Interactions of Amphotericin B derivative of low toxicity with biological membrane components - The Langmuir monolayer approach

Biophysical Chemistry

Volumn 116, Issue 1, 2005, Pages 77-88

  Hac Wydro K ^a   Dynarowicz Latka P ^a   Grzybowska, J ^b   Borowski, E ^b  

^a JAGIELLONIAN UNIVERSITY   (Poland)

^b GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Air water interface; Amphotericin B derivatives; Interactions; Langmuir monolayers; Mixed monolayers

Indexed keywords

AMPHOTERICIN B DERIVATIVE; CHOLESTEROL; DIPALMITOYLPHOSPHATIDYLCHOLINE; ERGOSTEROL; N METHYL N DEXTRO FRUCTOPYRANOSYLAMPHOTERICIN B METHYL ESTER; PHOSPHOLIPID; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CELL MEMBRANE; CONCENTRATION RESPONSE; LANGMUIR BLODGETT FILM; MOLECULAR INTERACTION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL;

AMPHOTERICIN B; ANIMALS; ANTIFUNGAL AGENTS; CELL MEMBRANE; METHYL ETHERS; MOLECULAR STRUCTURE; PHOSPHOLIPIDS; STEROLS; TEMPERATURE; WATER;

ANIMALIA; FUNGI; MAMMALIA;

EID: 19444375273     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bpc.2005.03.001     Document Type: Article

References (54)

1. G.J. Gaines I. Prigogine Insoluble Monolayers at Liquid-Gas Interfaces 1966 J. Wiley and Sons New York
2. A.A. Hidalgo, W. Caetano, M. Tabak, and O.N. Oliveira Jr. Interaction of two phenothiazine derivatives with phospholipids monolayers Biophys. Chemist. 109 2004 85 104
3. S.M.B. Souza, O.N. Oliveira, M.V. Scarpa, and A.G. Oliveira Study of the diclofenac/phospholipids interactions with liposomes and monolayers Coll. Surf. B: Biointerfaces 36 2004 13 17
4. G. Beurer, and H.J. Galla Eur. Biophys. J. 14 1987 403
5. J. Miñones Jr., and J. Miñones Recent studies on amphotericin B-phospholipids interactions in Langmuir monolayers Recent Res. Dev. Surf. Colloids 1 2004 21 42
6. N. Vila Romeu, J. Miñones, O. Conde, M. Casas, and E. Iribarnegaray Mixed calcitonin-poly[(d,l-lactic acid)-co-(glycolic acid)] monolayers Langmuir 13 1997 76 79
7. H. Ohvo-Rekila, P. Mattjus, and J.P. Slotte The influence of hydrophobic mismatch on androsterol/phosphatidylcholine interactions in model membranes Biochim. Biophys. Acta 1372 1998 331 338
8. F. Gambinossi, M. Pugelli, and G. Gabrielli Enzymatic hydrolysis reaction of phospholipids in monolayers Colloids Surf., B Biointerfaces 23 2002 273 281
9. J. Zhang, V. Rosilio, M. Goldmann, M.M. Boissonnade, and A. Baszkin Adsorption of glucose oxidase into lipid monolayers. Effect of lipid chain lengths on the stability and structure of mixed enzyme/phospholipid films Langmuir 16 2000 1226 1232
10. V. Rosilio, M.M. Boissonnade, J. Zhang, L. Jiang, and A. Baszkin Penetration of glucose oxidase into organized phospholipid monolayers spread at the solution/air interface Langmuir 13 1997 4669 4675
11. A. Baszkin, M.M. Boissonnade, V. Rosilio, A. Kamyshny, and S. Magdassi Penetration of glucose oxidase and of the hydrophobically modified enzyme into phospholipid and cholesterol monolayers J. Colloid Interface Sci. 209 1999 302 311
12. W.P. Ulrich, and H. Volgel Polarization-modulated FTIR spectroscopy of lipid/gramicidin monolayers at the water interface Biophys. J. 76 1999 1639 1647
13. G.D. Fidelio, B. Maggio, and F.A. Cumar Interaction of melittin with glycosphingolipids and phospholipids in mixed monolayers at different temperatures. Effect of the lipid physical state Biochim. Biophys. Acta 862 1986 49 56
14. 2 Biochemistry 33 1994 6659 6670
15. R. Maget-Dana, and M. Ptak Penetration of the insect defensin A into phospholipid monolayers and formation of defensin A-lipid complexes Biophys. J. 73 1997 2527 2533
16. M. Saint-Pierre-Chazalet, C. Fressigne, F. Billoudet, and M.P. Pileni Phospholipid-protein interactions at the air-water interface: a monolayer study Thin Solid Films 210/211 1992 743
17. H. Abriouel, J. Sanchez-Gonzalez, M. Maqueda, A. Galvez, E. Valdivia, and M.J. Galvez-Ruiz Monolayer characteristics of bacteriocin AS-48, pH effect and interactions with dipalmitoyl phosphatidic acid at the air-water interface J. Colloid Interface Sci. 233 2001 306 312
18. M.A. Bos, and T. Nylander Interaction between beta-lactoglobulin and phospholipids at the air/water interface Langmuir 12 1996 2791 2797
19. J. Zhao, D. Vollhardt, G. Brezesinski, S. Siegel, J. Wu, J.B. Li, and R. Miller Effect of protein penetration into phospholipid monolayers: morphology and structure Colloids Surf., A Physicochem. Eng. Asp. 171 2000 175 184
20. X. Wang, Y. Zhang, J. Wu, M. Wang, G. Cui, J. Li, and G. Brezesinski Dynamical and morphological studies on the adsorption and penetration of human serum albumin into phospholipid monolayers at the air/water interface Colloids Surf., B Biointerfaces 23 2002 339 347
21. D.L. Schwinke, M.G. Ganesan, and N.D. Weiner J. Pharm. Sci. 72 1983 244 248
22. M. Saint-Pierre-Chazalet, C. Thomas, M. Dupeyrat, and C. Gary-Bobo Amphotericin B-sterol complex formation and competition with egg phosphatidylcholine: a monolayer study Biochim. Biophys. Acta 944 1988 477 486
23. J. Barwicz, and P. Tancrede The effect of aggregation state of amphotericin B on its interactions with cholesterol- or ergosterol-containing phosphatidylcholine monolayers Chem. Phys. Lipids 85 1997 145 155
24. R. Seoane, J. Miñones, O. Conde, M. Casas, and E. Iribarnegaray Molecular organization of amphotericin B at the air-water interface in the presence of sterols: a monolayer study Biochim. Biophys. Acta 1375 1998 73 83
25. R. Seoane, J. Miñones, O. Conde, E. Iribarnegaray, and M. Casas Interactions between Amphotericin B and sterols in monolayers. Mixed films of Amphotericin B-cholesterol Langmuir 15 1999 5567 5573
26. R. Seoane, J. Miñones, O. Conde, M. Casas, and E. Iribarnegaray Interactions between Amphotericin B and sterols in monolayers. Mixed films of ergosterol-Amphotericin B Langmuir 15 1999 3570 3578
27. I. Rey Gómez-Serranillos, J. Miñones Jr., P. Dynarowicz-Ła̧tka, J. Miñones, and E. Iribarnegaray Miltefosine-cholesterol interactions: a monolayer study Langmuir 20 2004 928 933
28. I. Rey Gómez-Serranillos, J. Miñones Jr., P. Dynarowicz-Ła̧tka, J. Miñones, and O Conde Surface behaviour of oleoyl Palmitoyl Phosphatidyl Ethanoloamine (OPPE) and the characteristic of mixed OPPE-miltefosine monolayers Langmuir 20 2004 11414
29. R. Seoane, P. Dynarowicz-Ła̧tka, J. Miñones Jr., and I. Rey-Gómez-Serranillos Mixed Langmuir monolayers of cholesterol and 'essential' fatty acids Colloid Polym. Sci. 279 2001 562 570
30. R. Maget-Dana The monolayer technique: a potent tool for studying the interfacial properties of antimicrobial and membrane-lytic peptides and their interactions with lipid membranes Biochim. Biophys. Acta 1462 1999 109 140
31. I. Weis, P.B. Welzel, G. Bähr, and G. Schwarz Equations of state for POPX lipids at the air/water interface. A comprehensive study Chem. Phys. Lipids 105 2000 1 8
32. P. Dynarowicz-Ła̧tka, R. Seoane, J. Miñones Jr., and M. Velo Study of penetration of amphotericin B into cholesterol or ergosterol containing dipalmitoyl phosphatidylcholine Langmuir monolayers Coll. Surf. B 27 2002 249 263
33. P. Dynarowicz-Ła̧tka, and K. Kita Molecular interaction in mixed monolayers at the air/water interface Adv. Colloid Interface Sci. 79 1999 1 17
34. J. Bolard How do the polyene macrolide antibiotics affect the cellular membrane properties Biochim. Biophys. Acta 846 1986 257 304
35. S.B. Zotchev Polyene macrolide antibiotics and their application in human therapy Curr. Med. Chem. 10 2003 211 223
36. J. Miñones Jr., O. Conde, J. Miñones, J.M. Rodriguez Patino, and R. Seoane Amphotericin B-Dipalmitoyl phosphatidyl glycerol interactions responsible for the reduced toxicity of liposomal formulations: a monolayer study Langmuir 18 2002 8601 8608
37. B. Dupont Overview of the lipid formulations of amphotericin B J. Antimicrob. Chemother. 49 2002 31 36
38. M. Cheron, B. Cybulska, J. Mazurski, J. Grzybowiska, and E. Borowski Quantitative structure-activity relationship in amphotericin B derivatives Biochem. Pharmacol. 37 1998 827 836
39. E. Borowski Novel approaches in the rational design of antifungal agents of low toxicity IL Farmaco 55 2000 206 208
40. A. Jarzebski, L. Falkowski, and E. Borowski J. Antibiot. 35 1982 220 229
41. J. Bolard, C. Garcia, O. Seksek, E. Borowski, J. Grzybowska, Polish Pat. Appl. P-343365 (1999).
42. J. Grzybowska, P. Sowiński, J. Gumieniak, T. Zieniawa, and E. Borowski N-methyl-N-d-fructopyranosyl amphotericin B metyl ester, New amphotericin B derivative of low toxicity J. Antibiot. 50 1997 709 711
43. B. DeKruijf, and R.A. Demel Polyene antibiotic-sterol interactions in membranes of acholeplasma laidlawii cells and lecithin liposomes: III. Molecular structure of the polyene antibiotic-cholesterol complexes Biochim. Biophys. Acta 339 1974 57 70
44. M. Bagiński, H. Resat, and E. Borowski Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels Biochim. Biophys. Acta 1567 2002 63 78
45. H. Theorell, and E. Stenhagen Biochem. Z. 299 1939 417
46. I. Rey-Gomez-Serranillos, J. Miñones Jr., R. Seoane, O. Conde, and M. Casas A study of the stability of amphotericin B monolayers Prog. Colloid Polym. Sci. 112 1999 29 33
47. J.R. Seoane, N. Vila Romeu, J. Miñones Jr., O. Conde, P. Dynarowicz, and M. Casas The behaviour of amphotericin B monolayers at the air/water interface Prog. Colloid Polym. Sci. 105 1997 173 179
48. HyperChem Professional Release 5.1., A Molecular Visualization and Simulation Software Package 1998 Hypercube Inc. Gainesville, FL
49. J.T. Davies, and E.K. Rideal Interfacial Phenomena 1963 Academic Press New York
50. D. Chapman Biomembranes and new hemocompatible materials Langmuir 9 1993 39 45
51. J. Szlinder-Richter, B. Cybulska, J. Grzybowska, J. Bilard, and E. Borowski Interaction of amphotericin B and its low toxic derivative, N-methyl-N-d-fructosyl amphotericin B methyl ester, with fungal, mammalian and bacterial cells measured by the energy transfer method IL Farmaco 59 2004 289 296
52. J. Szlinder-Richter, J. Mazerski, B. Cybulska, J. Grzybowska, and E. Borowski MFAME, N-methyl-N-d-fructosyl amphotericin B methyl ester, a new amphotericin B derivative of low toxicity: relationship between self-association and effects on red blood cells Biochim. Biophys. Acta 1528 2001 15 24
53. M. Ślisz, B. Cybulska, J. Mazerski, J. Grzybowska, and E. Borowski Studies on the effect of antifungal cationic derivatives of amphotericin B on human erythrocytes J. Antibiot. 57 2004 669 678
54. M. Bagiński, A. Tempczyk, and E. Borowski Comparative conformational analysis of cholesterol and ergosterol by molecular mechanics Eur. Biophys. J. 17 1989 159 166