Synthesis and antibacterial activities of novel polymerizable Gemini quaternary ammonium monomers

References

• He JW, Söderling E, Vallittu PK, Lassila LVJ. Investigation of double bond conversion, mechanical properties, and antibacterial activity of dental resins with different alkyl chain length quaternary ammonium methacrylate monomers (QAM). J. Biomater. Sci., Polym. Ed. 2013;5:565–573.10.1080/09205063.2012.699709
   Google Scholar
• Pupo YM, Farago PV, Nadal JM, Esmerino LA, Maluf DF, Zawadzki SF, Michél MD, Santos FA, Gomes OMM, Gomes JC. An innovative quaternary ammonium methacrylatepolymer can provide improved antimicrobial properties for a dental adhesive system. J. Biomater. Sci., Polym. Ed. 2013;24:1443–1458.10.1080/09205063.2013.766784
   PubMed Web of Science ®Google Scholar
• Zhang Y, Ding MM, Zhou LJ, Tan H, Li JH, Xiao HN, Li JS, Snow J. Synthesis and antibacterial characterization of gemini surfactantmonomers and copolymers. Polym. Chem. 2012;3:907–913.10.1039/c2py00558a
   Google Scholar
• Ayfer B, Dizman B, Elasri MO, Mathias LJ, Avci D. Synthesis and antibacterial activities of new quaternary ammonium monomers. Des. Monomers Polym. 2005;8:437–451.10.1163/1568555054937935
   Web of Science ®Google Scholar
• Dizman B, Elasri MO, Mathias LJ. Synthesis and antimicrobial activities of new water-soluble bis-quaternary ammonium methacrylate polymers. J. Appl. Polym. Sci. 2004;94:635–642.10.1002/(ISSN)1097-4628
   Web of Science ®Google Scholar
• Mathias LJ, Shemper BS, Alirol M, Morizur JF. Synthesis of new hydroxylated monomers based on methacrylate, dimethacrylate, and tetramethacrylate michael adducts and photopolymerization kinetics of bulk cross-linkers. Macromolecules. 2004;37:3231–3238.10.1021/ma035260q
   Web of Science ®Google Scholar
• Gao CL, Wu XE, Lv GH, Ding MX, Gao LX. Syntheses and properties of soluble biphenyl-based polyimides from asymmetric bis(chlorophthalimide)s. Macromolecules. 2004;37:2754–2761.10.1021/ma0350720
   Web of Science ®Google Scholar
• Chern YT, Tsai JY. Low dielectric constant and high organosolubility of novel polyimide derived from unsymmetric 1,4-Bis(4-aminophenoxy)-2,6-di-tert-butylbenzene. Macromolecules. 2008;41:9556–9564.10.1021/ma802305q
   Web of Science ®Google Scholar
• Yang CP, Su YY, Wu KL. Synthesis and properties of new aromatic polyimides based on 2,5-bis(4-amino-2-trifluoromethylphenoxy)-tert-butylbenzene and various aromatic dianhydrides. J. Polym. Sci., Part A: Polym. Chem. 2004;42:5424–5438.10.1002/(ISSN)1099-0518
   Web of Science ®Google Scholar
• Xue Y, Guan Y, Zheng A, Wang H, Xiao H. Synthesis and characterization of ciprofloxacin pendant antibacterial cationic polymers. J. Biomater. Sci., Polym. Ed. 2012;23:1115–1128.10.1163/092050611X576639
   PubMed Web of Science ®Google Scholar
• Kusama M, Matsumoto T, Kurosaki T. Soluble polyimides with polyalicyclic structure.3. polyimides from (4arH,8acH)-decahydro-1t,4t:5c,8c-dimethanonaphthalene- 2t,3t,6c,7c-tetracarboxylic 2,3:6,7-dianhydride. Macromolecules. 1994;27:1117–1123.10.1021/ma00083a008
   Web of Science ®Google Scholar
• Li WM, Li SH, Zhang QY, Zhang SB. Synthesis of bis(amine anhydride)s for novel High Tgs and organosoluble poly(amine imide)s by palladium-catalyzed amination of 4-chlorophthalide anhydride. Macromolecules. 2007;40:8205–8211.10.1021/ma071213c
   Web of Science ®Google Scholar
• Koohmareh GA. New organo-soluble polyimides based on a new dianhydride: 4-(4-t-butyl-phenyl)-2,6-bis(3,4-phenyl dicarboxylic acid anhydride)pyridine. Des. Monomers Polym. 2007;10:517–525.10.1163/156855507782401169
   Web of Science ®Google Scholar
• Liaw DJ, Hsu PN, Chen WH, Lin SL. High glass transitions of new polyamides, polyimides, and poly(amide−imide)s containing a triphenylamine group:  synthesis and characterization. Macromolecules. 2002;35:4669–4676.10.1021/ma001523u
   Web of Science ®Google Scholar
• Kim HS, Kim YH, Ahn SK, Kwon SK. Synthesis and characterization of highly soluble and oxygen permeable new polyimides bearing a noncoplanar twisted biphenyl unit Containing tert-butylphenyl or trimethylsilyl phenyl groups. Macromolecules. 2003;36:2327–2332.10.1021/ma0214557
   Web of Science ®Google Scholar
• Patel HS, Patel VC. New monomers for polyimides. Des. Monomers Polym. 2000;3:191–197.10.1163/156855500300142889
   Web of Science ®Google Scholar
• Mikroyannidis JA, Spiliopoulos IK. Soluble phenyl- or alkoxyphenyl-substituted rigid-rod polyamides and polyimides containing m-Terphenyls in the main chain. Macromolecules. 1998;31:1236–1245.
   Web of Science ®Google Scholar
• Andrzejewska E, Marcinkowska A. New aspects of viscosity effects on the photopolymerization kinetics of the 2,2-bis[4-(2-hydroxymethacryloxypropoxy)phenyl]propane/triethylene glycol dimethacrylate monomer system. J. Appl. Polym. Sci. 2008;110:2780–2786.10.1002/app.v110:5
   Web of Science ®Google Scholar
• Dickens SH, Stansbury JW, Choi KM, Floyd CJE. Photopolymerization kinetics of methacrylate dental resins. Macromolecules. 2003;36:6043–6053.10.1021/ma021675 k
   Web of Science ®Google Scholar
• Abbanat D, Macielag M, Bush K. Novel antibacterial agents for the treatment of serious Gram-positive infection. Expert Opin. Invest. Drugs. 2003;12:379–399.10.1517/eid.2003.12.issue-3
   PubMed Web of Science ®Google Scholar
• Kourai H, Yabuhara T, Shirai A, Maeda T, Nagamune H. Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds. Eur. J. Med. Chem. 2006;41:437–444.10.1016/j.ejmech.2005.10.021
   PubMed Web of Science ®Google Scholar
• Pérez L, Torres JL, Manresa A, Solans C, Infante MR. Synthesis, aggregation, and biological properties of a new class of gemini cationic amphiphilic compounds from arginine, bis(Args). Langmuir. 1996;12:5296–5301.10.1021/la960301f
   Web of Science ®Google Scholar
• Fisicaro E, Compari C, Duce E, Donofrio G, Rozycka-Roszak B, Wozniak E. Biologically active bisquaternary ammonium chlorides: physico–chemical properties of long chain amphiphiles and their evaluation as non-viral vectors for gene delivery. Biochim. Biophys. Acta. 2005;1722:224–233.10.1016/j.bbagen.2004.12.013
   PubMed Web of Science ®Google Scholar
• Hoque J, Akkapeddi P, Yarlagadda V, Uppu DS, Kumar P, Haldar J. Cleavable cationic antibacterial amphiphiles: synthesis, mechanism of action, and cytotoxicities. Langmuir. 2012;28:12225–12234.10.1021/la302303d
   PubMed Web of Science ®Google Scholar
• Obłak E, Piecuch A, Krasowska A, Luczyński J. Antifungal activity of gemini quaternary ammonium salts. Microbiol. Res. 2013;3:9–638.
   Google Scholar
• Brycki B. Gemini alkylammonium salts as biodeterioration inhibitors. J. Microbiol. 2010;59:227–231.
   Google Scholar
• Zana R. Effect of the spacer group on the association behavior in aqueous solution. J. Colloid Interface Sci. 2002;248:203–220.10.1006/jcis.2001.8104
   PubMed Web of Science ®Google Scholar
• Lee SB, Koepsel RR, Morley SW, Matyjaszewski K, Sun Y, Russell AJ. Permanent, nonleaching antibacterial surfaces. 1. synthesis by atom transfer radical polymerization. Biomacromolecules. 2004;5:877–882.10.1021/bm034352 k
   PubMed Web of Science ®Google Scholar
• Kanazawa A, Ikeda T, Endo T. Novel polycationic biocides: synthesis and antibacterial activity of polymeric phosphonium salts. J. Polym. Sci., Part A: Polym. Chem. 1993;31:335–343.10.1002/pola.1993.080310205
   Web of Science ®Google Scholar
• Rabea EI, Badawy ME-T, Stevens CV, Smagghe G, Steurbaut W. Chitosan as antimicrobial agent:  applications and mode of action. Biomacromolecules. 2003;4:1457–1465.10.1021/bm034130 m
   PubMed Web of Science ®Google Scholar
• Inchausti I, Sasia PM, Katime I. Copolymerization of dimethylaminoethylacrylate-methyl chloride and acrylamide in inverse emulsion. J. Mater. Sci. 2005;40:4833–4838.10.1007/s10853-005-2003-y
   Web of Science ®Google Scholar
• Cakmak I, Ulukanli Z, Tuzcu M, Karabuga S, Genctav K. Synthesis and characterization of novel antimicrobial cationic polyelectrolytes. Eur. Polym. J. 2004;40:2373–2379.10.1016/j.eurpolymj.2004.06.004
   Web of Science ®Google Scholar
• Beyth N, Yudovin-Farber I, Bahir R, Domb AJ, Weiss EI. Antibacterial activity of dental composites containing quaternary ammonium polyethylenimine nanoparticles against Streptococcus mutans. Biomaterials. 2006;27:3995–4002.10.1016/j.biomaterials.2006.03.003
   PubMed Web of Science ®Google Scholar
• Kourai H, Yabuhara T, Shirai A, Maeda T, Nagamune H. Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds. Eur. J. Med. Chem. 2006;41:437–444.10.1016/j.ejmech.2005.10.021
   PubMed Web of Science ®Google Scholar
• Dizman B, Elasri MO, Mathias LJ. Synthesis and characterization of antibacterial and temperature responsive methacrylamide polymers. Macromolecules. 2006;39:5738–5746.10.1021/ma0607620
   Google Scholar
• Dizman B, Elasri MO, Mathias LJ. Synthesis, characterization, and antibacterial activities of novel methacrylate polymers containing norfloxacin. Biomacromol. 2005;6:514–520.10.1021/bm049383+
   PubMed Web of Science ®Google Scholar
• Yuan SL, Cai ZT, Xu GY, Jiang YS. Mesoscopic simulation study on the interaction between polymer and C12NBr or C(9) phNBr in aqueous solution. Colloid Polym. Sci. 2003;281:1069–1075.10.1007/s00396-003-0881-6
   Google Scholar
• Kokai TK. (Bromoacetoxy) alkyl methacrylates[P]. Japan JP 56156237. 1981.
   Google Scholar