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Mechanisms of liposomes/water partitioning of (p-methylbenzyl)alkylamines

Fruttero, Roberta
Caron, Giulia
Fornatto, E.
Boschi, D.
Ermondi, Giuseppe
Gasco, Alberto
Testa, Bernard
Published in Pharmaceutical Research. 1998, vol. 15, no. 9, p. 1407-1413
Abstract 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.
Keywords Alkanes/*chemistryDrug CarriersLipids/chemistryLiposomes/chemistryMagnetic Resonance SpectroscopyWater/*chemistry
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PMID: 9755893

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Deposited on : 2010-08-06

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