Issue 9, 2005
From the journal:

Organic & Biomolecular Chemistry

Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers

W. Matthew Leevy,a   Michelle E. Weber,a   Michael R. Gokel,a   George B. Hughes-Strange,a   David D. Daranciang,a   Riccardo Ferdania  and  George W. Gokel*a  

* Corresponding authors

a Departments of Chemistry and Molecular Biology & Pharmacology, Washington University School of Medicine, 660 S. Euclid Ave., Campus Box 8103, St. Louis, USA
E-mail: ggokel@molecool.wustl.edu
Fax: 314/362-9298
Tel: 314/362-9297

Abstract

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.

Graphical abstract: Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers

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Article information

DOI
https://doi.org/10.1039/B418194H
Article type
Paper
Submitted
08 Mar 2005
Accepted
11 Mar 2005
First published
11 Apr 2005

Org. Biomol. Chem., 2005,3, 1647-1652

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Correlation of bilayer membrane cation transport and biological activity in alkyl-substituted lariat ethers

W. M. Leevy, M. E. Weber, M. R. Gokel, G. B. Hughes-Strange, D. D. Daranciang, R. Ferdani and G. W. Gokel, Org. Biomol. Chem., 2005, 3, 1647 DOI: 10.1039/B418194H

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