Mechanisms of liposomes/water partitioning of (p-methylbenzyl)alkylamines.
OBJECTIVE
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.
Dipartimento di Scienza e Tecnologia del Farmaco, Torino, Italy.
R
R
Fruttero
G
G
Caron
E
E
Fornatto
D
D
Boschi
G
G
Ermondi
A
A
Gasco
P A
PA
Carrupt
B
B
Testa
D020003:1-Octanol / Q000737:chemistry*; D000473:Alkanes / Q000737:chemistry*; D004337:Drug Carriers; D008055:Lipids / Q000737:chemistry; D008081:Liposomes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D014867:Water / Q000737:chemistry*
D000473:Alkanes; D004337:Drug Carriers; D008055:Lipids; D008081:Liposomes; D014867:Water; D020003:1-Octanol