Synthesis and biodistribution of fluorine-18-labeled fluorocyclofenils for imaging the estrogen receptor

Nuclear Medicine and Biology

Volumn 34, Issue 4, 2007, Pages 383-390

  Seo, Jai Woong ^a   Chi, Dae Yoon ^a   Dence, Carmen S ^b   Welch, Michael J ^b   Katzenellenbogen, John A ^c  

^a Inha University   (South Korea)

^b WASHINGTON UNIVERSITY SCHOOL OF MEDICINE   (United States)

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

Author keywords

Cyclofenil; Estrogen receptor; Estrogen receptor imaging; Fluorine 18

Indexed keywords

3 (2 FLUOROETHYL)[BIS(4 HYDROXYPHENYL)METHYLENE]CYCLOHEXANE F 18; 4 FLUORO[BIS(4 HYDROXYPHENYL)METHYLENE]CYCLOHEXANE F 18; CYCLOFENIL; ESTROGEN RECEPTOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BREAST CANCER; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DRUG DISTRIBUTION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; IN VIVO STUDY; ISOTOPE LABELING; LIGAND BINDING; NONHUMAN; RADIOCHEMISTRY; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION;

ANIMALS; CYCLOFENIL; ESTROGEN RECEPTOR ALPHA; ESTROGEN RECEPTOR BETA; FEMALE; FLUORINE RADIOISOTOPES; INDICATORS AND REAGENTS; ISOTOPE LABELING; MESYLATES; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, ESTROGEN; TISSUE DISTRIBUTION;

EID: 34248149419     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2007.01.010     Document Type: Article

References (44)

1. Katzenellenbogen J.A. Drugs Pharmaceut Sci 55 (1992) 297-331
2. Katzenellenbogen J.A. Designing steroid receptor-based radiotracers to image breast and prostate tumors. J Nucl Med 36 (1995) 8S-13S
3. Van de Wiele C., De Vos F., Slegers G., Van Belle S., and Dierckx R.A. Radiolabeled estradiol derivatives to predict response to hormonal treatment in breast cancer: a review. Eur J Nucl Med 27 (2000) 1421-1433
4. Andersonm R.E., and Holt J.A. Binding of radiolabeled estrogens by human cells in vitro: implications to the development of a new diagnostic and therapeutic modality in the treatment of malignancies with estrogen receptors. Gynecol Oncol 34 (1989) 80-83
5. De Hertogh R., Ekka E., Vanderheyden I., and Hoet J.J. In vivo observations on reversible binding of estradiol-17β,6,7-3H in rat uterus. Measurement of a biological exchange constant and of the tissue capacity. Endocrinology 88 (1971) 165-174
6. Mintun M.A., Welch M.J., Siegel B.A., Mathias C.J., Brodack J.W., McGuire A.H., et al. Breast cancer: PET imaging of estrogen receptors. Radiology 169 (1988) 45-48
7. Katzenellenbogen J.A., Senderoff S.G., McElvany K.D., O'Brien Jr. H.A., and Welch M.J. 16a-[Bromine-77]bromoestradiol-17β: a high specific-activity, gamma-emitting tracer with uptake in rat uterus and induced mammary tumors. J Nucl Med 22 (1981) 42-47
8. 77Br]Bromoestradiol: dosimetry and preliminary clinical studies. J Nucl Med 23 (1982) 425-430
9. 123I]iodo-11β-nitrαto-19-norpregna-1,3,5(10),20-tetraene-3,17-diol (E-[123I]NIVE). Nucl Med Biol 25 (1998) 411-421
10. Pomper M.G., Van Brocklin H., Thieme A.M., Thomas R.D., Kiesewetter D.O., Carlson K.E., et al. 11 beta-Methoxy-, 11 beta-ethyl- and 17 alpha-ethynyl-substituted 16 alpha-fluoroestradiols: receptor-based imaging agents with enhanced uptake efficiency and selectivity. J Med Chem 33 (1990) 3143-3155
11. Seimbille Y., Benard F., and van Lier J.E. Synthesis of 16α-fluoro ICI 182,780 derivatives: powerful antiestrogens to image estrogen receptor densities in breast cancer by position emission tomography. J Chem Soc Perkin Trans 20 (2002) 2275-2281
12. 18F]Fluoro)estrogens: systematic investigation of a new series of fluorine-18-labeled estrogens as potential imaging agents for estrogen-receptor-positive breast tumors. J Med Chem 36 (1993) 1619-1629
13. Bergmann K.E., Landvatter S.W., Rocque P.G., Carlson K.E., Welch M.J., and Katzenellenbogen J.A. Oxohexestrol derivatives labeled with fluorine-18. Synthesis, receptor binding and in vivo distribution of two non-steroidal estrogens as potential breast tumor imaging agents. Nucl Med Biol 21 (1994) 25-39
14. Lashley M.R., Niedzinski E.J., Rogers J.M., Denison M.S., and Nantz M.H. Synthesis and estrogen receptor affinity of a 4-hydroxytamoxifen-labeled ligand for diagnostic imaging. Bioorg Med Chem 10 (2002) 4075-4082
15. Lee K.C., Moon B.S., Lee J.H., Chung K.H., Katzenellenbogen J.A., and Chi D.Y. Synthesis and binding affinities of fluoroalkylated raloxifenes. Bioorg Med Chem 11 (2003) 3649-3658
16. Yang D.J., Li C., Kuang L.R., Price J.E., Buzdar A.U., Tansey W., et al. Imaging, biodistribution and therapy potential of halogenated tamoxifen analogues. Life Sci 55 (1994) 53-67
17. McDonnell D.P., Connor C.E., Wijayaratne A., Chang C.Y., and Norris J.D. Definition of the molecular and cellular mechanisms underlying the tissue-selective agonist/antagonist activities of selective estrogen receptor modulators. Recent Prog Horm Res 57 (2002) 295-316
18. Silfen S.L., Ciaccia A.V., and Bryant H.U. Selective estrogen receptor modulators: tissue selectivity and differential uterine effects. Climacteric 2 (1999) 268-283
19. Kuiper G.G., Carlsson B., Grandien K., Enmark E., Haggblad J., Nilsson S., et al. Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta. Endocrinology 138 (1997) 863-870
20. Pettersson K., and Gustafsson J.A. Role of estrogen receptor beta in estrogen action. Annu Rev Physiol 63 (2001) 165-192
21. Stauffer S.R., Coletta C.J., Tedesco R., Nishiguchi G., Carlson K., Sun J., et al. Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists. J Med Chem 43 (2000) 4934-4947
22. Mortensen D.S., Rodriguez A.L., Carlson K.E., Sun J., Katzenellenbogen B.S., and Katzenellenbogen J.A. Synthesis and biological evaluation of a novel series of furans: ligands selective for estrogen receptor alpha. J Med Chem 44 (2001) 3838-3848
23. Meyers M.J., Sun J., Carlson K.E., Marriner G.A., Katzenellenbogen B.S., and Katzenellenbogen J.A. Estrogen receptor-beta potency-selective ligands: structure-activity relationship studies of diarylpropionitriles and their acetylene and polar analogues. J Med Chem 44 (2001) 4230-4251
24. Meyers M.J., Sun J., Carlson K.E., Katzenellenbogen B.S., and Katzenellenbogen J.A. Estrogen receptor subtype-selective ligands: asymmetric synthesis and biological evaluation of cis- and trans-5,11-dialkyl-5,6,11,12-tetrahydrochrysenes. J Med Chem 42 (1999) 2456-2468
25. Muthyala R.S., Sheng S., Carlson K.E., Katzenellenbogen B.S., and Katzenellenbogen J.A. Bridged bicyclic cores containing a 1,1-diarylethylene motif are high-affinity subtype-selective ligands for the estrogen receptor. J Med Chem 46 (2003) 1589-1602
26. 18F]propyl pyrazole triol. Nucl Med Biol 30 (2003) 397-404
27. 18F]fluoro-17beta-estradiol. J Med Chem 48 (2005) 6366-6378
28. Lindberg M.K., Moverare S., Skrtic S., Gao H., Dahlman-Wright K., Gustafsson J.A., et al. Estrogen receptor (ER)-beta reduces ERalpha-regulated gene transcription, supporting a "ying yang" relationship between ERalpha and ERbeta in mice. Mol Endocrinol 17 (2003) 203-208
29. Carlson K.E., Choi I., Gee A., Katzenellenbogen B.S., and Katzenellenbogen J.A. Altered ligand binding properties and enhanced stability of a constitutively active estrogen receptor: evidence that an open pocket conformation is required for ligand interaction. Biochemistry 36 (1997) 14897-14905
30. Acharya U., Irvine D.S., Hamilton M.P., and Templeton A.A. The effect of three anti-oestrogen drugs on cervical mucus quality and in-vitro sperm-cervical mucus interaction in ovulatory women. Hum Reprod 8 (1993) 437-441
31. Garg S., Bindal R.D., Durani S., and Kapil R.S. Structure-activity relationship of estrogens: a study involving cyclofenyl as the model compound. J Steroid Biochem 18 (1983) 89-95
32. Tojo S., Hayashi K., and Osawa E. Stimulation of ovulation with F-6066 cyclofenil: bis-(p-acetoxyphenyl)-cyclohexylidenemethane. Acta Obstet Gynecol Scand 52 (1973) 335-3343
33. Seo J.W., Comninos J.S., Chi D.Y., Kim D.W., Carlson K.E., and Katzenellenbogen J.A. Fluorine-substituted cyclofenil derivatives as estrogen receptor ligands: synthesis and structure-affinity relationship study of potential positron emission tomography agents for imaging estrogen receptors in breast cancer. J Med Chem 49 (2006) 2496-2511
34. Pangborn A.B., Giardello M.A., Grubbs R.H., Rosen R.K., and Timmers F.J. Safe and convenient procedure for solvent purification. Organometallics 15 (1996) 1518-1520
35. 18F]fluoride production. Int J Appl Radiat Isot 36 (1985) 327-328
36. 77Br]-bromoestradiol-17 beta and 16 alpha-[77Br]-11 beta-methoxyestradiol-17 beta, two estrogen receptor-binding radiopharmaceuticals. Int J Appl Radiat Isot 33 (1982) 545-551
37. Sharp T.L., Dence C.S., Engelbach J.A., Herrero P., Gropler R.J., and Welch M.J. Techniques necessary for multiple tracer quantitative small-animal imaging studies. Nucl Med Biol 32 (2005) 875-884
38. 18F]fluoroestradiol by target tissues in the rat: competition by tamoxifen, and implications for quantitating estrogen receptors in vivo and the use of animal models in receptor-binding radiopharmaceutical development. Nucl Med Biol 20 (1993) 735-745
39. 77Br]bromonorhexestrol), two gamma-emitting estrogens that show receptor-mediated uptake by target tissues in vivo. J Med Chem 25 (1982) 1307-1312
40. Bonasera T.A., O'Neil J.P., Xu M., Dobkin J.A., Cutler P.D., Lich L.L., et al. Preclinical evaluation of fluorine-18-labeled androgen receptor ligands in baboons. J Nucl Med 37 (1996) 1009-1015
41. Fortunati N. Sex hormone-binding globulin: not only a transport protein. What news is around the corner?. J Endocrinol Invest 22 (1999) 223-234
42. Hammes A., Andreassen T.K., Spoelgen R., Raila J., Hubner N., Schulz H., et al. Role of endocytosis in cellular uptake of sex steroids. Cell 122 (2005) 751-762
43. Porto C.S., Lazari M.F., Abreu L.C., Bardin C.W., and Gunsalus G.L. Receptors for androgen-binding proteins: internalization and intracellular signalling. J Steroid Biochem Mol Biol 53 (1995) 561-565
44. DeSombre E.R., Mease R.C., Hughes A., Harper P.V., DeJesus O.T., and Friedman A.M. Bromine-80m-labeled estrogens: Auger electron-emitting, estrogen receptor-directed ligands with potential for therapy of estrogen receptor-positive cancers. Cancer Res 48 (1988) 899-906