Radiolabeled 5-iodo-3′-O-(17β-succinyl-5α-androstan-3-one) -2′-deoxyuridine and its 5′-monophosphate for imaging and therapy of androgen receptor-positive cancers: Synthesis and biological evaluation

Journal of Medicinal Chemistry

Volumn 52, Issue 16, 2009, Pages 5124-5143

  Kortylewicz, Zbigniew P ^a   Nearman, Jessica ^a   Baranowska Kortylewicz, Janina ^a  

^a UNIVERSITY OF NEBRASKA MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 IODO 2' DEOXYURIDINE 5' MONOPHOSPHATE I 125; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE I 125; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) 2' DEOXYURIDINE; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) 2' DEOXYURIDINE I 125; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; 5 IODO 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE I 125; 5 IODO 3' O SUCCINYL 2' DEOXYURIDINE ETHYL ESTER; 5 IODO 3' O SUCCINYL 2' DEOXYURIDINE ETHYL ESTER I 125; 5 IODO O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; 5 IODO O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE I 125; 5 TRI N BUTYLSTANNYL 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; 5 TRIMETHYLSTANNYL 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) 2' DEOXYURIDINE; 5 TRIMETHYLSTANNYL 3' O (17BETA SUCCINYL 5ALPHA ANDROSTAN 3 ONE) O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; 5 TRIMETHYLSTANNYL 3' O SUCCINYL 2' DEOXYURIDINE ETHYL ESTER; 5 TRIMETHYLSTANNYL O,O' (DI TERT BUTYL) 2' DEOXYURIDIN 5' YL MONOPHOSPHATE; ANDROGEN RECEPTOR; ANTINEOPLASTIC AGENT; IDOXURIDINE; RADIOLIGAND; SEX HORMONE BINDING GLOBULIN; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CANCER INHIBITION; CANCER RADIOTHERAPY; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DNA SYNTHESIS; DRUG DEGRADATION; DRUG DESIGN; DRUG DISTRIBUTION; DRUG DOSE ESCALATION; DRUG PROTEIN BINDING; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SPECIFICITY; DRUG STABILITY; DRUG SYNTHESIS; DRUG TARGETING; DRUG UPTAKE; FEMALE; HUMAN; HUMAN CELL; ISOTOPE LABELING; LOW DRUG DOSE; MOUSE; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PROTEIN EXPRESSION; SINGLE DRUG DOSE; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY; TECHNIQUE; TUMOR XENOGRAFT;

ANDROSTANOLS; ANIMALS; BLOOD PROTEINS; CELL LINE, TUMOR; CELL SURVIVAL; DEOXYURACIL NUCLEOTIDES; DEOXYURIDINE; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; IODINE RADIOISOTOPES; MICE; MICE, NUDE; NEOPLASM TRANSPLANTATION; NEOPLASMS, HORMONE-DEPENDENT; PROTEIN BINDING; RABBITS; RADIOPHARMACEUTICALS; RECEPTORS, ANDROGEN; SERUM; SEX HORMONE-BINDING GLOBULIN; TRANSPLANTATION, HETEROLOGOUS;

EID: 69049110970     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9005803     Document Type: Article

References (92)

1. Schippinger, W.; Regitnig, P.; Dandachi, N.; Wernecke, K. D.; Bauernhofer, T.; Samonigg, H.; Moinfar, F. Evaluation of the prognostic significance of androgen receptor expression in metastatic breast cancer. Virchows Arch. 2006, 449, 24-30.
2. Agrawal, A. K.; Jeleń, M.; Grzebieniak, Z.; Zukrowski, P.; Rudnicki, J.; Nienartowicz, E. Androgen receptors as a prognostic and predictive factor in breast cancer. Folia Histochem. Cytobiol. 2008, 46, 269-276.
3. Ogawa, Y.; Hai, E.; Matsumoto, K.; Ikeda, K.; Tokunaga, S.; Nagahara, H.; Sakurai, K.; Inoue, T.; Nishiguchi, Y. Androgen receptor expression in breast cancer: relationship with clinicopathological factors and biomarkers. Int. J. Clin. Oncol. 2008, 13, 431-435.
4. Agoff, S. N.; Swanson, P. E.; Linden, H.; Hawes, S. E.; Lawton, T. J. Androgen receptor expression in estrogen receptor-negative breast cancer. Immunohistochemical, clinical, and prognostic associations. Am. J. Clin. Pathol. 2003, 120, 725-731.
5. Culig, Z.; Klocker, H.; Bartsch, G.; Steiner, H.; Hobisch, A. Androgen receptors in prostate cancer. J. Urol. 2003, 170, 1363-1369.
6. Taplin, M. E.; Balk, S. P. Androgen receptor: a key molecule in the progression of prostate cancer to hormone independence. J. Cell. Biochem. 2004, 91, 483-490.
7. Chodak, G. W.; Kranc, D. M.; Puy, L. A.; Takeda, H.; Johnson, K.; Chang, C. Nuclear localization of androgen receptor in heterogeneous samples of normal, hyperplastic and neoplastic human prostate. J. Urol. 1992, 147, 798-803.
8. Donovan, M. J.; Hamann, S.; Clayton, M.; Khan, F. M.; Sapir, M.; Bayer-Zubek, V.; Fernandez, G.; Mesa-Tejada, R.; Teverovskiy, M.; Reuter, V. E.; Scardino, P. T.; Cordon-Cardo, C. Systems pathology approach for the prediction of prostate cancer progression after radical prostatectomy. J. Clin. Oncol. 2008, 26, 3923-3929.
9. Palmberg, C.; Koivisto, P.; Kakkola, L.; Tammela, T. L.; Kallioniemi, O. P.; Visakorpi, T. Androgen receptor gene amplification at primary progression predicts response to combined androgen blockade as second line therapy for advanced prostate cancer. J. Urol. 2000, 164, 1992-1995.
10. Chen, Y.; Sawyers, C. L.; Scher, H. I. Targeting the androgen receptor pathway in prostate cancer. Curr. Opin. Pharmacol. 2008, 8, 440-448.
11. Kominea, A.; Konstantinopoulos, P. A.; Kapranos, N.; Vandoros, G.; Gkermpesi, M.; Andricopoulos, P.; Artelaris, S.; Savva, S.; Varakis, I.; Sotiropoulou-Bonikou, G.; Papavassiliou, A. G. Androgen receptor (AR) expression is an independent unfavorable prognostic factor in gastric cancer. J. Cancer. Res. Clin. Oncol. 2004, 130, 253-258.
12. Kuhnel, R.; de Graaff, J.; Rao, B. R.; Stolk, J. G. Androgen receptor predominance in human ovarian carcinoma. J. Steroid. Biochem. 1987, 26, 393-397.
13. Risch, H. A. Hormonal etiology of epithelial ovarian cancer, with a hypothesis concerning the role of androgens and progesterone. J. Natl. Cancer Inst. 1998, 90, 1774-1786.
14. Scambia, G.; Benedetti Panici, P.; Ferrandina, G.; Battaglia, F.; Baiocchi, G.; Di Stefano, P.; Tinari, N.; Coronetta, F.; Piantelli, M.; Natali, P.; Iacobelli, S.; Mancuso, S. Expression of HER-2/neu oncoprotein, DNA-ploidy and S-phase fraction in advanced ovarian cancer. Int. J. Gynecol. Cancer 1993, 3, 271-278.
15. Chadha, S.; Rao, B. R.; Slotman, B. J.; van Vroonhoven, C. C.; van der Kwast, T. H. An immunohistochemical evaluation of androgen and progesterone receptors in ovarian tumors. Hum. Pathol. 1993, 24, 90-95.
16. Poisson, M.; Pertuiset, B. F.; Hauw, J. J.; Philippon, J.; Buge, A.; Moguilewsky, M.; Philibert, D. Steroid hormone receptors in human meningiomas, gliomas and brain metastases. J. Neurooncol. 1983, 1, 179-189.
17. Boix, L.; Bruix, J.; Castells, A.; Fuster, J.; Bru, C.; Visa, J.; Rivera, F.; Rodes, J. Sex hormone receptors in hepatocellular carcinoma. Is there a rationale for hormonal treatment? J. Hepatol. 1993, 17, 187-191.
18. Beattie, C. W.; Hansen, N. W.; Thomas, P. A. Steroid receptors in human lung cancer. Cancer Res. 1985, 45, 4206-4214.
19. Kaiser, U.; Hofmann, J.; Schilli, M.; Wegmann, B.; Klotz, U.; Wedel, S.; Virmani, A. K.; Wollmer, E.; Branscheid, D.; Gazdar, A. F.; Havemann, K. Steroid-hormone receptors in cell lines and tumor biopsies of human lung cancer. Int. J. Cancer 1996, 67, 357-364.
20. Ito, K.; Suzuki, T.; Akahira, J.; Moriya, T.; Kaneko, C.; Utsunomiya, H.; Yaegashi, N.; Okamura, K.; Sasano, H. Expression of androgen receptor and 5alpha-reductases in the human normal endometrium and its disorders. Int. J. Cancer. 2002, 99, 652-657.
21. Nahleh, Z. Androgen receptor as a target for the treatment of hormone receptor-negative breast cancer: an unchartered territory. Future Oncol. 2008, 4, 15-21.
22. Olsen, C. M.; Green, A. C.; Nagle, C. M.; Jordan, S. J.; Whiteman, D. C.; Bain, C. J.; Webb, P. M. Australian Cancer Study Group (Ovarian Cancer) and the Australian Ovarian Cancer Study Group. Epithelial ovarian cancer: testing the "androgens hypothesis". Endocr.-Relat. Cancer 2008, 15, 1061-1068.
23. Tworoger, S. S.; Lee, I. M.; Buring, J. E.; Hankinson, S. E. Plasma androgen concentrations and risk of incident ovarian cancer. Am. J. Epidemiol. 2008, 167, 211-218.
24. Vassilomanolakis, M.; Koumakis, G.; Barbounis, V.; Hajichristou, H.; Tsousis, S.; Efremidis, A. A phase II study of flutamide in ovarian cancer. Oncology 1997, 54, 199-202.
25. Tumolo, S.; Rao, B. R.; van der Burg, M. E.; Guastalla, J. P.; Renard, J.; Vermorken, J. B. Phase II trial of flutamide in advanced ovarian cancer: an EORTC Gynaecological Cancer Cooperative Group study. Eur. J. Cancer 1994, 30A, 911-914.
26. Risch, H. A. Hormonal etiology of epithelial ovarian cancer, with a hypothesis concerning the role of androgens and progesterone. J. Natl. Cancer Inst. 1998, 90, 1774-1786.
27. Kolfschoten, G. M.; Hulscher, T. M.; Pinedo, H. M.; Boven, E. Drug resistance features and S-phase fraction as possible determinants for drug response in a panel of human ovarian cancer xenografts. Br. J. Cancer. 2000, 83, 921-917.
28. Reles, A. E.; Gee, C.; Schellschmidt, I.; Schmider, A.; Unger, M.; Friedmann, W.; Lichtenegger, W.; Press, M. F. Prognostic significance of DNA content and S-phase fraction in epithelial ovarian carcinomas analyzed by image cytometry. Gynecol. Oncol. 1998, 71, 3-13.
29. Kimball, R. E.; Schlaerth, J. B.; Kute, T. E.; Schlaerth, A. C.; Santoso, J.; Ballon, S. C.; Spirtos, N. M. Flow cytometric analysis of lymph node metastases in advanced ovarian cancer: clinical and biologic significance. Am. J. Obstet. Gynecol. 1997, 176, 1319-1326.
30. Abdel-Wahab, M.; Krishan, A.; Milikowski, C.; Wahab, A. A.; Walker, G.; Markoe, A. Androgen receptor antigen density and S-phase fraction in prostate cancer: a pilot study. Prostate Cancer Prostatic Dis. 2003, 6, 294-300.
31. Koivisto, P. Aneuploidy and rapid cell proliferation in recurrent prostate cancers with androgen receptor gene amplification. Prostate Cancer Prostatic Dis. 1997, 1, 21-25.
32. Samoszuk, M. K.; Sallash, G.; Chen, K.; Carlton, E.; Oldaker, T. Association between flow cytometric S-phase fraction and apoptotic rate in breast cancer. Cytometry 1996, 26, 281-285.
33. Largillier, R.; Namer, M.; Ramaioli, A.; Ferrero, J. M.; Magné, N.; Courdi, A.; Leblanc-Talent, P.; Formento, P.; Ettore, F.; Milano, G. Prognostic value of S-phase fraction in 920 breast cancer patients: focus on T1N0 status. Int. J. Biol. Markers 2003, 18, 273-279.
34. Del Casar, J. M.; Martín, A.; García, C.; Corte, M. D.; Alvarez, A.; Junquera, S.; González, L. O.; Bongera, M.; García-Muñiz, J. L.; Allende, M. T.; Vizoso, F. Characterization of breast cancer subtypes by quantitative assessment of biological parameters: relationship with clinicopathological characteristics, biological features and prognosis. Eur. J. Obstet. Gynecol. Reprod. Biol. 2008, 141, 147-152.
35. Kabalka, G. W.; Varma, R. S. The synthesis of radiolabelled compounds via organometalic intermediates. Tetrahedron 1989, 45, 6601-6621.
36. Pereyre, M.; Quintard, J. P.; Rahm, A. Tin in Organic Synthesis; Butterworth-Heinemann: London, 1987; pp 136-140.
37. Volovelskii, L. N.; Rastrepina, I. A.; Popova, N. V.; Koryukina, V. N.; Kustova, S. P. Acylation of steroidal alcohols by N-succinamic acids. Khim. Prir. Soedin. 1985, 5, 700-704.
38. Van Boom, J.; Burgers, P. Use of levulinic acid in the protection of oligonucleotides via the modified phosphotriester method: synthesis of decarbonucleotide U-A-U-A-U-A-U-A-U-A. Tetrahedron Lett. 1976, 21, 4875-4878.
39. 123I]-1-(β-D-arabinofuranosyl)-5(E)-(2- iodovinyluracil (IVaraU): high yielding radiolabeling via organotin and exchange reactions. Appl. Radiat. Isot. 1994, 45, 795-801.
40. Fraker, P. J.; Speck, J. C. Protein and cell membrane iodinations with a sparingly soluble chloroamide, 1,3,4,6-tetrachloro-3a, 6a-diphenylglycoluril. Biochem. Biophys. Res. Commun. 1978, 80, 849-857.
41. 125I)iodo-1″-propen-3″-yl}-1- imidazolidinyl]-2-trifluoromethylbenzonitrile: a potential radioligand for the androgen receptor. J. Labelled Compd. Radiopharm. 2001, 44, 47-54.
42. 123I]-β-CIT) in nonhuman primates: pharmacokinetics, biodistribution and SPECT brain imaging co-registered with MRI. Nucl. Med. Biol. 1993, 20, 597-606.
43. Baranowska-Kortylewicz, J.; Helseth, L. D.; Lai, J.; Schneiderman, M. H.; Schneiderman, G. S.; Dalrymple, G. V. Radiolabeling kit/ generator for 5-radiohalogenated uridines. J. Labelled Compd. Radiopharm. 1994, 34, 513-521.
44. Hamilton, T. C.; Young, R. C.; McKoy, W. M.; Grotzinger, K. R.; Green, J. A.; Chu, E. W.; Whang-Peng, J.; Rogan, A. M.; Green, W. R.; Ozols, R. F. Characterization of a human ovarian carcinoma cell line (NIH:OVCAR-3) with androgen and estrogen receptors. Cancer Res. 1983, 43, 5379-5389.
45. Mitchell, S.; Abel, P.; Ware, M.; Stamp, G.; Lalani, E. Phenotypic and genotypic characterization of commonly used human prostatic cell lines. BJU Int. 2000, 85, 932-944.
46. Evangelou, A.; Jindal, S. K.; Brown, T. J.; Letarte, M. Downregulation of transforming growth factor beta receptors by androgen in ovarian cancer cells. Cancer Res. 2000, 60, 929-935.
47. Andò, S.; De Amicis, F.; Rago, V.; Carpino, A.; Maggiolini, M.; Panno, M. L.; Lanzino, M. Breast cancer: from estrogen to androgen receptor. Mol. Cell. Endocrinol. 2002, 193, 121-128.
48. Magklara, A.; Brown, T. J.; Diamandis, E. P. Characterization of androgen receptor and nuclear receptor co-regulator expression in human breast cancer cell lines exhibiting differential regulation of kallikreins 2 and 3. Int. J. Cancer 2002, 100, 507-514.
49. Humm, J. L.; Howell, R. W.; Rao, D. V. Dosimetry of Augerelectron- emitting radionuclides: report no. 3 of AAPM Nuclear Medicine Task Group No. 6. Med. Phys. 1994, 21, 1901-1915.
50. 125I radioactive disintegrations. Biophys. J. 1976, 16, 1003-1012.
51. 125I incorporated into mammalian DNA. Proc. Natl. Acad. Sci. U.S.A. 1974, 71, 4836-4838.
52. Pastwa, E.; Neumann, R. D.; Mezhevaya, K.; Winters, T. A. Repair of radiation-induced DNA double-strand breaks is dependent upon radiation quality and the structural complexity of double-strand breaks. Radiat. Res. 2003, 159, 251-261.
53. Hampton, A.; Hampton, E. G.; Eidinoff, M. L. Nucleotides. III. Synthesis and effects with cells in culture of 131-I-labeled 5-iodo-2′-deoxyuridine- 5′-phosphate. Biochem. Pharmacol. 1962, 11, 155-159.
54. Seitz, U.; Wagner, M.; Neumaier, B.; Wawra, E.; Glatting, G.; Leder, G.; Schmid, R. M.; Reske, S. N. Evaluation of pyrimidine metabolising enzymes and in vitro uptake of 3′-[(18)F]fluoro-3′-deoxythymidine ([(18)F]FLT) in pancreatic cancer cell lines. Eur. J. Nucl. Med. Mol. Imaging 2002, 29, 1174-1181.
55. Aubé, M.; Larochelle, C.; Ayotte, P. 1,1-Dichloro-2,2-bis(p- chlorophenyl) ethylene (p,p′-DDE) disrupts the estrogen-androgen balance regulating the growth of hormone-dependent breast cancer cells. Breast Cancer Res. 2008, 10, R16.
56. Katsuoka, Y.; Hoshino, H.; Shiramizu, M.; Sakabe, K.; Seiki, K. Autoradiographic and cytochemical localization of androgen in human prostatic cancer cell lines. Urology 1986, 28, 228-231.
57. Tilley, W. D.; Wilson, C. M.; Marcelli, M.; McPhaul, M. J. Androgen receptor gene expression in human prostate carcinoma cell lines. Cancer Res. 1990, 50, 5382-5386.
58. Hu, Y. C.; Wang, P. H.; Yeh, S.; Wang, R. S.; Xie, C.; Xu, Q.; Zhou, X.; Chao, H. T.; Tsai, M. Y.; Chang, C. Subfertility and defective folliculogenesis in female mice lacking androgen receptor. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 11209-11214.
59. de Moor, P.; Verhoeven, G.; Heyns, W. A comparative study of the androgen receptor apparatus in adult rodents. J. Steroid Biochem. 1975, 6, 437-442.
60. Pelletier, G.; Luu-The, V.; Li, S.; Labrie, F. Localization and estrogenic regulation of androgen receptor mRNA expression in the mouse uterus and vagina. J. Endocrinol. 2004, 180, 77-85.
61. Baranowska-Kortylewicz, J.; Nearman, J.; Kortylewicz, Z. P. Effect of sex hormone binding globulin on the development of ovarian cancer in a mouse model. Open Cancer J. 2008, 2, 59-65.
62. Lee, E. C.; Tenniswood, M. P. Emergence of metastatic hormone-refractory disease in prostate cancer after anti-androgen therapy. J. Cell. Biochem. 2004, 91, 662-670.
63. Mohler, J. L. Castration-recurrent prostate cancer is not androgen-independent. Adv. Exp. Med. Biol. 2008, 617, 223-234.
64. Gaston, K. E.; Kim, D.; Singh, S.; Ford, O. H.; Mohler, J. L. Racial differences in androgen receptor protein expression in men with clinically localized prostate cancer. J. Urol. 2003, 170, 990-993.
65. Lange, E. M.; Sarma, A. V.; Ray, A.; Wang, Y.; Ho, L. A.; Anderson, S. A.; Cunningham, J. M.; Cooney, K. A. The androgen receptor CAG and GGN repeat polymorphisms and prostate cancer susceptibility in African-American men: results from the Flint Men's Health Study. J. Hum. Genet. 2008, 53, 220-226.
66. Berger, G.; Maziere, M.; Prenant, C.; Sastre, J.; Comar, D. Synthesis of high specific activity 11C 17 alpha methyltestosterone. Int. J. Appl. Radiat. Isot. 1981, 32, 811-815.
67. Liu, A.; Carlson, K. E.; Katzenellenbogen, J. A. Synthesis of high affinity fluorine-substituted ligands for the androgen receptor. Potential agents for imaging prostatic cancer by positron emission tomography. J. Med. Chem. 1992, 35, 2113-2129.
68. 18F]fluoro-17alpha-methyl-5alpha-dihydrotestosterone: a ligand for androgen receptor-mediated imaging of prostate cancer. Nucl. Med. Biol. 2001, 28, 85-90.
69. 125I]iodovinyl-19-nortestosterones: potential radioligands for androgen and progesterone receptors. Steroids 2003, 68, 1163-1171.
70. Dehdashti, F.; Picus, J.; Michalski, J. M.; Dence, C. S.; 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, 344-350.
71. Parent, E. E.; Carlson, K. E.; Katzenellenbogen, J. A. Synthesis of 7alpha-(fluoromethyl)dihydrotestosterone and 7alpha-(fluoromethyl) nortestosterone, structurally paired androgens designed to probe the role of sex hormone binding globulin in imaging androgen receptors in prostate tumors by positron emission tomography. J. Org. Chem. 2007, 72, 5546-5554.
72. 99mTc, Re) compounds based on the androgen receptor targeting molecule flutamide. Bioconjugate Chem. 2009, 20, 78-86.
73. Nakhla, A. M.; Rosner, W. Stimulation of prostate cancer growth by androgens and estrogens through the intermediacy of sex hormone-binding globulin. Endocrinology 1996, 137, 4126-4129.
74. Hryb, D. J.; Nakhla, A. M.; Kahn, S. M.; St George, J.; Levy, N. C.; Romas, N. A.; Rosner, W. Sex hormone-binding globulin in the human prostate is locally synthesized and may act as an autocrine/paracrine effector. J. Biol. Chem. 2002, 277, 26618-26622.
75. Kahn, S. M.; Li, Y. H.; Hryb, D. J.; Nakhla, A. M.; Romas, N. A.; Cheong, J.; Rosner, W. Sex hormone-binding globulin influences gene expression of LNCaP and MCF-7 cells in response to androgen and estrogen treatment. Adv. Exp. Med. Biol. 2008, 617, 557-564.
76. Hammes, A.; Andreassen, T. K.; Spoelgen, R.; Raila, J.; Hubner, N.; Schulz, H.; Metzger, J.; Schweigert, F. J.; Luppa, P. B.; Nykjaer, A.; Willnow, T. E. Role of endocytosis in cellular uptake of sex steroids. Cell 2005, 122, 751-762.
77. Porto, C. S.; Gunsalus, G. L.; Bardin, C. W.; Phillips, D. M.; Musto, N. A. Receptor-mediated endocytosis of an extracellular steroid-binding protein (TeBG) in MCF-7 human breast cancer cells. Endocrinology 1991, 129, 436-445.
78. 18F-fluoromethyl-nortestosterone: ligands to determine the role of sex hormone-binding globulin for steroidal radiopharmaceuticals. J. Nucl. Med. 2008, 49, 987-994.
79. Fortunati, N. Sex hormone-binding globulin: not only a transport protein. What news is around the corner? J. Endocrinol. Invest. 1999, 22, 223-234.
80. Caldwell, J. D.; Shapiro, R. A.; Jirikowski, G. F.; Suleman, F. Internalization of sex hormone-binding globulin into neurons and brain cells in vitro and in vivo. Neuroendocrinology 2007, 86, 84-93.
81. Hryb, D. J.; Khan, M. S.; Romas, N. A.; Rosner, W. The control of the interaction of sex hormone-binding globulin with its receptor by steroid hormones. J. Biol. Chem. 1990, 265, 6048-6054.
82. Papadopoulou, N.; Papakonstanti, E. A.; Kallergi, G.; Alevizopoulos, K.; Stournaras, C. Membrane androgen receptor activation in prostate and breast tumor cells: molecular signaling and clinical impact. IUBMB Life 2009, 61, 56-61.
83. Steinsapir, J.; Socci, R.; Reinach, P. Effects of androgen on intracellular calcium of LNCaP cells. Biochem. Biophys. Res. Commun. 1991, 179, 90-96.
84. Hatzoglou, A.; Kampa, M.; Kogia, C.; Charalampopoulos, I.; Theodoropoulos, P. A.; Anezinis, P.; Dambaki, C.; Papakonstanti, E. A.; Stathopoulos, E. N.; Stournaras, C.; Gravanis, A.; Castanas, E. Membrane androgen receptor activation induces apoptotic regression of human prostate cancer cells in vitro and in vivo. J. Clin. Endocrinol. Metab. 2005, 90, 893-903.
85. Wang, Z.; Liu, L.; Hou, J.; Wen, D.; Yan, C.; Pu, J.; Ouyang, J.; Pan, H. Rapid membrane effect of testosterone in LNCaP cells. Urol. Int. 2008, 81, 353-359.
86. Dambaki, C.; Kogia, C.; Kampa, M.; Darivianaki, K.; Nomikos, M.; Anezinis, P.; Theodoropoulos, P. A.; Castanas, E.; Stathopoulos, E. N. Membrane testosterone binding sites in prostate carcinoma as a potential new marker and therapeutic target: study in paraffin tissue sections. BMC Cancer 2005, 5, 148.
87. Makrigiorgos, G. M.; Berman, R. M.; Baranowska-Kortylewicz, J.; Bump, E.; Humm, J. L.; Adelstein, S. J.; Kassis, A. I. DNA damage produced in V79 cells by DNA-incorporated iodine-123: a comparison with iodine-125. Radiat. Res. 1992, 129, 309-314.
88. 125I]iodo-2′-deoxyuridine. Radiat. Res. 1989, 118, 532-544.
89. Sharma, C. V.; Reddy, C. G.; Krishna, P. R. Zirconium(IV) chloride catalyzed new and efficient protocol for the selective cleavage of p-methoxybenzyl ethers. J. Org. Chem. 2003, 68, 4574-4575.
90. Hoskins, J. M.; Meynell, G. G.; Sanders, F. K. A comparison of methods for estimating the viable count of a suspension of tumour cells. Exp. Cell Res. 1956, 11, 297-305.
91. Heptinstall, J.; Rapley, R. Spectrophotometric Analysis of Nucleic Acids. In The Nucleic Acid Protocols Handbook; Rapley, R., Ed.; Humana Press: Totowa, NJ, 2000; pp 57-60.
92. Skerrow, C. J.; Matoltsy, A. G. Isolation of epidermal desmosomes. J. Cell Biol. 1974, 63, 515-523.