Effects of three resin monomers on the cellular glutathione concentration of cultured human gingival fibroblasts

Volk, Joachim; Engelmann, J; Leyhausen, Gabriele; Geurtsen, Werner

doi:10.1016/j.dental.2005.06.002

Cited by 98 publications

(80 citation statements)

References 46 publications

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“…It has been found in previous studies that TEGMA depletes intracellular GSH and interferes with cellular metabolism 9,28) . This is chiefly because the hydrolysis of TEGDMA produces triethylene glycol and methacrylic acid, and triethylene glycol might have exhibited reactivity toward GSH.…”

Section: Discussionmentioning

confidence: 99%

“…Besides, methacrylates with α, β-unsaturated carbonyl structures have been reported to possess allergenic properties due to their depletion of GSH 8) . In dentistry, the toxicity of triethylene glycol dimethacrylate (TEGDMA) has been shown to be related to its Received Jun 9, 2009: Accepted Jul 24, 2009 GSH 4,9) reactivity with , resulting in almost total depletion of intracellular GSH via Michael addition predominantly 9) . According to spectral data, the reactivity of methacrylate monomers in polymerization and copolymerization reactions usually depends on the electron density on the double bond, particularly on the β-carbon.…”

Section: Introductionmentioning

confidence: 99%

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Prediction of the reduced glutathione (GSH) reactivity of dental methacrylate monomers using NMR spectra-Relationship between toxicity and GSH reactivity

Fujisawa

Kadoma

2009

Dent. Mater. J.

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It has been established that the toxicity of acrylate and methacrylate monomers is driven by their reactivity towards glutathione (GSH). With this relationship, the objective of this study was to predict the GSH reactivity of dental methacrylate monomers, and hence their toxicity, using the 13 C-NMR chemical shifts of β-carbon (δCβ) and the 1 H-NMR shifts of the protons attached to β-carbon (δHa, δHb). The different nucleophiles were chosen to compare the different nucleophilic reactions involving acrylate and methacrylate monomers. In conjunction with the use of literature data for monomer/GSH reactivity, significant linear relationships between GSH reactivity (log K) and δCβ or δHa were observed (p<0.001). As for the oral LD50 values of some dental dimethacrylates in mice, they were estimated using linear regression curve fitting of GSH reactivity-toxicity response data. Results revealed an acceptable correlation between the oral LD50 values of acrylates and methacrylates and GSH reactivity (p<0.05, outlier: HEMA). In conclusion, the present findings suggested that NMR spectra might be useful for predicting the toxicity of dental methacrylates.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Prediction of the reduced glutathione (GSH) reactivity of dental methacrylate monomers using NMR spectra-Relationship between toxicity and GSH reactivity

Fujisawa

Kadoma

2009

Dent. Mater. J.

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“…1 HEMA caused GSH depletion, production of reactive oxygen species (ROS), and cell cycle arrest of dental pulp cells and gingival fibroblasts. 2,3 The adverse effects of resin monomers were limited by antioxidants, such as N-acetylcysteine (NAC). 4,5 NAC also partially suppressed induction of the micronucleus by TEGDMA and HEMA in a fibroblast cell line, suggesting that oxidative stress mediated the mutagenicity of the resin monomers.…”

Section: Introductionmentioning

confidence: 99%

Effects of N‐acetylcysteine on TEGDMA‐ and HEMA‐induced suppression of osteogenic differentiation of human osteosarcoma MG63 cells

et al. 2011

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Triethyleneglycol dimethacrylate (TEGDMA) and 2-hydroxyethyl methacrylate (HEMA) are major resinous components of dental restorative materials and dentin bonding adhesives. Resin monomers are known to cause cytotoxicity in mammalian cells via oxidative stress and inhibit differentiation of dental pulp cells and osteoblasts. This study was aimed to investigate whether oxidative stress was involved in the inhibition of TEGDMA- and HEMA-induced differentiation. TEGDMA and HEMA reduced alkaline phosphatase (ALP) activity and the mRNA expression of the osteopontin (OPN) gene in MG63 cells at noncytotoxic concentrations. On the other hand, N-acetylcysteine (NAC) did not affect ALP activity at concentrations below 10 mM. Reduced ALP activity and OPN mRNA expression by TEGDMA were partially recovered via cotreatment with NAC. However, NAC did not exhibit significant effects in HEMA-treated cells. Glutathione (GSH) levels were also down-regulated by both TEGDMA and HEMA. The addition of NAC induced the partial recovery of GSH in cells treated with 0.5 mM TEGDMA. On the other hand, the levels of GSH in HEMA-treated cells were not affected by NAC. These results suggest that oxidative stress is involved in the suppression of differentiation by TEGDMA. Translocation of Nrf2 from the cytoplasm to the nucleus has been known to play a role in the suppression of osteogenic differentiation by oxidative stress. However, Nrf2 did not move into the nucleus in resin monomer-treated MG63 cells, suggesting the contribution of other signaling pathways to the suppressive effects of resin monomers.

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“…The GSH reactivity for the dimethacrylates, EGDMA and TEGDMA, was like that for HEMA. TEGDMA lessens intracellular GSH levels and influences cell digestion at various levels [9,28]. It is outstanding that triethylene glycol and methacrylic corrosive are results of TEGDMA hydrolysis.…”

Section: Toxic Intermediates Of Monomers In Different Metabolic Transmentioning

confidence: 99%

“…Additionally, (meth)acylates with ,-unsaturated carbonyl structures have been accounted for to have allergenic properties because of their sadness of GSH [8]. In dentistry, the poisonous quality of triethyleneglycol dimethacrylate (TEGDMA) has been appeared to be identified with its reactivity with GSH [4,9], bringing about practically add up to consumption of intracellular GSH levels, transcendently through Michael option [9].…”

Section: Introductionmentioning

confidence: 99%

Relationships between the Reduced Glutathione (GSH) Reactivity of Dental Methacrylates, Michael-reaction Acceptors and their 13C-NMR Chemical Shift of -Carbons

Fujisawa¹

2017

Periodon Prosthodon

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Abstract(Meth)acrylates, α,β-unsaturated esters are Michaelresponse acceptors and have concentrated on antagonistic wellbeing exercises, for example, oral sicknesses and hypersensitive contact dermatitis. A connection between decreased glutathione (GSH) reactivity and lethality for (meth)acrylate monomers has been set up. To foresee the GSH reactivity of dental methacrylate monomers, the 13 C-NMR compound movements of β-carbon (δ Cβ) and the 1 H-NMR movements of the proton joined to the β-carbon (δ H a , δ H b ) were decided for a preparation set of acrylate and methacrylate monomers having diverse nucleophiles. Writing information for monomer GSH reactivity were utilized for expectation of the GSH reactivity of dental methacrylates. Critical direct connections between GSH reactivity (log K) and δ Cβ or δ Ha were watched (p<0.001). A worthy relationship for the LD 50 in mice of acrylates and methacrylates was seen as far as log K (p<0.005, exception: HEMA). The oral mouse LD 50 values for some dental dimethacrylates, two Michael-response acceptors (two-twofold bonds, two β-carbons) were assessed by direct relapse bend fitting of GSH reactivityharmfulness reaction information. The present discoveries propose that NMR spectra may be helpful for anticipating the danger of dental methacrylates.

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Effects of three resin monomers on the cellular glutathione concentration of cultured human gingival fibroblasts

Cited by 98 publications

References 46 publications

Prediction of the reduced glutathione (GSH) reactivity of dental methacrylate monomers using NMR spectra-Relationship between toxicity and GSH reactivity

Prediction of the reduced glutathione (GSH) reactivity of dental methacrylate monomers using NMR spectra-Relationship between toxicity and GSH reactivity

Effects of N‐acetylcysteine on TEGDMA‐ and HEMA‐induced suppression of osteogenic differentiation of human osteosarcoma MG63 cells

Relationships between the Reduced Glutathione (GSH) Reactivity of Dental Methacrylates, Michael-reaction Acceptors and their 13C-NMR Chemical Shift of -Carbons

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