Antibacterial resin monomers based on quaternary ammonium and their benefits in restorative dentistry

Jedrychowski, 1983, Antibacterial and mechanical properties of restorative materials combined with chlorhexidines, J Oral Rehabil, 10, 373, 10.1111/j.1365-2842.1983.tb00133.x Ribeiro, 1991, In vitro antibacterial effect of chlorhexidine added to glass-ionomer cements, Scand J Dent Res, 99, 533 Palmer, 2004, Chlorhexidine release from an experimental glass ionomer cement, Biomaterials, 25, 5423, 10.1016/j.biomaterials.2003.12.051 Imzato, 1993, Immobilization of an antibacterial component in composite resin, Dentistry in Japan, 30, 63 Imazato, 1994, Incorporation of bacterial inhibitor into resin composite, J Dent Res, 73, 1437, 10.1177/00220345940730080701 Xiao, 2008, Antibacterial effects of three experimental quaternary ammonium salt (QAS) monomers on bacteria associated with oral infections, J Oral Sci, 50, 323, 10.2334/josnusd.50.323 Punyani, 2006, Preparation of iodine containing quaternary amine methacrylate copolymers and their contact killing antimicrobial properties, J Appl Polym Sci, 102, 1038, 10.1002/app.24181 Punyani, 2007, Contact killing antimicrobial acrylic bone cements: preparation and characterization, J Biomater Sci Polym Ed, 18, 131, 10.1163/156856207779116748 Deb, 2008, PMMA bone cement containing a quaternary amine comonomer with potential antibacterial properties, J Biomed Mater Res B: Appl Biomater, 85, 130, 10.1002/jbm.b.30925 Caillier, 2009, Synthesis and antimicrobial properties of polymerizable quaternary ammoniums, Eur J Med Chem, 44, 3201, 10.1016/j.ejmech.2009.03.031 Gilbert, 2005, Cationic antiseptics: diversity of action under a common epithet, J Appl Microbiol, 99, 703, 10.1111/j.1365-2672.2005.02664.x McDonnell, 1999, Antiseptics and disinfectants: activity, action, and resistance, Clin Microbiol Rev, 12, 147, 10.1128/CMR.12.1.147 Marcotte, 2005, Permeability and thermodynamics study of quaternary ammonium surfactants–phosphocholine vesicle system, J Colloid Interface Sci, 292, 219, 10.1016/j.jcis.2005.05.060 Menger, 2000, Gemini surfactants, Angew Chem Int Ed Engl, 39, 1906, 10.1002/1521-3773(20000602)39:11<1906::AID-ANIE1906>3.0.CO;2-Q Maeda, 1999, Synthesis and antimicrobial characteristics of novel biocides, 4,4′-(1,6-hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium+++iodide)s, Chem Pharm Bull, 47, 1020, 10.1248/cpb.47.1020 Caillier, 2009, Polymerizable semi-fluorinated gemini surfactants designed for antimicrobial materials, J Colloid Interface Sci, 332, 201, 10.1016/j.jcis.2008.12.038 Huang, 2011, Antibacterial activity and cytotoxicity of two novel crosslinking antibacterial monomers on oral pathogens, Arch Oral Biol, 56, 367, 10.1016/j.archoralbio.2010.10.011 Antonucci, 2012, Synthesis and characterization of dimethacrylates containing quaternary ammonium functionalities for dental applications, Dent Mater, 28, 219, 10.1016/j.dental.2011.10.004 Imazato, 1999, Bactericidal activity and cytotoxicity of antibacterial monomer MDPB, Biomaterials, 20, 899, 10.1016/S0142-9612(98)00247-6 Imazato, 2001, Bactericidal effect of dentin primer containing antibacterial monomer methacryloyloxydodecylpyridinium bromide (MDPB) against bacteria in human carious dentin, J Oral Rehabil, 28, 314, 10.1046/j.1365-2842.2001.00659.x Imazato, 2008, Determination of bactericidal activity of antibacterial monomer MDPB by a viability staining method, Dent Mater J, 27, 145, 10.4012/dmj.27.145 Yoshikawa, 2007, The effect of antibacterial monomer MDPB on the growth of organisms associated with root caries, Dent Mater J, 26, 388, 10.4012/dmj.26.388 Izutani, 2011, Effects of the antibacterial monomer 12-methacryloyloxydodecylpyridinium bromide (MDPB) on bacterial viability and metabolism, Eur J Oral Sci, 119, 175, 10.1111/j.1600-0722.2011.00817.x Ma, 2012, Assessment of bactericidal effects of quaternary ammonium-based antibacterial monomers in combination with colloidal platinum nanoparticles, Dent Mater J, 31, 150, 10.4012/dmj.2011-180 Izutani, 2010, Antibacterial effects of MDPB against anaerobes associated with endodontic infections, Int Endod J, 43, 637, 10.1111/j.1365-2591.2010.01716.x Schweikl, 2006, Genetic and cellular toxicology of dental resin monomers, J Dent Res, 85, 870, 10.1177/154405910608501001 Nishida, 2010, The influence of the antibacterial monomer 12-methacryloyloxydodecylpyridinium bromide on the proliferation, differentiation and mineralization of odontoblast-like cells, Biomaterials, 31, 1518, 10.1016/j.biomaterials.2009.11.023 Chai, 2011, The bonding property and cytotoxicity of a dental adhesive incorporating a new antibacterial monomer, J Oral Rehabil, 38, 849, 10.1111/j.1365-2842.2011.02212.x Imazato, 1995, Antibacterial activity of MDPB polymer incorporated in dental resin, J Dent, 23, 177, 10.1016/0300-5712(95)93576-N Imazato, 1998, Antibacterial activity of cured dental resin incorporating the antibacterial monomer MDPB and an adhesion-promoting monomer, J Biomed Mater Res, 39, 511, 10.1002/(SICI)1097-4636(19980315)39:4<511::AID-JBM1>3.0.CO;2-M Kügler, 2005, Evidence of a charge-density threshold for optimum efficiency of biocidal cationic surfaces, Microbiology, 151, 1341, 10.1099/mic.0.27526-0 Murata, 2007, Permanent, non-leaching antibacterial surface – 2: how high density cationic surfaces kill bacterial cells, Biomaterials, 28, 4870, 10.1016/j.biomaterials.2007.06.012 Cen, 2007, Surface functionalization technique for conferring antibacterial properties to polymeric and cellulosic surfaces, Langmuir, 19, 10295, 10.1021/la035104c Müller, 2009, Influences of protein films on antibacterial or bacteria-repellent surface coatings in a model system using silicon wafers, Biomaterials, 30, 4921, 10.1016/j.biomaterials.2009.05.079 Imazato, 1998, Antibacterial activity of dentine primer containing MDPB after curing, J Dent, 26, 267, 10.1016/S0300-5712(97)00013-4 Imazato, 2003, Antibacterial activity and bonding characteristics of an adhesive resin containing antibacterial monomer MDPB, Dent Mater, 19, 313, 10.1016/S0109-5641(02)00060-X Ebi, 2001, Inhibitory effects of resin composite containing bactericide-immobilized filler on plaque accumulation, Dent Mater, 17, 485, 10.1016/S0109-5641(01)00006-9 Imazato, 2003, Antibacterial activity of bactericide-immobilized filler for resin-based restoratives, Biomaterials, 24, 3605, 10.1016/S0142-9612(03)00217-5 Thomé, 2009, In vitro analysis of inhibitory effects of the antibacterial monomer MDPB-containing restorations on the progression of secondary root caries, J Dent, 37, 705, 10.1016/j.jdent.2009.05.024 Xiao, 2009, Antibacterial activity and bonding ability of an adhesive incorporating an antibacterial monomer DMAE-CB, Biomed Mater Res B Appl Biomater, 90, 813, 10.1002/jbm.b.31350 Li, 2009, Anti-biofilm effect of dental adhesive with cationic monomer, J Dent Res, 88, 372, 10.1177/0022034509334499 Li, 2011, The effect of an antibacterial monomer on the antibacterial activity and mechanical properties of a pit-and-fissure sealant, J Am Dent Assoc, 142, 184, 10.14219/jada.archive.2011.0062 Breschi, 2008, Dental adhesion review: aging and stability of the bonded interface, Dent Mater, 24, 90, 10.1016/j.dental.2007.02.009 Pashley, 2011, State of the art etch-and-rinse adhesives, Dent Mater, 27, 1, 10.1016/j.dental.2010.10.016 Carrilho, 2007, Chlorhexidine preserves dentin bond in vitro, J Dent Res, 86, 90, 10.1177/154405910708600115 Tezvergil-Mutluay, 2011, The inhibitory effects of quaternary ammonium methacrylates on soluble and matrix-bound MMPs, J Dent Res, 90, 535, 10.1177/0022034510389472 Pashley, 2011, How to increase the durability of resin-dentin bonds, Compend Contin Educ Dent, 32, 60 Donmez, 2005, Ultrastructural correlates of in vivo/in vitro bond degradation in self-etch adhesives, J Dent Res, 84, 355, 10.1177/154405910508400412 Nakajima, 2003, The durability of a fluoride-releasing resin adhesive system to dentin, Oper Dent, 28, 186 Imazato, 1997, Incorporation of antibacterial monomer MDPB into dentin primer, J Dent Res, 76, 768, 10.1177/00220345970760030901 Imazato, 1994, Influence of incorporation of antibacterial monomer on curing behavior of a dental composite, J Dent Res, 73, 1641, 10.1177/00220345940730100901 Imazato, 1999, Water sorption and colour stability of composites containing the antibacterial monomer MDPB, J Dent, 7, 279, 10.1016/S0300-5712(98)00006-2 Imazato, 2006, In vitro antibacterial effects of the dentin primer of Clearfil Protect Bond, Dent Mater, 22, 527, 10.1016/j.dental.2005.05.009 Schmalz, 2002, Cytotoxicity of low pH dentin-bonding agents in a dentin barrier test in vitro, J Endod, 28, 188, 10.1097/00004770-200203000-00011 Schmalz, 2004, Effect of dentin on the antibacterial activity of dentin bonding agents, J Endod, 30, 352, 10.1097/00004770-200405000-00011 Imazato, 2004, In vivo antibacterial effects of dentin primer incorporating MDPB, Oper Dent, 29, 369 Özer, 2003, Comparison of antibacterial activity of two dentin bonding systems using agar well technique and tooth cavity model, J Dent, 31, 111, 10.1016/S0300-5712(03)00006-X Polydorou, 2006, Antibacterial effect of an ozone device and its comparison with two dentin-bonding systems, Eur J Oral Sci, 114, 349, 10.1111/j.1600-0722.2006.00363.x Türkün, 2006, Is an antibacterial adhesive system more effective than cavity disinfectants?, Am J Dent, 19, 166 Vaidyanathan, 2009, Antimicrobial properties of dentine bonding agents determined using in vitro and ex vivo methods, J Dent, 37, 514, 10.1016/j.jdent.2009.03.007 Imazato, 2007, An in vivo evaluation of bonding ability of comprehensive antibacterial adhesive system incorporating MDPB, Dent Mater, 23, 170, 10.1016/j.dental.2006.01.005 De Munck, 2003, Microtensile bond strengths of one- and two-step self-etch adhesives to bur-cut enamel and dentin, Am J Dent, 16, 414 Chan, 2003, Bonding of mild self-etching primers/adhesives to dentin with thick smear layers, Am J Dent, 16, 340 Yoshiyama, 2002, Bonding of self-etch and total-etch adhesives to carious dentin, J Dent Res, 81, 556, 10.1177/154405910208100811 Sonoda, 2005, An in vitro investigation of microtensile bond strengths of two dentine adhesives to caries-affected dentine, J Dent, 33, 335, 10.1016/j.jdent.2004.09.009 Doi, 2004, Bonding to root caries by a self-etching adhesive system containing MDPB, Am J Dent, 17, 89 Imazato, 2000, Cytotoxic effects of composite restorations employing self-etching primers or experimental antibacterial primers, J Dent, 28, 61, 10.1016/S0300-5712(99)00039-1 Koulaouzidou, 2008, Cytotoxicity evaluation of an antibacterial dentin adhesive system on established cell lines, J Biomed Mater Res B Appl Biomater, 84, 271, 10.1002/jbm.b.30870 Lanza, 2009, Transdentinal diffusion and cytotoxicity of self-etching adhesive systems, Cell Biol Toxicol, 25, 533, 10.1007/s10565-008-9110-x Kusdemir, 2011, Evaluation of cytotoxic effects of six self-etching adhesives with direct and indirect contact tests, Dent Mater J, 30, 799, 10.4012/dmj.2011-046 Imazato, 2002, Penetration of an antibacterial dentine-bonding system into demineralized human root dentine in vitro, Eur J Oral Sci, 110, 168, 10.1034/j.1600-0722.2002.11221.x Kuramoto, 2005, Inhibition of progression of root caries by an antibacterial adhesive, J Dent Res, 84, 89, 10.1177/154405910508400116 Kaneshiro, 2008, Effects of a self-etching resin coating system to prevent demineralization of root surfaces, Dent Mater, 24, 1420, 10.1016/j.dental.2008.03.003 Cooper, 2010, Inflammation-regeneration interplay in the dentine-pulp complex, J Dent, 38, 687, 10.1016/j.jdent.2010.05.016 Cox, 2003, Pulp healing and dentin bridge formation adjacent to an antimicrobial adhesive: a long-term usage study, 85 Tziafas, 2007, Effects of a new antibacterial adhesive on the repair capacity of the pulp-dentine complex in infected teeth, Int Endod J, 40, 58, 10.1111/j.1365-2591.2006.01183.x Yuan, 2008, Hybridization quality in cervical cementum and superficial dentin using current adhesives, Dent Mater, 24, 584, 10.1016/j.dental.2007.05.020