Abstract
Copolymers of quaternary ammonium monomer(QAM) and hydrophilic co-monomer were successfully synthesized by free radical polymerization. It was discovered that the hydrophilic co-monomers with poor antibacterial activity significantly enhanced the activity of QAM substituted with a long alkyl chain[i.e., N,N-dimethyl-N-dodecyl methacrylate ammonium bromide(DMAEMA-DB)]. When a suitable molar ratio of DMAEMA-DB to co-monomer was selected, the activity of the copolymers was up to 123 times that of the homopolymer of DMAEMA-DB against S. aureus, and 282 times that of it against E. coli. But unlike DMAEMA-DB, the co-monomers might weaken the activity of QAM substituted with a short alkyl chain[i.e., N,N-dimethyl-N-butyl methacrylate ammonium bromide(DMAEMA-BB)]. Moreover, it was found that copolymers of DMAEMA-DB were much more biocidal than those of DMAEMA-BB. Therefore, it could be speculated that the long alkyl chain plays an important role in the antibacterial activity, and that the hydrophilic co-monomers are beneficial to polymeric guaternary ammonium compounds(PQACs) to exert the positive effect of the long alkyl chain to the greatest degree.
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Caro A., Humblot V., Méthivier C., Minier M., Salmain M. I., Pradier C. M., J. Phys. Chem. B., 2009, 113(7), 2101
Martinez L., Cilla I., Beltran J. A., Roncales P., J. Food. Sci., 2006, 71(1), 48
Yoshida K., Tanagawa M., Atsuta M., J. Biomed. Mater. Res., 1999, 47(4), 516
Das K., Bose S., Bandyopadhyay A., Karandikar B., Gibbins B. L., J. Biomed. Mater. Res. B., 2008, 87(2), 455
Ong S. Y., Wu J., Moochhala S. M., Tan M. H., Lu J., Biomaterials, 2008, 29(32), 4323
Ozolins M., Eady E. A., Avery A. J., Cunliffe W. J., Po A. L. W., O’Neill C., Simpson N. B., Walters C. E., Carnegie E., Lewis J. B., Dada J., Haynes M., Williams K., Williams H. C., Lancet, 2004, 364(9452), 2188
Efstratiou M., Papaioannou W., Nakou M., Ktenas E., Vrotsos I. A., Panis V., J. Dent., 2007, 35(4), 331
Roy D., Knapp J. S., Guthrie J. T., Perrier S., Biomacromolecule, 2007, 9(1), 91
Huang J. Y., Murata H., Koepsel R. R., Russell A. J., Matyjaszewski K., Biomacromolecules, 2007, 8(5), 1396
Xing X. D., Wang X. G., Acta. Polym. Sin., 2009, (2), 187
Punyani S., Singh H., J. Appl. Polym. Sci., 2008, 107(5), 2861
Tatsuo T., Macromol. Mater. Eng., 2001, 286(2), 63
Ilker M. F., Nusslein K., Tew G. N., Coughlin E. B., J. Am. Chem. Soc., 2004, 126(48), 15870
Dizman B., Elasri M. O., Mathias L. J., J. Polym. Sci. Pol. Chem., 2006, 44(20), 5965
Pasquier N., Keul H., Heine E., Moeller M., Angelov B., Linser S., Willumeit R., Macromol. Biosci., 2008, 8(10), 903
Murata H., Koepsel R. R., Matyjaszewski K., Russell A. J., Biomaterials, 2007, 28(32), 4870
Kanazawa A., Ikeda T., Endo T., J. Polym. Sci. Polym. Chem., 1993, 31(6), 1441
Lenoir S., Pagnoulle C., Galleni M., Compere P., Jerome R., Detrembleur C., Biomacromolecules, 2006, 7(8), 2291
Lu G. Q., Zuo H. J., Dong W. M., Wu D. C., Fu R. W., Chem. Res. Chinese Universities, 2011, 27(6), 1072
Thorsteinsson T., Masson M., Kristinsson K. G., Hjalmarsdottir M. A., Hilmarsson H., Loftsson T., J. Med. Chem., 2003, 46(19), 4173
Lu G. Q., Wu D. C., Fu R. W., Reac. Funct. Polym., 2007, 67(4), 355
Tiller J. C., Liao C. J., Lewis K., Klibanov A. M., P. Natl. Acad. Sci. USA, 2001, 98(11), 5981
Chen C. Z., Beck-Tan N. C., Dhurjati P., van Dyk T. K., La Rossa R. A., Cooper S. L., Biomacromolecules, 2000, 1(3), 473
Nonaka T., Watanabe T., Kawabata T., Kurihara S., J. Appl. Polym. Sci., 2001, 79(1), 115
Roy D., Knapp J. S., Guthrie J. T., Perrier S., Biomacromolecules, 2008, 9 (1), 91
Grapski J. A., Cooper S. L., Biomaterials, 2001, 22(16), 2239
Zuo H. J., Wu D. C., Fu R. W., Polym. J., 2010, 42(9), 766
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Supported by the National Natural Science Foundation of China(No.50673101), the Scientific Foundation of Guangdong Province of China(Nos.0711020600015, 2004A30404001), the Natural Science Foundation of Guangxi Zhuang Autonomous Region of China(Nos.2013GXNSFBA019040, 2013GXNSFBA019036), the Projcet of Department of Education of Guangxi Zhuang Autonomous Region, China(No.2013YB171) and the Foundation of Guangxi University of Science and Technology, China.
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Zuo, H., Wen, W., Wu, D. et al. Antibacterial activity of polymeric quaternary ammonium compounds tuned by incorporating hydrophilic co-monomer. Chem. Res. Chin. Univ. 31, 160–166 (2015). https://doi.org/10.1007/s40242-015-4248-6
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DOI: https://doi.org/10.1007/s40242-015-4248-6