SEARCH · PubMed Health

Results for “Methacrylates”

Explore indexed PubMed citations for clinical trials, systematic reviews and public health research. Read source abstracts and follow each citation to its original PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 271 records · Page 15Linked to original sources

PubMed2006

Alterations of energy metabolism and glutathione levels of HL-60 cells induced by methacrylates present in composite resins.

OBJECTIVES: Methacrylic compounds such as 2-hydroxyethyl methacrylate (HEMA), triethylene glycol dimethacrylate (TEGDMA) and bisphenol A glycerolate (1 glycerol/phenol) dimethacrylate (Bis-GMA) are largely present in auto- or photopolymerizable composite resins. Since the polymerization reaction is never complete, these molecules are released into the oral cavity tissues and biological fluids where they could cause local adverse effects. The aim of this work was to verify the hypothesis that the biological effects of HEMA, TEGDMA and Bis-GMA - at a non-cytotoxic concentration - depend on the interaction with mitochondria and exert consequent alterations of energy metabolism, GSH levels and the related pathways in human promyelocytic cell line (HL-60). METHODS: The biological effects of methacrylic monomers were determined by analyzing the following parameters: GSH concentration, glucose-6-phosphate dehydrogenase (G6PDH) and glutathione reductase (GR) activity, oxygen and glucose consumption and lactate production along with cell differentiation and proliferation. RESULTS: All monomers induced both cellular differentiation and decrease in oxygen consumption. Cells treated with TEGDMA and Bis-GMA showed a significant enhancement of glucose consumption and lactate production. TEGDMA and HEMA induced GSH depletion stimulating G6PDH and GR activity. CONCLUSIONS: All the monomers under study affect the metabolism of HL-60 cells and show differentiating activity. Since alterations in cellular metabolism occurred at compound concentrations well below cytotoxic levels, the changes in energy metabolism and glutathione redox balance could be considered as potential mechanisms for inducing clinical and sub-clinical adverse effects and thus providing useful parameters when testing biocompatibility of dental materials.

Bisphenol A-Glycidyl Methacrylate↗

PubMed2003

Histology of anterior capsule opacification with a polyHEMA/HOHEXMA hydrophilic hydrogel intraocular lens compared to poly(methyl methacrylate), silicone, and acrylic lenses.

To evaluate the biocompatibility of various materials including a poly(2-hydroxyethyl methacrylate [HEMA])/(6-hydroxyhexyl methacrylate [HOHEXMA]) hydrophilic hydrogel intraocular lens (IOL) (Hydroview, Bausch & Lomb). Department of Ophthalmology, Wakayama Medical University, Wakayama, Japan. Ten opacified anterior capsules were extracted, including 3 specimens with the Hydroview IOL. They were processed for light and electron microscopy. Immunohistochemistry for alpha-smooth muscle actin (alpha SMA) and collagen types was also done to evaluate mesenchymal transition in lens epithelial cells (LECs). Anterior capsule opacification (ACO) in the 3 specimens with a polyHEMA/HOHEXMA hydrogel IOL contained more LECs and less extracellular matrix (ECM) than in the specimens with IOLs of other materials. Ultrastructural observation showed a well-organized collagenous ECM in tissues with an IOL of poly(methyl methacrylate), silicone, or soft acrylic material; an immature matrix was seen in specimens with a hydrogel IOL. The alpha SMA-positive LECs and collagen I and III, both types related to capsular wound healing, were detected in ACO.A polyHEMA/HOHEXMA hydrogel IOL facilitated the proliferation of LECs on the anterior capsule compared with other IOLs of other materials but did not completely suppress mesenchymal transition of LECs. Extracellular matrix accumulation appeared immature and less with a polyHEMA/HOHEXMA hydrogel IOL.

Acrylic Resins↗

PubMedDate not supplied

Synthesis and hydration properties of pH-sensitive p(HEMA)-based hydrogels containing 3-(trimethoxysilyl)propyl methacrylate.

An amphiphilic hydrogel network was synthesized from a cross-linked poly(2-hydroxyethyl methacrylate) backbone copolymerized with the monomers 3-(trimethoxysilyl)propyl methacrylate (PMA) and dimethylaminoethyl methacrylate (DMAEMA) using tetraethylene glycol diacrylate (TEGDA) as cross-linker and using the radical initiator system comprising N,N,N',N'-tetramethylethylenediamine and ammonium peroxydisulfate. The degree of hydration of hydrogel slabs was investigated as functions of varying monomer compositions and cross-link density and as a function of pH and ionic strength of the bathing medium. As much as a 45% increase in hydration was observed for hydrogels containing 15 mol % DMAEMA upon reducing the pH of the bathing medium from 8.0 to 2.0. This confirms the pH-modulated swelling of amine-containing hydrogels. Increasing the concentration of TEGDA cross-linker from 3 to 12 mol % in a 10 mol % DMAEMA-containing hydrogel resulted in only a 10% reduction in the degree of hydration of the gel. There was, however, a 40-50% reduction in the degree of hydration of a 15 mol % DMAEMA hydrogel upon increasing the molar composition of PMA from 0 up to 20 mol %. The presence of PMA confers hydrophobic character that reduces hydration and introduces additional cross-links that reduce network mesh size. The water content of the hydrogel was consistently higher in buffers of lower ionic strength. The reversible pH-dependent swelling observed in these studies, along with the control of cross-link density afforded by the PMA component, endows these biocompatible materials with potential for use in pH-controlled drug delivery of more hydrophobic drugs and present new compositions for in vitro and in vivo biocompatibility studies.

Acrylates↗

PubMed1998

The modulation of cellular responses to poly(2-hydroxyethyl methacrylate) hydrogel surfaces: phosphorylation decreases macrophage collagenase production in vitro.

We examined the regulation of collagenase production by the monocyte/macrophage THP-1 cell line when these cells were exposed to poly(2-hydroxyethyl methacrylate) (PHEMA) hydrogel surfaces with different chemistries and morphologies. Tissue culture modified polystyrene (TCP), used as a control surface, induced the maximum collagenase response. Copolymer hydrogels containing 2-ethoxyethyl methacrylate (EMA) or methyl methacrylate (MMA) also induced a high response, while PHEMA hydrogels induced a low level response and the phosphorylated hydrogel induced no response. This pattern was altered when the morphology of the hydrogels was changed to that of a sponge. The overall enzyme response to the sponge hydrogels was lower than that to the homogeneous hydrogels. Sponges containing EMA and MMA produced low level response relative to the TCP control. PHEMA and phosphorylated sponges produced little and no response respectively. The dramatically reduced enzyme response to phosphorylated surfaces was not a consequence of cell death, and may be a phenomenon related to changes in cell surface charge.

Biocompatible Materials↗

PubMed1991

Changes in 1H-NMR chemical shifts of Bis-GMA and its related methacrylates induced by their interaction with phosphatidylcholine/cholesterol liposomes.

To clarify the hemolytic mechanism of Bis-GMA and its related methacrylates, the interaction of five methacrylates (Bis-GMA, MMA, NPGDMA, TEGDMA, and UDMA) with DPPC/Cholesterol (CS) liposomes, as a model for erythrocyte membranes, was studied by 1H-NMR spectroscopy. Exogenous Bis-GMA partitioning into the DPPC/CS liposomes caused disappearances of its proton signals. With NPGDMA, its signals broadened markedly in DPPC/CS liposomes. UDMA partitioning caused changes in chemical shifts to a higher field, whereas MMA and TEGDMA partitioning did not cause any changes in chemical shifts. It was concluded from these observations that Bis-GMA has a stronger interaction with the DPPC/CS liposomes than the other methacrylates used. The high hemolytic activity of Bis-GMA reported previously seemed to be due to its migration into the lipid bilayer of phospholipids containing CS in erythrocyte membranes.

1,2-Dipalmitoylphosphatidylcholine↗

PubMed1997

Basic study of a new denture base resin applying hydrophobic methacrylate monomer.

To improve the water sorption of poly(methyl methacrylate), new hydrophobic monomers, such as norbonyl and phenyl methacrylate, were studied to determine the resin with lower water sorption with no decrease in mechanical property. Water sorption of the copolymers of the hydrophobic monomers and MMA decreased with the increase in the concentration of the monomers. Compressive and bending strength of the copolymers were higher than that of PMMA, and the elastic modulus in bending was the same as that of PMMA. In addition, the transverse-deflection values satisfied ADA specifications. Dynamic mechanical thermal analysis of the copolymers showed a similar tendency to that of PMMA in spite of the introduction of bulky groups, such as norbonyl and phenyl, in the polymer molecule. The polymerization shrinkage in volume was in the following order: norbonyl < phenyl < methyl methacrylate.

Compressive Strength↗

PubMed2001

The stability of methacrylate biomaterials when enzyme challenged: kinetic and systematic evaluations.

This study addressed whether methacrylate monomers and polymers used in dentistry might degrade from enzymolysis by acetylcholinesterase (ACHE), cholesterol esterase (CHE), porcine liver esterase (PRLE), and a pancreatic lipase (PNL). Short (hour) and long-term (day) exposures were performed. Product ratios were used to determine surface hydrolysis of the polymeric materials. Enzyme kinetics were studied for the monomers when challenged by ACHE, CHE, and PRLE. In the case of PRLE, the V(max) for the dimethacrylate substrates varied slightly, but amounted to as much as 10% of that of p-nitrophenylacetate. The K(m) for triethylene glycol dimethacrylate (TEGDMA) was 197 microM for ACHE and 1107 microM for CHE. The V(max) was 2.7 nmol/min for ACHE and 3.5 nmol/min for CHE. TEGDMA was converted by CHE at 2% the rate of cholesteryl oleate. Long-term incubations of monomers with CHE and ACHE produced degrees of hydrolysis that evidenced structure dependency in the ability of the enzymes to effect hydrolysis. Particularly resistant were aromativ derivatives and those with branching in methacrylate linkages. Overall, the study confirms the ability of physiologically important esterases to catalyze the hydrolysis of biomaterial methacrylates.

Acetylcholinesterase↗

PubMedDate not supplied

Alteration of monocytic cell oxidative burst caused by methacrylic monomers present in dental materials: a chemiluminescence study.

Methacrylates are present in dental composite resins used in clinical practice. Methacrylates are photo-polymerized, but this reaction is never complete, so release of uncured monomers in the periapical tissues and in biological fluids may happen and, potentially, alter the repair of pulpal and of periapical lesions by interfering with local phagocytes. The aim of this study was the evaluation of the functional activity of the monocyte-macrophage system after incubation with methacrylic monomers. The oxidative burst of two cellular systems was analysed using the chemiluminescence technique. Data were collected and statistically analysed. Monomers were found to reduce the in vitro oxidative burst of phagocytes independently from their cytotoxicity. These findings demand further evaluation of the effects of oxidative burst alteration in monocyte-macrophage function and may prompt the inclusion of the described chemiluminescence test in biocompatibility preliminary studies of dental materials.

Cell Survival↗

PubMed1975

An ultrastructural study of the biocompatibility of poly(2-hydroxyethyl methacrylate) in bone.

Because of the unique properties for swelling in a fluid medium and variable modulus of elasticity, hydrophilic methacrylates may be of potential usefulness for implanting prosthetic devices in bone. To investigate the biocompatibility, electron micrographic studies were done on specimens of poly(2-hydroxyethyl methacrylate) imbedded in bone for varying periods of time. Ultrastructural examination revealed progressive ossification of surrounding connective tissue up to the tissue polymer junction over a 6 month period. There was no evidence of inflammatory response. Based upon this study, it would appear that bone adjusts to an implant of hydrophilic methacrylate by ossification to the implant junction. This supports continued studies into the usefulness of this material as an implant.

Acrylates↗

PubMed1981

Determination of partition coefficients of acrylates, methacrylates, and vinyl monomers using high performance liquid chromatography (HPLC).

Retention times (Rt) for acrylates, methacrylates, and vinyl monomers were measured with two different columns (C18 Corasil and C8 LiChrosorb) using reverse-phase HPLC in order to obtain their partition coefficients between 1-octanol and water (log P). The log P values of test compounds were determined from the regression curves between RT and log P values of a number of standards using C8 LiChrosorb. The log P values obtained in this manner agreed closely with the log P values observed in previous studies. However, the peaks of these compounds were not sharp and some compounds were eluted for more than 10 min. Thus, the measurement of accurate Rt values is tedious. C18 Corasil was therefore used for this experiment in a mobile phase (methanol : water = 85 : 15). The Rt of some methacrylates with P values over 4 were delayed due to the hydrophobic interaction between these compounds and the C18 packing material. However, in the measurable region of the log P values (about -1 to +4), log P correlated linearly with log Rt following two different regression curves: one for aliphatic and aromatic compounds with the functional groups (r = 0.92), and the other for compounds without these groups (r = 0.99). It is concluded that log P values of methacrylates widely used in dentistry can be determined easily and accurately by HPLC.

1-Octanol↗

PubMed1986

Adhesion of coagulase-negative staphylococci to methacrylate polymers and copolymers.

Adhesion of coagulase-negative staphylococci (CNS) was studied onto a homologous series of methacrylate polymers and copolymers. The materials varied in wettability (contact angles) and were either positively or negatively charged (zeta-potential). Bacterial adhesion experiments performed in a parallel-plate perfusion system showed that positively charged TMAEMA-Cl copolymers significantly promoted the adhesion of CNS as compared with all other methacrylate (co)polymers tested. The bacterial adhesion rates onto the positively charged surfaces are diffusion-controlled, whereas those onto the surfaces with a negative zeta-potential are more surface-reaction-controlled due to the presence of a potential energy barrier. The bacterial adhesion rates onto various poly (alkyl methacrylates) were similar. The number of adhering bacteria onto the negatively charged MMA/MAA copolymer did not differ from that onto pMMA, indicating that sufficient sites on the copolymer surface with the same potential energy barrier as that on pMMA, were available for adhesion. Decreasing rates of adhesion of CNS were observed onto MMA/HEMA copolymers with increasing HEMA content coinciding with increasing hydrophilicity. Low plateau values for the bacterial adhesion were observed on 50MMA/50HEMA, pHEMA, and 85HEMA/15MAA, indicating that the adhesion onto these materials was reversible. Four CNS strains with different surface characteristics all showed higher numbers of adhering bacteria onto 85MMA/15TMAEMA-Cl than onto 85MMA/15MAA and pMMA.

Binding Sites↗

PubMed2001

Induction of tolerance and cross-tolerance to methacrylate contact sensitizers.

Induction of immunological tolerance to contact allergens might prevent undesired sensitization, in particular to occupational sensitizers, e.g., methacrylates (MA). Here, using a guinea pig model, we studied to which extent tolerance to one methacrylate might result in cross-tolerance to other congeners. Strong tolerance to the monomethacrylates hydroxy-ethyl MA (HEMA) and methyl MA, but not to the dimethacrylate ethylene-glycol MA (EGDMA) could be induced. The induced tolerance was stable, could not be broken by repeated sensitization attempts, and was mediated by specific suppressor cells, as demonstrated in T cell transfer experiments. In HEMA-tolerized animals, strong cross-tolerance to methacrylate congeners, including EGDMA, itself being nontolerogenic and showing the lowest cross-reactivity to HEMA, was found. Thus, oral application of contact allergens, to which skin contact cannot be avoided, e.g., in occupational settings, can induce broad cross-tolerance to related substances and might offer a promising preventive approach.

Allergens↗

PubMed1978

Methacrylate-embedded bone marrow particle histology.

Histological sections of methacrylate-embedded bone marrow biopsies allow exact evaluation and classification of the cellular marrow components. We describe a simple method for preparation of sections of aspirated bone marrow particles following embedment in methacrylate. Comparison of histological sections from marrow particles and marrow biopsies demonstrated identical quality. Thus, preparation of methacrylate-embedded particle histologies will frequently abrogate the need for marrow biopsies performed in addition to a marrow aspiration. Routine preparation of both cytological and histological preparations from aspirated bone marrow allows more exact assessment of the bone marrow than cytological evaluation only.

Acrylates↗

PubMed2006

Macroporous hydrogels based on 2-hydroxyethyl methacrylate. Part 5: hydrolytically degradable materials.

Macroporous hydrogels based on 2-hydroxyethyl methacrylate, 2-ethoxyethyl methacrylate and N-(2-hydroxypropyl)methacrylamide, methacrylic acid and [2-(methacryloyloxy)ethyl]trimethylammonium chloride crosslinked with N,O-dimethacryloylhydroxylamine were prepared. Hydrogels were degraded in a buffer of pH 7.4. Completely water-soluble polymers were obtained over time periods ranging from 2 to 40 days. The process of degradation was followed gravimetrically and by optical and electron microscopy. In vivo biological tests with hydrogels based on copolymers of 2-ethoxyethyl methacrylate/N-(2-hydroxypropyl)methacrylamide were performed.

Absorbable Implants↗

PubMed1989

Dynamic mechanical thermal analysis of dental polymers. III. Heterocyclic methacrylates.

Four heterocyclic methacrylates were investigated with respect to their loss tangent and activation energy using a dynamic mechanical thermal analyser over a limited frequency range of 0.033 to 90 Hz. The linear regression lines obtained showed an Arrhenius-type relationship between transition temperature and frequency. Their low activation energies in comparison to poly(methyl methacrylate) and bis-phenol A based methacrylates was thought to be a direct consequence of their low molecular weights.

Acrylates↗

PubMed1990

Dynamic and equilibrium swelling behaviour of pH-sensitive hydrogels containing 2-hydroxyethyl methacrylate.

The equilibrium and dynamic swelling behaviour of hydrogels containing methacrylic acid or various acrylamides was studied as a function of copolymer composition. In all cases, the comonomer was 2-hydroxyethyl methacrylate, methyl methacrylate or N-vinyl-2-pyrrolidone. It is shown that pH-sensitive behaviour with a wide range of swelling ratios could be obtained using a range of compositional changes. The dynamic swelling behaviour was a function of the acidity of the buffered solution.

Buffers↗

PubMed1991

Heterocyclic methacrylates for clinical applications. II. Room temperature polymerizing systems for potential clinical use.

A number of useful room temperature polymerizing resins were formulated, based on poly(ethyl methacrylate) powder and a range of low shrinkage heterocyclic methacrylate monomers. N,N-dimethyl-p-toluidine or p-tolyl diethanolamine were used as activating amines, but the latter material is less active and some care is necessary with respect to the source of the monomer. Isobornyl methacrylate is a useful diluent monomer to reduce the exotherm.

Biocompatible Materials↗

PubMed1992

Refractive index and molar refraction of methacrylate monomers and polymers.

The refractive indices of a number of methacrylate monomers have been measured and corresponding molar refraction data calculated. Similar determinations were made on a number of methacrylate polymers. The molar refraction values determined were in excellent agreement with the values calculated from the published molar refraction values of the chemical groups involved. There was little difference between the molar refraction values of monomers and that of the repeat unit in the corresponding polymers, in marked contrast to the molar volumes. The ratio of refractive index to molar volume was reasonably consistent for all methacrylates studied (0.25-0.30 approximately).

Chemical Phenomena↗