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.
Fruttero
R
R
Dipartimento di Scienza e Tecnologia del Farmaco, Torino, Italy.
Caron
G
G
Fornatto
E
E
Boschi
D
D
Ermondi
G
G
Gasco
A
A
Carrupt
P A
PA
Testa
B
B
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