Antimicrobial activity of chitosan N-betainates

被引:93
作者
Holappa, Jukka
Hjalmarsdottir, Martha
Masson, Mar
Runarsson, Ogmundur
Asplund, Tomas
Soininen, Pasi
Nevalainen, Tapio
Jarvinen, Tomi
机构
[1] Univ Kuopio, Dept Pharmaceut Chem, FIN-70211 Kuopio, Finland
[2] Reykjavik Univ, Sch Sci & Engn, Dept Biomed Sci, IS-110 Reykjavik, Iceland
[3] Univ Iceland, Fac Pharm, IS-107 Reykjavik, Iceland
[4] Ciba Specialty Chem Oy, Water & Paper Treatment, Surface & Coatings R&D, FIN-21201 Raisio, Finland
[5] Univ Kuopio, Dept Chem, FIN-70211 Kuopio, Finland
基金
芬兰科学院;
关键词
chitosan; synthesis; quaternary; water-soluble; antimicrobial;
D O I
10.1016/j.carbpol.2005.11.041
中图分类号
O69 [应用化学];
学科分类号
081704 [应用化学];
摘要
The effect of degree of substitution on the antimicrobial activity of water-soluble quaternary chitosan N-betainates was determined against Escherichia coli and Staphylococcus aureus. Chitosan N-betainates showed low antimicrobial activity in neutral conditions and the glucosamine N-betainate prepared as a reference compound showed low activity also in acidic conditions. However, the antimicrobial activity increased with decreasing degrees of substitution in acidic conditions (pH 5.5), which suggests that for efficient antimicrobial action, the positive charge should be situated in the amino group of chitosan, rather than in the quaternary substituent. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码:114 / 118
页数:5
相关论文
共 29 条
[1]
Factors affecting the susceptibility of Staphylococcus aureus CCRC 12657 to water soluble lactose chitosan derivative [J].
Chen, YL ;
Chou, CC .
FOOD MICROBIOLOGY, 2005, 22 (01) :29-35
[2]
Preparation and important functional properties of water-soluble chitosan produced through Maillard reaction [J].
Chung, YC ;
Kuo, CL ;
Chen, CC .
BIORESOURCE TECHNOLOGY, 2005, 96 (13) :1473-1482
[3]
DALY WH, 2001, Patent No. 6306835
[4]
Application to a cartilage targeting strategy:: Synthesis and in vivo biodistribution of 14C-labeled quaternary ammonium-glucosamine conjugates [J].
Giraud, I ;
Rapp, M ;
Maurizis, JC ;
Madelmont, JC .
BIOCONJUGATE CHEMISTRY, 2000, 11 (02) :212-218
[5]
IMPACT OF PH AND CATIONIC SUPPLEMENTATION ON INVITRO POSTANTIBIOTIC EFFECT [J].
GUDMUNDSSON, A ;
ERLENDSDOTTIR, H ;
GOTTFREDSSON, M ;
GUDMUNDSSON, S .
ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1991, 35 (12) :2617-2624
[6]
Chitosan disrupts the barrier properties of the outer membrane of Gram-negative bacteria [J].
Helander, IM ;
Nurmiaho-Lassila, EL ;
Ahvenainen, R ;
Rhoades, J ;
Roller, S .
INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY, 2001, 71 (2-3) :235-244
[7]
N-chloroacyl-6-O-triphenylmethylchitosans:: Useful intermediates for synthetic modifications of chitosan [J].
Holappa, J ;
Nevalainen, T ;
Soininen, P ;
Elomaa, M ;
Safin, R ;
Másson, M ;
Järvinen, T .
BIOMACROMOLECULES, 2005, 6 (02) :858-863
[8]
Synthesis and characterization of chitosan N-betainates having various degrees of substitution [J].
Holappa, J ;
Nevalainen, T ;
Savolainen, J ;
Soininen, P ;
Elomaa, M ;
Safin, R ;
Suvanto, S ;
Pakkanen, T ;
Masson, M ;
Loftsson, T ;
Järvinen, T .
MACROMOLECULES, 2004, 37 (08) :2784-2789
[9]
Antimicrobial effect of chitooligosaccharides produced by bioreactor [J].
Jeon, YJ ;
Park, PJ ;
Kim, SK .
CARBOHYDRATE POLYMERS, 2001, 44 (01) :71-76
[10]
Synthesis and antibacterial activities of quaternary ammonium salt of chitosan [J].
Jia, ZS ;
Shen, DF ;
Xu, WL .
CARBOHYDRATE RESEARCH, 2001, 333 (01) :1-6