Synthesis, characterization, and biological evaluation of M(I)(CO) 3(NNO) complexes (M = Re, 99mTc) conjugated to 2-(4-aminophenyl)benzothiazole as potential breast cancer radiopharmaceuticals

Journal of Medicinal Chemistry

Volumn 49, Issue 18, 2006, Pages 5408-5410

  Tzanopoulou, Stamatia ^a   Pirmettis, Ioannis C ^a   Patsis, George ^a   Paravatou Petsotas, Maria ^a   Livaniou, Evangelia ^a   Papadopoulos, Minas ^a   Pelecanou, Maria ^a  

^a INSTITUTE OF NANOSCIENCE AND NANOTECHNOLOGY   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 AMINOPHENYL)BENZOTHIAZOLE; ANTINEOPLASTIC AGENT; CARBONYL DERIVATIVE; ORGANOMETALLIC COMPOUND; RADIOPHARMACEUTICAL AGENT; RHENIUM 186; RHENIUM 188; RHENIUM COMPLEX; TECHNETIUM 99M; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; BREAST CANCER; CANCER RADIOTHERAPY; CELL STRAIN MCF 7; CONTROLLED STUDY; DIAGNOSTIC IMAGING; DRUG CLEARANCE; DRUG CONJUGATION; DRUG DISTRIBUTION; DRUG SYNTHESIS; FETUS; FLUORESCENCE; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; NORMAL HUMAN; PLASMA CLEARANCE; SINGLE PHOTON EMISSION COMPUTER TOMOGRAPHY;

ANIMALS; ANTINEOPLASTIC AGENTS; BENZOTHIAZOLES; BREAST NEOPLASMS; CELL LINE; CELL LINE, TUMOR; FEMALE; FIBROBLASTS; HUMANS; MICE; ORGANOMETALLIC COMPOUNDS; RADIOPHARMACEUTICALS; RHENIUM; STRUCTURE-ACTIVITY RELATIONSHIP; TECHNETIUM; THIAZOLES; TOMOGRAPHY, EMISSION-COMPUTED, SINGLE-PHOTON;

EID: 33748558464     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0606387     Document Type: Article

References (35)

1. The American Cancer Society Web page: Cancer Statistics 2006. http://www.cancer.org/downloads/STT/Cancer_Statistics_2006_Presentation.ppt#4.
2. Boyle P.; Ferlay J. Cancer Incidence and Mortality in Europe, 2004. Ann. Oncol. 2005, 16, 481-488.
3. The American Cancer Society Web page: Breast Cancer Facts & Figures 2005-2006. http://www.cancer.org/downloads/STT/CAFF2005BrF.pdf.
4. (a) Benard, F.; Turcotte, E. Imaging in Breast Cancer: Single-Photon Computed Tomography and Positron-Emission Tomography. Breast Cancer Res. 2005, 7, 153-162.
5. (b) Schillaci, O.; Buscombe, J. R. Breast Scintigraphy Today: Indications and Limitations. Eur. J. Nucl. Med. Mol. Imaging 2004, 31, S35-45.
6. Schnall, M. D.; Orel, S. G. Breast MRI. Breast Dis. 1998, 10, 97-111.
7. Jurisson, S. S.; Lydon, J. D. Potential Technetium Small Molecule Radiopharmaceuticals. Chem. Rev. 1999, 99, 2205-2218.
8. JurKhalkhali, I.; Mena, I.; Diggles, L. Review of Imaging Techniques for the Diagnosis of Breast Cancer: A New Role for Prone Scintimammography, Using Technetium-99m Sestamibi. Eur. J. Nucl. Med. 1994, 21, 357-362.
9. Rambaldi, P. F.; Mansi, L.; Procaccini, E.; Di-Gregorio, F.; Del-Vecchio, E. Breast Cancer Detection with Tc-99m Tetrofosmin. Clin. Nucl. Med. 1995, 20, 703-705.
10. Turhal, N. S.; Dane, F.; Dede, F.; Gumus, M.; Yumuk, P. F.; Cakalagaoglu, F.; Savci, D.; Karaman, M.; Gulluoglu, B.; Turoglu, H. T. 99m-Tc-MDP- Scintimammography in the Evaluation of Breast Masses or Tumor Angiogenesis. Anticancer Res. 2004, 24, 1999-2006.
11. (a) 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.
12. (b) Dilworth, J.; Parrot, S. The Biomedical Chemistry of Technetium and Rhenium. Chem. Soc. Rev. 1998, 27, 43-55.
13. (a) Hashimoto, K.; Yoshihara, K. Rhenium Complexes Labelled with Re-186, Re-188 for Nuclear Medicine. Top. Curr. Chem. 1996, 176, 275-291.
14. (b) Schubiger, P. A.; Alberto, R.; Smith, A. Vehicles, Chelators, and Radionuclides: Choosing the "Building Blocks" of an Effective Therapeutic Radioimmunoconjugate. Bioconjugate Chem. 1996, 7, 165-179.
15. (a) Zamora, P. O.; Gulhke, S.; Bender, H.; Diekmann, D.; Rhodes, B. A.; Biersack, H. J.; Knapp, F. F. Experimental Radiotherapy of Receptor-Positive Human Prostate Adenocarcinoma with Re-188-RC-160, a Directly-Radiolabeled Somatostatin Analogue. Int. J. Cancer 1996, 65, 214-220.
16. (b) Zamora, P. O.; Marek, M. J.; Knapp, F. F. Preparation of Re-188-RC-160 Somatostatin Analog: A Peptide for Local/Regional Radiotherapy. Appl. Radiat. Isot. 1997, 48, 305-309.
17. (c) Safavy, A.; Khazaeli, M. B.; Qin, H.; Buchsbaum, D. J. Synthesis of Bombesin Analogues for Radiolabeling with Rhenium-188. Cancer 1997, 80, 2354-2359.
18. (d) Volkert, W. A.; Hoffman, T. J. Therapeutic Radiopharmaceuticals. Chem. Rev. 1999, 99, 2269-2292.
19. (e) Heeg, M. J.; Jurisson, S. S. The Role of Inorganic Chemistry in the Development of Radiometal Agents for Cancer Therapy. Acc. Chem. Res. 1999, 32, 1053-1060.
20. (f) Heppeler, A.; Froidevaux, S.; Eberle, A. N.; Maecke, H. R. Receptor Targeting for Tumor Localization and Therapy with Radiopeptides. Curr. Med. Chem. 2000, 7, 971-994.
21. (g) Gali, H.; Hoffman, T. J.; Sieckman, G. L.; Owen, N. K.; Katti, K. V.; Volkert, W. A. Synthesis, Characterization, and Labelling with Tc-99m/Re-188 of Peptide Conjugates Containing a Dithia-Bisphosphine Chelating Agent. Bioconjugate Chem. 2001, 12, 354-363.
22. (h) Miao, Y.; Owen, N. K.; Whitener, D.; Gallazzi, F.; Hoffman, T. J.; Quinn, T. P. In Vivo Evaluation of (188)Re-Labeled Alpha-Melanocyte Stimulating Hormone Peptide Analogs for Melanoma Therapy. Int. J. Cancer. 2002, 101, 480-487.
23. (i) Miao Y.; Owen, N. K.; Fisher, D. R.; Hoffman, T. J.; Quinn, T. P. Therapeutic Efficacy of a Re-188-Labelled Alpha-Melanocyte-Stimulating Hormone Peptide Analog in Murine and Human Melanoma-Bearing Mouse Models. J. Nucl. Med. 2005, 46, 121-129.
24. (a) Shi, D.-F.; Bradshaw, T.; 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. J. Med. Chem. 1996, 39, 3375-3384.
25. (b) 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 Anti-Tumour Activity. Br. J. Cancer 1998, 77, 745-752.
26. (a) Bradshaw, T. D.; Stevens, M. F. G.; Westwell, A. D. Discovery of the Potent and Selective Antitumour Agent 2-(4-Amino-3-methylphenyl)benzothiazole (DF 203) and Related Compounds. Curr. Med. Chem 2001, 8, 203-210.
27. (b) Bradshaw, T. D.; Westwell, A. D. The Development of the Antitumor Benzothiazole Prodrug, Phortress, as a Clinical Candidate. Curr. Med. Chem. 2004, 11, 1009-1021.
28. For further information, see Supporting Information.
29. (a) 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.
30. (b) Policar, C.; Lambert, F.; Cesario, M.; Morgenstern-Badarau, I. An Inorganic Helix [Mn(IPG)(MeOH)]n[PF6]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.
31. 6] by Alkaline Titration. J. Chem. Soc., Dalton Trans. 1994, 19, 2815-2820.
32. - in Aqueous Solution and Its Reaction with a Bifunctional Ligand. J. Am. Chem. Soc. 1998, 120, 7987-7988.
33. 99mTc(I)-Tricarbonyl Complexes: A Hint for the Future Functionalization of Biomolecules. Bioconjugate Chem. 2000, 11, 345-351.
34. 99mTc Complexes for Correlating Fluorescence and Radioimaging Studies. J. Am. Chem. Soc. 2004, 126, 8598-8599.
35. 99mTc Complexes of Biotin Derivatives for Fluorescence and Radioimaging Studies. Bioconjugate Chem. 2006, 17, 590-596.