Suppressing Antibacterial Resistance: Chemical Binding of Monolayer Quaternary Ammonium Salts to Polymethyl Methacrylate in an Aqueous Solution and Its Clinical Efficacy
Abstract
:1. Introduction
2. Results
2.1. QAS Binding to PMMA
2.2. Antibacterial Tests
2.3. Viability Tests
2.4. Clinical Trials
3. Discussion
4. Materials and Methods
4.1. Preparation of PMMA Discs
4.2. Binding of QAS to PMMA
4.3. Analysis of QAS Released from QAS-c-PMMA into the Solution
4.4. FTIR Difference Spectroscopy
4.5. Antibacterial Test
4.6. Cell Viability Assay
4.7. Clinical Trial
5. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
- Brown, E.D.; Wright, G.D. Antibacterial drug discovery in the resistance era. Nature 2016, 529, 336–343. [Google Scholar] [CrossRef] [PubMed]
- Hasan, I.; Qais, F.A.; Husain, F.M.; Khan, R.A.; Alsalme, A.; Alenazi, B.; Usman, M.; Jaafar, M.H.; Ahmad, I. Eco-friendly green synthesis of dextrin based poly (methyl methacrylate) grafted silver nanocomposites and their antibacterial and antibiofilm efficacy against multi-drug resistance pathogens. J. Clean. Prod. 2019, 230, 1148–1155. [Google Scholar] [CrossRef]
- El Halfawy, N.M.; el-Naggar, M.Y.; Andrews, S.C. Draft genome sequence of an Enterococcus faecalis strain (24FS) that was isolated from healthy infant feces and exhibits high antibacterial activity, multiple-antibiotic resistance, and multiple virulence factors. Microbiol. Resour. Announc. 2019, 8, e00047–e00119. [Google Scholar] [CrossRef] [PubMed]
- World Health Organization: Geneva. Ten threats to global health in 2019. Available online: https://www.who.int/emergencies/ten-threats-to-global-health-in-2019 (accessed on 16 August 2019).
- Jee, Y.; Carlson, J.; Rafai, E.; Musonda, K.; Huong, T.T.G.; Daza, P.; Sattayawuthipong, W.; Yoon, T. Antimicrobial resistance: A threat to global health. Lancet Infect. Dis. 2018, 18, 939–940. [Google Scholar] [CrossRef]
- O’Neill, J.; Review on antimicrobial resistance. Antimicrobial Resistance: Tackling a Crisis for the Health and Wealth of Nations; Wellcome Trust: London, UK, 2014; Available online: https://dlcs.io/file/wellcome/1/673e471a-bbc1-4a8f-9045-f6085272fa44#_ga=2.87349208.1376362673.1566017109-1709923019.1566017109 (accessed on 16 August 2019).
- Ventola, C.L. The antibiotic resistance crisis Part 1: Causes and threats. Pharm. Therap. 2015, 40, 277–283. [Google Scholar]
- Eze, E.C.; Chenia, H.Y.; el Zowalaty, M.E. Acinetobacter baumannii biofilms: Effects of physicochemical factors, virulence, antibiotic resistance determinants, gene regulation, and future antimicrobial treatments. Infect. Drug Resist. 2018, 11, 2277–2299. [Google Scholar] [CrossRef] [PubMed]
- Szczuka, E.; Jablonska, L.; Kaznowski, A. Coagulase-negative staphylococci: Pathogenesis, occurrence of antibiotic resistance genes and in vitro effects of antimicrobial agents on biofilm-growing bacteria. J. Med. Microbiol. 2016, 65, 1405–1413. [Google Scholar] [CrossRef]
- Domitrovic, T.N.; Hujer, A.M.; Perez, F.; Marshall, S.H.; Hujer, K.M.; Woc-Colburn, L.E.; Parta, M.; Bonomo, R.A. Multidrug resistant pseudomonas aeruginosa causing prosthetic valve endocarditis: A genetic-based chronicle of evolving antibiotic resistance. Open Forum Infect. Dis. 2016, 3, ofw188. [Google Scholar] [CrossRef]
- Volejnikova, A.; Melichercik, P.; Nesuta, O.; Vankova, E.; Bednarova, L.; Rybacek, J.; Cerovsky, V. Antimicrobial peptides prevent bacterial biofilm formation on the surface of polymethylmethacrylate bone cement. J. Med. Microbiol. 2019, 68, 961–972. [Google Scholar] [CrossRef]
- Silva, T.; Silva, J.C.; Colaco, B.; Gama, A.; Duarte-Araujo, M.; Fernandes, M.H.; Bettencourt, A.; Gomes, P. In vivo tissue response and antibacterial efficacy of minocycline delivery system based on polymethylmethacrylate bone cement. J. Biomater. Appl. 2018, 33, 380–391. [Google Scholar] [CrossRef]
- Renaud, A.; Lavigne, M.; Vendittoli, P.A. Periprosthetic joint infections at a teaching hospital in 1990-2007. Can. J. Surg. 2012, 55, 394–400. [Google Scholar] [CrossRef] [PubMed]
- Moreira-Gonzalez, A.; Jackson, I.T.; Miyawaki, T.; Barakat, K.; DiNick, V. Clinical outcome in cranioplasty: Critical review in long-term follow-up. J. Craniofac. Surg. 2003, 14, 144–153. [Google Scholar] [CrossRef] [PubMed]
- Alrahlah, A.; Fouad, H.; Hashem, M.; Niazy, A.A.; AlBadah, A. Titanium oxide (TiO2)/polymethylmethacrylate (PMMA) denture base nanocomposites: Mechanical, viscoelastic and antibacterial behavior. Materials 2018, 11, 1096. [Google Scholar] [CrossRef] [PubMed]
- Cantarella, M.; Sanz, R.; Buccheri, M.A.; Ruffino, F.; Rappazzo, G.; Scalese, S.; Impellizzeri, G.; Romano, L.; Privitera, V. Immobilization of nanomaterials in PMMA composites for photocatalytic removal of dyes, phenols and bacteria from water. J. Photochem. PhotoBiol. A-Chem. 2016, 321, 1–11. [Google Scholar] [CrossRef]
- Moreno, I.; Navascues, N.; Irusta, S.; Santamaria, J. Modulation of bactericidal action in polymer nanocomposites: Light-tuned Ag+ release from electrospun PMMA fibers. RSC Adv. 2016, 6, 78036–78042. [Google Scholar] [CrossRef]
- Gao, L.; Xie, X.; Wang, B.; Weir, M.D.; Oates, T.W.; Xu, H.H.K.; Zhang, N.; Bai, Y. Protein-repellent and antibacterial effects of a novel polymethyl methacrylate resin. J. Dent. 2018, 79, 39–45. [Google Scholar]
- Sawant, S.N.; Selvaraj, V.; Prabhawathi, V.; Doble, M. Antibiofilm properties of silver and gold incorporated PU, PCLm, PC and PMMA nanocomposites under two shear conditions. PLoS ONE 2013, 8, e63311. [Google Scholar] [CrossRef] [PubMed]
- Napari, M.; Malm, J.; Lehto, R.; Julin, J.; Arstila, K.; Sajavaara, T.; Lahtinen, M. Nucleation and growth of ZnO on PMMA by low-temperature atomic layer deposition. J. Vac. Sci. Technol. A 2015, 33, 01A128. [Google Scholar] [CrossRef] [Green Version]
- Suteewong, T.; Wongpreecha, J.; Polpanich, D.; Jangpatarapongsa, K.; Kaewsaneha, C.; Tangboriboonrat, P. PMMA particles coated with chitosan-silver nanoparticles as a dual antibacterial modifier for natural rubber latex films. Colloid. Surf. B: Biointerf. 2019, 174, 544–552. [Google Scholar] [CrossRef]
- Wang, Y.; Wang, Y.; Li, X.; Li, J.; Su, L.; Zhang, X.; Du, X. Dendritic silica particles with well-dispersed Ag nanoparticles for robust antireflective and antibacterial nanocoatings on polymeric glass. Acs Sustain. Chem. Eng. 2018, 6, 14071–14081. [Google Scholar] [CrossRef]
- Czuba, U.; Quintana, R.; Lassaux, P.; Bombera, R.; Ceccone, G.; Bañuls-Ciscar, J.; Moreno-Couranjou, M.; Detrembleur, C.; Choquet, P. Anti-biofouling activity of Ranaspumin-2 bio-surfactant immobilized on catechol-functional PMMA thin layers prepared by atmospheric plasma deposition. Colloid. Surf. B: Biointerf. 2019, 178, 120–128. [Google Scholar] [CrossRef] [PubMed]
- Su, W.; Wang, S.C.; Wang, X.X.; Fu, X.Z.; Weng, J.N. Plasma pre-treatment and TiO2 coating of PMMA for the improvement of antibacterial properties. Surf. Coat. Technol. 2010, 205, 465–469. [Google Scholar] [CrossRef]
- Jennings, M.C.; Minbiole, K.P.C.; Wuest, W.M. Quaternary ammonium compounds: An antimicrobial mainstay and platform for innovation to address bacterial resistance. Acs Infect. Dis. 2015, 1, 288–303. [Google Scholar] [CrossRef] [PubMed]
- Nuñez, L.; Moretton, J. Disinfectant-resistant bacteria in Buenos Aires city hospital wastewater. Braz. J. Microbiol. 2007, 38, 644–648. [Google Scholar] [CrossRef] [Green Version]
- Zhang, X.; Wang, L.; Levanen, E. Superhydrophobic surfaces for the reduction of bacterial adhesion. RSC Adv. 2013, 3, 12003–12020. [Google Scholar] [CrossRef]
- Russell, A.D. Bacterial resistance to disinfectants: Present knowledge and future problems. J. Hosp. Infect. 1999, 43, S57–S68. [Google Scholar] [CrossRef]
- Reidy, B.; Haase, A.; Luch, A.; Dawson, K.A. Mechanisms of silver nanoparticle release, transformation and toxicity: A critical review of current knowledge and recommendations for future studies and applications. Materials 2013, 6, 2295–2350. [Google Scholar] [CrossRef]
- Soprey, P.R.; Maxcy, R.B. Tolerance of bacteria for quaternary ammonium compounds. J. Food Sci. 1968, 33, 536–540. [Google Scholar] [CrossRef]
- Maxcy, R.B.; Tiwari, N.P.; Soprey, P.R. Changes in Escherichia coli associated with acquired tolerance for quaternary ammonium compounds. Appl. Microbiol. 1971, 22, 229–232. [Google Scholar]
- Gillespie, M.T.; May, J.W.; Skurray, R.A. Plasmid-encoded resistance to acriflavine and quaternary ammonium compounds in methicillin-resistant Staphylococcus aureus. FEMS Microbiol. Lett. 1986, 34, 47–51. [Google Scholar] [CrossRef]
- Laxminarayan, R. Antibiotic effectiveness: Balancing conservation against innovation. Science 2014, 345, 1299–1301. [Google Scholar] [CrossRef] [PubMed] [Green Version]
- Campoccia, D.; Montanaro, L.; Speziale, P.; Arciola, C.R. Antibiotic-loaded biomaterials and the risks for the spread of antibiotic resistance following their prophylactic and therapeutic clinical use. Biomaterials 2010, 31, 6363–6377. [Google Scholar] [CrossRef] [PubMed]
- Makvandi, P.; Jamaledin, R.; Jabbari, M.; Nikfarjam, N.; Borzacchiello, A. Antibacterial quaternary ammonium compounds in dental materials: A systematic review. Dent. Mater. 2018, 34, 851–867. [Google Scholar] [CrossRef] [PubMed]
- Xue, Y.; Ye, Y.S.; Chen, F.Y.; Wang, H.; Chen, C.; Xue, Z.G.; Zhou, X.P.; Xie, X.L.; Mai, Y.W. A simple and controllable graphene-templated approach to synthesise 2D silica-based nanomaterials using water-in-oil microemulsions. Chem. Commun. 2016, 52, 575–578. [Google Scholar] [CrossRef] [PubMed]
- Lenza, R.F.S.; Nunes, E.H.M.; Vasconcelos, D.C.L.; Vasconcelos, W.L. Preparation of sol–gel silica samples modified with drying control chemical additives. J. Non-Cryst. Solids 2015, 423–424, 35–40. [Google Scholar] [CrossRef]
- Pruthtikul, R.; Liewchirakorn, P. Correlation between siloxane bond formation and oxygen transmission rate in TEOS xerogel. J. Metals Mater. Miner. 2008, 18, 63–66. [Google Scholar]
- Carraro, C.; Yauw, O.W.; Sung, M.M.; Maboudian, R. Observation of three growth mechanisms in self-assembled monolayers. J. Phys. Chem. B 1998, 102, 4441–4445. [Google Scholar] [CrossRef]
- Coates, J. Interpretation of Infrared Spectra, A Practical Approach. In Encyclopedia of Analytical Chemistry; Meyers, R.A., Ed.; John Wiley & Sons Ltd.: Chichester, UK, 2000; pp. 10815–10837. [Google Scholar]
- Cacciotti, I.; Nanni, F.; Campaniello, V.; Lamastra, F.R. Development of a transparent hydrorepellent modified SiO2 coatings for glazed sanitarywares. Mater. Chem. Phys. 2014, 146, 240–252. [Google Scholar] [CrossRef]
- Cypryk, M.; Apeloig, Y. Mechanism of the Acid-Catalyzed Si−O Bond Cleavage in Siloxanes and Siloxanols. A Theoretical Study. Organometallics 2002, 21, 2165–2175. [Google Scholar] [CrossRef]
- Nakanishi, T.; Komiyama, J.; Iijima, T. Salt permeation through cationic membranes with quaternary ammonium groups of different alkylchain lengths. J. Membr. Sci. 1986, 26, 263–275. [Google Scholar] [CrossRef]
- Damour, O.; Hua, S.Z.; Lasne, F.; Villain, M.; Rousselle, P.; Collombel, C. Cytotoxicity evaluation of antiseptics and antibiotics on cultured human fibroblasts and keratinocytes. Bums 1992, 18, 479–485. [Google Scholar] [CrossRef]
- Bryers, J.D. Medical biofilms. Biotechnol. Bioeng. 2008, 100, 1–18. [Google Scholar] [CrossRef] [PubMed]
- Rolland, S.L.; McCabe, J.F.; Robinson, C.; Walls, A.W. In vitro biofilm formation on the surface of resin-based dentine adhesives. Eur. J. Oral Sci. 2006, 114, 243–249. [Google Scholar] [CrossRef] [PubMed]
- Liu, S.; Zhao, J.W.; Ruan, H.J.; Wang, W.; Wu, T.Y.; Cui, W.G.; Fan, C.Y. Antibacterial and anti-adhesion effects of the silver nanoparticles-loaded poly (L-Lactide) fibrous membrane. Mater. Sci. Eng. C 2013, 33, 1176–1182. [Google Scholar] [CrossRef] [PubMed]
- Minemawari, H.; Tanaka, M.; Tsuzuki, S.; Inoue, S.; Yamada, T.; Kumai, R.; Shimoi, Y.; Hasegaw, T. Enhanced layered-herringbone packing due to long alkyl chain substitution in solution-processable organic semiconductors. Chem. Mater. 2017, 29, 1245–1254. [Google Scholar] [CrossRef]
- Osawa, W. Surface-enhanced infrared absorption. In Near-Field Optics and Surface Plasmon Polaritons; Kawata, S., Ed.; Springer: New York, NY, USA, 2001; pp. 163–187. [Google Scholar]
- Aswal, D.K.; Lenfant, S.; Guerin, D.; Yakhmi, J.V.; Vuillaume, D. Self assembled monolayers on silicon for molecular electronics. Anal. Chim. Acta 2006, 568, 84–108. [Google Scholar] [CrossRef]
- Dietrich, H.; Schmaltz, T.; Halik, M.; Zahn, D. Molecular dynamics simulations of phosphonic acid–aluminum oxide self-organization and their evolution into ordered monolayers. Phys. Chem. Chem. Phys. 2017, 19, 5137–5144. [Google Scholar] [CrossRef]
- Zhou, Y.; Liu, P.; Gan, Y.T.; Sandoval, W.; Katakam, A.K.; Reichelt, M.; Rangell, L.; Reilly, D. Enhancing full-length antibody production by signal peptide engineering. Microb. Cell Fact. 2016, 15, 47. [Google Scholar] [CrossRef]
- Von Heijne, G. Net N-C Charge imbalance may be important for signal sequence function in bacteria. J. Mol. Biol. 1986, 20, 287–290. [Google Scholar] [CrossRef]
- Kreutzenbeck, P.; Kroger, C.; Lausberg, F.; Blaudeck, N.; Sprenger, G.A.; Freudl, F. Escherichia coli twin arginine (Tat) mutant translocases possessing relaxed signal peptide recognition specificities. J. Biol. Chem. 2007, 282, 7903–7911. [Google Scholar] [CrossRef] [PubMed]
- Gong, S.Q.; Epasinghe, D.J.; Zhou, B.; Niu, L.N.; Kimmerling, K.A.; Rueggeberg, F.A.; Yiu, C.K.Y.; Mao, J.; Pashley, D.H.; Tay, F.R. Effect of water-aging on the antimicrobial activities of an ORMOSIL-containing orthodontic acrylic resin. Acta Biomater. 2013, 9, 6964–6973. [Google Scholar] [CrossRef] [PubMed] [Green Version]
Analytes | MRM Transition m/z (Q1→Q3) | Q1 (V) | CE (V) | Q3 (V) | Retention Time |
---|---|---|---|---|---|
QAS | 460.3→121.05 | −20 | −36 | −20 | 4 |
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Lee, C.-Y.; Chen, Y.-T.; Lee, B.-S.; Chang, C.-C. Suppressing Antibacterial Resistance: Chemical Binding of Monolayer Quaternary Ammonium Salts to Polymethyl Methacrylate in an Aqueous Solution and Its Clinical Efficacy. Int. J. Mol. Sci. 2019, 20, 4668. https://doi.org/10.3390/ijms20194668
Lee C-Y, Chen Y-T, Lee B-S, Chang C-C. Suppressing Antibacterial Resistance: Chemical Binding of Monolayer Quaternary Ammonium Salts to Polymethyl Methacrylate in an Aqueous Solution and Its Clinical Efficacy. International Journal of Molecular Sciences. 2019; 20(19):4668. https://doi.org/10.3390/ijms20194668
Chicago/Turabian StyleLee, Chung-Yuan, Yi-Ting Chen, Bor-Shiunn Lee, and Che-Chen Chang. 2019. "Suppressing Antibacterial Resistance: Chemical Binding of Monolayer Quaternary Ammonium Salts to Polymethyl Methacrylate in an Aqueous Solution and Its Clinical Efficacy" International Journal of Molecular Sciences 20, no. 19: 4668. https://doi.org/10.3390/ijms20194668