Interfacial behavior of chroman-6 and chroman-6 palmitoyl ester and their interaction with phospholipids |
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Authors: | J M García-Antón F Reig A Messeguer F Comelles M Espina M A Alsina |
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Institution: | 1. Lipotec S.A., Isaac Peral 17, Polígon Industrial, Camí Ral, 08850, Gavà, Barcelona, Spain 2. Chemical and Biomolecular Nanotechnology Department, Catalonian Institute for Advanced Chemistry, CSIC, Jordi Girona 18, 08034, Barcelona, Spain 3. Chemical and Surfactant Technology Department, Catalonian Institute for Advanced Chemistry, CSIC, Jordi Girona 18, 08034, Barcelona, Spain 4. Physicochemical Department, Faculty of Pharmacy, University of Barcelona, Av. Joan XXIII s/n, 08028, Barcelona, Spain
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Abstract: | The surface activity of chroman-6 (CR-6) and chroman-6 palmitoyl ester (PCR-6) and the interactions with lipid membranes, using 1,2-dipamitoyl-sn-glycero-3-phosphocholine (DPPC) and 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC) monolayers, were determined. 8-Anilino-1-naphthalenesulfonic acid titration indicates that none of these molecules was able to form aggregates in aqueous media. The presence of a palmitoyl chain in PCR-6 increases strongly the surface activity of the parent compound (CR-6), rendering a molecule to form stable monomolecular layers. The interaction of both compounds with DPPC and DOPC, measured at constant area or in a compression isotherm model, follows the same trend. Miscibility studies performed with DPPC/CR-6 or PCR-6 indicate that the energies involved are small. The presence of CR-6 and PCR-6 has a soft influence on the compressibility of the Langmuir mixed films. Differential scanning calorimetry studies indicate that CR-6 and PCR-6 modify the temperature and cooperativity of the transition from gel to liquid crystal process in DPPC vesicles. |
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