Drug–Membrane Interaction on Immobilized Liposome Chromatography Compared to Immobilized Artificial Membrane (IAM), Liposome/Water, and Octan‐1‐ol/Water Systems

Abstract

The objective of this study was to investigate drug -membrane interaction by immobilized liposome chromatography (ILC; expressed as lipophilicity index log K s ) and the comparison with lipophilicity indices obtained by liposome/H 2 O, octan-1-ol/H 2 O, and immobilized artificial membrane (IAM) systems. A set of structurally diverse monofunctional compounds and drugs (nonsteroidal antiinflammatory drugs and b-blockers) were selected in this study. This set of solutes consists of basic or acidic functionalities which are positively or negatively charged at physiological pH 7.4. No correlation was found between log K s from ILC and lipophilicity indices from any of the other membrane model systems for the whole set of compounds. For structurally related compounds, significant correlations could be established between log K s from ILC and lipophilicity indices from IAM chromatography and octan-1-ol/H 2 O. However, ILC and liposome/H 2 O systems only yield parallel partitioning information for structurally related large molecules. For hydrophilic compounds, the balance between electrostatic and hydrophobic interactions dominating drug partitioning is different in these two systems.

Lipophilicity and Its Relationship with Passive Drug Permeation

“…No significant correlation was found between log K s and log D from liposome/water partitioning system, log k IAMw or log D oct for structurally unrelated compounds (104,108).…”

Cholesterol – a biological compound as a building block in bionanotechnology

“…uptake of the drug through the cell membrane) is the rst step of the drug's action. 175,181,183 CAPILLARY ELECTROPHORESIS. CE is an analytical technique that separates ions based on their electrophoretic mobility with the use of an applied voltage.…”

Preparation and characterization of phosphatidylcholine‐coated zirconia–magnesia stationary phase for artificial membrane chromatography

“…But the total coating amounts were only slightly different, 121.85 and 112.21 μmol PC were coated on PCZM and PCS, respectively (see Table 1). The retention time of benzene and toluene on PCZM was longer than that on PCS, but the difference was slight, which also illustrated that the total amount of PC coated on two chromatography columns was slightly different because the retention time of the solute was in proportion to the amount of coated PC 11.…”

“…When the artificial PC membrane chromatography was used for screening drugs, the strong lipophilic solutes had long retention times or were not eluted out at all by using pure buffer (no organic solvent) as the mobile phase, which limited its application. In order to resolve this problem, Beigi and Lundahl tried to use a small column to reduce the amount of immobilized liposome, which would result in the decrease in the retention time of strong lipophilic solutes 11. Compared with the results on the normal size columns, it is shown that this method was successful.…”

“…The other two types (immobilized liposome and artificial membrane) not only simulate structure of real membrane but also have some advantages, i.e . good stability and easy to be prepared, so that they have been used in wide fields of screening drug 9–13, studying affinity characteristics of proteins on membrane, investigating interaction between peptides (or proteins) and membrane 14–17, and separating membrane proteins 18–20, nuclei acids and isomers 1, 21.…”