Evaluation of the Bactericidal and Fungicidal Activities of Poly([2-(methacryloyloxy)ethyl]trimethyl Ammonium Chloride)(Poly (METAC))-Based Materials
Abstract
:1. Introduction
2. Materials and Methods
2.1. Materials
2.2. Preparation of Poly(METAC) and Poly(METAC)-gel
2.3. Determination of Minimum Inhibitory Concentration (MIC) of Poly(METAC)
2.4. Evaluation of Bacterial Aggregation/Precipitation by Poly(METAC) and Poly(METAC)-gel
2.5. Evaluation of the Bactericidal Effect of Poly(METAC) and Poly(METAC)-gel
2.6. Characterizations
3. Results
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Santos, M.R.E.; Fonseca, A.C.; Mendonça, P.V.; Branco, R.; Serra, A.C.; Morais, P.V.; Coelho, J.F.J. Recent developments in antimicrobial polymers: A review. Materials 2016, 9, 599. [Google Scholar] [CrossRef] [PubMed]
- Jain, A.; Duvvuri, L.S.; Farah, S.; Beyth, N.; Domb, A.J.; Khan, W. Antimicrobial polymers. Adv. Heal. Mater. 2014, 3, 1969–1985. [Google Scholar] [CrossRef] [PubMed]
- Siedenbiedel, F.; Tiller, J.C. Antimicrobial polymers in solution and on surfaces: Overview and functional principles. Polymers 2012, 4, 46–71. [Google Scholar] [CrossRef]
- Liu, X.; Zhang, H.; Tian, Z.; Sen, A.; Allcock, H.R. Preparation of quaternized organic-inorganic hybrid brush polyphosphazene-co-poly[2-(dimethylamino)ethyl methacrylate]electrospun fibers and their antibacterial properties. Polym. Chem. 2012, 3, 2082–2091. [Google Scholar] [CrossRef]
- Willyard, C. Drug-resistant bacteria ranked. Nature 2017, 543, 15. [Google Scholar] [CrossRef] [PubMed]
- Klevens, R.M.; Morrison, M.A.; Nadle, J.; Petit, S.; Gershman, K.; Ray, S.; Harrison, L.H.; Lynfield, R.; Dumyati, G.; Townes, J.M.; et al. Invasive methicillin-resistant Staphylococcus aureus infections in the United States. J. Am. Med. Assoc. 2007, 298, 1763–1771. [Google Scholar] [CrossRef] [PubMed]
- Su, Y.; Tian, L.; Yu, M.; Gao, Q.; Wang, D.; Xi, Y.; Yang, P.; Lei, B.; Ma, P.X.; Li, P. Cationic peptidopolysaccharides synthesized by ‘click’ chemistry with enhanced broad-spectrum antimicrobial activities. Polym. Chem. 2017, 8, 3788–3800. [Google Scholar] [CrossRef]
- Gao, Q.; Li, P.; Zhao, H.; Chen, Y.; Jiang, L.; Ma, P.X. Methacrylate-ended polypeptides and polypeptoids for antimicrobial and antifouling coatings. Polym. Chem. 2017, 8, 6386–6397. [Google Scholar] [CrossRef]
- Allen, M.J.; White, G.F.; Morby, A.P. The response of Escherichia coli to exposure to the biocide polyhexamethylene biguanide. Microbiology 2006, 152, 989–1000. [Google Scholar] [CrossRef] [PubMed]
- Chindera, K.; Mahato, M.; Sharma, A.K.; Horsley, H.; Kloc-Muniak, K.; Kamaruzzaman, N.F.; Kumar, S.; McFarlane, A.; Stach, J.; Bentin, T.; et al. The antimicrobial polymer PHMB enters cells and selectively condenses bacterial chromosomes. Sci. Rep. 2016, 6, 23121. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Zhao, Y.; Lord, M.S.; Stenzel, M.H. A polyion complex micelle with heparin for growth factor delivery and uptake into cells. J. Mater. Chem. B 2013, 1, 1635–1643. [Google Scholar] [CrossRef]
- Hemp, S.T.; Smith, A.E.; Bunyard, W.C.; Rubinstein, M.H.; Long, T.E. RAFT polymerization of temperature- and salt-responsive block copolymers as reversible hydrogels. Polymer 2014, 55, 2325–2331. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Cao, X.; An, Z. RAFT synthesis in water of cationic polyelectrolytes with tunable UCST. Macromol. Rapid Commun. 2015, 36, 2107–2110. [Google Scholar] [CrossRef] [PubMed]
- Lutz, J.-F.; Lehn, J.-M.; Meijer, E.W.; Matyjaszewski, K. From precision polymers to complex materials and systems. Nat. Rev. Mater. 2016, 1, 16024. [Google Scholar] [CrossRef]
- Stuart, M.A.C.; Huck, W.T.S.; Genzer, J.; Müller, M.; Ober, C.; Stamm, M.; Sukhorukov, G.B.; Szleifer, I.; Tsukruk, V.V.; Urban, M.; et al. Emerging applications of stimuli-responsive polymer materials. Nat. Mater. 2010, 9, 101–113. [Google Scholar] [CrossRef] [PubMed]
- Stopiglia, C.D.O.; Collares, F.M.; Ogliari, F.A.; Piva, E.; Fortes, C.B.B.; Samuel, S.M.W.; Scroferneker, M.L. Antimicrobial activity of [2-(methacryloyloxy)ethyl]trimethylammonium chloride against Candida spp. Rev. Iberoam. Micol. 2012, 29, 20–23. [Google Scholar] [CrossRef] [PubMed]
- Prijck, K.D.; Smet, N.D.; Coenye, T.; Schacht, E.; Nelis, H.J. Prevention of Candida albicans biofilm formation by covalently bound dimethylaminoethylmethacrylate and polyethylenimine. Mycopathologia 2010, 170, 213–221. [Google Scholar] [CrossRef] [PubMed]
- Goel, N.K.; Rao, M.S.; Kumar, V.; Bhardwaj, Y.K.; Chaudhari, C.V.; Dubey, K.A.; Sabharwal, S. Synthesis of antibacterial cotton fabric by radiation-induced grafting of [2-(methacryloyloxy)ethyl]trimethylammonium chloride (MAETC) onto cotton. Radiat. Phys. Chem. 2009, 78, 399–406. [Google Scholar] [CrossRef]
- Hassan, M.M. Binding of a quaternary ammonium polymer-grafted-chitosan onto a chemically modified wool fabric surface: Assessment of mechanical, antibacterial and antifungal properties. RSC Adv. 2015, 5, 35497–35505. [Google Scholar] [CrossRef]
- Yanisch-Perron, C.; Vieira, J.; Messing, J. Improved M13 phage cloning vectors and host strains: Nucleotide sequences of the M13mp18 and pUC19 vectors. Gene 1985, 33, 103–111. [Google Scholar] [CrossRef]
- Sambrook, J.; Russell, D.W. Molecular Cloning: A Laboratory Manual, 3rd ed.; Cold Spring Harbor Laboratory Press: Huntington, NY, USA, 2001. [Google Scholar]
- Rawlinson, L.-A.B.; O’Gara, J.P.; Jones, D.S.; Brayden, D.J. Resistance of Staphylococcus aureus to the cationic antimicrobial agent poly(2-(dimethylamino ethyl)methacrylate) (pDMAEMA) is influenced by cell-surface charge and hydrophobicity. J. Med. Microbiol. 2011, 60, 968–976. [Google Scholar] [CrossRef] [PubMed]
- Shirbin, S.J.; Lam, S.J.; Chan, N.J.-A.; Ozmen, M.M.; Fu, Q.; O’Brien-Simpson, N.; Reynolds, E.C.; Qiao, G.G. Polypeptide-based macroporous cryogels with inherent antimicrobial properties: The importance of a macroporous structure. ACS Macro Lett. 2016, 5, 552–557. [Google Scholar] [CrossRef]
- Pranantyo, D.; Xu, L.Q.; Hou, Z.; Kang, E.-T.; Chan-Park, M.B. Increasing bacterial affinity and cytocompatibility with four-arm star glycopolymers and antimicrobial α-polylysine. Polym. Chem. 2017, 8, 3364–3373. [Google Scholar] [CrossRef]
- Lin, W.-C.; Liou, S.-H.; Kotsuchibashi, Y. Development and characterisation of the imiquimod poly(2-(2-methoxyethoxy)ethyl methacrylate) hydrogel dressing for keloid therapy. Polymers 2017, 9, 579. [Google Scholar] [CrossRef]
- Berlutti, F.; Rosso, F.; Bosso, P.; Giansanti, F.; Ajello, M.; Rosa, A.D.; Farina, E.; Antonini, G.; Valenti, P. Quantitative evaluation of bacteria adherent to polyelectrolyte HEMA-based hydrogels. J. Biomed. Mater. Res. A 2003, 67A, 18–25. [Google Scholar] [CrossRef] [PubMed]
- Williams, M.; Penfold, N.J.W.; Lovett, J.R.; Warren, N.J.; Douglas, C.W.I.; Doroshenko, N.; Verstraete, P.; Smets, J.; Armes, S.P. Bespoke cationic nano-objects via RAFT aqueous dispersion polymerization. Polym. Chem. 2016, 7, 3864–3873. [Google Scholar] [CrossRef]
- He, H.; Adzima, B.; Zhong, M.; Averick, S.; Koepsel, R.; Murata, H.; Russell, A.; Luebke, D.; Takahara, A.; Nulwala, H.; et al. Multifunctional photo-crosslinked polymeric ionic hydrogel films. Polym. Chem. 2014, 5, 2824–2835. [Google Scholar] [CrossRef]
- Yang, W.J.; Tao, X.; Zhao, T.; Weng, L.; Kang, E.-T.; Wang, L. Antifouling and antibacterial hydrogel coatings with self-healing properties based on a dynamic disulfide exchange reaction. Polym. Chem. 2015, 6, 7027–7035. [Google Scholar] [CrossRef]
- Banerjee, I.; Pangule, R.C.; Kane, R.S. Antifouling Coatings: Recent Developments in the Design of Surfaces That Prevent Fouling by Proteins, Bacteria, and Marine Organisms. Adv. Mater. 2011, 23, 690–718. [Google Scholar] [CrossRef] [PubMed]
- Lowe, S.; O’Brien-Simpson, N.M.; Connal, L.A. Antibiofouling polymer interfaces: Poly(ethylene glycol) and other promising candidates. Polym. Chem. 2015, 6, 198–212. [Google Scholar] [CrossRef]
MIC (μg/mL) * | |||
---|---|---|---|
in Liquid Media | on Solid Media | ||
S. aureus | MS | 123 | 370 |
MR | 123 | 370 | |
P. aeruginosa | 123 | 370 | |
E. coli | 370 | 3300 | |
B. subtilis | 123 | 370 | |
C. albicans | 370 | 1100 | |
Sa. cerevisiae | 370 | 10,000< |
© 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
Share and Cite
Shiga, T.; Mori, H.; Uemura, K.; Moriuchi, R.; Dohra, H.; Yamawaki-Ogata, A.; Narita, Y.; Saito, A.; Kotsuchibashi, Y. Evaluation of the Bactericidal and Fungicidal Activities of Poly([2-(methacryloyloxy)ethyl]trimethyl Ammonium Chloride)(Poly (METAC))-Based Materials. Polymers 2018, 10, 947. https://doi.org/10.3390/polym10090947
Shiga T, Mori H, Uemura K, Moriuchi R, Dohra H, Yamawaki-Ogata A, Narita Y, Saito A, Kotsuchibashi Y. Evaluation of the Bactericidal and Fungicidal Activities of Poly([2-(methacryloyloxy)ethyl]trimethyl Ammonium Chloride)(Poly (METAC))-Based Materials. Polymers. 2018; 10(9):947. https://doi.org/10.3390/polym10090947
Chicago/Turabian StyleShiga, Toshiki, Hiromitsu Mori, Keiichi Uemura, Ryota Moriuchi, Hideo Dohra, Aika Yamawaki-Ogata, Yuji Narita, Akihiro Saito, and Yohei Kotsuchibashi. 2018. "Evaluation of the Bactericidal and Fungicidal Activities of Poly([2-(methacryloyloxy)ethyl]trimethyl Ammonium Chloride)(Poly (METAC))-Based Materials" Polymers 10, no. 9: 947. https://doi.org/10.3390/polym10090947