title: Passive permeability of dihexadecylphosphate vesicles altered by aliphatic alcohols and omega-diols.
abstract: Alcohols act as anaesthetics only up to a certain chain length, beyond which their biological activity disappears. Although the molecular nature of general target sites remains unknown, presently available data support the hypothesis that this 'cut-off' in anaesthetic activity could be due to a corresponding cut-off in the absorption of long-chain alcohols into lipid-bilayer portions of nerve membranes. To test this hypothesis, we developed a method based on leakage of Ru(bpy)3(2+) ions across the membrane of dihexadecylphosphate (DHP) vesicles induced by aliphatic alcohols (C1 to C18) and some of their omega-diol. The permeant effects of aliphatic linear alcohols expressed as PD50 values rise to a maximum for n-dodecanol (PD50 = 2 x 10(-3) M 1(-1]. Dodecanol was found to be the alcohol which presents the greatest anaesthetic potency among the series of linear aliphatic alcohols (cut-off anaesthetic effect). The results are discussed in terms of the structural physicochemical and geometrical characteristics of the permeating alcohols.
authors.affiliation: Centre de Biochimie et de Biologie Moléculaire, CNRS, Marseille, France.
authors.forename: M
authors.initials: M
authors.lastname: Castaing
authors.forename: J
authors.initials: J
authors.lastname: Jallon
authors.forename: M
authors.initials: M
authors.lastname: Camplo
authors.forename: J L
authors.initials: JL
authors.lastname: Kraus
mesh_terms: D000438:Alcohols / Q000737:chemistry / Q000494:pharmacology*; D000777:Anesthetics / Q000494:pharmacology*; D002463:Cell Membrane Permeability / Q000187:drug effects* / Q000502:physiology; D008081:Liposomes / Q000737:chemistry*; D008970:Molecular Weight; D010755:Organophosphates / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000777:Anesthetics; D008081:Liposomes; D010755:Organophosphates; C002290:dicetylphosphate