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Chemical Compound Review

AGN-PC-00GIL1     2-methylprop-2-enoic acid

Synonyms: NSC-7393, ACMC-1CUMF, CCRIS 5925, AG-C-95123, AG-H-18617, ...
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Disease relevance of METHACRYLIC ACID


Psychiatry related information on METHACRYLIC ACID

  • Both the amount of MAA utilized in the preparation and reaction time affect the selectivity of chromatographic separation in both the HPLC and the CEC mode and electroosmotic flow [5].
  • We used standard operant conditioning methods to train animals to discriminate low odor concentrations of D-carvone from clean air, to discriminate L-carvone from clean air; or to discriminate between clean air and the odors of D-carvone, L-carvone, ethyl acetate and methacrylic acid [6].

High impact information on METHACRYLIC ACID


Chemical compound and disease context of METHACRYLIC ACID


Biological context of METHACRYLIC ACID

  • Hydrogen-bonding-based complexation of B-Me with MAA generates the binding sites complementary to B-Me after extracting B-Me from the resulting copolymers [14].
  • Activation of prothrombin to alpha-thrombin generates not only the catalytic site and associated regions but also an independent site (an exosite) which binds anionic substances, such as Amberlite CG-50 resin [cross-linked poly(methylacrylic acid)] [15].
  • Methacrylic acid (MAA), formed by hydrolysis of dex-HEMA, did not influence the cell morphology [16].
  • Polymerization kinetics of binary formulations improved over pure PMMA (from 15 to 4 min) as a result of over a 60-fold increase in propagation-to-termination constants (Kp/Kt) of MAA/MMA [17].
  • Bacterial adhesion on to copolymers with MAA was less than on to the corresponding homopolymers [18].

Anatomical context of METHACRYLIC ACID

  • The membranes were prepared by radiation-grafting methacrylic acid and vinylpyridine to films of DuPont cellophane PD-215 to produce cation-exchange and anion-exchange membranes, respectively [19].
  • These microcapsules of the functioning hepatocytes have a 2- to 3-microm outer layer of synthetic polymer with 25% 2-hydroxyethyl methacrylate, 25% methacrylic acid, and 50% methyl methacrylate and an inner layer of positively charged modified collagen as a suitable substrate for the enhanced cellular functions [20].
  • There was no significant difference between cell nuclei density and coating for the four groups: uncoated, HF-coated, NN-coated, and MA-coated [21].
  • This study was performed to identify the possible dental material intermediate 2,3-epoxymethacrylic acid (2,3-EMA) from MA in human liver microsomes [22].
  • Novel methacrylic acid (MAA) copolymers were examined for their pH-sensitive properties and ability to destabilize cell membranes in a pH-dependent manner [23].

Associations of METHACRYLIC ACID with other chemical compounds


Gene context of METHACRYLIC ACID

  • Modification of Cys-418 of pyruvate formate-lyase by methacrylic acid, based on its radical mechanism [29].
  • For composite materials containing a lightly cross-linked 2-hydroxyethylmethacrylate (HEMA)-methacrylic acid (MAA) copolymer and polymethacrylic acid (PMAA) as the hydrogel phase, permeability to water-soluble organic compounds and drugs were measured [30].
  • In addition to the polymerized biomaterials, monomers containing methacrylic acid units were also hydrolyzed with esterase and analyzed by ion chromatography to establish the sensitivity of the enzyme simulator [31].
  • Surfaces of copolymers with MAA had more negative zeta potentials than those of the corresponding homopolymers [18].
  • The objective of the current study was to investigate the influence of TEGDMA derived degradation products MA and TEG on the growth of three strains of oral bacteria: S. mutans strains NG8 and JH1005, and S. salivarius AT2 [32].

Analytical, diagnostic and therapeutic context of METHACRYLIC ACID


  1. Developmental toxicities of methacrylic acid, ethyl methacrylate, n-butyl methacrylate, and allyl methacrylate in rats following inhalation exposure. Saillenfait, A.M., Bonnet, P., Gallissot, F., Peltier, A., Fabriès, J.F. Toxicol. Sci. (1999) [Pubmed]
  2. Lichen planus-like contact dermatitis due to methacrylic acid esters. Kawamura, T., Fukuda, S., Ohtake, N., Furue, M., Tamaki, K. Br. J. Dermatol. (1996) [Pubmed]
  3. Microcapsules through polymer complexation. Part 3: Encapsulation and culture of human Burkitt lymphoma cells in vitro. Wen, S., Alexander, H., Inchikel, A., Stevenson, W.T. Biomaterials (1995) [Pubmed]
  4. Development of hydrogel implants for urinary incontinence treatment. Sefc, L., Prádný, M., Vacík, J., Michálek, J., Povýsil, C., Vítková, I., Halaska, M., Simon, V. Biomaterials (2002) [Pubmed]
  5. Novel surface modification of polymer-based separation media controlling separation selectivity, retentivity and generation of electroosmotic flow. Hosoya, K., Kubo, T., Takahashi, K., Ikegami, T., Tanaka, N. Journal of chromatography. A. (2002) [Pubmed]
  6. Concanavalin A application to the olfactory epithelium reveals different sensory neuron populations for the odour pair D- and L-carvone. Kirner, A., Deutsch, S., Weiler, E., Polak, E.H., Apfelbach, R. Behav. Brain Res. (2003) [Pubmed]
  7. Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays. Benito-Peña, E., Moreno-Bondi, M.C., Aparicio, S., Orellana, G., Cederfur, J., Kempe, M. Anal. Chem. (2006) [Pubmed]
  8. Nanoparticle-based continuous full filling capillary electrochromatography/electrospray ionization-mass spectrometry for separation of neutral compounds. Nilsson, C., Viberg, P., Spégel, P., Jörntén-Karlsson, M., Petersson, P., Nilsson, S. Anal. Chem. (2006) [Pubmed]
  9. Interactions of bupivacaine with a molecularly imprinted polymer in a monolithic format studied by NMR. Courtois, J., Fischer, G., Schauff, S., Albert, K., Irgum, K. Anal. Chem. (2006) [Pubmed]
  10. Molecularly imprinted fluorescent-shift receptors prepared with 2-(trifluoromethyl)acrylic acid. Matsui, J., Kubo, H., Takeuchi, T. Anal. Chem. (2000) [Pubmed]
  11. Expression of integrin and organization of F-actin in epithelial cells depends on the underlying surface. Wu, X.Y., Cornell-Bell, A., Davies, T.A., Simons, E.R., Trinkaus-Randall, V. Invest. Ophthalmol. Vis. Sci. (1994) [Pubmed]
  12. Ethyl acrylate-induced gastric toxicity. II. Structure-toxicity relationships and mechanism. Ghanayem, B.I., Maronpot, R.R., Matthews, H.B. Toxicol. Appl. Pharmacol. (1985) [Pubmed]
  13. Pediatric poisonings from household products: hydrofluoric acid and methacrylic acid. Perry, H.E. Curr. Opin. Pediatr. (2001) [Pubmed]
  14. Molecular imprinting of biotin derivatives and its application to competitive binding assay using nonisotopic labeled ligands. Takeuchi, T., Dobashi, A., Kimura, K. Anal. Chem. (2000) [Pubmed]
  15. Anion-binding exosite of human alpha-thrombin and fibrin(ogen) recognition. Fenton, J.W., Olson, T.A., Zabinski, M.P., Wilner, G.D. Biochemistry (1988) [Pubmed]
  16. In vitro biocompatibility of biodegradable dextran-based hydrogels tested with human fibroblasts. De Groot, C.J., Van Luyn, M.J., Van Dijk-Wolthuis, W.N., Cadée, J.A., Plantinga, J.A., Den Otter, W., Hennink, W.E. Biomaterials (2001) [Pubmed]
  17. Effect of methacrylic acid:methyl methacrylate monomer ratios on polymerization rates and properties of polymethyl methacrylates. Chen, T., Kusy, R.P. J. Biomed. Mater. Res. (1997) [Pubmed]
  18. Adhesion of Escherichia coli on to a series of poly(methacrylates) differing in charge and hydrophobicity. Harkes, G., Feijen, J., Dankert, J. Biomaterials (1991) [Pubmed]
  19. Cellulosic ion-exchange membranes for hemodialysis. Mollison, A.N., Graydon, W.F. J. Biomed. Mater. Res. (1977) [Pubmed]
  20. Hepatocyte encapsulation for enhanced cellular functions. Chia, S.M., Leong, K.W., Li, J., Xu, X., Zeng, K., Er, P.N., Gao, S., Yu, H. Tissue engineering. (2000) [Pubmed]
  21. Fibro-porous meshes made from polyurethane micro-fibers: effects of surface charge on tissue response. Sanders, J.E., Lamont, S.E., Karchin, A., Golledge, S.L., Ratner, B.D. Biomaterials (2005) [Pubmed]
  22. Identification of 2,3-epoxymethacrylic acid as an intermediate in the metabolism of dental materials in human liver microsomes. Seiss, M., Nitz, S., Kleinsasser, N., Buters, J.T., Behrendt, H., Hickel, R., Reichl, F.X. Dental materials : official publication of the Academy of Dental Materials (2007) [Pubmed]
  23. On the role of methacrylic acid copolymers in the intracellular delivery of antisense oligonucleotides. Yessine, M.A., Meier, C., Petereit, H.U., Leroux, J.C. European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft für Pharmazeutische Verfahrenstechnik e.V. (2006) [Pubmed]
  24. Microenvironmental pH modulation based release enhancement of a weakly basic drug from hydrophilic matrices. Tatavarti, A.S., Hoag, S.W. Journal of pharmaceutical sciences. (2006) [Pubmed]
  25. Controlled release of biomolecules from pH-sensitive network polymers prepared by radiation polymerization. Mahkam, M., Allahverdipoor, M. Journal of drug targeting. (2004) [Pubmed]
  26. Theoretical study of the oxidation reactions of methylacrylic Acid and methyl methacrylate by triplet o(2). Wang, G., Zhang, D., Xu, X., Zhou, J. The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment & general theory (2007) [Pubmed]
  27. Composite membrane of bacterially-derived cellulose and molecularly imprinted polymer for use as a transdermal enantioselective controlled-release system of racemic propranolol. Bodhibukkana, C., Srichana, T., Kaewnopparat, S., Tangthong, N., Bouking, P., Martin, G.P., Suedee, R. Journal of controlled release : official journal of the Controlled Release Society. (2006) [Pubmed]
  28. Use of an on-line imprinted polymer pre-column, for the liquid chromatographic-UV absorbance determination of carbaryl and its metabolite in complex matrices. Hantash, J., Bartlett, A., Oldfield, P., Dénès, G., O'Rielly, R., Roudiere, D., Menduni, S. Journal of chromatography. A. (2006) [Pubmed]
  29. Modification of Cys-418 of pyruvate formate-lyase by methacrylic acid, based on its radical mechanism. Plaga, W., Vielhaber, G., Wallach, J., Knappe, J. FEBS Lett. (2000) [Pubmed]
  30. Silicone rubber-hydrogel composites as polymeric biomaterials. II. Hydrophilicity and permeability to water-soluble low-molecular-weight compounds. Lopour, P., Vondrácek, P., Janatová, V., Sulc, J., Vacík, J. Biomaterials (1990) [Pubmed]
  31. Effect of esterase on methacrylates and methacrylate polymers in an enzyme simulator for biodurability and biocompatibility testing. Bean, T.A., Zhuang, W.C., Tong, P.Y., Eick, J.D., Yourtee, D.M. J. Biomed. Mater. Res. (1994) [Pubmed]
  32. Effect of composite resin biodegradation products on oral streptococcal growth. Khalichi, P., Cvitkovitch, D.G., Santerre, J.P. Biomaterials (2004) [Pubmed]
  33. Tantalum-loaded polyurethane microspheres for particulate embolization: preparation and properties. Thanoo, B.C., Sunny, M.C., Jayakrishnan, A. Biomaterials (1991) [Pubmed]
  34. The phase behaviour of poly(styrene-co-methacrylic acid)/poly(2,6-dimethyl-1,4-phenylene oxide) by inverse gas chromatography. Benabdelghani, Z., Etxeberria, A., Djadoun, S., Iruin, J.J., Uriarte, C. Journal of chromatography. A. (2006) [Pubmed]
  35. Pharmacokinetics of a novel HIV-1 protease inhibitor incorporated into biodegradable or enteric nanoparticles following intravenous and oral administration to mice. Leroux, J.C., Cozens, R., Roesel, J.L., Galli, B., Kubel, F., Doelker, E., Gurny, R. Journal of pharmaceutical sciences. (1995) [Pubmed]
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