Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

Amphidinols are a unique dinoflagellate metabolite with potent antifungal activity. We examined membrane permeabilizing action by amphidinol analogues with structural variations in polyhydroxy and polyene moieties. Consequently, the polyene and polyhydroxy moieties turned out to play important roles...

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Bibliographic Details
Published in:Tetrahedron 2005-03, Vol.61 (11), p.2795-2802
Main Authors: Houdai, Toshihiro, Matsuoka, Shigeru, Morsy, Nagy, Matsumori, Nobuaki, Satake, Masayuki, Murata, Michio
Format: Article
Language:English
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Amphidinol membrane-permeabilization
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Summary:Amphidinols are a unique dinoflagellate metabolite with potent antifungal activity. We examined membrane permeabilizing action by amphidinol analogues with structural variations in polyhydroxy and polyene moieties. Consequently, the polyene and polyhydroxy moieties turned out to play important roles in binding to lipid bilayer membrane and in forming ion-permeable pore/lesion across membrane, respectively. NMR-constrained modeling experiments have revealed for the fist time that amphidinols in membrane generally take a hairpin configuration, which plausibly accounts for their potent antifungal and other membrane permeabilizing activities. Graphical Abstract
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2005.01.069