Preferences help
enabled [disable] Abstract
Number of results
2005 | 52 | 3 | 655-658
Article title

Molecular modelling of membrane activity of amphotericin B, a polyene macrolide antifungal antibiotic

Title variants
Languages of publication
Amphotericin B (AmB) is a well known polyene macrolide antibiotic used to treat systemic fungal infections. Despite its toxicity AmB is still regarded as a life-saving drug. The lack of adequate knowledge of the AmB mechanism of action is a serious obstacle to efficient development of new less toxic derivatives. Complementary to various experimental approaches, computational chemistry methods were used to study AmB mechanism of action. A programme lasting for a decade, that was run by our group covered studies of: i) molecular properties of AmB and its membrane targets, ii) structure and properties of AmB membrane channels, and iii) interaction of AmB with the membrane.
Physical description
  • Baginski M (1995) Studies of selected molecular properties of amphotericin B and its cellular targets by theoretical chemistry methods. PhD Thesis. Technical University of Gdansk, Gdansk, Poland.
  • Baginski M, Borowski E (1997) Distribution of electrostatic potential around amphotericin B and its membrane targets. Theochem J Mol Struct 389: 139-146.
  • Baginski M, Tempczyk A, Borowski E (1989) Comparative conformational analysis of cholesterol and ergosterol by molecular mechanics. Eur Biophys J 17: 159-166.
  • Baginski M, Bruni P, Borowski E (1994) Comparative analysis of the distribution of the molecular electrostatic potential for cholesterol and ergosterol. Theochem J Mol Struct 311: 285-296.
  • Baginski M, Gariboldi P, Bruni P, Borowski E (1997a) Conformational analysis of amphotericin B. Biophys Chem 65: 91-100.
  • Baginski M, Resat H, McCammon JA (1997b) Molecular properties of amphotericin B membrane channel: A molecular dynamics simulation. Mol Pharmacol 52: 560-570.
  • Baginski M, Resat H, Borowski E (2002) Comparative molecular dynamics simulations of amphotericin B-cholesterol/ergosterol membrane channels. Biochim Biophys Acta 1567: 63-78.
  • Baran M, Mazerski J (2002) Molecular modelling of amphotericin B-ergosterol primary complex in water. Biophys Chem 95: 125-133.
  • Berges J, Caillet J, Langlet J, Gresh N, Herve M, Gary-Bobo CM (1990) Conformational study of the polar head of the amphotericin B in the isolated state and in the presence of water molecules. Stud Phys Theoret Chem 71: 253-263.
  • Bolard J (1986) How do the polyene macrolide antibiotics affect the cellular membrane properties? Biochim Biophys Acta 864: 257-304.
  • Borowski E (2000) Novel approaches in the rational design of antifungal agents of low toxicity. Il Farmaco 55: 206-208.
  • De Kruijff B, Demel RA (1974) 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: 57-70.
  • Gale EF (1984) Mode of action and resistance mechanisms of polyene macrolides. In Macrolide Antibiotics. Omura S, eds, pp 425-455. Academic Press, Inc., Orlando.
  • Gallis HA, Drew RH, Pickard WW (1990) Amphotericin B: 30 years of clinical experience. Rev Infect Dis 12: 308-329.
  • Hartsel S, Bolard J (1996) Amphotericin B: new life for an old drug. Trends Pharmacol Sci 17: 445-449.
  • Hartsel SC, Hatch C, Ayenew W (1993) How does amphotericin B work?: Studies on model membrane systems. J Liposome Res 3: 377-408.
  • Kerridge D (1986) Mode of action of clinically important antifungal drugs. Adv Microb Physiol 27: 1-72.
  • Kotler-Brajtburg J, Price HD, Medoff G, Schlessinger D, Kobayashi GS (1974) Molecular basis for the selective toxicity of amphotericin B for yeast and filipin for animal cells. Antimicrob Agents Chemother 5: 377-382.
  • Meddeb S, Berges J, Caillet J, Langlet J (1992) Comparative theoretical study of the conformations of amphotericin methyl ester and amphotericin-B polar heads in the presence of water. Biochim Biophys Acta 1112: 266-272.
  • Omura S, Tanaka H (1984) Production, structure, antifungal activity of polyene macrolides. In Macrolide Antibiotics. Omura S, eds, pp 351-404. Academic Press, Inc., Orlando.
  • Resat H, Baginski M (2002) Ion passage pathways and thermodynamics of the amphotericin B membrane channel. Eur Biophys J 31: 294-305.
  • Resat H, Sungur FA, Baginski M, Borowski E, Aviyente V (2000) Conformational properties of amphotericin B amide derivatives - impact on selective toxicity. J Comput Aided Mol Des 14: 689-703.
  • Seoane JR, Vila Romeu N, Minones J, Conde O, Dynarowicz-Latka P, Casas M (1997) The behaviour of amphotericin B monolayers at the air/water interface. Progr Colloid Polym Sci 105: 173-179.
  • Sternal K, Czub J, Baginski M (2004) Molecular aspects of the interaction between amphotericin B and a phospholipid bilayer: molecular dynamics studies. J Mol Model 10: 223-232.
Document Type
Publication order reference
YADDA identifier
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.