Critical role of the degree of substitution in the interaction of biocompatible cholic acid-modified dextrans with phosphatidylcholine liposomes

Langmuir

Volumn 29, Issue 43, 2013, Pages 13258-13268

  Bai, Guangyue ^a,b   Wang, Yujie ^c   Nichifor, Marieta ^d   Bastos, Margarida ^b  

^a HENAN NORMAL UNIVERSITY   (China)

^b UNIVERSITY OF PORTO   (Portugal)

^c HENAN INSTITUTE OF SCIENCE AND TECHNOLOGY   (China)

^d PETRU PONI INSTITUTE OF MACROMOLECULAR CHEMISTRY   (Romania)

Author keywords

[No Author keywords available]

Indexed keywords

CRYO-SCANNING ELECTRON MICROSCOPY; DEGREE OF SUBSTITUTION; INDIVIDUAL COMPONENTS; INTERACTION ENTHALPIES; ISOTHERMAL TITRATION CALORIMETRY; LIQUID-CRYSTALLINE PHASE; POLYMER CONCENTRATIONS; TURBIDITY MEASUREMENTS;

AGGREGATES; BIOCOMPATIBILITY; DEXTRAN; DIFFERENTIAL SCANNING CALORIMETRY; LIPOSOMES; MORPHOLOGY; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY; TURBIDITY;

POLYMERS;

BIOMATERIAL; CHOLIC ACID; DEXTRAN; LIPOSOME; PHOSPHATIDYLCHOLINE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; PARTICLE SIZE; SURFACE PROPERTY;

BIOCOMPATIBLE MATERIALS; CHOLIC ACID; DEXTRANS; LIPOSOMES; MOLECULAR STRUCTURE; PARTICLE SIZE; PHOSPHATIDYLCHOLINES; SURFACE PROPERTIES;

EID: 84887028923     PISSN: 07437463     EISSN: 15205827     Source Type: Journal    
DOI: 10.1021/la402754y     Document Type: Article

References (49)

1. Barenholz, Y. Liposome application: problems and prospects Curr. Opin. Colloid Interface Sci. 2001, 6, 66-77
2. Yaroslavov, A. A.; Melik-Nubarov, N. S.; Menger, F. M. Polymer-induced flip-flop in biomembranes Acc. Chem. Res. 2006, 39, 702-710
3. Luan, Y.; Ramos, L. Real-time observation of polyelectrolyte-induced binding of charged bilayers J. Am. Chem. Soc. 2007, 129, 14619-14624
4. Quemeneur, F.; Rinaudo, M.; Pepin-Donat, B. Influence of polyelectrolyte chemical structure on their interaction with lipid membrane of zwitterionic liposomes Biomacromolecules 2008, 9, 2237-2243
5. Tribet, C.; Vial, F. Flexible macromolecules attached to lipid bilayers: impact on fluidity, curvature, permeability and stability of the membranes Soft Matter 2008, 4, 68-81
6. Antunes, F. E.; Marques, E. F.; Miguel, M. G.; Lindman, B. Polymer-vesicle association Adv. Colloid Interface Sci. 2009, 147-148, 18-35
7. Hirsjärvia, S.; Dufortb, S.; Bastiata, G.; Saulniera, P.; Passirania, C.; Collb, J.-L.; Benoiît, J.-P. Surface modification of lipid nanocapsules with polysaccharides: from physicochemical characteristics to in vivo aspects Acta Biomater. 2013, 9, 6686-6693
8. Lee, J.-H.; Oh, H.; Baxa, U.; Raghavan, S. R.; Blumenthal, R. Biopolymer-connected liposome networks as injectable biomaterials capable of sustained local drug delivery Biomacromolecules 2012, 13, 3388-3394
9. Devadasu, V. R.; Bhardwaj, V.; Kumar, M.N.V. R. Can controversial nanotechnology promise drug delivery? Chem. Rev. 2013, 113, 1686-1735
10. Silva, R.; Ferreira, H.; Cavaco-Paulo, A. Sonoproduction of liposomes and protein particles as templates for delivery purposes Biomacromolecules 2011, 12, 3353-3368
11. Dong, C.; Rogers, J. A. Polymer-coated liposomes: stability and release of ASA from carboxymethyl chitin-coated liposomes J. Controlled Release 1991, 17, 217-224
12. Zhang, L.; Peng, T.; Cheng, S.; Zhuo, R. Destabilization of liposomes by uncharged hydrophilic and amphiphilic polymers J. Phys. Chem. B 2004, 108, 7763-7770
13. Ringsdorf, H.; Venzmer, J.; Winnik, F. M. Interaction of hydrophobically-modified poly-N-isopropylacrylamides with model membranes-or playing a molecular accordion Angew. Chem., Int. Ed. Engl. 1991, 30, 315
14. Polozova, A.; Winnik, F. M. Mechanism of the interaction of hydrophobically-modified poly-(N-isopropylacrylamides) with liposomes Biochim. Biophys. Acta 1997, 1326, 213-224
15. Polozova, A.; Winnik, F. M. Contribution of hydrogen bonding to the association of liposomes and an anionic hydrophobically modified poly(N-isopropylacrylamide) Langmuir 1999, 15, 4222-4229
16. Shi, X.; Li, J.; Sun, C.; Wu, S. The aggregation and phase separation behavior of a hydrophobically modified poly(N -isopropylacrylamide) Colloids Surf., A 2000, 175, 41-49
17. Wang, Y. J.; Winnik, F. M.; Clarke, R. J. Interaction between DMPC liposomes and HM-PNIPAM polymer Biophys. Chem. 2003, 104, 449-458
18. Polozova, A.; Yamazaki, A.; Brash, J. L.; Winnik, F. M. Effect of polymer architecture on the interactions of hydrophobically-modified poly-(N -isopropylamides) and liposomes Colloids Surf., A 1999, 147, 17-25
19. Sunamoto, J.; Sato, T.; Taguchi, T.; Hamazaki, H. Naturally occurring polysaccharide derivatives which behave as an artificial cell wall on an artificial cell liposome Macromolecules 1992, 25, 5665-5670
20. Tan, H. W.; Misran, M. Polysaccharide-anchored fatty acid liposome Int. J. Pharm. 2013, 441, 414-423
21. Chieng, Y. Y.; Chen, S. B. Rheological study of hydrophobically modified hydroxyethyl cellulose and phospholipid vesicles J. Colloid Interface Sci. 2010, 349, 236-245
22. Auguste, D. T.; Prud'homme, R. K.; Ahl, P. L.; Meers, P.; Kohn, J. Association of hydrophobically-modified poly (ethylene glycol) with fusogenic liposomes Biochim. Biophys. Acta 2003, 1616, 184-195
23. Auguste, D. T.; Kirkwood, J.; Kohn, J.; Fuller, G. G.; Prud'homme, R. K. Surface rheology of hydrophobically modified PEG polymers associating with a phospholipid monolayer at the air-water interface Langmuir 2008, 24, 4056-4064
24. Park, S. I.; Lee, E. O.; Kim, J. W.; Kim, Y. J.; Han, S. H.; Kim, J. D. Polymer-hybridized liposomes anchored with alkyl grafted poly(asparagine) J. Colloid Interface Sci. 2011, 364, 31-38
25. Kepczynski, M.; Jamróz, D.; Wytrwal, M.; Bednar, J.; Rzad, E.; Nowakowska, M. Interactions of a hydrophobically modified polycation with zwitterionic lipid membranes Langmuir 2012, 28, 676-688
26. Nichifor, M.; Carpov, A. Bile acids covalently bound to polysaccharides. 1. Esters of bile acids with dextran Eur. Polym. J. 1999, 35, 2125-2129
27. Mehvar, R. Dextran for targeted and sustained delivery of therapeutic and imaging agents J. Controlled Release 2000, 69, 1-25
28. Madenci, D.; Egelhaaf, S. U. Self-assembly in aqueous bile salt solutions Curr. Opin. Colloid Interface Sci. 2010, 15, 109-115
29. Nair, P. P. In The Bile Acids: Chemistry, Physiology and Metabolism; Nair, P. P.; Kritchevsky, D. Eds.; Plenum Press: New York, 1971; Vol. 1.
30. Ross, B. P.; Braddy, A. C.; McGeary, R. P.; Blanchfield, J. T.; Prokai, L.; Toth, I. Micellar aggregation and membrane partitioning of bile salts, fatty acids, sodium dodecyl sulfate, and sugar-conjugated fatty acids: correlation with hemolytic potency and implications for drug delivery Mol. Pharm. 2004, 1, 233-245
31. 1 J. Biochem. 1992, 112, 671-676
32. Long, M. A.; Kaler, E. W.; Lee, S. P. Structural characterization of the micelle-vesicle transition in lecithin-bile salt solutions Biophys. J. 1994, 67, 1733-1742
33. Hildebrand, A.; Neubert, R.; Garidel, P.; Blume, A. Bile salt induced solubilization of synthetic phosphatidylcholine vesicles studied by isothermal titration calorimetry Langmuir 2002, 18, 2836-2847
34. Hildebrand, A.; Beyer, K.; Neubert, R.; Garidel, P.; Blume, A. Solubilization of negatively charged DPPC/DPPG liposomes by bile salts J. Colloid Interface Sci. 2004, 279, 559-571
35. Andrieux, K.; Forte, L.; Lesieur, S.; Paternostre, M.; Ollivon, M.; Grabielle-Madelmont, C. Solubilisation of dipalmitoylphosphatidylcholine bilayers by sodium taurocholate: a model to study the stability of liposomes in the gastrointestinal tract and their mechanism of interaction with a model bile salt Eur. J. Pharm. Biopharm. 2009, 71, 346-355
36. Mohapatra, M.; Mishra, A. K. Effect of submicellar concentrations of conjugated and unconjugated bile salts on the lipid bilayer membrane Langmuir 2011, 27, 13461-13467
37. Nichifor, M.; Lopes, A.; Carpov, A.; Melo, E. Aggregation in water of dextran hydrophobically modified with bile acids Macromolecules 1999, 32, 7078-7085
38. Bai, G.; Nichifor, M.; Bastos, M. Association and phase behavior of cholic acid-modified dextran and phosphatidylcholine liposomes J. Phys. Chem. Lett. 2010, 1, 932-936
39. Bastos, M.; Bai, G.; Gomes, P.; Goormaghtigh, E.; Prieto, M. Energetics and partition of two cecropin-melittin hybrid peptides to model membranes of different composition Biophys. J. 2008, 94, 2128-2141
40. McClare, C. W. F. An accurate and convenient organic phosphorous assay Anal. Biochem. 1971, 39, 527-530
41. Bai, G.; Santos, L. M. B. F.; Nichifor, M.; Lopes, A.; Bastos, M. Thermodynamics of interaction between hydrophobically modified polyelectrolyte and sodium dodecyl sulfate in aqueous solution J. Phys. Chem. B 2004, 108, 405-413
42. Bastos, M.; Hägg, S.; Lönnbro, P.; Wadsö, I. Fast titration experiments using heat conduction microcalorimeters J. Biochem. Biophys. Methods 1991, 23, 255-258
43. Lukac, S.; Perovic, A. Effect of stains and staining procedures on transmission electron microscopic images of surfactant vesicles J. Colloid Interface Sci. 1985, 103, 586-589
44. Piculell, L.; Guillemet, F.; Thuresson, K.; Shubin, V.; Ericsson, O. Binding of surfactants to hydrophobically modified polymers Adv. Colloid Interface Sci. 1996, 63, 1-21
45. Bai, G.; Catita, J. A. M.; Nichifor, M.; Bastos, M. Microcalorimetric evidence of hydrophobic interactions between hydrophobically modified cationic polysaccharides and surfactants of the Same J. Phys. Chem. B 2007, 111, 11453-11462
46. Mabrey, S.; Mateo, P. L.; Sturtevant, J. M. High-sensitivity scanning calorimetric study of mixtures of cholesterol with dimyristoyl- and dipalmitoylphosphatidylcholines Biochemistry 1978, 17, 2464-2468
47. Abrunhosa, F.; Faria, S.; Gomes, P.; Tomaz, I.; Pessoa, J. C.; Andreu, D.; Bastos, M. Interaction and lipid-induced conformation of two cecropin-melittin hybrid peptides depend on peptide and membrane composition J. Phys. Chem. B 2005, 109, 17311-17319
48. Silva, T.; Adão, R.; Nazmi, K.; Bolscher, J. G. M.; Funari, S.; Uhríková, D.; Bastos, M. Structural diversity and mode of action on lipids membranes of three lactoferrin candidacidal peptides Biochim. Biophys. Acta 2013, 1828, 1329-1339
49. Bai, G.; Wang, Y.; Wang, J.; Han, B.; Yan, H. Microcalorimetric studies of the interaction between DDAB and SDS and the phase behavior of the mixture Langmuir 2001, 17, 3522-3525