Changes in 1H-NMR Chemical Shifts of Bis-GMA and Its Related Methacrylates Induced by Their Interaction with Phosphatidylcholine/Cholesterol Liposomes

• Published in: Dental Materials Journal Vol. 10; no. 2; pp. 121 - 127,231
• Main Authors: FUJISAWA, Seiichiro, KADOMA, Yoshinori, KOMODA, Yasuo
• Format: Journal Article
• Language: English
• Published: Japan The Japanese Society for Dental Materials and Devices 01.12.1991
• Subjects: 1,2-Dipalmitoylphosphatidylcholine - metabolism; Bis-GMA; Bisphenol A-Glycidyl Methacrylate; Cholesterol - metabolism; Dentistry; Erythrocyte Membrane - drug effects; Erythrocyte Membrane - metabolism; Hemolysis; Lipid Bilayers - metabolism; Liposomes - chemistry; Magnetic Resonance Spectroscopy; Methacrylates - metabolism; Methacrylates - pharmacology; Molecular Structure; NMR; Phospholipid/Cholesterol Liposomes; Phospholipids - metabolism
• ISSN: 0287-4547; 1881-1361
• DOI: 10.4012/dmj.10.121

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 previously3, 12) seemed to be due to its migration into the lipid bilayer of phospholipids containing CS in erythrocyte membranes.