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PubMed2003

Poly(butyl methacrylate-g-methoxypoly(ethylene glycol)) and poly(methyl methacrylate-g-methoxypoly(ethylene glycol)) graft copolymers: preparation and aqueous solution properties.

A series of water-soluble, amphiphilic graft copolymers has been prepared by free-radical copolymerization of methoxypoly(ethylene glycol) macromonomers, with either methyl methacrylate or butyl methacrylate as the comonomers, in water/ethanol solvent mixtures. Lower molecular weight copolymers were obtained by increasing the concentration of the initiator, azobisisobutyronitrile (AIBN), used in the polymerization reaction. However, the route used also led to the formation of significant quantities of tetramethylsuccinodinitrile, a toxic byproduct resulting from the cage reaction of AIBN. Static fluorescence measurements using pyrene as a probe, along with 1H NMR experiments, showed that the graft copolymers form aggregates in water at very low concentrations (approximately 0.01 g l(-1)) with the pendant hydrophilic graft chains forming a stabilizing shell around the hydrophobic backbone. An increase in the hydrophile-lipophile balance of the graft copolymers was found to lead to smaller aggregates with lower aggregation numbers and highly swollen hydrophilic shells, as revealed by small angle neutron scattering (SANS).

Methacrylates↗
PubMed2003

Polystyrene nanoparticles based on poly(butyl methacrylate-g-methoxypoly(ethylene glycol)) and poly(methyl methacrylate-g-methoxypoly(ethylene glycol)) graft copolymers.

The solubilization of styrene by poly(butyl methacrylate-g-methoxypoly(ethylene glycol)) and poly(methyl methacrylate-g-methoxypoly(ethylene glycol)) graft copolymers has been examined. From turbidity measurements the solubility limit of the monomer in the micelles was obtained and the distribution coefficients were evaluated. Dynamic light scattering revealed that below the solubility limit, solubilization leads to a slight increase in micelle size, while above the solubility limit, there is a dramatic increase in particle size and turbidity as oil-in-water emulsions are formed through coalescence of monomer-swollen micelles. Polymerizations carried out below the solubility limit using the graft copolymer micelles as templates resembled microemulsion polymerizations in nature and led to very fine sterically stabilized polystyrene latex particles. Through careful control of the monomer concentration and the polymerization temperature it was possible to obtain spherical nanosize latex particles with similar size to those of the micelle precursors (10 nm) up to 11% monomer by weight. Polymerizations above the solubility limit, on the other hand, showed similarities with emulsion polymerizations and resulted in larger particles with higher polydispersity.

Emulsions↗
PubMedDate not supplied

Slow releasing of ara-C from poly(2-hydroxyethyl methacrylate) and poly(2-hydroxyethyl methacrylate-co-N-vinyl-2-pyrrolidone) hydrogels implanted subcutaneously in the back of rats.

The release of cytarabine (ara-C) from poly(2-hydroxyethyl methacrylate) and poly(2-hydroxyethyl methacrylate-co-N-vinyl-2pyrrolidone) hydrogels cross-linked with different amounts of ethyleneglycol dimethacrylate (EGDMA) 'in vivo' has been studied. Two ara-C loaded hydrogel discs, each with 25 mg of the drug, were subcutaneously implanted in the back of male Wistar rats. Total ara-C dose was 230 mg kg(-1). Ara-C and ara-U plasmatic concentration were determined by HPLC. Periods of constant drug concentration are observed from all gels. Ara-C concentrations in the steady-state are between 19.0 +/- 2.0 and 2.2 +/- 0.8 micromol l(-1). The release time of ara-C was between 3 days from pH EMA 0.5% and 16 days from H80/VP20/E15 gels. These results are very different of that obtained when ara-C is administered by intraperitoneal injection, in this case peaks of maximum concentration (between 24 +/- 1 and 3.9 +/- 0.4 microg ml(-1)) 30 min after the injection are originated, and no drug is detected 4 h after the injection.

Animals↗
PubMed1999

12 year results of a prospective trial comparing poly(methyl methacrylate) and poly(hydroxyethyl methacrylate) intraocular lenses.

PURPOSE: To compare long-term biocompatibility of single-piece poly(methyl methacrylate) (PMMA) and poly(hydroxyethyl methacrylate) (P-HEMA) intraocular lenses (IOLs). SETTING: District General Hospital, United Kingdom. METHODS: In a prospective trial of 250 eyes that had uncomplicated extracapsular cataract extraction, 2 groups of 125 eyes each were matched for age and sex. One group received single-piece looped PMMA IOLs and the other, single-piece solid-haptic P-HEMA IOLs. In all eyes, the IOLs were implanted in the capsular bag at the time of surgery using the envelope technique. RESULTS: Twelve years after surgery, 75 eyes were available for examination. In the PMMA group (40 eyes), 50% had a visual acuity of 20/20 and 50% had intact capsules, many of them with a degree of fibrosis. In the P-HEMA group (35 eyes), 71% had an acuity of 20/20 and 80% had intact capsules (P = .0085). CONCLUSION: In the long term, biocompatibility was better in the P-HEMA group than in the PMMA group.

Aged↗
PubMed2001

NMR imaging of water sorption into poly(hydroxyethyl methacrylate-co-tetrahydrofurfuryl methacrylate).

The diffusion of water into a series of hydroxyethyl methacrylate, HEMA, copolymers with tetrahydrofurfuryl methacrylate, THFMA, has been studied over a range of copolymer compositions using NMR imaging analyses. For polyHEMA the diffusion was found to be consistent with a Fickian model. The mass diffusion coefficient of water in polyHEMA at 37 degrees C was determined from the profiles of the diffusion front to be 1.5 x 10(-11) m(2) s(-1), which is less than the value based upon mass uptake, 2.0 x 10(-11) m(2) s(-1). The profiles of the water diffusion front obtained from the NMR images showed that stress was induced at the interface between the rubbery and glassy regions which led to formation of small cracks in this region of the glassy matrix of polyHEMA and its copolymers with mole fractions of HEMA greater than 0.6. Water was shown to be able to enter these cracks forming water "pools". For copolymers of HEMA and THFMA with mole fractions of HEMA less than 0.6 the absence of cracks was attributed to the ability of the THFMA sequences to undergo stress relaxation by creep.

Absorption↗
PubMed1989

The short-term blood biocompatibility of poly(hydroxyethyl methacrylate-co-methyl methacrylate) in an in vitro flow system measured by digital videomicroscopy.

An in vitro flow system for short-term blood biocompatibility testing of solution-castable polymeric biomaterials was developed. This system was relatively free of artefacts resulting from blood contact with materials other than the test material itself. In conjunction with epifluorescence videomicroscopy and digital image processing, this method provided a high resolution, quantitative, continuous analysis of platelet adhesion, aggregation, thrombus formation, and embolization on the biomaterial surface. This system was well suited for performing biochemical assays on post-contact blood for assessment of platelet activation and release as additional measures of the thrombogenicity of the test material. This method for biomaterials evaluation in vitro was demonstrated by a detailed examination of copolymers of hydroxyethyl methacrylate (HEMA) and methyl methacrylate (MMA). Videomicroscopic analysis of fluorescently labelled platelets adhering per unit area of the polymer surface after 5 min of flow at a wall shear rate of 500 s-1 showed a dramatic decrease with increasing HEMA fraction in the polymer. The release of serotonin and thromboxane A2 by platelets decreased with increasing HEMA fraction. Reflection interference contrast microscopy was used to examine focal contacts of platelets on the copolymer surfaces as a qualitative measure of the platelet-surface interaction. A polymer-dependent gradation in contact extent and morphology was observed, ranging from large contacts on P(MMA) to none on P(HEMA).

Biocompatible Materials↗
PubMed2000

Gentamicin release from hydroxyapatite/poly(ethyl methacrylate)/poly(methyl methacrylate)composites.

In this work the release kinetics of gentamicin sulfate (GEN) in samples composed by hydroxyapatite, poly(methyl methacrylate), and poly(ethyl methacrylate) has been studied. The release study was performed by soaking three samples in simulated body fluid at 37 degrees C; the medium was periodically replaced during 70 days. The concentration of GEN was determined by the o-phtaldialdehyde method. The release profile shows three stages: the first stage, occurring during the first 10 h, corresponds to a fast release (nearly 30% of the drug is released in this period). The second stage is slower and includes from the first 10 h to 16 days, releasing 60% of the total amount of GEN. The final stage is the slowest and it takes from 16 to 70 days (10% of GEN is released). The fraction of released GEN versus square root of time can be fitted to a third order polynomial, corresponding with the model proposed by Cobby et al. (J Pharm Sci 1974;63:725-732). The characterization of the samples after the release study shows that a carbonate hydroxyapatite layer has grown on the whole surface of the composites.

Animals↗
PubMedDate not supplied

Rat peritoneal macrophage adhesion to hydroxyethyl methacrylate-ethyl methacrylate copolymers and hydroxystyrene-styrene copolymers.

Macrophage adhesion to a wide variety of substrates has been measured, but no systematic study of the influence of specific substrate chemical properties on adhesion is available. These studies were conducted using two series of materials, copolymers of hydroxyethyl methacrylate (HEMA) and ethyl methacrylate (EMA) and copolymers of hydroxystyrene and styrene, to determine the effect of a single chemical property, polar character, on adhesion. Rat peritoneal macrophages were allowed to contact polymer substrates for periods ranging from 1 to 240 min before being subjected to a shear stress of 60-120 dynes/cm2 in a thin-channel flow cell. Percentage adhesion was calculated from the number of cells that remained adherent to the substrate after 30 s of applied shear stress. Macrophages remained adherent to 100% EMA and all hydroxystyrene-styrene copolymer surfaces after only 1 min of contact. In copolymers of the HEMA-EMA series, the time required to attain peak adhesion levels increased with increasing substrate hydrophilicity (increasing HEMA content). Cells did not attach to the 20% EMA/80% HEMA copolymer and the 100% HEMA polymer. The results demonstrate that there is a time delay between contact and adhesion of the cells to surfaces of increasing hydrophilicity within the HEMA-EMA series and no time delay with the hydroxystyrene-styrene series. The time delay is thought to be a function of the excluded volume provided by polymers that are able to undergo significant chain rotation and or swelling in the solvent, water. Small excluded volumes present in copolymers of high EMA content and all hydroxystyrene-styrene copolymers offer little or no resistance to formation of adhesive bonds by macrophages, whereas copolymers with large excluded volumes (high HEMA content) prevent contact and/or adhesion. A mechanism based on the net excluded volumes of both the cell and substrate surface macromolecule is proposed to explain this phenomenon.

Animals↗
PubMed1991

Platelet adherence and detachment: a flow study with a series of hydroxyethyl methacrylate-ethyl methacrylate copolymers using video microscopy.

The adhesion and detachment of platelets were studied on glass coatings of a series of copolymers of hydroxyethyl methacrylate (HEMA) and ethyl methacrylate (EMA). Observations of the interactions of mepacrine labelled washed platelets with these surfaces from a flowing (500 s-1 wall shear rate) suspension in Tyrode's solution containing albumin and red cells were made with epifluorescent video microscopy (EVM). Total platelet adhesion, including platelets which adhere on first contact and platelets which attach temporarily before adhesion, and the number of detaching platelets were minimal for the 0 and 20% EMA copolymers, reached a maximum for the 50% EMA copolymer and showed reduced values for the 80% and 100% EMA copolymers. For the 50, 80, and 100% EMA copolymers, the adhesion values expressed, as a percentage of total contacting platelets, were not different. Albumin adsorption to these copolymers shows a continuous increase from the 0% to the 100% EMA copolymer. It is likely that the peak in platelet adhesion at the 50% EMA composition is related to: low protein adsorption on the 0 and 20% EMA copolymers, too little albumin adsorption to block adhesion on the 50% EMA copolymer, and full-scale blocking on the 80 and 100% EMA copolymers due to greater albumin adsorption.

Adult↗
PubMed1992

Platelet adherence and detachment with adsorbed fibrinogen: a flow study with a series of hydroxyethyl methacrylate-ethyl methacrylate copolymers using video microscopy.

The adhesion and detachment of platelets were studied on glass coatings of a series of copolymers of hydroxyethyl methacrylate (HEMA) and ethyl methacrylate (EMA) with preadsorbed fibrinogen. Observations of the interactions of acridine-orange-labeled washed platelets with these surfaces from a flowing (500 s-1 wall shear rate) suspension in Tyrode's solution containing albumin and red cells were made with epifluorescent video microscopy (EVM). In some cases preadsorbed materials were incubated for 24 h, during which little or no loss of protein occurred. Protein surface concentration, by itself, was a poor indicator of expected cell adhesion and morphology. Surface chemistry was a second important factor which must be considered. A third observation is that for the 100% EMA copolymer, 24 h of incubation led to a large reduction in platelet adhesion when compared to the 100% EMA material without incubation. For the 0% and 100% EMA polymers, the percentage of contacting platelets which adhere and detach is greater for the 24-h incubation cases than for those not incubated. These results led to the conclusion that our most hydrophilic surface favors adhesion with detachment, transient cell contact, over long-term adhesion, as does incubation of adsorbed protein. A brief discussion is presented of a possible connection between this behavior and platelet consumption in vivo for hydrogels.

Adsorption↗
PubMed1987

Microencapsulation of CHO cells in a hydroxyethyl methacrylate-methyl methacrylate copolymer.

Chinese hamster ovary fibroblasts, as model cells, have been microencapsulated in a hydroxyethyl methacrylate-methyl methacrylate copolymer (HEMA-MMA) by interfacial precipitation. The polymer containing approximately equal to 75 mol% HEMA, dissolved in polyethylene glycol 200 (PEG 200) was coextruded with the cell suspension (4-6 X 10(5) cells/ml in the alpha-MEM with 10% foetal calf serum +/- Ficoll 400/PBS) through a concentric needle assembly. Polymer solution droplets, containing cells, were blown off the end of the needle assembly by a coaxial filtered air stream into a nonsolvent bath containing phosphate buffered saline (PBS) with 5 ppm Pluronic L101, overlaid with hexadecane. The nascent capsules hang at the hexadecane/PBS interface while the solvent is extracted into the aqueous nonsolvent, to precipitate the polymer around the cells. The resultant capsules were 500 microns-1 mm in diam. with a microporous sponge-like interior, and also very tough and flexible. The cells survived encapsulation based on subculture ability, retention of some fluorescein diacetate (FDA) activity over 5 d and direct light microscopic evidence of cell growth over 10 d after histological sectioning and staining. However, cell growth was not uniformly observed (especially in the FDA assay) and this was attributed to space limitations for growth within the microporous interior. Continued development of this process and adaptation to cells such as pancreatic islets is expected to lead to hybrid artificial organs which are capable of ameliorating metabolic disorders such as diabetes.

Acrylates↗
PubMed1990

Surface properties of copolymers of alkyl methacrylates with methoxy (polyethylene oxide) methacrylates and their application as protein-resistant coatings.

New polymeric surfactants, copolymers of alkyl methacrylates with methoxy (polyethylene oxide) methacrylates, were synthesized and characterized by gel permeation chromatography. They were studied as possible means to produce polyethylene oxide-rich surfaces by a simple coating treatment on common hydrophobic medical materials. They were further studied as cleaners for the removal of proteins preadsorbed on hydrophobic surfaces. The surface properties of the copolymers such as the adsorption properties of the copolymer on a hydrophobic surface, low density polyethylene, the protein-resistant character of the prepared polyethylene oxide surfaces and the effectiveness of the copolymers for removal of proteins pre-adsorbed on the surface, were investigated by X-ray photoelectron spectroscopy and by using 125I-labelled copolymers and 125I-labelled proteins. The surface properties of the synthesized copolymers were compared with those of commercially available polyethylene oxide containing block copolymer surfactants.

Adsorption↗
PubMed1996

Water vapour sorption behaviour of copolymers of N, N-diethylaminoethyl methacrylate and methyl methacrylate.

Copolymers of N, N-diethylaminoethyl methacrylate (DEA) and methyl methacrylate (MMA) were synthesized in ethanolic solution and characterized in terms of reactivity ratios, densities and water vapour sorption. For the reaction conditions studied the copolymerization is essentially random. Polymer densities, determined by centrifugation in a density gradient, range from 1.10 for pDEA to 1.13 for p(DEA/MMA) 52/48 mol%. Flory-Huggins chi parameters were determined by isopiestic water vapour sorption, and were found to depend on both the comonomer ratio and the water content. An exceptionally strong dependence of chi on water content (or equivalently, polymer volume fraction) suggests that Flory-Huggins theory is not the proper theory to apply, especially for the polymers with the highest MMA content. Analysis of the data in terms of the Zimm-Lundberg cluster theory reveals that as the polymer becomes more hydrophobic and glassy with increased MMA, the sorption becomes more nonuniform in the polymer.

Adsorption↗
PubMed1996

Dopamine secretion by PC12 cells microencapsulated in a hydroxyethyl methacrylate--methyl methacrylate copolymer.

A rat pheochromocytoma cell line (PC12) was encapsulated in a water-insoluble hydroxyethyl methacrylate-methyl methacrylate copolymer by interfacial precipitation from a polyethylene glycol 200 solution into phosphate-buffered saline. The resulting capsules (660 +/- 44 microns in diameter; 84 +/- 27 microns wall thickness) contained viable PC12 cells in a spheroidal arrangement, much like tumour spheroids, the latter grown on surfaces unsuitable for cell attachment. In these spheroids, the viable cells formed a band approximately 100 microns thick, surrounding an inner core of necrotic cells. A similar arrangement was seen 14, 28 and 42 days after encapsulation, with capsules maintained in an in vitro tissue culture environment; the annular ring was roughly constant in size, although the packing density appeared to increase over the 6 week observation period. During the first 4 weeks, when measurements were made the encapsulated cells converted a tetrazolium dye (MTT) into an insoluble formazan product, in a time-after-encapsulation-dependent manner. This indicated that PC12 cells retained viability despite encapsulation and an ability to increase (at least in part) their metabolic capacity, presumably by a combination of proliferation and altered cellular activity. The encapsulated PC12 cells also secreted dopamine when incubated in a high potassium release medium but not in a low potassium, conventional tissue culture medium (RPMI 1640). Consistent with the MTT results, the amount of dopamine released was also dependent on the time after encapsulation, as well as the cell density at the time of encapsulation.

Animals↗
PubMed2004

Methyl methacrylate in poly(methyl methacrylate)--validation of direct injection gas chromatography.

Gas chromatography (GC) was investigated for the determination of residual methyl methacrylate (MMA) in heat-processed poly(methyl methacrylate) (PMMA) denture base material emphasizing recovery and validation. Standard solutions of MMA and emulsion-polymerized PMMA in dichloromethane were analysed, before and after distillation by a room-temperature air stream into a liquid nitrogen trap, and in the presence of PMMA by direct injection. Quantitative NMR analysis using dimethyl sulphoxide as internal calibration standard in deuterated chloroform solutions provided validation. Good concordance was observed between results under all conditions; no problems arose from direct injection of PMMA solution for GC. Good straight line responses in log-log plots were generally observed. For GC and MMA: log-log calibration curve (slope: 0.9552 +/- 0.0051, r2: 0.9992, n = 32) indicated some non-linearity (t = 8.875, p approximately 4 x 10(-10)). Distillation gave slope: 0.9751 +/- 0.0213 (NS versus unity; t = 1.172, p > 0.25). For PMMA solutions, distillation (r2: 0.9301) gave greater scatter than direct injection (r2: 0.9704). For NMR: log-log plot of calculated versus actual MMA (slope: 0.9363 +/- 0.0157, r2: 0.9969, n = 13) again indicated non-linearity (t = 4.0682, p = 0.0019). PMMA solutions gave slope: 0.9477 +/- 0.0328, r2 = 0.9858 (NS versus unity; t = 1.5941, p = 0.13). Determination of MMA in PMMA by GC is recommended.

Calibration↗
PubMed2000

Ion-exclusion controlled size-exclusion chromatography of methacrylic acid-methyl methacrylate copolymers.

Controlled ion-exclusion allows compensation of hydrophobic adsorption in size-exclusion chromatography of negatively charged methacrylic acid-methyl methacrylate (Eudragit) polymers using methanol as a mobile phase. Properly selected low-ionic-strength conditions below 5 mM LiCl provide correct separation in the size-exclusion mode. Possible disturbing effects, mainly related to light scattering, under low-salt conditions are discussed and shown to be negligible if on-line concentration-light scattering detection is used. The absence of these disturbances is checked by a comparison of experiments performed in methanol containing 1.25 mM and 2.5 mM LiCl. Molecular mass averages and distributions identical within the experimental error are obtained.

Chromatography, Gel↗
PubMed2001

In vitro evaluation of the bioadhesive properties of hydrophobic polybasic gels containing N,N-dimethylaminoethyl methacrylate-co-methyl methacrylate.

The bioadhesive properties of the hydrophobic, basic polyelectrolyte hydrogel disks containing crosslinked N,N-dimethylaminoethyl methacrylate-co-methyl methacrylate 30/70mol% were evaluated in vitro using gastric (pH 1.2), sublingual (pH 6.5), vaginal (pH 4.0) and intestinal (pH 7.5) pig's mucosas. Adhesive strength was measured using a modified Du Noüy tensiometer by measuring the force of detachment between a gel disk and the respective mucosa. The effect of crosslinker content in the gel was evaluated. It was found an increase in the adhesive strength with the increase of crosslinker content in the pH range of 4.0-7.5. For the evaluation at pH 1.2 (gastric mucosa) the opposite behavior was observed. The results indicate that initial bioadhesive contact may be the result of surface energy effects and/or electrostatic interactions of oppositely charged groups between mucin and the gel. In some cases, mucus dehydration may also be involved. When the gel is swollen, chain interpenetration also plays a roll in the bioadhesive interaction. The gels presented bioadhesive forces in gastric and vaginal mucosas (acidic medium), similar to the adhesive forces of well-known bioadhesives such as hydroxymethylcellulose and sodium alginate to the intestinal mucosa. The results indicate that hydrophobic polybasic gels present bioadhesive properties that make them suitable for site specific, pH controlled drug delivery.

Animals↗
PubMed2002

Manufacture of poly(2-hydroxyethyl methacrylate-co-methyl methacrylate) hydrogel tubes for use as nerve guidance channels.

Hydrogel tubes of poly(2-hydroxyethyl methacrylate-co-methyl methacrylate) (p(HEMA-co-MMA)) made by liquid-liquid centrifugal casting are being investigated as potential nerve guidance channels in the central nervous system. An important criterion for the nerve guidance channel is that its mechanical properties are similar to those of the spinal cord, where it will be implanted. The formulated p(HEMA-co-MMA) tubes are soft and flexible, consisting of a gel-like outer layer, and an interconnected macroporous, inner layer. The relative thickness of the gel phase to macroporous phase is controlled by the formulation chemistry, and specifically by the ratio of co-monomers, HEMA and MMA. By varying the surface chemistry of the mold within which the tubes are synthesized, tubes were prepared with either a "cracked" or a smooth outer morphology. Tubes with the cracked outer morphology had periodic channels that traversed the wall of the tube, which resulted in a lower modulus than smooth outer morphology tubes, yet likely greater diffusive permeability. For tubes (and not rods) to be formed, phase separation must precede gelation as is detailed in a formulation phase diagram for HEMA, MMA and water. The tensile elastic modulus of p(HEMA-co-MMA) tubes reflected the formulation chemistry, with greater moduli (up to 400 kPa) recorded for tubes having 10 wt% MMA. The p(HEMA-co-MMA) tubes therefore had similar mechanical properties to those of the spinal cord, which has a reported elastic modulus range between 200 and 600 kPa.

Biocompatible Materials↗