxymethyl chitosan derivative and is prepared by hexanoylation reaction of carboxymethyl chitosan and n-hexyl anhydride, and the molar ratio of the reactant n-hexyl anhydride to the carboxymethyl chitosan glucosamine unit is 1: 1-1: 5.

A preparation method of a caproylated carboxymethyl chitosan derivative comprises the following specific steps:

dispersing carboxymethyl chitosan powder in 25 ml of deionized water, placing the mixture on a magnetic stirrer at room temperature, stirring the mixture until the carboxymethyl chitosan powder is completely dissolved, then adding 25 ml of anhydrous methanol, stirring the mixture for 15 to 30 minutes at room temperature, using a liquid-transferring gun to take a certain amount of n-hexyl anhydride to add the n-hexyl anhydride into the mixed solution, reacting the mixture for 24 to 48 hours at room temperature, then pouring the mixture into a dialysis bag, dialyzing the mixture for 48 hours with the deionized water, and drying the mixture in a vacuum drying oven until the weight of the mixture is constant to obtain the water-soluble caproylated carboxymethyl chitosan derivative.

Advantages and advantageous effects of the invention

The temperature-sensitive carboxymethyl chitosan derivative is prepared by hexanoylation reaction, and the substitution degree of the product can be controlled by controlling the molar ratio of the reactant carboxymethyl chitosan to the n-hexanoic anhydride, so that the derivative has temperature sensitivity and the application field of the carboxymethyl chitosan is expanded. In addition, the material can be used for preparing temperature-sensitive hydrogel, can generate sol-gel transformation in response to temperature change, and has potential application value in the fields of injectable drug sustained-release carriers, tissue engineering scaffolds, wound healing and the like.

Drawings

FIG. 1 is a structural formula diagram of hexanoyl carboxymethyl chitosan involved in the invention.

Detailed Description

Example 1

Dispersing 0.2 g carboxymethyl chitosan powder in 25 ml deionized water, placing on a magnetic stirrer at room temperature, stirring until the carboxymethyl chitosan powder is completely dissolved, then adding 25 ml anhydrous methanol, stirring for 30 minutes at room temperature, adding 0.075 ml n-hexanoic anhydride into the mixed solution by using a pipette, reacting for 24 hours at room temperature, then pouring into a dialysis bag, dialyzing for 48 hours with the deionized water, and drying in a vacuum drying oven to constant weight to obtain the water-soluble caproylated carboxymethyl chitosan derivative.

Example 2

Dispersing 0.2 g carboxymethyl chitosan powder in 25 ml deionized water, placing on a magnetic stirrer at room temperature, stirring until the carboxymethyl chitosan powder is completely dissolved, then adding 25 ml anhydrous methanol, stirring for 30 minutes at room temperature, adding 0.15 ml n-hexanoic anhydride into the mixed solution by using a pipette, reacting for 24 hours at room temperature, then pouring into a dialysis bag, dialyzing for 48 hours with the deionized water, and drying in a vacuum drying oven to constant weight to obtain the water-soluble caproylated carboxymethyl chitosan derivative.