Antibacterial Activity of Polymeric Quaternary Ammonium Compounds Tuned by Incorporating Hydrophilic co-Monomer

doi:10.1007/s40242-015-4248-6

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (1): 160-166.doi: 10.1007/s40242-015-4248-6

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Antibacterial Activity of Polymeric Quaternary Ammonium Compounds Tuned by Incorporating Hydrophilic co-Monomer

ZUO Huajiang^1,2, WEN Wanhua¹, WU Dingcai¹, FU Ruowen¹, TANG Chunyi²

1. PCFM Laboratory, School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou 510275, P. R. China;
2. College of Biological and Chemical Engineering, Guangxi University of Science and Technology, Liuzhou 545006, P. R. China

Received:2014-07-02 Revised:2014-09-06 Online:2015-02-01 Published:2014-10-27
Contact: FU Ruowen, E-mail:cesfrw@mail.sysu.edu.cn E-mail:cesfrw@mail.sysu.edu.cn
Supported by:
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.

Abstract

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.

Key words: Polymeric quaternary ammonium compound, Antibacterial mechanism, Copolymerization, Hydropho-bic/hydrophilic balance

ZUO Huajiang, WEN Wanhua, WU Dingcai, FU Ruowen, TANG Chunyi. Antibacterial Activity of Polymeric Quaternary Ammonium Compounds Tuned by Incorporating Hydrophilic co-Monomer[J]. Chemical Research in Chinese Universities, 2015, 31(1): 160-166.

References

[1] Caro A., Humblot V., Méthivier C., Minier M., Salmain M. I., Pra-dier C. M., J. Phys. Chem. B., 2009, 113(7), 2101
[2] Martinez L., Cilla I., Beltran J. A., Roncales P., J. Food. Sci., 2006, 71(1), 48
[3] Yoshida K., Tanagawa M., Atsuta M., J. Biomed. Mater. Res., 1999, 47(4), 516
[4] Das K., Bose S., Bandyopadhyay A., Karandikar B., Gibbins B. L., J. Biomed. Mater. Res. B., 2008, 87(2), 455
[5] Ong S. Y., Wu J., Moochhala S. M., Tan M. H., Lu J., Biomaterials, 2008, 29(32), 4323
[6] 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
[7] Efstratiou M., Papaioannou W., Nakou M., Ktenas E., Vrotsos I. A., Panis V., J. Dent., 2007, 35(4), 331
[8] Roy D., Knapp J. S., Guthrie J. T., Perrier S., Biomacromolecule, 2007, 9(1), 91
[9] Huang J. Y., Murata H., Koepsel R. R., Russell A. J., Matyjaszewski K., Biomacromolecules, 2007, 8(5), 1396
[10] Xing X. D., Wang X.G., Acta. Polym. Sin., 2009, (2), 187
[11] Punyani S., Singh H., J. Appl. Polym. Sci., 2008, 107(5), 2861
[12] Tatsuo T., Macromol. Mater. Eng., 2001, 286(2), 63
[13] Ilker M. F., Nusslein K., Tew G. N., Coughlin E. B., J. Am. Chem. Soc., 2004, 126(48), 15870
[14] Dizman B., Elasri M. O., Mathias L. J., J. Polym. Sci. Pol. Chem., 2006, 44(20), 5965
[15] Pasquier N., Keul H., Heine E., Moeller M., Angelov B., Linser S., Willumeit R., Macromol. Biosci., 2008, 8(10), 903
[16] Murata H., Koepsel R. R., Matyjaszewski K., Russell A. J., Biomaterials, 2007, 28(32), 4870
[17] Kanazawa A., Ikeda T., Endo T., J. Polym. Sci. Polym. Chem., 1993, 31(6), 1441
[18] Lenoir S., Pagnoulle C., Galleni M., Compere P., Jerome R., Detrembleur C., Biomacromolecules, 2006, 7(8), 2291
[19] Lu G. Q., Zuo H. J., Dong W. M., Wu D. C., Fu R. W., Chem. Res. Chinese Universities, 2011, 27(6), 1072
[20] Thorsteinsson T., Masson M., Kristinsson K. G., Hjalmarsdottir M. A., Hilmarsson H., Loftsson T., J. Med. Chem., 2003, 46(19), 4173
[21] Lu G. Q., Wu D. C., Fu R. W., Reac. Funct. Polym., 2007, 67(4), 355
[22] Tiller J. C., Liao C. J., Lewis K., Klibanov A. M., P. Natl. Acad. Sci. USA, 2001, 98(11), 5981
[23] 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
[24] Nonaka T., Watanabe T., Kawabata T., Kurihara S., J. Appl. Polym. Sci., 2001, 79(1), 115
[25] Roy D., Knapp J. S., Guthrie J. T., Perrier S., Biomacromolecules, 2008, 9(1), 91
[26] Grapski J. A., Cooper S. L., Biomaterials, 2001, 22(16), 2239
[27] Zuo H. J., Wu D. C., Fu R. W., Polym. J., 2010, 42(9), 766

Antibacterial Activity of Polymeric Quaternary Ammonium Compounds Tuned by Incorporating Hydrophilic co-Monomer

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