Physicochemical, Mechanical, and Antimicrobial Properties of Novel Dental Polymers Containing Quaternary Ammonium and Trimethoxysilyl Functionalities

Abstract

The aims of this study were to evaluate the physicochemical and mechanical properties, antimicrobial (AM) functionality, and cytotoxic potential of novel dental polymers containing quaternary ammonium and trimethoxysilyl functionalities (e.g., N-(2-(methacryloyloxy)ethyl)-N,N-dimethyl-3-(trimethoxysilyl)propan-1-aminium iodide (AMsil1) and N-(2-(methacryloyloxy)ethyl)-N,N-dimethyl-11-(trimethoxysilyl)undecan-1-aminium bromide (AMsil2)). AMsil1 or AMsil2 were incorporated into light-cured (camphorquinone + ethyl-4-N,N-dimethylamino benzoate) urethane dimethacrylate (UDMA)/polyethylene glycol-extended UDMA/ethyl 2-(hydroxymethyl)acrylate (EHMA) resins (hereafter, UPE resin) at 10 or 20 mass %. Cytotoxic potential was assessed by measuring viability and metabolic activity of immortalized mouse connective tissue and human gingival fibroblasts in direct contact with monomers. AMsil–UPE resins were evaluated for wettability by contact angle measurements and degree of vinyl conversion (DVC) by near infra-red spectroscopy analyses. Mechanical property evaluations entailed flexural strength (FS) and elastic modulus (E) testing of copolymer specimens. The AM properties were assessed using Streptococcus mutans (planktonic and biofilm forms) and Porphyromonas gingivalis biofilm. Neither AMsil exhibited significant toxicity in direct contact with cells at biologically relevant concentrations. Addition of AMsils made the UPE resin more hydrophilic. DVC values for the AMsil–UPE copolymers were 2–31% lower than that attained in the UPE resin control. The mechanical properties (FS and E) of AMsil–UPE specimens were reduced (11–57%) compared to the control. Compared to UPE resin, AMsil1–UPE and AMsil2–UPE (10% mass) copolymers reduced S. mutans biofilm 4.7- and 1.7-fold, respectively (p ≤ 0.005). Although not statistically different, P. gingivalis biofilm biomass on AMsil1–UPE and AM AMsil2–UPE copolymer disks were lower (71% and 85%, respectively) than that observed with a commercial AM dental material. In conclusion, the AM function of new monomers is not inundated by their toxicity towards cells. Despite the reduction in mechanical properties of the AMsil–UPE copolymers, AMsil2 is a good candidate for incorporation into multifunctional composites due to the favorable overall hydrophilicity of the resins and the satisfactory DVC values attained upon light polymerization of AMsil-containing UDMA/PEG-U/EHMA copolymers.