Spectroscopic studies of molecular organization of antibiotic amphotericin B in monolayers and dipalmitoylphosphatidylcholine lipid multibilayers

Biochimica et Biophysica Acta - Biomembranes

Volumn 1798, Issue 11, 2010, Pages 2124-2130

  Gagoś, Mariusz ^a   Arczewska, Marta ^a  

^a UNIVERSITY OF LIFE SCIENCES IN LUBLIN   (Poland)

Author keywords

Amphotericin B; Electronic absorption spectroscopy; FTIR spectroscopy; Langmuir Blodgett film lipid multibilayer; Mycosamine

Indexed keywords

AMPHOTERICIN B; DIPALMITOYLPHOSPHATIDYLCHOLINE;

ARTICLE; CONTROLLED STUDY; DRUG STRUCTURE; LIPID BILAYER; LIPID MEMBRANE; LIPID MONOLAYER; PRIORITY JOURNAL; SPECTROSCOPY;

1,2-DIPALMITOYLPHOSPHATIDYLCHOLINE; AMPHOTERICIN B; ANTI-BACTERIAL AGENTS; LIPID BILAYERS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 80052567360     PISSN: 00052736     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbamem.2010.07.037     Document Type: Article

References (54)

1. Halde C., Wright E.T., Pollard W.H., Newcomer V.D., Sternberg T.H. The effect of amphotericin B upon the yeast flora of the gastrointestinal tract of man. Antibiot. Annu. 1956, 123-127.
2. Hartsel S., Bolard J. Amphotericin B: new live for an old drug. TiPS 1996, 17.
3. Gallis H.A., Drew R.H., Pickard W.W. Amphotericin B: 30years of clinical experience. Rev. Infect. Dis. 1990, 12:308-329.
4. Hartsel S.C., Hatch C., Ayenew W. How does amphotericin B work? Studies on model membrane systems. J. Liposome Res. 1993, 3:377-408.
5. Brajtburg J., Powderly W.G., Kobayashi G.S., Medoff G. Amphotericin B: current understanding of mechanisms of action. Antimicrob. Agents Chemother. 1990, 34:183-188.
6. Agarwal R., Singh N. Amphotericin B is still the drug of choice for invasive aspergillosis. Am. J. Respir. Crit. Care Med. 2006, 174:102.
7. Kleinberg M. What is the current and future status of conventional amphotericin B?. Int. J. Antimicrob. Agents 2006, 27(Suppl 1):12-16.
8. Konopka K., Guo L.S.S., Duzgunes N. Anti-HIV activity of amphotericin B-cholesteryl sulfate colloidal dispersion in vitro. Antivir. Res. 1999, 42:197-209.
9. Racis S.P., Plescia O.J., Geller H.M., Schaffner C.P. Comparative toxicities of amphotericin B and its monomethyl ester derivative on glial cells in culture. Antimicrob. Agents Chemother. 1990, 34:1360-1365.
10. De Kruijff B., Gerritsen W.J., Oerlemans A., Demel R.A., van Deenen L.L. Polyene antibiotic-sterol interactions in membranes of Acholeplasma laidlawii cells and lecithin liposomes. I. Specificity of the membrane permeability changes induced by the polyene antibiotics. Biochim. Biophys. Acta 1974, 339:30-43.
11. Hann I.M., Prentice H.G. Lipid-based amphotericin B: a review of the last 10years of use. Int. J. Antimicrob. Ag. 2001, 17:161-169.
12. Baginski M., Resat H., Borowski E. Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels. Biochim. Biophys. Acta 2002, 1567:63-78.
13. Brajtburg J., Medoff G., Kobayashi G.S., Elberg S. Influence of extracellular K+or Mg2+ on the stages of the antifungal effects of amphotericin B and filipin. Antimicrob. Agents Chemother. 1980, 18:593-597.
14. Brajtburg J., Bolard J. Carrier effects on biological activity of amphotericin B. Clin. Microbiol. Rev. 1996, 9:512-&.
15. Baginski M., Cybulska B., Gruszecki W.I. Interaction of Macrolide Antibiotics with Lipid Membranes. Advances in Planar Lipid Bilayers and Liposomes 2006, vol. 3:269-329. Elsevier Science Publ, Amsterdam.
16. Gruszecki W.I., Gagoś M., Kernen P. Polyene antibiotic amphotericin B in monomolecular layers: spectrophotometric and scanning force microscopic analysis. FEBS Lett. 2002, 524:92-96.
17. Gagoś M., Koper R., Gruszecki W.I. Spectrophotometric analysis of organisation of dipalmitoylphosphatylcholine bilayers containing the polyene antibiotic amphotericin B. Biochim. Biophys. Acta 2001, 1511:90-98.
18. Hereć M., Islamov A., Kuklin A., Gagoś M., Gruszecki W.I. Effect of antibiotic amphotericin B on structural and dynamic properties of lipid membranes formed with egg yolk phosphatidylcholine. Chem. Phys. Lipids 2007, 147:78-86.
19. Gagoś M., Gabrielska J., Dalla Serra M., Gruszecki W.I. Binding of antibiotic amphotericin B to lipid membranes: monomolecular layer technique and linear dichroism-FTIR studies. Mol. Membr. Biol. 2005, 22:433-442.
20. Thomas A.H. Analysis and assay of polyene antifungal antibiotics. A review. Analyst 1976, 101:321-340.
21. Matsumori N., Sawada Y., Murata M. Mycosamine orientation of amphotericin B controlling interaction with ergosterol: sterol-dependent activity of conformation-restricted derivatives with an amino-carbonyl bridge. J. Am. Chem. Soc. 2005, 127:10667-10675.
22. Baginski M., Gariboldi P., Borowski E. The role of amphotericin B amino group basicity in its antifungal action. A theoretical approach. Biophys. Chem. 1994, 49:241-250.
23. Mazerski J., Grzybowska J., Borowski E. Influence of net charge on the aggregation and solubility behaviour of amphotericin B and its derivatives in aqueous media. Eur. Biophys. J. 1990, 18:159-164.
24. Resat H., Sungur F.A., Baginski M., Borowski E., Aviyente V. Conformational properties of amphotericin B amide derivatives-impact on selective toxicity. J. Comput. Aided Mol. Des. 2000, 14:689-703.
25. Baginski M., Gariboldi P., Bruni P., Borowski E. Conformational analysis of Amphotericin B. Biophys. Chem. 1997, 65:91-100.
26. Czub J., Neumann A., Borowski E., Baginski M. Influence of a lipid bilayer on the conformational behavior of amphotericin B derivatives-a molecular dynamics study. Biophys. Chem. 2009, 141:105-116.
27. Berges J., Caillet J., Langlet J., Gresh N., Herve M., Gary-Bobo C.M. Conformation study of the polar head of the amphotericin B in the isolated state and in the presence of water molecules. Stud. Phys. Theoret. Chem. 1990, 71:253-263.
28. Mazerski J., Borowski E. Molecular dynamics of amphotericin B. II. Dimer in water. Biophys. Chem. 1996, 57:205-217.
29. Anachi R.B., Bansal M., Easwaran K.R., Namboodri K., Gaber B.P. Molecular modeling studies on amphotericin B and its complex with phospholipid. J. Biomol. Struct. Dyn. 1995, 12:957-970.
30. Caillet J., Berges J., Langlet J. Theoretical study of the self-association of amphotericin B. Biochim. Biophys. Acta 1995, 1240:179-195.
31. Gruszecki W.I., Sielewiesiuk J. Orientation of xanthophylls in phosphatidylcholine multibilayers. Biochim. Biophys. Acta 1990, 1023:405-412.
32. Kasha M. Energy transfer mechanisms and the molecular exciton model for molecular aggregates. Radiat. Res. 1963, 20:55-71.
33. Minones J., Carrera C., Dynarowicz-ła{ogonek}tka P., Minones J., Conde O., Seoane R., Rodriguez Patino J.M. Orientational changes of amphotericin b in langmuir monolayers observed by brewster angle microscopy. Langmuir 2001, 17:1477-1482.
34. Gagoś M., Gruszecki W.I. Organization of polyene antibiotic amphotericin B at the argon-water interface. Biophys. Chem. 2008, 137:110-115.
35. Gruszecki W.I., Gagoś M., Hereć M. Dimers of polyene antibiotic amphotericin B detected by means of fluorescence spectroscopy: molecular organization in solution and in lipid membranes. J. Photochem. Photobiol. B 2003, 69:49-57.
36. Parkash J., Robblee J.H., Agnew J., Gibbs E., Collings P., Pasternack R.F., de Paula J.C. Depolarized resonance light scattering by porphyrin and chlorophyll a aggregates. Biophys. J. 1998, 74:2089-2099.
37. Gruszecki W.I., Gagoś M., Hereć M., Kernen P. Organization of antibiotic amphotericin B in model lipid membranes. A mini review. Cell. Mol. Biol. Lett. 2003, 8:161-170.
38. Gagoś M., Hereć M., Arczewska M., Czernel G., Dalla Serra M., Gruszecki W.I. Anomalously high aggregation level of the polyene antibiotic amphotericin B in acidic medium: Implications for the biological action. Biophys. Chem. 2008, 136:44-49.
39. Schwartzman G., Asher I., Folen V., Brannon W., Taylor J. Ambiguities in IR and X-ray characterization of amphotericin B. J. Pharm. Sci. 1978, 67:398-400.
40. Espuelas M.S., Legrand P., Irache J.M., Gamazo C., Orecchioni A.M., Devissaguet J.-P., Ygartua P. Poly (ε-caprolacton) nanospheres as an alternative way to reduce amphotericin B toxicity. Internat. J. Pharmaceut. 1997, 158:19-27.
41. Seoane J.R., Vila Romeu N., Miñones J., Conde O., Dynarowicz P., Casas M. The behavior of amphotericin B monolayers at the air/water interface. Prog. Colloid Polym. Sci. 1997, 105:173-179.
42. Bunow M.R., Levin I.W. Vibrational Raman spectra of lipid systems containing amphotericin B. Biochim. Biophys. Acta 1977, 464:202-216.
43. Ridente Y., Aubard J., Bolard J. Absence in amphotericin B-spiked human plasma of the free monomeric drug, as detected by SERS. FEBS Lett. 1999, 446:283-286.
44. Brandenburg K., Seydel U. Vibrational spectroscopy of carbohydrates and glycoconjugates, W. Biomedical, Biochemical and Pharmaceutical Applications 2002, Vol. 5:3481-3507. John Wiley and Sons, Chichester. J.M. Chalmers, P.R. Griffiths (Eds.).
45. Kacurakova M., Wilson R.H. Developments in mid-infrared FT-IR spectroscopy of selected carbohydrates. Carbohydr. Polym. 2001, 44:291-303.
46. Kacurakova M., Mathlouthi M. FTIR and laser-Raman spectra of oligosaccharides in water: characterization of the glycosidic bond. Carbohydr. Res. 1996, 284:145-157.
47. Kovalev I.P., Litvinenko V.I. Investigation of flavonoid glycosides. Chem. Nat. Comp. 1965, 1:178-184.
48. Jencks W.P. From chemistry to biochemistry to catalysis to movement. Annu. Rev. Biochem. 1997, 66:1-18.
49. Lopes S.C., Goormaghtigh E., Cabral B.J., Castanho M.A. Filipin orientation revealed by linear dichroism. Implication for a model of action. J. Am. Chem. Soc. 2004, 126:5396-5402.
50. Gruszecki W.I. Carotenoid Orientation: Role in Membrane Stabilization. Carotenoids in health and disease 2004, vol. 15:151-163. Marcel Dekker AG, Basel.
51. Lopes S., Castanho M.A.R.B. Revealing the orientation of nystatin and amphotericin B in lipidic multilayers by UV-Vis linear dichroism. J. Phys. Chem. B 2002, 106:7278-7282.
52. Bagiński M., Resat H., McCammon J.A. Molecular properties of amphotericin B membrane channel: a molecular dynamics simulation. Mol. Pharmacol. 1997, 52:560-570.
53. Gagoś M. Molecular organization of 2-(2, 4-dihydroxylphenyl)-5, 6-dichlor 1, 3-benzothiazole in monomolecular layers formed with diphytanoylphosphatidylcholine: a linear dichroism-FTIR study. Biochim. Biophys. Acta 2008, 1778:2520-2525.
54. Gabrielska J., Gagoś M., Gubernator J., Gruszecki W.I. Binding of antibiotic amphotericin B to lipid membranes: a 1H NMR study. FEBS Lett. 2006, 580:2677-2685.