Synthesis of ent-25-hydroxycholesterol

Steroids

Volumn 71, Issue 6, 2006, Pages 484-488

  Westover, Emily J ^a   Covey, Douglas F ^a  

^a WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Enantiomer; ent 25 Hydroxycholesterol; Oxysterol

Indexed keywords

25 HYDROXYCHOLESTEROL;

ARTICLE; BINDING SITE; CHIRALITY; CHOLESTEROL SYNTHESIS; ENANTIOMER; LIPID ANALYSIS; MOLECULAR PROBE; PROTEIN BINDING; STRUCTURE ACTIVITY RELATION;

BINDING SITES; CHOLESTEROL; HYDROXYCHOLESTEROLS; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 33646124975     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.steroids.2006.01.007     Document Type: Article

References (11)

1. Brown M.S., and Goldstein J.L. Suppression of 3-hydroxy-3-methylglutaryl coenzyme A reductase activity and inhibition of growth of human fibroblasts by 7-ketocholesterol. J Biol Chem 249 22 (1974) 7306-7314
2. Kandutsch A.A., and Chen H.W. Inhibition of cell growth by oxygenated derivatives of cholesterol. J Biol Chem 249 19 (1974) 6057-6061
3. Johnson K.A., Morrow C.J., Knight G.D., and Scallen T.J. In vivo formation of 25-hydroxycholesterol from endogenous cholesterol after a single meal, dietary cholesterol challenge. J Lipid Res 35 12 (1994) 2241-2253
4. Lund E.G., Kerr T.A., Sakai J., Li W.P., and Russell D.W. cDNA cloning of mouse and human cholesterol 25-hydroxylases, polytopic membrane proteins that synthesize a potent oxysterol regulator of lipid metabolism. J Biol Chem 273 51 (1998) 34316-34327
5. Kandutsch A.A., Chen H.W., and Heiniger H.-J. Biological activity of some oxygenated sterols. Science 201 (1978) 498-501
6. Kauffman J.M., Westerman P.W., Carey M.C., and Goldman M. Fluorocholesterols, in contrast to hydroxycholesterols, exhibit interfacial properties similar to cholesterol. J Lipid Res 41 6 (2000) 991-1003
7. Theunissen J.J., Jackson R.L., Kempen H.J., and Demel R.A. Membrane properties of oxysterols. Interfacial orientation, influence on membrane permeability and redistribution between membranes. Biochim Biophys Acta 860 1 (1986) 66-74
8. Holmes R.P. 25-Hydroxysterols increase the permeability of liposomes to Ca2+ and other cations. Biochim Biophys Acta 792 3 (1984) 371-375
9. Lange Y., Ye J., and Steck T. Activation of membrane cholesterol by displacement from phospholipids. J Biol Chem 280 43 (2005) 36126-36131
10. Westover E.J., and Covey D.F. The enantiomer of cholesterol. J Membr Biol 202 2 (2004) 61-72
11. Westover E.J., and Covey D.F. First synthesis of ent-desmosterol and its conversion to ent-deuterocholesterol. Steroids 68 2 (2003) 159-166