Influence of local and neutral anaesthetics on the polymorphic phase preferences of egg yolk phosphatidylethanolamine.
(1) The polymorphic phase preferences of egg phosphatidylethanolamine have been examined in the presence of normal alcohols and alkanes of varying chain length, as well as charged amine anaesthetics. (2) It is shown that the charged anaesthetics, ethanol and butanol can stabilize a bilayer arrangement for egg phosphatidylethanolamine. In contrast, longer chain (C greater than or equal to 6) normal alcohols and alkanes induce the hexagonal (HII) phase. (3) The relative potency of local anaesthetics in vitro (chlorpromazine, dibucaine, tetracaine and procaine) is mirrored by their relative ability to stabilize bilayer structure for hydrated egg phosphatidylethanolamine. Further, the aqueous concentrations of anaesthetic required to affect phospholipid polymorphism is sensitive to the lipid composition. For example, the inclusion of 20 mol% egg phosphatidylserine in egg phosphatidylethanolamine dispersions can reduce the aqueous concentrations of dibucaine required to induce appreciable bilayer stabilization effects from 5.0 mM to 0.5 mM. (4) It is suggested that the ability of amphipathic molecules such as anaesthetics to influence phosphatidylethanolamine polymorphism arises from their molecular shape. The possibility that anaesthetic molecules may exert their effects by virtue of this shape property is raised.
D000777:Anesthetics / Q000494:pharmacology*; D000440:Butanols / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D002746:Chlorpromazine / Q000494:pharmacology; D003992:Dibucaine / Q000494:pharmacology; D000431:Ethanol / Q000494:pharmacology; D008051:Lipid Bilayers; D010714:Phosphatidylethanolamines; D011343:Procaine / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013696:Temperature; D013748:Tetracaine / Q000494:pharmacology
D000777:Anesthetics; D000440:Butanols; D008051:Lipid Bilayers; D010714:Phosphatidylethanolamines; D013748:Tetracaine; D000431:Ethanol; D011343:Procaine; D003992:Dibucaine; D002746:Chlorpromazine