Cytotoxic effects of acrylates and methacrylates: Relationships of monomer structures and cytotoxicity

Yoshii, Eiichi

doi:10.1002/(sici)1097-4636(19971215)37:4<517::aid-jbm10>3.3.co;2-o

Cited by 90 publications

(120 citation statements)

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“…Cell growth inhibition tests are commonly used as a measure of toxicity, where previous studies have shown that ester acrylate modified PVA displayed minimal growth inhibition of L929 cells, and that the modification resulted in only slight increase in the percentage growth inhibition over unmodified PVA 32. It was also reported that the levels of inhibition increased with increasing amounts of functional groups 40, 41. However, it was observed in this study that both PVA and PVA‐MA showed relatively low inhibitory effect on cell growth, and there was no difference between PVA and PVA‐MA (Figure 2).…”

Section: Resultscontrasting

confidence: 48%

The Influence of Silkworm Species on Cellular Interactions with Novel PVA/Silk Sericin Hydrogels

Lim

Kundu

Reeves

et al. 2012

Macromolecular Bioscience

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Sericin peptides and PVA are chemically modified with methacrylate groups to produce a covalent PVA/sericin hydrogel. Preservation of the sericin bioactivity following methacrylation is confirmed, and PVA/sericin hydrogels are fabricated for both B. mori and A. mylitta sericin. Cell adhesion studies confirm the preservation of sericin bioactivity post incorporation in PVA gels. PVA/A. mylitta gels are observed to facilitate cell adhesion to a significantly greater degree than PVA/B. mori gels. Overall, the incorporation of sericin does not alter the physical properties of the PVA hydrogels but does result in significantly improved cellular interaction, particularly from A. mylitta gels.

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Section: Resultscontrasting

confidence: 48%

The Influence of Silkworm Species on Cellular Interactions with Novel PVA/Silk Sericin Hydrogels

Lim

Kundu

Reeves

et al. 2012

Macromolecular Bioscience

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“…In this study, Tokuso Rebase liquid and its major component, 1,6‐HDMA, caused severe cytotoxic damage. Yoshii (22), in a study of the relationships of monomer structures and cytotoxicity, concluded that: (i) hydroxyl groups on acrylates and methacrylates seem to enhance cytotoxicity; (ii) dimethacrylates with 23 oxyethylene chains show higher cytotoxic levels than do dimethacrylates with 14 oxyethylene chains or fewer and (iii) the cytotoxic effects of monomers are correlated with the logarithm of the octanol/water partition coefficient (log P ). Because log P directly relates to lipophilicity, this supports the hypothesis that the mechanism of the action of monomers is membrane‐mediated and relatively non‐specific (23, 24).…”

Section: Discussionmentioning

confidence: 99%

“…This finding was supported by an investigation on the cytotoxic effects of six methacrylates with alkyl substituents on cell viability. The results indicated that the longer the alkyl chain the higher the cytotoxicity in methacrylates (22). The IBMA, which has a longer alkyl chain than MMA (Fig.…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic effects of dental resin liquids on primary gingival fibroblasts and periodontal ligament cells in vitro

Lai

Chen

Lee

et al. 2004

J of Oral Rehabilitation

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Cytotoxic effects of resin liquids of three in situ relining dental polymers, Alike, Kooliner, and Tokuso Rebase, and their major components, methyl methacrylate (MMA), isobutyl methacrylate (IBMA), and 1,6-hexanediol dimethacrylate (1,6-HDMA) were investigated. The concentrations of major monomers in these resin liquids were determined by high-performance liquid chromatography. Cellular viability of human gingival fibroblasts (GF) and periodontal ligament (PDL) cells were evaluated by the 3-[4,5-dimethylthiazol-2-yl]-2,5 diphenyltetrazolium bromide assay. Moreover, patterns of cell death were analysed using annexin V/propidium iodide staining with flow cytometry. The results indicated that Alike liquid contained 91.3% MMA, Kooliner liquid contained 94.5% IBMA, and Tokuso Rebase liquid contained 65.8% 1,6-HDMA. All materials examined had cytotoxic effects on GF and PDL cells in dose-dependent manners. Tokuso Rebase liquid appeared to be the most cytotoxic among the various resin liquids examined. The effects of Kooliner and Tokuso Rebase liquids may have resulted from IBMA and 1,6-HDMA, respectively. Furthermore, the majority of treated cells died from necrosis; whereas a small portion of cells died from apoptosis. In conclusion, the results demonstrated that these liquid forms of dental polymers and their major monomers cause cytotoxic reactions. The direct relining procedure that cures these materials in situ should be used cautiously.

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“…The medical research indicates that widely used TEGDMA is health uncertain and may even induce apoptosis of human dental pulp. This effect occurs immediately after the contact of the composition with human tissue just before curing as well as after a long‐term release of unreacted monomers …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Low Viscosity Dimethacrylic Resin Based on Isosorbide

Łukaszczyk

Janicki

Kożuch

et al. 2013

J of Applied Polymer Sci

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In this article, synthesis and properties of novel dimethacrylic resin (ISETDMA) based on human friendly, biobased isosorbide was described. Its potential as a possible diluting monomer for medical applications, mainly dental restorative systems was assessed. The resin was obtained in two-step synthesis including ethoxylation of isosorbide and subsequent methacrylation with methacryloyl chloride. 1 HNMR, FTIR, and electrospray ionization mass spectroscopy (ESI-MS) techniques were used to identify products. ISETDMA as well as composition with 2,2-bis[4-(2-hydroxy-3-methacryloyloxypropoxy)phenyl]propane were polymerized using UV initiator IRGACURE 651. Double bond conversion, polymerization shrinkage, water sorption, and sol fraction of resulting polymers were determined. Selected mechanical (flexural strength and modulus, Brinell hardness) and thermomechanical (dynamic mechanical analysis) properties were also investigated. Triethylene glycol dimethacrylate and 2,2-bis(4-(2-methacryloxyethyl-1-oxy)phenyl)propane based homopolymers and copolymers were prepared as reference for comparison of particular properties.

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Cytotoxic effects of acrylates and methacrylates: Relationships of monomer structures and cytotoxicity

Cited by 90 publications

References 0 publications

The Influence of Silkworm Species on Cellular Interactions with Novel PVA/Silk Sericin Hydrogels

The Influence of Silkworm Species on Cellular Interactions with Novel PVA/Silk Sericin Hydrogels

Cytotoxic effects of dental resin liquids on primary gingival fibroblasts and periodontal ligament cells in vitro

Synthesis and Characterization of Low Viscosity Dimethacrylic Resin Based on Isosorbide

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