Changes in 1H-NMR chemical shifts of Bis-GMA and its related methacrylates induced by their interaction with phosphatidylcholine/cholesterol liposomes.
To clarify the hemolytic mechanism of Bis-GMA and its related methacrylates, the interaction of five methacrylates (Bis-GMA, MMA, NPGDMA, TEGDMA, and UDMA) with DPPC/Cholesterol (CS) liposomes, as a model for erythrocyte membranes, was studied by 1H-NMR spectroscopy. Exogenous Bis-GMA partitioning into the DPPC/CS liposomes caused disappearances of its proton signals. With NPGDMA, its signals broadened markedly in DPPC/CS liposomes. UDMA partitioning caused changes in chemical shifts to a higher field, whereas MMA and TEGDMA partitioning did not cause any changes in chemical shifts. It was concluded from these observations that Bis-GMA has a stronger interaction with the DPPC/CS liposomes than the other methacrylates used. The high hemolytic activity of Bis-GMA reported previously seemed to be due to its migration into the lipid bilayer of phospholipids containing CS in erythrocyte membranes.
Fujisawa
S
S
Tokyo Medical and Dental University.
Kadoma
Y
Y
Komoda
Y
Y
D015060:1,2-Dipalmitoylphosphatidylcholine / Q000378:metabolism; D017438:Bisphenol A-Glycidyl Methacrylate; D002784:Cholesterol / Q000378:metabolism; D004910:Erythrocyte Membrane / Q000187:drug effects / Q000378:metabolism*; D006461:Hemolysis; D008051:Lipid Bilayers / Q000378:metabolism; D008081:Liposomes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008689:Methacrylates / Q000378:metabolism* / Q000494:pharmacology; D015394:Molecular Structure; D010743:Phospholipids / Q000378:metabolism*
D008051:Lipid Bilayers; D008081:Liposomes; D008689:Methacrylates; D010743:Phospholipids; D015060:1,2-Dipalmitoylphosphatidylcholine; D017438:Bisphenol A-Glycidyl Methacrylate; D002784:Cholesterol