Cholesteryl-cyclodextrins:: synthesis and insertion into phospholipid membranes

被引:52
作者
Auzély-Velty, R
Perly, B
Taché, O
Zemb, T
Jéhan, P
Guenot, P
Dalbiez, JP
Djedaïni-Pilard, F
机构
[1] CEA Saclay, DRECAM, Serv Chim Mol, F-91191 Gif Sur Yvette, France
[2] Univ Rennes 1, CRMPO, F-35042 Rennes, France
关键词
amphiphilic cyclodextrins; phospholipid bilayers; NMR spectroscopy; X-ray scattering;
D O I
10.1016/S0008-6215(99)00086-5
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
6(I)-(Cholest-5-en-3 beta-yloxycarbonyl)amino-6(1w)-deoxycyclomaltoheptaose and 6(I)-(cholest-5-en-3 alpha-ylamido)succinylamido-6(I)-deoxycyclomaltoheptaose were synthesized and fully characterized by NMR spectroscopy experiments and mass spectrometry analysis. Incorporation of these monosubstituted amphiphilic cyclodextrins into phospholipid bilayers was investigated using small-angle X-ray scattering, differential scanning calorimetry and P-31 nuclear magnetic resonance. Different modes of incorporation depending on the spacer length between the cyclodextrin and cholesterol moieties were observed. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:82 / 90
页数:9
相关论文
共 30 条
  • [1] CHANNEL-TYPE MOLECULAR-STRUCTURES .2. SYNTHESIS OF BOUQUET-SHAPED MOLECULES BASED ON A BETA-CYCLODEXTRIN CORE
    CANCEILL, J
    JULLIEN, L
    LACOMBE, L
    LEHN, JM
    [J]. HELVETICA CHIMICA ACTA, 1992, 75 (03) : 791 - 812
  • [2] Effect of carbohydrates on the swelling of a lyotropic lamellar phase
    Deme, B
    Dubois, M
    Zemb, T
    Cabane, B
    [J]. JOURNAL OF PHYSICAL CHEMISTRY, 1996, 100 (09) : 3828 - 3838
  • [3] SYNTHESIS OF A NEW MOLECULAR CARRIER - N-(LEU-ENKEPHALIN)YL 6-AMIDO-6-DEOXY-CYCLOMALTOHEPTAOSE
    DJEDAINIPILARD, F
    DESALOS, J
    PERLY, B
    [J]. TETRAHEDRON LETTERS, 1993, 34 (15) : 2457 - 2460
  • [4] POTENTIAL FORMATION OF INTRAMOLECULAR INCLUSION COMPLEXES IN PEPTIDO-CYCLODEXTRINS AS EVIDENCED BY NMR-SPECTROSCOPY
    DJEDAINIPILARD, F
    AZAROUALBELLANGER, N
    GOSNAT, M
    VERNET, D
    PERLY, B
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1995, (04): : 723 - 730
  • [5] Structural properties of several amphiphile cyclodextrins and some related nanospheres. An X-ray scattering and freeze-fracture electron microscopy study
    Gulik, A
    Delacroix, H
    Wouessidjewe, D
    Skiba, M
    [J]. LANGMUIR, 1998, 14 (05) : 1050 - 1057
  • [6] HYDE S, 1997, LANGUAGESHAPE
  • [7] JANIAK MJ, 1979, J BIOL CHEM, V254, P6068
  • [8] NATURE OF THERMAL PRE-TRANSITION OF SYNTHETIC PHOSPHOLIPIDS - DIMYRISTOYLLECITHIN AND DIPALMITOYLLECITHIN
    JANIAK, MJ
    SMALL, DM
    SHIPLEY, GG
    [J]. BIOCHEMISTRY, 1976, 15 (21) : 4575 - 4580
  • [9] INVESTIGATION OF EXCHANGE PROCESSES BY 2-DIMENSIONAL NMR-SPECTROSCOPY
    JEENER, J
    MEIER, BH
    BACHMANN, P
    ERNST, RR
    [J]. JOURNAL OF CHEMICAL PHYSICS, 1979, 71 (11) : 4546 - 4553
  • [10] AN APPROACH TO CHANNEL-TYPE MOLECULAR-STRUCTURES .3. INCORPORATION STUDIES OF THE BOUQUET-SHAPED B(M) AND B(CD) IN PHOSPHATIDYLCHOLINE VESICLES
    JULLIEN, L
    LAZRAK, T
    CANCEILL, J
    LACOMBE, L
    LEHN, JM
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (06): : 1011 - 1020