Issue 19, 2005
From the journal:

Organic & Biomolecular Chemistry

Structure–activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

W. Matthew Leevy,a   Seth T. Gammon,b   Tatiana Levchenko,e   David D. Daranciang,a   Oscar Murillo,a   Vladimir Torchilin,e   David Piwnica-Worms,ab   James E. Huettnerc  and  George W. Gokel*ad  

* Corresponding authors

a Department of Molecular Biology & Pharmacology, Washington University School of Medicine, Campus Box 8103, 660 S. Euclid Avenue, St. Louis, MO, USA
E-mail: ggokel@wustl.edu
Tel: +1 314 362 9297

b Departments of Radiology, Washington University School of Medicine, Campus Box 8103, 660 S. Euclid Avenue, St. Louis, MO, USA

c Departments of Cell Biology and Physiology, Washington University School of Medicine, Campus Box 8103, 660 S. Euclid Avenue, St. Louis, MO, USA

d Department of Chemistry, Washington University, 1 Brookings Drive, St. Louis, MO, USA

e Department of Pharmaceutical Sciences, Bouve College of Health Sciences, Northeastern University, Boston, MA, USA

Abstract

Hydraphile compounds are shown to be cytotoxic to Gram-negative and Gram-positive bacteria, yeast, and mammalian cells. Their cellular toxicity compares favorably with other synthetic ionophores and rivals that potency of natural antibiotics. The effects of structural variations on toxicity are described. The effects of these variations correlate well with previous studies of ion transport in liposomes. Whole cell patch clamping with mammalian cells confirms a channel mechanism in living cells suggesting that this family may comprise novel and flexible pharmacological agents.

Graphical abstract: Structure–activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

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Article information

DOI
https://doi.org/10.1039/B508157B
Article type
Paper
Submitted
09 Jun 2005
Accepted
11 Aug 2005
First published
26 Aug 2005

Org. Biomol. Chem., 2005,3, 3544-3550

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Structure–activity relationships, kinetics, selectivity, and mechanistic studies of synthetic hydraphile channels in bacterial and mammalian cells

W. M. Leevy, S. T. Gammon, T. Levchenko, D. D. Daranciang, O. Murillo, V. Torchilin, D. Piwnica-Worms, J. E. Huettner and G. W. Gokel, Org. Biomol. Chem., 2005, 3, 3544 DOI: 10.1039/B508157B

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