Fine-tuning of POPC liposomal leakage by the use of β-cyclodextrin and several hydrophobic guests

Journal of Liposome Research

Volumn 20, Issue 3, 2010, Pages 202-210

  Gasbarri, Carla ^a   Guernelli, Susanna ^b   Boncompagni, Simona ^a   Angelini, Guido ^a   Siani, Gabriella ^a   Maria, Paolo De ^a   Fontana, Antonella ^a  

^a UNIVERSITY OF CHIETI   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

cyclodextrin; 1,2 dipalmitoyl sn glycero 3 phospho ethanolamine N methoxy (polyethylene glycol) 2000 ammonium salt; ESI MS; Fullerene C60; Lamellarity; Liposomal leakage

Indexed keywords

1 PALMITOYL 2 OLEOYL SN GLYCERO 3 PHOSPHOCHOLINE; 6 CARBOXYFLUORESCEIN; BETA CYCLODEXTRIN; LIPOSOME; PHOSPHORYLCHOLINE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; DEHYDRATION; DRUG RELEASE; ELECTROSPRAY MASS SPECTROMETRY; ENCAPSULATION; EXTRACTION; FLUOROMETRY; MASS SPECTROMETRY; PRIORITY JOURNAL; REHYDRATION; TURBIDIMETRY;

BETA-CYCLODEXTRINS; DRUG STABILITY; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; KINETICS; LIPOSOMES; MICROSCOPY, ELECTRON, TRANSMISSION; PHOSPHATIDYLCHOLINES; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 77955076623     PISSN: 08982104     EISSN: 15322394     Source Type: Journal    
DOI: 10.3109/08982100903244526     Document Type: Article

References (65)

1. a values of carboxyfuorescein. J Org Chem 73:3411-3417.
2. Bakker, J., Sanders, A., Van Rooijen, N. (1998). Effects of liposome-encapsulated drugs on macrophages: comparative activity of the diamidine 4',6-diamidino-2-phenylindole and the phen-anthridinium salts, ethidium bromide and propidium iodide. Biochim Biophys Acta 1373:93-100.
3. Bangham, A. D., Horn, R. W. (1964). Negative staining of phos-pholipids and their structural modifcation by surface-active agents as observed in the electron microscope. J Mol Biol 8:660-668.
4. Bender, M. L., Komiyama, M. (1978). Cyclodextrin chemistry. Berlin, Germany: Springer-Verlag.
5. 60 in model biological systems. A visible-UV absorption study of solvent-dependent parameters and solute aggregation. J Phys Chem 98:3492-3500.
6. Bucak, S., Robinson, B. H., Fontana, A. (2002). Kinetics of induced vesicle breakdown for cationic and catanionic systems. Langmuir 18:8288-8294.
7. Ch, B., Winterhalter, M., Frederik, P. M., Vallner, J. J., Lasic, D. D. (1997). Stealth liposomes: from theory to product. Adv Drug Deliv Rev 24:165-177.
8. Chong, C. S., Colbow, K. (1976). Light scattering and turbidity measurements on lipid vesicles. Biochim Biophys Acta 436: 260-282.
9. De Maria, P., Filippone, P., Fontana, A., Gasbarri, C., Siani, G., Velluto, D. (2005). Cardanol as a replacement for cholesterol into the lipid bilayer of POPC liposomes. Coll Surf B Biointerf 40:11-18.
10. De Maria, P., Fontana, A., Gasbarri, C., Velluto, D. (2006). Effects of fullerene guests on the stability of 1-palmitoyl-2-oleoylphosphatidylcholine liposomes. Soft Matter 2:595-602.
11. 70, in water. Preparation and characterization. Langmuir 17:6013-6017.
12. De Jesus Barbosa, H., Beltran, O. C., Escobar, M. J., Jimenez, F., Martinez, F. (1998). Characterization of liposome vesicles. 1. Effect of phospholipid composition on entrapped volume. Revista Colombiana de Ciencias Quimico-Farmaceuticas 27:31-34.
13. Debouzy, J. C., Fauvelle, F., Crouzy, S., Girault, L., Chapron, Y., Göschl, M., et al. (1998). Mechanism of α-cyclodextrin-induced hemolysis. 2. A study of the factors controlling the association with serine-, ethanolamine-, and choline-phospholipids. J Pharm Sci 87:59-66.
14. Deo, N., Somasundaran, T., Somasundaran, P. (2004). Solution properties of amitriptyline and its partitioning into lipid bilayers. Coll Surf B Biointerf 34:155-159.
15. Egerdie, B., Singer, M. (1982). Morphology of gel-state phosphati-dylethanolamine and phosphatidylcholine liposomes: a negative stain electron microscopic study. Chem Phys Lipids 31:75-85.
16. Fauvelle, F., Debouzy, J. C., Crouzy, S., Goschl, M., Chapron, Y. (1997). Mechanism of α-cyclodextrin-induced hemolysis. 1. The two-step extraction of phosphatidylinositol from the membrane. J Pharm Sci 86:935-943.
17. Frank, D. W., Gray, J. E., Weaver, R. N. (1976). Cyclodextrin nephrosis in the rat. Am J Pathol 83:367-382.
18. Frijlink, H. W., Eissens, A. C., Hefting, N. R., Poelstra, K., Lerk, C. F., Meijer, D. K. F. (1991). The efect of parenterally administered cyclodextrins on cholesterol levels in the rat. Pharm Res 8:9-16.
19. Gilbert, B. E., Wyde, P. R., Wilson, S. Z., Robins, R. K. (1991). Aerosol and intraperitoneal administration of ribavirin and ribavirin triacetate: pharmacokinetics and protection of mice against intracerebral infection with infuenza A/WSN virus. Antimicrob Agents Chemother 35:1448-1453.
20. Gonzalez-Gaitan, G., Rodríguez, P., Isasi, J. R., Fuentes, M., Tardajos, G., Sánchez, M. (2003). The aggregation of cyclo-dextrins as studied by photon correlation spectroscopy. J Incl Phenom Macrocycl Chem 44:101-105.
21. Gregoriadis, G. (1988). Liposomes as drug carriers: recent trends and progress. Chichester, UK: John Wiley & Sons.
22. Han, X., Gross, R. W. (1995). Structural determination of picomole amounts of phospholipids via electrospray ionization tandem mass spectrometry. J Am Mass Spectrom 6:1202-1210.
23. Harris, J. M. (1993). Polyethylene glycol chemistry. New York: Plenum.
24. Holland, J. W., Hui, C., Cullis, P. R., Madden, T. D. (1996). Poly(ethylene glycol)-lipid conjugates regulate the calcium-induced fusion of liposomes composed of phosphatidylethanolamine and phos-phatidylserine. Biochemistry 35:2618-2624.
25. 60 into artifcial lipid membranes. J Am Chem Soc 115:3386-3387.
26. Irie, T., Fukunaga, K., Pitha, J. (1992). Hydroxypropyl cyclodextrins in parenteral use. I: Lipid dissolution and efects on lipid transfers in vitro. J Pharma Sci 81: 521-523
27. Kashchiev, D., Exerova, D. (1983). Bilayer lipid membrane permeation and rupture due to hole formation. Biochim Biophys Acta 732:133-145.
28. Kawakami, K., Nishihara, Y., Hirano, K. (1999). Determination of the entrapped volume of liposomes: dilution method. Anal Biochem 269:139-142.
29. Kinoshita, K., Yamazaki, M. (1997). Phase transition between hexagonal II (H[II]) and liquid-crystalline phase induced by interaction between solvents and segments of the membrane surface of dioleoylphosphatidylethanolamine. Biochim Biophys Acta 1330:199-206.
30. Kinoshita, K., Asano, T., Yamazaki, M. (1997). Interaction of the surface of biomembrane with solvents: structure of multilamellar vesicles of dipalmitoylphosphatidylcholine in acetone-water mixtures. Chem Phys Lipids 85:53-65.
31. Kinoshita, K., Furuike, S., Yamazaki, M. (1998). Intermembrane distance in multilamellar vesicles of phosphatidylcholine depends on the interaction free energy between solvents and the hydrophilic segments of the membrane surface. Biophys Chem 74:237-249.
32. Kirby, C., Gregoriadis, G. (1983). The efect of lipid composition of small unilamellar liposomes containing melphalan and vincris-tine on drug clearance after injection into mice. Biochem Pharm 32:609-615. (Pubitemid 13148274)
33. Kirby, C., Gregoriadis, G. (1984). Dehydration-rehydration vesicles: a simple method for high-yield drug entrapment in liposomes. Bio/Thechnology 2:979-984.
34. Krätschmer, W., Lamb, L. D., Fostiropoulos, K., Hufman, D. R. (1990). Solid C60: a new form of carbon. Nature 347:354-358.
35. Lasch, J. (1995). Interaction of detergent with lipid vesicles. Biochim Biophys Acta 1241:269-292.
36. Lasic, D. D. (1994). Sterically stabilized vesicles. Angew Chem Int Ed Engl 33:1685-1690.
37. Legendre, J. Y., Rault, I., Petit, A., Luijten, W., Demuynck, I., Horvath, S., et al. (1995). Effects of β-cyclodextrins on skin: implications for the transdermal delivery of piribedil and a novel cognition enhancing-drug, S-9977. Eur J Pharm Sci 3:311-322.
38. Lichtenberg, D., Zilberman, Y., Greenzaid, P., Zamir, S. (1979). Structural and kinetic studies on the solubilization of lecithin by sodium deoxycholate. Biochemistry 18:3517-3525.
39. McCormack. B., Gregoriadis, G. (1996). Comparative studies of the fate of free and liposome-entrapped hydroxypropil-β-cyclodextrin/drug complexes after intravenous injection into rats: implications in drug delivery. Biochim Biophys Acta 1291:237-244.
40. Mobley, W. C. (1998). The efect of jet-milling on lyophilized lipo-somes. Pharm Res 15:149-152.
41. Mori, A., Klibanov, A., Torchilin, V. P., Huang, L. (1991). Infuence of steric barrier activity of amphipathic polyethylene glycol and ganglioside GM1 on the circulation time of liposomes and on target binding of immunoliposomes in vivo. FEBS Lett 284:263-266.
42. Murthy, C. N., Geckeler, K. E. (2001). The water-soluble β-cyclodextrin-[60]fullerene complex. Chem Comm 1194-1195.
43. Needham, D., Nunn, R. S. (1990). Elastic deformation and failure of lipid bilayer membranes containing cholesterol. Biophys J 58:997-1009.
44. Needham, D., Stoicheva, N., Zhelev, D. V. (1997). Exchange of monooleoylphosphatidylcholine as monomer and micelle with membranes containing poly(ethylene glycol)-lipid. Biophys J 73:2615-2629.
45. Niu, S. L., Litman, B. J. (2002). Determination of membrane cholesterol partition coefcient using a lipid vesicle-cyclodextrin binary system: efect of phospholipid acyl chain unsaturation and headgroup composition. Biophys J 83:3408-3415.
46. Ohtani, Y., Irie, T., Uekama, K., Fukunaga, K., Pitha, J. (1989). Diferential efects of alpha-, beta-, and gamma-cyclodextrins on human erythrocytes. Eur J Biochem/FEBS 186:17-22.
47. Ohvo, H., Slotte, J. P. (1996). Cyclodextrin-mediated removal of sterols from monolayers: efects of sterol structure and phospholipids on desorption rate. Biochemistry 35:8018-8024.
48. Pankiewicz, R., Schroeder, G, Brzezinski, B. (2006). Spectroscopic and PM5 semiempirical study of a new lasalocid ester with 2-allyloxyethanol and its complexes with monovalent cations. J Mol Struct 789:1-7. (Pubitemid 43866786)
49. Parthasarathy, R., Gilbert, B., Mehta, B. K. (1999). Aerosol delivery of liposomal all-trans-retinoic acid to the lungs. Cancer Chemother Pharmacol 43:277-283.
50. Perkins, W. R., Minchey, S. R., Ostro, M. J., Taraschi, T. F., Janof, A. S. (1988). The captured volume of multilamellar vesicles. Biochim Biophys Acta 943:103-107.
51. Perkins, W. R., Minchey, S. R., Ahl, P. L., Janof, A. S. (1993). The determination of liposome captured volume. Chem Phys Lipids 64:197-217.
52. Puskás, I., Barcza, L., Szente, L., Csempesz, F. (2006). Features of the interaction between cyclodextrins and colloidal liposomes. J Incl Phenom Macrocycl Chem 54:89-93.
53. Puskás, I., Csempesz, F. (2007). Infuence of cyclodextrins on the physical stability of dipalmitoylphosphatidylcholine liposomes. Coll Surf B Biointerf 58:218-224.
54. Saito, Y., Ueda, H., Abe, M., Sato, T, Christian, S. D. (1998). Inclusion complexation of Triton X-100 with a-, (B-, and y-cyclodextrins. Coll Surf A Physicochem Eng Asp 135:103-108.
55. Schalley, C. A. (2001). Molecular recognition and supramolecular chemistry in the gas phase. Mass Spectrom Rev 20:253-309.
56. Scherphof, G, Roerdinck, F., Waite, M., Parks, J. (1978). Disintegration of phosphatidylcholine liposomes in plasma as a result of interaction with high-density lipoproteins. Biochim Biophys Acta 542:296-307.
57. Silvander, M., Bergstrand, N., Edwards, K. (2003). Linkage identity is a major factor in determining the efect of PEG-ylated surfactants on permeability of phosphatidylcholine liposomes. Chem Phys Lipids 126:77-83.
58. Sriwongsitanont, S., Ueno, M. (2004). Effect of a PEG lipid (DSPE-PEG2000) and freeze-thawing process on phospholipid vesicle size and lamellarity. Colloid Polym Sci 282:753-760.
59. Tirosh, O., Barenholz, Y., Katzhendler, J., Priev, A. (1998). Hydration of polyethylene glycol-grafted liposomes. Biophys J 4:1371-1379.
60. Udachin, K. A., Wilson, L. D., Ripmeester, J. A. (2000). Solid poly-rotaxanes of polyethylene glycol and cyclodextrins: the single-crystal X-ray structure of PEG-p-cyclodextrin. J Am Chem Soc 122:12375-12376.
61. van Winden, E. C. A., Zuidam, N. J., Crommelin, D. J. A. (1998). Medical applications of liposomes. Amsterdam, The Netherlands: Elsevier.
62. Walde, P., Ichikawa, S. (2001). Enzymes inside lipid vesicles: preparation, reactivity, and applications. Biomol Eng 18:143-177.
63. Woodle, M. C. (1995). Sterically stabilized liposome therapeutics. Adv Drug Deliv Rev 16:249-266.
64. Wu, A., Shen, X., He, Y (2006). Investigation on grgamma-cyclodextrin nanotube induced by N,N'-diphenylbenzidine molecule. J Coll Interf Sci 297:525-533.
65. 2+ coordination centers. Chem Mater 18:4423-4429.