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PubMed2000

Elution of bisphenol A from composite resin: a model experiment.

To understand the leaching characteristics of bisphenol A (BPA) from composite resins, we prepared experimental composite resins containing known amounts of BPA and examined the BPA elution from the resins in water and methanol at 37 degrees C. The concentration of BPA in each eluate was determined by high performance liquid chromatography. Cumulative BPA release was calculated and plotted against extraction time. The elution of BPA was rapid during a 6-hr period for both solvents, and then declined and continued steadily. Plots of square root of the amount of BPA leached against logarithm of extraction time produced good linear relationships from a 6-hr period thereafter. Extrapolation of the relationship enabled prediction of the amount of BPA to be leached in the long term. The present results suggested that little or no estrogenic effect due to long-term elution of BPA from commercial Bis-GMA-based resins is expected in practice.

Benzhydryl Compounds↗
PubMed2005

Synthesis and photopolymerization of low shrinkage methacrylate monomers containing bulky substituent groups.

OBJECTIVES: This study was conducted to determine whether novel photopolymerizable formulations based on dimethacrylate monomers with bulky substituent groups could provide low polymerization shrinkage without sacrifice to degree of conversion, and mechanical properties of the polymers. METHODS: Relatively high molecular weight dimethacrylate monomers were prepared from rigid bisphenol A core groups. Photopolymerization kinetics and shrinkage as well as flexural strength and glass transition temperatures were evaluated for various comonomer compositions. RESULTS: Copolymerization of the bulky monomers with TEGDMA show higher conversion but similar shrinkage compared with Bis-GMA/TEGDMA controls. The resulting polymers have suitable mechanical strength properties for potential dental restorative materials applications. When copolymerized with PEGDMA, the bulky monomers show lower shrinkage, comparable conversion, and more homogeneous polymeric network structures compared with Bis-EMA/PEGDMA systems. SIGNIFICANCE: The novel dimethacrylate monomers with reduced reactive group densities can decrease the polymerization shrinkage as anticipated, but there is no significant evidence that the bulky substituent groups have any additional effect on reducing shrinkage based on the physical interactions as polymer side chains. The bulky groups improve the double bond conversion and help maintain the mechanical properties of the resulting polymer, which would otherwise decrease rapidly due to the reduced crosslinking density. Further, it was found that bulky monomers help produce more homogeneous copolymer networks.

Benzhydryl Compounds↗
PubMed2003

Effects of 17beta-estradiol, bisphenol A and tributyltin chloride on germ cells of Caenorhabditis elegans.

Effects of a one-generation exposure to a natural estrogen, 17beta-estradiol (E2), and environmental pollutants such as bisphenol A (BPA) and tributyltin chloride (TBTCL) on the number of germ cells were investigated in the hermaphrodite Caenorhabditis elegans. The eggs of gravid adult worms isolated by alkaline hypochlorite treatment were seeded on a test chemical-containing NGM (nematode growth medium) agar plate without cholesterol. After incubation for 6 days at 16 degrees C, the germ cells of adult worms were stained with 4', 6-diamino-2-phenylindole dihydrochloride (DAPI). The staining procedure was completed within one hour and the stained germ cells were counted under a fluorescence microscope without dissection. The number of germ cells in the worms treated with E2 (10(-10)-10(-6) M) and BPA (10(-9)-10 (-5) M) was significantly increased. Maximal increases were observed at 10(-8) M E2 (156 +/- 15.3% of control) and 10(-5) M BPA (168 +/- 20.0 % of control). TBTCL (10(-9)-10(-6) M) significantly decreased the number of germ cells. The minimal decrease was observed at 10(-6) M TBTCL (30.2 +/- 3.51% of control). These results indicate that changes in the number of germ cells are a sensitive indicator of the effects of chemicals on the reproductive system. Since the method described in this paper is a novel, simple, time- and money-saving bioassay, C. elegans is an excellent model with which to determine the reproductive toxicity of chemicals including environmental pollutants.

Animals↗
PubMed1999

In vitro effect of the resin component bisphenol A on substrate adherence capacity of macrophages.

This study was design to investigate the "in vitro" effect of bisphenol A (BPA), a component of resin used in dentistry, on viability, and substrate adherence capacity of macrophages. Peritoneal macrophages were obtained from Wistar rats and resuspended in RPMI-1640 medium. Viability was determined by trypan blue exclusion. As a test of macrophage adhesion, the adherence capacity of macrophages to a plastic surface was determined and the adherence index was calculated. Assays were conducted in Eppendorf tubes for 60 min of incubation at 37 degrees C in a humidified atmosphere of 5% CO2 in air. BPA did not alter significantly macrophage viability at concentrations as high as 10(-5) M, but BPA decreased in a dose-dependent manner the adherence index of rat peritoneal macrophages. Control peritoneal macrophages showed an adherence index = 81.5 +/- 7.9%. In the presence of 10(-8) M BPA, the Al of macrophages decreased to 41.4 +/- 12.2% (p < 0.05). Higher BPA concentrations (10(-7) to 10(-5) M) also caused a significant inhibition of the adherence index. Half-maximal inhibition (IC50) was obtained at 4.92 +/- 0.39 x 10(-6) M BPA. The in vitro study shows that the resin component BPA can alter macrophage adhesion. Taking into account that adhesion is the first step in the phagocytic process of macrophages and in antigen presentation, BPA could inhibit macrophage function and modulate immune and inflammatory responses in dental pulp and periapical tissues.

Analysis of Variance↗
PubMed2006

Exposure to bisphenol A from bis-glycidyl dimethacrylate-based dental sealants.

BACKGROUND: Bisphenol A (BPA) is a common component of composites and dental sealants. The potential exists for human exposure after sealant placement. METHODS: The authors prospectively enrolled 15 men in an exposure assessment study; 14 completed the study. After placement of clinically appropriate amounts of one of two sealants, the authors measured BPA in saliva and urine samples collected at prescribed intervals after the sealants were placed. They used selective and sensitive isotope-dilution mass-spectrometry-based methods for BPA measurements, thus providing the most reliable results. RESULTS: Helioseal F (Ivoclar Vivadent, Amherst, N.Y.) leached negligible amounts of BPA. Urinary and salivary BPA levels in subjects who received these sealants were similar to baseline levels. Delton Light Cure (LC) Opaque pit-and-fissure sealant (Dentsply/Ash, York, Pa.) leached more BPA, resulting in low-level BPA exposures similar to those used in laboratory animal testing. BPA exposure after Delton LC sealant placement was significantly higher than exposure after placement of Helioseal F. Patients treated with Delton LC had significantly higher doses of BPA (110 microg) than did those treated with Helioseal F (5.5 microg) (P < .0001). CONCLUSIONS: Placement of clinically relevant amounts of Delton LC sealant resulted in low-level BPA exposure; however, exposure was negligible after placement of Helioseal F. Saliva collection after sealant placement likely reduced systemic absorption of BPA from dental sealants. Sealants should remain a useful part of routine preventive dental practice, especially those that leach negligible amounts of BPA. CLINICAL IMPLICATIONS: Dental sealants may be a point source for low-level BPA exposure at levels that show health effects in rodents. Further research is required to determine whether human exposure to BPA at these levels causes adverse effects.

Adult↗
PubMed2000

Pharmacokinetics of bisphenol A released from a dental sealant.

BACKGROUND: Limited information is available regarding potentially estrogenic bisphenol A, or BPA, released from dental sealants. This study determined the rate- and time-course of BPA released from a dental sealant (Delton Opaque Light-cure Pit and Fissure Sealant, Preventive Care/Dentsply) when applied at a dosage of 8 milligrams (one tooth) or 32 mg (8 mg on each of four teeth) to 40 healthy adults. METHODS: The authors recruited 40 healthy subjects (18 men and 22 women, 20-55 years of age) who did not have histories of pit and fissure sealant placement or composite resin restorations. The authors collected saliva (30 milliliters) and blood (7 mL) specimens from all subjects immediately before sealant placement (baseline) and at one hour, three hours, one day, three days and five days after sealant placement. They used high-pressure liquid chromatography to determine BPA (detection sensitivity 5 parts per billion, or ppb) in all specimens. RESULTS: The authors detected BPA in some saliva specimens (5.8-105.6 ppb) collected at one hour and three hours. The BPA, however, was not detectable beyond three hours or in any of the serum specimens. For the one- and three-hour saliva samples, the BPA concentration in the high-dose (32 mg) group was significantly greater than in the low-dose (8 mg) group (P < .05, Wilcoxon signed rank test). In the high-dose group, there was a significant decrease in saliva BPA concentrations from one hour to three hours (P < .01, Wilcoxon signed rank test). CONCLUSION: This study showed that BPA released orally from a dental sealant may not be absorbed or may be present in nondetectable amounts in systemic circulation. The concern about potential estrogenicity of sealant may be unfounded.

Adult↗
PubMed2003

Tunable ultraviolet laser-induced fluorescence detection of trace plastics and dissolved organic compounds in water.

We developed a tunable (220-285-nm) UV and fixed 266-nm laser-induced fluorescence (LIF) system using a spectrometer and a cooled CCD imaging detector to measure the excitation-emission matrix spectra of various compounds in water, including quinine sulfate and plastic compound bisphenol-A. The LIF instrument was used for the fast, nonspecific determination of trace amounts of dissolved organic compounds present in natural water supplies and various brand name bottled distilled water and bottled drinking water. Plastic-related compounds that leached out of plastic utensils and containers were also detected with this instrument. The sensitivity of the system was approximately 1-2 orders of magnitude better than that for a commercial system.

Journal Article↗
PubMed2004

Bisphenol-A exposure during pregnancy and lactation affects maternal behavior in rats.

In mammals, endogenous estrogens are crucial for sexual differentiation during the perinatal period, and the modulation in adulthood of many neuroendocrine and behavioral functions involved in reproduction. In rats, the estrogenic environment during pregnancy and lactation affects directly maternal behavior. This experiment was aimed to test whether the exposure to the estrogenic compound bisphenol-A (BPA; 0.040 mg/kg/die, orally) of adult female rats, from mating to weaning of the pups, could alter maternal behavior. An appropriate methodology was applied to reveal differences in the behavior of dams directed to male and female pups, testing the dams on postnatal days 3-4 and 8-9. Results show different maternal behavioral patterns towards male and female pups of control mothers, with more ano-genital licking to males than to females. Exposure of mothers to BPA modified their behavior, reducing specific components of maternal behavior, both active and passive, irrespective of the sex of pups and the period of observation. This experiment shows that maternal behavior is affected by a prolonged exposure to a low dose of BPA during pregnancy and lactation, thus suggesting an effect on neural circuits in adulthood.

Animals↗
PubMed2001

The induction of micronuclei in vitro by unpolymerized resin monomers.

Components of resin materials may damage DNA, leading to genetic alterations in mammalian cells. Here, monomers were analyzed for the induction of chromosomal aberrations indicated by micronuclei induced in V79 cells. A dose-related increase in the numbers of micronuclei was observed with triethyleneglycol dimethacrylate (TEGDMA), 2-hydroxyethyl methacrylate (HEMA), and glycidyl methacrylate (GMA). These effects were reduced, however, by a metabolically active microsomal fraction from rat liver. The very low activity of Bis-GMA and UDMA and the elevated numbers of micronuclei caused by high concentrations of methyl methacrylate and bisphenol A were associated with cytotoxicity. Our findings provide evidence for the induction of micronuclei by TEGDMA, HEMA, and GMA under physiological conditions, indicating clastogenic activity of these chemicals in vitro. Since it has been shown that TEGDMA also caused gene mutations and DNA sequence deletions in mammalian cells, the activity of this substance should be analyzed in vivo.

Acrylic Resins↗
PubMed1999

Bisphenol-A content of resin monomers and related degradation products.

Recently, it was reported that Bisphenol-A (BPA) was released from one fissure sealant (Delton) into saliva causing estrogenic activity in vitro. The aim of this study was to chemically analyze the BPA content of different fissure sealant resin monomers and their release of BPA under hydrolytic conditions. BPA content was first measured in commercially available monomers of bisphenol-A glycidyldimethacrylate (Bis-GMA), bisphenol-A dimethacrylate (Bis-DMA) and bisphenol-A diglycidylether (BADGE). Then, Bis-GMA-monomer and Bis-DMA-monomer in methanol were subjected to pH values of 0 to 11 for 30 minutes at 50 degrees C, to porcine liver esterase, and to pooled saliva for up to 24 hours. The BPA-content was determined by high-performance liquid chromatography (HPLC). Bis-GMA-monomer and BADGE-monomer from one manufacturer did not contain any detectable amounts of BPA (< or = 2 ppm); Bis-DMA and BADGE-monomer from a second manufacturer contained BPA quantities of 4-155 ppm. For Bis-GMA-monomer, no BPA could be detected under any hydrolytic conditions chosen (detection limit: < or = 1%). For Bis-DMA-monomer an increase of BPA was observed at pH 11, resulting in a conversion of approx. 100% Bis-DMA to BPA. When Bis-DMA was subjected to esterase, a conversion of 82.5% resulted after 24 h; saliva led to an 81.4% conversion of Bis-DMA after 24 h. Hence, we conclude that the results reported in the literature may be attributed to the Bis-DMA-content of the fissure sealant tested (Delton). No BPA-release is expected under physiologic conditions from fissure sealants based on Bis-GMA if pure base monomers are used.

Benzhydryl Compounds↗
PubMed1999

Time-related bisphenol-A content and estrogenic activity in saliva samples collected in relation to placement of fissure sealants.

It was recently reported that estrogenic activity was detected in saliva samples collected during 1 h after placement of one fissure sealant (Delton) and this related to Bisphenol-A (BPA) content. The aim of the present study was to determine the time-related BPA content and estrogenic activity in saliva samples collected before and after placement of two fissure sealants each with a different monomer composition. Eight healthy male volunteers with no history of prior placement of fissure sealants or composite resin fillings had four molars sealed with either Delton LC (four people) or Visio-Seal (four people). Base-line saliva samples were collected preexperimentally, in the morning when fasting. Fissure sealants were placed and saliva samples collected immediately, 1 h and 24 hs after placement of the fissure sealant. BPA was found in saliva samples collected immediately after placement of Delton LC (range 0.3-2.8 ppm). No detectable amounts of BPA were determined 1 h and 24 h after Delton treatment (detection limit < or = 0.1 ppm). In base-line samples and in all samples collected from Visio-Seal treated individuals, no BPA was detected. In a recombinant yeast cell assay, significantly increased estrogenic activity was found in saliva samples collected immediately after placement of Delton LC sealant (P < 0.05; ANOVA) whereas no statistically significant estrogenic activity was observed in the remaining groups. In conclusion, minute amounts of BPA, however considerably lower than previously reported, were detected in saliva samples collected immediately after but not 1 and 24 h(s) after placement of Delton LC fissure sealant. BPA was not detected after placement of Visio-Seal fissure sealant.

Adult↗
PubMed1999

Identification and characterization of estrogen-like components in commercial resin-based dental restorative materials.

Recently, resin-based dental restorative materials have been targeted as potential sources of xenoestrogens, specifically bisphenol A (BPA) and bisphenol A dimethacrylate (BAD), which could contribute to overall estrogen load and result in deleterious side effects. The present study used high-pressure liquid chromatography (HPLC) to analyze twenty-eight different commercially available dental resins for the presence of BPA and/or BAD. In addition, sublines of the MCF-7 human breast tumor cell line were cultured in the presence of eluates from eleven of the dental resins and assessed for proliferative responses using the sulforhodamine B assay. Only one resin, Delton II, had detectable levels of BPA or BAD that could be verified by Fourier transform infrared spectrometry. Likewise, eluates from Delton II were the only samples that elicited a significant proliferative response in two of the MCF-7 sublines tested. Therefore, we conclude that dental resins in general do not represent a significant source of BPA or BAD exposure.

Benzhydryl Compounds↗
PubMed1994

Analysis of dental adhesive systems using scanning electron microscopy.

This study used scanning electron microscopy (SEM) to evaluate the effects of various acid conditioners (etchants) on dentine surfaces. The conditioners completely removed the smear layer from dentine and opened the dentinal tubules, but some also left debris or a reaction product on the surface. The study also evaluated the resin-dentine interfaces produced by five new-generation dentine bonding systems: All-Bond 2, Amalgambond, Gluma 2000, OptiBond, and Scotchbond Multi-Purpose. All-Bond 2, Amalgambond, OptiBond, and Scotchbond Multi-Purpose formed acid-resistant hybrid layers and intra-tubular resin tags when they were applied to visibly moist dentine.

Acid Etching, Dental↗
PubMed2005

Thiol-ene oligomers as dental restorative materials.

OBJECTIVE: The aim of this work was to prereact thiol-ene monomers to create reactive thiol or vinyl (ene)-functionalized oligomers, and to investigate the use of these materials as novel dental restorative material. Investigation has focused on the application of oligomeric thiol-ene materials as dental restorative resins with lower polymerization shrinkage and polymerization stress as compared to monomeric thiol-ene systems and particularly with respect to current dimethacrylate-based systems. METHODS: Reactive thiol-functionalized oligomers were created via photopolymerization using triallyl-1,3,5-triazine-2,4,6-trione (TATATO), trimethylolpropane tris(3-mercaptopropionate) (trithiol) and pentaerythritol tetramercaptopropionate (tetrathiol). Kinetic and mechanical investigation of Bis-GMA/TEGDMA, and oligomeric and monomeric thiol-ene systems were conducted. More specifically, polymerization shrinkage and stress, polymerization kinetics, glass transition temperature, flexural strength and flexural modulus were evaluated. RESULTS: Upon evaluation, the polymerization stress of oligomeric thiol-ene systems was dramatically reduced by as much as 33% when compared with the stress exhibited by monomeric thiol-ene systems and as much as a 92% reduction in stress relative to the current dimethacrylate-based dental restorative materials. Furthermore, the flexural strength and modulus of the monomeric and oligomeric thiol-ene resins were not significantly different. SIGNIFICANCE: Oligomeric thiol-ene systems offer potential as alternative dental restorative resins due to the significant reduction in polymerization shrinkage and stress while retaining the mechanical properties of monomer-based thiol-ene resins.

3-Mercaptopropionic Acid↗
PubMed2005

Formulation and characterization of a novel fluoride-releasing dental composite.

OBJECTIVES: The aims of this study were to formulate a novel fluoride-releasing dental composite and to evaluate its mechanical properties, fluoride release and recharge capabilities, water sorption and solubility. METHODS: A fluoride-releasing dimethacrylate monomer containing a ternary zirconium fluoride chelate was synthesized. Three experimental fluoride-releasing composites were fabricated with different monomer formulas (wt.%)-(1) Control A: 40 BisGMA/40 TEDMA/20 UEDMA; (2) EXPERIMENTAL: 20 F-releasing monomer/20 BisGMA/40 TEDMA/20 UEDMA; (3) Control B: the same formula as Control A except that it contained 10 wt.% (of total monomer) tetrabutylammonium fluoride (TBAF), which had a fluoride content equivalent to EXPERIMENTAL. All three materials had the same filler content: 55 wt.% silanized fluoroaluminosilicate particles (0.8 microm) and 10 wt.% silanized fumed silica (14 nm). All materials contained 0.17 wt.% camphorquinone (CQ) as a photoinitiator and 0.69 wt.% ethyl-4-dimethylaminobenzoate (4EDMAB) as an accelerator. The materials were tested for fluoride release (for 184 days), fluoride recharge, compressive and flexure strength, water sorption and solubility. The data were analyzed using ANOVA and Tukey-HSD tests, and Kruskal-Wallis test. RESULTS: The experimental composite had significantly higher fluoride release and fluoride recharge capabilities than both Control composites. It had significantly better physical and mechanical properties than Control B. SIGNIFICANCE: The combined use of the fluoride-releasing dimethacrylate monomer and fluoride-releasing filler can provide sustained high fluoride release and recharge as well as acceptable mechanical and physical properties. Simply adding organic fluoride salt in the monomer yields composites with poor mechanical and physical properties.

4-Aminobenzoic Acid↗
PubMed2005

Investigations of step-growth thiol-ene polymerizations for novel dental restoratives.

OBJECTIVES: The goal of this work was to investigate the feasibility of formulating novel dental restorative materials that utilize a step-growth thiol-ene photopolymerization. Particularly, we are aiming to significantly reduce the polymerization shrinkage and shrinkage stress while retaining adequate physical properties as compared to current dimethacrylatre-based systems. METHODS: The thiol-ene system is composed of a 4:3 molar mixture of triallyl-1,3,5-triazine-2,4,6-trione (TATATO) and pentaerythritol tetramercaptopropionate (PETMP). The simultaneous measurement of shrinkage stress and functional group conversion was performed. Solvent extraction of unreacted monomers and dynamic mechanical analysis on the polymer networks that were formed were also studied. Flexural strength was measured for both filled and unfilled PETMP/TATATO and Bis-GMA/TEGDMA systems. RESULTS: Photopolymerization of PETMP/TATATO occurs at a much higher rate, with the maximum polymerization rate six times faster, than Bis-GMA/TEGDMA cured under the identical conditions. The results from the simultaneous measurement of shrinkage stress and conversion showed that the onset of shrinkage stress coincides with the delayed gel point conversion, which is predicted to be 41% for the 3:4 stoichiometric PETMP/TATATO resin composition. The maximum shrinkage stress developed for PETMP/TATATO was about 0.4 MPa, which was only approximately 14% of the maximum shrinkage stress of the Bis-GMA/TEGDMA system. Adequate flexural strength and flexural modulus values were obtained for both filled and unfilled PETMP/TATATO systems. SIGNIFICANCE: The dramatically reduced shrinkage stress, increased polymerization rate, significance increased functional group conversion, and decreased leachable species are all benefits for the use-of thiol-ene systems as potential dental restorative materials.

3-Mercaptopropionic Acid↗
PubMed1994

Comparison of the color stability of ten new-generation composites: an in vitro study.

OBJECTIVES: The aim of this in vitro study was to evaluate the color stability of modern light-cured composites when subjected to various physico-chemical and staining conditions. METHODS: Ten brands were evaluated including hybrids, microfine hybrids and microfilled composites. Some universal shade samples underwent only staining tests, while others were subjected to one of the following experimental conditions: thermocycling, postcuring, polishing or a 1 wk immersion in saline, prior to staining. The coloring solutions used for the staining tests were: coffee, E 110 food dye, vinegar and erythrosin. A colorimetric evaluation according to the CIE L*a*b* system was performed after experimental periods of 1 and 3 wk. RESULTS: Erythrosin caused the greatest color change for the composites tested. A reduced susceptibility to staining was observed where surfaces had been polished. Low water sorption, a high filler-resin ratio, reduced particle size and hardness, and an optimal filler-matrix coupling system were related to improved composite resistance to discoloration. SIGNIFICANCE: Resistance of modern composites to discolorations still depends on their structure and manipulation.

Absorption↗