title: Pore formation in phospholipid bilayers by amphiphilic cavitands.
abstract: Five new cavitands were prepared that have four pendant n-undecyl chains and "headgroups" connected by 2-carbon spacers. The headgroups were ~OCH(2)CONH-Ala-OCH(3), 1; ~OCH(2)CONH-Phe-OCH(3), 2; ~OCH(2)CONH-Ala-OH, 3; ~OCH(2)CONH-Phe-OH, 4; and ~OCH(2)CONHCH(2)CH(2)-thyminyl, 5. Pore formation by each cavitand was studied by use of the planar bilayer conductance experiment. All five compounds were found to form pores in asolectin bialyer membranes. Compounds 1-3 behaved in a generally similar fashion and exhibited open-close dynamics. Compounds 4 and 5 formed pores more rapidly, were more dynamic, and led more quickly to membrane rupture. Differences in the ion transport activity are rationalized in terms of structure and aggregate cavitand assemblies.
authors.affiliation: School of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban, 4000, South Africa.
authors.forename: Iman
authors.initials: I
authors.lastname: Elidrisi
authors.forename: Saeedeh
authors.initials: S
authors.lastname: Negin
authors.forename: Pralav V
authors.initials: PV
authors.lastname: Bhatt
authors.forename: Thavendran
authors.initials: T
authors.lastname: Govender
authors.forename: Hendrick G
authors.initials: HG
authors.lastname: Kruger
authors.forename: George W
authors.initials: GW
authors.lastname: Gokel
authors.forename: Glenn E M
authors.initials: GE
authors.lastname: Maguire
mesh_terms: D002627:Chemistry, Physical; D004553:Electric Conductivity; D004988:Ethers, Cyclic / Q000737:chemistry* / Q000378:metabolism; D007473:Ion Channels / Q000737:chemistry* / Q000378:metabolism; D017136:Ion Transport; D008051:Lipid Bilayers / Q000737:chemistry* / Q000378:metabolism; D008564:Membrane Potentials; D018716:Molecular Mimicry; D010713:Phosphatidylcholines / Q000737:chemistry / Q000378:metabolism; D012118:Resorcinols / Q000737:chemistry* / Q000378:metabolism; D013501:Surface-Active Agents / Q000737:chemistry* / Q000378:metabolism
chemical_list: D004988:Ethers, Cyclic; D007473:Ion Channels; D008051:Lipid Bilayers; D010713:Phosphatidylcholines; D012118:Resorcinols; D013501:Surface-Active Agents; C442939:cavitand; C024990:asolectin