Use of Cholesteryl Ester Analogs to Study Transport of Lipoproteins in Intact Animals

  • Yechezkiel Stein
  • Yoseph Kleinman
  • Gideon Halperin
  • Olga Stein


Deposition of lipid is one of the major events in the development of atheroma and therefore any attempt to study regression of atheroma faces the problem of quantitation of the lipids present at the various stages of regression. During the past few years we have synthesized labeled analogs of cholesteryl ester (1) and triacylglycerol (2,3) which owing to the replacement of the ester bond by an ether bond are not hydrolyzed by the esterases present in animal tissues. These compounds have been studied in several different systems in vivo and in vitro (3–9) and the data obtained indicate that they can serve as stable markers for the estimation of cholesterol ester deposited in the aortic wall.


Cholesteryl Ester Cholesteryl Ester Transfer Protein Glyceryl Ether Hypercholesterolemic Rabbit Glycerol Ether 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    G. Halperin and S. Gatt, The synthesis of cholesteryl alkyl ethers, Steroids 35: 39 (1980).CrossRefGoogle Scholar
  2. 2.
    F. Paltauf and F. Spener, An improved synthesis of 1,2-dialkyl glycerol ether and the synthesis of 14C-labeled trialkyl glycerol ethers, Chem.Phys.Lipids 2: 168 (1968).CrossRefGoogle Scholar
  3. 3.
    Y. Kleinman, G. Halperin, O. Stein, and Y. Stein, Long-lived labeling of phagocytic cells with analogs of atheroma lipids, Atherosclerosis 43: 1 (1982).CrossRefGoogle Scholar
  4. 4.
    O. Stein, G. Halperin, and Y. Stein, Biological labeling of very low density lipoproteins with cholesteryl linoleyl ether and its fate in the intact rat, Biochim.Biophys.Acta 620: 247 (1980).CrossRefGoogle Scholar
  5. 5.
    Y. Stein, G. Halperin, and O. Stein, The fate of cholesteryl linoleyl ether and cholesteryl linoleate in the intact rat after injection of biologically labeled human low density lipoprotein, Biochim.Biophys.Acta 663: 569 (1981).CrossRefGoogle Scholar
  6. 6.
    T. Chajek-Shaul, G. Friedman. G. Halperin, O. Stein, and Y. Stein, Uptake of chylomicron [3H]cholesteryl linoleyl ether by mesenchymal rat heart cell cultures, Biochim.Biophvs.Acta 666: 147 (1981).CrossRefGoogle Scholar
  7. 7.
    Y. Kleinman, O. Stein, and Y. Stein, Persistence of 3H-trioleyl glyceryl ether in organs of mice treated with glucocorticosteroids, Isr.J.Med.Sci. 18: 819 (1982).Google Scholar
  8. 8.
    Y. Stein, O. Stein, and G. Halperin, The use of 3H-cholesteryl linoleyl ether for the quantitation of plasma cholesteryl ester influx into the aortic wall in hypercholesterolemic rabbits, Arteriosclerosis 2: 281 (1982).CrossRefGoogle Scholar
  9. 9.
    Y. Stein, Y. Kleinman, G. Halperin, and O. Stein. Hepatic retention and elimination of cholesteryl linoleyl ether after injection of laeled acetylated LDL or chylomicrons, Biochim.Biophys.Acta, 750: 300 (1983).CrossRefGoogle Scholar
  10. 10.
    W. Stoll, Eine neue Darstellungsweise von Cholesterinathern, Z.Phys.Chem. 207: 147 (1932).CrossRefGoogle Scholar
  11. 11.
    Y. Stein, G. Halperin, and O. Stein, Biological stability of [3H]cholesteryl oleyl ether in cultured fibroblasts and intact rat, FEBS Leters 111: 104 (1980).CrossRefGoogle Scholar
  12. 12.
    R. J. Havel, H. A. Eder, and J. H. Bragdon, The distribution and chemical composition of ultracentrifugally separated lipoproteins in human serum, J.Clin.Invest. 34: 1345 (1955).CrossRefGoogle Scholar
  13. 13.
    H. Fraenkel-Conrat, Methods for investigating the essential groups for enzyme activity, in: “Methods in Enzymology,” S. P. Colowick and N. O. Kaplan, eds., Academic press Inc., New York (1957).Google Scholar
  14. 14.
    J. L. Goldstein, Y. K. Ho, S. K. Basu, and M. S. Brown, Binding site on macrophages that mediates uptake and degradation of acetylated low density lipoprotein, producing massive cholesterol deposition, Proc.Natl.Acad.Sci. U.S.A. 76: 333 (1979).CrossRefGoogle Scholar
  15. 15.
    R. W. Mahley, K. H. Weisgraber, T. L. Innerarity, and H. G. Windmueller, Accelerated clearance of low-density and high-density lipoproteins and retarded clearance of E apoprotein-containing lipoproteins from the plasma of rats after modification of lysine residues, Proc.Natl.Acad.Sci. U.S.A. 76: 1746 (1979).CrossRefGoogle Scholar
  16. 16.
    O. Stein and Y. Stein, The role of the liver in the metabolism of chylomicrons, studied by electron microscopic autoradiography, Lab.Invest. 17: 436 (1967).Google Scholar
  17. 17.
    O. Stein, Y. Stein, D. S. Goodman, and N. H. Fidge, The metabolism of chylomicron cholesteryl ester in rat liver. A combined radioautographic electron microscopic and biochemical study, J.Cell Biol. 43: 410 (1969).CrossRefGoogle Scholar
  18. 18.
    DeW. S. Goodman, O. Stein, G. Halperin, and Y. Stein, The divergent metabolic fate of ether analogs of cholesteryl and retinyl esters after injection in lymph chylomicrons into rats, Biochim.Biophys.Acta 750: 223 (1983).CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1984

Authors and Affiliations

  • Yechezkiel Stein
    • 1
    • 2
  • Yoseph Kleinman
    • 1
    • 2
  • Gideon Halperin
    • 1
    • 2
  • Olga Stein
    • 1
    • 2
  1. 1.Lipid Research Laboratory, Department of Medicine BHadassah University HospitalJerusalemIsrael
  2. 2.Department of Experimental Medicine and Cancer ResearchHebrew University-Hadassah Medical SchoolJerusalemIsrael

Personalised recommendations