Synthesis of 7α-hydroxy derivatives of regulatory oxysterols

Steroids

Volumn 65, Issue 9, 2000, Pages 529-535

  Li, Dansu ^a   Spencer, Thomas A ^a  

^a Dartmouth College   (United States)

Author keywords

7 Hydroxyoxysterols; Oxysterols; Synthesis

Indexed keywords

25 EPOXYCHOLESTEROL; 25 HYDROXYCHOLESTEROL; 26 HYDROXYCHOLESTEROL; 7ALPHA HYDROXYOXYSTEROL DERIVATIVE; CHOLESTEROL DERIVATIVE; OXYSTEROL; UNCLASSIFIED DRUG; 24 HYDROXYCHOLESTEROL; 24,25 EPOXYCHOLESTEROL; 24,25-EPOXYCHOLESTEROL; 24-HYDROXYCHOLESTEROL; 25-HYDROXYCHOLESTEROL; 27-HYDROXYCHOLESTEROL; BILE ACID; CHOLEST 5 EN 3 BETA,7 ALPHA DIOL; CHOLEST-5-EN-3 BETA,7 ALPHA-DIOL; CHOLESTEROL; CHOLESTEROL 7ALPHA MONOOXYGENASE; DRUG DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; BIOSYNTHESIS; CHEMISTRY; DRUG EFFECT; HUMAN; STEREOISOMERISM;

BILE ACIDS AND SALTS; CHOLESTEROL; CHOLESTEROL 7-ALPHA-HYDROXYLASE; HUMANS; HYDROXYCHOLESTEROLS; STEREOISOMERISM;

EID: 0033624333     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(00)00131-8     Document Type: Article

References (32)

1. Janowski B.A., Willy P.J., Devi T.R., Falck J.R., Mangelsdorf D.J. An oxysterol signalling pathway mediated by the nuclear receptor LXRα Nature. 383:1996;728-731.
2. Lehmann J.M., Kliewer S.A., Moore L.B., Smith-Oliver T.A., Oliver B.B., Su J.-L., Sundseth S.S., Winegar D.A., Blanchard D.E., Spencer T.A., Willson T.M. Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. J Biol Chem. 272:1997;3137-3140.
3. Janowski B.A., Grogan M.J., Jones S.A., Wisely G.B., Kliewer S.A., Corey E.J., Mangelsdorf D.J. Structural requirements of ligands for the oxysterol liver X receptors LXRα and LXRβ Proc Natl Acad Sci USA. 96:1999;266-271.
4. Axelson M., Shoda J., Sjövall J., Toll A., Wikvall K. Cholesterol is converted to 7α-hydroxy-3-oxo-4-cholestenoic acid in liver mitochondria. J Biol Chem. 267:1992;1701-1704.
5. Dueland S., Nenseter M.S., MacPhee A.A., Davis R.A., Trawick J.D. Expression of 7α-hydroxylase in non-hepatic cells results in liver phenotypic resistance of the low density lipoprotein receptor to cholesterol repression. J Biol Chem. 267:1992;22695-22698.
6. Martin K.O., Reiss A.B., Lathe R., Javitt N.B. 7α-Hydroxylation of 27-hydroxycholesterol biological role in the regulation of cholesterol synthesis . J Lipid Res. 38:1997;1053-1058.
7. Zhang J., Dricu A., Sjövall J. Studies on the relationships between 7α-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase. Biochim Biophys Acta. 1344:1997;241-249.
8. Kandutsch A.A., Chen H.W. Inhibition of sterol synthesis in cultured mouse cells by cholesterol derivatives oxygenated in the side chain. J Biol Chem. 249:1974;6057-6061.
9. Taylor F.R., Saucier S.E., Shown E.P., Parish E.J., Kandutsch A.A. Correlation between oxysterol binding to a cytosolic binding protein and potency in the repression of hydroxymethylglutaryl coenzyme A reductase. J Biol Chem. 259:1984;12382-12387.
10. Johnson K.A., Morrow C.J., Knight G.D., Scallen T.J. In vivo formation of 25-hydroxycholesterol from endogenous cholesterol after a single meal, dietary cholesterol challenge. J Lipid Res. 35:1994;2241-2253.
11. Lala D.S., Syka P.M., Lazarchik S.B., Mangelsdorf D.J., Parker K.L., Heyman R.A. Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols. Proc Natl Acad Sci USA. 94:1997;4895-4900.
12. Saucier S.E., Kandutsch A.A., Gayen A.K., Swahn D.K., Spencer T.A. Oxysterol regulators of 3-hydroxy-3-methylglutaryl-coA reductase in liver. Effect of dietary cholesterol. J Biol Chem. 264:1989;6863-6869.
13. Esterman A.L., Baum H., Javitt N.B., Darlington G.J. 26-Hydroxycholesterol regulation of hydroxymethylglutaryl-coA reductase activity in Chinese hamster ovary cell culture . J Lipid Res. 24:1983;1304-1309.
14. Andersson S., Davis D.L., Dahlbäck H., Jörnvall H., Russell D.W. Cloning, structure, and expression of the mitochondrial cytochrome P-450 sterol 26-hydroxylase, a bile acid biosynthesis enzyme. J Biol Chem. 264:1989;8222-8229.
15. Rennert H., Fischer R.T., Alvarez J.G., Trzaskos J.M., Strauss J.F. III. Generation of regulatory oxysterols 26-hydroxylation of cholesterol by ovarian mitochondria . Endocrinology. 127:1990;738-746.
16. Lund E., Breuer O., Bjorkhem I. Evidence that 24- and 27-hydroxylation are not involved in the cholesterol-induced down-regulation of hydroxymethylglutaryl-CoA reductase in mouse liver. J Biol Chem. 267:1992;25092-25097.
17. Erickson S.K., Lear S.R., Gayen A.K., Spencer T.A. Oxysterol regulation of cholesterol metabolism. Circulation. 90:1994;420.
18. Spencer T.A. The squalene dioxide pathway of steroid biosynthesis. Acc Chem Res. 27:1994;83-90.
19. Nagano H., Poyser J.P., Cheng K.-P., Luu B., Ourisson G., Beck J.P.L. Chimie et biochimie de drogues chinoises II-stérols hydroxylés cytotoxiques sur des cellules cancéreuses. Synthèse et activité biologique. J Chem Res(m). 9:1977;2522-2571.
20. 27-intermediates in bile acid biosynthesis and their deuterium-labeled analogs. Steroids. 58:1993;119-125.
21. Corey E.J., Grogan M.J. Stereocontrolled syntheses of 24(S),25-epoxycholesterol and related oxysterols for studies on the activation of LXR receptors. Tetrahedron Lett. 39:1998;9351-9354.
22. Kim H.-S., Wilson W.K., Needleman D.H., Pinkerton F.D., Wilson D.K., Quiocho F.A., Schroepfer G.J. Jr. Inhibitors of sterol synthesis. Chemical synthesis, structure, and biological activities of (25R)-3β,26-dihydroxy-5α-cholest-8(14)-en-15-one, a metabolite of 3β-hydroxy-5α-cholest-8(14)-en-15-one. J Lipid Res. 30:1989;247-261.
23. Beckwith A.L.J. Hydroxylation of 5α,6β-dibromocholestan-3β-yl acetate by chromic acid. J Chem Soc. 1961;3162-3164.
24. 5-steroids with pyridinium chlorochromate (PCC) and pyridinium dichromate (PDC). Synth Commun. 17:1987;1227-1233.
25. Kumar V., Amann A., Ourisson G., Luu B. Stereospecific synthesis of 7β- and 7α-hydroxycholesterols. Synth Commun. 17:1987;1279-1286.
26. Blair I.A., Phillipou G., Seaborn C. Synthesis of C-7-2H2 steroids for human metabolism studies. J Labelled Compd Radiopharm. 15:1978;645-655.
27. 3. Biochem Biophys Res Commun. 62:1975;485-491.
28. Koizumi N., Fujimoto Y., Takeshita T., Ikekawa N. Carbon-13 nuclear magnetic resonance of 24-substituted steroids. Chem Pharm Bull. 27:1979;38-42.
29. Ratcliffe R., Rodehorst R. Improved procedure for oxidation with the chromium-trioxide-pyridine complex. J Org Chem. 35:1970;4000-4002.
30. Tomkinson N.C.O., Willson T.M., Russel J.S., Spencer T.A. Efficient, stereoselective synthesis of 24(S),25-epoxycholesterol. J Org Chem. 63:1998;9919-9923.
31. 13C nuclear magnetic resonance spectroscopy. J Lipid Res. 30:1989;133-138.
32. 5-steroids by t-butyl hydroperoxide. Tetrahedron Lett. 38:1997;119-122.