title: Water-templated transmembrane nanopores from shape-persistent oligocholate macrocycles.
abstract: Hydrophobic interactions normally are not considered a major driving force for self-assembling in a hydrophobic environment. When macrocyclic oligocholates were placed within lipid membranes, however, the macrocycles pulled water molecules from the aqueous phase into their hydrophilic internal cavities. These water molecules had strong tendencies to aggregate in a hydrophobic environment and templated the macrocycles to self-assemble into transmembrane nanopores. This counterintuitive hydrophobic effect resulted in some highly unusual transport behavior. Cholesterol normally increases the hydrophobicity of lipid membranes and makes them less permeable to hydrophilic molecules. The permeability of glucose across the oligocholate-containing membranes, however, increased significantly upon the inclusion of cholesterol. Large hydrophilic molecules tend to have difficulty traversing a hydrophobic barrier. The cyclic cholate tetramer, however, was more effective at permeating maltotriose than glucose.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA.
authors.forename: Hongkwan
authors.initials: H
authors.lastname: Cho
authors.forename: Lakmini
authors.initials: L
authors.lastname: Widanapathirana
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D002462:Cell Membrane / Q000737:chemistry* / Q000378:metabolism; D020355:Cholates / Q000737:chemistry* / Q000378:metabolism; D002784:Cholesterol / Q000378:metabolism; D005947:Glucose / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D047028:Macrocyclic Compounds / Q000737:chemistry* / Q000378:metabolism; D008958:Models, Molecular; D008968:Molecular Conformation; D058608:Nanopores; D010539:Permeability; D010713:Phosphatidylcholines / Q000737:chemistry / Q000378:metabolism; D010715:Phosphatidylglycerols / Q000737:chemistry / Q000378:metabolism; D053835:Unilamellar Liposomes / Q000737:chemistry / Q000378:metabolism; D014867:Water / Q000737:chemistry* / Q000378:metabolism
chemical_list: D020355:Cholates; D047028:Macrocyclic Compounds; D010713:Phosphatidylcholines; D010715:Phosphatidylglycerols; D053835:Unilamellar Liposomes; D014867:Water; C060037:1-palmitoyl-2-oleoylglycero-3-phosphoglycerol; D002784:Cholesterol; D005947:Glucose; C028694:1-palmitoyl-2-oleoylphosphatidylcholine