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 journalArticle

32 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 languageEnglish
Pages (from-to)2087-2089
Number of pages3
JournalOrganic Letters
Volume4
Issue number12
DOIs
Publication statusPublished - Jun 13 2002
Externally publishedYes

Fingerprint

Bearings (structural)
1,6-diaminohexane
Amphotericin B
linkages
Dimers
dimers
membranes
Membranes
Sterols
Carboxylic Acids
Phosphatidylcholines
Ion Channels
Liposomes
Ions
carboxylic acids
Fluxes
Derivatives
matrices
ions

All Science Journal Classification (ASJC) codes

  • Molecular Medicine

Cite this

Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity. / Yamaji, Nahoko; Matsumori, Nobuaki; Matsuoka, Shigeru; Oishi, Tohru; Murata, Michio.

In: Organic Letters, Vol. 4, No. 12, 13.06.2002, p. 2087-2089.

Research output: Contribution to journalArticle

Yamaji, Nahoko ; Matsumori, Nobuaki ; Matsuoka, Shigeru ; Oishi, Tohru ; Murata, Michio. / Amphotericin B Dimers with Bisamide Linkage Bearing Powerful Membrane-Permeabilizing Activity. In: Organic Letters. 2002 ; Vol. 4, No. 12. pp. 2087-2089.
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