Abstract
Chitosan is an active biopolymer, and the combination of it with other active groups can be a valuable method to improve the potential application of the resultant derivatives in food, cosmetics, packaging materials, and other industries. In this paper, a series of N,N,N-trimethyl-O-(ureidopyridinium)acetyl chitosan derivatives were synthesized. The combination of chitosan with ureidopyridinium group and quaternary ammonium group made it achieve developed water solubility and biological properties. The structures of chitosan and chitosan derivatives were confirmed by FTIR, 1H NMR spectra, and elemental analysis. The prepared chitosan derivatives were evaluated for antioxidant property by 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging ability, hydroxyl radical scavenging ability, and superoxide radical scavenging ability. The results revealed that the synthesized chitosan derivatives exhibited improved antioxidant activity compared with chitosan. The chitosan derivatives were also investigated for antifungal activity against Phomopsis asparagus as well as Botrytis cinerea, and they showed a significant inhibitory effect on the selected phytopathogen. Meanwhile, CCK-8 assay was used to test the cytotoxicity of chitosan derivatives, and the results showed that most derivatives had low toxicity. These data suggested to develop analogs of chitosan derivatives containing ureidopyridinium group and quaternary ammonium group, which will provide a new kind of promising biomaterials having decreased cytotoxicity as well as excellent antioxidant and antimicrobial activity.
Highlights
With the popularization of the concept of environmental protection, searching for environmentally friendly biomaterials has become a new direction of scientific development
N,N,N-trimethyl chitosan was treated as a semi-finished material to prepare derivatives strategy of N,N,N-trimethyl-O-(ureidopyridinium)acetyl chitosan derivatives shown in Scheme 1
Elemental analysis confirmed the degrees of substitution of synthesized derivatives
Summary
With the popularization of the concept of environmental protection, searching for environmentally friendly biomaterials has become a new direction of scientific development. Abundant polysaccharides are attractive biomaterials for various applications such as food wrapper, tissue engineering scaffolds, drug delivery vehicles, flocculating agents, and cosmetics, due to their non-toxicity, biocompatibility, and biodegradability properties [1]. In this regard, chitosan, as a natural polysaccharide, has a extensive prospect in application of biomaterials [2,3]. Quaternary ammonium chitosan salt maintains the unique characteristics of chitosan and possesses better solubility and biological activities, so it plays an important role in the development of new functional chitosan derivatives [15,16]. Britto et al had evaluated the biocompatibility of chitosan and chitosan quaternary salt coatings as edible coatings for sliced apple
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