Use of Mathematical Models in the Study of Structure-Toxicity Relationships of Dental Compounds: I. Esters of Acrylic and Methacrylic Acids

Lawrence, W. H.; Bass, George E.; Purcell, William P.; Autian, John

doi:10.1177/00220345720510024701

Cited by 74 publications

(48 citation statements)

References 7 publications

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“…The LD 50 in mice of (met)acrylates was modestly associated to their log P [13,14]. We found that anticipated log K esteem was respectably associated to Invivo LD 50 esteem when HEMA was expelled.…”

Section: Periodontics and Prosthodonticsmentioning

confidence: 81%

“…1 H-NMR compound move information for TEGDMA, bis-GMA and UDMA [1]. Additionally, the 13 C-NMR concoction movements of EGDMA, TEGDMA and bis-GMA were resolved in CDCl 3 utilizing a JEOL ALPHA 500 NMR spectrometer [11][12][13].…”

Section: Nmr Spectramentioning

confidence: 99%

“…Creature testing LD 50 information got utilizing mice intraperitoneally infused with monomers [13]. Quickly, male pale skinned person ICR mice measuring 25 ± 5 g were utilized as the guinea pigs, and the LD 50 dosage for each compound was ascertained from the 7-day mortality.…”

Section: Gsh Reactivitymentioning

confidence: 99%

“…The GSH reactivities of acrylates and methacrylates have been measured already by a few gatherings [5,6,13] and the information (as log K) are abridged in Tables 1 and 2, individually. Michael expansion has been proposed as the instrument of the response of thiols with unsaturated carboxylic esters of (meth)acrylates [7], and the unsaturated β-carbon particle is the most presumably the site of assault.…”

Section: Predictiong Of Gsh Reactivity Using Nmr Spectramentioning

confidence: 99%

“…Table 2 1 H-NMR chemical shifts (δ H a , δ H b ), chemical shift differences between δ H a and δ H b (Δ│δ H a -δ H b │), electrophilicity ω) and rate constants for the reaction with reduced glutathione (log K4) for (meth)acrylates [11]. a : From [10]; b : From [13]; c : From [12]; d : From [6]; e: Measured in this study; # : ω values calculated using DFT/B3LYP 6-31 * in water starting from 6-31G * geometry [22]. * : Calculated using Equation 14 in Table 4.…”

Section: Compoundsmentioning

confidence: 99%

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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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Section: Periodontics and Prosthodonticsmentioning

confidence: 81%

Section: Nmr Spectramentioning

confidence: 99%

Section: Gsh Reactivitymentioning

confidence: 99%

Section: Predictiong Of Gsh Reactivity Using Nmr Spectramentioning

confidence: 99%

Section: Compoundsmentioning

confidence: 99%

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

Yoshii

1997

J. Biomed. Mater. Res.

352

188

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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.

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Cytotoxicity of 35 dental resin composite monomers/additives in permanent 3T3 and three human primary fibroblast cultures

Geurtsen

Lehmann

Spahl³

et al. 1998

J. Biomed. Mater. Res.

453

322

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It was the purpose of this investigation to determine the cytotoxic effects (ED50 concentrations) of 35 monomers or additives identified in commercial dental resin composites. Monolayers of permanent 3T3 cells and three primary human fibroblast types derived from oral tissues (gingiva, pulp, and periodontal ligament) were used as test systems. All substances were tested in concentrations ranging from 0.01 to 5.0 mM. In general, ED50 values varied from 0.06 to > 5 mM. Within the groups of co(monomers), initiators, and cointiators, severe (e.g., Bis-GMA, UDMA, DMBZ, and DMDTA) or moderate (HEMA, BEMA, CQ, DMPT, and DMAPE) cytotoxic effects could be evaluated. Within the group of reaction/decomposition products, only moderate or slight effects were found (ED50: 0.7 to > 5 mM). The inhibitor BHT, the contaminant TPSb, and the photostabilizer HMBP, however, were highly cytotoxic in all cell cultures. In addition, the ED50 values of DBPO and HMBP significantly varied (0.43-3.8 mM, respectively, and 0.44-3.07 mM) with the applied cell culture. Our comprehensive screening shows that for several of the highly cytotoxic composite components, less cytotoxic alternatives are available. Furthermore, there was no cell type identified which was consistently less or more sensitive to the toxic effects of the tested compounds than the others. Primary human periodontal ligament and pulp fibroblasts, however, were found to be more sensitive than 3T3 and gingival fibroblasts to alterations from most tested substances.

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Use of Mathematical Models in the Study of Structure-Toxicity Relationships of Dental Compounds: I. Esters of Acrylic and Methacrylic Acids

Cited by 74 publications

References 7 publications

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

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

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

Cytotoxicity of 35 dental resin composite monomers/additives in permanent 3T3 and three human primary fibroblast cultures

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