Interfacial behavior of chroman-6 and chroman-6 palmitoyl ester and their interaction with phospholipids

• Published in: Colloid and polymer science Vol. 291; no. 5; pp. 1065 - 1075
• Main Authors: García-Antón, J. M., Reig, F., Messeguer, A., Comelles, F., Espina, M., Alsina, M. A.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer-Verlag 01.05.2013; Springer; Springer Nature B.V
• Subjects: Biological and medical sciences; Chains; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Chromium; Complex Fluids and Microfluidics; Compressibility; Constants; Esters; Food Science; General and cellular metabolism. Vitamins; Lipids; Medical sciences; Nanotechnology and Microengineering; Original Contribution; Pharmacology. Drug treatments; Physical Chemistry; Polymer Sciences; Rendering; Soft and Granular Matter; Surface chemistry; Differential scanning calorimetry; Surface pressure; Phospholipids; Mixed films; Monolayers; Compression isotherms; Vitamin; Liposome; Phospholipid; Molecular interaction; Hydrophobicity; Antioxidant; Chroman derivatives; Vitamin E; Plasma membrane; Property structure relationship
• ISSN: 0303-402X; 1435-1536
• DOI: 10.1007/s00396-012-2829-1

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.