New Lamellar Structure Formed by an Adamantyl Derivative of Cholic Acid

• Published in: The journal of physical chemistry. B Vol. 110; no. 28; pp. 13679 - 13681
• Main Authors: Soto Tellini, Victor Hugo, Jover, Aida, Galantini, Luciano, Pavel, Nicolae Viorel, Meijide, Francisco, Vázquez Tato, José
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 20.07.2006
• Subjects: Adamantane - analogs & derivatives; Adamantane - chemical synthesis; Adamantane - chemistry; Cholic Acid - chemistry; Crystallography, X-Ray; Microscopy, Electron, Transmission - methods; Models, Molecular; Particle Size; Scattering, Small Angle; Sensitivity and Specificity; X-Ray Diffraction
• ISSN: 1520-6106; 1520-5207
• DOI: 10.1021/jp062835n

The self-aggregation of the sodium salt of a new adamantyl amide of the 3β-amino derivative of cholic acid (Na-AdC) in aqueous solution has been investigated by surface tension, dynamic light scattering, fluorescence, small-angle X-ray scattering (SAXS), and transmission electron microscopy (TEM) measurements. These last two techniques suggest that a lamellar phase, consisting of charged bilayers of Na-AdC separated by solvent and periodically stacked, is formed in aqueous solution. The structure of the bilayer is inferred from the resolution of the crystal of the compound in its acid form. The adamantyl moieties, which are mutually interlocked, reside in the central region of the bilayer, and the carboxylic groups are directed toward the hydrophilic region. The structure is open enough to allow water molecules to interact with a fluorescence probe located at the central hydrophobic region.