Physico-chemical investigation of asymmetrical peptidolipidyl-cyclodextrins

被引：43

作者：

Angelova, Angelina ^{[2
]}

Fajolles, Christophe ^{[1
]}

Hocquelet, Celine ^{[1
]}

Djedaini-Pilard, Florence ^{[3
]}

Lesieur, Sylviane ^{[2
]}

Bonnet, Veronique ^{[3
]}

Perly, Bruno ^{[1
]}

Lebas, Genevieve ^{[2
]}

Mauclaire, Laurent ^{[1
]}

机构：

[1] CEA Saclay, CEA, DSM, DRECAM,SCM, F-91191 Gif Sur Yvette, France

[2] Univ Paris Sud, Equipe Physicochim Syst Polyphases, CNRS, UMR8612 Physicochim, F-92290 Chatenay Malabry, France

[3] Univ Picardie Jules Verne, Lab Glucides, CNRS, UMR 6219, F-80039 Amiens, France

来源：

JOURNAL OF COLLOID AND INTERFACE SCIENCE | 2008年 / 322卷 / 01期

关键词：

amphiphile; beta-cyclodextrin; micelle; aggregate; lyotropic behavior;

D O I：

10.1016/j.jcis.2008.03.023

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

A new class of amphiphilic peptidolipidyl-cyclodextrins is reported. The derivatives are chiral due to the presence of an L-leucine in the spacer arm that links a saccharide moiety and a grafted, saturated hydrocarbon chain. Self-assembly properties of the peptidolipidyl-cyclodextrins are characterized by quasi-elastic light scattering, turbidity and UV-visible absorption measurements. NMR experiments give insight into the intermolecular dipolar interactions as a function of temperature and concentration. N-dodecyl-N-alpha-(6(I)-amidosuccinyl-6(I)-deoxy-cyclomaltoheptaose)-L-leucine (1) is poorly soluble in aqueous media. N-dodecyl-N-alpha-(6(I)-amidosuccinyl-6(I)-deoxy-2(I),3(I)-di-O-methyl-hexakis-(2(II-VII),3(II-VII),6(II-VII)-tri-O-methyl)-cyclomaltoheptaose)-L-leucine(2) is found to be more soluble and self-assembles into stable supramolecular colloidal aggregates with nanometric dimensions above a critical aggregation concentration (CAC). It has a propensity for solubilization of hydrophobic species revealing a micellar-like behavior, which is compared to that of the non-ionic detergent octyl glucoside. On the contrary, compound I precipitates in a crystalline phase beyond its water solubility limit, and it does not display any solubilizing capacity. The observed behavior corroborates at the molecular level with the NMR results. (c) 2008 Elsevier Inc. All rights reserved.

引用

页码：304 / 314

页数：11

共 41 条

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