Organometallic anticancer agents. 2. Aqueous chemistry and interaction of niobocene dichloride with nucleic acid constituents and amino acids

Journal of Medicinal Chemistry

Volumn 39, Issue 25, 1996, Pages 5012-5016

  Harding, Margaret M ^a   Prodigalidad, Michael ^a   Lynch, Mark J ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTINEOPLASTIC AGENT; GLUTAMIC ACID; HISTIDINE; NIOBIUM; NIOBOCENE DICHLORIDE; NUCLEIC ACID; NUCLEOSIDE; NUCLEOTIDE; ORGANOMETALLIC COMPOUND; RIBOSE PHOSPHATE; SERINE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG MECHANISM; DRUG SOLUBILITY; DRUG STRUCTURE; HYDROLYSIS; OXIDATION; PH; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; TITRIMETRY;

AMINO ACIDS; ANTINEOPLASTIC AGENTS; CYCLOPENTANES; NUCLEIC ACIDS; ORGANOMETALLIC COMPOUNDS; WATER;

EID: 0029731763     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9603678     Document Type: Article

References (30)

1. Köpf-Maier, P.; Köpf, H. Metallocene Complexes: Organometallic Antitumor Agents. Drugs Future 1986, 11, 297-319 and references therein.
2. Köpf-Maier, P.; Köpf, H. Transition and Main-Group Metal Cyclopentadienyl Complexes: Preclinical Studies on a Series of Antitumor Agents of Different Structural Type. Struct. Bonding (Berlin) 1988, 70, 105-185 and references therein.
3. Köpf-Maier, P.; Leitner, M.; Köpf, H. Tumor Inhibition by Metallocenes: Antitumor Activity of Niobocene and Tungstocene Dichlorides. J. Inorg. Nucl. Chem. 1980, 42, 1789-1791.
4. (a) Köpf-Maier, P.; Köpf, H. Tumor Inhibition by Titanocene Bichloride: First Clues to the Mechansim of Action. Naturwissenschaften 1980, 67, 415-416.
5. (b) Köpf-Maier, P; Köpf, H.; Wagner, W. In vitro Cell Growth Inhibition by Metallocene Dichlorides. Cancer Chemother. Pharmacol. 1981, 5, 237-241.
6. (c) Köpf-Maier, P.; Wagner, W.; Hesse, B.; Köpf, H. Tumor Inhibition by Metallocenes: Activity against Leukemias and Detection of the Systemic Effect. Eur. J. Cancer 1981, 17, 665-669.
7. (d) Köpf-Maier, P; Grabowski, S.; Liegener, J.; Köpf, H. New Antitumor Titanocene Derivatives Containing Hydrophilic Ligands. Inorg. Chim. Acta 1985, 108, 99-103.
8. (e) Murthy, M. S.; Rao, L. N.; Kuo, L. Y.; Toney, J. H.; Marks, T. J. Antitumor and Toxicologic Properties of the Organometallic Anticancer Agent Vanadocene Dichloride. Inorg. Chim. Acta 1988, 152, 117-124.
9. Berdel, W. E.; Schmoll, H. J.; Scheulen, M. E.; Korfel, A.; Knoche, M. F.; Harstrci, A.; Bach, F.; Baumgart, J, Sass, G. Phase I Clinical Trial of Titanocene Dichloride in Adults with Advanced Solid Tumours. J. Cancer Res. Clin. Oncol. 1994, 120 [Suppl.], R172.
10. Sudquist, W. I.; Lippard, S. J. The Coordination Chemistry of Platinum Anticancer Drugs and Related Compounds with DNA. Coord. Chem. Rev. 1990, 100, 293-322.
11. (a) Köpf-Maier, P.; Krahl, D. Tumor Inhibition by Metallocenes: Ultrastructural Localization of Titanium and Vanadium in Treated Tumor Cells by Electron Loss Spectrsoscopy. Chem. Biol. Interact. 1983, 44, 317-328.
12. (b) Köpf-Maier, P.; Köpf, H. Intracellular Distribution of Titanium after Treatment with the Antitumor Agent Titanocene Dichloride: an Electron Energy Loss Spectroscopic Study. Naturwissenschaften 1981, 68, 273-274.
13. McLaughlin, M. L.; Cronan, J. M., Jr.; Schaller, T. R.; Sneller, R. D. DNA-Metal Binding Antitumor-Active Metallocene Dichlorides from Inductively Coupled Plasma Spectroscopy Analysis: Titanocene Dichloride Forms DNA-CpTi Adducts Depending on pH. J. Am. Chem. Soc. 1990, 112, 8949-8952.
14. 2 with Calf Thymus DNA. FEBS Lett. 1993, 322, 291-294.
15. 2 Nucleotide/Nucleobase Aqueous Coordination Chemistry. J. Am. Chem. Soc. 1987, 109, 7207-7209.
16. 2, with Nucleotides and Phosphoesters. Mechanistic Implications for a New Class of Antitumor Agents. J. Am. Chem. Soc. 1986, 108, 7263-7274.
17. (c) Kuo, L. Y.; Kanatzidis, M. G.; Sabat, M.; Tipton, L.; Marks, T. J. Metallocene Antitumor Agents. Solution and Solid-State Molybdocene Coordination Chemistry of DNA Constituents. J. Am. Chem. Soc. 1991, 113, 9027-9045.
18. Murray, J. H.; Harding, M. M. Organometallic Anticancer Agents: The Effect of the Central Metal and Halide Ligands on the Interaction of Metallocene Dihalides with Nucleic Acid Constituents. J. Med. Chem. 1994, 37, 1936-1941.
19. Köpf-Maier, P.; Klapötke, T. M.; Antitumor Activity of Ionic Niobocene and Molybdocene Complexes in High Oxidation States. J. Cancer Res. Clin. Oncol. 1992, 118, 216-221.
20. (a) Dahl, L. F.; Wauper, D. L. The Crystal Structure of α-Niobium Tetraiodide. Acta Crystallogr. 1962, 15, 903-911.
21. (b) Elson, I. H.; Kochi, J. K. Interaction of Paramagnetic Niobium(IV) Hydrides with Olefins. Electron Spin Resonance Studies of Metastable Intermediates. J. Am. Chem. Soc. 1975, 97, 1262-1265.
22. 2NbI3. J. Organomet. Chem. 1968, 12, 479-484.
23. Compton, R. G.; Eklund, J. C.; Page, S. D.; Rebbitt, T. O. Sonoelectrochemistry: the Oxidation of Bis(cylopentadiene)-molybdenum Dichloride. J. Chem. Soc., Dalton Trans. 1995, 389-93.
24. Douglas, W. E.; Green, M. L. H. Transition Metal Complexes as Ligands: Preparation of Mixed Transition Metal Complexes of Niobium with Nickel, Palladium, Platiunum, or Molybdenum. J. Chem. Soc., Dalton Trans. 1972, 1796-1800.
25. 2 as a Ligand. J. Am. Chem. Soc. 1968, 90, 1745-1746.
26. (b) Wilkinson, G.; Birmingham, J. M. Bis-cyclopentadienyl Compounds of Ti, Zr, V, Nb and Ta. J. Am. Chem. Soc. 1964, 76, 4281-4284.
27. (c) Prout, K.; Cameron, T. S.; Forder, R. A.; Critchley, S. R.; Denton, R.; Rees, G. V. The Crystal and Molecular Structures of Bent Bis-p-cyclopentadienyl-Metal Complexes. Acta Crystallogr. 1974, B30, 2290-2304.
28. (a) Klapötke, T. M.; Köpf, H.; Tornieporth-Oetting, I. C. Synthesis, Characterization, and Structural Investigation of the First Bioinorganic Titanocene(IV) α-Amino Acid complexes Prepared from the Antitumor Agent Titanocene Dichloride. Organometallics 1994, 13, 3628-3633.
29. (b) Tornieporth-Oetting,I. C; White, P. S. Ionic Titanocene(IV) α-Amino Acid Complexes of DL-Phenylalanine and DL-4-Fluorophenylalanine: Synthesis, Characterization, and Investigation of the Antimicrobial Behavior towards Escherichia coli. Organometallics 1995, 14, 1632-1636.
30. McLaughlin, M. L.; Cronan, J. M., Jr.; Schaller, T. R.; Sneller, R. D. DNA-Metal Binding Antitumor-Active Metallocene Dichlorides from Inductively Coupled Plasma Spectroscopy Analysis: Titanocene Dichloride Forms DNA-CpTi Adducts Depending on pH. J. Am. Chem. Soc. 1990, 112, 8949-8952.