Sterol effect on interaction between amphidinol 3 and liposomal membrane as evidenced by surface plasmon resonance

被引：27
作者：
Swasono, Respati T. [1 ]
Mouri, Ryota [1 ]
Morsy, Nagy [1 ]
Matsumori, Nobuaki [1 ]
Oishi, Tohru [1 ]
Murata, Michio [1 ]
机构：
[1] Osaka Univ, Grad Sch Sci, Dept Chem, Osaka 5600043, Japan
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2010年 / 20卷 / 07期
关键词：
Amphidinol; Surface plasmon resonance; Cholesterol; Ergosterol; TRUNCATED POLYHYDROXYL CHAIN; MARINE DINOFLAGELLATE; ANTIFUNGAL; COMPOUND;
D O I：
10.1016/j.bmcl.2010.02.025
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
The affinity of amphidinol 3 (AM3) to phospholipid membranes in the presence and absence of sterol was examined by surface plasmon resonance (SPR) experiments. The results showed that AM3 has 1000 and 5300 times higher affinity for cholesterol-and ergosterol-containing liposomes, respectively, than those without sterol. The two-state reaction model well reproduced the sensor grams, which indicated that the interaction is composed of two steps, which correspond to binding to the membrane and internalization to form stable complexes. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码：2215 / 2218
页数：4
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共 27 条
  • [11] Luteophanols B and C, new polyhydroxyl compounds from marine dinoflagellate Amphidinium sp
    Kubota, T
    Tsuda, M
    Doi, Y
    Takahashi, A
    Nakamichi, H
    Ishibashi, M
    Fukushi, E
    Kawabata, J
    Kobayashi, J
    [J]. TETRAHEDRON, 1998, 54 (48) : 14455 - 14464
  • [12] Amphezonol A, a novel polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp.
    Kubota, Takaaki
    Sakuma, Yusuke
    Shimbo, Kazutaka
    Tsuda, Masashi
    Nakano, Michiko
    Uozumi, Yasuhiro
    Kobayashi, Jun'ichi
    [J]. TETRAHEDRON LETTERS, 2006, 47 (26) : 4369 - 4371
  • [13] Luteophanol D, new polyhydroxyl metabolite from marine dinoflagellate Amphidinium sp.
    Kubota, Takaaki
    Takahashi, Ayako
    Tsuda, Masashi
    Kobayashi, Jun'ichi
    [J]. MARINE DRUGS, 2005, 3 (04): : 113 - 118
  • [14] Isolation and structure elucidation of a new amphidinol with a truncated polyhydroxyl chain from Amphidinium klebsii
    Morsy, N
    Matsuoka, S
    Houdai, T
    Matsumori, N
    Adachi, S
    Murata, M
    Iwashita, T
    Fujita, T
    [J]. TETRAHEDRON, 2005, 61 (36) : 8606 - 8610
  • [15] Effects of lipid constituents on membrane-permeabilizing activity of amphidinols
    Morsy, Nagy
    Houdai, Toshihiro
    Konoki, Kelichi
    Matsumori, Nobuaki
    Oishi, Tohru
    Murata, Michio
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (06) : 3084 - 3090
  • [16] Structures of new amphidinols with truncated polyhydroxyl chain and their membrane-permeabilizing activities
    Morsy, Nagy
    Houdai, Toshihiro
    Matsuoka, Shigeru
    Matsumori, Nobuaki
    Adachi, Seiji
    Oishi, Tohru
    Murata, Michio
    Iwashita, Takashi
    Fujita, Tsuyoshi
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (19) : 6548 - 6554
  • [17] Complex formation of amphotericin B in sterol-containing membranes as evidenced by surface plasmon resonance
    Mouri, Ryota
    Konoki, Keiichi
    Matsumori, Nobuaki
    Oishi, Tohru
    Murata, Michio
    [J]. BIOCHEMISTRY, 2008, 47 (30) : 7807 - 7815
  • [18] Analysis of antimicrobial peptide interactions with hybrid bilayer membrane systems using surface plasmon resonance
    Mozsolits, H
    Wirth, HJ
    Werkmeister, J
    Aguilar, MI
    [J]. BIOCHIMICA ET BIOPHYSICA ACTA-BIOMEMBRANES, 2001, 1512 (01): : 64 - 76
  • [19] Absolute configuration of amphidinol 3, the first complete structure determination from amphidinol homologues: Application of a new configuration analysis based on carbon-hydrogen spin-coupling constants
    Murata, M
    Matsuoka, S
    Matsumori, N
    Paul, GK
    Tachibana, K
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (04) : 870 - 871
  • [20] Combinatorial Synthesis of the 1,5-Polyol System Based on Cross Metathesis: Structure Revision of Amphidinol 3
    Oishi, Tohru
    Kanemoto, Mitsunori
    Swasono, Respati
    Matsumori, Nobuaki
    Murata, Michio
    [J]. ORGANIC LETTERS, 2008, 10 (22) : 5203 - 5206
123