中华医学超声杂志

应用化学 ›› 2011, Vol. 28 ›› Issue (09): 1017-1021.DOI: 10.3724/SP.J.1095.2011.00489

• 研究论文 • 上一篇    下一篇

季铵化N,O-(2-羧乙基)壳聚糖的制备及其抗菌性能

蔡照胜1,2,孙岳明1*,杨春生2,朱雪梅2   

  1. (1.东南大学材料科学与工程学院 南京 211189；2.盐城工学院化学与生物工程学院 盐城)
  • 收稿日期:2010-08-23 修回日期:2010-10-28 出版日期:2011-09-10 发布日期:2011-09-10
  • 通讯作者: 孙岳明，教授; Tel:025-83792637; Fax:025-52090621; E-mail:sun@seu.edu.cn; 研究方向：光电功能材料、线性光学材料及天然高分子化学利用
  • 基金资助:
    国家973基础研究项目资助(2007CB936300)；江苏省自然科学基金项目资助(BK2009293)

Preparation of Quaternized N,O-(2-Carboxyethyl) Chitosans and Their Antibacterial Activity

CAI Zhaosheng1,2, SUN Yueming1*, YANG Chunsheng2, ZHU Xuemei2   

  1. (1.School of Materials Science and Engineering,Southeast University,Nanjing 211189;
    2.Department of Chemical and Biological Engineering,Yancheng Institute of Technology,Yancheng)
  • Received:2010-08-23 Revised:2010-10-28 Published:2011-09-10 Online:2011-09-10
  • Contact: Sun Yue-ming Sun

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摘要：

以缩水甘油基三甲基氯化铵(GTMA)、缩水甘油基三乙基氯化铵(GTEA)、缩水甘油基三丙基氯化铵(GTPA)、缩水甘油基三丁基氯化铵(GTBA)和缩水甘油基二甲基苄基氯化铵(GDMBA)等活性季铵盐为季铵化试剂，对N,O-2-羧乙基壳聚糖（N,O-2-CEC）进行了化学改性，得到了系列季铵化N,O-2-CEC(QCECs)；用电位滴定法测定了QCECs的季铵化度（DQ），分光光度法测定了N,O-2-CEC和QCECs的等电点（pHiep）；用琼脂平板法测定了N,O-2-CEC及其季铵化衍生物对金黄色葡萄球菌（S.aureus）和大肠杆菌（E.coli）的最低抑菌浓度（MIC值），并根据N,O-2-CEC及其季铵化衍生物对这2种微生物的MIC值评价了它们的抗菌活性。 结果表明，实验条件下得到的QCECs的DQ值在51.3%～59.1%间；N,O-2-CEC及其季铵化产物的等电点在6.44～7.30间，且季铵基团的引入会导致pHiep增大；除GTMA改性N,O-2-CEC的产物外，其它QCECs的pHiep随其季铵化度提高都有所增大；N,O-2CEC和QCECs对S.aureus和E.coli均具有抗菌活性，且QCECs的MIC值均低于N,O-2-CEC的MIC值；同时，季铵基团中烃基碳数的增加及二甲基苄基结构的存在可提高QCECs的抑菌能力。

关键词: N,O-羧乙基壳聚糖, 季铵化改性, 等电点, 最小抑菌浓度, 抗菌活性

Abstract:

A series of amphoteric polymeric electrolyte was prepared and their antibacterial activities and dissolving behaviour in water were investigated. A series of quaternized N,O-2-carboxyethyl chitosans(QCECs), which exhibit typical behaviour as amphoteric electrolyte, were obtained through the chemical modifications of N,O-(2-carboxyethyl)chitosan(N,O-2-CEC) by 2,3-epoxypropyl trialkyl ammonium chlorides including glycidyl trimethyl ammonium chloride(GTMA), glycidyl triethyl ammonium chloride(GTEA), glycidyl tripropyl ammonium chloride(GTPA), glycidyl tributyl ammonium chloride(GTBA) and glycidyl dimethylbenzyl ammonium chloride(GDMBA). Substitution degree of quaternization(DQ) of QCECs was determined by the potentiometry, in which the variations of potential of solution with the volume of AgNO3 aqueous solution were measured. The isoeletric points(pHiep) of N,O-2-CEC and its quaternized derivatives were determined by spectrometry method. The antibacterial activities of chitosan derivatives including N,O-2-CEC and QCECs were evaluated according to their minimum inhibition concentrations(MICs) against E.coli, a typical Gram-negative bacterium, and S.aureus, a typical Gram-positive bacterium, determined by agar plate method. DQ values of QCECs were estimated in the range of 51.3%～59.1%, the pHiep of N,O-2-CEC and QCECs were in the range of 6.44～7.30 and the introduction of quaternizing group resulted in the accretion of pHiep. Except the product obtained from the modification of N,O-2-CEC by GTMA, the pHiep values of all other QCECs increased along with their DQ contents. All N,O-2-CEC and their quaternized derivatives showed improved antibacterial activity against E.coli and S.aureus. The MIC values of QCECs were lower than those of N,O-2-CEC. The increase of carbon chain length of alkyl and the presence of dimethyl-benzyl in the quaternary ammonium groups could endow QCECs with much better antimicrobial activity.

Key words: N,O-(Carboxyethyl)chitosan, Quaternizing modification, Isoeletric point, Minimum inhibition concentration

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