Novel hydrolytic resistant antibacterial monomers for dental resin adhesive

J Dent. 2023 Aug:135:104597. doi: 10.1016/j.jdent.2023.104597. Epub 2023 Jun 20.

Abstract

Objectives: To evaluate the properties of novel hydrolytic resistant antibacterial monomers and to determine the properties of resin adhesives containing these monomers.

Methods: Methacrylamide-based QAC (Quaternary Ammonium Compound) monomers, 1-(11-Methacryla-midoundecyl)pyridine-1-ium bromide (MAUPB) and 1-(12-Methacryl-amidododecyl)pyridine-1-ium bromide (MADPB), and their methacrylate-derivatives, N-(1-Methacryloylundecanyl)pyridinium bromide (MUPB) and N-(1-Methacryloyldodecanyl)pyridinium bromide (MDPB), were synthesized and characterized. The minimum inhibitory (MIC) and bactericidal (MBC) concentrations were determined against S.mutans and E.faecalis. Cytotoxicity of unpolymerized monomers were evaluated using L-929 and MDPC-23. Each monomer was incorporated into experimental resins (BisGMA/TEGDMA/CQ/EDMAB or BisGMA/HEMA/CQ/EDMAB) at 10wt%. FTIR Spectra were collected for degree of conversion (DC%) measurement. Bacterial attachment on resin disks were determined by fluorescent microscope. Mechanical properties of experimental resins were evaluated by flexural strength & modulus and shear bond strength testing.

Results: The antibacterial activity of MDPB≥MUPB>MADPB>MAUPB. The TC50 of MAUPB> MADPB>MUPB >MDPB. Incorporation of MAUPB in BisGMA/TEGDMA-based resin, had no significant effect on DC%, while significantly increase DC% in BisGMA/HEMA-based Resin. MUPB and MAUPB containing resins showed less viable bacterial attachment than pure resins. After 3-month storage, resins containing MAUPB illustrated higher flexural strength than their corresponding resins containing MUPB. BisGMA/HEMA-based resin containing MAUPB illustrated significantly higher resin-dentin shear bond strength than that of MUPB and pure resin.

Conclusions: Methacrylamide monomer containing QAC, MAUPB, possessed antibacterial properties and superior physical and mechanical properties when incorporated in resin adhesives as compared to their corresponding methacrylate monomer, MUPB.

Clinical significance: Methacrylamide-based QAC monomers are potentially used to formulate antibacterial hydrolytic resistant resin adhesives and enhance resin-dentin bond strength.

Keywords: Cytotoxicity; Degree of conversion; Dental bonding; Dentin; Flexural strength; Quaternary ammonium compound.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Bromides*
  • Composite Resins / chemistry
  • Composite Resins / pharmacology
  • Dental Cements*
  • Materials Testing
  • Methacrylates / chemistry
  • Methacrylates / pharmacology
  • Polymethacrylic Acids / pharmacology
  • Pyridines

Substances

  • hydroxyethyl methacrylate
  • triethylene glycol dimethacrylate
  • methacrylamide
  • Dental Cements
  • Bromides
  • Methacrylates
  • Polymethacrylic Acids
  • Anti-Bacterial Agents
  • Pyridines
  • Composite Resins