title: Tuning nanopore formation of oligocholate macrocycles by carboxylic acid dimerization in lipid membranes.
abstract: Oligocholate macrocycles self-assemble into transmembrane nanopores by the associative interactions of water molecules inside the amphiphilic macrocycles. Macrocycles functionalized with a terephthalic acid "side chain" displayed significantly higher transport activity for glucose across lipid bilayers than the corresponding methyl ester derivative. Changing the 1,4-substitution of the dicarboxylic acid to 1,3-substitution lowered the activity. Combining the hydrophobic interactions and the hydrogen-bond-based carboxylic acid dimerization was an effective strategy to tune the structure and activity of self-assembled nanopores in lipid membranes.
authors.affiliation: Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, United States.
authors.forename: Lakmini
authors.initials: L
authors.lastname: Widanapathirana
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhao
mesh_terms: D001692:Biological Transport; D040761:Biomimetic Materials / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D020355:Cholates / Q000737:chemistry*; D019281:Dimerization; D005947:Glucose / Q000737:chemistry; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry*; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008968:Molecular Conformation; D058608:Nanopores / Q000648:ultrastructure*
chemical_list: D002264:Carboxylic Acids; D020355:Cholates; D008051:Lipid Bilayers; D047028:Macrocyclic Compounds; D005947:Glucose