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Preparation method of antimicrobial functionalized chitosan derivative

A technology for chitosan derivatives and chitosan transformation is applied in the field of preparation of antibacterial functionalized chitosan derivatives, which can solve the problems of insufficient water solubility of chitosan, antibacterial properties, influence, and low substitution degree. , to achieve the effect of improving antibacterial and solubility, high biosafety, and simple reaction process

Inactive Publication Date: 2017-09-29
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the existence of the α-amino group in arginine, it can also react with the activated amino acid of the carboxyl group, which makes the arginine self-polymerization serious, resulting in the side chain of the guanidino-functionalized chitosan derivative obtained by arginine modification. The low degree of substitution does not fully improve the water solubility and antibacterial properties of chitosan, which largely affects its application as a green natural antibacterial agent

Method used

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  • Preparation method of antimicrobial functionalized chitosan derivative

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Embodiment 1

[0032] Weigh 0.1 gram of chitosan and add it to 100 milliliters of 0.1M dilute hydrochloric acid, and mechanically stir at room temperature to dissolve the chitosan completely, thereby obtaining a 0.1% chitosan dilute acid solution by mass; A mixed solution of guanidinoacetic acid, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) for 3 hours ( The solvent is a buffer solution of 10mM 2-(N-morpholino)ethanesulfonic acid (MES), pH=4.5) 20mL is added in the above-mentioned chitosan dilute acid solution, wherein chitosan, guanidinoacetic acid, NHS, EDC The ratio of the amount of the substance is 10:1:5:5, after 12 hours of continuous stirring reaction at 35 ° C, add the hydroxylamine hydrochloride with the amount of guanidinoacetic acid and other substances to terminate the reaction; filter the insoluble matter in the reaction solution, and then Transfer the filtrate into a dialysis bag, seal both ends of the dialysis bag tightly...

Embodiment 2

[0034] Take by weighing 1.0 gram of chitosan and join in the dilute hydrochloric acid of 100 milliliters 0.2M, mechanically stir at room temperature so that chitosan dissolves completely, thereby obtain the chitosan dilute acid solution that mass percentage is 1.0%; A mixed solution of guanidinoacetic acid, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) activated for 2 hours (the solvent is the buffer solution of 2-(N-morpholino)ethanesulfonic acid (MES) of 25mM, pH=5.0) 35mL is added in above-mentioned chitosan dilute acid solution, wherein chitosan, guanidinoacetic acid, NHS, The ratio of the amount of substances in EDC is 2:2:5:5, after 24 hours of continuous stirring reaction at room temperature, add hydroxylamine hydrochloride with the amount of guanidinoacetic acid and other substances to terminate the reaction; filter the insoluble matter in the reaction solution, and then Transfer the filtrate to a dialysis bag, sea...

Embodiment 3

[0036]Take by weighing 10.0 gram chitosan and join in the dilute hydrochloric acid of 100 milliliters 0.3M, under room temperature mechanical stirring makes chitosan dissolve completely, thereby obtain the chitosan dilute acid solution that mass volume percent concentration is 9.1%; A mixture of guanidinoacetic acid, N-hydroxysuccinimide (NHS) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC·HCl) activated for 1 hour Solution (solvent is 50mM buffer solution of 2-(N-morpholino)ethanesulfonic acid (MES), pH=6.5) 20mL is added in above-mentioned chitosan dilute acid solution, wherein chitosan, guanidinoacetic acid, NHS , The ratio of the amount of EDC to the substance is 1:5:5:5, after 48 hours of continuous stirring reaction at 15°C, add hydroxylamine hydrochloride with the amount of guanidinoacetic acid and other substances to terminate the reaction; filter to remove insoluble matter in the reaction solution , then transfer the filtrate into a dialysis bag,...

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Abstract

The invention provides a preparation method of an antimicrobial functionalized chitosan derivative. The antimicrobial functionalized chitosan derivative is obtained by enabling chitosan and guanidineacetic acid to be subjected to an amidation reaction. The method comprises the following steps: (1) dissolving the chitosan in a diluted acid solution to obtain a chitosan and diluted acid water solution; (2) carrying out carboxyl activation on the guanidineacetic acid to obtain an activated guanidineacetic acid mixed solution; (3) mixing the mixed solution obtained in the step (2) with the chitosan and diluted acid water solution, and stirring for reacting; (4) adding hydroxylamine hydrochloride into reaction liquid for terminating the reaction; (5) filtering the reaction liquid and then carrying out dialysis in deionized water; after dialysis is completed, carrying out freeze drying treatment to obtain the antimicrobial functionalized chitosan derivative. The method avoids the problem of amino acid self-aggregation caused by carrying out guanidine functionalization by using arginine in the traditional method, and is simple in reaction process, mild in conditions and suitable for industrial production. The prepared antimicrobial functionalized chitosan derivative improves the antibacterial property and solubility while guaranteeing higher biological safety.

Description

technical field [0001] The invention relates to the field of chitosan preparation, in particular to a preparation method of antibacterial functionalized chitosan derivatives. Background technique [0002] Chitosan (β-(1,4)-2-amino-2-deoxy-D-glucose) is a natural alkaline polysaccharide with good biocompatibility and biodegradability. It is obtained after deacetylation of chitin, a natural organic compound next to cellulose. Due to its special physical and chemical properties and biological characteristics, chitosan has many excellent functions such as lowering blood sugar, regulating lipid metabolism, inhibiting microbial growth, moisture absorption and moisturizing, and is called the sixth element of life. It is used in medicine, food, chemical industry and environmental protection. and other fields have broad application prospects. Especially as an antibacterial macromolecule, due to its good biocompatibility, low toxicity, and degradability, it has become one of the res...

Claims

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Application Information

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IPC IPC(8): C08B37/08
CPCC08B37/003
Inventor 牛忠伟朱萌蒋士冬
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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