Amphipathic chitosan quaternary ammonium salt derivative and preparation and application thereof

A chitosan quaternary ammonium salt and derivative technology, applied in the field of antibacterial materials, can solve the problems of complex synthesis process, non-biodegradability and high cost, and achieve the effects of simple synthesis steps, reduced drug resistance and low cost

Inactive Publication Date: 2017-03-15
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are antimicrobial materials synthesized with the antimicrobial peptide structure as a template, which have excellent antibacterial properties and very low hemolytic toxicity, but most of these materials are not biodegradable, which brings uncertainty to their application (Kuroda&Caputo, Antimicrobial polymers as synthetics of host -defense peptides.Wiley Interdiscip.Rev.Nanomed.Nanobiotechnol.,2013,5:49-66)
Singapore Yang et al. have prepared biodegradable amphiphilic antibacterial materials using polyester, but the synthesis process is very complicated and the cost is high (Engler et al. Antimicrobial polycarbonates: investigating the impact of balancing charge and hydrophobicity using a same-centered polymer approach. Biomacromolecules ,2013,14:4331-4339)

Method used

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  • Amphipathic chitosan quaternary ammonium salt derivative and preparation and application thereof
  • Amphipathic chitosan quaternary ammonium salt derivative and preparation and application thereof
  • Amphipathic chitosan quaternary ammonium salt derivative and preparation and application thereof

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Experimental program
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Effect test

Embodiment 1

[0046] (1) Preparation of chitosan quaternary ammonium salt:

[0047] The viscosity-average molecular weight of chitosan is 6000, the degree of polymerization is 37, and the degree of deacetylation is 92%;

[0048] Weigh 6.0g of chitosan and place it in a three-necked flask, measure 90mL of deionized water to dissolve the reactants, stir at 60°C for 1h, and mix the moles of glycidyltrimethylammonium chloride with the moles of chitosan The ratio of the degree of polymerization is 1:1. Dissolve glycidyltrimethylammonium chloride in 60mL of deionized water, slowly add it dropwise into a three-necked flask, stir for 30 minutes, and adjust the reaction temperature to 80°C. 9h, finally the solution obtained by the reaction was precipitated with acetone that accounted for 3 times the volume of the solution obtained by the reaction, left to stand for centrifugation, washed with acetone, and dried. Finally, the dried product was dissolved in an appropriate amount of deionized water, an...

Embodiment 2

[0059] Except that the mass ratio of propionaldehyde and chitosan quaternary ammonium salt is 1:10, all the other operations are with embodiment 1, obtain the amphiphilic chitosan quaternary ammonium salt derivative containing N-propyl of different propyl substitution degrees (PQC-1), the degree of propyl grafting is 7.5%.

[0060] The structural formula of amphiphilic chitosan quaternary ammonium salt containing N-propyl is shown in formula I:

[0061]

[0062] In formula Ⅰ, R 1 It is a 2-hydroxypropyltrimethylammonium chloride group, and its structure is shown in formula II:

[0063]

[0064] In formula II, X is Cl;

[0065] R 2 is a propyl group; a, b, and c are degrees of polymerization, a=17, b=14, c=3, and a+b+c=34.

[0066] The degree of grafting of quaternary ammonium salt and propyl group is determined by the peak intensity of NMR spectrum. In the nuclear magnetic spectrum of the prepared amphiphilic chitosan quaternary ammonium salt derivatives containing ...

Embodiment 3

[0068] Except that the mass ratio of propionaldehyde and chitosan quaternary ammonium salt is 1:0.5, all the other operations are with embodiment 1, obtain the amphiphilic chitosan quaternary ammonium salt derivative containing N-propyl of different propyl substitution degrees (PQC-2), the degree of propyl grafting is 18.7%.

[0069] The structural formula of amphiphilic chitosan quaternary ammonium salt containing N-propyl is shown in formula I:

[0070]

[0071] In formula Ⅰ, R 1 It is a 2-hydroxypropyltrimethylammonium chloride group, and its structure is shown in formula II:

[0072]

[0073] In formula II, X is Cl;

[0074] R 2 is a propyl group; a, b, and c are degrees of polymerization, a=14, b=14, c=6, and a+b+c=34.

[0075] The degree of grafting of quaternary ammonium salt and propyl group is determined by the peak intensity of NMR spectrum. In the nuclear magnetic spectrum of the prepared amphiphilic chitosan quaternary ammonium salt derivatives containin...

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Abstract

The invention discloses an amphipathic chitosan quaternary ammonium salt derivative and preparation thereof and application thereof. The structural formula of the amphipathic chitosan quaternary ammonium salt derivative is shown as in the description, wherein R1 is a 2-hydroxypropyl trimethyl ammonium halide group, R2 is alkyl or aromatic alkyl, and all a, b and c are polymerization degrees. The amphipathic chitosan quaternary ammonium salt derivative has excellent water solubility, degradability and biocompatibility, can effectively restrain the growth of gram negative bacteria and gram positive bacteria and can directly serve as antibacterial materials or can be used for preparing antibacterial composites. A preparation method of the amphipathic chitosan quaternary ammonium salt derivative is green, environmentally friendly, mild in reaction condition, low in cost and easy to industrialize.

Description

technical field [0001] The invention relates to the technical field of antibacterial materials, in particular to an amphiphilic chitosan quaternary ammonium salt derivative and its preparation and application. Background technique [0002] The invasion of microorganisms is ubiquitous, and antibiotics are widely used in various fields of life as an effective broad-spectrum antibacterial drug; at the same time, the abuse of antibiotics has also triggered a series of problems related to bacterial resistance, superbugs, environmental pollution, etc. Therefore, research on new antibacterial drugs has received more and more attention. [0003] In terms of antibacterial, nature has a good guiding role for human beings. When various animals, plants and microorganisms resist external bacteria, they will secrete some small molecule polypeptide substances with antibacterial, antiviral and antitumor activities, referred to as antibacterial peptides. It is composed of 13-45 amino acids...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/08A01N43/16A01P1/00
CPCA01N43/16C08B37/003
Inventor 陈彦涛赵慧李求龙玲张宏佳何晓君
Owner SHENZHEN UNIV
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