Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt

SUN Xueqi; ZHANG Jingjing; MI Yingqi; MIAO Qin; TAN Wenqiang; LI Qing; GUO Zhanyong

doi:10.1007/s00343-021-0352-2

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Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt

Biology | Updated：2023-04-27

- Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt
- Journal of Oceanology and Limnology Vol. 40, Issue 1, Pages: 284-295(2022)
- Affiliations：
  
  1.Key Laboratory of Coastal Biology and Bioresource Utilization, Yantai Institute of Coastal Zone Research, Chinese Academy of Sciences, Yantai 264003, China
  2.Center for Ocean Mega-Science, Chinese Academy of Sciences, Qingdao 266071, China
  3.University of Chinese Academy of Sciences, Beijing 100049, China
- Author bio：
  
  Zhanyong GUO, zhanyongguo@hotmail.com
- Funds：
- DOI：10.1007/s00343-021-0352-2
  CLC：
- Received：24 September 2020，
  
  Accepted：19 January 2021，
  
  Online First：26 January 2021，
  
  Published：2022-01
- Accepted：
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SUN Xueqi, ZHANG Jingjing, MI Yingqi, et al. Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt[J]. Journal of Oceanology and Limnology, 2022, 40(1): 284-295.
DOI：

SUN Xueqi, ZHANG Jingjing, MI Yingqi, et al. Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt[J]. Journal of Oceanology and Limnology, 2022, 40(1): 284-295. DOI： 10.1007/s00343-021-0352-2.

摘要

Abstract

To improve the solubility and bioactivity of chitosan

a new class of carboxymethyl chitosan derivatives possessing sulfonium salts was successfully designed and synthesized

including Methyl sulfide carboxymethyl chitosan (MCMCS)

Ethyl sulfide carboxymethyl chitosan (ECMCS)

Propyl sulfide carboxymethyl chitosan (PCMCS)

and Butyl sulfide carboxymethyl chitosan (BCMCS). To determine the structure of the new class of the derivatives

methods of the Fourier transform infrared spectroscopy (FT-IR)

H nuclear magnetic resonance spectrometer (

H NMR)

and

C nuclear magnetic resonance spectrometer (

C NMR) were used. Moreover

the antioxidant activity of the derivatives for three types of free radicals

i.e.

hydroxyl radical

superoxide radical

and 1

1-diphenyl-2-picrylhydrazyl (DPPH) radical was evaluated in vitro. In addition

the L929 cells were adopted to test the cytotoxicity of chitosan and its derivatives by CCK-8 assay. The class of the carboxymethyl chitosan derivatives showed a strong scavenging ability against the three free radicals at 1.6 mg/mL

with scavenging rate of over 70% and some up to 100%. At this high rate

the overall cell viability in the toxicity test reached more than 80%

indicating that the synthetic derivative had a little cytotoxicity. The results show that the introduction of carboxymethyl group to chitosan increased the water-solubility of chitosan

and the combination of sulfonate ions with different chain lengths further enhanced the antioxidant activity of chitosan. Therefore

the sulfonium-containing carboxymethyl chitosan derivatives had excellent bioactivity with good application prospects in food

biomedicine

and medical fields.

关键词

Keywords

references

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Related Institution

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Laboratory for Marine Biology and Biotechnology, Qingdao Marine Science and Technology Center

CAS and Shandong Province Key Laboratory of Experimental Marine Biology, Center for Ocean Mega-Science, Institute of Oceanology, Chinese Academy of Sciences

Jiangsu Innovation Center of Marine Bioresources, Jiangsu Coast Development Investment Co., Ltd., Jiangsu Coast Development Group Co., Ltd.

College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology

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