The influence of cholesterol and charge on the membrane domains of alkylphospholipid liposomes as studied by EPR

Journal of Liposome Research

Volumn 12, Issue 4, 2002, Pages 335-352

  Koklic, T ^a   Sentjurc M ^a   Zeisig, R ^b  

^a JO EF STEFAN INSTITUTE   (Slovenia)

^b MAX DELBRÜCK CENTER FOR MOLECULAR MEDICINE   (Germany)

Author keywords

Alkylphospholipid; Anticancer activity; Electron paramagnetic resonance; Liposome; Membrane domain structure

Indexed keywords

CHOLESTEROL; LIPOSOME; OCTADECYL (1,1 DIMETHYL 4 PIPERIDINO 4 YL)PHOSPHATE; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CELL MEMBRANE FLUIDITY; CONTROLLED STUDY; CYTOTOXICITY; DIFFUSION; DRUG FORMULATION; ELECTRIC CONDUCTIVITY; ELECTRON SPIN RESONANCE; HUMAN; HUMAN CELL; MEMBRANE FLUIDITY; MEMBRANE VESICLE; MICELLE; MOLECULAR INTERACTION; PARTICLE SIZE; PRIORITY JOURNAL; PROTEIN DOMAIN; STEREOSPECIFICITY;

CELL MEMBRANE; CHOLESTEROL; ELECTRON SPIN RESONANCE SPECTROSCOPY; ELECTROSTATICS; LIPOSOMES; PHOSPHOLIPIDS; POLYETHYLENE GLYCOLS; TEMPERATURE;

EID: 0036913369     PISSN: 08982104     EISSN: None     Source Type: Journal    
DOI: 10.1081/LPR-120016198     Document Type: Article

References (32)

1. Bange, J.; Zwick, E.; Ullrich, A. Molecular targets for breast cancer therapy and prevention. Nat. Med. 2001, 7(5), 548-552.
2. Fichtner, I.; Naundorf, H.; Saul, G.; Zschiesche, W.; Zeisig, R. Establishment and characterisation of human xenotransplanted breast carcinoma lines: Use for the screening of alkylphospholipids. In: Immundeficient Animals: Models for Cancer Research; Köpf-Meier, P., Micheel, B., Eds.; Contrib Oncol. Karger: Basel, 1996; Vol. 51, 129-133.
3. Zeisig, R.; Müller, K.; Maurer, N.; Arndt, D.; Fahr, A. The composition-dependent presence of free (micellar) alkylphospholipid in liposomal formulations of octadecyl-1,1-dimethyl-piperidino-4-yl-phosphate affects its cytotoxic activity in vitro. J. Membrane Biol. 2001, 182(1), 61-69.
4. Berger, M.R.; Yanapirut, P.; Reinhardt, M.; Klenner, T.; Scherf, H.R.; Schmeiser, H.H.; Eibl, H. Antitumor activity of alkylphosphocholines and analogues in methylnitrosourea-induced rat mammary carcinomas. In Alkylphospholipids: New Drugs in Cancer Therapy; Eibl, H., Unger, C., Eds.; Prog. Exp Tumor Res. Karger: Basel, 1992; Vol. 34, 98-115.
5. Hilgard, P.; Klenner, T.; Stekar, J.; Unger, C. Alkylphosphocholines: A new class of membrane-active anticancer agents. Cancer Chemother. Pharmacol. 1993, 32(2), 90-95.
6. Zeisig, R.; Arndt, D.; Stahn, R.; Fichtner, I. Physical properties and pharmacological activity in vitro and in vivo of optimised liposomes prepared from a new cancerostatic alkylphospholipid. Biochim. Biophys. Acta 1998, 1414(1-2), 238-248.
7. Zeisig, R.; Fichtner, I.; Arndt, D.; Jungmann, S. Antitumor Effects of alkylphospho-cholines in different murine tumor models: Use of liposomal preparations. Anticancer Drugs 1991, 2(4), 411-417.
8. Mayhew, E.; Ahmad, I.; Bhatia, S.; Dause, R.; Filep, J.; Janoff, A.S. Stability of association of 1-O-octadecyl-2-O-methyl-s,n-glycero-3-phosphocholine with liposomes is composition dependent. Biochim. Biophys. Acta 1997, 1329(1), 139-148.
9. Kaufmann-Kolle, P.; Unger, C.; Eibl, H. Hexadecylphosphocholine in liposomal dispersions. In Alkylphospholipids: New Drugs in Cancer Therapy; Eibl, H., Unger, C., Eds.; Prog. Exp Tumor Res. Karger: Basel, 1992; Vol. 34, 12-24.
10. Bloom, M. The physics of soft, natural materials. Phys. in Canada 1992, 48, 7-16.
11. Zeisig, R.; Eue, I.; Kosch, M.; Fichtner, I.; Arndt, D. Preparation and properties of sterically stabilized hexadecylphosphocholine (miltefosine)-liposomes and influence of this modification on macrophage activation. Biochim. Biophys. Acta 1996, 1283(2), 177-184.
12. Griffith, O.H.; Jost, P.C. Lipid spin labels in biological membranes. In Spin Labeling, Theory and Application; Berliner, L.J., Ed.; Academic Press: New York, 1976; 453-523.
13. Strancar, J.; Sentjurc, M.; Schara, M. Fast and accurate characterization of biological membranes by EPR spectral simulations of nitroxides. J. Magn. Reson. 2000, 142(2), 254-265.
14. Zuvic-Butorac, M.; Muller, P.; Pomorski, T.; Libera, J.; Herrmann, A.; Schara, M. Lipid domains in the exoplasmic and cytoplasmic leaflet of the human erythrocyte membrane: A spin label approach. Eur. Biophys. J. 1999, 28(4), 302-311.
15. Cader, A.A.; Butterfield, D.A.; Watkins, B.A.; Chung, B.H.; Hennig, B. Electron spin resonance studies of fatty acid-induced alterations in membrane fluidity in cultured endothelial cells. Int. J. Biochem. Cell Biol. 1995, 27(7), 665-673.
16. Knowles, P.F.; Marsh, D.; Rattle, H.W.E. Magnetic Resonance of Biomolecules. An Introduction to the Theory and Practice of NMR and ESR in Biological Systems; John Wiley & Sons: London, 1976; 197-197.
17. Filipic, B.; Strancar, J. Tuning EPR spectral parameters with a genetic algorithm. Appl. Soft Computing 2001, 1(1), 83-90.
18. Hilgard, P.; Stekar, J.; Klenner, T.; Nössner, B.; Kutscher, B.; Engel, J. Heterocyclic alkylphospholipids with an improved therapeutic range. Adv. Exp. Med. Biol. 1996, 416, 157-164.
19. Stekar, J.; Hilgard, P.; Voegeli, R.; Maurer, H.R.; Engel, J.; Kutscher, B. Antineoplastic activity and tolerability of a novel heterocyclic alkylphospholipid, D-20133. Cancer Chemother. Pharmacol. 1993, 32(6), 437-444.
20. Fichtner, I.; Zeisig, R.; Naundorf, H.; Jungmann, S.; Arndt, D.; Asongwe, G. Antineoplastic activity of alkylphosphocholines (APC) in human breast carcinomas in vivo and in vitro; use of liposomes. Breast Cancer Res. Treat 1994, 32(3), 269-279.
21. Jain, M.K.; van Echteld, C.J.; Ramirez, F.; de Gier, J.; de Haas, G.H.; van Deenen, L.L. Association of lysophosphatidylcholine with fatty acids in aqueous phase to form bilayers. Nature 1980, 284(5755), 486-487.
22. Perkins, W.R.; Dause, R.B.; Li, X.; Franklin, J.C.; Cabral-Lilly, D.J.; Zha, Y. Combination of antitumor ether lipid with lipids of complementary molecular shape reduces its hemolytic activity. Biochim. Biophys. Acta 1997, 1327(1), 61-68.
23. Carnie, S.; Israelachvili, J.N.; Pailthorpe, B.A. Lipid packing and transbilayer asymmetries of mixed lipid vesicles. Biochim. Biophys. Acta 1979, 554(2), 340-357.
24. Israelachvili, J.N.; Marcelja, S.; Horn, R.G. Physical principles of membrane organization. Q. Rev. Biophys. 1980, 13(2), 121-200.
25. Arndt, D.; Zeisig, R.; Fichtner, I.; Teppke, A.-D.; Fahr, A. Pharmacokinetics of sterically stabilized hexadecylphosphocholine liposomes versus conventional liposomes and free hexadecylphosphocholine in tumor-free and human breast carcinoma bearing mice. Breast Cancer Res. Treat. 1999, 58(1), 71-80.
26. Allen, T.M. Long-circulating (sterically stabilized) liposomes for targeted drug delivery. Trends Pharmacol. Sci. 1994, 15(7), 215-220.
27. Zeisig, R.; Jungmann, S.; Arndt, D.; Schütt, A.; Nissen, E. Antineoplastic activity in vitro of free and liposomal alkylphosphocholines. Anticancer Drugs 1993, 4(1), 57-64.
28. Huang, S.K.; Mayhew, E.; Gilani, S.; Lasic, D.D.; Martin, F.J.; Papahadjopoulos, D. Pharmacokinetics and therapeutics of sterically stabilized liposomes in mice bearing C-26 colon carcinoma. Cancer Res. 1992, 52(24), 6774-6781.
29. McMullen, T.P.; Lewis, R.N.; McElhaney, R.N. Differential scanning calorimetric and fourier transform infrared spectroscopic studies of the effects of cholesterol on the thermotropic phase behavior and organization of a homologous series of linear saturated phosphatidylserine bilayer membranes. Biophys. J. 2000, 79(4), 2056-2065.
30. Sentjurc, M.; Schara, M.; Nemec, M. Interaction of liposomes with other lipid bilayers. Studia. Biophys. 1984, 103, 81-87.
31. Sentjurc, M.; Kocevar, M.; Honzak, L. Role of cholesterol in the transport of liposome encapsulated substances into the skin. Progress in Drug Delivery System 1996, V, 157-160.
32. Vrhovnik, K.; Kristl, J.; Sentjurc, M.; Smid-Korbar, J. Influence of liposome bilayer fluidity on the transport of encapsulated substance into the skin as evaluated by EPR. Pharm. Res. 1998, 15(4), 525-530.