Abstract
The anti-inflammatory drug, β-glycyrrhizinic acid 20-methyl ester (GMe), was converted to cationic variants (CGRs) by derivatizing diglucronic carboxyl groups with 2- (N-ethyl-, N-butyl- and N-benzyl-N, N-dimetylammonio) ethylamines. Critical micellar concentrations, ranging from 0.40.7mM, were essentially independent of solution pH from 5 to 9 and approximated that of GMe (0.3mM at pH 57.4). Transferability (%) of CGRs from water to 1-octanol phase at higher-than-neutral pH was much more than that of GMe or β-glycyrrhizinic acid (GL) : CGBu (55) >CGBn (20) >CGEt (15) >GMe (10) >GL (0). CGRs remarkably accelerated the release of the carboxyfluorescein (CF) trapped inside DPPC vesicles with no costing significant damage to cell membranes. The CF-releasing mechanism was examined kinetically by differential scanning calorimetory, light-scattering and electron microcopy.
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