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Chemical Compound Review

PHEMA     2-hydroxyethyl 2-methylprop-2-enoate

Synonyms: Mhoromer, HEMA, Poly-hema, PEG-MA, Blemmer E, ...
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Disease relevance of Glycol methacrylate gel


High impact information on Glycol methacrylate gel

  • In ultrathin sections of GMA- or Araldite-embedded medullae incubated with colloidal iron according to various techniques, the cell coat and lysosomes of both cell types were stained, unlike all the other cytoplasmic organelles [6].
  • Localization of TGF/beta 1 protein to intact alpha-granules of megakaryocytes, its putative storage site, was accomplished in glycol-methacrylate embedded porcine BM with an immunoperoxidase technique and light microscopy [7].
  • In an initial report (Carbonetto, S. T., M. M. Gruver, and D. C. Turner (1982) Science 216: 897-899) we described the use of 2-hydroxyethylmethacrylate (HEMA) in preparing defined culture substrates for studying nerve fiber growth [8].
  • Digestion of ultra-thin sections of erythrocytes embedded in the hydrophilic resin glycol methacrylate (GMA) has shown that the major component of the amorphous region is a rather acidic protein that is not haemoglobin, the most abundant protein in the erythrocyte [9].
  • A morphometric analysis of motor neurons in the spinal cord was performed on 2-hydroxyethyl methacrylate-embedded tissue from ten wst/wst mice, ten littermates (wst/+, +/+) without clinical deficits, and ten parental (+/+) control mice [10].

Chemical compound and disease context of Glycol methacrylate gel


Biological context of Glycol methacrylate gel

  • The GSTM1 genotype was clearly the most significant parameter explaining the variance in urinary PHEMA excretion (6-fold lower in GSTM1 null subjects; P < 0.0001) so that systematic GSTM1 genotyping should be recommended routinely for a correct interpretation of PHEMA urinary levels [15].
  • Differential adhesive conditions were established by precoating the plastic plates with poly (2-hydroxyethylmethacrylate) that allowed an accurate and reproducible control of cell shape, from flat to spherical [16].
  • Resin monomer 2-hydroxyethyl methacrylate (HEMA) is a potent inducer of apoptotic cell death in human and mouse cells [17].
  • It has been shown that NF-kappaB is activated probably to counteract HEMA-induced apoptosis [18].
  • A method employing fluorescent 2-hydroxyethyl methacrylate copolymer particles with dinitrophenyl haptenic group and anti-haptenic murine monoclonal antibodies of different isotypes is described for tracing Fc-receptors and for studies of phagocytosis via these cell surface structures [19].

Anatomical context of Glycol methacrylate gel


Associations of Glycol methacrylate gel with other chemical compounds

  • In vitro microdialysis glucose sampling was used to test the transient and steady-state suitability of antifouling hydrogel coatings, composed of 2-hydroxyethyl methacrylate, vinylpyrrolidinone, and poly(ethylene glycol) [24].
  • Porous monolithic polymers have been prepared by photoinitiated polymerization of mixtures consisting of 2-hydroxyethyl methacrylate, ethylene dimethacrylate, UV-sensitive free radical initiator and porogenic solvent within channels of specifically designed microfluidic chips and used as micromixers [25].
  • In the case of resin composite restorations, HEMA and TEGDMA are available in microgram quantities via the salivary surface in the minutes and hours after clinical placement and via dentin and pulp in the hours and days after placement [26].
  • Bonding procedures were carried out by means of an aqueous solution of 20% 2-methacryloyloxyethyl phenyl phosphoric acid (phenyl-P) and 30% 2-hydroxyethyl methacrylate, referred to as 2OP-30H, a "self-etching primer". The 20P-30H solution was applied to "intact" dentin (i.e., non-demineralized) for either 30 or 60 s [27].
  • Our findings provide evidence for the induction of micronuclei by TEGDMA, HEMA, and GMA under physiological conditions, indicating clastogenic activity of these chemicals in vitro [28].

Gene context of Glycol methacrylate gel

  • The excretion of specific mercapturic acids (PHEMA) in workers exposed to styrene has clearly been shown to depend on GSTM1 genotype, and GSTT1 genotype seems to modulate the excretion of one PHEMA diastereoisomer [29].
  • RESULTS: At 1 week, significantly more fibronectin was bound to the hydrophobic acrylate IOLs than to the 2-hydroxyethyl methacrylate (HEMA) containing hydrophilic acrylate IOLs (P <.05 to.0001) [30].
  • DC were hapten-derivatized with nickel sulphate (Ni) or 2-hydroxyethyl-methacrylate (HEMA), followed by tumour necrosis factor-alpha (TNF-alpha)-induced maturation, before autologous T cells and a cytokine cocktail of IL-1beta, IL-2 and IL-7 were added [31].
  • In decalcified (5% nitric acid) and undecalcified (glycol-methacrylate or resin embedded) routinely processed bone specimens osteoclasts against resorbing surfaces were identified with monoclonal antibodies directed against leucocyte common antigen (LCA) (PD7/26, 2B11), CD68 (KP1), and gpIIIa (Y2/51) but not against HLA-DR (CR3/43 and Ta11B5) [32].
  • In order to minimize these unfavorable contributions, less lipophilic monoliths were developed by copolymerization of different amounts of the hydrophilic monomer 2-hydroxyethyl methacrylate (HEMA) with GMA and EDMA, leading to GMA-co-HEMA-co-EDMA-terpolymeric monoliths [33].

Analytical, diagnostic and therapeutic context of Glycol methacrylate gel


  1. Endovascular treatment of intracranial aneurysms with a new silicone microballoon device: technical considerations and indications for therapy. Higashida, R.T., Halback, V.V., Dormandy, B., Bell, J.D., Hieshima, G.B. Radiology. (1990) [Pubmed]
  2. The etiology of transient endothelial changes in the human cornea. Holden, B.A., Williams, L., Zantos, S.G. Invest. Ophthalmol. Vis. Sci. (1985) [Pubmed]
  3. Low HEMA conjugation induces high autoantibody titer in mice. Sandberg, E., Bergenholtz, G., Kahu, H., Dahlgren, U.I. J. Dent. Res. (2005) [Pubmed]
  4. Cytotoxic effects of residual chemicals from polymeric biomaterials for artificial soft intraocular lenses. Chirila, T.V., Walker, L.N., Constable, I.J., Thompson, D.E., Barrett, G.D. Journal of cataract and refractive surgery. (1991) [Pubmed]
  5. Ia antigens in plastic-embedded tissues: a post-embedding immunohistochemical study. Hermanns, W., Colbatzky, F., Günther, A., Steiniger, B. J. Histochem. Cytochem. (1986) [Pubmed]
  6. Localization and characterization of carbohydrates in adrenal medullary cells. Cantin, M., Benchimol, S. J. Cell Biol. (1975) [Pubmed]
  7. Synthesis of transforming growth factor-beta 1 by megakaryocytes and its localization to megakaryocyte and platelet alpha-granules. Fava, R.A., Casey, T.T., Wilcox, J., Pelton, R.W., Moses, H.L., Nanney, L.B. Blood (1990) [Pubmed]
  8. Nerve fiber growth in culture on fibronectin, collagen, and glycosaminoglycan substrates. Carbonetto, S., Gruver, M.M., Turner, D.C. J. Neurosci. (1983) [Pubmed]
  9. Electron microscopic observations on the development and cytochemistry of the large granule complexes in chicken erythrocyte nuclei. Pearson, E.C., Davies, H.G. J. Cell. Sci. (1982) [Pubmed]
  10. Ultrastructural, morphometric, and immunocytochemical study of anterior horn cells in mice with "wasted" mutation. Lutsep, H.L., Rodriguez, M. J. Neuropathol. Exp. Neurol. (1989) [Pubmed]
  11. Occupational allergic contact dermatitis caused by exposure to acrylates during work with dental prostheses. Kanerva, L., Estlander, T., Jolanki, R., Tarvainen, K. Contact Derm. (1993) [Pubmed]
  12. Concomitant sensitization to triglycidyl isocyanurate, diaminodiphenylmethane and 2-hydroxyethyl methacrylate from silk-screen printing coatings in the manufacture of circuit boards. Jolanki, R., Kanerva, L., Estlander, T., Tarvainen, K. Contact Derm. (1994) [Pubmed]
  13. Localization of periodate-Schiff reactive glycosaminoglycans in semi-thin sections embedded in GMA-Quetol 523-MMA--application of a method for correlative light and electron microscopy of identical sites. Nagato, Y., Mitsui, T., Kushida, T., Kushida, H. Tokai J. Exp. Clin. Med. (1985) [Pubmed]
  14. Effect of methotrexate sorbed on modified 2-hydroxyethylmethacrylate carriers in mice of C3H strain with a solid Gardner lymphosarcoma. Motycka, K., Slavík, n.u.l.l., kocovská, A., Cihar, R., Spacek, P., Kubín, M. Neoplasma (1977) [Pubmed]
  15. Interest of genotyping and phenotyping of drug-metabolizing enzymes for the interpretation of biological monitoring of exposure to styrene. Haufroid, V., Jakubowski, M., Janasik, B., Ligocka, D., Buchet, J.P., Bergamaschi, E., Manini, P., Mutti, A., Ghittori, S., Arand, M., Hangen, N., Oesch, F., Hirvonen, A., Lison, D. Pharmacogenetics (2002) [Pubmed]
  16. Growth control and cell spreading: differential response in preneoplastic and in metastatic cell variants. Raz, A., Ben-Ze'ev, A. Int. J. Cancer (1982) [Pubmed]
  17. Resin monomer 2-hydroxyethyl methacrylate (HEMA) is a potent inducer of apoptotic cell death in human and mouse cells. Paranjpe, A., Bordador, L.C., Wang, M.Y., Hume, W.R., Jewett, A. J. Dent. Res. (2005) [Pubmed]
  18. Genetic and cellular toxicology of dental resin monomers. Schweikl, H., Spagnuolo, G., Schmalz, G. J. Dent. Res. (2006) [Pubmed]
  19. An advantageous method for detection of Fc-receptors and for studying Fc-receptor-mediated phagocytosis. Fornůsek, L., Kopecek, J., Vĕtvicka, V. Immunol. Lett. (1983) [Pubmed]
  20. Modification of capillary electrophoresis capillaries by poly(hydroxyethyl methacrylate), poly(diethylene glycol monomethacrylate) and poly(triethylene glycol monomethacrylate). Strelec, I., Pacáková, V., Bosáková, Z., Coufal, P., Guryca, V., Stulík, K. Electrophoresis (2002) [Pubmed]
  21. An FT-Raman spectroscopic investigation of dentin and collagen surfaces modified by 2-hydroxyethylmethacrylate. Xu, J., Stangel, I., Butler, I.S., Gilson, D.F. J. Dent. Res. (1997) [Pubmed]
  22. Histochemistry on glycol-methacrylate embedded human bone marrow biopsies. A new method and first evaluations. Burgio, V.L., Morra, E., Ascari, E. Haematologica (1982) [Pubmed]
  23. Intradermal challenge with interleukin-8 causes tissue oedema and neutrophil accumulation in atopic and non-atopic human subjects. Douglass, J., Dhami, D., Bulpitt, M., Lindley, I.J., Shute, J., Church, M.K., Holgate, S.T. Clin. Exp. Allergy (1996) [Pubmed]
  24. Glucose recovery with bare and hydrogel-coated microdialysis probes: experiment and simulation of temporal effects. Norton, L.W., Yuan, F., Reichert, W.M. Anal. Chem. (2007) [Pubmed]
  25. Porous polymer monoliths: simple and efficient mixers prepared by direct polymerization in the channels of microfluidic chips. Rohr, T., Yu, C., Davey, M.H., Svec, F., Fréchet, J.M. Electrophoresis (2001) [Pubmed]
  26. Bioavailability of components of resin-based materials which are applied to teeth. Hume, W.R., Gerzia, T.M. Crit. Rev. Oral Biol. Med. (1996) [Pubmed]
  27. Bonding to intact dentin. Nakabayashi, N., Saimi, Y. J. Dent. Res. (1996) [Pubmed]
  28. The induction of micronuclei in vitro by unpolymerized resin monomers. Schweikl, H., Schmalz, G., Spruss, T. J. Dent. Res. (2001) [Pubmed]
  29. Genetic susceptibility, biomarker respones, and cancer. Norppa, H. Mutat. Res. (2003) [Pubmed]
  30. Adhesion of soluble fibronectin, vitronectin, and collagen type IV to intraocular lens materials. Linnola, R.J., Sund, M., Ylönen, R., Pihlajaniemi, T. Journal of cataract and refractive surgery. (2003) [Pubmed]
  31. Human T lymphocyte priming in vitro by haptenated autologous dendritic cells. Rustemeyer, T., De Ligter, S., Von Blomberg, B.M., Frosch, P.J., Scheper, R.J. Clin. Exp. Immunol. (1999) [Pubmed]
  32. Use of monoclonal antibodies to recognise osteoclasts in routinely processed bone biopsy specimens. Athanasou, N.A., Puddle, B., Quinn, J., Woods, C.G. J. Clin. Pathol. (1991) [Pubmed]
  33. Polymethacrylate-type monoliths functionalized with chiral amino phosphonic acid-derived strong cation exchange moieties for enantioselective nonaqueous capillary electrochromatography and investigation of the chemical composition of the monolithic polymer. Preinerstorfer, B., Lindner, W., Lämmerhofer, M. Electrophoresis (2005) [Pubmed]
  34. A simplified plastic embedding and immunohistologic technique for immunophenotypic analysis of human hematopoietic and lymphoid tissues. Casey, T.T., Cousar, J.B., Collins, R.D. Am. J. Pathol. (1988) [Pubmed]
  35. Effect of thrombin on maturing human megakaryocytes. Cramer, E.M., Massé, J.M., Caen, J.P., Garcia, I., Breton-Gorius, J., Debili, N., Vainchenker, W. Am. J. Pathol. (1993) [Pubmed]
  36. Transdifferentiation of cardiac fibroblasts, a fetal factor in anti-SSA/Ro-SSB/La antibody-mediated congenital heart block. Clancy, R.M., Askanase, A.D., Kapur, R.P., Chiopelas, E., Azar, N., Miranda-Carus, M.E., Buyon, J.P. J. Immunol. (2002) [Pubmed]
  37. Functional polymeric microspheres based on 2-hydroxyethyl methacrylate for immunochemical studies. Rembaum, A., Yen, S.P., Cheong, E., Wallace, S., Molday, R.S., Gordon, I.L., Dreyer, W.J. Macromolecules (1976) [Pubmed]
  38. Polymorphism of xenobiotic-metabolizing enzymes and excretion of styrene-specific mercapturic acids. De Palma, G., Manini, P., Mozzoni, P., Andreoli, R., Bergamaschi, E., Cavazzini, S., Franchini, I., Mutti, A. Chem. Res. Toxicol. (2001) [Pubmed]
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