• Corpus ID: 33389686

Fluorocholesterols, in contrast to hydroxycholesterols, exhibit interfacial properties similar to cholesterol.

  title={Fluorocholesterols, in contrast to hydroxycholesterols, exhibit interfacial properties similar to cholesterol.},
  author={John M. Kauffman and Philip W. Westerman and Martin C. Carey},
  journal={Journal of lipid research},
  volume={41 6},
We used an automated Langmuir-Pockels surface balance to characterize the air-water interfacial properties of cholesterol (CH) and its derivatives with hydrophilic OH and F substitutions at isologous sites on the sterol body or side chain. We studied 6-fluorocholesterol, 25-fluorocholesterol, 25,26,26,26,27,27,27-heptafluorocholesterol, 7alpha-hydroxycholesterol, 7beta-hydroxycholesterol, 25-hydroxycholesterol and 27-hydroxycholesterol, alone and in mixtures with 1-palmitoyl-2-oleoyl-sn-3… 

Figures from this paper

Comparison of cholesterol and 25-hydroxycholesterol in phase-separated langmuir monolayers at the air-water interface.
The average molecular packing and micron scale phase separation within a 25OH/phospholipid monolayer is investigated and it is concluded that 25OH and other similar hydroxysterols provide a useful and independent test of cholesterol's behavior within monolayers.
Unusual Behavior of the Bipolar Molecule 25-Hydroxycholesterol at the Air/Water Interface—Langmuir Monolayer Approach Complemented with Theoretical Calculations
The molecular mechanism and interactions stabilizing bilayer structure were proposed and the explanation of the observed unusual surface behavior of 25-OH may contribute to an understanding of differences in biological activity between chain- and ring-oxidized sterols.
Interfacial properties of most monofluorinated bile acids deviate markedly from the natural congeners: studies with the Langmuir-Pockels surface balance.
Examination of molecular models revealed that the 7alpha-F atom of the interfacially stable FMCA projects away from the 6beta-OH function, resulting in minimal steric interactions, whereas in FHDCA, FUDCA, and FCDCA, close vicinal interactions between OH and F polar functions result in progressive bulk solubility upon monolayer compression.
Cholesterol Is Superior to 7-Ketocholesterol or 7α-Hydroxycholesterol as an Allosteric Activator for Acyl-coenzyme A:Cholesterol Acyltransferase 1*
The results suggest that ACAT1 contains two types of sterol binding sites; the structural requirement for the ACAT activator site is more stringent than it is for the APA:cholesterol acyltransferase substrate site.
An Examination of Oxysterol Effects on Membrane Bilayers Using Molecular Dynamics Simulations
This study shows that direct membrane perturbation by side-chain oxysterols is significant, and suggests that these membranes perturbations may play a role in the oxysterol regulation of cholesterol homeostasis.
Oxysterol-induced rearrangement of the liquid-ordered phase: a possible link to Alzheimer's disease?
Whereas partial replacement of cholesterol with 7beta-OH strengthens the association between A and B, a similar substitution with 25-OH weakens this association, and a model that accounts for this dichotomy is discussed.


Cholesterol's interfacial interactions with sphingomyelins and phosphatidylcholines: hydrocarbon chain structure determines the magnitude of condensation.
Cholesterol's interfacial interaction with different sphingomyelins and phosphatidylcholines has been investigated using a Langmuir film balance and the relative importance of phospholipid/sphingoipid hydrocarbon and headgroup structure in determining the extent of interaction with cholesterol is discussed.
Cholesterol condensation of alpha-linolenic and gamma-linolenic acid-containing phosphatidylcholine monolayers and bilayers.
Lipid-cholesterol interaction is used to distinguish the effect of position of unsaturation on membrane structure in monolayers and bilayer membranes.
Bile acid/phosphatidylcholine interactions in mixed monomolecular layers: differences in condensation effects but not interfacial orientation between hydrophobic and hydrophilic bile acid species.
It is inferred that the long axes of the steroid nuclei of dihydroxy bile acids remain parallel to the interface in mixed bile acid/POPC +/- cholesterol monomolecular layers under all conditions and that fully dissociated hydrophobic and, to a lesser extent, hydrophilic bile salts condense phospholipid monomolescular layers and membranes in a similar fashion.
6-Fluorocholesterol as a growth factor for the yeast mutant GL7.
6-Fluorocholesterol supports the growth of the sterol-requiring yeast mutant GL7 albeit less efficiently than cholesterol or ergosterol. When the fluoro analogue is combined with very much smaller
Atherosclerosis and sterol 27-hydroxylase: evidence for a role of this enzyme in elimination of cholesterol from human macrophages.