MECHANISMS OF LIPOSOMES WATER PARTITIONING OF (P-METHYLBENZYL)ALKYLAMINES/

Purpose. The objective of this study was to compare and interpret the variations in lipophilicity of homologous (p-methylbenzyl)alkylamines (MBAAs) in isotropic (octanol/water) and anisotropic (zwitterionic lip osomes/water) system. Methods. Two experimental approaches were used, namely the pH metric method to measure lipophilicity parameters in oct anol/water and liposomes/water systems, and changes in NMR relaxation rates to validate the former method and to gain additional insights in to the mechanisms of liposomes/water partitioning. Results. For long-c hain homologues (N-butyl to N-heptyl), the octanol/water and liposomes /water systems mostly expressed hydrophobicity. In contrast, the lipop hilicity of the shorter homologues (N-methyl to N-propyl) in the two s ystems expressed various electrostatic and polar interactions. Conclus ions. The study sheds light on the molecular interactions between zwit terionic liposomes and amphiphilic solutes in neutral and cationic for m.