Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers.
Dialkyldiaza-18-crown-6 lariat ethers having twin n-octyl, n-decyl, n-dodecyl, n-tetradecyl, n-hexadecyl, 1-oxodecyl and 1-oxododecyl side arms were prepared and studied. Cation transport in liposomes mediated by these compounds showed discontinuous activity that correlated with toxicity to the bacteria E. coli and B. Subtilis, and the yeast S. Cerevisiae. Transport, toxicity and membrane depolarization studies all suggest that side chain length affords very different interactions in a bilayer membrane compared with bulk phases. An explanation for activity in terms of carrier transport and restricted transverse relaxation is proposed.
Leevy
W Matthew
WM
Departments of Chemistry and Molecular Biology & Pharmacology, Washington University School of Medicine, 660 S. Euclid Ave., Campus Box 8103, St. Louis, MO 63110, USA.
Weber
Michelle E
ME
Gokel
Michael R
MR
Hughes-Strange
George B
GB
Daranciang
David D
DD
Ferdani
Riccardo
R
Gokel
George W
GW
D000900:Anti-Bacterial Agents / Q000494:pharmacology; D002412:Cations; D004987:Ethers / Q000494:pharmacology*; D017136:Ion Transport; D008051:Lipid Bilayers; D013050:Spectrometry, Fluorescence
D000900:Anti-Bacterial Agents; D002412:Cations; D004987:Ethers; D008051:Lipid Bilayers