An efficient stereoselective synthesis of 6-α-aminoestradiol: Preparation of estradiol fluorescent probes

Steroids

Volumn 62, Issue 6, 1997, Pages 462-467

  Adamczyk, Maciej ^a   Mattingly, Phillip G ^a   Reddy, Rajarathnam E ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

estradiol; 6 Aminoestradiol; Fluorescent probe for estrogen binding protein

Indexed keywords

6ALPHA AMINOESTRADIOL; ESTRADIOL; UNCLASSIFIED DRUG;

ARTICLE; ESTROGEN BINDING; HYDROLYSIS; NUCLEAR MAGNETIC RESONANCE; PROTEIN BINDING; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

CRYSTALLOGRAPHY, X-RAY; ESTRADIOL; FLUORESCENT DYES; MODELS, CHEMICAL; MODELS, MOLECULAR; SPECTROPHOTOMETRY, INFRARED; STEREOISOMERISM;

EID: 0030955927     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00015-9     Document Type: Article

References (26)

1. 5-steroids in the ZR-75-1 human breast cancer cell line. Cancer Res 46:4933-4937.
2. Edwards DP, Chamness GC, McGuire WL (1979). Estrogen and progesterone receptor proteins in breast cancer. Biochem Biophys Acta 560:457-486.
3. Jaouen G, Vessieres A, Butler IS (1993). Bioorganometallic chemistry: A future direction for transition metal organometallic chemistry? Accounts Chem Res 26:361-369.
4. Lippman ME, Allegra JC (1978). Estrogen receptors and endocrine therapy of breast cancer. N Engl J Med 299:930-933.
5. Chan DW, Perlstein MT (1987). Immunoassay. A Practical Guide. Academic Press, New York.
6. Alberton BD, Haseltine FP (1988). Non-radiometric Assays. Technology and Application in Polypeptide and Steroid Hormone Detection. Allan R. Liss, New York.
7. Gosling JP (1990). A decade of development in immunoassay methodology. Clin Chem 36:1408-1427.
8. Dandliker WB, Hicks AN, Levison SA, Brawn RJ (1977). A fluorescein-labeled derivative of estradiol with binding affinity towards cellular receptors. Biochem Biophys Res Commun 74:538-544.
9. Bodmer DM, Tiefenauer LX, Andres RY (1989). Antigen versus antibody-immobilized ELISA procedures based on a biotinylestradiol conjugate. J Steroid Biochem 33:1161-1166.
10. Tiefenauer LX, Andres RY (1990). Biotinyl-estradiol derivatives in enzyme immunoassays: Structural requirements for optimal antibody binding. J Steroid Biochem 35:633-639.
11. Mares A, DeBoever J, Stans G, Bosmans E, Kohen F (1995). Synthesis of novel biotin-estradiol conjugate and its use for the development of a direct, broad range enzyme immunoassay for plasma estradiol. J Immuno Meth 183:211-219.
12. Luppa P, Birkmayer C, Hauptmann H (1994). Synthesis of 3-hydroxyestra-1,3,5(10)-trien-17-one and 3,17β-dihydroxyestra-1,3,5(10)-triene 6α-N-(∈-biotinyl)caproamide, tracer substances for developing immunoassays for estrone and estradiol. Bioconj Chem 5:167-171.
13. Muhelenbruch B, Kirmeier F, Roth HJ (1986). Syntheses und eigenschaften fluoreszierender Estradiol-derivative. Arch Pharm (Weinheim) 319:196-203.
14. Redeuilh G, Secco C, Baulieu EE (1990). Biotylestradiol for purification of estrogen receptor. Meth Enzymol 184:292-300.
15. French AN, Wilson SR, Welch MJ, Katzenellenbogen JA (1993). A synthesis of 7α-substituted estradiols: Synthesis and biological evaluation of a 7α-pentyl-substituted BODIPY fluorescent conjugate and a fluorine-18-labeled 7α-pentylestradiol analog. Steroids 58:157-169.
16. Barrows GH, Stropupe SB, Riehm JD (1980). Nuclear uptake of a 17-β-estradiol-fluorescein derivatives as a marker of estrogen dependence. Am J Clin Path 73:330-339.
17. Daxenbichler G, Grill HJ, Domanid R, Moser E, Dapunt O (1980). Receptor binding of fluorescein-labeled steroids. J Steroid Biochem 13:489-493.
18. Joyce BG, Nicholson RJ, Morton MS, Griffiths K (1982). Studies with steroid-fluorescein conjugates on estrogen target tissues. Eur J Cancer Clin Oncol 18:1147-1155.
19. Hamcher H, Christ E (1983). Potential antineoplastics. Arzneim Forsch/Drug Res 33:347-352.
20. Tiefenauer LX, Bodmer DM, Frei W, Andres RY (1989). Prevention of bridge binding in immunoassays: A general estradiol tracer structure. J Steroid Biochem 32:251-257.
21. Kocienski PJ (1994). Protecting Groups, Thieme, New York.
22. Green TW, Wuts PGM (1991). Protective Groups in Organic Synthesis. Wiley, New York.
23. White JD, Kawasaki M (1990). Total synthesis of (+)-Latrunculin A. J Am Chem Soc 112:4991-4993.
24. Wintersteiner O, Moore M, Cohen AI (1964). Stereochemical studies on 6,7-substituted derivatives of estra-3,17β-diol. J Org Chem 29:1325-1333.
25. Aadanier J, Cole W (1962). Configurational assignment to C-6 epimeric 3a,5a-cyclosteroid alcohols and amines by means of n.m.r. J Org Chem 27:4610-4615.
26. 13C nuclear magnetic resonance spectroscopic study. J Chem Soc Perkin Trans 11245-250.