Evaluation of Re and 99mTc complexes of 2-(4′-aminophenyl) benzothiazole as potential breast cancer radiopharmaceuticals

Journal of Medicinal Chemistry

Volumn 53, Issue 12, 2010, Pages 4633-4641

  Tzanopoulou, Stamatia ^a   Sagnou, Marina ^a   Paravatou Petsotas, Maria ^a   Gourni, Eleni ^a   Loudos, George ^b   Xanthopoulos, Stavros ^a   Lafkas, Daniel ^c   Kiaris, Hippokratis ^c   Varvarigou, Alexandra ^a   Pirmettis, Ioannis C ^a   Papadopoulos, Minas ^a   Pelecanou, Maria ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

^b UNIVERSITY OF WEST ATTICA   (Greece)

^c UNIVERSITY OF ATHENS MEDICAL SCHOOL   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4' AMINOPHENYL)BENZOTHIAZOLE; ANTINEOPLASTIC AGENT; RHENIUM COMPLEX; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BREAST CANCER; CANCER CELL; CELL STRAIN MCF 7; CONTROLLED STUDY; CYTOTOXICITY; DRUG DISTRIBUTION; DRUG SCREENING; DRUG SYNTHESIS; DRUG UPTAKE; FEMALE; FIBROBLAST; FLUORESCENCE MICROSCOPY; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; BREAST NEOPLASMS; CELL LINE, TUMOR; COORDINATION COMPLEXES; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; HUMANS; MICE; MICE, SCID; NEOPLASM TRANSPLANTATION; RADIOPHARMACEUTICALS; RHENIUM; STRUCTURE-ACTIVITY RELATIONSHIP; TECHNETIUM; TISSUE DISTRIBUTION; TRANSPLANTATION, HETEROLOGOUS;

EID: 77953773495     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1001293     Document Type: Article

References (34)

1. Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. The discovery of the potent and selective antitumor agent 2-(4-amino-3-methylphenyl)benzothiazole (DF 203) and related compounds Curr. Med. Chem. 2001, 8, 203-210
2. Bradshaw, T. D.; Westwell, A. D. The development of the antitumour benzothiazole prodrug, Phortress, as a clinical candidate Curr. Med. Chem. 2004, 11, 1241-1253
3. Shi, D.-F.; Bradshaw, T. D.; Wrigley, S.; McCall, C. J.; Lelieveld, P.; Fichtner, I.; Stevens, M. F. G. Antitumor benzothiazoles. 3. Synthesis of 2-(4-aminophenyl)benzothiazoles and evaluation of their activities against breast cancer cell lines in vitro and in vivo J. Med. Chem. 1996, 39, 3375-3384
4. Bradshaw, T. D.; Wrigley, S.; Shi, D.-F.; Schultz, R. J.; Paull, K. D.; Stevens, M. F. G. 2-(4-Aminophenyl)benzothiazoles: novel agents with selective profiles of in vitro and in vivo activity Br. J. Cancer 1998, 77, 745-752
5. Chua, M.-S.; Shi, D.-F.; Wrigley, S.; Bradshaw, T. D.; Hutchinson, I.; Shaw, P. N.; Barrett, D. A.; Stanley, L. A.; Stevens, M. F. G. Antitumor benzothiazoles. 7. Synthesis of 2-(4-acylaminophenyl)benzothiazoles and investigations into the role of acetylation in the antitumor activities of the parent amines J. Med. Chem. 1999, 42, 381-392
6. Kashiyama, E.; Hutchinson, I.; Chua, M.-S.; Stinson, S. F.; Phillips, L. R.; Kaur, G.; Sausville, E. A.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 8. Synthesis, metabolic formation, and biological properties of the C- and N-oxidation products of antitumor 2-(4-aminophenyl) benzothiazoles J. Med. Chem. 1999, 42, 4172-4184
7. Bradshaw, T. D.; Shi, D.-F.; Schultz, R. J.; Paull, K. D.; Kelland, L.; Wilson, A.; Garner, C.; Fiebig, H. H.; Wrigley, S.; Stevens, M. F. G. Influence of 2-(4-aminophenyl) benzothiazoles on growth of human ovarian carcinoma cells in vitro and in vivo Br. J. Cancer 1998, 78, 421-429
8. Hutchinson, I.; Chua, M.-S.; Browne, H. L.; Trapani, V.; Bradshaw, T. D.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 14. The synthesis and in vitro biological properties of fluorinated 2-(4-aminophenyl) benzothiazoles J. Med. Chem. 2001, 44, 1446-1455
9. Hutchinson, I.; Jennings, S. A.; Vishnuvajjala, B. R.; Westwell, A. D.; Stevens, M. F. G. Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl)benzothiazole amino acid prodrugs J. Med. Chem. 2002, 45, 744-747
10. Liu, S. The role of coordination chemistry in the development of target-specific radiopharmaceuticals Chem. Soc. Rev. 2004, 33, 445-461
11. Liu, S. Bifunctional coupling agents for radiolabelling of biomolecules and target-specific delivery of metallic radionuclides Adv. Drug Delivery Rev. 2008, 60, 1347-1370
12. 99mTc) conjugated to 2-(4-aminophenyl)benzothiazole as potential breast cancer radiopharmaceuticals J. Med. Chem. 2006, 49, 5408-5410
13. 99mTc radiopharmaceuticals Ann. Nucl. Med. 2002, 16, 79-93
14. Mindt, T.; Struthers, H.; Garcia-Garayoa, E.; Desbouis, D.; Schibli, R Strategies for the development of novel tumor targeting technetium and rhenium radiopharmaceuticals Chimia 2007, 61, 725-731
15. 188Re-labelled radiopharmaceuticals for radionuclide therapy Nucl. Med. Commun. 2006, 27, 223-229
16. Hashimoto, K.; Yoshihara, K. Rhenium complexes labeled with Re-186, Re-188 for nuclear medicine Technetium Rhenium Top. Curr. Chem. 1996, 176, 275-291
17. Deutsch, E.; Libson, K.; Vanderheyden, J.-L.; Ketring, A. R.; Maxon, H. R. The chemistry of rhenium and technetium as related to the use of isotopes of these elements in therapeutic and diagnostic nuclear-medicine Nucl. Med. Biol. 1986, 13, 465-477
18. Dilworth, J.; Parrot, S. The biomedical chemistry of technetium and rhenium Chem. Soc. Rev. 1998, 27, 43-55 (Pubitemid 128653040)
19. Phoon, C. W.; Ng, P. Y.; Ting, A. E.; Yeo, S. L.; Sim, M. M. Biological evaluation of hepatitis C virus helicase inhibitors Bioorg. Med. Chem. Lett. 2001, 11, 1647-1650
20. Inoue, H.; Konda, M.; Hashiyama, T.; Otsuka, H.; Watanabe, A.; Gaino, M.; Takahashi, K.; Date, T.; Okamura, K.; Takeda, M.; Narita, H.; Murata, S.; Odawara, A.; Sasaki, H.; Nagao, T. Synthesis and biological evaluation of alkyl, alkoxy, alkylthio, or amino-substituted 2,3-dihydro-1,5-benzothiazepin-4(5 H)-ones Chem. Pharm. Bull. 1997, 45 (6) 1008-1026
21. n: structural and magnetic properties of a syn-anti carboxylate-bridged manganese(II) chain involving a tetradentate ligand Eur. J. Inorg. Chem. 1999, 12, 2201-2207
22. 6] by alkaline titration J. Chem. Soc., Dalton Trans. 1994, 19, 2815-2820
23. - in aqueous solution and its reaction with a bifunctional ligand J. Am. Chem. Soc. 1998, 120, 7987-7988
24. Hill, D. M.; Barnes, R. K.; Wong, H. K. Y.; Zawadzki, A. W. The quantification of technetium in generator-derived pertechnetate using ICP-MS Appl. Radiat. Isot. 2000, 53, 415-419
25. Bradshaw, T. D.; Stone, E. L.; Trapani, V.; Leong, C.-O.; Matthews, C. S.; te Poele, R.; Stevens, M. F. G. Mechanisms of aquired resistance to 2-(4-amino-3-methylphenyl)benzothiazole in breast cancer lines Breast Cancer Res. Treat. 2008, 110, 57-68
26. Kassis, A. I.; Adelstein, S. J. Radiobiologic principles in radionuclide therapy J. Nucl. Med. 2005, 46 (Suppl.) 4S-12S
27. Goddu, S. M.; Howell, R. W.; Rao, D. V. Cellular dosimetry: absorbed fractions for monoenergetic electron and alpha particle sources and S-values for radionuclides uniformly distributed in different cell compartments J. Nucl. Med. 1994, 35, 303-316
28. Bradshaw, T. D.; Fichtner, I.; Bibby, M. J.; Double, J. A.; Cooper, P. A.; Alley, M. C.; Tomaszewjski, J. E.; Donahue, S.; Stinson, S. F.; Sausville, E. A.; Stevens, M. F. G. Preclinical evaluation of amino acid prodrugs of novel antitumor 2-(4-amino-methylphenyl)benzothiazoles Mol. Cancer Ther. 2002, 1, 239-246
29. Loaiza-Pérez, A. I.; Trapani, V.; Hose, C.; Singh, S. S.; Trepel, J. B.; Stevens, M. F. G.; Bradshaw, T. D.; Sausville, E. A. Aryl hydrocarbon receptor mediates sensitivity of MCF-7 breast cancer cells to antitumor agent 2-(4-amino-3-methylphenyl)benzothiazole Mol. Pharmacol. 2002, 61, 13-19
30. Okarvi, S. M.; Jammaz, I. A. Preparation and in vitro and in vivo evaluation of technetium-99m-labeled folate and methotrexate conjugates as tumor imaging agents Cancer Biother. Radiopharm. 2006, 21, 49-60
31. 99mTc-GAP-EDL Eur. J. Nucl. Med. Mol. Imaging 2007, 34, 354-362 (Pubitemid 46295345)
32. 99mTc glucarate high-resolution imaging of drug sensitive and drug resistant human breast cancer xenografts in SCID mice Nucl. Med. Commun. 2004, 25, 711-720
33. Tuxhorn, J. A.; McAlhany, S. J.; Dang, T. D.; Ayala, G. E.; Rowley, D. R. Stromal cells promote angiogenesis and growth of human prostate tumors in a differential reactive stroma (DRS) xenograft model Cancer Res. 2002, 62, 3298-3307
34. Loudos, G.; Majewski, S.; Wojcik, R.; Weisenberger, A.; Sakellios, N.; Nikita, K.; Uzunoglu, N.; Bouziotis, P.; Xanthopoulos, S.; Varvarigou, A. Performance evaluation of a dedicated camera suitable for dynamic radiopharmaceuticals evaluation in small animals IEEE Trans. Nucl. Sci. 2007, 54, 454-460