The reaction was performed under nitrogen atmosphere with reflux at 120 ☌ for 2 h. To this solution, 0.5 wt% and 0.1 wt%, respectively, of HQ (an inhibitor used to prevent vinyl and allyl polymerization possibility under the applied reaction condition) and Ph 3P (a catalyst applied to facilitate ring opening-based etherification reaction) with respect to the total weight of monomers were added. Briefly, equimolar amounts of the reactants, Eg and GMA, were homogenized, with stirring, in a three-necked round-bottom flask. Įugenyl-2-hydroxypropyl methacrylate (EgGMA) was synthesized using a previously reported method. Generally, the favored properties of any dental composite additive are its ability to demonstrate an effective antimicrobial activity without compromising cytotoxicity on human cells, and other desirable properties. Such behaviors may be a result of the crosslinking reaction due to the participation of the allylic group present in the eugenol derivatives. , who reported enhanced cement properties, including mechanical and bactericidal effect against certain bacteria strains. Moreover, an experiment concerning the formulation of various polymerizable Eg-derivatives for dental and orthopedic applications were conducted by Rojo et al. However, the polymerization degree of conversion, curing depths, and exotherm were decreased with respect to the increase in EgMA. investigated various properties of dual-cured dental composites incorporating eugenyl methacrylate (EgMA) as in post and core build-up restoration. In this context, a number of polymerizable Eg-derivates have been synthesized, and their physical, chemical, mechanical and biological properties have been reported. The overall cytotoxicity test against NIH/3T3 fibroblast cell line (NIH Swiss 3-day transfer, inoculum 3 × 10 5 cells) performed using 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay revealed no cytotoxic effect on the tested normal cell line, demonstrating the ability to selectively kill microorganism cells with no or little damage to normal cells.Ĭonversion of Eg into polymerizable derivatives may be one solution to its unfavored properties, such as its strong odor and high volatility, for dental use. The antibacterial activity was again observed to be bacterial and substituent selective. , on the other hand, evaluated the antimicrobial and cytotoxicity characteristics of eugenol analogs prepared via acylation or alkylation methods (ester and ether products). However, many of these derivatives, ethers in particular, showed no or comparable activity compared to that of eugenol. prepared a series of eugenol derivatives, evaluated their antibacterial activity against a range of bacteria strains, and reported a derivative-dependent activity with noticeably high, broad-spectrum antibacterial activity of eugenyl p-bromobenzoate. Various derivatives of eugenol, targeting its hydroxyl functional group as a reacting site for production of, for example, esters or ethers with different substituents, have been prepared, and their properties, including antimicrobial and cytotoxicity, have been documented. Such potential properties may encourage further investigations on term of EgGMA amount optimization, compatibility with other dental resins, and antimicrobial activity. Thus, even though its apparent negative effect on polymerization, EgGMA is potentially safer than bisphenol-derived monomers. No significant difference was counted between TBEg2.5 and TBEg5, however, both differed significantly from the control (TBEg0). The cell viability test indicated that all the composites are biocompatible. The results revealed no significant difference in DC between TBEg2.5 (66.49%) and control (TBEg0 68.74%), whereas both differ significantly with TBEg5, likely due to the inhibitory effect of eugenol moiety at high concentration. The obtained data were statistically analyzed using ANOVA and Tukey post-hoc tests. The vinylic double-bond conversion (DC) after light-curing was studied using Fourier transform infrared technique whereas cell viability was in vitro tested using primary human gingival fibroblasts cells over 7 days by means of AlamarBlue colorimetric assay. The target model composites (TBEg0, TBEg2.5, and TBEg5) were prepared by mixing 35% organic matrix (TEGDMA/BisGMA (50/50 wt%) of which 0, 2.5, and 5 wt%, respectively, were replaced with EgGMA monomer) with 65% filler (silanized hydroxyapatite (HA)/zinc oxide (ZnO 2), 4:3 by weight). The aim of this study was to evaluate the properties of new dental formulations containing eugenyl-2-hydroxypropyl methacrylate (EgGMA) monomer, as restorative dental material, in terms of their degree of photopolymerization and cytotoxicity.
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