Chemoenzymatic synthesis of sugar-containing biocompatible hydrogels: crosslinked poly(beta-methylglucoside acrylate) and poly(beta-methylglucoside methacrylate).
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.
Park
Dae Won
DW
Department of Chemical Engineering, Yonsei University, 134 Sinchon-dong, Seodaemun-gu, Seoul 120-749, Korea.
Haam
Seungjoo
S
Lee
Tai Gyu
TG
Kim
Hae-Sung
HS
Kim
Woo-Sik
WS
D000179:Acrylates / Q000737:chemistry* / Q000494:pharmacology; D000215:Acylation; D000438:Alcohols / Q000737:chemistry; D000818:Animals; D001672:Biocompatible Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D002241:Carbohydrates / Q000032:analysis*; D002470:Cell Survival / Q000187:drug effects; D003432:Cross-Linking Reagents / Q000737:chemistry; D004058:Diffusion; D005960:Glucosides / Q000737:chemistry* / Q000494:pharmacology; D020100:Hydrogels / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism*; D006868:Hydrolysis; D007700:Kinetics; D008049:Lipase / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D008689:Methacrylates / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D008855:Microscopy, Electron, Scanning; D015394:Molecular Structure; D041681:NIH 3T3 Cells; D017550:Spectroscopy, Fourier Transform Infrared
D000179:Acrylates; D000438:Alcohols; D001672:Biocompatible Materials; D002241:Carbohydrates; D003432:Cross-Linking Reagents; D005960:Glucosides; D020100:Hydrogels; D008689:Methacrylates; C499769:poly(beta-methylglucoside acrylate); C499770:poly(beta-methylglucoside methacrylate); D008049:Lipase