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Chemical Compound Review

NSC-78453     cyclopenta-1,3-diene; dichlorotitanium

Synonyms: NSC78453, WLN: L50J 0-TI-GG- 0L50J, Dichlorodi-.pi.-cyclopentadienyltitanium, Bis(.pi.-cyclopentadienyl)dichlorotitanium, Dichlorobis(.pi.-cyclopentadienyl)titanium, ...
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Disease relevance of Titanocene dichloride


High impact information on Titanocene dichloride

  • Phase I trial of weekly scheduling and pharmacokinetics of titanocene dichloride in patients with advanced cancer [6].
  • The mechanism of titanocene mediated 3-exo cyclizations was investigated by a combined theoretical and experimental study [7].
  • The titanocene silyl hydride complexes [Ti(Cp)(2)(PMe(3))(H)(SiR(3))] [SiR(3)=SiMePhCl (6), SiPh(2)Cl (7), SiMeCl(2) (8), SiCl(3) (9)] were prepared by HSiR(3) addition to [Ti(Cp)(2)(PMe(3))(2)] and were studied by NMR and IR spectroscopy, X-ray diffraction (for 6, 8, and 9), and DFT calculations [8].
  • Ti(IV) uptake and release by human serum transferrin and recognition of Ti(IV)-transferrin by cancer cells: understanding the mechanism of action of the anticancer drug titanocene dichloride [9].
  • Detailed knowledge of the mechanism of hydrolysis of titanocene dichloride and its stability in the infusion liquid is a prerequisite for clinical tests and for a successful application for permission as medication [10].

Chemical compound and disease context of Titanocene dichloride


Biological context of Titanocene dichloride

  • Titanocene dichloride induced a block in late S/early G2 phase of the cell cycle; however apoptotic cell death occurred from any phase of cycle [1].
  • Treatment of these animals with TITANOCENE X (2.5-50 mg/kg/day) produced an increase in myelopoiesis, in a dose-dependent manner, and reduced spleen colony formation [14].
  • All three complexes undergo clean and facile hydrogenation at 23 degrees C, yielding the titanocene hydroxy hydride complexes (eta5-C5Me4R)2Ti(OH)H [15].
  • Gas-phase photoelectron spectroscopy and density functional theory have been utilized to investigate the interactions between the p orbitals of dithiolate ligands and d orbitals of titanium in bent titanocene complexes as minimum molecular models of active site features of pyranopterin Mo/W enzymes [16].
  • The experimental antitumor agent titanocene dichloride inhibited collagenase type IV from Walker 256 carcinosarcoma with IC50 approximately 0.2 mM [17].

Anatomical context of Titanocene dichloride


Associations of Titanocene dichloride with other chemical compounds


Gene context of Titanocene dichloride


Analytical, diagnostic and therapeutic context of Titanocene dichloride


  1. Anti-proliferative activity and mechanism of action of titanocene dichloride. Christodoulou, C.V., Eliopoulos, A.G., Young, L.S., Hodgkins, L., Ferry, D.R., Kerr, D.J. Br. J. Cancer (1998) [Pubmed]
  2. Tumor inhibition by titanocene complexes: influence on xenografted human adenocarcinomas of the gastrointestinal tract. Köpf-Maier, P. Cancer Chemother. Pharmacol. (1989) [Pubmed]
  3. Phase II trial of titanocene dichloride in advanced renal-cell carcinoma. Lümmen, G., Sperling, H., Luboldt, H., Otto, T., Rübben, H. Cancer Chemother. Pharmacol. (1998) [Pubmed]
  4. Pattern of toxicity by titanocene dichloride in mice. Blood and urine chemical parameters. Köpf-Maier, P., Gerlach, S. J. Cancer Res. Clin. Oncol. (1986) [Pubmed]
  5. Immunologic response to the treatment of Ehrlich ascites tumor with titanocene dichloride. Köpf-Maier, P., Hesse, A. J. Cancer Res. Clin. Oncol. (1984) [Pubmed]
  6. Phase I trial of weekly scheduling and pharmacokinetics of titanocene dichloride in patients with advanced cancer. Christodoulou, C.V., Ferry, D.R., Fyfe, D.W., Young, A., Doran, J., Sheehan, T.M., Eliopoulos, A., Hale, K., Baumgart, J., Sass, G., Kerr, D.J. J. Clin. Oncol. (1998) [Pubmed]
  7. A combined theoretical and experimental study of efficient and fast titanocene-catalyzed 3-exo cyclizations. Friedrich, J., Dolg, M., Gansäuer, A., Geich-Gimbel, D., Lauterbach, T. J. Am. Chem. Soc. (2005) [Pubmed]
  8. Nonclassical titanocene silyl hydrides. Ignatov, S.K., Rees, N.H., Tyrrell, B.R., Dubberley, S.R., Razuvaev, A.G., Mountford, P., Nikonov, G.I. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  9. Ti(IV) uptake and release by human serum transferrin and recognition of Ti(IV)-transferrin by cancer cells: understanding the mechanism of action of the anticancer drug titanocene dichloride. Guo, M., Sun, H., McArdle, H.J., Gambling, L., Sadler, P.J. Biochemistry (2000) [Pubmed]
  10. Determination of titanocene, a new drug with anticancer potential, and its metabolism in solution by capillary electrophoresis. Wittrisch, H., Schröer, H.P., Vogt, J., Vogt, C. Electrophoresis (1998) [Pubmed]
  11. Glucocorticoid induction of cleft palate after treatment with titanocene dichloride? Köpf-Maier, P. Toxicology (1985) [Pubmed]
  12. Effects of vinorelbine and titanocene dichloride on human tumour xenografts in nude mice. Friedrich, M., Villena-Heinsen, C., Farnhammer, C., Schmidt, W. Eur. J. Gynaecol. Oncol. (1998) [Pubmed]
  13. Activity of titanocene dihalides against a human colon carcinoma heterotransplanted to athymic mice. Köpf-Maier, P., Moormann, A., Köpf, H. European journal of cancer & clinical oncology. (1985) [Pubmed]
  14. Antitumour activity of [1,2-di(cyclopentadienyl)-1,2-di(p-N,N-dimethylaminophenyl)-ethanediyl] titanium dichloride in xenografted Ehrlich's ascites tumour. Valadares, M.C., Ramos, A.L., Rehmann, F.J., Sweeney, N.J., Strohfeldt, K., Tacke, M., Queiroz, M.L. Eur. J. Pharmacol. (2006) [Pubmed]
  15. Dihydrogen and Silane Addition to Base-Free, Monomeric Bis(cyclopentadienyl)titanium Oxides. Hanna, T.E., Lobkovsky, E., Chirik, P.J. Inorganic chemistry (2007) [Pubmed]
  16. Electronic structure of bent titanocene complexes with chelated dithiolate ligands. Cooney, J.J., Cranswick, M.A., Gruhn, N.E., Joshi, H.K., Enemark, J.H. Inorganic chemistry. (2004) [Pubmed]
  17. Inhibition of angiogenesis by anthracyclines and titanocene dichloride. Maragoudakis, M.E., Peristeris, P., Missirlis, E., Aletras, A., Andriopoulou, P., Haralabopoulos, G. Ann. N. Y. Acad. Sci. (1994) [Pubmed]
  18. The effect of a Titanocene Dichloride derivative, Ti IV (C5H5)(2) NCS(2), on the haematopoietic response of Ehrlich tumour-bearing mice. Valadares, M.C., Queiroz, M.L. Eur. J. Pharmacol. (2002) [Pubmed]
  19. Suppression of angiogenesis by the antitumor agent titanocene dichloride. Bastaki, M., Missirlis, E., Klouras, N., Karakiulakis, G., Maragoudakis, M.E. Eur. J. Pharmacol. (1994) [Pubmed]
  20. Intracellular localization of titanium within xenografted sensitive human tumors after treatment with the antitumor agent titanocene dichloride. Köpf-Maier, P. J. Struct. Biol. (1990) [Pubmed]
  21. Titanium(IV) targets phosphoesters on nucleotides: implications for the mechanism of action of the anticancer drug titanocene dichloride. Guo, M., Guo, Z., Sadler, P.J. J. Biol. Inorg. Chem. (2001) [Pubmed]
  22. Anti-tumor activity of Titanocene Y in xenografted Caki-1 tumors in mice. Fichtner, I., Pampillón, C., Sweeney, N.J., Strohfeldt, K., Tacke, M. Anticancer Drugs (2006) [Pubmed]
  23. Different inhibition pattern of the nucleic acid metabolism after in vitro treatment with titanocene and vanadocene dichlorides. Köpf-Maier, P., Wagner, W., Köpf, H. Naturwissenschaften (1981) [Pubmed]
  24. Quantitative analysis of dimethyl titanocene by iodometric titration, gas chromatography and NMR. Vailaya, A., Wang, T., Chen, Y., Huffman, M. Journal of pharmaceutical and biomedical analysis. (2001) [Pubmed]
  25. Tumor inhibition by titanocene complexes. Activity against B16 melanoma and colon 38 carcinoma. Köpf-Maier, P., Köpf, H. Arzneimittel-Forschung. (1987) [Pubmed]
  26. Relationship between chemotherapy with paclitaxel, cisplatin, vinorelbine and titanocene dichloride and expression of proliferation markers and tumour suppressor gene p53 in human ovarian cancer xenografts in nude mice. Kolberg, H.C., Villena-Heinsen, C., Deml, M.M., Kraemer, S., Diedrich, K., Friedrich, M. Eur. J. Gynaecol. Oncol. (2005) [Pubmed]
  27. Antitumour metallocenes: structure-activity studies and interactions with biomolecules. Harding, M.M., Mokdsi, G. Current medicinal chemistry. (2000) [Pubmed]
  28. Preparation, biodistribution, and small animal PET of 45Ti-transferrin. Vavere, A.L., Welch, M.J. J. Nucl. Med. (2005) [Pubmed]
  29. Human ovarian cancer xenografts in nude mice: chemotherapy trials with paclitaxel, cisplatin, vinorelbine and titanocene dichloride. Villena-Heinsen, C., Friedrich, M., Ertan, A.K., Farnhammer, C., Schmidt, W. Anticancer Drugs (1998) [Pubmed]
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