Ganglioside GM1 mimics: Lipophilic substituents improve affinity for cholera toxin

被引：17
|
作者：
Arosio, D [1 ]
Baretti, S [1 ]
Cattaldo, S [1 ]
Potenza, D [1 ]
Bernardi, A [1 ]
机构：
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
来源：
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2003年 / 13卷 / 21期
关键词：
D O I：
10.1016/j.bmcl.2003.07.007
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
Ganglioside GM1 mimics including (R)-2-hydroxy-3-cyclohexylpropionic acid or (R)-2-hydroxy-3-phenylpropionic acid as replacements for NeuAc are stronger cholera toxin binders than the parent ligand 2, which includes (R)-2-hydroxy-propionic acid. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：3831 / 3834
页数：4
相关论文
共 50 条
  • [1] Mimics of ganglioside GM1 as cholera toxin ligands:: replacement of the GalNAc residue
    Bernardi, A
    Arosio, D
    Manzoni, L
    Monti, D
    Posteri, H
    Potenza, D
    Mari, S
    Jiménez-Barbero, J
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2003, 1 (05) : 785 - 792
  • [2] FUC-GM1 GANGLIOSIDE MIMICS THE RECEPTOR FUNCTION OF GM1 FOR CHOLERA-TOXIN
    MASSERINI, M
    FREIRE, E
    PALESTINI, P
    CALAPPI, E
    TETTAMANTI, G
    BIOCHEMISTRY, 1992, 31 (08) : 2422 - 2426
  • [3] CHOLERA TOXIN - INTERACTION OF SUBUNITS WITH GANGLIOSIDE GM1
    VANHEYNINGEN, S
    SCIENCE, 1974, 183 (4125) : 656 - 657
  • [4] Development of novel GM1 ganglioside-like peptide mimics that prevent the association of cholera toxin B subunit to GM1
    Yu, Robert K.
    Usuki, Seigo
    Itokazu, Yutaka
    Wu, Han-Chung
    GLYCOBIOLOGY, 2015, 25 (11) : 1245 - 1245
  • [5] GM1 ganglioside-independent intoxication by Cholera toxin
    Cervin, Jakob
    Wands, Amberlyn M.
    Casselbrant, Anna
    Wu, Han
    Krishnamurthy, Soumya
    Cvjetkovic, Aleksander
    Estelius, Johanna
    Dedic, Benjamin
    Sethi, Anirudh
    Wallom, Kerri-Lee
    Riise, Rebecca
    Backstrom, Malin
    Wallenius, Ville
    Platt, Frances M.
    Lebens, Michael
    Teneberg, Susann
    Fandriks, Lars
    Kohler, Jennifer J.
    Yrlid, Ulf
    PLOS PATHOGENS, 2018, 14 (02)
  • [6] THERMOTROPIC BEHAVIOR OF CHOLERA-TOXIN AND CHOLERA TOXIN-GANGLIOSIDE GM1 MIXTURES
    GOINS, B
    FREIRE, E
    BIOPHYSICAL JOURNAL, 1987, 51 (02) : A165 - A165
  • [7] FLUORESCENT DERIVATIVES OF GANGLIOSIDE GM1 ARE FUNCTIONALLY EQUIVALENT TO GM1 AS RECEPTORS FOR CHOLERA-TOXIN
    SPIEGEL, S
    FISHMAN, PH
    FEDERATION PROCEEDINGS, 1985, 44 (04) : 1089 - 1089
  • [8] INTERACTION OF GM1 GANGLIOSIDE WITH CHOLERA TOXIN-B SUBUNIT
    DALZIEL, AW
    STURTEVANT, JM
    SCHAFER, DE
    FEDERATION PROCEEDINGS, 1982, 41 (04) : 1186 - 1186
  • [9] BINDING OF INTRALUMINAL TOXIN IN CHOLERA - TRIAL OF GM1 GANGLIOSIDE CHARCOAL
    STOLL, BJ
    BARDHAN, PK
    GREENOUGH, WB
    SVENNERHOLM, L
    HOLMGREN, J
    HUQ, I
    FREDMAN, P
    LANCET, 1980, 2 (8200): : 888 - 891
  • [10] Cholera toxin assault on lipid monolayers containing ganglioside GM1
    Miller, CE
    Majewski, J
    Faller, R
    Satija, S
    Kuhl, TL
    BIOPHYSICAL JOURNAL, 2004, 86 (06) : 3700 - 3708
12345