Methyl Vinyl Ether-maleic Anhydride Research Articles

Fabrication and characterization of poly(methyl vinyl ether maleic anhydride) blended poly(lactic acid) ultrafiltration membrane with upgraded antifouling and separation performance

In this present study, a novel environment-friendly bio-polymeric hybrid ultrafiltration membrane was fabricated by incorporating poly(methyl vinyl ether maleic anhydride) (PMVEAMA) into the poly(lactic acid) (PLA) polymer matrix. The integration of PMVEAMA into PLA significantly altered the membrane's structural morphology, functional characteristics, and filtration performance. As a result, key functional parameters like membrane porosity and water content were increased, which exhibiting the improved hydrophilicity. Furthermore, the molecular weight cut-off of the PLA/PMVEAMA membrane reached up to a maximum of 66.5 KDa with an average pore size of 9.14 nm, subsequently improving the flux of the membrane up to 2.8 times than PLA membrane. The functional capacity of the synthesized membrane was further assessed by testing its ability to filter toxic chlorophenolic compounds. Rejection studies reveal that the PLA/PMVEAMA membrane achieved a rejection efficiency of 44.64 % pentachlorophenol (PCP) and 51.85 % 2,4-dichlorophenol (DCP). Moreover, fouling studies revealed enhanced PCP and DCP flux recovery ratios of 50.94 % and 51.40 %, respectively, with a significant reduction in the flux decline rate. Additionally, the synthesized PLA/PMVEAMA membranes improved stability and regenerative properties up to 12 filtration cycles and antifouling properties highlight its potential to filter chlorophenolic compounds from wastewater.

Designing a novel poly (methyl vinyl ether maleic anhydride) based polymeric membrane with enhanced antifouling performance for removal of pentachlorophenol from aqueous solution

In this current study, poly (methyl vinyl ether maleic anhydride) (PMVEAMA), a sustainable additive, was incorporated into poly (ether-ether sulfone) (PEES) polymer to design a novel polymeric hybrid membrane for the efficient filtration of toxic pentachlorophenol (PCP) from an aqueous medium. Hydrophilic additives significantly altered the membrane's morphology, structure, porosity, water content, and flux performance compared to the bare PEES membrane. The influence of PMVEAMA on the structural modification of the synthesized polymer membrane was confirmed by SEM, ATR-FTIR, XRD, AFM, zeta potential and contact angle. Findings revealed that the addition of PMVEAMA to the PEES polymer enhances the porosity (17.7%–28.9%), water content (29.8%–39.8%), and pure water flux (186 Lm−2h−1 to 349 Lm−2h−1). The effect of PMVEAMA concentration on the PEES membrane exhibited more finger like pores, better porosity and hydrophilicity, reduced surface roughness, fouling and increased permeability. The fouling studies exhibit an improved 57% PCP rejection and permeation flux of 22.3 Lm−2h−1 due to the addition of the hydrophilic additive. Surprisingly, the incorporation of PMVEAMA into the bare PEES membrane resulted in a high flux recovery ratio of 73.7%. The antifouling properties and enhanced permeability of the PEES/PMVEAMA membrane indicates its potential application in water purification sectors for the efficient separation of contaminants.

Influence of composition and powder/water ratio on adhesion strength and initial viscosity of powder-type denture adhesives based on CMC-Na and PVM-MA

We evaluated the influence of the composition and powder/water (P/W) ratio of powder-type denture adhesives (DA) based on sodium carboxymethyl cellulose (CMC-Na) and poly(methyl vinyl ether-maleic anhydride) (PVM-MA) on the strength of adhesion to acrylic resin and initial viscosity. Twenty types of DA were prepared by mixing CMC-Na and PVM-MA at various weight ratios with distilled water in P/W ratios ranging from 0.125 to 0.500. Adhesion strength and viscosity were measured using a universal testing machine and a controlled-stress rheometer, respectively. A higher percentage of CMC-Na and higher P/W ratios resulted in higher adhesion strength and viscosity. The effect of the CMC-Na/PVM-MA weight ratio on adhesion strength and viscosity was larger than that of the P/W ratio. DA with higher viscosity had higher adhesion strength. These results suggest that the adhesion strength and initial viscosity of powder-type DA can be controlled via the P/W ratio and the CMC-Na/PVM-MA weight ratio.

Recovery of intact human norovirus from cabbage Kimchi stored at 4 °C and 10 °C during fermentation

This study aimed to evaluate the recovery of structurally intact human norovirus (NoV) during Kimchi fermentation at varying temperatures. Lactic acid bacteria (LAB), pH, and acidity during storage and fermentation were also measured to assess the correlation between NoV reduction and microbial or physicochemical property alterations. LAB number, NoV G titer, pH, acidity, and the ability of NoV GII.4 to persist in Kimchi stored at 4 °C and 10 °C (survivability) as determined using nano magnetic beads conjugated with poly(methyl vinyl ether-maleic anhydride) combined with quantitative real-time reverse transcription-polymerase chain reaction amplification were investigated up to 28 days post-inoculation. NoV was detected in all test samples after 28 days although the NoV recovery quantity was reduced to 1.31 (4 °C) and 1.66 (10 °C) log10 genomic copies/reaction. The time required to reduce the amount of virus by 2.57 log10 (td) on survival plots of NoV determined using a modified Weibull model was 2445 days at 4 °C and 138 days at 10 °C. These results indicate that NoV from food preparation or processing is able to persistently survive in Kimchi. Therefore, preventing NoV transmission is important for protecting Kimchi against NoV contamination.

Scientific Opinion on the safety of “Methyl Vinyl Ether‐Maleic Anhydride Copolymer” (chewing gum base ingredient) as a Novel Food ingredient

Following a request from the European Commission, the EFSA Panel on Dietetic Products, Nutrition and Allergies (NDA) was asked to deliver a scientific opinion on the safety of “methyl vinyl ether-maleic anhydride copolymer (Gantrez SF)” as a novel food ingredient in the context of Regulation (EC) No 258/97. The novel food ingredient Gantrez SF is an anhydrous copolymer formed by the reaction of methyl vinyl ether (MVE) and maleic anhydride (MAN) under appropriate conditions. The Panel considers that the information provided on the specifications, stability and production process do not raise safety concerns. An estimated daily intake (EDI) for Gantrez SF associated with its use in chewing gum may be calculated based on the maximum concentration (2 %) of Gantrez SF in finished chewing gum, and on the level at which chewing gum is consumed. Based on data from the United Kingdom, a high intake estimate of 280 mg Gantrez SF per day was derived. The Panel notes that the NOAEL of 1.8 and 2.1 g/kg bw per day Gantrez SF for male and female rats, respectively, which was derived from a 90-day subchronic toxicity study, is about 500-fold above this conservative intake estimate. The Panel has no safety concerns regarding genotoxicity and the low molecular weight components. The Panel concludes that the novel food ingredient, methyl vinyl ether-maleic anhydride copolymer (Gantrez SF), is safe under the proposed uses and use levels.

Investigation of metal–polyelectrolyte complex toxicity

Water-soluble binary and ternary copper complexes of polyelectrolytes were synthesized, and the toxicity of these complexes was tested in mouse fibroblast cell line (L929) in vitro. Both the binary and ternary complexes were prepared at the ratio of 0.4 mole copper(II) ions per monomer of acrylic acid and 0.5 mole copper(II) ions per monomer of methyl vinyl ether maleic anhydride, furthermore at the ratio of 1 and 2 mole bovine serum albumin per mole of polyacrylic acid and poly(methyl vinyl ether-co-maleic anhydride), respectively. Compared to binary copper(II)-polyelectrolyte complexes, these ternary complexes have been determined to be of least toxicity.

Virus capture using anionic polymer-coated magnetic beads (Review)

The recent incidence of emerging and re-emerging viruses is a serious health concern worldwide. The development of transportation systems, such as air travel, has increased the risk of a global pandemic caused by emerging viruses. Agents causing novel infections are often zoonotic, crossing from the natural host into the human population. Hence, comprehensive surveillance of virus-infected animals as well as humans is required. However, the number of virus particles in clinical and environmental samples is usually very low. Thus, a method to concentrate the virus is sometimes required in order to enable detection. We recently reported that magnetic beads coated with an anionic polymer, poly(methyl vinyl ether-maleic anhydride) can be used to facilitate the rapid and sensitive detection of viruses. In this review, we describe recent developments for concentrating viruses using anionic magnetic beads.

Laser-Engineered Dissolving Microneedle Arrays for Transdermal Macromolecular Drug Delivery

To assess the feasibility of transdermal macromolecule delivery using novel laser-engineered dissolving microneedles (MNs) prepared from aqueous blends of 20% w/w poly(methylvinylether maleic anhydride) (PMVE/MA) in vitro and in vivo. Micromoulding was employed to prepare insulin-loaded MNs from aqueous blends of 20% w/w PMVE/MA using laser-engineered moulds. To investigate conformational changes in insulin loaded into MNs, circular dichroism spectra were obtained. In vitro drug release studies from MNs across neonatal porcine skin were performed using Franz diffusion cells. The in vivo effect of MNs was assessed by their percutaneous administration to diabetic rats and measurement of blood glucose levels. MNs loaded with insulin constituted exact counterparts of mould dimensions. Circular dichroism analysis showed that encapsulation of insulin within polymeric matrix did not lead to change in protein secondary structure. In vitro studies revealed significant enhancement in insulin transport across the neonatal porcine skin. Percutaneous administration of insulin-loaded MN arrays to rats resulted in a dose-dependent hypoglycaemic effect. We demonstrated the efficacy of MNs prepared from aqueous blends of PMVE/MA in transdermal delivery of insulin. We are currently investigating the fate of the delivered insulin in skin and MN-mediated delivery of other macromolecules.

Corrigendum to “Anionic polymer, poly(methyl vinyl ether–maleic anhydride)-coated beads-based capture of human influenza A and B virus” [Bioorg. Med. Chem. 17 (2009) 752–757

Corrigendum to “Anionic polymer, poly(methyl vinyl ether–maleic anhydride)-coated beads-based capture of human influenza A and B virus” [Bioorg. Med. Chem. 17 (2009) 752–757

Use of anionic polymer, poly(methyl vinyl ether-maleic anhydride)-coated beads for capture of respiratory syncytial virus

Respiratory syncytial virus (RSV) is the single most important cause of severe lower respiratory tract infections in infants and young children, and a major public health concern in pediatrics. However, current diagnostic methods for RSV are not sufficiently sensitive. In addition, there is no simple method for enhancing RSV detection. Here, a method for capturing RSV from nasal fluid has been developed using magnetic beads coated with an anionic polymer, poly(methyl vinyl ether-maleic anhydrate). The beads were incubated with RSV-infected nasal fluid, then separated from the supernatant by applying a magnet field and washed. The absorption of RSV by the beads was confirmed by immunochromatography, reverse transcription-polymerase chain reaction, Western blotting and an enzyme-linked immunosorbent assay, which indicated the presence of nucleocapsid protein, fusion protein, and the viral genome of RSV on the incubated beads. Therefore, this capture method will contribute to the improvement of RSV detection.

Anionic polymer, poly(methyl vinyl ether–maleic anhydride)-coated beads-based capture of human influenza A and B virus

An anionic magnetic beads-based method was developed for the capture of human influenza A and B viruses from nasal aspirates, allantoic fluid and culture medium. A polymer, poly(methyl vinyl ether–maleic anhydride) [poly(MVE-MA)], was used to endow magnetic beads with a negative charge and bioadhesive properties. After incubation with samples containing human influenza virus, the beads were separated from supernatants by applying a magnetic field. The absorption of the virus by the beads was confirmed by hemagglutinin assay, immunochromatography, Western blotting, egg infection, and cell infection. Successful capture was proved using 5 H1N1 influenza A viruses, 10 H3N2 influenza A viruses, and 6 influenza B viruses. Furthermore, the infectivity in chicken embryonated eggs and Madin–Darby canine kidney (MDCK) cells of the captured human influenza virus was similar to that of the total viral quantity of starting materials. Therefore, this method of capture using magnetic beads coated with poly(MVE-MA) can be broadly used for the recovery of infectious human influenza viruses.

Efficient capture of infectious H5 avian influenza virus utilizing magnetic beads coated with anionic polymer

The possible emergence of a pandemic influenza virus from the avian influenza virus (AIV) has become a serious threat. The isolation of viruses will be crucial for further virological analysis and the development of vaccines. However, currently, there is no simple method for facilitating the isolation of infectious AIV. Here, we have developed a simple method of capturing AIV using anionic magnetic beads. The method employed the capture of AIV (H5N1, H5N2, and H5N3) from liquid samples such as allantoic fluid (AF) and cell culture medium (CM) using magnetic beads coated with an anionic polymer, poly(methyl vinyl ether-maleic anhydride). After their incubation with AIV-containing samples, the magnetic beads were separated from the supernatant by applying a magnetic field. The absorption of AIV on the beads was confirmed by immunochromatography and an enzyme-linked immunosorbent assay, which indicated the presence of hemagglutinin, neuraminidase, and nucleoprotein of AIV. Furthermore, the infectivity in chicken eggs of AIV captured by magnetic beads was similar to that of the starting materials. The capture of AIV using magnetic beads coated with anionic polymers will contribute to the sufficient recovery of infectious AIV and approach for potential pandemic influenza viruses.

Stability of 5-aminolevulinic acid in novel non-aqueous gel and patch-type systems intended for topical application

Aminolevulinic acid (ALA) stability within topical formulations intended for photodynamic therapy (PDT) is poor due to dimerisation to pyrazine-2,5-dipropionic acid (PY). Most strategies to improve stability use low pH vehicles, which can cause cutaneous irritancy. To overcome this problem, a novel approach is investigated that uses a non-aqueous vehicle to retard proton-induced charge separation across the 4-carbonyl group on ALA and lessen nucleophilic attack that leads to condensation dimerisation. Bioadhesive anhydrous vehicles based on methylvinylether-maleic anhydride copolymer patches and poly(ethyleneglycol) or glycerol thickened poly(acrylic acid) gels were formulated. ALA stability fell below pharmaceutically acceptable levels after 6months, with bioadhesive patches stored at 5°C demonstrating the best stability by maintaining 86.2% of their original loading. Glycerol-based gels maintained 40.2% in similar conditions. However, ALA loss did not correspond to expected increases in PY, indicating the presence of another degradative process that prevented dimerisation. Nuclear magnetic resonance (NMR) analysis was inconclusive in respect of the mechanism observed in the patch system, but showed clearly that an esterification reaction involving ALA and both glycerol and poly(ethyleneglycol) was occurring. This was especially marked in the glycerol gels, where only 2.21% of the total expected PY was detected after 204days at 5°C. Non-specific esterase hydrolysis demonstrated that ALA was recoverable from the gel systems, further supporting esterified binding within the gel matrices. It is conceivable that skin esterases could duplicate this finding upon topical application of the gel and convert these derivatives back to ALA in situ, provided skin penetration is not affected adversely.

Comparison of Methods of Immobilization to Enzyme-Linked Immunosorbent Assay Plates for the Detection of Sugar Chains

The immobilization of carbohydrates for solid-phase assays, including enzyme-linked immunosorbent assay (ELISA), is difficult because they are hydrophilic. We developed four new methods for the immobilization of oligosaccharides. ELISA plates were first coated with methyl vinyl ether–maleic anhydride copolymer (MMAC) and an excess of active anhydride groups was introduced. They were subsequently reacted, in four different ways, to bind oligosaccharides. In method 1, the anhydride groups were reacted with hydrazide groups, in the presence of adipic acid dihydrazide, and then coupled to the reducing ends of sugar chains by reductive amination. In method 2, the anhydride groups were reacted with p-aminophenyl glycoside obtained by reduction with p-nitrophenyl glycoside. In method 3, the anhydride groups were reacted with 1,6-hexamethylenediamine. Aminooxy groups were coupled to the amino groups introduced and then aminooxyacetic acid with carbodiimide and ligated to oligosaccharides by oxime formation. In method 4, stereospecifically aminated oligosaccharides reacted with the anhydride groups. We compared, in solid-phase assays systems, the ability of lectins to detect oligosaccharides immobilized with either one of these four new methods or one of the two methods previously described. Detection of sugars with lectins is useful because, in most cases, they recognize sugars stereospecifically. The immobilization method should therefore be carefully selected to avoid changing the configuration and substitution in C-1.

Immobilization of Saccharides and Peptides on 96-Well Microtiter Plates Coated with Methyl Vinyl Ether–Maleic Anhydride Copolymer

We have previously reported a method to immobilize protein ligands on microtiter plates coated with methyl vinyl ether–maleic anhydride copolymer (MMAC) [Isosaki, K.,et al.(1992)J. Chromatogr.597, 123–128]. In this study, we improved the MMAC method to efficiently immobilize not only small ligands such as peptides and oligosaccharides, which could not be efficiently immobilized previously, but also heparin via its reducing end. Amino and hydrazino groups were introduced to MMAC-coated microtiter plate wells by coupling to acid anhydride groups of MMAC with 1,6-hexamethylenediamine and adipic acid dihydrazide, respectively. The amino groups introduced were allowed to react with peptides by use of divalent cross-linkers. Hydrazino groups were allowed to react with formyl groups of saccharides by reductive amination. Peptides and oligosaccharides were immobilized in a dose-dependent manner by these methods. In the case of the angiotensin peptide thus immobilized, the detection limit by monoclonal antibodies was as low as 0.1–1 fmol peptide per well. Application of 20–200 nmol oligosaccharides to the well was sufficient to immobilize and subsequently detect lectins. Furthermore, heparin immobilized on the hydrazino-coated wells was successfully used for the binding assay of annexin IV.

Identification of the major allergens in wheat flour responsible for baker's asthma.

Baker's asthma, a typical occupational allergic disease, is a serious problem in the food industries. In this study, purification and identification of major allergens recognized by IgEs in sera of allergic patients were performed. Major immunoreactive proteins were purified from the albumin fraction by gel filtration on a Toyopearl HW-50 column followed by reverse-phase HPLC. The N-terminal amino acid sequences and molecular masses measured by MS indicated that the major immunoreactive proteins are members of the alpha-amylase inhibitor family, 0.19 and 0.28. Significant leukotriene release by each purified protein was observed in cell-associated stimulation tests, suggesting in vivo activity of these antigens. Carbohydrate analyses of major allergens indicated that they are monoglycosylated but not N-glycosylated in spite of the presence of a potential N-glycosylation site. Recombinant 0.19 expressed in Escherichia coli showed the same reactivity with IgE as native wheat 0.19 in Western blotting and ELISA using methyl vinyl ether maleic anhydride co-polymer as an immobilizing reagent, suggesting that the allergenic epitopes are located in the peptide portions.

Effect of several hydrophilic polymers on the permeation of morphine and salicylic acid through excised hairless rat skin.

Several hydrophilic polymers changed the cumulative amount of morphine (MOR) permeated through excised hairless rat skin from 1% MOR hydrochloride solution containing ethanol and l-menthol at concentrations of 40% and 5%, respectively, as permeation enhancers. Anionic polymers (carboxyvinylpolymer and methylvinylether-maleic anhydride copolymer) in the test solutions decreased the skin permeation of MOR, whereas cationic polymers (polyethyleneimine and chitosan) increased it, compared with that without polymers. Little change, however, was observed by the addition of nonionic polymers (hydroxypropylcellulose and polyethyleneoxide). On the other hand, the cationic and anionic polymers in the test solutions decreased and increased, respectively, the skin permeation of salicylic acid (SA) from the same enhancing system containing sodium salicylate. These opposite results were probably caused by the change in escaping tendency of the drugs from the vehicles, which was due to the drug-polymer interaction. (The escaping tendency has a great effect on the drug partition from the polymer solution to the skin barrier). The effect of hydrophilic polymers on the partition was then evaluated by Donnan membrane theory. The partition of MOR was increased and decreased by the presence of polymers having identical and opposite charge to MOR. The low partition of the drugs to skin may also be caused by low diffusion of the drugs in the polymer solutions. The drug release from the hydrophilic polymer solutions was then measured, and the release rate was found to have decreased in the presence of polymers having opposite charge to MOR and SA. It is suggested that these drug-polymer interactions changed the drug partition to skin thus changing the skin permeation of the drug.

Moisture-activated, electrically conducting bioadhesive interfaces for biomedical sensor applications

An electrically conducting interface for biomedical sensors, formed by casting and drying a polymer blend containing poly(methyl vinyl ether–maleic anhydride), glycerin as plasticizer, polyvinylpyrrolidone as viscosity builder and sodium chloride as the conducting electrolyte, is described. The resulting flexible bioadhesive film can adhere to a biological substrate under adverse conditions such as high humidity or when the biological substrate is immersed in water or a physiological fluid. The technology allows the design, for example, of an electrode for the monitoring of foetal heart rate and other physiological and analytical sensors. The effect on interface bioadhesion of varying both the composition of the polymer blend and the ambient moisture conditions on storage were investigated in respect of bioadhesion to a model substrate (wet neonate porcine skin) and the mechanical behaviour of the the interface. Optimum bioadhesive performance was obtained from films formulated from blends (pH 5) containing copolymer–plasticizer (2 + 1) and 5% m/m polyvinylpyrrolidone. Moisture conditions on storage had a significant effect on both the subsequent bioadhesive performance and the mechanical properties of the stored films. Formulation and hydration interactions were identified using 2 × 2 factorial design experiments. Data analysis was by a two-way ANOVA with repeated measures.

Moisture‐activated, electrically conducting bioadhesive hydrogels as interfaces for bioelectrodes: Effect of film hydration on cutaneous adherence in wet environments

AbstractThe water contents of bioadhesive polymeric films of poly(methylvinyl ether–maleic anhydride) copolymer, stored at two humidities and at two temperatures, have been determined by continuous gravimetry. The water contents of the films increased under storage conditions of increasing humidity. The bioadhesion of these films was assessed using an in vitro bioadhesive tester previously validated in our laboratory. Water uptake during the bioadhesive test was taken into account and the final water content of films recorded as a “corrected equilibrium water content” (CEWC). A good quality second‐order polynomial relationship between bioadhesion and the CEWC of films stored at both 23 and 35°C was developed using standard curve fitting analyses. A 2 × 2 factorial design experiment revealed that there was a synergistic relationship between temperature and percentage relative humidity with regard to their effect on the bioadhesion of polymeric films, presumably due to their combined effect on film water content. These findings have implications for both the storage and packaging of hydrophilic polymeric films. © 1995 John Wiley & Sons, Inc.

Moisture‐activated, electrically conducting bioadhesive hydrogels as interfaces for bioelectrodes: Effect of formulation factors on cutaneous adherence in wet environments

AbstractThe effect of varying the composition of a polymer blend containing poly(methylvinyl ether‐maleic anhydride) copolymer on the Brookfield viscosity of the blend and on the in vitro bioadhesive forces of resultant cast films was assessed. An increase in copolymer concentration increased both blend viscosity and film bioadhesion. Increasing the plasticizer concentration did not significantly alter bioadhesion but did influence film flexibility. Blend pH affected both viscosity and bioadhesion. However, for films to be biocompatible, formulation within the skin pH range was desirable. Films exhibited the ability to ‘restick’ after initial adherence, allowing repositioning of the adhered film in vivo. Factorial design experiments (22) showed that an additive bioadhesive effect occurred when copolymer and PVP concentrations were increased in the polymer blend. However, no interaction between copolymer and plasticizer was observed. Addition of sodium chloride to the polymer blend, necessary to render films electrically conducting for use as bioelectrode interfaces, decreased blend viscosity but did not exert a significant effect on film bioadhesion. © 1995 John Wiley & Sons, Inc.