Abstract

Interactions of two adamantyl molecules: 3-(adamantan-1-yl)propan-1-aminium chloride (compound A) and 1-hydroxyadamantan (compound B) with multilayer liposomes composed of L-α-phosphatidylcholine, cholesterol and dicetylphosphate, spin labelled with n-doxylstearic acids (n = 5, 7, 10, 12, 16) were investigated. In the presence of aminium salt (A) or alcohol (B) the increased dynamics of 5-doxylstearic acids and 16-doxylstearic acids in the multilamellar liposomes were determined in the temperature range from 250 K to 295 K. The increased dynamics of 5-doxylstearic acids suggested that both adamantyl compounds influenced molecular motions in the interfacial region of the liposome. The increased motional properties of 16-doxylstearic acids, located in the core of the multilamellar liposomes, suggested that both adamantyl compounds induced the structural changes in the hydrophobic core as well.

Highlights

  • Multidimensional value of adamantyl group in the drug design has been pointed out in the several recent review papers.[1]

  • In order to be close to the cell surface polarity the negatively charged multilamelar liposomes composed of egg-phosphatidylcholine, cholesterol and dicethylphosphate, spin labelled with n-doxylstearic acids (n = 5, 10, 16) were used

  • The results demonstrated preference for the interfacial region of the bilayer for both protonated as well as neutral forms, while permeant species were only the small number of the neutral forms of all the three adamantanes

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Summary

Introduction

Multidimensional value of adamantyl group in the drug design has been pointed out in the several recent review papers.[1]. In order to get more information on the possible role of the adamantyl moiety in interactions with the liposomes that contain cholesterol and negative charge, two different types of adamantyl molecules: 3-(adamantan-1-yl)propan-1-aminium chloride (Figure 1, A) and 1-hydroxyadamantan (Figure 1, B) were studied in this work.

Results
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