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2005 | 52 | 3 |

Tytuł artykułu

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

Warianty tytułu

Języki publikacji

EN

Abstrakty

EN
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.

Wydawca

-

Rocznik

Tom

52

Numer

3

Opis fizyczny

p.655-658,fig.,ref.

Twórcy

autor
  • Gdansk University of Technology, Gdansk, Poland
autor
autor
autor

Bibliografia

  • 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 Biophys Lett 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.

Typ dokumentu

Bibliografia

Identyfikatory

Identyfikator YADDA

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