Identification of 2,3-epoxymethacrylic acid as an intermediate in the metabolism of dental materials in human liver microsomes

Degree of conversion of nano-hybrid resin-based composites with novel and conventional matrix formulation

“…This may implicate allergic or toxic reactions possibly leading to clinical symptoms such as irritation, hypersensitivity, or inflammation of oral tissues [34,35]. Cell culture techniques have provided evidence that the epoxy-compound 2,3-epoxymethacrylic acid (2,3-EMA) has emerged from methacrylic acid as an intermediate in the metabolism of matrix monomer components such as triethylene glycol dimethacrylate (TEGDMA) which is often used as a diluting agent in dental RBCs [33,36] like for example in Premise, a material which was evaluated in this study. TEGDMA in its unreacted monomer form is relatively hydrophilic and shows greater water solubility potential than most other commonly used monomer components, so that it is more easily eluted from an RBC material in comparison to other monomers like Bis-GMA for example [37].…”

“…Ultimately, the molecular architecture of a polymer or, rather, the manner of cross-linking of the components of a polymer-based material is not directly reflected by DC, thus asking for further research on polymerization mechanisms at molecular level in order to make more precise statements about the chemical and mechanical properties and the biocompatibility of dental RBC materials. The release of leachable monomer components may induce a series of biological responses on cells influencing their metabolism and function [33]. This may implicate allergic or toxic reactions possibly leading to clinical symptoms such as irritation, hypersensitivity, or inflammation of oral tissues [34,35].…”

NAC ameliorates dental composite-induced DNA double-strand breaks and chromatin condensation

“…Former studies showed that the intracellular GSH is the primary antioxidant central to the cell response towards oxidative stress induced by dental monomers using the GSH synthesis inhibitor buthionine sulfoximine (BSO) and GSH synthesis promotor 2-oxo-4-thiazolidinecarboxylic acid (OTC) 42) . The metabolization of dental methacrylates involves the formation of toxic epoxides 12,13) . In the present study ACR was included as a marker substance, since it can be metabolized to an epoxide (glycidamide).…”

“…ROS are the major agents responsible for endogenous DNA damage, which includes oxidation products of DNA bases and DNA strand breaks 11) . Previous own studies have shown that the microsomal degradation of (co)monomers [for example 2-hydroxyethyl methacrylate (HEMA)] can lead to the formation of epoxides, like 2,3-epoxymethacrylate, which are considered highly toxic and mutagenic substances [12][13][14][15][16] . In addition, (co)monomers can form ROS during their metabolization, that may be mutagenic and genotoxic [14][15][16][17].…”

Induction of DNA double-strand breaks in primary gingival fibroblasts by exposure to dental resin composites

“…Additionally, leaching monomers/co-monomers can, diluted by saliva, enter the digestive tract [7]. After cellular absorption of monomers/co-monomers, they can form radical intermediates that can be metabolised to epoxy compounds as detected by microsome assay [8]. Epoxy intermediates have, via radical formation, the potential to attack biomolecules among which the DNA is a critical target (e.g., the N7-position of guanine) [9].…”