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Free Radic Biol Med. 2015 Jul;84:30-41. doi: 10.1016/j.freeradbiomed.2015.03.006. Epub 2015 Mar 17.

Cholesterol under oxidative stress-How lipid membranes sense oxidation as cholesterol is being replaced by oxysterols.

Author information

  • 1Department of Physics, Tampere University of Technology, P.O. Box 692, FI-33101 Tampere, Finland. Electronic address: waldemar.kulig@tut.fi.
  • 2J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v. v. i., Dolejskova 3, 18223 Prague 8, Czech Republic.
  • 3J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v. v. i., Dolejskova 3, 18223 Prague 8, Czech Republic. Electronic address: piotr.jurkiewicz@jh-inst.cas.cz.
  • 4Department of Physics and Chemistry, University of Oulu, P.O. Box 3000, FI-90014 Oulu, Finland.
  • 5Department of Physics, Tampere University of Technology, P.O. Box 692, FI-33101 Tampere, Finland.
  • 6Department of Physics, Tampere University of Technology, P.O. Box 692, FI-33101 Tampere, Finland; Rudjer Bošković Institute, Division of Organic Chemistry and Biochemistry, POB 180, HR-10002 Zagreb, Croatia.
  • 7J. Heyrovský Institute of Physical Chemistry, Academy of Sciences of the Czech Republic, v. v. i., Dolejskova 3, 18223 Prague 8, Czech Republic; Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic. Electronic address: lukasz.cwiklik@uochb.cas.cz.
  • 8Weill Cornell Medical College, New York, NY 10065, USA.
  • 9Institute of Chemistry and the Fritz Haber Research Center, The Hebrew University of Jerusalem, Jerusalem 91904, Israel.
  • 10Department of Physics, Tampere University of Technology, P.O. Box 692, FI-33101 Tampere, Finland; MEMPHYS-Center for Biomembrane Physics, University of Southern Denmark, Odense, Denmark.
  • 11Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 16610 Prague 6, Czech Republic; Department of Physics, Tampere University of Technology, P.O. Box 692, FI-33101 Tampere, Finland.

Abstract

The behavior of oxysterols in phospholipid membranes and their effects on membrane properties were investigated by means of dynamic light scattering, fluorescence spectroscopy, NMR, and extensive atomistic simulations. Two families of oxysterols were scrutinized-tail-oxidized sterols, which are mostly produced by enzymatic processes, and ring-oxidized sterols, formed mostly via reactions with free radicals. The former family of sterols was found to behave similar to cholesterol in terms of molecular orientation, roughly parallel to the bilayer normal, leading to increasing membrane stiffness and suppression of its membrane permeability. In contrast, ring-oxidized sterols behave quantitatively differently from cholesterol. They acquire tilted orientations and therefore disrupt the bilayer structure with potential implications for signaling and other biochemical processes in the membranes.

KEYWORDS:

DPH anisotropy; Laurdan fluorescence; Liposomes; Molecular dynamics simulations; NMR measurements; Oxysterols; Phospholipid bilayers; Tilt modulus

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