Amphotericin B dimers with bisamide linkage bearing powerful membrane-permeabilizing activity

被引:33
|
作者
Yamaji, N [1 ]
Matsumori, N [1 ]
Matsuoka, S [1 ]
Oishi, T [1 ]
Murata, M [1 ]
机构
[1] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
关键词
D O I
10.1021/ol025982m
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHIC] 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 muM) 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.
引用
收藏
页码:2087 / 2089
页数:3
相关论文
共 37 条
  • [1] An amphotericin B-ergosterol covalent conjugate with powerful membrane permeabilizing activity
    Matsumori, N
    Eiraku, N
    Matsuoka, S
    Oishi, T
    Murata, M
    Aoki, T
    Ide, T
    CHEMISTRY & BIOLOGY, 2004, 11 (05): : 673 - 679
  • [2] Activity of Membrane-Permeabilizing Lpt Peptides
    Maggi, Stefano
    Mori, Giulia
    Maglie, Luigi
    Carnuccio, Dario
    Delfino, Danila
    Della Monica, Emanuele
    Rivetti, Claudio
    Folli, Claudia
    BIOMOLECULES, 2024, 14 (08)
  • [3] Amphotericin B-phospholipid covalent conjugates: dependence of membrane-permeabilizing activity on acyl-chain length
    Matsuoka, S
    Matsumori, N
    Murata, M
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (22) : 3882 - 3884
  • [4] Amphotericin B covalent dimers bearing a tartarate linkage
    Matsumori, N
    Masuda, R
    Murata, M
    CHEMISTRY & BIODIVERSITY, 2004, 1 (02) : 346 - 352
  • [5] Membrane-permeabilizing activity of NSAIDs: a role in cardiotoxicity?
    Pereira-Leite, C.
    Figueiredo, M. C.
    Burdach, K.
    Nunes, C.
    Reis, S.
    EUROPEAN BIOPHYSICS JOURNAL WITH BIOPHYSICS LETTERS, 2019, 48 : S106 - S106
  • [6] Effects governing the activity and selectivity of membrane-permeabilizing lipopeptides
    Heerklotz, Heiko
    Patel, Hiren
    Nazari, Mozhgan
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2013, 245
  • [7] Antibacterial Activity of Membrane-Permeabilizing Bactericidal Cyclodextrin Derivatives
    Yamamura, Hatsuo
    Hagiwara, Tatsuya
    Hayashi, Yuma
    Osawa, Kayo
    Kato, Hisato
    Katsu, Takashi
    Masuda, Kazufumi
    Sumino, Ayumi
    Yamashita, Hayato
    Jinno, Ryo
    Abe, Masayuki
    Miyagawa, Atsushi
    ACS OMEGA, 2021, 6 (47): : 31831 - 31842
  • [8] Effects of lipid constituents on membrane-permeabilizing activity of amphidinols
    Morsy, Nagy
    Houdai, Toshihiro
    Konoki, Kelichi
    Matsumori, Nobuaki
    Oishi, Tohru
    Murata, Michio
    BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) : 3084 - 3090
  • [9] ZEAMATIN, AN ANTIFUNGAL PROTEIN FROM MAIZE WITH MEMBRANE-PERMEABILIZING ACTIVITY
    ROBERTS, WK
    SELITRENNIKOFF, CP
    JOURNAL OF GENERAL MICROBIOLOGY, 1990, 136 : 1771 - 1778
  • [10] Carboxyl group-modified myoglobin shows membrane-permeabilizing activity
    Shi, Yi-Jun
    Lee, Yuan-Chin
    Wang, Liang-Jun
    Chiou, Jing-Ting
    Tseng, Bo-Yang
    Chang, Long-Sen
    ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2022, 728