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Originally published In Press as doi:10.1194/jlr.M400081-JLR200 on June 1, 2004

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Journal of Lipid Research, Vol. 45, 1510-1518, August 2004
Copyright © 2004 by American Society for Biochemistry and Molecular Biology

Benzophenone-containing cholesterol surrogates

: synthesis and biological evaluation

Thomas A. Spencer1,*, Pingzhen Wang*, Dansu Li*, Jonathon S. Russel*, David H. Blank*, Jarkko Huuskonen§, Phoebe E. Fielding{dagger} and Christopher J. Fielding§

* Department of Chemistry, Dartmouth College, Hanover, NH 03755
{dagger} Cardiovascular Research Institute and Department of Medicine, University of California, San Francisco, CA 94143
§ Cardiovascular Research Institute and Department of Physiology, University of California, San Francisco, CA 94143

1 To whom correspondence should be addressed. e-mail: taspen{at}dartmouth.edu

Eight analogs of cholesterol (1) containing a benzophenone group have been synthesized as prospective photoaffinity labels for studies in cellular sterol efflux and 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 carbon 3. The suitability of these analogs as cholesterol surrogates was determined by examining their ability to replace [3H]1 in fibroblasts preequilibrated with [3H]1. All eight analogs were effective in replacing natural 1 in competition with [3H]1 for apolipoprotein 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 tolerance of biological membranes regarding the incorporation of sterols of differing chemical structure.

Abbreviations: apoA-I, apolipoprotein A-I; C3, carbon 3; DEAD, diethyl azodicarboxylate; DMF, dimethylformamide; EI-HRMS, electron-impact high resolution mass spectrometry; FC, free cholesterol; FCBP, FC benzophenone; THF, Tetrahydrofuran

Supplementary key words cholesterol • cellular sterol efflux • apolipoprotein A-I • photoactivable sterols • photoaffinity labeling


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