Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity

Nahoko Yamaji; Nobuaki Matsumori; Shigeru Matsuoka; Tohru Oishi; Michio Murata

doi:10.1021/ol025982m

Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity

Nahoko Yamaji, Nobuaki Matsumori, Shigeru Matsuoka, Tohru Oishi, Michio Murata

Research output: Contribution to journal › Article › peer-review

35 Citations (Scopus)

Abstract

(Matrix Presented) Covalently linked dimers of amphotericin B were prepared by cross-linking its carboxylic acid. Among these, a dimer with a linkage of 1,6-hexanediamine revealed potent hemolytic activity (EC₅₀,0.25 μM) while its N-acetyl derivative gave rise to large K⁺ ion flux in phosphatidylcholine liposomes, regardless of the presence or absence of sterols, suggesting that the dimers may serve as a tool for elucidating the structure of the ion channel assemblage formed by amphotericin B.

Original language	English
Pages (from-to)	2087-2089
Number of pages	3
Journal	Organic letters
Volume	4
Issue number	12
DOIs	https://doi.org/10.1021/ol025982m
Publication status	Published - Jun 13 2002
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol025982m

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abstract = "(Matrix Presented) Covalently linked dimers of amphotericin B were prepared by cross-linking its carboxylic acid. Among these, a dimer with a linkage of 1,6-hexanediamine revealed potent hemolytic activity (EC50,0.25 μM) while its N-acetyl derivative gave rise to large K+ ion flux in phosphatidylcholine liposomes, regardless of the presence or absence of sterols, suggesting that the dimers may serve as a tool for elucidating the structure of the ion channel assemblage formed by amphotericin B.",

author = "Nahoko Yamaji and Nobuaki Matsumori and Shigeru Matsuoka and Tohru Oishi and Michio Murata",

year = "2002",

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T1 - Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity

AU - Yamaji, Nahoko

AU - Matsumori, Nobuaki

AU - Matsuoka, Shigeru

AU - Oishi, Tohru

AU - Murata, Michio

PY - 2002/6/13

Y1 - 2002/6/13

N2 - (Matrix Presented) Covalently linked dimers of amphotericin B were prepared by cross-linking its carboxylic acid. Among these, a dimer with a linkage of 1,6-hexanediamine revealed potent hemolytic activity (EC50,0.25 μM) while its N-acetyl derivative gave rise to large K+ ion flux in phosphatidylcholine liposomes, regardless of the presence or absence of sterols, suggesting that the dimers may serve as a tool for elucidating the structure of the ion channel assemblage formed by amphotericin B.

AB - (Matrix Presented) Covalently linked dimers of amphotericin B were prepared by cross-linking its carboxylic acid. Among these, a dimer with a linkage of 1,6-hexanediamine revealed potent hemolytic activity (EC50,0.25 μM) while its N-acetyl derivative gave rise to large K+ ion flux in phosphatidylcholine liposomes, regardless of the presence or absence of sterols, suggesting that the dimers may serve as a tool for elucidating the structure of the ion channel assemblage formed by amphotericin B.

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Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity

Abstract

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