Organometallic anticancer agents: Cellular uptake and cytotoxicity studies on thiol derivatives of the antitumor agent molybdocene dichloride

Journal of Medicinal Chemistry

Volumn 48, Issue 6, 2005, Pages 2093-2099

  Waern, Jenny B ^a   Dillon, Carolyn T ^a,b   Harding, Margaret M ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 THIO 2,3,4,5 TETRAACETYL BETA DEXTRO GLUCOSE; 1 THIO BETA DEXTRO GLUCOSE; 4 THIOL 2,3,5,6 TETRAFLUOROBENZOIC ACID; ANTINEOPLASTIC AGENT; DIMETHYL SULFOXIDE; GLUTATHIONE DERIVATIVE; GRAPHITE; METALLOCENE MOLYBDOCENE DICHLORIDE; ORGANOMETALLIC COMPOUND; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; AQUEOUS SOLUTION; ARTICLE; ATOMIC ABSORPTION SPECTROMETRY; BREAST CELL; CELL STRAIN V 79; CELL TRANSPORT; CHINESE HAMSTER; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACETYLATION; DRUG SOLUBILITY; HYDROLYSIS; NONHUMAN; OVARY CELL; PH; PLASMA;

ANIMALS; ANTINEOPLASTIC AGENTS; CELL LINE; CELL LINE, TUMOR; CRICETINAE; CRICETULUS; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; HUMANS; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS;

EID: 15444377931     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm049585o     Document Type: Article

References (49)

1. Rosenberg, B.; Van Camp, L.; Grimley, E. B.; Thomson, A. J. The Inhibition of Growth or Cell Division in Escherichia coli by Different Ionic Species of Platinum(IV) Complexes. J. Biol. Chem. 1967, 242, 1347-1352.
2. Fuertes, M. A.; Alonso, C.; Perez, J. M. Biochemical modulation of cisplatin mechanisms of action: enhancement of antitumor activity and circumvention of drug resistance. Chem. Rev. 2003, 103, 645-662.
3. Boulikas, T.; Vougiouka, M. Cisplatin and platinum drugs at the molecular level. Oncol. Rep. 2003, 10, 1663-1682.
4. Wheate, N. J.; Collins, J. G. Multinuclear platinum complexes as anti-cancer drugs. Coord. Chem. Rev. 2003, 241, 133-145.
5. Natile, G.; Coluccia, M. Current status of trans-platinum compounds in cancer therapy. Coord. Chem. Rev. 2001, 216-217, 383-410.
6. Clarke, M. J.; Zhu, F.; Frasca, D. R. Non-Platinum Chemotherapeutic Metallopharmaceuticals. Chem. Rev. 1999, 99, 2511-2533.
7. Köpf-Maier, P. Complexes of Metals other than Platinum as Antitumour Agents. Eur. J. Clin. Pharmacol. 1994, 47, 1-16.
8. Farrell, N. Metal complexes as drugs and chemotherapeutic agents. Comp. Coord. Chem. 2 2004, 9, 809-840.
9. Manzotti, C.; Pratesi, G.; Menta, E.; Domenico, R. D.; Cavalletti, E.; Fiebig, H. H.; Kelland, L. R.; Farrell, N.; Polizzi, D.; Supino, R.; Pezzoni, G.; Zunino, F. BBR 3464: a novel triplatinum complex, exhibiting a preclinical profile of antitumor efficacy different from cisplatin. Clin. Cancer Res. 2000, 6, 2626-2634.
10. Farrell, N. Polynuclear charged platinum compounds as a new class of anticancer agents: toward a new paradigm. Platinum-Based Drugs Cancer Ther. 2000, 321-338.
11. Morris, R. E.; Aird, R. E.; Murdoch, P. D. S.; Chen, H.; Cummings, J.; Hughes, N. D.; Parsons, S.; Parkin, A.; Boyd, G.; Jodrell, D. I.; Sadler, P. J.. Inhibition of Cancer Cell Growth by Ruthenium(II) Arene Complexes. J. Med. Chem. 2001, 44, 3616-3621.
12. Kratz, F.; Hartmann, M.; Keppler, B.; Messori, L. The Binding Properties of Two Antitumor Ruthenium(III) Complexes to Apotransferrin. J. Biol. Chem. 1994, 269, 2581-2588.
13. Kröger, N.; Kleeberg, U. R.; Mross, K.; Edler, L.; Sass, G.; Hossfeld, D. K. Phase II Clinical Trial of Titanocene Dichloride in Patients with Metastatic Breast Cancer. Onkologie 2000, 23, 60-62.
14. Lümmen, G.; Sperling, H.; Luboldt, H.; Otto, T.; Rübben, H. Phase II Trial of Titanocene Dichloride in Advanced Renal-Cell Carcinoma. Cancer Chemother. Pharmacol. 1998, 42, 415-417.
15. Köpf-Maier, P.; Krahl, D. Tumor Inhibition by Metallocenes: Ultrastructural Localization of Titanium and Vanadium in Treated Tumor Cells by Electron Energy Loss Spectroscopy. Chem. Biol. Interact. 1983, 44, 317-328.
16. Köpf-Maier, P.; Wagner, W.; Köpf, H. Different Inhibition Pattern of the Nucleic Acid Metabolism after In Vitro Treatment with Titanocene and Vanadocene Dichlorides. Naturwissenschaften 1981, 68, 272-273.
17. Köpf-Maier, P.; Köpf, H. Metallocene Complexes- Organometallic Antitumor Agents. Drugs Future 1986, 11, 297-320.
18. 2, M = Ti, V, Zr. Aqueous Kinetics, Equilibria, and Mechanistic Implications for a New Class of Antitumor Agents. J. Am. Chem. Soc. 1985, 107, 947-953.
19. Harding, M. M.; Mokdsi, G. Antitumour Metallocenes: Structure-Activity Studies and Interactions with Biomolecules. Curr. Med. Chem. 2000, 7, 1289-1303.
20. IV-Protein Complex: Potential Relevance to Anticancer Activity of Titanocenes. Angew. Chem., Int. Ed. 1998, 37, 1577-1579.
21. IV-Transferrin by Cancer Cells: Understanding the Mechanism of Action of the Anticancer Drug Titanocene Dichloride. Biochemistry 2000, 39, 10023-10033.
22. Köpf-Maier, P.; Klapötke, T. Ionic Rhenocene Derivatives with Antitumor Activity. Cancer Chemother. Pharmacol. 1992, 29, 361-366.
23. Köpf-Maier, P.; Klapötke, T. Antitumor activity of Ionic Niobocene and Molybdenocene Complexes in High Oxidation States. J. Cancer Res. Clin. Oncol. 1992, 118, 216-221.
24. Köpf-Maier, P.; Köpf, H. Organometallic Titanium, Vanadium, Niobium, Molybdenum and Rhenium Complexes- Early Transition Metal Antitumour Drugs. Metal Compounds in Cancer Therapy; Chapman and Hall: London, 1994; pp 109-146.
25. Waern, J. B.; Harding, M. M. Coordination Chemistry of the Antitumor Metallocene Molybdocene Dichloride with Biological Ligands. Inorg. Chem. 2004, 43, 206-213.
26. 1H NMR study of the interaction of antitumor metallocenes with glutathione. J. Inorg. Biochem. 2001, 86, 611-616.
27. Mokdsi, G.; Harding, M. M. Inhibition of Human Topoisomerase II by the Antitumor Metallocenes. J. Inorg. Biochem. 2001, 83, 205-209.
28. Harding, M. M.; Mokdsi, G.; Mackay, J. P.; Prodigalidad, M.; Lucas, S. W. Interaction of the Antitumor Agent Molybdocene Dichloride with Oligonucleotides. Inorg. Chem. 1998, 37, 2432-2437.
29. Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, A. L.; Marks, T. J. Metallocene antitumor agents. Solution and solid-state molybdenocene coordination chemistry of DNA constituents. J. Am. Chem. Soc. 1991, 113, 9027-9045.
30. 2 with Nucleic Acid Constituents. J. Med. Chem. 1994, 37, 1936-1941.
31. Kuo, L. Y.; Liu, A. H.; Marks, T. J. Metallocene Interactions with DNA and DNA-Processing Enzymes. Metal Ions in Biological Systems; Marcel Dekker: New York, 1996; pp 53-85.
32. 2 with calf thymus DNA. FEBS Lett. 1993, 322, 291-294.
33. Hotze, A. C. G.; Bacac, M.; Velders, A. H.; Jansen, B. A. J.; Kooijman, H.; Spek, A. L.; Haasnoot, J. G.; Reedjik, J. New Cytotoxic and Water-Soluble Bis(2-phenylazopyridine)ruthenium(II) Complexes. J. Med. Chem. 2003, 46, 1743-1750.
34. Romerosa, A.; Bergamini, P.; Bertolasi, V.; Canella, A.; Cattabriga, M.; Gavioli, R.; Manas, S.; Mantovani, N.; Pellacani, L. Biologically Active Platinum Complexes Containing 8-Thiotheophylline and 8-(Methylthio)theophylline. Inorg. Chem. 2004, 43, 905-913.
35. Mosmann, T. Rapid Colorimetric Assay for Cellular Growth and Survival: Application to Proliferation and Cytotoxicity Assays. J. Immunol. Methods 1983, 65, 55-63.
36. Tada, H.; Shiho, O.; Kuroshima, K.-I.; Koyama, M.; Tsukamoto, K. An improved colorimetric assay for interleukin 2. J. Immunol. Methods 1986, 93, 157-165.
37. Köpf-Maier, P.; Wagner, W.; Köpf, H. In Vitro Cell Growth Inhibition by Metallocene Dichlorides. Cancer Chemother. Pharmacol. 1981, 5, 237-241.
38. Köpf-Maier, P.; Köpf, H. Transition and Main-Group Metal Cyclopentadienyl Complexes: Preclinical Studies on a Series of Antitumor Agents of Different Structural Types. Struct. Bonding 1988, 70, 103-194.
39. Köpf-Maier, P.; Leitner, M.; Voigtländer, R.; Köpf, H. Molybdocene Dichloride as an Antitumor Agent. Z. Naturforsch. 1979, 34c, 1174-1176.
40. Balzarek, C.; Weakley, T. J. R.; Kuo, L. Y.; Tyler, D. R. Investigation of the monomer-dimer equilibria of molybdocenes in water. Organometallics 2000, 19, 2927-2931.
41. Allen, O. R.; Croll, L.; Gott, A. L.; Knox, R. J.; McGowan, P. C. Functionalozed Cyclopentadienyl Tiatnium Organometallic Compounds as New Antitumor Drugs. Organometallics 2004, 23, 288-292.
42. Wu, A.; Kennedy, D. C.; Patrick, B. O.; James, B. R. Ruthenium-(II) Sulfoxide-Maltolato and -Nitroimidazole Complexes: Synthesis and MTT Assay. Inorg. Chem. 2003, 42, 7579-7586.
43. 2]. J. Inorg. Biochem. 2003, 97, 215-220.
44. Ma, D.-L.; Che, C.-M. A Bifunctional Platinum(II) Complex Capable of Intercalation and Hydrogen-Bonding Interactions with DNA: Binding Studies and Cytotoxicity. Chem. Eur. J. 2003, 9, 6133-6144.
45. Reedijk, J. Why Does Cisplatin Reach Guanine-N7 with Competing S-Donor Ligands Available in the Cell? Chem. Rev. 1999, 99, 2499-2510.
46. Glasoe, P. K.; Long, F. A. Use of Glass Electrodes to Measure Acidities in Deuterium Oxide. J. Phys. Chem. 1960, 64, 188-190.
47. Tamborski, C.; Soloski, E. J. Organolithium Intermediates from 1,4-Disubstituted Tetrafluorobenzene Compounds. J. Org. Chem. 1966, 31, 743-745.
48. Fielding, H. C.; Shirley, I. M. Synthesis and reactions of 4-sulfo-2,3,5,6-tetrafluorobenzoic acid. J. Fluor. Chem. 1992, 59, 15-31.
49. Robson, P.; Stacey, M.; Stephens, R.; Tatlow, J. C. Aromatic polyfluoro compounds VI. Penta- and 2,3,5,6-tetrafluorothiophenol. J. Chem. Soc. 1960, 4754-4760.