Synthesis of novel arylpyrazolo corticosteroids as potential ligands for imaging brain glucocorticoid receptors

Steroids

Volumn 68, Issue 2, 2003, Pages 177-191

  Wüst, Frank ^a,b   Carlson, Kathryn E ^c   Katzenellenbogen, John A ^c  

^a INSTITUTE OF ION BEAM PHYSICS AND MATERIALS RESEARCH   (Germany)

^b UNIVERSITY OF LEIPZIG   (Germany)

^c UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Arylpyrazolo corticosteroids; Glucocorticoid receptor binding; Positron emission tomography (PET); Radiolabeling

Indexed keywords

2' (4 FLUOROPHENYL) 17ALPHA (1 PROPYN 1 YL) 11BETA,17BETA DIHYDROXYANDROST 4 ENO[3,2 C]PYRAZOLE F 18; 2' (4 FLUOROPHENYL) 17ALPHA (3 FLUORO 1 PROPYN 1 YL) 11BETA,17BETA DIHYDROXYANDROST 4 ENO[3,2 C]PYRAZOLE F 18; 2' (4 FLUOROPHENYL) 21 FLUORO 20 OXO 11BETA,17ALPHA DIHYDROXYPREGN 4 ENO[3,2 C]PYRAZOLE F 18; 2' (4 IODOPHENYL) 17ALPHA (1 PROPYN 1 YL) 11BETA,17BETA DIHYDROXYANDROST 4 ENO[3,2 C]PYRAZOLE I 131; CORTICOSTEROID DERIVATIVE; DEXAMETHASONE; GLUCOCORTICOID RECEPTOR; LIGAND; RADIOPHARMACEUTICAL AGENT; UNCLASSIFIED DRUG;

ARTICLE; BRAIN; CARBON NUCLEAR MAGNETIC RESONANCE; CHROMATOGRAPHY; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; MASS SPECTROMETRY; MELTING POINT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POSITRON; POSITRON EMISSION TOMOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; RADIOMETRY; RAT; RECEPTOR AFFINITY; STEROIDOGENESIS; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY;

EID: 0037330692     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(02)00171-X     Document Type: Article

References (39)

1. De Kloet ER, Sutanto W, editors. Neurobiology of steroids, vol. 22. New York: Academic Press; 1994.
2. Joëls M., Vreugdenhil E. Corticosteroids in the brain. Mol. Neurobiol. 17:1998;87-108.
3. De Kloet E.R., Vreugdenhil E., Oitzl M.S., Joëls M. Brain corticosteroid receptor balance in health and disease. Endocr. Rev. 19:1998;269-301.
4. Korte S.M. Corticosteroids in relation to fear, anxiety and psychopathololgy. Neurosci. Biobehav. Rev. 25:2001;117-142.
5. Reul J.M.H.M., De Kloet E.R. Two receptor systems for corticosterone in rat brain: microdistribution and differential occupation. Endocrinology. 117:1985;2505-2511.
6. Holsboer F. The rational for corticotropin-releasing hormone receptor (CRH-R) antagonists to treat depression and anxiety. Psychiatr. Res. 33:1999;181-214.
7. De Kloet E.R. Brain corticosteroids receptor balance and homeostatic control. Front. Neuroendocrinol. 12:1991;95-164.
8. Pomper M.G., Kochanny M.J., Thieme A.M., Carlson K.E., VanBrocklin H.F., Mathias C.J.et al. Fluorine-substituted corticosteroids: synthesis and evaluation as potential receptor-based imaging agents for positron emission tomography of the brain. Nucl. Med. Biol. 19:1992;461-480.
9. Hoyte R.M., Labaree D.C., Fede J.-M., Harris C., Hochberg R.B. Iodinated and fluotinated steroid 2′-aryl-[3,2-c] pyrazoles as potential glucocorticoid receptor imaging agents. Steroids. 63:1998;595-602.
10. 18F ]RU 52461: in vivo evalution as a brain glucocorticoid receptor radioligand Nucl. Med. Biol. 19:1992;167-173.
11. Feliu A.L., Rottenberg D.A. Synthesis and evaluation of fluorine-18 21-fluoroprednisone as a potential ligand for neuro-PET studies. J. Nucl. Med. 28:1986;998-1005.
12. 18F ]fluoro-Org6141 in the rat: a potential glucocorticoid receptor ligand for positron emission tomography Nucl. Med. Biol. 22:1995;915-920.
13. 18F ] Win 4457 J. Labelled Cpd. Radiopharm. 25:1988;1245-1254.
14. 3H ]Cortivazol: a unique high affinity ligand for the glucocorticoid receptor Endocrinology. 117:1885;1355-1362.
15. Winneker R.C., Russell M.M., Might C.K., Schane H.P. The interaction of nivazol with the glucocorticoid receptor from rat and rhesus monkey target tissues. Steroids. 42:1985;447-457.
16. Still W.C., Kahn M., Mitra A. Rapid chromatographic technique for preparative separations with moderate resolution. J. Org. Chem. 43:1978;2923-2925.
17. Baloniak S., Thiel U., Pacholczyk M. Synthesis of 1-(4-iodophenyl)-3-hydroxypyridazin-6-one derivatives. Acta Pol. Pharm. 33:1976;73-79.
18. Koser G.F., Wettach R.H. [Hydroxy(tosyloxy)iodo]benzene, a versatile reagent for the mild oxidation of aryl iodides at the iodine atom by ligand transfer. J. Org. Chem. 45:1980;1542-1543.
19. Katzenellenbogen J.A., Johnsonm H.J. Jr., Myers H.N. Photoaffinity labels for estrogen binding proteins of rat uterus. Biochemistry. 12:1973;4085-4092.
20. Katzenellenbogen J.A., Johnson H.J. Jr., Carlson K.E., Myers H.N. Photoreactivity of some light-sensitive estrogen derivatives. Use of an exchange assay to determine their photointeraction with the rat uterine estrogen binding protein. Biochemistry. 13:1974;2986-2994.
21. Teutsch G., Costerousse G., Deraedt R., Benzoni J., Fortin M., Philibert D. 17α-Alkynyl-11β,17-dihydroxyandrostane derivatives: a new class of potent gluco-corticoids. Steroids. 38:1981;651-665.
22. Ojasoo T., Doré J.-C., Gilbert J., Raynaud J.-P. Binding of steroids to the progestin and glucocorticoid receptors analyzed by correspondence analysis. Steroids. 31:1988;1160-1169.
23. Wüst F., Spies H., Johannsen B. Synthesis of 17α-substituted mercaptoalkynyl derivatives of 3,17β-estradiol. Tetrahedron Lett. 38:1998;2931-2932.
24. El Amouri H., Vessiéres A., Vichard D., Top S., Gruselle M., Jaouen G. Syntheses and affinities of novel organometallic-labeled estradiol derivatives: a structure-affinity relationship. J. Med. Chem. 35:1992;3130-3135.
25. Wojtowitcz J.A., Polak R. 3-Substituted oxetanes. J. Org. Chem. 38:1973;2061-2066.
26. Ducruix A., Pascard C., David S., Fischer J.-C. Crystal and molecular structure of a carbohydrate-derived oxetan-3-one. Definitive evidence for a novel participation of a pyranose ring oxygen atom. J. Chem. Soc. Perkin Trans. 2:1976;1678-1682.
27. Schroeter S., Orlando C.M. Photocycloaddition of various ketones and aldehydes to vinyl ethers and ketene diethyl acetals. J. Org. Chem. 34:1969;1181-1187.
28. Rowland A.T., Drawbough R.S., Dalton J.R. Steroid oxetanones. Part 3. Synthesis of 5,7-alpha-epoxy-5-alpha-cholestan-6-ones. J. Org. Chem. 42:1977;487-490.
29. Pons M., Simons S.S. Jr. Facile, high-yield synthesis of spiro C-17 steroidal oxetan-3′-ones. J. Org. Chem. 46:1981;3262-3264.
30. Berridge M.S., Tewson T.J. Chemistry of fluorine-18 radiopharmaceuticals. Appl. Radiat. Isot. 37:1986;685-693.
31. Kilbourn RM. Fluorine-18 labeling of radiopharmaceuticals. Nuclear Science Series NAS-NS-32203. Washington DC: National Acadamy Press; 1990.
32. 18F ]fluoride ion with diaryliodonium salts J. Chem. Soc. Perkin Trans. 1:1998;2043-2046.
33. Koser G.F., Wettach R.H., Smith C.S. New methodology in iodonium salt synthesis. Reactions of [hydroxy(tosyloxy)iodo]arenes with aryltrimethylsilanes. J. Org. Chem. 45:1980;1543-1544.
34. Pike V.W., Butt F., Shah A., Wissowson D.A. Facile synthesis of substituted diaryliodonium tosylates by treatment of aryltributylstannanes with Koser's reagent. J. Chem. Soc. Perkin Trans. 1:1999;245-248.
35. Carroll M.A., Pike V.W., Widdowson D.A. New synthesis of diaryliodonium sulfonates from arylboronic acids. Tetrahedron Lett. 41:2000;5393-5396.
36. Peacock M.J., Pletcher D. The electrosynthesis of diaryliodonium salts. Tetrahedron Lett. 41:2000;8995-8998.
37. 18F ]fluoroheptodecanoic acid in high yields via aminopolyether supported nucleophilic fluorination J. Labelled Cpd. Radiopharm. 23:1986;455-467.
38. Wilbur D.S. Radiohalogenations of proteins: an overview of radionuclides. Bioconjugate Chem. 3:1992;433-470.
39. Alvarez Nuñez F.A., Yalkowsky S.H. Correlation between log P and Clog P for some steroids. J. Pharm. Sci. 86:1997;1187-1189.