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 liposomes/water) system. METHODS: Two experimental approaches were used, namely the pH-metric method to measure lipophilicity parameters in octanol/water and liposomes/water systems, and changes in NMR relaxation rates to validate the former method and to gain additional insights into the mechanisms of liposomes/water partitioning. RESULTS: For long-chain homologues (N-butyl to N-heptyl), the octanol/water and liposomes/water systems mostly expressed hydrophobicity. In contrast, the lipophilicity of the shorter homologues (N-methyl to N-propyl) in the two systems expressed various electrostatic and polar interactions. CONCLUSIONS: The study sheds light on the molecular interactions between zwitterionic liposomes and amphiphilic solutes in neutral and cationic form.
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 liposomes/water) system. METHODS: Two experimental approaches were used, namely the pH-metric method to measure lipophilicity parameters in octanol/water and liposomes/water systems, and changes in NMR relaxation rates to validate the former method and to gain additional insights into the mechanisms of liposomes/water partitioning. RESULTS: For long-chain homologues (N-butyl to N-heptyl), the octanol/water and liposomes/water systems mostly expressed hydrophobicity. In contrast, the lipophilicity of the shorter homologues (N-methyl to N-propyl) in the two systems expressed various electrostatic and polar interactions. CONCLUSIONS: The study sheds light on the molecular interactions between zwitterionic liposomes and amphiphilic solutes in neutral and cationic form.
Authors: C Altomare; S Cellamare; A Carotti; G Casini; M Ferappi; E Gavuzzo; F Mazza; P T Carrupt; P Gaillard; B Testa Journal: J Med Chem Date: 1995-01-06 Impact factor: 7.446
Authors: Agnes Taillardat-Bertschinger; Catherine A Marca Martinet; Pierre-Alain Carrupt; Marianne Reist; Giulia Caron; Roberta Fruttero; Bernard Testa Journal: Pharm Res Date: 2002-06 Impact factor: 4.200
Authors: G Plember van Balen; G Caron; G Ermondi; A Pagliara; T Grandi; G Bouchard; R Fruttero; P A Carrupt; B Testa Journal: Pharm Res Date: 2001-05 Impact factor: 4.200
Authors: I L Megson; S Morton; I R Greig; F A Mazzei; R A Field; A R Butler; G Caron; A Gasco; R Fruttero; D J Webb Journal: Br J Pharmacol Date: 1999-02 Impact factor: 8.739