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1. Robalo JR, do Canto AM, Carvalho AJ, Ramalho JP, Loura LM: Behavior of fluorescent cholesterol analogues dehydroergosterol and cholestatrienol in lipid bilayers: a molecular dynamics study. J Phys Chem B; 2013 May 16;117(19):5806-19
Hazardous Substances Data Bank. CHOLESTEROL .

  • [Source] The source of this record is MEDLINE®, a database of the U.S. National Library of Medicine.
  • [Title] Behavior of fluorescent cholesterol analogues dehydroergosterol and cholestatrienol in lipid bilayers: a molecular dynamics study.
  • Molecular dynamics simulations of bilayer systems consisting of varying proportions of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC), cholesterol (Chol), and intrinsically fluorescent Chol analogues dehydroergosterol (DHE) or cholestatrienol (CTL) were carried out to study in detail the extent to which these fluorescent probes mimic Chol's behavior (location, orientation, dynamics) in membranes as well as their effect on host bilayer structure and dynamics (namely their ability to induce membrane ordering in comparison with Chol).
  • Control properties of POPC and POPC/Chol bilayers agree well with published experimental and simulation work.
  • Both probes and Chol share similar structural and dynamical properties within the bilayers.
  • Additionally, the fluorescent sterols induce membrane ordering to a similar (slightly lower) extent to that of Chol.
  • These findings combined demonstrate that the two studied fluorescent sterols are adequate analogues of Chol, and may be used with advantage over side-chain labeled sterols.
  • The small structural differences between the three studied sterols are responsible for the slight variations in the calculated properties, with CTL presenting a more similar behavior to Chol (correlating with its larger structural similarity to Chol) compared to DHE.
  • [MeSH-major] Cholestenes / chemistry. Cholesterol / analogs & derivatives. Ergosterol / analogs & derivatives. Fluorescent Dyes / chemistry. Lipid Bilayers / metabolism. Molecular Dynamics Simulation
  • [MeSH-minor] Molecular Conformation. Phosphatidylcholines / chemistry. Phosphatidylcholines / metabolism

  • MedlinePlus Health Information. consumer health - Cholesterol.
  • Hazardous Substances Data Bank. ERGOSTEROL .
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  • (PMID = 23597397.001).
  • [ISSN] 1520-5207
  • [Journal-full-title] The journal of physical chemistry. B
  • [ISO-abbreviation] J Phys Chem B
  • [Language] eng
  • [Publication-type] Journal Article; Research Support, Non-U.S. Gov't
  • [Publication-country] United States
  • [Chemical-registry-number] 0 / Cholestenes; 0 / Fluorescent Dyes; 0 / Lipid Bilayers; 0 / Phosphatidylcholines; 123R6KJQ51 / dehydroergosterol; 51982-45-7 / cholesta-5,7,9-trien-3 beta-ol; 97C5T2UQ7J / Cholesterol; TE895536Y5 / 1-palmitoyl-2-oleoylphosphatidylcholine; Z30RAY509F / Ergosterol
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