Chemoenzymatic synthesis of sugar-containing biocompatible hydrogels: Crosslinked poly(β-methylglucoside acrylate) and poly(β- methylglucoside methacrylate)

Dae Won Park, Seungjoo Haam, Tai Gyu Lee, Hae Sung Kim, Woo Sik Kim

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Abstract

Sugar-containing biocompatible hydrogels were synthesized chemoenzymatically by the following two steps: 1. lipase-catalyzed esterification of β-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 β-methylglucoside during the alcoholysis. The presence of pendant vinyl groups in β-methylglucoside acrylate (MGAA) and β-methylglucoside methacrylate (MGMAA) was confirmed by 1H/13C NMR analysis, whereas the successful polymerization with the consumption of the vinyl groups was confirmed by Fourier transform infrared spectroscopy and 13C 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.

Original languageEnglish
Pages (from-to)497-507
Number of pages11
JournalJournal of Biomedical Materials Research - Part A
Volume71
Issue number3
DOIs
Publication statusPublished - 2004 Dec 1

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Hydrogels
Methacrylates
Ethylene glycol
Sugars
Swelling
Polymerization
Cells
Nuclear magnetic resonance
Acids
Lipases
Esterification
Cytotoxicity
Free radical polymerization
Acrylics
Reaction rates
Fourier transform infrared spectroscopy
Assays
Tensile strength
Monomers
Scanning electron microscopy

All Science Journal Classification (ASJC) codes

  • Ceramics and Composites
  • Biomaterials
  • Biomedical Engineering
  • Metals and Alloys

Cite this

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abstract = "Sugar-containing biocompatible hydrogels were synthesized chemoenzymatically by the following two steps: 1. lipase-catalyzed esterification of β-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 β-methylglucoside during the alcoholysis. The presence of pendant vinyl groups in β-methylglucoside acrylate (MGAA) and β-methylglucoside methacrylate (MGMAA) was confirmed by 1H/13C NMR analysis, whereas the successful polymerization with the consumption of the vinyl groups was confirmed by Fourier transform infrared spectroscopy and 13C 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.",
author = "Park, {Dae Won} and Seungjoo Haam and Lee, {Tai Gyu} and Kim, {Hae Sung} and Kim, {Woo Sik}",
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AU - Haam, Seungjoo

AU - Lee, Tai Gyu

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AU - Kim, Woo Sik

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