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A more recent version of this article appeared on August 1, 2004

Papers In Press, published online ahead of print June 1, 2004
J. Lipid Res., doi:10.1194/jlr.M400081-JLR200
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Submitted on February 26, 2004
Revised on May 21, 2004
Accepted on May 21, 2004

Benzophenone-containing cholesterol surrogates:Synthesis and biological evaluation

Thomas A. Spencer, Pingzhen Wang, Dansu Li, Jonathon S. Russel, David H. Blank, Jarkko Huuskonen, Phoebe E. Fielding, and Christopher J. Fielding

Dartmouth College, Hanover, NH 03755

Corresponding Author: taspen{at}dartmouth.edu

Eight analogs of cholesterol (1) containing a benzophenone group have been synthesized as prospective photoaffinity labels for studies of cellular sterol efflux and high density lipoprotein (HDL) formation. Six of these compounds (4-9) have the photophore replacing different portions of the cholesterol alkyl side chain and two (10 and 11) have it attached via nitrogen at C3. The suitability of these analogs as cholesterol surrogates was determined by examining their ability to replace 3H-1 in fibroblasts pre-equilibrated with 3H-1. All eight analogs were effective in replacing natural 1 in competition with 3H-1 for apolipoprotein A-I (apo A-I) induced efflux. These are the first compounds shown to replace cholesterol successfully in a complex pathway of multiple intracellular steps. The results suggest an unexpected plasticity of biological membranes regarding the incorporation of sterols of differing chemical structure.


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