Biphasic effects of acetaldehyde-biogenic amine condensation products on membrane fluidity

Abstract

Abstract I have studied the effects of four acetaldehyde-biogenic amine condensation products on membrane fluidity of liposomes, consisting of 1-palmitoyl-2-oleoylphosphatidylcholine and cholesterol, by measuring fluorescence polarization using different probes. The condensation products were 1-methyl-1,2,3,4-tetrahydro-β-carboline (MTBC), 6-hydroxy-1-methyl-1,2,3,4-tetrahydro-β-carboline (6-OH-MTBC), 3-carboxy-1-methyl-1,2,3,4-tetrahydro-β-carboline (3-C-MTBC) and 6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline (salsolinol). They changed the fluidity of the hydrophobic and hydrophilic regions of liposomal membranes at micromolar levels almost corresponding to their antibacterial and antiplatelet concentrations, but their membrane effects varied by structure, concentration and membrane lipid composition. MTBC and salsolinol showed biphasic effects on the inner layers of membranes to enhance the fluidity at 250–1000 μM and reduce the fluidity at 50–100 μM, whereas both of them fluidized the outer layers of the membranes. 3-C-MTBC concentration-dependently fluidized both layers of membranes. 6-OH-MTBC most weakly enhanced and reduced the fluidity of the outer and inner layers, respectively. The membrane effect of MTBC was the greatest of the four condensation products. MTBC (50–1000 nM) significantly reduced the fluidity by exclusively acting on the membrane core, but was less effective in fluidizing the membrane surface. However, the others were not active at low nanomolar levels. The membrane effects may be partly responsible for the antibacterial and antiplatelet actions of the acetaldehyde-biogenic amine condensation products, although they do not appear to be simple membrane fluidizers.