Synthesis, characterization, and the antioxidant activity of double quaternized chitosan derivatives

Lijie Wei, Qing Li, Wenqiang Tan, Fang Dong, Fang Luan, Zhanyong Guo, Luciano Saso, L. Dux, Grzegorz Wegrzyn, T. Csont

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts' quantity, single quaternized chitosan N-phenmethyl-N,N-dimethyl chitosan (PDCS), double quaternized chitosan N-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan (MP2MDCS), N-(1-pyridylmethyl-3-ylmethyl)-N,N-dimethyl chitosan (MP3MDCS), and N-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan (MP4MDCS) were designed and synthesized successfully through chemical modification of chitosan. Besides, three kinds of antioxidant activities, including hydroxyl radicals, superoxide radicals, and 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radicals were tested in vitro. As shown in this paper, the scavenging ability was ranking in order of MP3MDC > MP4MDCS > MP2MDCS > PDCS > chitosan at 1.6 mg/mL in all assays. All double quaternary ammonium salts were better than chitosan or the single quaternary ammonium salt. In addition, MP3MDCS could scavenge hydroxyl radicals totally at 1.6 mg/mL. MP2MDCS and MP4MDCS with more than 90% scavenging indices both had great scavenging ability on hydroxyl radicals or DPPH radicals. Furthermore, these data demonstrated that the increasing number of the positive charge would improve the antioxidant property of chitosan derivatives, and the N-pyridinium position would influence the scavenging radical ability.

Original languageEnglish
Article number501
JournalMolecules
Volume22
Issue number3
DOIs
Publication statusPublished - Mar 1 2017

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scavenging
antioxidants
Chitosan
hydroxyl radicals
Antioxidants
salts
Derivatives
Scavenging
Ammonium Compounds
synthesis
Salts
Hydroxyl Radical
pesticides
ranking
inorganic peroxides
polysaccharides
medicine
food
solubility
Chemical modification

Keywords

  • Antioxidant activity
  • Chemical modification
  • Double quaternized chitosan
  • Single quaternized chitosan

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis, characterization, and the antioxidant activity of double quaternized chitosan derivatives. / Wei, Lijie; Li, Qing; Tan, Wenqiang; Dong, Fang; Luan, Fang; Guo, Zhanyong; Saso, Luciano; Dux, L.; Wegrzyn, Grzegorz; Csont, T.

In: Molecules, Vol. 22, No. 3, 501, 01.03.2017.

Research output: Contribution to journalArticle

Wei, Lijie ; Li, Qing ; Tan, Wenqiang ; Dong, Fang ; Luan, Fang ; Guo, Zhanyong ; Saso, Luciano ; Dux, L. ; Wegrzyn, Grzegorz ; Csont, T. / Synthesis, characterization, and the antioxidant activity of double quaternized chitosan derivatives. In: Molecules. 2017 ; Vol. 22, No. 3.
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AB - With the specialty of improving the water solubility of chitosan, quaternary ammonium salts have broadened the application of this polysaccharide in food, medicine and pesticides. To identify the effect of quaternary ammonium salts' quantity, single quaternized chitosan N-phenmethyl-N,N-dimethyl chitosan (PDCS), double quaternized chitosan N-(1-pyridylmethyl-2-ylmethyl)-N,N-dimethyl chitosan (MP2MDCS), N-(1-pyridylmethyl-3-ylmethyl)-N,N-dimethyl chitosan (MP3MDCS), and N-(1-pyridylmethyl-4-ylmethyl)-N,N-dimethyl chitosan (MP4MDCS) were designed and synthesized successfully through chemical modification of chitosan. Besides, three kinds of antioxidant activities, including hydroxyl radicals, superoxide radicals, and 1,1-Diphenyl-2-picrylhydrazyl (DPPH) radicals were tested in vitro. As shown in this paper, the scavenging ability was ranking in order of MP3MDC > MP4MDCS > MP2MDCS > PDCS > chitosan at 1.6 mg/mL in all assays. All double quaternary ammonium salts were better than chitosan or the single quaternary ammonium salt. In addition, MP3MDCS could scavenge hydroxyl radicals totally at 1.6 mg/mL. MP2MDCS and MP4MDCS with more than 90% scavenging indices both had great scavenging ability on hydroxyl radicals or DPPH radicals. Furthermore, these data demonstrated that the increasing number of the positive charge would improve the antioxidant property of chitosan derivatives, and the N-pyridinium position would influence the scavenging radical ability.

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