Benzophenone-containing cholesterol surrogates

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

Journal of Lipid Research (Aug 2004)

Benzophenone-containing cholesterol surrogates

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

Affiliations

Thomas A. Spencer: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Pingzhen Wang: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Dansu Li: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Jonathon S. Russel: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
David H. Blank: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Jarkko Huuskonen: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Phoebe E. Fielding: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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
Christopher J. Fielding: Department of Chemistry, Dartmouth College, Hanover, NH 03755; 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

Journal volume & issue: Vol. 45, no. 8
pp. 1510 – 1518

Abstract

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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.

Published in Journal of Lipid Research

ISSN: 0022-2275 (Print); 1539-7262 (Online)
Publisher: Elsevier
Country of publisher: United States
LCC subjects: Science: Chemistry: Organic chemistry: Biochemistry
Website: https://www.journals.elsevier.com/journal-of-lipid-research

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