Journal
DENTAL MATERIALS
Volume 28, Issue 2, Pages 219-228Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.dental.2011.10.004
Keywords
Bacterial adhesion; Cytotoxicity; Dental restorative material; Degree of conversion; Dimethacrylate monomer; Menschutkin reaction; MTT assay; Quaternary ammonium salts; Streptococcus mutans; Surface charge density
Funding
- National Institute of Dental and Craniofacial Research (NIDCR) [YI-DE-7005-01]
- National Institute of Standards and Technology (NIST) [YI-DE-7005-01]
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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. 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. 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. Significance. The Menschutkin reaction provides a facile, convenient means to synthesize new monomers with quaternary ammonium groups for dental and medical applications. Published by Elsevier Ltd on behalf of Academy of Dental Materials.
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