Synthesis and antibacterial research of hydantoin modified quaternary ammonium chitosan

doi:10.16085/j.issn.1000-6613.2015.01.033

Chemical Industry and Engineering Progree ›› 2015, Vol. 34 ›› Issue (1): 188-192,233.DOI: 10.16085/j.issn.1000-6613.2015.01.033

Previous Articles Next Articles

Synthesis and antibacterial research of hydantoin modified quaternary ammonium chitosan

CHEN Yanyan, LI Mingchun, XIN Meihua, LIN Yihua

School of Material Science and Engineering, Engineering Research Center of Environment-Friendly Functional Materials, Ministry of Education, Huaqiao University, Xiamen 361021, Fujian, China

Received:2014-04-24 Revised:2014-05-28 Online:2015-01-05 Published:2015-01-05

海因改性N-季铵化壳聚糖衍生物的合成及其抗菌性能

陈燕燕, 李明春, 辛梅华, 林意华

华侨大学材料科学与工程学院, 环境友好功能材料教育部工程中心, 福建厦门 361021

通讯作者: 辛梅华,教授,博士生导师,研究方向为功能高分子材料研究。E-mail mhxin@hqu.edu.cn。
作者简介:陈燕燕(1987-),女,硕士研究生。
基金资助:
福建省重点科技项目(2009H0030)、福建省自然科学基金(2011J01312和2012J01396)及科技部科技人员服务企业项目(2009GJC40030)。

Abstract

Abstract: Under acidic condition, N-(2-hydroxy)propyl-3-trimethyl ammonium chloride chitosan (HTCC) was synthesized by reaction of chitosan and glycidy quaternized salts. Then 3-glycidy-5, 5- dimethyl hydantoin (made in our lab) was used to synthesize O-hydroxy-propyl (5, 5-dimethyl hydantoin)-N-(2-hydroxy)propyl-3-trimethyl ammonium chloride chitosan (GH-HTCC). The products were confirmed by FTIR, ¹H NMR, UV-VIS, EA. The results of antibacterial tests indicated antibacterial activity of these products with better antimicrobial activity against S. aureus than against E. coil. Antibacterial activity of GH-HTCC was stronger than HTCC and increased as the degree of substitution increased. A lower concentration of EDTA improved antibacterial activity of HTCC and GH-HTCC, but a higher concentration of EDTA inhibited antibacterial activity.

Key words: chitosan, quaternized, 3-glycidyl-5,5-dimethyl hydantoin, EDTA, antibacterial activity

摘要： 在酸性条件下,以壳聚糖与环氧季铵盐为原料反应得到水溶性良好的产物N-(2-羟丙基三甲基氯化铵)壳聚糖(HTCC),再用实验室自制的环氧海因改性,得到O-羟丙基(5,5-二甲基海因)-N-(2-羟丙基三甲基氯化铵)壳聚糖衍生物(GH-HTCC),用 FTIR、¹H NMR、UV-VIS和EA 等对产物进行表征。抗菌实验结果表明,产物对两种菌种都有一定的抗菌活性,对金黄色葡萄球菌的抗菌活性优于大肠杆菌;GH-HTCC的抗菌活性优于HTCC,并随环氧海因取代度的增加而增强;低浓度的乙二胺四乙酸(EDTA)增强了HTCC和GH-HTCC的抗菌活性,而高浓度的EDTA在一定程度上抑制了二者的抗菌活性。

关键词: 壳聚糖, 季铵化, 环氧海因, 乙二胺四乙酸, 抗菌活性

CLC Number:

O636.1

CHEN Yanyan, LI Mingchun, XIN Meihua, LIN Yihua. Synthesis and antibacterial research of hydantoin modified quaternary ammonium chitosan[J]. Chemical Industry and Engineering Progree, 2015, 34(1): 188-192,233.

陈燕燕, 李明春, 辛梅华, 林意华. 海因改性N-季铵化壳聚糖衍生物的合成及其抗菌性能[J]. 化工进展, 2015, 34(1): 188-192,233.

References

[1] Kumar M N V R,Muzzarelli R A A,Muzzarelli C,et al. Chitosan chemistry and pharmaceutical perspectives[J].Chemical Review,2004,104:6017-6084.

[2] Qin C Q,Xiao Q,Li H,et al. Calorimetric studies of the action of chitosan-N-2-hydroxypropyl trimethyl ammonium chloride on the growth of microorganisms[J]. International Journal of Biological Macromolecules,2004,34:121-126.

[3] Xu T,Xin M H,Li M C,et al.Synthesis,characteristic and antibacterial activity of N,N,N-trimethyl chitosan and its carboxymethyl derivatives[J]. Carbohydrate Polymers,2010,81:931-936.

[4] 魏文珑,温艳珍,李彦威,等. 海因类杀菌剂的研究进展[J]. 山西化工,2005,25(1):11-14.

[5] Li R,Pei H,Ren X H,et al. Antimicrobial N-halamine modified chitosan films[J].Carbohydrate Polymers,2013,92:534-539.

[6] Yang J H,Cai J,Hu Y,et al. Preparation,characterization and antimicrobial activity of 6-amino-6-deoxychitosan[J]. Carbohydrate Polymers,2012,87:202-209.

[7] Liang J,Chen Y J,Ren X H,et al. Fabric treated with antimicrobial N-halamine epoxides[J]. Industrial Engineering Chemistry Research,2007,46:6425-6429.

[8] 毛扬帆,李明春,辛梅华,等. O-季铵化改性壳聚糖固载环糊精的制备及其载药性能[J].化工进展,2010,29(9):1705-1709.

[9] Espinosa M H,Del Toro P J O,Silva D Z. Microstructural analysis of poly(glycidyl methacrylate) by ¹H and ¹³C NMR spectroscopy[J]. Polymer,2001,42:3393-3397.

[10] Kou L,Liang J,Ren X,et al. Synthesis of a water-soluble siloxane copolymer and its application for antimicrobial coatings[J]. Industrial & Engineering Chemistry Research,2009,48:6521-6526.

[11] Cho J,Grant J,Piquette M M,et al. Synthesis and physicochemical and dynamic mechanical properties of a water-soluble chitosan derivative as a biomaterial[J]. Biomacromolecules,2006,7:2845-2855.

[12] 刘宏民. 实用有机光谱分析[M]. 郑州:郑州大学出版社,2008:14-16.

[13] Lisbeth T H,John W A,Tom A G. Antibacterial effect of protamine in combination with EDTA and refrigeration[J]. International Journal of Food Microbiology,2001,66:149-161.

[14] Chung Y C,Wang H L,Chen Y M,et al. Effect of abiotic factors on the antibacterial activity of chitosan against waterborne pathogens[J]. Bioresource Technology,2003,88:179-186.

[15] Amany A E S,Mohamed H. Chitosan-EDTA new combination is a promising candidate for treatment of bacterial and fungal infections[J]. Current Microbiology,2011,62:739-745.

Synthesis and antibacterial research of hydantoin modified quaternary ammonium chitosan

海因改性N-季铵化壳聚糖衍生物的合成及其抗菌性能

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	WANG Shaofan, ZHOU Ying, HAO Kang’an, HUANG Anrong, ZHANG Ruju, WU Chong, ZUO Xiaoling. Self-healing and blue-light hydrogel with pH responsiveness [J]. Chemical Industry and Engineering Progress, 2023, 42(9): 4837-4846.
[2]	WANG Lin, XIN Meihua, LI Mingchun, CHEN Qi, MAO Yangfan. Preparation of quaternized/sulfonated chitosan and its anti-biofilm activity [J]. Chemical Industry and Engineering Progress, 2023, 42(5): 2577-2585.
[3]	WANG Lin, XIN Meihua, LI Mingchun, ZHANG Tao, MAO Yangfan. Preparation of alkyl quaternized chitosan and its anti-biofilm activity [J]. Chemical Industry and Engineering Progress, 2023, 42(4): 1995-2002.
[4]	WANG Xing, ZHAO Zilong, ZHANG Xiaoshan, WANG Hongjie, DONG Wenyi, CHEN Huihui. Influence of preparation conditions of biochar-supported iron catalyst on its decomplexation of Ni-EDTA and iron-leaching [J]. Chemical Industry and Engineering Progress, 2022, 41(9): 4831-4839.
[5]	FENG Ying, ZHAO Mengjie, CUI Qian, XIE Yuju, ZHANG Jianwei, DONG Xin. Research progress of molecular simulation technology in the development and application of chitosan functional materials [J]. Chemical Industry and Engineering Progress, 2022, 41(8): 4241-4253.
[6]	ZHOU Lisha, LI Ruonan, BIAN Yujie, CHEN Shunsheng. Preparation of TOCNF and magnetic carboxymethyl chitosan nanoparticles composite and adsorption properties of Pb²⁺ [J]. Chemical Industry and Engineering Progress, 2022, 41(2): 901-910.
[7]	ZHAO Xiao, CHEN Zhongshun, TANG Zhongqiang, SHI Xuan, DAI Chengyi, MA Xiaoxun. EDTA-assisted preparation of highly active catalysts for Fischer-Tropsch synthesis [J]. Chemical Industry and Engineering Progress, 2022, 41(2): 759-769.
[8]	Qihai LIU, Wanting XIE, Zhenyu JIA, Xiaohua ZHU, Ronghui WANG. Preparation of chitosan capsule materials and its sustained release properties [J]. Chemical Industry and Engineering Progress, 2021, 40(1): 339-345.
[9]	Ximing ZHENG, Rongyu FAN. Covalent modification of chitosan quaternary ammonium salt on microporous polypropylene membrane and its antibacterial properties [J]. Chemical Industry and Engineering Progress, 2021, 40(1): 332-338.
[10]	Xuguang LIU, Meihua XIN, Mingchun LI, Junkai XU, Lin WANG. Preparation and properties of chitosan/N-vinyl pyrrolidone copolymer [J]. Chemical Industry and Engineering Progress, 2020, 39(9): 3535-3542.
[11]	Yi ZHANG, Yingxue JIANG, Hao ZHANG. Preparation of quaternary ammonium modified chitosan and its application in antibacterial finishing of rabbit wool fabric [J]. Chemical Industry and Engineering Progress, 2020, 39(7): 2810-2816.
[12]	Yunlong ZHENG,Jinmei WANG,Zhengqi SUN,Zhicheng QIN,Yanan ZHOU. Preparation and application of chitosan/gelatin antibacterial microcapsule [J]. Chemical Industry and Engineering Progress, 2020, 39(3): 1137-1144.
[13]	Guijuan LI,Wei XIA,Haixi LUO,Guiru CHENG. Properties and in vitro cell compatibility of NCW-CS/PVA composite membranes [J]. Chemical Industry and Engineering Progress, 2020, 39(1): 356-364.
[14]	Junying SONG,Xuwen HE,Zhanbin HUANG. Stabilization of heavy metals in soil by chitosan and its derivatives [J]. Chemical Industry and Engineering Progress, 2019, 38(9): 4308-4319.
[15]	Haitian ZHAO,Xudong LI,Fengqin CAO,Yan NI,Lei YAO. Advances in preparation and application of chitosan-based nanoparticles for drug delivery system [J]. Chemical Industry and Engineering Progress, 2019, 38(11): 5057-5065.