Studies on the synthesis and antibacterial activities of polymeric quaternary ammonium salts from dimethylaminoethyl methacrylate

被引:316
作者
Lu, Guiqian [1 ]
Wu, Dingcai [1 ]
Fu, Ruowen [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, PCFM Lab, Inst Mat Sci, Guangzhou 510275, Peoples R China
基金
高等学校博士学科点专项科研基金; 中国国家自然科学基金;
关键词
azo polymer; polymeric quaternary ammonium salts; biopolymer; antibacterial activity;
D O I
10.1016/j.reactfunctpolym.2007.01.008
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Four quaternary ammonium salt monomers were synthesized from dimethylaminoethyl methacrylate (DMAEMA) by quaternization with benzyl] chloride (BC), butyl bromide (BB), dodecyl bromide (DB) or hexadecyl bromide (HB), respectively. And then, the monomers were homopolymerized to obtain four polymeric quaternary ammonium materials with different lengths of alkyl chain, which were referred to as poly(DMAEMA-BC), poly(DMAEMA-BB), poly(DMAEMA-BB) and poly(DMAEMA-HB), respectively. The resultant monomers and related polymers were characterized by elemental analysis, FTIR, NMR, thermogravimetric analysis (TGA) and so on. Their bactericidal activities were evaluated by determining minimum bactericidal concentration (MBC) values and inhibitory zone diameters against Grampositive bacteria (S. aureus) and Gram-negative bacteria (E. coli), respectively. The results showed that the MBC values of monomer DMAEMA-DB and DMAEMA-HB were 12-24 mu g/mL against E. coli and S. aureus. However, the MBC values of monomer DMAEMA-BC and DMAEMA-BB were higher than 50 mg/mL against test microbe. It was very interesting that poly(DMAEMA-BC) and poly(DMAEMA-BB) exhibited greater bactericidal activities than their precursory monomers, but poly(DMAEMA-DB) and poly(DMAEMA-HB) present contrary results. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:355 / 366
页数:12
相关论文
共 39 条
[1]   Influence of concentration and structure of quaternary ammonium salts on their antifouling efficiency tested against a community of marine bacteria [J].
Baudrion, F ;
Périchaud, A ;
Vacelet, E .
BIOFOULING, 2000, 14 (04) :317-331
[2]   Antibacterial activity of dental composites containing quaternary ammonium polyethylenimine nanoparticles against Streptococcus mutans [J].
Beyth, N ;
Yudovin-Farber, I ;
Bahir, R ;
Domb, AJ ;
Weissa, E .
BIOMATERIALS, 2006, 27 (21) :3995-4002
[3]   Radiation grafting of N,N-dimethylaminoethylmethacrylate and 4-vinylpyridine onto polypropylene by the one- and two-step methods [J].
Bucio, E ;
Aliev, R ;
Burillo, G .
POLYMER BULLETIN, 2002, 47 (06) :571-577
[4]   Synthesis and characterization of novel antimicrobial cationic polyelectrolytes [J].
Cakmak, I ;
Ulukanli, Z ;
Tuzcu, M ;
Karabuga, S ;
Genctav, K .
EUROPEAN POLYMER JOURNAL, 2004, 40 (10) :2373-2379
[5]   Radiation grafting of N,N-dimethylaminoethylmethacrylate onto poly(ethylene terephthalate) [J].
Carreón, MP ;
Aliev, R ;
Ocampo, R ;
Burillo, G .
POLYMER BULLETIN, 2000, 44 (03) :331-335
[6]   Biocide resistance mechanisms [J].
Chapman, JS .
INTERNATIONAL BIODETERIORATION & BIODEGRADATION, 2003, 51 (02) :133-138
[7]   Quaternary ammonium functionalized poly(propylene imine) dendrimers as effective antimicrobials: Structure-activity studies [J].
Chen, CZS ;
Beck-Tan, NC ;
Dhurjati, P ;
van Dyk, TK ;
LaRossa, RA ;
Cooper, SL .
BIOMACROMOLECULES, 2000, 1 (03) :473-480
[8]   Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers [J].
Dizman, B ;
Elasri, MO ;
Mathias, LJ .
JOURNAL OF APPLIED POLYMER SCIENCE, 2004, 94 (02) :635-642
[9]   A new approach to chemically modified chitosan sulfates and study of their influences on the inhibition of Escherichia coli and Staphylococcus aureus growth [J].
Huang, RH ;
Du, YM ;
Zheng, LS ;
Liu, H ;
Fan, LH .
REACTIVE & FUNCTIONAL POLYMERS, 2004, 59 (01) :41-51
[10]   EFFECT OF CHLORHEXIDINE ON ELECTROPHORETIC MOBILITY CYTOPLASMIC CONSTITUENTS DEHYDROGENASE ACTIVITY AND CELL WALLS OF ESCHERICHIA COLI AND STAPHYLOCOCCUS AUREUS [J].
HUGO, WB ;
LONGWORTH, AR .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1966, 18 (09) :569-+