title: Cytotoxic effects of acrylates and methacrylates: relationships of monomer structures and cytotoxicity.
abstract: Thirty-nine acrylates and methacrylates that had been used in dental resin materials were evaluated by a cytotoxicity test, and the relationships between their structures and cytotoxicity were studied to predict cytotoxic levels of dental resin materials in order to develop new low-toxic resin materials. All the acrylates evaluated were more toxic than corresponding methacrylates. In both the acrylates and methacrylates, a hydroxyl group seemed to enhance cytotoxicity. Dimethacrylates with 14 or fewer oxyethylene chains showed similar cytotoxicity while dimethacrylates with 23 oxyethylene chains showed lower cytotoxicity. The cytotoxicity ranking of monomers widely used in dental resin materials was bisphenol A bis 2-hydroxypropyl methacrylate (bisGMA) > urethane dimethacrylate (UDMA) > triethyleneglycol dimethacrylate (3G) > 2-hydroxyethyl methacrylate (HEMA) > methyl methacrylate (MMA). In acrylates, methacrylates, and ethylmethacrylates with either substituents, the lipophilicity of substituents affected their cytotoxicity, and an inverse correlation between IC50 and logP was observed. These results will be useful in developing new resin materials with low toxic monomer compositions.
authors.affiliation: Department of Biomaterials Science, Faculty of Dentistry, Tokyo Medical and Dental University, Japan.
authors.forename: E
authors.initials: E
authors.lastname: Yoshii
mesh_terms: D000179:Acrylates / Q000737:chemistry / Q000633:toxicity*; D001672:Biocompatible Materials / Q000737:chemistry / Q000633:toxicity*; D003764:Dental Materials / Q000737:chemistry / Q000633:toxicity; D006367:HeLa Cells; D006801:Humans; D008422:Materials Testing; D008689:Methacrylates / Q000737:chemistry / Q000633:toxicity*; D012117:Resins, Synthetic / Q000737:chemistry / Q000633:toxicity; D013329:Structure-Activity Relationship
chemical_list: D000179:Acrylates; D001672:Biocompatible Materials; D003764:Dental Materials; D008689:Methacrylates; D012117:Resins, Synthetic