Positron emission tomography radiopharmaceuticals for sex steroid hormone receptor imaging

Current Medicinal Chemistry

Volumn 19, Issue 20, 2012, Pages 3266-3270

  Kiyono, Y ^a   Mori, T ^a   Okazawa, H ^a  

^a UNIVERSITY OF FUKUI   (Japan)

Author keywords

Androgen receptor; Estrogen receptor; Positron emisson tomography; Progesterone receptor; Radiopharmaceuticals

Indexed keywords

16BETA FLUORO 5ALPHA DIHYDROTESTOSTERONE F 18; 5 FLUORO 2,3 BIS(4 HYDROXYPHENYL)PENTANENITRILE F 18; ANDROGEN RECEPTOR; ESTROGEN RECEPTOR; FLUORO 16ALPHA ETHYL 19 NORPROGESTERONE F 18; FLUORO FURANYL 19 NORPROGESTERONE F 18; PROGESTERONE RECEPTOR; RADIOPHARMACEUTICAL AGENT; STEROID RECEPTOR; UNCLASSIFIED DRUG;

CANCER DIAGNOSIS; DRUG STRUCTURE; HUMAN; MOLECULAR IMAGING; NONHUMAN; PHENOTYPE; POSITRON EMISSION TOMOGRAPHY; PROTEIN EXPRESSION; REVIEW; TUMOR DIAGNOSIS;

ANIMALS; GONADAL STEROID HORMONES; HUMANS; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTORS, STEROID;

EID: 84863769724     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712801215919     Document Type: Review

References (49)

1. 18F-labeled positron emission tomographic radiopharmaceuticals in oncology: an overview of radiochemistry and mechanisms of tumor localization. Semin Nucl Med, 2007, 37, (6), 400-419.
2. Mankoff, D.A.; Link, J.M.; Linden, H.M.; Sundararajan, L.; Krohn, K.A., Tumor receptor imaging. J Nucl Med, 2008, 49 Suppl 2, 149S-163S.
3. Osborne, C.K.; Yochmowitz, M.G.; Knight, W.A., 3rd; McGuire, W.L., The value of estrogen and progesterone receptors in the treatment of breast cancer. Cancer, 1980, 46, (12 Suppl), 2884-2888.
4. Krohn, K.A., The physical chemistry of ligand-receptor binding identifies some limitations to the analysis of receptor images. Nucl Med Biol, 2001, 28, (5), 477-483.
5. Krohn, K.A.; Link, J.M., Interpreting enzyme and receptor kinetics: keeping it simple, but not too simple. Nucl Med Biol, 2003, 30, (8), 819-826.
6. Katzenellenbogen, J.A.; Welch, M.J.; Dehdashti, F., The development of estrogen and progestin radiopharmaceuticals for imaging breast cancer Anticancer Res, 1997, 17, (3B), 1573-1576.
7. Melmed, S.; Polonsky, K.S.; Larsen, P.R.; Kronenberg, H.M. Williams Textbook of Endocrinology. Elsevier, 2011.
8. Deroo, B.J.; Korach, K.S., Estrogen receptors and human disease. J Clin Invest, 2006, 116, (3), 561-570.
9. Nilsson, S.; Koehler, K.F.; Gustafsson, J.A., Development of subtype-selective oestrogen receptor-based therapeutics. Nat Rev Drug Discov, 2011, 10, (10), 778-792.
10. 18F]fluoro-17ß-estradiol. J Med Chem, 2005, 48, (20), 6366-6378.
11. Vollenweider-Zerargui, L.; Barrelet, L.; Wong, Y.; Lemarchand-Beraud, T.; Gomez, F., The predictive value of estrogen and progesterone receptors' concentrations on the clinical behavior of breast cancer in women. Clinical correlation on 547 patients. Cancer, 1986, 57, (6), 1171-1180.
12. Kiesewetter, D.O.; Kilbourn, M.R.; Landvatter, S.W.; Heiman, D.F.; Katzenellenbogen, J.A.; Welch, M.J., Preparation of four fluorine-18-labeled estrogens and their selective uptakes in target tissues of immature rats. J Nucl Med, 1984, 25, (11), 1212-1221.
13. Brodack, J.W.; Kilbourn, M.R.; Welch, M.J., Automated production of several positron-emitting radiopharmaceuticals using a single laboratory robot. Int J Rad Appl Instrum A, 1988, 39, (7), 689-698.
14. Brodack, J.W.; Kilbourn, M.R.; Welch, M.J.; Katzenellenbogen, J.A., Application of robotics to radiopharmaceutical preparation: controlled synthesis of fluorine-18 16a-fluoroestradiol-17ß. J Nucl Med, 1986, 27, (5), 714-721.
15. 18F]fluoroestradiol-17ß: the effect of reaction vessel on fluorine-18 resolubilization, product yield, and effective specific activity. Int J Rad Appl Instrum A, 1986, 37, (3), 217-221.
16. Lim, J.L.; Zheng, L.; Berridge, M.S.; Tewson, T.J., The use of 3-methoxymethyl-16ß, 17ß-epiestriol-O-cyclic sulfone as the precursor in the synthesis of F-18 16a-fluoroestradiol. Nucl Med Biol, 1996, 23, (7), 911-915.
17. 18F]fluorodeoxyglucose synthesizer. Nucl Med Biol, 2006, 33, (2), 281-286.
18. 18F]FDG module with a disposable cassette system. Appl Radiat Isot, 2007, 65, (6), 676-681.
19. 18F]fluoroestradiol for breast cancer imaging. Nucl Med Biol, 1999, 26, (4), 473-479.
20. 18F]-fluoroestradiol (FES) with sex steroid binding protein (SBP). Nucl Med Biol, 1999, 26, (8), 905-913.
21. Mankoff, D.A.; Tewson, T.J.; Eary, J.F., Analysis of blood clearance and labeled metabolites for the estrogen receptor tracer [F-18]-16 a-fluoroestradiol (FES). Nucl Med Biol, 1997, 24, (4), 341-348.
22. Moresco, RM.; Scheithauer, B.W.; Lucignani, G.; Lombardi, D.; Rocca, A.; Losa, M.; Casati, R.; Giovanelli, M.; Fazio, F., Oestrogen receptors in meningiomas: a correlative PET and immunohistochemical study. Nucl Med Commun, 1997, 18, (7), 606-615.
23. Dehdashti, F.; Flanagan, F.L.; Mortimer, J.E.; Katzenellenbogen, J.A.; Welch, M.J.; Siegel, B.A., Positron emission tomographic assessment of "metabolic flare" to predict response of metastatic breast cancer to antiestrogen therapy. Eur J Nucl Med, 1999, 26, (1), 51-56.
24. Dehdashti, F.; Mortimer, J.E.; Siegel, B.A.; Griffeth, L.K.; Bonasera, T.J.; Fusselman, M.J.; Detert, D.D.; Cutler, P.D.; Katzenellenbogen, J.A.; Welch, M.J., Positron tomographic assessment of estrogen receptors in breast cancer: comparison with FDG-PET and in vitro receptor assays. J Nucl Med, 1995, 36, (10), 1766-1774.
25. Linden, H.M.; Stekhova, S.A.; Link, J.M.; Gralow, J.R; Livingston, R.B.; Ellis, G.K.; Petra, P.H.; Peterson, L.M.; Schubert, E.K.; Dunnwald, L.K.; Krohn, K.A.; Mankoff, D.A., Quantitative fluoroestradiol positron emission tomography imaging predicts response to endocrine treatment in breast cancer. J Clin Oncol, 2006, 24, (18), 2793-2799.
26. 18F]fluoro-17ß-estradiol uptake in metastatic breast carcinoma. J Nucl Med, 1991, 32, (8), 1526-1531.
27. Mintun, M.A.; Welch, M.J.; Siegel, B.A.; Mathias, C.J.; Brodack, J.W.; McGuire, A.H.; Katzenellenbogen, J.A., Breast cancer: PET imaging of estrogen receptors. Radiology, 1988, 169, (1), 45-48.
28. Mortimer, J.E.; Dehdashti, F.; Siegel, B.A; Trinkaus, K.; Katzenellenbogen, J.A.; Welch, M.J., Metabolic flare: indicator of hormone responsiveness in advanced breast cancer. J Clin Oncol, 2001, 19, (11), 2797-2803.
29. 18F]fluoro-17ß- oestradiol PET. Eur J Nucl Med Mol Imaging, 2011, 38, (1), 37-45.
30. 18F-FDG PET. J Nucl Med, 2009, 50, (10), 1598-1604.
31. 18F fluorodeoxyglucose PET-initial experience. Radiology, 2008, 248, (2), 599-605.
32. 18F]fluorodeoxyglucose PET. Eur J Nucl Med Mol Imaging, 2011, 38, (10), 1824-1831.
33. Yoshida, Y; Kurokawa, T.; Sawamura, Y; Shinagawa, A.; Okazawa, H.; Fujibayashi, Y; Kotsuji, F., The positron emission tomography with F18 17ß-estradiol has the potential to benefit diagnosis and treatment of endometrial cancer. Gynecol Oncol, 2007, 104, (3), 764-766.
34. 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, 1993, 36, (11), 1619-1629.
35. 18F]fluoromoxestrol: a potent, metabolically stable positron emission tomography imaging agent for estrogen receptor positive human breast tumors. Life Sci, 1993, 53, (10), 811-819.
36. Pomper, M.G.; VanBrocklin, H.; Thieme, A.M.; Thomas, R.D.; Kiesewetter, D.O.; Carlson, K.E.; Mathias, C.J.; Welch, M.J.; Katzenellenbogen, J.A., 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, 1990, 33, (12), 3143-3155.
37. 18F]fluoromoxestrol in isolated hepatocytes. Nucl Med Biol, 1999, 26, (1), 123-130.
38. Thomas, C; Gustafsson, J.A., The different roles of ER subtypes in cancer biology and therapy. Nat Rev Cancer, 2011, 11, (8), 597-608.
39. Li, J.; Al-Azzawi, F., Mechanism of androgen receptor action. Maturitas, 2009, 63, (2), 142-148.
40. Mohler, J.L., A role for the androgen-receptor in clinically localized and advanced prostate cancer. Best Pract Res Clin Endocrinol Metab, 2008, 22, (2), 357-372.
41. Dunphy, M.P.; Lewis, J.S., Radiopharmaceuticals in preclinical and clinical development for monitoring of therapy with PET. J Nucl Med, 2009, 50 Suppl 1, 106S-121S.
42. Liu, A.; Dence, C.S.; Welch, M.J.; Katzenellenbogen, J.A., Fluorine-18-labeled androgens: radiochemical synthesis and tissue distribution studies on six fluorine-substituted androgens, potential imaging agents for prostatic cancer. J Nucl Med, 1992, 33, (5), 724-734.
43. 18F-fluoro-5a-dihydrotestosterone versus 18F-FDG in patients with progressive, metastatic prostate cancer. J Nucl Med, 2004, 45, (3), 366-373.
44. Dehdashti, F.; Picus, J.; Michalski, J.M.; Dence, CS.; Siegel, B.A.; Katzenellenbogen, J.A.; Welch, M.J., Positron tomographic assessment of androgen receptors in prostatic carcinoma. Eur J Nucl Med Mol Imaging, 2005, 32, (3), 344-350.
45. Scarpin, K.M.; Graham, J.D.; Mote, P.A.; Clarke, C.L., Progesterone action in human tissues: regulation by progesterone receptor (PR) isoform expression, nuclear positioning and coregulator expression. Nucl Recept Signal, 2009, 7, e009.
46. Conneely, O.M.; Lydon, J.P.; De Mayo, F.; O'Malley, B.W., Reproductive functions of the progesterone receptor. J Soc Gynecol Investig, 2000, 7, (1 Suppl), S25-32.
47. Giersig, C, Progestin and breast cancer. The missing pieces of a puzzle. Bundesgesundheitsblatt Gesundheitsforschung Gesundheitsschutz, 2008, 51, (7), 782-786.
48. 18F]fluoro-16a-ethyl-19-norprogesterone: synthesis and target tissue selective uptake of a progestin receptor based radiotracer for positron emission tomography. J Med Chem, 1988, 31, (7), 1360-1363.
49. Buckman, B.O.; Bonasera, T.A.; Kirschbaum, K.S.; Welch, M.J.; Katzenellenbogen, J.A., Fluorine-18-labeled progestin 16a, 17a-dioxolanes: development of high-affinity ligands for the progesterone receptor with high in vivo target site selectivity. J Med Chem, 1995, 38, (2), 328-337.