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

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...

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Main Authors: Espiritu, Rafael Atillo, Matsumori, Nobuaki, Tsuda, Masashi, Murata, Michio
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Published: Animo Repository 2014
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Online Access:https://animorepository.dlsu.edu.ph/faculty_research/5119
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Institution: De La Salle University
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spelling oai:animorepository.dlsu.edu.ph:faculty_research-58142022-03-23T05:51:42Z Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers Espiritu, Rafael Atillo Matsumori, Nobuaki Tsuda, Masashi Murata, Michio 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. 2014-01-01T08:00:00Z text https://animorepository.dlsu.edu.ph/faculty_research/5119 info:doi/10.1021/bi5002932 Faculty Research Work Animo Repository Dinoflagellates Antifungal agents Sterols Chemical reactions Chemistry
institution De La Salle University
building De La Salle University Library
continent Asia
country Philippines
Philippines
content_provider De La Salle University Library
collection DLSU Institutional Repository
topic Dinoflagellates
Antifungal agents
Sterols
Chemical reactions
Chemistry
spellingShingle Dinoflagellates
Antifungal agents
Sterols
Chemical reactions
Chemistry
Espiritu, Rafael Atillo
Matsumori, Nobuaki
Tsuda, Masashi
Murata, Michio
Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
description 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.
format text
author Espiritu, Rafael Atillo
Matsumori, Nobuaki
Tsuda, Masashi
Murata, Michio
author_facet Espiritu, Rafael Atillo
Matsumori, Nobuaki
Tsuda, Masashi
Murata, Michio
author_sort Espiritu, Rafael Atillo
title Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
title_short Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
title_full Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
title_fullStr Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
title_full_unstemmed Direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
title_sort direct and stereospecific interaction of amphidinol 3 with sterol in lipid bilayers
publisher Animo Repository
publishDate 2014
url https://animorepository.dlsu.edu.ph/faculty_research/5119
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