Membrane permeabilizing action of amphidinol 3 and theonellamide A in raft-forming lipid mixtures

College

College of Science

Department/Unit

Chemistry

Document Type

Article

Source Title

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volume

72

Issue

1-2

First Page

43

Last Page

48

Publication Date

1-1-2017

Abstract

Amphidinol 3 (AM3) and theonellamide A (TNM-A) are potent antifungal compounds produced by the dinoflagellate Amphidinium klebsii and the sponge Theonella spp., respectively. Both of these metabolites have been demonstrated to interact with membrane lipids ultimately resulting in a compromised bilayer integrity. In this report, the activity of AM3 and TNM-A in ternary lipid mixtures composed of 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (POPC):brain sphingomyelin:cholesterol at a mole ratio of 1:1:1 or 3:1:1 exhibiting lipid rafts coexistence is presented. It was found that AM3 has a more extensive membrane permeabilizing activity compared with TNM-A in these membrane mimics, which was almost complete at 15 μM. The extent of their activity nevertheless is similar to the previously reported binary system of POPC and cholesterol, suggesting that phase separation has neither beneficial nor detrimental effects in their ability to disrupt the lipid bilayer. © 2017 Walter de Gruyter GmbH, Berlin/Boston.

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Digitial Object Identifier (DOI)

10.1515/znc-2016-0043

Disciplines

Chemistry

Keywords

Antifungal agents; Lipid membranes

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