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.
References
Casas J, Gorchs G, Sánchez-Baeza F, Teixidor P, Messeguer A (1992) Inhibition of rat liver microsomal lipid peroxidation elicited by simple 2,2-dimethylchromenes and chromans structurally related to precocenes. J Agric Food Chem 40:585–590
Sanvicens N, Gomez-Vicente V, Messeguer A, Cotter TG (2006) The radical scavenger CR-6 protects SH-SY5Y neuroblastoma cells from oxidative stress-induced apoptosis: effect on survival pathways. J Neurochem 98:735–747
Cebrian J, Messeguer A, Facino RM, Garcia Anton JM (2005) New anti-RNS and -RCS products for cosmetic treatment. Int J Cosmet Sci 27:271–278
Lopez-Pousa A, Bui Nguyen B, Garcia del Muro X, et al. (2011) A phase II study of a new formulation of nonpegylated liposomal doxorubicin (doxorubicin GP-pharm) as first-line treatment in patients with advanced soft-tissue sarcomas (STS) who are age 65 or older: a GEIS trial. J Clin Oncol 29. suppl; abstr 10072
Panda AK, Wojciechowski P, Nag K, Possmayer F, Petersen NO (2009) Thermodynamic and fluorescence studies on the interaction of cholesterol with palmitoyl-oleoyl phosphatidylcholine and sphingomyelin. J Dispers Sci Technol 30:1255–1261
Levental I, Christian DA, Wang YH, Madara JJ, Discher DE, Janmey PA (2009) Calcium-dependent lateral organization in phosphatidylinositol 4,5-bisphosphate (PIP2)- and cholesterol-containing monolayers. Biochemistry 48:8241–8248
Fernandez-Botello A, Comelles F, Alsina MA, Cea P, Reig F (2008) A monolayer study on interactions of docetaxel with model lipid membranes. J Phys Chem B 112:13834–13841
Zhao L, Feng SS (2005) Effects of lipid chain unsaturation and headgroup type on molecular interactions between paclitaxel and phospholipid within model biomembrane. J Colloid Interface Sci 285:326–335
Broniec A, Gjerde AU, Olmheim AB, Holmsen H (2007) Trifluoperazine causes a disturbance in glycerophospholipid monolayers containing phosphatidylserine (PS): effects of pH, acyl unsaturation, and proportion of PS. Langmuir 23:694–699
Chen Y, Sun R, Wang B (2011) Monolayer behavior of binary systems of betulinic acid and cardiolipin: thermodynamic analyses of Langmuir monolayers and AFM study of Langmuir–Blodgett monolayers. J Colloid Interface Sci 353:294–300
Lucio M, Bringezu F, Reis S, Lima JL, Brezesinski G (2008) Binding of nonsteroidal anti-inflammatory drugs to DPPC: structure and thermodynamic aspects. Langmuir 24:4132–4139
Jabłonowska E, Bilewicz R (2007) Interactions of ibuprofen with Langmuir monolayers of membrane lipids. Thin Solid Films 515:3962–3966
Alsina MA, Ortiz A, Polo D, Comelles F, Reig F (2006) Synthesis and study of molecular interactions between phosphatidyl choline and two laminin derived peptides hydrophobically modified. J Colloid Interface Sci 294:385–390
Larios C, Minones J Jr, Haro I, Alsina MA, Busquets MA, Trillo JM (2006) Study of adsorption and penetration of E2(279–298) peptide into Langmuir phospholipid monolayers. J Phys Chem B 110:23292–23299
Almiñana N, Alsina MA, Ortiz A, Reig F (2004) Comparative physicochemical study of SIKVAV peptide and its retro and retro-enantio analogues. Colloids Surf A Physicochem Eng Asp 249:19–24
Ishitsuka Y, Pham DS, Waring AJ, Lehrer RI, Lee KY (2006) Insertion selectivity of antimicrobial peptide protegrin-1 into lipid monolayers: effect of head group electrostatics and tail group packing. Biochim Biophys Acta 1758:1450–1460
Mussone PG, Ip AW, Schroeder SL, Murray BS, Miller AF (2007) Irreversible collapse of poly(vinyl stearate) monolayers at the air–water interface. Langmuir 23:3766–3773
Corvis Y, Barzyk W, Brezesinski G, Mrabet N, Badis M, Hecht S, Rogalska E (2006) Interactions of a fungistatic antibiotic, griseofulvin, with phospholipid monolayers used as models of biological membranes. Langmuir 22:7701–7711
Castelli F, Sarpietro MG, Rocco F, Ceruti M, Cattel L (2007) Interaction of lipophilic gemcitabine prodrugs with biomembrane models studied by Langmuir–Blodgett technique. J Colloid Interface Sci 313:363–368
Micieli D, Giuffrida MC, Pignatello R, Castelli F, Sarpietro MG (2011) Interaction of naproxen amphiphilic derivatives with biomembrane models evaluated by differential scanning calorimetry and Langmuir–Blodgett studies. J Colloid Interface Sci 360:359–369
Hac-Wydro K, Zajac A, Dynarowicz-Latka P (2011) The influence of plant stanol on phospholipids monolayers—the effect of phospholipid structure. J Colloid Interface Sci 360:681–689
Ambike A, Rosilio V, Stella B, Lepetre-Mouelhi S, Couvreur P (2011) Interaction of self-assembled squalenoyl gemcitabine nanoparticles with phospholipid–cholesterol monolayers mimicking a biomembrane. Langmuir 27:4891–4899
Fresta M, Ventura CA, Mezzasalma E, Puglisi G (1998) A calorimetric study on the idebenone–phospholipid membrane interaction. Int J Pharm 163:133–143
Acknowledgments
We are very grateful to Jessica Priego (Lipotec S.A.) for her technical help. The research was carried out with the financial support of projects SAF2008-00048 and SAF2011-30542-CO2-01 from Programa Nacional de Biomedicina, Ministerio de Ciencia e Innovación (Spain).
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García-Antón, J.M., Reig, F., Messeguer, A. et al. Interfacial behavior of chroman-6 and chroman-6 palmitoyl ester and their interaction with phospholipids. Colloid Polym Sci 291, 1065–1075 (2013). https://doi.org/10.1007/s00396-012-2829-1
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DOI: https://doi.org/10.1007/s00396-012-2829-1