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
- Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt
- 海洋湖沼学报（英文） 2022年40卷第1期页码：284-295
- 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：
  
  the National Key R & D Program of China(2019YFD0900705);the Key Deployment Projects of the Marine Science Research Center of the Chinese Academy of Sciences(COMS2020J04);the Natural Science Foundation of Shandong Province of China(ZR2019BD064);© Chinese Society for Oceanology and Limnology, Science Press and Springer-Verlag GmbH Germany, part of Springer Nature 2022
- DOI：10.1007/s00343-021-0352-2
  中图分类号：
- 收稿：2020-09-24，
  
  录用：2021-1-19，
  
  网络首发：2021-01-26，
  
  纸质出版：2022-01
- Accepted：
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Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt[J]. 海洋湖沼学报（英文）, 2022,40(1):284-295.

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.
Synthesis, characterization, and antioxidant activity of carboxymethyl chitosan derivatives containing sulfonium salt[J]. 海洋湖沼学报（英文）, 2022,40(1):284-295. DOI： 10.1007/s00343-021-0352-2.

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

J P Adjimani , P Asare . Antioxidant and free radical scavenging activity of iron chelators . Toxicology Reports , 2015 . 2 721 - 728 . DOI: 10.1016/j.toxrep.2015.04.005 http://doi.org/10.1016/j.toxrep.2015.04.005 .

M Almada , B H Leal-Martínez , N Hassan , M J Kogan , M G Burboa , A Topete , M A Valdez , J Juárez . Photothermal conversion efficiency and cytotoxic effect of gold nanorods stabilized with chitosan, alginate and poly(vinyl alcohol) . Materials Science and Engineering: C , 2017 . 77 583 - 593 . DOI: 10.1016/j.msec.2017.03.218 http://doi.org/10.1016/j.msec.2017.03.218 .

S Ankri , D Mirelman . Antimicrobial properties of allicin from garlic . Microbes and Infection , 1999 . 1 ( 2 ): 125 - 129 . DOI: 10.1016/S1286-4579(99)80003-3 http://doi.org/10.1016/S1286-4579(99)80003-3 .

M Burits , F Bucar . Antioxidant activity of Nigella sativa essential oil . Phytotherapy Research , 2000 . 14 ( 5 ): 323 - 328 . DOI: 10.1002/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO;2-Q http://doi.org/10.1002/1099-1573(200008)14:5<323::AID-PTR621>3.0.CO;2-Q .

J H Chen , C T Ho . Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds . Journal of Agricultural and Food Chemistry , 1997 . 45 ( 7 ): 2374 - 2378 . DOI: 10.1021/jf970055t http://doi.org/10.1021/jf970055t .

L Y Chen , Y M Du , X Q Zeng . Relationships between the molecular structure and moisture-absorption and moisture-retention abilities of carboxymethyl chitosan: II . Effect of degree of deacetylation and carboxymethylation. Carbohydrate Research , 2003 . 338 ( 7 ): 333 - 340 . DOI: 10.1016/S0008-6215(02)00462-7 http://doi.org/10.1016/S0008-6215(02)00462-7 .

L Y Chen , Z G Tian , Y M Du . Synthesis and pH sensitivity of carboxymethyl chitosan-based polyampholyte hydrogels for protein carrier matrices . Biomaterials , 2004a . 25 ( 17 ): 3725 - 3732 . DOI: 10.1016/j.biomaterials.2003.09.100 http://doi.org/10.1016/j.biomaterials.2003.09.100 .

S C Chen , Y C Wu , F L Mi , Y H Lin , L C Yu , H W Sung . A novel pH-sensitive hydrogel composed of N, O -carboxymethyl chitosan and alginate cross-linked by genipin for protein drug delivery . Journal of Controlled Release , 2004b . 96 ( 2 ): 285 - 300 . DOI: 10.1016/j.jconrel.2004.02.002 http://doi.org/10.1016/j.jconrel.2004.02.002 .

X G Chen , H J Park . Chemical characteristics of O -carboxymethyl chitosans related to the preparation conditions . Carbohydrate Polymers , 2003 . 53 ( 4 ): 355 - 359 . DOI: 10.1016/S0144-8617(03)00051-1 http://doi.org/10.1016/S0144-8617(03)00051-1 .

E S H El Ashry , E El-Rafey , N Rezki , H H Abou-Elnaga , W M A Bakry , Y M Boghdadi . Evaluation of some functionalized imidazoles and 1, 2, 4-triazoles as antioxidant additives for industrial lubricating oils and correlating the results with the structures of additives using empirical AM1 calculations . Journal of Saudi Chemical Society , 2014 . 18 ( 5 ): 443 - 449 . DOI: 10.1016/j.jscs.2011.09.010 http://doi.org/10.1016/j.jscs.2011.09.010 .

K H Gensch , I H Pitman , T Higuchi . Oxidation of thioethers to sulfoxides by iodine . II. catalytic role of some carboxylic acid anions. Journal of the American Chemical Society , 1968 . 90 ( 8 ): 2096 - 2104 . .

Z Y Guo , H Y Liu , X L Chen , X Ji , P C Li . Hydroxyl radicals scavenging activity of N-substituted chitosan and quaternized chitosan . Bioorganic & Medicinal Chemistry Letters , 2006 . 16 ( 24 ): 6348 - 6350 . DOI: 10.1016/j.bmcl.2006.09.009 http://doi.org/10.1016/j.bmcl.2006.09.009 .

Z Y Guo , R E Xing , S Liu , H H Yu , P B Wang , C P Li , P C Li . The synthesis and antioxidant activity of the Schiff bases of chitosan and carboxymethyl chitosan . Bioorganic & Medicinal Chemistry Letters , 2005 . 15 ( 20 ): 4600 - 4603 . DOI: 10.1016/j.bmcl.2005.06.095 http://doi.org/10.1016/j.bmcl.2005.06.095 .

Y X Hu , J Zhang , C W Yu , Q Li , F Dong , G Wang , Z Y Guo . Synthesis, characterization, and antioxidant properties of novel inulin derivatives with amino-pyridine group . International Journal of Biological Macromolecules , 2014 . 70 44 - 49 . DOI: 10.1016/j.ijbiomac.2014.06.024 http://doi.org/10.1016/j.ijbiomac.2014.06.024 .

R Jayakumar , M Prabaharan , S V Nair , S Tokura , H Tamura , N Selvamurugan . Novel carboxymethyl derivatives of chitin and chitosan materials and their biomedical applications . Progress in Materials Science , 2010 . 55 ( 7 ): 675 - 709 . DOI: 10.1016/j.pmatsci.2010.03.001 http://doi.org/10.1016/j.pmatsci.2010.03.001 .

S K Kim , N Rajapakse . Enzymatic production and biological activities of chitosan oligosaccharides (COS): a review . Carbohydrate Polymers , 2005 . 62 ( 4 ): 357 - 368 . DOI: 10.1016/j.carbpol.2005.08.012 http://doi.org/10.1016/j.carbpol.2005.08.012 .

Y H Kim , G H Kim , K S Yoon , S Shankar , J W Rhim . Comparative antibacterial and antifungal activities of sulfur nanoparticles capped with chitosan . Microbial Pathogenesis , 2020 . 144 104178 DOI: 10.1016/j.micpath.2020.104178 http://doi.org/10.1016/j.micpath.2020.104178 .

R S Li , Q H Wan . A thioether-embedded mixed-mode cyano-bonded chromatographic stationary phase: preparation, characterization and retention mechanism . Chromatographia , 2018 . 81 ( 12 ): 1623 - 1630 . DOI: 10.1007/s10337-018-3630-1 http://doi.org/10.1007/s10337-018-3630-1 .

G Y Lu , L J Kong , B Y Sheng , G Wang , Y D Gong , X F Zhang . Degradation of covalently cross-linked carboxymethyl chitosan and its potential application for peripheral nerve regeneration . European Polymer Journal , 2007 . 43 ( 9 ): 3807 - 3818 . DOI: 10.1016/j.eurpolymj.2007.06.016 http://doi.org/10.1016/j.eurpolymj.2007.06.016 .

L L Mensor , F S Menezes , G G Leitão , A S Reis , T C dos Santos , C S Coube , S G Leitão . Screening of Brazilian plant extracts for antioxidant activity by the use of DPPH free radical method . Phytotherapy Research , 2001 . 15 ( 2 ): 127 - 130 . DOI: 10.1002/ptr.687 http://doi.org/10.1002/ptr.687 .

Y Q Mi , W Q Tan , J J Zhang , L J Wei , Y Chen , Q Li , F Dong , Z Y Guo . Synthesis, characterization, and antifungal property of hydroxypropyltrimethyl ammonium chitosan halogenated acetates . Marine Drugs , 2018 . 16 ( 9 ): 315 DOI: 10.3390/md16090315 http://doi.org/10.3390/md16090315 .

V K Mourya , N N Inamdar . Chitosan-modifications and applications: opportunities galore . Reactive and Functional Polymers , 2008 . 68 ( 6 ): 1013 - 1051 . DOI: 10.1016/j.reactfunctpolym.2008.03.002 http://doi.org/10.1016/j.reactfunctpolym.2008.03.002 .

N Oh , K H Nam , M Goh , B C Ku , J G Kim , N H You . Synthesis of colorless and highly refractive poly(phenylene thioether ether) derived from 2, 7-(4, 4′-diphenol) thiothianthrene . Polymer , 2019 . 165 191 - 197 . DOI: 10.1016/j.polymer.2019.01.033 http://doi.org/10.1016/j.polymer.2019.01.033 .

R Priyadarshi , H J Kim , J W Rhim . Effect of sulfur nanoparticles on properties of alginate-based films for active food packaging applications . Food Hydrocolloids , 2021 . 110 106155 DOI: 10.1016/j.foodhyd.2020.106155 http://doi.org/10.1016/j.foodhyd.2020.106155 .

E I Rabea , M E T Badawy , C V Stevens , G Smagghe , W Steurbaut . Chitosan as antimicrobial agent: applications and mode of action . Biomacromolecules , 2003 . 4 ( 6 ): 1457 - 1465 . DOI: 10.1021/bm034130m http://doi.org/10.1021/bm034130m .

M Rinaudo . Chitin and chitosan: properties and applications . Progress in Polymer Science , 2006 . 31 ( 7 ): 603632 DOI: 10.1016/j.progpolymsci.2006.06.001 http://doi.org/10.1016/j.progpolymsci.2006.06.001 .

S Saedi , M Shokri , J W Rhim . Antimicrobial activity of sulfur nanoparticles: effect of preparation methods . Arabian Journal of Chemistry , 2020 . 13 ( 8 ): 6580 - 6588 . DOI: 10.1016/j.arabjc.2020.06.014 http://doi.org/10.1016/j.arabjc.2020.06.014 .

A R Saundane , Y Manjunatha . Synthesis, antimicrobial and antioxidant activities of 2-oxo-6-phenyl-2-yl-4-(2′-phenyl-5′-substituted 1H-indol-3′-yl)-1, 2-dihydro pyridin-3-carbonitriles and their derivatives . Arabian Journal of Chemistry , 2016 . 9 ( 1 ): S501 - S509 . DOI: 10.1016/j.arabjc.2011.06.011 http://doi.org/10.1016/j.arabjc.2011.06.011 .

L P Sun , Y M Du , L H Fan , X Chen , J H Yang . Preparation, characterization and antimicrobial activity of quaternized carboxymethyl chitosan and application as pulp-cap . Polymer , 2006 . 47 ( 6 ): 1796 - 1804 . DOI: 10.1016/j.polymer.2006.01.073 http://doi.org/10.1016/j.polymer.2006.01.073 .

W Q Tan , Q Li , F Dong , L J Wei , Z Y Guo . Synthesis, characterization, and antifungal property of chitosan ammonium salts with halogens . International Journal of Biological Macromolecules , 2016 . 92 293 - 298 . DOI: 10.1016/j.ijbiomac.2016.07.023 http://doi.org/10.1016/j.ijbiomac.2016.07.023 .

J H Wang , D D Li , W Tao , Y Lu , X Z Yang , J Wang . Synthesis of an oxidation-sensitive polyphosphoester bearing thioether group for triggered drug release . Biomacromolecules , 2019 . 20 ( 4 ): 1740 - 1747 . DOI: 10.1021/acs.biomac.9b00101 http://doi.org/10.1021/acs.biomac.9b00101 .

W S Xia , P Liu , J L Zhang , J Chen . Biological activities of chitosan and chitooligosaccharides . Food Hydrocolloids , 2011 . 25 ( 2 ): 170 - 179 . DOI: 10.1016/j.foodhyd.2010.03.003 http://doi.org/10.1016/j.foodhyd.2010.03.003 .

W M Xie , P X Xu , Q Liu . Antioxidant activity of water-soluble chitosan derivatives . Bioorganic & Medicinal Chemistry Letters , 2001 . 11 ( 13 ): 1699 - 1701 . DOI: 10.1016/S0960-894X(01)00285-2 http://doi.org/10.1016/S0960-894X(01)00285-2 .

R E Xing , S Liu , Z Y Guo , H H Yu , C P Li , X Ji , J H Feng , P C Li . The antioxidant activity of glucosamine hydrochloride in vitro . Bioorganic & Medicinal Chemistry , 2006 . 14 ( 6 ): 1706 - 1709 . DOI: 10.1016/j.bmc.2005.10.018 http://doi.org/10.1016/j.bmc.2005.10.018 .

T Xu , M H Xin , M C Li , H L Huang , S Q Zhou . Synthesis, characteristic and antibacterial activity of N, N, N -trimethyl chitosan and its carboxymethyl derivatives . Carbohydrate Polymers , 2010 . 81 ( 4 ): 931 - 936 . DOI: 10.1016/j.carbpol.2010.04.008 http://doi.org/10.1016/j.carbpol.2010.04.008 .

J J Zhang , W Q Tan , G Wang , X L Yin , Q Li , F Dong , Z Y Guo . Synthesis, characterization, and the antioxidant activity of N, N, N -trimethyl chitosan salts . International Journal of Biological Macromolecules , 2018 . 118 9 - 14 . DOI: 10.1016/j.ijbiomac.2018.06.018 http://doi.org/10.1016/j.ijbiomac.2018.06.018 .

J J Zhang , W Q Tan , L J Wei , Y Chen , Y Q Mi , X Q Sun , Q Li , F Dong , Z Y Guo . Synthesis of urea-functionalized chitosan derivatives for potential antifungal and antioxidant applications . Carbohydrate Polymers , 2019 . 215 108 - 118 . DOI: 10.1016/j.carbpol.2019.03.067 http://doi.org/10.1016/j.carbpol.2019.03.067 .

S Zhang , X D Liu , X D Jin , H F Li , J Sun , X Y Gu . The novel application of chitosan: Effects of cross-linked chitosan on the fire performance of thermoplastic polyurethane . Carbohydrate Polymers , 2018b . 189 313 - 321 . DOI: 10.1016/j.carbpol.2018.02.034 http://doi.org/10.1016/j.carbpol.2018.02.034 .

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