Applied Microbiology and Biotechnology

, Volume 89, Issue 3, pp 475–492 | Cite as

Antimicrobial polymers: mechanism of action, factors of activity, and applications

Mini-Review

Abstract

Complex epidemiological situation, nosocomial infections, microbial contamination, and infection risks in hospital and dental equipment have led to an ever-growing need for prevention of microbial infection in these various areas. Macromolecular systems, due to their properties, allow one to efficiently use them in various fields, including the creation of polymers with the antimicrobial activity. In the past decade, the intensive development of a large class of antimicrobial macromolecular systems, polymers, and copolymers, either quaternized or functionalized with bioactive groups, has been continued, and they have been successfully used as biocides. Various permanent microbicidal surfaces with non-leaching polymer antimicrobial coatings have been designed. Along with these trends, new moderately hydrophobic polymer structures have been synthesized and studied, which contain protonated primary or secondary/tertiary amine groups that exhibited rather high antimicrobial activity, often unlike their quaternary analogues. This mini-review briefly highlights and summarizes the results of studies during the past decade and especially in recent years, which concern the mechanism of action of different antimicrobial polymers and non-leaching microbicidal surfaces, and factors influencing their activity and toxicity, as well as major applications of antimicrobial polymers.

Keywords

Bacteria Antimicrobial activity Quaternary/non-quaternary polymers Mechanism of action 

Notes

References

  1. AL-Badri ZM, Som A, Lyon S, Nelson CF, Nusslein K, Tew GN (2008) Investigating the effect of increasing charge density on the hemolytic activity of synthetic antimicrobial polymers. Biomacromolecules 9:2805–2810CrossRefGoogle Scholar
  2. Albert M, Feiertag P, Hayn G, Saf R, Hönig H (2003) Structure–activity relationships of oligoguanidines—influence of counterion, diamine, and average molecular weight on biocidal activities. Biomacromolecules 4:1811–1817CrossRefGoogle Scholar
  3. Allison BC, Applegate BM, Youngblood JP (2007) Hemocompatibility of hydrophilic antimicrobial copolymers of alkylated 4-vinylpyridine. Biomacromolecules 8:2995–2999CrossRefGoogle Scholar
  4. Afinogenov GE, Panarin EF (1993) Antimicrobial polymers. Gippokrat, St. Petersburg, p 264 (in Russian)Google Scholar
  5. Berkovich AK, Orlov VN, Melik-Nubarov NS (2009) Interaction of polyanions with electroneutral liposomes in a slightly acidic medium. Polym Sci Ser A 51:648–657CrossRefGoogle Scholar
  6. Block SS (ed) (2001) Disinfection, sterilization and preservation, 5th edn. Lippincott Williams & Wilkins, New YorkGoogle Scholar
  7. Bordenave N, Grelier S, Coma V (2010) Hydrophobization and antimicrobial activity of chitosan and paper-based packaging material. Biomacromolecules 11:88–96CrossRefGoogle Scholar
  8. Broxton P, Woodcock PM, Gilbert P (1983) A study of the antibacterial activity of some polyhexamethylene biguanides towards Escherichia coli ATCC 8739. J Appl Bacteriol 54:345–353Google Scholar
  9. Broxton P, Woodcock PM, Heatley M, Gilbert P (1984) Interaction of some polyhexamethylene biguanides and membrane phospholipids in Escherichia coli. J Appl Bacteriol 57:115–124Google Scholar
  10. Carrier D, Dufourcq J, Faucon J-F, Pezolet M (1985) A fluorescence investigation of the effects of polylysine on dipalmitoylphosphatidylglycerol bilayers. Biochim Biophys Acta 820:131–139CrossRefGoogle Scholar
  11. Chen CZ, Cooper SL (2002) Interactions between dendrimer biocides and bacterial membranes. Biomaterials 23:3359–3368CrossRefGoogle Scholar
  12. Chen Z, Sun YY (2006) N-halamine-based antimicrobial additives for polymers: preparation, characterization, and antimicrobial activity. Ind Eng Chem Res 45:2634–2640CrossRefGoogle Scholar
  13. Chen CZ, Beck-Tan NC, Dhurjati P, van Dyk TK, LaRossa RA, Cooper SL (2000) Quaternary ammonium functionalized poly(propylene imine) dendrimers as effective antimicrobials: structure–activity studies. Biomacromolecules 1:473–480CrossRefGoogle Scholar
  14. Chen Y, Worley SD, Kim J, Wie C-I C-I, Chen T-Y, Santiago JI, Williams JF, Sun G (2003) Biocidal poly(styrenehydantoin) beads for disinfection of water. Ind Eng Chem Res 42:280–284CrossRefGoogle Scholar
  15. Chen Y, Worley SD, Huang TS, Weese J, Kim J, Wei C-I, Williams JF (2004) Biocidal polystyrene beads. IV. Functionalized methylated polystyrene. J Appl Polym Sci 92:368–372CrossRefGoogle Scholar
  16. Denyer SP, Stewart GSAB (1998) Mechanisms of action of disinfectants. Intern Biodeterior Biodegrad 41:261–268CrossRefGoogle Scholar
  17. Dizman B, Elasri MO, Mathias LJ (2005) Synthesis, characterization, and antibacterial activities of novel methacrylate polymers containing norfloxacin. Biomacromolecules 6:514–520. doi:10.1021/bm049383 [PubMed: 15638560]CrossRefGoogle Scholar
  18. Ferreira L, Zumbuehl A (2009) Non-leaching surfaces capable of killing microorganisms on contact. J Mater Chem 19:7796–7806CrossRefGoogle Scholar
  19. Franklin TJ, Snow GA (1981) Antiseptics, antibiotics and the cell membrane. In: Franklin TJ, Snow GA (eds) Biochemistry of antimicrobial action, 3rd edn. Chapman & Hall, London, pp 58–78Google Scholar
  20. Franklin TJ, Snow GA (2005) Biochemistry and molecular biology of antimicrobial drug action, 6th edn. Springer, New York (chap. 2, chap 7)Google Scholar
  21. Franzin CM, Macdonald PM (2001) Polylysine-induced 2H NMR-observable domains in phosphatidylserine/phosphatidylcholine lipid bilayers. Biophys J 81:3346–3362CrossRefGoogle Scholar
  22. Gabriel GJ, Som A, Madkour AE, Eren T, Tew GN (2007) Infectious disease: connecting innate immunity to biocidal polymers. Mater Sci Eng R Rep 57(1–6):28–64CrossRefGoogle Scholar
  23. Gabriel GJ, Pool JG, Som A, Dabkowski JM, Coughlin EB, Muthukumar M, Tew GN (2008a) Interactions between antimicrobial polynorbornenes and phospholipid vesicles monitored by light scattering and microcalorimetry. Langmuir 24:12489–12495CrossRefGoogle Scholar
  24. Gabriel GJ, Madkour AE, Dabkowski JM, Nelson CF, Nüsslein K, Tew GN (2008b) Synthetic mimic of antimicrobial peptide with nonmembrane-disrupting antibacterial properties. Biomacromolecules 9:2980–2983CrossRefGoogle Scholar
  25. Gabriel GJ, Maegerlein JA, Nelson CF, Dabkowski JM, Eren T, Nüsslein K, Tew GN (2009) Comparison of facially amphiphilic versus segregated monomers in the design of antibacterial copolymers. Chem Eur J 15(2):433–439CrossRefGoogle Scholar
  26. Gelman MA, Weisblum B, Lynn DM, Gellman SH (2004) Biocidal activity of polystyrenes that are cationic by virtue of protonation. Org Lett 6(4):557–560CrossRefGoogle Scholar
  27. Gilbert P, McBain AJ (2003) An evaluation of the potential impact of the increased use of biocides within consumer products upon the prevalence of antibiotic resistance. Clinical Microbiol Rev 16:189–208CrossRefGoogle Scholar
  28. Gilbert P, Moore LE (2005) Cationic antiseptics: diversity of action under a common epithet. J Appl Microbiol 99:703–715CrossRefGoogle Scholar
  29. Grapski JA, Cooper SL (2001) Synthesis and characterization of nonleaching biocidal polyurethanes. Biomaterials 22:2239–2246CrossRefGoogle Scholar
  30. Haldar J, An D, Alvarez de Cienfuegos L, Chen J, Klibanov AM (2006) Polymeric coatings that inactivate both influenza virus and pathogenic bacteria. Proc Natl Acad Sci USA 103:17667–17671CrossRefGoogle Scholar
  31. Hetrick EM, Schoenfisch MH (2006) Reducing implant-related infections: active release strategies. Chem Soc Rev 35:780–789CrossRefGoogle Scholar
  32. Hu FX, Neoh KG, Cen L, Kang ET (2005) Antibacterial and antifungal efficacy of surface functionalized polymeric beads in repeated applications. Biotechnol Bioeng 89(4):474–484CrossRefGoogle Scholar
  33. Huang J, Murata H, Koepsel RR, Russell AJ, Matyjaszewski K (2007) Antibacterial polypropylene via surface-initiated atom transfer radical polymerization. Biomacromolecules 8:1396–1399CrossRefGoogle Scholar
  34. Huang J, Koepsel RR, Murata H, Wu W, Lee SB, Kowalewski T, Russell AJ, Matyjaszewski K (2008) Nonleaching antibacterial glass surfaces via “grafting onto”: the effect of the number of quaternary ammonium groups on biocidal activity. Langmuir 24:6785–6795CrossRefGoogle Scholar
  35. Hugo WB (1999) Disinfection mechanisms. In: Russell AD, Hugo WB, Ayliffe GAJ (eds) Principles and practice of disinfection, preservation and sterilization, 3rd edn. Blackwell Science, Oxford, pp 258–283Google Scholar
  36. Ikeda T, Tazuke S, Watanabe M (1983) Interaction of biologically active molecules with phospholipid membranes. 1. Fluorescence depolarization studies on the effect of polymeric biocide bearing biguanide groups in the main chain. Biochim Biophys Acta 735:380–386CrossRefGoogle Scholar
  37. Ikeda T, Ledwith A, Bamford CH, Hann RA (1984a) Interaction of a polymeric biguanide biocide with phospholipid membranes. Biochem Biophys Acta 769:57–66CrossRefGoogle Scholar
  38. Ikeda T, Yamaguchi H, Tazuke S (1984b) New polymeric biocides: synthesis and antibacterial activities of polycations with pendant biguanide groups. Antimicrob Agents Chemother 26(2):139–144Google Scholar
  39. Ikeda T, Tazuke S, Suzuki Y (1984c) Biologically active polycations: synthesis and antimicrobial activity of poly(trialkylvinylbenzyl ammonium chloride)s. Makromol Chem 185:869–876CrossRefGoogle Scholar
  40. Ikeda T, Hirayama H, Yamaguchi H, Tazuke S, Watanabe M (1986) Polycationic biocides with pendant active groups: molecular weight dependence of antibacterial activity. Antimicrob Agents Chemother 30:132–136Google Scholar
  41. Ikeda T, Yamaguchi H, Tazuke S (1990) Phase separation in phospholipid bilayers induced by biologically active polycations. Biochem Biophys Acta 1026(1):105–112CrossRefGoogle Scholar
  42. Ilker MF, Nusslein K, Tew GN, Coughlin EB (2004) Tuning the hemolytic and antibacterial activities of amphiphilic polynorbornene derivatives. J Am Chem Soc 126:15870–15875CrossRefGoogle Scholar
  43. Kenawy ER, Mahmoud YAG (2003) Biologically active polymers, 6: synthesis and antimicrobial activity of some linear copolymers with quaternary ammonium and phosphonium groups. Macromol Biosci 3(2):107–116CrossRefGoogle Scholar
  44. Kenawy ER, Abdel-Hay FI, El-Shanshoury A, El-Newehy MH (2002) Biologically active polymers. V. Synthesis and antimicrobial activity of modified poly(glycidylmethacrylate-co-2-hydroxyethyl methacrylate) derivatives with quaternary ammonium and phosphonium salts. J Polym Sci A: Polym Chem 40:2384–2393CrossRefGoogle Scholar
  45. Kenawy E-R, Abdel-Hay FI, El-Magd AA, Mahmoud Y (2006) Synthesis and antimicrobial activity of some polymers derived from modified amino polyacrylamide by reacting it with benzoate esters and benzaldehyde derivatives. J Appl Polym Sci 99:2428–2437CrossRefGoogle Scholar
  46. Kenawy E-R, Worley SD, Broughton R (2007) The chemistry and applications of antimicrobial polymers: a state-of-the-art review. Biomacromolecules 8(5):1359–1384CrossRefGoogle Scholar
  47. Klibanov AM (2007) Permanently microbicidal materials coatings. J Mater Chem 17:2479–2482CrossRefGoogle Scholar
  48. Kocer HB, Akdag A, Ren X, Broughton RM, Worley SD, Huang TS (2008) Effect of alkyl derivatization on several properties of N-halamine antimicrobial siloxane coatings. Ind Eng Chem Res 47:7558–7563CrossRefGoogle Scholar
  49. Kou L, Liang J, Ren X, Kocer HB, Worley SD, Tzou YM, Huang TS (2009) Synthesis of a water-soluble siloxane copolymer and its application for antimicrobial coatings. Ind Eng Chem Res 48:6521–6526CrossRefGoogle Scholar
  50. Larkin DFP, Kilvington S, Dart JKG (1992) Treatment of Acanthamoeba keratitis with polyhexamethylene biguanide. Ophthalmology 99:185–191Google Scholar
  51. Lauzardo M, Rubin J (2001) Mycobacterial disinfection. In: Block SS (ed) Disinfection, sterilization and preservation, 5th edn. Lippincott Williams &Wilkins, New York, pp 513–528 (chap. 26)Google Scholar
  52. Lee SB, Russell AJ, Matyjaszewski K (2003) ATRP synthesis of amphiphilic random, gradient, and block copolymers of 2-(dimethylamino)ethyl methacrylate and n-butyl methacrylate in aqueous media. Biomacromolecules 4(5):1386–1393CrossRefGoogle Scholar
  53. Lee SB, Koepsel RR, Morley SW, Matyjaszewski K, Sun Y, Russell AJ (2004) Permanent, nonleaching antibacterial surfaces. 1. Synthesis by atom transfer radical polymerization. Biomacromol 5(3):877–882CrossRefGoogle Scholar
  54. Lewis K, Klibanov AM (2005) Surpassing nature: rational design of sterile-surface materials. Trends Biotechnol 23(7):343–348CrossRefGoogle Scholar
  55. Liang J, Chen Y, Barnes K, Wu R, Worley SD, Huang TS (2006) N-halamine/quat siloxane copolymers for use in biocidal coatings. Biomaterials 27:2495–2501CrossRefGoogle Scholar
  56. Liang J, Barnes K, Akdag A, Worley SD, Lee J, Broughton RM, Huang TS (2007) Improved antimicrobial siloxane. Ind Eng Chem Res 46(7):1861–1866CrossRefGoogle Scholar
  57. Lienkamp K, Madkour AE, Musante A, Nelson CF, Nüsslein K, Tew GN (2008) Antimicrobial polymers prepared by ROMP with unprecedented selectivity: a molecular construction kit approach. J Am Chem Soc 130:9836–9843CrossRefGoogle Scholar
  58. Lienkamp K, Madkour AE, Kumar K-N, Nüsslein K, Tew GN (2009) Antimicrobial polymers prepared by ring-opening metathesis polymerization: manipulating antimicrobial properties by organic counterion and charge density variation. Chem Eur J 15:11715–11722CrossRefGoogle Scholar
  59. Lin J, Qiu S, Lewis K, Klibanov AM (2002) Bactericidal properties of flat surfaces and nanoparticles derivatized with alkylated polyethylenimines. Biotechnol Prog 18(5):1082–1086CrossRefGoogle Scholar
  60. Lin J, Qiu S, Lewis K, Klibanov AM (2003) Mechanism of bactericidal and fungicidal activities of textiles covalently modified with alkylated polyethylenimine. Biotechnol Bioeng 83:168–172CrossRefGoogle Scholar
  61. Maillard J-Y (2002) Bacterial target sites for biocide action. J Appl Microbiol Symp Suppl 92:16S–27SGoogle Scholar
  62. Makal U, Wood L, Ohman DE, Wynne KJ (2006) Polyurethane biocidal polymeric surface modifiers. Biomaterials 27:1316–1326CrossRefGoogle Scholar
  63. Matias VRF, Beveridge TJ (2005) Cryo-electron microscopy reveals native polymeric cell wall structure in Bacillus subtilis 168 and the existence of a periplasmic space. Mol Microbiol 56:240–251CrossRefGoogle Scholar
  64. Matias VRF, Al-Amoudi A, Dubochet J, Beveridge TJ (2003) Cryo-transmission electron microscopy of frozen-hydrated sections of Escherichia coli and Pseudomonas aeruginosa. J Bacteriol 185:612–6118CrossRefGoogle Scholar
  65. Merianos JJ (2001) Surface-active agents. In: Block SS (ed) Disinfection, sterilization and preservation, 5th edn. Lippincott Williams & Wilkins, New York, pp 283–320Google Scholar
  66. McDonnel G, Russell AD (1999) Antiseptics and disinfectants: activity, action, and resistance. Clin Microbiol Rev 12(1):147–179Google Scholar
  67. Milovic NM, Wang J, Lewis K, Klibanov AM (2005) Immobilized N-alkylated polyethylenimine avidly kills bacteria by rupturing cell membranes with no resistance developed. Biotechnol Bioeng 90:715–722CrossRefGoogle Scholar
  68. Murata H, Koepsel RR, Matyjaszewski K, Russell AJ (2007) Permanent, non-leaching antibacterial surfaces 2: how high density cationic surfaces kill bacterial cells. Biomaterials 28:4870–4879CrossRefGoogle Scholar
  69. Nonaka T, Uemura Y, Ohse K, Jyono K, Kurihara S (1997) Preparation of resins containing phenol derivatives from chloromethylstyrene–tetraethyleneglycol dimethacrylate copolymer beads and antibacterial activity of resins. J Appl Polym Sci 66:1621–1630CrossRefGoogle Scholar
  70. Oku N, Yamaguchi N, Shibamoto S, Ito F, Nango M (1986) The fusogenic effect of synthetic polycations on negatively charged lipid bilayers. J Biochem 100:935–944Google Scholar
  71. Palermo E, Kuroda K (2009) Chemical structure of cationic groups in amphiphilic polymethacrylates modulates the antimicrobial and hemolytic activities. Biomacromolecules 10:1416–1428CrossRefGoogle Scholar
  72. Palermo E, Sovadinova I, Kuroda K (2009) Structural determinants of antimicrobial activity and biocompatibility in membrane-disrupting methacrylamide random copolymers. Biomacromolecules 10:3098–3107CrossRefGoogle Scholar
  73. Panarin EF, Kopeikin MM (2002) Biological activity of synthetic polyelectrolyte complexes of ionogenic surfactants. Polym Sci 44:2340–2351Google Scholar
  74. Panarin EF, Solovskii MV, Zaikina NA, Afinogenov GE (1985) Biological activity of cationic polyelectrolytes. Macromol Chem Suppl 9:25–33CrossRefGoogle Scholar
  75. Park D, Wang J, Klibanov AM (2006) One-step, painting-like coating procedures to make surfaces highly and permanently bactericidal. Biotechnol Prog 22:584–589CrossRefGoogle Scholar
  76. Rawlinson L-AB, Ryan SM, Mantovani G, Syrett JA, Haddleton DM, Brayden DJ (2010) Antibacterial effects of poly(2-(dimethylamino ethyl)methacrylate) against selected Gram-positive and Gram-negative bacteria. Biomacromolecules 11:443–453CrossRefGoogle Scholar
  77. Ren X, Kou L, Liang J, Worley SD, Tzou Y-M, Huang TS (2008) Antimicrobial efficacy and light stability of N-halamine siloxanes bound to cotton. Cellulose 15:593–598Google Scholar
  78. Russel AD (2001) Principles of antimicrobial activity and resistance. Part II: fundamental principles of activity. In: Block SS (ed) Disinfection, sterilization and preservation, 5th edn. Lippincott Williams & Wilkins, New York, pp 31–56Google Scholar
  79. Russell AD (2002) Introduction of biocides into clinical practice and the impact on antibiotic-resistant bacteria. J Appl Microbiol Symp Suppl 92:121S–135SGoogle Scholar
  80. Russell AD (2003) Biocide use and antibiotic resistance: the relevance of laboratory findings to clinical and environmental situations. Lancet Infect Dis 3:794–803CrossRefGoogle Scholar
  81. Sambhy V, Peterson BR, Sen A (2008) Antibacterial and hemolytic activities of pyridinium polymers as a function of the spatial relationship between the positive charge and the pendant alkyl tail. Angew Chem Int Ed 47(7):1250–1254CrossRefGoogle Scholar
  82. Sellenet PH, Allison B, Applegate BM, Youngblood JP (2007) Synergistic activity of hydrophilic modification in antibiotic polymers. Biomacromolecules 8:19–23CrossRefGoogle Scholar
  83. Singer SJ, Nicholson GL (1972) The fluid mosaic model of the structure of cell membranes. Science 175:720–731CrossRefGoogle Scholar
  84. Shirai A, Sumitomo T, Yoshida M, Kaimura T, Nagamune H, Maeda T, Kourai H (2006) Synthesis and biological properties of Gemini quaternary ammonium compounds, 5, 5′-[2, 2′-(ω-polymethylenedicarbonyldioxy)diethyl]bis-(3-alkyl-4-methylthiazolium iodide) and its brominated analog. Chem Pharm Bull 54:639–645CrossRefGoogle Scholar
  85. Sun Y, Sun G (2001a) Novel regenerable N-halamine polymeric biocides. I. Synthesis, characterization, and antibacterial activity of hydantoin-containing polymers. J Appl Polym Sci 80:2460–2467CrossRefGoogle Scholar
  86. Sun Y, Sun G (2001b) Novel regenerable N-halamine polymeric biocides. III. Grafting hydantoin-containing monomers onto synthetic fabrics. J Appl Polym Sci 81:1517–1525CrossRefGoogle Scholar
  87. Sun Y, Sun G (2001c) Durable and refreshable polymeric N-halamine biocides containing 3-(4′-vinylbenzyl)-5, 5-dimethylhydantoin. J Polym Sci Part A Polym Chem 39:3348–3355CrossRefGoogle Scholar
  88. Sun Y, Sun G (2002a) Synthesis, characterization, and antibacterial activities of novel N-halamine polymer beads prepared by suspension copolymerization. Macromolecules 35:8909–8912CrossRefGoogle Scholar
  89. Sun Y, Sun G (2002b) Durable and regenerable antimicrobial textile materials prepared by a continuous grafting process. J Appl Polym Sci 84:1592–1599CrossRefGoogle Scholar
  90. Sun Y, Chen T-Y, Worley SD, Sun G (2001) Novel refreshable N-halamine polymeric biocides containing imidazolidin-4-one derivatives. J Polym Sci Part A: Polym Chem 39:3073–3084CrossRefGoogle Scholar
  91. Tashiro T (2001) Antibacterial and bacterium adsorbing macromolecules. Macromol Mater Eng 286(2):63–87CrossRefGoogle Scholar
  92. Tew GN, Liu DH, Chen B, Doerksen RJ, Kaplan J, Carroll PJ, Klein ML, DeGrado WF (2002) Supramolecular chemistry and self-assembly special feature: de novo design of biomimetic antimicrobial polymers. Proc Natl Acad Sci USA 99:5110–5114CrossRefGoogle Scholar
  93. Tew GN, Scott RW, Klein ML, DeGrado WF (2010) De novo design of antimicrobial foldamers and small molecules: from discovery to practical application. Acc Chem Res 43:30–39CrossRefGoogle Scholar
  94. Thome J, Hollander A, Jaeger W, Trickand I, Oehr C (2003) Ultrathin antibacterial polyammonium coatings on polymer surfaces. Surf Coat Technol 174–175:584–587CrossRefGoogle Scholar
  95. Tiller JC, Liao CJ, Lewis K, Klibanov AM (2001) Designing surfaces that kill bacteria on contact. Proc Natl Acad Sci USA 98:5981–5985CrossRefGoogle Scholar
  96. Tiller JC, Lee SB, Lewis K, Klibanov AM (2002) Polymer surfaces derivatized with poly(vinyl-N-hexylpyridinium) kill airborne and waterborne bacteria. Biotechnol Bioeng 79(4):465–471CrossRefGoogle Scholar
  97. Timofeeva LM, Vasilieva YA, Kleshcheva NA, Gromova GL, Topchiev DA (2002a) Radical polymerization of diallylamine compounds: from quantum chemical modeling to controllable synthesis of high-molecular weight polymers. Int J Quantum Chem 88:531–541CrossRefGoogle Scholar
  98. Timofeeva LM, Vasilieva YA, Kleshcheva NA, Gromova GL, Timofeeva GI, Rebrov AI, Topchiev DA (2002b) Synthesis of high-molecular weight polymers based on N, N-diallyl-N-methylamine. Macromol Chem Phys 203:2296–2304CrossRefGoogle Scholar
  99. Timofeeva LM, Kleshcheva NA, Vasilieva YA, Gromova GL, Timofeeva GI, Filatova MP (2005) Synthesis of novel polymers based on monomers of the diallylamine series: mechanistic and kinetic study. Polym Sci Ser A 47:273–282Google Scholar
  100. Timofeeva LM, Kleshcheva NA, Moroz AF, Didenko LV (2009) Secondary and tertiary polydiallylammonium salts: novel polymers with high antimicrobial activity. Biomacromolecules 10:2976–2986CrossRefGoogle Scholar
  101. van der Mei HC, Rustema-Abbing M, Langworthy DE, Collias DI, Mitchell MD, Bjorkquist DW, Busscher HJ (2008) Adhesion and viability of waterborne pathogens on p-DADMAC coatings. Biotechnol Bioeng 99(1):165–169CrossRefGoogle Scholar
  102. Vointseva II, Gembitsky PA (2009) Polyguanidines—disinfecting agents and multifunctional additives to composite materials. LKM, Moscow, p 300 (in Russian)Google Scholar
  103. Waschinski CJ, Tiller JC (2005) Poly(oxazoline)s with telechelic antimicrobial functions. Biomacromolecules 6(1):235–243CrossRefGoogle Scholar
  104. Waschinski CJ, Herdes V, Schueler F, Tiller JC (2005) Influence of satellite groups on telechelic antimicrobial functions of polyoxazolines. Macromol Biosci 5:149–156CrossRefGoogle Scholar
  105. Waschinski CJ, Zimmermann J, Salz U, Hutzler R, Sadowski G, Tiller JC (2008a) Design of contact-active antimicrobial acrylate-based materials using biocidal macromers. Adv Mater 20:104–108CrossRefGoogle Scholar
  106. Waschinski CJ, Barnert S, Theobald A, Schubert R, Kleinschmidt F, Hoffmann A, Saalwächter K, Tiller JC (2008b) Insights in the antibacterial action of poly(methyloxazoline)s with a biocidal end group and varying satellite groups. Biomacromolecules 9:1764–1771CrossRefGoogle Scholar
  107. Worley SD, Sun G (1996) Biocidal polymers. Trends Polym Sci 4:364–370Google Scholar
  108. Worley SD, Chen Y, Wang JW, Wu R, Cho U, Broughton RM, Kim J, Wei CI, Williams JF, Chen J, Li Y (2005) Novel N-halamine siloxane monomers and polymers for preparing biocidal coatings. Surf Coat Int Part B: Coat Trans 88:93–100CrossRefGoogle Scholar
  109. Woo GLY, Yang ML, Yin HQ, Jaffer F, Mittelman MW, Santerre JP (2002) Biological characterization of a novel biodegradable antimicrobial polymer synthesized with fluoroquinolones. J Biomed Mater Res 59:35–45CrossRefGoogle Scholar
  110. Yaroslavov AA, Efimova AA, Lobyshev VI, Kabanov VA (2002) Reversibility of structural rearrangements in the negative vesicular membrane upon electrostatic adsorption/desorption of the polycation. Biochim Biophys Acta 1560:14–24CrossRefGoogle Scholar
  111. Yaroslavov AA, Melik-Nubarov NS, Menger FM (2006) Polymer-induced flip-flop in biomembranes. Acc Chem Res 39:702–710CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2010

Authors and Affiliations

  1. 1.A.V.Topchiev Institute of Petrochemical SynthesisRussian Academy of SciencesMoscowRussia

Personalised recommendations