One-pot synthesis of antibacterial monomers with dual biocidal modes

Wei Zhang, Xiao Juan Luo, Li Na Niu, Si Ying Liu, Wan Chun Zhu, Jeevanie Epasinghe, Liang Chen, Guo Hua Li, Cui Huang, Jing Mao, David Henry Pashley, Franklin Chi Meng Tay

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Objectives The present study reported a method for preparing a blend of antibacterial quaternary ammonium silanes and quaternary ammonium methacryloxy silane (QAMS) based on the sol-gel reaction between dimethyldiethoxy silane and two trialkoxysilanes, one with an antibacterial quaternary ammonium functionality and the other with a methacryloxy functionality. Methods Reaction products of the sol-gel reaction were characterised by direct infusion mass spectrometry, FTIR and proton, carbon and silicon NMR. This blend of monomers was incorporated into an experimental universal adhesive for evaluation of antimicrobial activity against Streptococcus mutans biofilms, microtensile bond strength and cytotoxicty. Retention of quaternary ammonium species on polymerised adhesive, leaching of these species from the adhesive and the ability of resin-dentine interfaces to inhibit S. mutans biofilms were evaluated over a 3-month water-ageing period. Results The antibacterial adhesive version killed bacteria in S. mutans biofilms not only through the release of non-copolymerisable quaternary ammonium silane species (release-killing), but also via immobilised quaternary ammonium methacryloxy silane that are copolymerised with adhesive resin comonomers (contact-killing). Contact-killing was retained after water-ageing. The QAMS-containing universal adhesive has similar tensile bond strength as the control and two commercially available universal adhesives, when it was used for bonding to dentine in the etch-and-rinse mode and self-etching mode. Incorporation of the antimicrobial quaternary ammonium species blend did not adversely affect the cytotoxicity of the universal adhesive formulation. Conclusions Instead of using quaternary ammonium dimethacrylates and nanosilver, an alternative bimodal antimicrobial strategy for formulating antimicrobial universal dentine adhesives is achieved using the one-pot sol-gel synthesis scheme. Clinical Significance The QAMS containing universal dentine adhesives with dual antimicrobial activity is a promising material aimed at preventing second caries and prolonging the longevity of resin composite restorations.

Original languageEnglish (US)
Pages (from-to)1078-1095
Number of pages18
JournalJournal of Dentistry
Volume42
Issue number9
DOIs
StatePublished - Jan 1 2014

Fingerprint

Ammonium Compounds
Adhesives
Silanes
Dentin
Streptococcus mutans
Polymethyl Methacrylate
Biofilms
Gels
Water
Composite Resins
Tensile Strength
Silicon
Fourier Transform Infrared Spectroscopy
Protons
Mass Spectrometry
Carbon
Bacteria

Keywords

  • Antibacterial
  • Biofilm
  • Dual biocidal modes
  • Interface
  • Universal adhesive

ASJC Scopus subject areas

  • Dentistry(all)

Cite this

Zhang, W., Luo, X. J., Niu, L. N., Liu, S. Y., Zhu, W. C., Epasinghe, J., ... Tay, F. C. M. (2014). One-pot synthesis of antibacterial monomers with dual biocidal modes. Journal of Dentistry, 42(9), 1078-1095. https://doi.org/10.1016/j.jdent.2014.06.001

One-pot synthesis of antibacterial monomers with dual biocidal modes. / Zhang, Wei; Luo, Xiao Juan; Niu, Li Na; Liu, Si Ying; Zhu, Wan Chun; Epasinghe, Jeevanie; Chen, Liang; Li, Guo Hua; Huang, Cui; Mao, Jing; Pashley, David Henry; Tay, Franklin Chi Meng.

In: Journal of Dentistry, Vol. 42, No. 9, 01.01.2014, p. 1078-1095.

Research output: Contribution to journalArticle

Zhang, W, Luo, XJ, Niu, LN, Liu, SY, Zhu, WC, Epasinghe, J, Chen, L, Li, GH, Huang, C, Mao, J, Pashley, DH & Tay, FCM 2014, 'One-pot synthesis of antibacterial monomers with dual biocidal modes', Journal of Dentistry, vol. 42, no. 9, pp. 1078-1095. https://doi.org/10.1016/j.jdent.2014.06.001
Zhang W, Luo XJ, Niu LN, Liu SY, Zhu WC, Epasinghe J et al. One-pot synthesis of antibacterial monomers with dual biocidal modes. Journal of Dentistry. 2014 Jan 1;42(9):1078-1095. https://doi.org/10.1016/j.jdent.2014.06.001
Zhang, Wei ; Luo, Xiao Juan ; Niu, Li Na ; Liu, Si Ying ; Zhu, Wan Chun ; Epasinghe, Jeevanie ; Chen, Liang ; Li, Guo Hua ; Huang, Cui ; Mao, Jing ; Pashley, David Henry ; Tay, Franklin Chi Meng. / One-pot synthesis of antibacterial monomers with dual biocidal modes. In: Journal of Dentistry. 2014 ; Vol. 42, No. 9. pp. 1078-1095.
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abstract = "Objectives The present study reported a method for preparing a blend of antibacterial quaternary ammonium silanes and quaternary ammonium methacryloxy silane (QAMS) based on the sol-gel reaction between dimethyldiethoxy silane and two trialkoxysilanes, one with an antibacterial quaternary ammonium functionality and the other with a methacryloxy functionality. Methods Reaction products of the sol-gel reaction were characterised by direct infusion mass spectrometry, FTIR and proton, carbon and silicon NMR. This blend of monomers was incorporated into an experimental universal adhesive for evaluation of antimicrobial activity against Streptococcus mutans biofilms, microtensile bond strength and cytotoxicty. Retention of quaternary ammonium species on polymerised adhesive, leaching of these species from the adhesive and the ability of resin-dentine interfaces to inhibit S. mutans biofilms were evaluated over a 3-month water-ageing period. Results The antibacterial adhesive version killed bacteria in S. mutans biofilms not only through the release of non-copolymerisable quaternary ammonium silane species (release-killing), but also via immobilised quaternary ammonium methacryloxy silane that are copolymerised with adhesive resin comonomers (contact-killing). Contact-killing was retained after water-ageing. The QAMS-containing universal adhesive has similar tensile bond strength as the control and two commercially available universal adhesives, when it was used for bonding to dentine in the etch-and-rinse mode and self-etching mode. Incorporation of the antimicrobial quaternary ammonium species blend did not adversely affect the cytotoxicity of the universal adhesive formulation. Conclusions Instead of using quaternary ammonium dimethacrylates and nanosilver, an alternative bimodal antimicrobial strategy for formulating antimicrobial universal dentine adhesives is achieved using the one-pot sol-gel synthesis scheme. Clinical Significance The QAMS containing universal dentine adhesives with dual antimicrobial activity is a promising material aimed at preventing second caries and prolonging the longevity of resin composite restorations.",
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AU - Niu, Li Na

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AU - Epasinghe, Jeevanie

AU - Chen, Liang

AU - Li, Guo Hua

AU - Huang, Cui

AU - Mao, Jing

AU - Pashley, David Henry

AU - Tay, Franklin Chi Meng

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N2 - Objectives The present study reported a method for preparing a blend of antibacterial quaternary ammonium silanes and quaternary ammonium methacryloxy silane (QAMS) based on the sol-gel reaction between dimethyldiethoxy silane and two trialkoxysilanes, one with an antibacterial quaternary ammonium functionality and the other with a methacryloxy functionality. Methods Reaction products of the sol-gel reaction were characterised by direct infusion mass spectrometry, FTIR and proton, carbon and silicon NMR. This blend of monomers was incorporated into an experimental universal adhesive for evaluation of antimicrobial activity against Streptococcus mutans biofilms, microtensile bond strength and cytotoxicty. Retention of quaternary ammonium species on polymerised adhesive, leaching of these species from the adhesive and the ability of resin-dentine interfaces to inhibit S. mutans biofilms were evaluated over a 3-month water-ageing period. Results The antibacterial adhesive version killed bacteria in S. mutans biofilms not only through the release of non-copolymerisable quaternary ammonium silane species (release-killing), but also via immobilised quaternary ammonium methacryloxy silane that are copolymerised with adhesive resin comonomers (contact-killing). Contact-killing was retained after water-ageing. The QAMS-containing universal adhesive has similar tensile bond strength as the control and two commercially available universal adhesives, when it was used for bonding to dentine in the etch-and-rinse mode and self-etching mode. Incorporation of the antimicrobial quaternary ammonium species blend did not adversely affect the cytotoxicity of the universal adhesive formulation. Conclusions Instead of using quaternary ammonium dimethacrylates and nanosilver, an alternative bimodal antimicrobial strategy for formulating antimicrobial universal dentine adhesives is achieved using the one-pot sol-gel synthesis scheme. Clinical Significance The QAMS containing universal dentine adhesives with dual antimicrobial activity is a promising material aimed at preventing second caries and prolonging the longevity of resin composite restorations.

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