Phospholipid phase transitions. Effects of n-alcohols, n-monocarboxylic acids, phenylalkyl alcohols and quaternary ammonium compounds.
The interactions of a series of alcohols, acids and quaternary ammonium salts with a phosphatidylcholine-water model biomembrane (dipalmitoyl phosphatidycholine) system have been studied using differential scanning calorimetry. In particular the effects of these molecules upon the lipid endothermic phase transitions were investigated over a range of concentrations. A variety of effects was observed. (a) Those molecules which shift or broaden the main lipid transition can also remove the pretransition endotherm. (b) n-Alcohols and n-monocarboxylic acids containing the same number of carbon atoms have very similar effects at molar concentrations up to 40%. Those molecules containing 12 or more carbon atoms raise the main lipid phase transition whilst those molecules containing 10 or less carbon atoms lower this transition temperature. (c) The phase diagram of stearoyl alcohol in the phosphatidylcholine-water system shows the formation of lipid-alcohol complexes. (d) Alkyl trimethyl ammonium bromides showed behaviour which differs considerably from n-alcohols and n-carboxylic acids of the same chain length. (e) Other alkyltrialkyl and tetraalkylammonium bromides show that a variety of effects on the lipid phase transition can be obtained. (f) With the homologous series of phenyl-alkyl alcohols from benzyl alcohol to 4-phenyl butanol increasing the number of methylenes between the terminal OH and the benzene ring leads to greater interaction between solute and bilayer. The range of different effects obtained with the compounds studied offers a means for introducing various degrees and types of perturbation into membrane systems.
D000438:Alcohols; D000473:Alkanes; D001592:Benzyl Alcohols; D002151:Calorimetry; D002264:Carboxylic Acids; D008567:Membranes, Artificial; D013329:Structure-Activity Relationship; D013696:Temperature
D000438:Alcohols; D000473:Alkanes; D001592:Benzyl Alcohols; D002264:Carboxylic Acids; D008567:Membranes, Artificial