Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers

Rafael Atillo Espiritu, Nobuaki Matsumori, Masashi Tsuda, Michio Murata

研究成果: Contribution to journalArticle査読

24 被引用数 (Scopus)

抄録

Amphidinol 3 (AM3), a polyhydroxy-polyene metabolite from the dinoflagellate Amphidinium klebsii, possesses potent antifungal activity. Although AM3 permeabilizes phospholipid membranes only in the presence of sterol, the detailed molecular basis by which AM3 recognizes sterols in membranes remains unknown. Here, we investigated the molecular interaction between sterols and AM3 in membranes from the viewpoint of stereospecific molecular recognition using ergosterol, cholesterol, and epicholesterol, which is the 3-OH epimer of cholesterol. Dye leakage assays, surface plasmon resonance experiments, 2H and 31P NMR measurements, and microscopic observations revealed that AM3 directly interacts with membrane sterols through the strict molecular recognition of the stereochemistry of the sterol 3-OH group. The direct interaction enhances the membrane binding efficiency of AM3, which subsequently permeabilizes membranes without altering membrane integrity.

本文言語英語
ページ(範囲)3287-3293
ページ数7
ジャーナルBiochemistry
53
20
DOI
出版ステータス出版済み - 5 27 2014
外部発表はい

All Science Journal Classification (ASJC) codes

  • 生化学

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