[1]王林,辛梅华,李明春,等.胍基化壳聚糖季铵盐的制备及其抗菌性能[J].华侨大学学报(自然科学版),2023,44(1):79-86.[doi:10.11830/ISSN.1000-5013.202210005]
 WANG Lin,XIN Meihua,LI Mingchun,et al.Preparation and Antibacterial Properties of Guanidine Chitosan Quaternary Ammonium Salt[J].Journal of Huaqiao University(Natural Science),2023,44(1):79-86.[doi:10.11830/ISSN.1000-5013.202210005]
点击复制

胍基化壳聚糖季铵盐的制备及其抗菌性能()
分享到:

《华侨大学学报(自然科学版)》[ISSN:1000-5013/CN:35-1079/N]

卷:
第44卷
期数:
2023年第1期
页码:
79-86
栏目:
出版日期:
2023-01-10

文章信息/Info

Title:
Preparation and Antibacterial Properties of Guanidine Chitosan Quaternary Ammonium Salt
文章编号:
1000-5013(2023)01-0079-08
作者:
王林 辛梅华 李明春 雷嘉华
华侨大学 材料科学与工程学院, 福建 厦门 361021
Author(s):
WANG Lin XIN Meihua LI Mingchun LEI Jiahua
College of Materials Science and Engineering, Huaqiao University, Xiamen 361021, China
关键词:
壳聚糖 季铵盐 聚六亚甲基双胍 三聚氯氰 抗菌活性
Keywords:
chitosan quaternary ammonium salt poly(hexamethylene biguanide) cyanuric chloride antibacterial activity
分类号:
O636.1
DOI:
10.11830/ISSN.1000-5013.202210005
文献标志码:
A
摘要:
以三聚氯氰(TCT)为中间桥梁,将聚六亚甲基双胍(PHMB)接枝到N-(2-羟丙基-3-甲基氯化铵)壳聚糖(HTCC)上,制备胍基壳聚糖季铵盐(HCP).研究制备HCP的最佳反应条件,采用元素分析、傅里叶变换红外光谱(FTIR)和核磁共振氢谱(1H NMR)对产物的结构进行表征,并测试其抗菌性能.得到HCP的最佳反应条件为HTCC和TCT的摩尔比1.0∶2.5,HTCC和PHMB的质量比1.0∶1.2,缚酸剂为三乙胺,TCT一取代的反应时间8 h,二取代的反应时间14 h,反应温度40 ℃.结果表明:制得的HCP对大肠杆菌(E. coli)和金黄色葡萄球菌(S. aureus)的最低抑菌质量浓度分别为0.020,0.005 mg·mL-1;质量浓度为1.0 mg·mL-1的HCP对E. coli和S. aureus的抑菌率分别为89.8%和100.0%,高于相同质量浓度下HTCC对E. coli和S. aureus的抑菌率18.2%和18.7%.
Abstract:
Guanidine chitosan quaternary ammonium salt(HCP)was prepared by grafting poly(hexamethylene biguanide)(PHMB)onto N-(2-hydroxypropyl trimethylammonium chloride)chitosan(HTCC)using cyanuric chloride(TCT)as the intermediate bridge, and the optimum reaction conditions for the preparation of HCP were studied. The structure of the product was characterized by elemental analysis, Fourier transform infrared spectroscopy(FTIR)and nuclear magnetic resonance hydrogen spectroscopy(1H NMR), and its antibacterial properties were tested. The optimum reaction conditions of HCP were obtained as follows: the molar ratio of HTCC and TCT was 1.0∶2.5, the mass ratio of HTCC and PHMB was 1.0∶1.2, the acid binding agent was triethylamine, the reaction time of one substitution of TCT was 8 h, the reaction time of two substitution was 14 h, and the reaction temperature was 40 ℃. The results showed that the minimum inhibitory mass concentrations of HCP against Escherichia coli(E. coli)and Staphylococcus aureus(S. aureus)were 0.020 and 0.005 mg·mL-1, respectively. The inhibition rates of HCP with mass concentration of 1.0 mg·mL-1 on E. coli and S. aureus were 89.8% and 100.0%, respectively, which were higher than those of HTCC at the same mass concentration on E. coli and S. aureus by 18.2% and 18.7%.

参考文献/References:

[1] YU Huan,LIU Lin,YANG Huawei,et al.Water-insoluble polymeric guanidine derivative and application in the preparation of antibacterial coating of catheter[J].ACS Applied Materials Interfaces,2018,10(45):39257-39267.DOI:10.1021/acsami.8b13868.
[2] ALVES P J,BARRETO R T,BARROIS B M,et al.Update on the role of antiseptics in the management of chronic wounds with critical colonisation and/or biofilm[J].International Wound Journal,2021,18(3):342-358.DOI:10.1111/iwj.13537.
[3] MASSARELLI E,SILVA D,PIMENTA A.F.R,et al.Polyvinyl alcohol/chitosan wound dressings loaded with antiseptics[J].International Journal of Pharmaceutics,2021,593:120110.DOI:10.1016/j.ijpharm.2020.120110.
[4] NI Yunzhou,QIAN Zhixiang,YIN Yu,et al.Polyvinyl alcohol/chitosan/polyhexamethylene biguanide phase separation system: A potential topical antibacterial formulation with enhanced antimicrobial effect[J].Molecules,2020,25(6):1334-1346.DOI:10.3390/molecules25061334.
[5] LIN Y J,CHANG CHIEN B Y,LEE Y H.Injectable and thermoresponsive hybrid hydrogel with Antibacterial, Anti-inflammatory, oxygen Transport, and enhanced cell growth activities for improved diabetic wound healing[J].European Polymer Journal,2022,175:111364.DOI:10.1016/j.eurpolymj.2022.111364.
[6] NG I S,OOI C W,LIU B L,et al.Antibacterial efficacy of chitosan- and poly(hexamethylene biguanide)-immobilized nanofiber membrane[J].International Journal of Biological Macromolecules,2020,154:844-854.DOI:10.1016/j.ijbiomac.2020.03.127.
[7] PENG Wan,YIN Hua,LIU Peiming,et al.Covalently construction of poly(hexamethylene biguanide)as high-efficiency antibacterial coating for silicone rubber[J].Chemical Engineering Journal,2021,412:128707.DOI:10.1016/j.cej.2021.128707.
[8] SONG Xiaoming,ZHANG Luyao,WANG Yan,et al.Long term antibacterial effect cellulose film was modified with polyhexamethylene biguanide(PHMB)[J].Industrial Crops and Products,2022,184:115038.DOI:10.1016/j.indcrop.2022.115038.
[9] BAKSHI P S,SELVAKUMAR D,KADIRVELU K,et al.Chitosan as an environment friendly biomaterial: A review on recent modifications and applications[J].International Journal of Biological Macromolecules,2020,150:1072-1083.DOI:10.1016/j.ijbiomac.2019.10.113.
[10] 车秋凌,辛梅华,李明春,等.O-一氯均三嗪-N,N,N-三甲基壳聚糖的合成及其在羊毛织物抗菌中的应用[J].化工进展,2018,37(3):1098-1104.DOI:10.16085/j.issn.1000-6613.2017-1955.
[11] OYERVIDES-MUNOZ E,POLLET E,ULRICH G,et al.Original method for synthesis of chitosan-based antimicrobial agent by quaternary ammonium grafting[J].Carbohydrate Polymers,2017,157:1922-1932.DOI:10.1016/j.carbpol.2016.11.081.
[12] WANG Huafu,YAO Chen,QIAN Kun,et al.Balance of disinfection and cytotoxicity of hydroxypropyltrimethyl ammonium chloride chitosan with polyhexamethylene biguanide at low concentrations[J].Journal of Macromolecular Science,Part A,2017,54(12):923-930.DOI:10.1080/10601325.2017.1381922.
[13] ABRI S,GHATPANDE A,RESS J,et al.Polyionic complexed antibacterial heparin-chitosan particles for antibiotic delivery[J].ACS Applied Bio Materials,2019,2:5848-5858.DOI:10.1021/acsabm.9b00833.
[14] XU Fanxuan,OOI C W,LIU Binglan,et al.Antibacterial efficacy of poly(hexamethylene biguanide)immobilized on chitosan/dye-modified nanofiber membranes[J].International Journal of Biological Macromolecules,2021,181:508-520.DOI:10.1016/j.ijbiomac.2021.03.151.
[15] ZHANG Kai,HELM J,PESCHEL D,et al.NMR and FT Raman characterisation of regioselectively sulfated chitosan regarding the distribution of sulfate groups and the degree of substitution[J].Polymer,2010,51:4698-4705.DOI:10.1016/j.polymer.2010.08.034.
[16] 王林,辛梅华,李明春,等.催化氢化还原法制备的N,N-双烷基化壳聚糖[J].华侨大学学报(自然科学版),2019,40(3):350-355.DOI:10.11830/ISSN.1000-5013.201903029.
[17] 李雪菲.基于薄荷醇的新型抗菌高分子材料[D].北京:北京化工大学,2019.
[18] SCHMIDT A,MORDHORST T.Synthesis of 4-(dimethyl)pyridinium-substituted pyrazine, pyridazine, 1,3,5-triazine, purine, and imidazole[J].Heterocycles,2006,68(7):1393-1400.DOI:10.3987/COM-06-10748.
[19] 张月华,光善仪,郗娇娇,等.一种以三聚氯氰为桥基的新型小分子功能活性染料的合成[J].合成化学,2016,24(9):804-807.DOI:10.15952/j.cnki.cjsc.1005-1511.2016.09.15394.
[20] 李玮,李明春,辛梅华.糠醛改性O-季铵化壳聚糖衍生物的合成及其抗菌性能[J].化工进展,2014,33(4):966-970,987.DOI:10.3969/j.issn.1000-6613.2014.04.030.
[21] 王贝,王仲,刘桂艳,等.环境友好型消毒剂PHMB-HCl的合成工艺优化[J].生物化工,2022,8(4):112-116.
[22] ZHOU Z X,WEI D F,GUAN Y,et al.Damage of Escherichia coli membrane by bactericidal agent polyhexamethylene guanidine hydrochloride: Micrographic evidences[J].Journal of Applied Microbiology,2010,108(3):898-907.DOI:10.1111/j.1365-2672.2009.04482.x.

相似文献/References:

[1]陈世年.从米根霉细胞壁寻找天然壳聚糖研究(Ⅰ)[J].华侨大学学报(自然科学版),1995,16(3):323.[doi:10.11830/ISSN.1000-5013.1995.03.0323]
 Chen Shinian.Searching after Natural Chitosan from Cell Wall of Rhizopus Oryzae(Ⅰ)[J].Journal of Huaqiao University(Natural Science),1995,16(1):323.[doi:10.11830/ISSN.1000-5013.1995.03.0323]
[2]陈世年.从米根霉细胞壁寻找天然壳聚糖的研究(Ⅲ)[J].华侨大学学报(自然科学版),1996,17(1):74.[doi:10.11830/ISSN.1000-5013.1996.01.0074]
 Chen Shinian.Searching after Natural Chitosan from Cell Wall of Rhizopus Oryzae(Ⅲ)[J].Journal of Huaqiao University(Natural Science),1996,17(1):74.[doi:10.11830/ISSN.1000-5013.1996.01.0074]
[3]陈世年.从米根霉细胞壁寻找天然壳聚糖的研究(Ⅲ)[J].华侨大学学报(自然科学版),1996,17(4):399.[doi:10.11830/ISSN.1000-5013.1996.04.0399]
 Chen Shinian.Searching after Natural Chitosan from Cell Wall of Rhizopus Oryzae(Ⅲ)[J].Journal of Huaqiao University(Natural Science),1996,17(1):399.[doi:10.11830/ISSN.1000-5013.1996.04.0399]
[4]陈世年.从米根霉细胞壁寻找天然壳聚糖的研究(Ⅲ)[J].华侨大学学报(自然科学版),1997,18(1):80.[doi:10.11830/ISSN.1000-5013.1997.01.0080]
 Chen Shinian.Searching after Natural Chitosan from Cell Wall of Rhizopus Oryzae(Ⅲ)[J].Journal of Huaqiao University(Natural Science),1997,18(1):80.[doi:10.11830/ISSN.1000-5013.1997.01.0080]
[5]黄惠莉,林文銮.壳聚糖微球树脂的制备及应用[J].华侨大学学报(自然科学版),2002,23(1):91.[doi:10.3969/j.issn.1000-5013.2002.01.020]
 Huang Huili,Lin Wenluan.Preparation and Application of Chitosan Microsphere-Resin[J].Journal of Huaqiao University(Natural Science),2002,23(1):91.[doi:10.3969/j.issn.1000-5013.2002.01.020]
[6]刘斌,孙向英,徐金瑞.壳聚糖在分析化学中的应用[J].华侨大学学报(自然科学版),2003,24(3):225.[doi:10.3969/j.issn.1000-5013.2003.03.001]
 Liu Bin,Sun Xiangying,Xu Jinrui.Application of Chitosan to Analytical Chemistry[J].Journal of Huaqiao University(Natural Science),2003,24(1):225.[doi:10.3969/j.issn.1000-5013.2003.03.001]
[7]黄理耀,刘超.疏水化长脂肪链酰化壳聚糖的制备[J].华侨大学学报(自然科学版),2005,26(4):439.[doi:10.3969/j.issn.1000-5013.2005.04.028]
 Huang Liyao,Liu Chao.Preparation of Hydrophobing Acyl Chitosan with Long Fatly Chain[J].Journal of Huaqiao University(Natural Science),2005,26(1):439.[doi:10.3969/j.issn.1000-5013.2005.04.028]
[8]杨芸,连惠婷,刘斌,等.敌百虫分子印迹聚合物的合成及其性能[J].华侨大学学报(自然科学版),2009,30(3):284.[doi:10.11830/ISSN.1000-5013.2009.03.0284]
 YANG Yun,LIAN Hui-ting,LIU Bin,et al.Preparation and Properties of Trichlorfon Molecularly Imprinted Polymers[J].Journal of Huaqiao University(Natural Science),2009,30(1):284.[doi:10.11830/ISSN.1000-5013.2009.03.0284]
[9]孙亚飞,林金清,左霜,等.功能化季铵盐离子液体在制备生物柴油中的应用[J].华侨大学学报(自然科学版),2011,32(6):657.[doi:10.11830/ISSN.1000-5013.2011.06.0657]
 SUN Ya-fei,LIN Jin-qing,ZUO Shuang,et al.Application of Synthesis Biodiesel by Functional Qauternary Ammonium Ionic Liquid[J].Journal of Huaqiao University(Natural Science),2011,32(1):657.[doi:10.11830/ISSN.1000-5013.2011.06.0657]
[10]王林,辛梅华,李明春,等.催化氢化还原法制备的N,N-双烷基化壳聚糖[J].华侨大学学报(自然科学版),2019,40(3):350.[doi:10.11830/ISSN.1000-5013.201903029]
 WANG Lin,XIN Meihua,LI Mingchun,et al.N,N-Dialkylated Chitosan Made by Catalytic Hydrogenation Reduction[J].Journal of Huaqiao University(Natural Science),2019,40(1):350.[doi:10.11830/ISSN.1000-5013.201903029]

备注/Memo

备注/Memo:
收稿日期: 2022-10-12
通信作者: 李明春(1962-),男,教授,博士,博士生导师,主要从事功能高分子材料的研究.E-mail:mcli@hqu.edu.cn.
基金项目: 福建省科技计划项目(2019H6014, 2020Y4012)http://www.hdxb.hqu.edu.cn
更新日期/Last Update: 2023-01-20