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Chemoenzymatic synthesis of sugar-containing biocompatible hydrogels: crosslinked poly(beta-methylglucoside acrylate) and poly(beta-methylglucoside methacrylate).

Abstract

Sugar-containing biocompatible hydrogels were synthesized chemoenzymatically by the following two steps: 1. lipase-catalyzed esterification of beta-methylglucoside with acrylic acid/methacrylic acid/vinyl acrylate/vinyl methacrylate in solvent as well as solvent-free process for the formation of sugar-containing monomers; and 2. polymerization process by free-radical polymerization with and without a crosslinker, ethylene glycol dimethacrylate (EGDMA). The solvent-free process resulted in an initial reaction rate approximately 1.5-2 times faster than that of the solvent process along with a complete consumption of beta-methylglucoside during the alcoholysis. The presence of pendant vinyl groups in beta-methylglucoside acrylate (MGAA) and beta-methylglucoside methacrylate (MGMAA) was confirmed by (1)H/(13)C NMR analysis, whereas the successful polymerization with the consumption of the vinyl groups was confirmed by Fourier transform infrared spectroscopy and (13)C NMR spectra. The surfaces of both poly(MGAA) and poly(MGMAA) were analyzed using scanning electron microscopy. The increased contents of EGDMA resulted in a higher tensile strength as well as a reduced swelling ratio of poly(MGAA) and poly(MGMAA). The swelling exponents were within the range of 0.53 and 0.98. In vitro cytotoxicity tests by MTT assay exhibited >90% cell viability in the poly(MGAA) and poly(MGMAA) without EGDMA, whereas a significantly decreased cell viability was observed for those with EGDMA.

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  • Authors+Show Affiliations

    ,

    Department of Chemical Engineering, Yonsei University, 134 Sinchon-dong, Seodaemun-gu, Seoul 120-749, Korea.

    , , ,

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    MeSH

    Acrylates
    Acylation
    Alcohols
    Animals
    Biocompatible Materials
    Carbohydrates
    Cell Survival
    Cross-Linking Reagents
    Diffusion
    Glucosides
    Hydrogels
    Hydrolysis
    Kinetics
    Lipase
    Magnetic Resonance Spectroscopy
    Methacrylates
    Mice
    Microscopy, Electron, Scanning
    Molecular Structure
    NIH 3T3 Cells
    Spectroscopy, Fourier Transform Infrared

    Pub Type(s)

    Journal Article
    Research Support, Non-U.S. Gov't

    Language

    eng

    PubMed ID

    15386484

    Citation

    TY - JOUR T1 - Chemoenzymatic synthesis of sugar-containing biocompatible hydrogels: crosslinked poly(beta-methylglucoside acrylate) and poly(beta-methylglucoside methacrylate). AU - Park,Dae Won, AU - Haam,Seungjoo, AU - Lee,Tai Gyu, AU - Kim,Hae-Sung, AU - Kim,Woo-Sik, PY - 2004/9/24/pubmed PY - 2005/4/22/medline PY - 2004/9/24/entrez SP - 497 EP - 507 JF - Journal of biomedical materials research. Part A JO - J Biomed Mater Res A VL - 71 IS - 3 N2 - Sugar-containing biocompatible hydrogels were synthesized chemoenzymatically by the following two steps: 1. lipase-catalyzed esterification of beta-methylglucoside with acrylic acid/methacrylic acid/vinyl acrylate/vinyl methacrylate in solvent as well as solvent-free process for the formation of sugar-containing monomers; and 2. polymerization process by free-radical polymerization with and without a crosslinker, ethylene glycol dimethacrylate (EGDMA). The solvent-free process resulted in an initial reaction rate approximately 1.5-2 times faster than that of the solvent process along with a complete consumption of beta-methylglucoside during the alcoholysis. The presence of pendant vinyl groups in beta-methylglucoside acrylate (MGAA) and beta-methylglucoside methacrylate (MGMAA) was confirmed by (1)H/(13)C NMR analysis, whereas the successful polymerization with the consumption of the vinyl groups was confirmed by Fourier transform infrared spectroscopy and (13)C NMR spectra. The surfaces of both poly(MGAA) and poly(MGMAA) were analyzed using scanning electron microscopy. The increased contents of EGDMA resulted in a higher tensile strength as well as a reduced swelling ratio of poly(MGAA) and poly(MGMAA). The swelling exponents were within the range of 0.53 and 0.98. In vitro cytotoxicity tests by MTT assay exhibited >90% cell viability in the poly(MGAA) and poly(MGMAA) without EGDMA, whereas a significantly decreased cell viability was observed for those with EGDMA. SN - 1549-3296 UR - https://www.unboundmedicine.com/medline/citation/15386484/Chemoenzymatic_synthesis_of_sugar_containing_biocompatible_hydrogels:_crosslinked_poly_beta_methylglucoside_acrylate__and_poly_beta_methylglucoside_methacrylate__ L2 - http://dx.doi.org/10.1002/jbm.a.30178 ER -