Abstract
To clarify the mechanism of interaction of dental adhesive monomers with biological membranes at the molecular level, we studied the interaction of 4-META and its related compounds (4-methacryloyloxyethoxy-carbonylphthalic acid 4-MET, phthalic acid and phthalic anhydride) with the dipalmitoylphosphatidylcholine (DPPC) liposome system, using NMR and DSC. Changes in NMR chemical-shifts and phase transition temperatures at pH 7.4 of DPPC liposomes induced by phthalic anhydride and 4-META were greater than those induced by phthalic acid. NMR spectra of the DPPC/4-META liposome system were similar to those of the DPPC/4-MET liposome system, suggesting hydrolysis of the anhydride moiety of 4-META in D2O. The effects of 4-META and its related compounds on human erythrocytes were also studied. 4-META and phthalic anhydride showed a greater degree of hemolysis as compared to 4-MET and phthalic acid, indicating that ionized compounds do not impregnate into biological membranes.
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