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Synthesis and characterization of dimethacrylates containing quaternary ammonium functionalities for dental applications.
- Source :
-
Dental materials : official publication of the Academy of Dental Materials [Dent Mater] 2012 Feb; Vol. 28 (2), pp. 219-28. Date of Electronic Publication: 2011 Oct 27. - Publication Year :
- 2012
-
Abstract
- Objectives: The widespread incidence of recurrent caries highlights the need for improved dental restorative materials. The objective of this study was to synthesize low viscosity ionic dimethacrylate monomers (IDMAs) that contain quaternary ammoniums groups (antimicrobial functionalities) and are compatible with existing dental dimethacrylate-based monomers. Such monomers have the potential to copolymerize with other methacrylate monomers and produce antibacterial polymers.<br />Methods: Two monomers (IDMA-1 and IDMA-2) were synthesized using the Menschutkin reaction and incorporated at 0-30% (by mass) into a 1:1 (by mass) bisphenol A glycerolate dimethacrylate (BisGMA):triethylene glycol dimethacrylate (TEGDMA) resin. Resin viscosity was quantified using rheology, and polymer degree of conversion (DC) and surface charge density were measured using Fourier transform infrared spectroscopy (FTIR) and fluorescein binding, respectively. Effects of IDMA-1 on initial attachment of Streptococcus mutans and on viability and metabolic activity (via reductase enzymes) of RAW 264.7 macrophage-like cells were quantified.<br />Results: IDMA-1 and IDMA-2 were prepared and characterized. IDMA-1 was miscible with BisGMA:TEGDMA and slightly increased the resin viscosity and DC. As expected, polymeric surface charge density increased with increasing IDMA-1. Incorporation of 10% IDMA-1 into BisGMA:TEGDMA reduced bacterial colonization without affecting viability or metabolic activity of mammalian cells. Increasing IDMA-1 up to 30% had no additional effect on bacterial coverage, but ≥20% IDMA-1 significantly reduced macrophage density, viability, and metabolic activity. Leachables from polymers containing IDMA-1 were not cytotoxic.<br />Significance: The Menschutkin reaction provides a facile, convenient means to synthesize new monomers with quaternary ammonium groups for dental and medical applications.<br /> (Published by Elsevier Ltd.)
- Subjects :
- Animals
Anti-Infective Agents chemistry
Anti-Infective Agents pharmacology
Bacterial Adhesion drug effects
Bisphenol A-Glycidyl Methacrylate chemistry
Cell Count
Cell Line
Cell Survival drug effects
Dental Materials chemistry
Dental Materials pharmacology
Fluoresceins
Fluorescent Dyes
Macrophages drug effects
Materials Testing
Methacrylates chemistry
Methacrylates pharmacology
Microbial Viability drug effects
Polyethylene Glycols chemistry
Polymerization
Polymethacrylic Acids chemistry
Quaternary Ammonium Compounds pharmacology
Rheology
Spectroscopy, Fourier Transform Infrared
Streptococcus mutans drug effects
Surface Properties
Viscosity
Dental Materials chemical synthesis
Methacrylates chemical synthesis
Quaternary Ammonium Compounds chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1879-0097
- Volume :
- 28
- Issue :
- 2
- Database :
- MEDLINE
- Journal :
- Dental materials : official publication of the Academy of Dental Materials
- Publication Type :
- Academic Journal
- Accession number :
- 22035983
- Full Text :
- https://doi.org/10.1016/j.dental.2011.10.004