Ionic Dimethacrylates for Antimicrobial and Remineralizing Dental Composites

Two ionic dimethacrylates (IDMA1 and IDMA2) intended for utilization in multifunctional, antibacterial and remineralizing dental resins and composites were synthesized by nucleophilic substitution reactions. Crude IDMAs were purified by multi-step extraction from ethanol-diethyl ether-hexane solvent system. Their structures were validated by nuclear magnetic resonance and mass spectrometry. As evidenced by the water contact angle measurements ((63.2-65.5)⁰), IDMAs did not affect the wettability of urethane dimethacrylate (UDMA)- based copolymers (average contact angle ((60.8±5.1)⁰).The attained degrees of vinyl conversion increased from 88.1% (no-IDMA control) up to 93.0% (IDMA2 series). Flexural strength (FS) of copolymers was reduced from 94.8 MPa (control) to (68.9-71.8) MPa (IDMA counterparts) independent of monomer type and/or its concentration. This reduction in FS should not disqualify IDMAs from consideration as viable antibacterial agents in multifunctional restoratives. Tested at concentrations exceeding the expected leachability of unreacted monomers from cured copolymers and/or composites, IDMAs had no deleterious effect on viability and/or metabolic activity of fibroblasts. The remineralization potential of amorphous calcium phosphate IDMA/UDMA composites was confirmed by calcium and phosphate ion release kinetic experiments. Results of this study warrant in-depth biological, physicochemical, mechanical and antibacterial assessments of IDMA resins and composites to identify prototype(s) suitable for clinical testing.