Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

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

doi:10.1016/j.tet.2005.01.069

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 journal › Article › peer-review

65 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 language	English
Pages (from-to)	2795-2802
Number of pages	8
Journal	Tetrahedron
Volume	61
Issue number	11
DOIs	https://doi.org/10.1016/j.tet.2005.01.069
Publication status	Published - Mar 14 2005
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2005.01.069

Cite this

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title = "Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities",

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.",

author = "Toshihiro Houdai and Shigeru Matsuoka and Nagy Morsy and Nobuaki Matsumori and Masayuki Satake and Michio Murata",

note = "Funding Information: We are grateful to Seiji Adachi in Department of Chemistry, Osaka University for measuring NMR spectra; to Megumi Mori and Saori Seki in our laboratory for their help in culturing dinoflagellates; and to Prof. Tohru Oishi in our laboratory for discussion and suggestions. This study was supported by Yamada Science Foundation and by a Grant-In-Aide for Scientific Research on Priority Area (A) (No. 12045243) from MEXT, Japan.",

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doi = "10.1016/j.tet.2005.01.069",

language = "English",

volume = "61",

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journal = "Tetrahedron",

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T1 - Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

AU - Houdai, Toshihiro

AU - Matsuoka, Shigeru

AU - Morsy, Nagy

AU - Matsumori, Nobuaki

AU - Satake, Masayuki

AU - Murata, Michio

N1 - Funding Information: We are grateful to Seiji Adachi in Department of Chemistry, Osaka University for measuring NMR spectra; to Megumi Mori and Saori Seki in our laboratory for their help in culturing dinoflagellates; and to Prof. Tohru Oishi in our laboratory for discussion and suggestions. This study was supported by Yamada Science Foundation and by a Grant-In-Aide for Scientific Research on Priority Area (A) (No. 12045243) from MEXT, Japan.

PY - 2005/3/14

Y1 - 2005/3/14

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/14244268422

UR - https://www.scopus.com/pages/publications/14244268422#tab=citedBy

U2 - 10.1016/j.tet.2005.01.069

DO - 10.1016/j.tet.2005.01.069

M3 - Article

AN - SCOPUS:14244268422

SN - 0040-4020

VL - 61

SP - 2795

EP - 2802

JO - Tetrahedron

JF - Tetrahedron

IS - 11

ER -

Hairpin conformation of amphidinols possibly accounting for potent membrane permeabilizing activities

Abstract

All Science Journal Classification (ASJC) codes

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