Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

Toshihiro Houdai, Shigeru Matsuoka, Nagy Morsy, Nobuaki Matsumori, Masayuki Satake, Michio Murata

Research output: Contribution to journalArticle

50 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2795-2802
Number of pages8
JournalTetrahedron
Volume61
Issue number11
DOIs
Publication statusPublished - Mar 14 2005
Externally publishedYes

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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