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Results for “Methacrylates”

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At least 307 records · Page 17Linked to original sources

PubMed2001

Fluorescent nanosensors for intracellular chemical analysis: decyl methacrylate liquid polymer matrix and ion-exchange-based potassium PEBBLE sensors with real-time application to viable rat C6 glioma cells.

Fluorescent spherical nanosensors, or PEBBLEs (probes encapsulated by biologically localized embedding), in the 500 nm-1 microm size range have been developed using decyl methacrylate as a matrix. A general scheme for the polymerization and introduction of sensing components creates a matrix that allows for the utilization of the highly selective ionophores used in poly(vinyl chloride) and decyl methacrylate ion-selective electrodes. We have applied these optically silent ionophores to fluorescence-based sensing by using ion-exchange and highly selective pH chromoionophores. This allows the tailoring of selective submicrometer sensors for use in intracellular measurements of important analytes for which selective enough fluorescent probes do not exist. The protocol for sensor development has been worked out for potassium sensing. It is based on the BME-44 ionophore (2-dodecyl-2-methyl-1,3-propanediylbis[N-[5'nitro(benzo-15-crown-5)-4'-yl]carbamate]). The general scheme should work for any available ionophore used in PVC or decyl methacrylate ion-selective electrodes, with minor adjustments to account for differences in ionophore charge and analyte binding constant. The reversible and highly selective sensors developed have a subsecond response time and an adjustable dynamic range. Applications to live C6 glioma cells demonstrate their utility; the intracellular potassium activity is followed in real time upon extracellular administration of kainic acid.

Animals↗

PubMed2001

Moleculary imprinted polymers with metalloporphyrin-based molecular recognition sites coassembled with methacrylic acid.

A diastereoselective molecularly imprinted polymer (MIP) for (-)-cinchonidine, PPM(CD), was prepared by the combined use of methacrylic acid and vinyl-substituted zinc(II) porphyrin as functional monomers. Compared to MIPs using only methacrylic acid or zinc porphyrin as a functional monomer, PM(CD) and PP(CD), respectively, PPM(CD) showed higher binding ability for (-)-cinchonidine in chromatographic tests using the MIP-packed columns. Scatchard analysis gave a higher association constant of PPM(CD) for (-)-cinchonidine (1.14 x 10(7) M(-1)) than those of PP(CD) (1.45 x 10(6) M(-1)) and PM(CD) (6.78 x 10(6) M(-1)). The affinity distribution of binding sites estimated by affinity spectrum analysis showed a higher percentage of high-affinity sites and a lower percentage of low-affinity sites in PPM(CD). The MIPs containing a zinc(II) porphyrin in the binding sites, PPM(CD) and PP(CD), showed fluorescence quenching according to the binding of (-)-cinchonidine, and the quenching was significant in the low-concentration range, suggesting that the high-affinity binding sites contain the porphyrin residue. The correlation of the relative fluorescence intensity against log of (-)-cinchonidine concentrations showed a linear relationship. These results revealed that the MIP having highly specific binding sites was assembled by the two functional monomers, vinyl-substituted zinc(II) porphyrin and methacrylic acid, and they cooperatively worked to yield the specific binding. In addition, the zinc(II) porphyrin-based MIPs appeared to act as fluorescence sensor selectively responded by binding events of the template molecule.

Binding Sites↗

PubMed2001

Graft copolymerization of acrylonitrile and ethyl methacrylate comonomers on cellulose using ceric ions.

The graft copolymerization of acrylonitrile and ethyl methacrylate from their binary mixtures onto cellulose has been carried out in the presence of Ce(IV) ions in acidic media at 30 +/- 0.1 degrees C. The graft copolymerization has shown an increasing trend on increasing the feed molarity of the comonomers and on increasing the reaction time. The analysis of grafted cellulose prepared with different feed compositions (f(AN)) has clearly indicated the existence of the synergistic effect of ethyl methacrylate on acrylonitrile which normally shows poor affinity for grafting on cellulose while used individually. The elemental analysis and IR data were used to determine the composition of grafted copolymers and reactivity ratios (r(1), r(2)) of the monomers using the Mayo and Lewis method. The reactivity ratios for acrylontrile and ethyl methacrylate have been found to be 0.68 and 1.15, respectively, which supported the alternate arrangement of the monomer blocks of individual monomers in the grafted chains. The rate of grafting has shown a square dependence on the concentration of the comonomers within the studied range of feed molarity from 0.5 to 2.5 mol dm(-3). The grafting data were used to calculate the number of grafted chains (N(g)), frequency of grafting (G(F)) per molecule of the cellulose and efficiency of grafting (G(E)). The variation in these parameters as a function of feed molarity, feed composition, and ceric ion concentration has been determined. The rate of ceric ion disappearance as a function of feed molarity and reaction time has provided strong support to consider the participation of ceric ions in the formation of free radicals at the backbone of the cellulose. On the basis of the experimental observations, reaction steps for grafting of monomers on cellulose have been proposed.

Acrylonitrile↗

PubMedDate not supplied

Methacrylate derivatives incorporating pyroglutamic acid.

Methacrylates containing pyroglutamic acid were synthesized in good yields. Methyl alpha-pyroglutamyl methylacrylate (PyMM) and methyl alpha-pyroglutamidoundecanoyl methylacrylate (PyUM) give very fast photopolymerization rates both in homopolymerizations and with widely used commercial monomers N-vinyl pyrrolidinone (NVP) and hydroxyethyl methacrylate (HEMA). Soluble or cross-linked homopolymers can be obtained depending upon polymerization temperature. Pyroglutamic methacrylates polymerize without added initiator in the melt. Solution cast, photocured, and thermally cured coatings gave good to excellent adhesion to poly(ethylene terephthalate) and glass surfaces.

Absorption↗

PubMedDate not supplied

Release characteristics of novel pH-sensitive p(HEMA-DMAEMA) hydrogels containing 3-(trimethoxy-silyl) propyl methacrylate.

An amphiphilic hydrogel of poly(2-hydroxyethyl methacrylate) cross-linked with tetraethyleneglycol diacrylate (TEGDA) was synthesized to contain the hydrophobic monomer 3-(trimethoxy-silyl) propyl methacrylate (PMA) and the pH-responsive, hydrophilic monomer N',N'-dimethylaminoethyl methacrylate (DMAEMA). The gels were separately loaded with two biomolecular probes, insulin and protamine, via both physical entrapment and equilibrium imbibition methods. The release profiles for these biomolecular probes, possessing similar MW (5.7 and 4-6 kDa, respectively) but different pI's (5.3 and 10.0, respectively), were investigated with respect to variation in the pH of the bathing medium as well as the DMAEMA content, and the cross-link density of the hydrogel. Gels exhibited classical Fickian diffusion release profiles. For a typical gel composition 66:15:10:09 mol % (HEMA:DMAEMA:PMA:TEGDA), as the pH of the release media decreased from 7.3 to 4.0, the rate of release of both biomolecular probes increased. When loaded via entrapment, the insulin release rate increased ca. 4-fold (1.0-3.7 x 10(-7) cm(2) s(-1)), whereas that of protamine increased 10-fold (0.3-3.3 x 10(-7) cm(2) s(-1)). When loaded by imbibition, the insulin diffusion coefficient increased 2-fold (3.8-7.2 x 10(-7) cm(2) s(-1)), whereas that of protamine increased 3-fold (1.9-5.5 x 10(-7) cm(2) s(-1)). The reduction of pH, through its protonation of the gel network, has a more dramatic influence on protamine release, the result of its higher pI (10.0) compared to that of insulin (5.3). As the DMAEMA content of the hydrogel was increased from 0 to 20 mol %, the diffusion coefficient of protamine increased by ca. 7-fold (1.7-12.2 x 10(-7) cm(2) s(-1)), whereas that of insulin increased only ca. 2-fold (1.7-4.0 x 10(-7) cm(2) s(-1)). This differential release confirms the role of internal protonation in effecting the greater release of the protonated drug molecule. Increasing the TEGDA content from 3 to 15 mol % reduced the diffusion coefficient ca. 3-fold for insulin (1.6-0.5 x 10(-7) cm(2) s(-1)) and 5-fold for protamine (4.0-0.8 x 10(-7) cm(2) s(-1)). The final D(ip) at 15 mol % TEGDA suggests that the smaller mesh size offsets any differential release that arises from protonation. The presence of PMA in the hydrogel formulation, which contributes additional cross-links by reason of the formation of siloxane macromers, did not change the usually observed Fickian diffusion mechanism.

Biocompatible Materials↗

PubMed2005

Theoretical study of the suicide inhibition mechanism of the enzyme pyruvate formate lyase by methacrylate.

The determination of pyruvate formate lyase crystallographic structure brought new insights to its mechanism of reaction and presented the possibility of a direct attack to the substrate from cysteine 418 as opposed to the previously expected cysteine 419. An inhibition study performed by Knappe and co-workers, using substrate-analogue methacrylate, confirms that cysteine 418 is most likely to add directly to pyruvate, since an inhibition product has been found as a substituent in this residue. The work presented here consists of a study of the inhibition mechanism of pyruvate formate lyase by methacrylate, using density functional theory with the hybrid B3LYP functional. We were able to determine all pertinent structures, confirm the proposed experimental mechanism, and add important detail to the energy profile associated with the mechanism of inhibition. Additionally, the obtained results provide the energy values for both the chemical reaction and the stereochemical reorganization necessary in order for the thiol-methacrylate adduct to come within reactional reach of Cys419.

Acetyltransferases↗

PubMed1998

Long-circulating nanoparticles bearing heparin or dextran covalently bound to poly(methyl methacrylate).

PURPOSE: In a biomimetic approach to the development of drug carriers escaping early capture by phagocytes, nanoparticles made of amphiphilic copolymers of either heparin or dextran and methyl methacrylate were evaluated relative to their in vivo blood circulation time. They were compared to bare PMMA nanoparticles. METHODS: Owing to the fluorescent properties of the covalently attached N-vinyl carbazole, the particles could be detected directly in mouse plasma. Samples were drawn at different time intervals and fluorescence was recorded. RESULTS: After an initial phase of elimination from the blood with a half-life of 5 h, the remaining heparin nanoparticles circulated for more than 48 h and were still detectable in the plasma at 72 h. Dextran nanoparticles were also eliminated very slowly over 48 h. Bare poly (methyl methacrylate) nanoparticles were found to have a half-life of only 3 min. CONCLUSIONS: Both types of nanoparticles proved to be long-circulating. The potent capacity for opsonisation of the poly(methyl methacrylate) core were hidden by the protective effect of either polysaccharide, probably due to a dense brush-like structure. In the case of heparin nanoparticles, the "stealth" effect was probably increased by its inhibiting properties against complement activation.

Animals↗

PubMed2003

The effect of the addition of poly(methyl methacrylate) fibres on some properties of high strength heat-cured acrylic resin denture base material.

The self-reinforcement of acrylic resin with butadiene styrene surface treated poly(methyl methacrylate) fibres has been reported to have the potential to substantially improve the transverse bend strength of conventional heat-cured acrylic resin. The aim of this study was to investigate the effect of the addition of butadiene styrene surface treated poly(methyl methacrylate) fibres in cross-ply arrangement to high impact acrylic resin on the transverse and impact strength. Specimens were prepared as specified in the International Standard Organization and British Standards for the Testing of Denture Base Resins (ISO 1567, 1988; BS 2487, 1989) and the British Standard Specification for Orthodontic resins (BS 6747, 1987) for transverse bend and impact testing. The impact strength was measured using a Zwick pendulum impact tester and the transverse bend strength measured using a Lloyds Instruments testing machine. The results showed that the impact strength was not improved with the addition of fibres, high impact acrylic resin with fibres (LF) 11.1 kJ m-2 and high impact acrylic resin (L) (12.5 kJ m-2). The modulus of rupture was decreased with the addition of fibres (57.8 MPa) for (LF) compared with (60.4 MPa) for (L). The modulus of elasticity was also reduced with the addition of fibres (1834.9 MPa) (LF) and 2086.2 MPa (L) as was the peak load (LF) (50.8 N) and (L) (55.8 N). It was concluded that the addition of surface treated poly(methyl methacrylate) fibres in cross-ply arrangement to high strength acrylic resin did not produce an improvement in the impact or transverse strength and cannot be recommended as a method of reinforcement.

Acrylic Resins↗

PubMed1962

Polyester-methacrylate embedments for electron microscopy.

It has been found that tissues fixed for electron microscopy and dehydrated in acetone can be embedded in mixtures of n-butyl methacrylate and polyester resin. Activation with 1 per cent tert-butyl hydroperoxide followed by 12 to 48 hours at 60 degrees C produces blocks that section well with glass knives. The ribbons are cleared of methacrylate by heat (200-250 degrees C for 1 hour) and/or immersion in organic solvents (CCL(4), acetone-ether). After removal of the methacrylate the residual polyester matrix provides thermostable and insoluble support for the tissue. Its insolubility permits staining by immersion of cleared preparations in organic solvents carrying heavy metal compounds in solution. Clearing by heat stabilizes section-grid relationships. The removal of volatile materials by clearing substantially reduces contamination of both specimen and microscope. Tissue fine structure is well preserved in these preparations.

Electrons↗

PubMed2004

Biomechanical analysis of anterior poly-methyl-methacrylate reconstruction following total spondylectomy for metastatic disease.

STUDY DESIGN: Three reconstruction options were evaluated biomechanically following total spondylectomy using human cadaveric spine specimens. OBJECTIVES.: To evaluate and compare the stability of combined anterior and posterior fixation incorporating poly-methyl-methacrylate with alternative accepted reconstruction techniques. SUMMARY OF BACKGROUND DATA: Total spondylectomy represents the most radical option for decompression in metastatic spinal cord compression. Poly-methyl-methacrylate is considered a useful adjunct in spinal column stabilization and arthrodesis; however, there is little published biomechanical data to support its use in this setting. METHODS: Ten fresh-frozen human cadaveric spines (T9-L3) were used. After intact analysis, a total spondylectomy was performed at T12. Three potential reconstruction techniques were tested for their ability to restore stiffness to the specimen: 1) multilevel posterior pedicle screw instrumentation from T10-L2; 2) anterior instrumentation (ATL Z plate II) and rib graft at T11-L1 with multilevel posterior pedicle screw instrumentation from T10-L2; and 3) anterior cement (Simplex P) and pins construct (T12) with multilevel posterior pedicle screw instrumentation from T10-L2. Each of the three potential reconstruction techniques was tested on each specimen in random order using nondestructive testing under load control. RESULTS: Only combined stabilization techniques (e.g., anterior instrumentation and rib graft with multilevel posterior pedicle screw instrumentation and anterior cement-and-pins construct with multilevel posterior pedicle screw instrumentation) restored stiffness to a level equivalent to or higher than that of the intact spine in all loading modes (P < 0.05). Anterior cement-and-pins construct with multilevel posterior pedicle screw instrumentation provided more stability to the specimen than anterior instrumentation and rib graft with multilevel posterior pedicle screw instrumentation in compression and flexion testing (P < 0.05). Posterior instrumentation alone did not restore stiffness to the intact level in compression and flexion testing (P < 0.005). CONCLUSIONS: Combined anterior and posterior reconstruction using a cement construct provides equal to or more stability than the intact spine in all testing modes. Posterior stabilization alone is an inferior method of reconstruction following total spondylectomy. Poly-methyl-methacrylate has the advantage over traditional anterior reconstruction techniques in that it can be inserted using a posterior approach.

Aged↗

PubMed1990

Enzymatic hydrolysis of (di)methacrylates and their polymers.

Di- and monomethacrylates hydrolyze to methacrylic acid and the alcohol part at neutral pH catalyzed by an unspecific esterase (hydrolase) and by enzymes in saliva. The rate constants of the enzymatic hydrolysis of various (di)methacrylates increase in the following order: HPMA less than BISGMA less than LAMA less than DECMA less than TEGDMA less than UEDMA less than DEGDMA. Esterase added to aqueous slurries of various powders made of polymerized BISGMA/TEGDMA-mixtures gave rise to liberation of methacrylic acid, presumably deriving from degradation of those of the dimethacrylates only bonded in the matrix by one end of the molecule. It was estimated that a TEGDMA-polymer will be hydrolyzed faster than a BISGMA-polymer. It is proposed that hydrolases in saliva increase the wear rate of composite resin fillings.

Acrylates↗

PubMed2000

Cytotoxicity of methyl methacrylate (MMA) and related compounds and their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biomembranes.

OBJECTIVE: To clarify the potential mechanism of action of methyl methacrylate (MMA) and related compounds to membranes of living cells, compared with their interaction with dipalmitoylphosphatidylcholine (DPPC) liposomes as a model for biological membranes. MATERIALS AND METHODS: For (meth)acrylates, MMA, ethyl acrylate(EA), n-butyl acrylate (BA) and n-butyl methacrylate (BMA) and for living cells, primary human gingival fibroblast (HGF), human submandibular gland adenocarcinoma cell line (HSG) and human erythrocytes were used. The physicochemical changes in DPPC liposomes induced by (meth)acrylates were studied using differential scanning calorimetry (DSC) and nuclear magnetic resonance spectroscopy (NMR). RESULTS: Cytotoxicity decreased as follows: BA > BMA > EA > MMA. Changes in phase transition properties (temperature Tm, enthalpy delta H and Height/Half-Height Width (H/HHW) of DSC peak were decreased as follows: BA > EA > MMA. BMA enhanced H/HHW and increased Tm slightly. NMR-shielding effect decreased as follows: BMA > MMA > BA, EA. CONCLUSION: BA and BMA exhibited large cytotoxicity and high DPPC-interaction due to their lipophilicity, compared to EA or MMA. MMA showed little cytotoxicity and small changes in DPPC liposomes, whereas BA showed large cytotoxicity and large changes in the liposomes characterized by the membrane disturbance. Haemolytic activity and cytotoxicity of acrylates were higher than those of methacrylates. The physico-chemical properties (Log P or Q sigma) of (meth)acrylates affect the lipid bilayer in biological membranes.

1,2-Dipalmitoylphosphatidylcholine↗

PubMed1991

Bonding efficacy of erythritol methacrylate solutions as dentin primers.

The bonding efficacy of aqueous solutions of two kinds of erythritol methacrylates as dentin primers was examined by measurement of the polymerization contraction gap of a light-activated resin composite in a cylindrical dentin cavity and the tensile bond strength of the composite to the flat dentin surface. The dentin surface was cleaned with neutralized 0.5 mol/L EDTA and pre-treated with a meso-erythritol or penta-erythritol methacrylate solution, followed by application of a commercial dentin bonding agent (Clearfil New Bond) and a resin composite. Among the tested primers, a 40% meso-erythritol methacrylate solution was shown to be the most effective because, in contrast to the other primers, contraction gap formation by the composite was prevented in all tested specimens.

Composite Resins↗

PubMed1984

Immersion fixation methods for glycol methacrylate-embedded testes.

Routine processing of testicular tissue through 10% neutral buffered formalin (NBF) into paraffin produces severe cellular shrinkage which obscures most of the morphologic detail. The following studies were performed to compare different combinations of immersion fixatives and embedding media for optimal cellular detail in the final histologic sections. We examined sections of testes from rats, mice, and rabbits fixed in either NBF, Bouin's, Zenker's, or Helly's fixatives, and embedded in either standard paraffin or glycol methacrylate. The results were similar in all 3 species. In paraffin, Bouin's or Helly's fixatives produced the fewest artifacts, while in glycol methacrylate, NBF-fixed tissue showed the greatest intracellular detail and preservation. The merits and limitations of each method are discussed for the rat, with exceptions for the other species noted where appropriate. The use of glycol methacrylate as the support medium for sectioning makes high-quality tissue sections available from formalin-fixed testes.

Acrylates↗

PubMed2004

Physicochemical, mechanical, and biological properties of bone cements prepared with functionalized methacrylates.

Bone cements prepared with methyl methacrylate (MMA) as a base monomer and either methacrylic acid (MAA) or diethyl amino ethyl methacrylate (DEAEMA) as comonomers were characterized in terms of curing behavior, mechanical properties, and their in vitro biocompatibility. The curing time and setting temperature were found to be composition dependent while the residual monomer was not greatly affected by the presence of either acidic or alkaline comonomers in the bone cements. For samples with MAA comonomer, a faster curing time and higher setting temperature were observed when compared to the cement with DEAEMA comonomer. In terms of mechanical properties, the highest compressive strength was exhibited by formulations containing MAA, while the highest impact strength was shown by the formulations prepared with DEAEMA. There were no differences observed between the two formulations for tensile, shear, and bending strength values. Similarly, fatigue crack propagation studies did not reveal differences with the addition of either DEAEMA or MAA.No differences were observed in the initial number of attached primary rat femur osteoblasts on the different bone cements and positive controls. However, after 48 h there was a reduced proliferation in the cells grown on bone cements containing MAA.

Animals↗

PubMed1977

Improvements of glycol methacrylate. I. Its use as an embedding medium for electron microscopic studies.

The technique for using the water-soluble embedding medium glycol methacrylate has been improved for ultrastructural studies by the simplification of the method of formation of prepolymers used in embedding the tissue, by the addition of a cross-linking agent so that sections are stable in the electron beam, and by improving the softness of the blocks by the addition of a plasticizing agent. The preservation of tissue morphology has been improved by complete dehydration in glycol methacrylate monomer prior to infiltration with the prepolymer. Preservations of tissue morphology is further enhanced by complete dehydration in ethanols and embedding in the improved glycol methacrylate medium.

Acrylates↗

PubMed1990

Enzyme histochemistry on freeze-substituted glycol methacrylate-embedded tissue.

We developed a method for histochemical demonstration of a wide range of enzymes in freeze-substituted glycol methacrylate-embedded tissue. Tissue specimens were freeze-substituted in acetone and then embedded at low temperature in glycol methacrylate resin. All enzymes studied (oxidoreductases, hydrolases) were readily demonstrated. The enzymes displayed high activity and were accurately localized without diffusion when tissue sections were incubated in aqueous media, addition of colloid stabilizers to the incubating media not being required. Freeze-substitution combined with low-temperature glycol methacrylate embedding permits the demonstration of a wide range of enzymes with accurate enzyme localization, maintenance of enzyme activity, and excellent tissue morphology.

Acrylates↗

PubMed2006

Preparation of surfactant-free nanoparticles of methacrylic acid copolymers used for film coating.

The aim of the present study was to prepare surfactant-free pseudolatexes of various methacrylic acid copolymers. These aqueous colloidal dispersions of polymeric materials for oral administration are intended for film coating of solid dosage forms or for direct manufacturing of nanoparticles. Nanoparticulate dispersions were produced by an emulsification-diffusion method involving the use of partially water-miscible solvents and the mutual saturation of the aqueous and organic phases prior to the emulsification in order to reduce the initial thermodynamic instability of the emulsion. Because of the self-emulsifying properties of the methacrylic acid copolymers, it was possible to prepare aqueous dispersions of colloidal size containing up to 30% wt/vol of Eudragit RL, RS, and E using 2-butanone or methyl acetate as partially water-miscible solvents, but without any surfactant. However, in the case of the cationic Eudragit E, protonation of the tertiary amine groups by acidification of the aqueous phase was necessary to improve the emulsion stability in the absence of surfactant and subsequently to prevent droplet coalescence during evaporation. In addition, a pseudolatex of Eudragit E was used to validate the coating properties of the formulation for solid dosage forms. Film-coated tablets of quinidine sulfate showed a transparent glossy continuous film that was firmly attached to the tablet. The dissolution profile of quinidine sulfate from the tablets coated with the Eudragit E pseudolatex was comparable to that of tablets coated with an acetonic solution of Eudragit E. Furthermore, both types of coating ensured similar taste masking. The emulsification-evaporation method used was shown to be appropriate for the preparation of surfactant-free colloidal dispersions of the 3 types of preformed methacrylic acid copolymers; the dispersions can subsequently be used for film coating of solid dosage forms.

Chemistry, Pharmaceutical↗