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Antifungal Agents01:15

Antifungal Agents

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Amphotericin B is a broad-spectrum antifungal agent that exploits structural differences between fungal and mammalian cell membranes. Its amphipathic structure—featuring a hydrophobic polyene-lactone ring and a hydrophilic region containing mycosamine and carboxylic acid groups—enables selective binding to ergosterol, a sterol predominantly found in fungal plasma membranes. This selective interaction underlies the drug’s antifungal activity, although weak binding to...
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Understanding Miltefosine-Membrane Interactions Using Molecular Dynamics Simulations.

Matheus Malta de Sá1,2, Vishnu Sresht1, Carlota Oliveira Rangel-Yagui2

  • 1†Department of Chemical Engineering, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139-4307, United States.

Langmuir : the ACS Journal of Surfaces and Colloids
|March 31, 2015
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Summary
This summary is machine-generated.

Miltefosine, an anticancer drug, preferentially partitions into cholesterol-rich lipid rafts. Molecular dynamics simulations reveal its enhanced permeability in unsaturated bilayers and association with cholesterol, impacting its membrane interaction mechanism.

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Area of Science:

  • Biophysics
  • Computational Chemistry
  • Pharmacology

Background:

  • Miltefosine is an alkylphosphocholine anticancer agent.
  • Understanding its interaction with biological membranes is crucial for drug efficacy.
  • Lipid composition and cholesterol content significantly influence membrane properties.

Purpose of the Study:

  • To calculate the free energies of transfer of miltefosine from water to various lipid bilayers.
  • To investigate the mechanism of miltefosine's interaction with biological membranes.
  • To determine the influence of lipid unsaturation and cholesterol on miltefosine partitioning and transport.

Main Methods:

  • Coarse-grained molecular dynamics simulations.
  • Umbrella sampling to calculate free energies of transfer.
  • Calculation of partition coefficients (K) and permeance values.
  • Free energy calculations for miltefosine-cholesterol complex formation.

Main Results:

  • Miltefosine's partition coefficient (K) is significantly higher in bilayers with increased cholesterol content (e.g., 76.2 for 30% cholesterol).
  • Miltefosine shows a propensity to associate with cholesterol, indicating partitioning into lipid rafts.
  • Permeance values indicate higher miltefosine transport in polyunsaturated, loosely organized bilayers (e.g., DUPC) compared to cholesterol-rich bilayers.

Conclusions:

  • Miltefosine interacts with lipid rafts and cholesterol.
  • Membrane fluidity and lipid unsaturation influence miltefosine permeability.
  • The study provides insights into miltefosine's membrane transport and distribution, relevant for anticancer drug development.