Skip to main content
SpringerLink
Log in

Titanocenes: Cytotoxic and Anti-angiogenic Chemotherapy Against Advanced Renal-Cell Cancer

  • Chapter
  • First Online:
Medicinal Organometallic Chemistry

Part of the book series: Topics in Organometallic Chemistry ((TOPORGAN,volume 32))

Abstract

6-Substituted fulvenes are interesting and easily accessible starting materials for the synthesis of novel-substituted titanocenes via reductive dimerisation, carbolithiation or hydridolithiation reactions, which are followed by a transmetallation reaction with titanium tetrachloride in the latter two cases. Depending on the substitution pattern, these titanocenes prove to be bioorganometallic anticancer drugs, which have significant potential against advanced or metastatic renal-cell cancer. Patients bearing these stages of kidney cancer have a poor prognosis so far and therefore real progress in the area of metal-based anticancer drugs may come from this simple and effective synthetic approach.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 259.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 329.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 329.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Schilling T, Keppler BK, Heim ME, Niebch G, Dietzfelbinger H, Rastetter J, Hanauske AR (1996) Invest New Drugs 13:327–332

    Article  CAS  Google Scholar 

  2. Melendez E (2002) Crit Rev Oncol Hematol 42:309–315

    Article  Google Scholar 

  3. Köpf H, Köpf-Maier P (1979) Angew Chem Int Ed Engl 18:477–478

    Article  Google Scholar 

  4. Caruso F, Rossi M (2004) Met Ions Biol Syst 42:353–384

    CAS  Google Scholar 

  5. Lummen G, Sperling H, Luboldt H, Otto T, Rubben H (1998) Cancer Chemother Pharmacol 42:415–417

    Article  CAS  Google Scholar 

  6. Kröger N, Kleeberg UR, Mross K, Edler L, Saβ G, Hossfeld D (2000) Onkol 23:60–62

    Article  Google Scholar 

  7. Allen OR, Croll L, Gott AL, Knox RJ, McGowan PC (2004) Organometallics 23:288–292

    Article  CAS  Google Scholar 

  8. Causey P, Baird M (2004) Organometallics 23:4486–4494

    Article  CAS  Google Scholar 

  9. Meyer R, Brink S, van Rensburg C, Jooné G, Görls H, Lotz S (2005) J Organomet Chem 690:117–125

    Article  CAS  Google Scholar 

  10. Stone KJ, Little RD (1984) J Org Chem 49:1849–1853

    Article  CAS  Google Scholar 

  11. Mosmann T (1983) J Immunol Methods 65:55–63

    Article  CAS  Google Scholar 

  12. Strohfeldt K, Tacke M (2008) Chem Soc Rev 37:1174–1187

    Article  CAS  Google Scholar 

  13. Sweeney NJ, Mendoza O, Müller-Bunz H, Pampillón C, Rehmann F-JK, Strohfeldt K, Tacke M (2005) J Organomet Chem 690:4537–4544

    Article  CAS  Google Scholar 

  14. Sweeney NJ, Gallagher WM, Müller-Bunz H, Pampillón C, Strohfeldt K, Tacke M (2006) J Inorg Biochem 100:1479–1486

    Article  CAS  Google Scholar 

  15. Erker G, Nolte R, Aul R, Wilker S, Krüger C, Noe R (1991) J Am Chem Soc 113:7594–7602

    Article  CAS  Google Scholar 

  16. Leblanc JC, Moise C (1976) J Organomet Chem 120:65–71

    Article  CAS  Google Scholar 

  17. Sweeney NJ, Claffey J, Müller-Bunz H, Pampillón C, Strohfeldt K, Tacke M (2007) Appl Organomet Chem 21:57–62

    Article  CAS  Google Scholar 

  18. Strohfeldt K, Müller-Bunz H, Pampillón C, Sweeney NJ, Tacke M (2006) Eur J Inorg Chem 4621–4628

    Google Scholar 

  19. Strohfeldt K, Müller-Bunz H, Pampillón C, Sweeney NJ, Tacke M (2007) Trans Met Chem 32:971–980

    Article  CAS  Google Scholar 

  20. Claffey J, Gleeson B, Hogan M, Müller-Bunz H, Wallis D, Tacke M (2008) Eur J Inorg Chem 4074–4082

    Google Scholar 

  21. Claffey J, Hogan M, Müller-Bunz H, Pampillón C, Tacke M (2008) ChemMedChem 3:729–731

    Article  CAS  Google Scholar 

  22. Pampillón C, Claffey J, Strohfeldt K, Tacke M (2008) Eur J Med Chem 43:122–128

    Article  Google Scholar 

  23. Pampillón C, Sweeney NJ, Strohfeldt K, Tacke M (2007) J Organomet Chem 692:2153–2159

    Article  Google Scholar 

  24. Pampillón C, Claffey J, Hogan M, Tacke M (2007) Z Allg Anorg Chem 633:1695–1700

    Article  Google Scholar 

  25. Hogan M, Claffey J, Pampillón C, Tacke M (2008) Med Chem 4:91–99

    Article  CAS  Google Scholar 

  26. Pampillón C, Claffey J, Hogan M, Strohfeldt K, Tacke M (2007) Trans Met Chem 32:434–441

    Article  Google Scholar 

  27. Hogan M, Cotter J, Claffey J, Gleeson B, Wallis D, O’Shea D, Tacke M (2008) Helv Chim Acta 91:1787–1797

    Article  CAS  Google Scholar 

  28. Hogan M, Claffey J, Pampillón C, Watson RWG, Tacke M (2007) Organometallics 26:2501–2506

    Article  CAS  Google Scholar 

  29. Hickey T, Claffey J, Fitzpatrick E, Hogan M, Pampillón C, Tacke M (2007) Invest New Drugs 25:425–433

    Article  CAS  Google Scholar 

  30. Suzuka T, Ogasawara M, Hayashi T (2002) J Org Chem 67:3355–3359

    Article  CAS  Google Scholar 

  31. Pampillón C, Claffey J, Hogan M, Tacke M (2008) Biometals 21:197–204

    Article  Google Scholar 

  32. Pampillón C, Sweeney N, Strohfeldt K, Tacke M (2006) Inorg Chim Acta 359:3969–3975

    Article  Google Scholar 

  33. Pampillón C, Mendoza O, Sweeney N, Strohfeldt K, Tacke M (2006) Polyhedron 25:2101–2108

    Article  Google Scholar 

  34. Kelter G, Sweeney NJ, Strohfeldt K, Fiebig H-H, Tacke M (2005) Anticancer Drugs 16:1091–1098

    Article  CAS  Google Scholar 

  35. Oberschmidt O, Hanauske AR, Rehmann F-JK, Strohfeldt K, Sweeney NJ, Tacke M (2005) Anticancer Drugs 16:1071–1073

    Article  CAS  Google Scholar 

  36. Valaderes MC, Ramos AL, Rehmann F-JK, Sweeney NJ, Strohfeldt K, Tacke M, Queiroz MLS (2006) Eur J Pharmacol 534:264–270

    Article  Google Scholar 

  37. O’Connor K, Gill C, Tacke M, Rehmann F-JK, Strohfeldt K, Sweeney N, Fitzpatrick JM, Watson RWG (2006) Apoptosis 11:1205–1214

    Article  Google Scholar 

  38. Oberschmidt O, Hanauske AR, Pampillón C, Sweeney NJ, Strohfeldt K, Tacke M (2007) Anticancer Drugs 18:317–321

    Article  CAS  Google Scholar 

  39. Fichtner I, Pampillón C, Sweeney NJ, Strohfeldt K, Tacke M (2006) Anticancer Drugs 17:333–336

    Article  CAS  Google Scholar 

  40. Bannon JH, Fichtner I, O’Neill A, Pampillon C, Sweeney NJ, Strohfeldt K, Watson RW, Tacke M, Mc Gee MM (2007) Br J Cancer 97:1234–1241

    Article  CAS  Google Scholar 

  41. Dowling CM, Claffey J, Cuffe S, Fichtner I, Pampillón C, Sweeney NJ, Strohfeldt K, Watson RWG, Tacke M (2008) Lett Drug Des Discov 5:141–144

    Article  CAS  Google Scholar 

  42. Vessières A, Plamont M-A, Cabestaing C, Claffey J, Dieckmann S, Hogan M, Müller-Bunz H, Strohfeldt K, Tacke M (2009) J Organomet Chem 694:874–877

    Article  Google Scholar 

  43. Gunda Köllensperger, personal communication

    Google Scholar 

  44. Erxleben A, Claffey J, Tacke M (2010) J Inorg Biochem 104:390–396

    Google Scholar 

  45. Tacke M (2008) Lett Drug Des Discov 5:332–335

    Article  CAS  Google Scholar 

  46. Beckhove P, Oberschmidt O, Hanauske AR, Pampillón C, Schirrmacher V, Sweeney NJ, Strohfeldt K, Tacke M (2007) Anticancer Drugs 18:311–315

    Article  CAS  Google Scholar 

  47. Weber H, Claffey J, Hogan M, Pampillón C, Tacke M (2008) Toxicol In Vitro 22:531–534

    Article  CAS  Google Scholar 

  48. Fichtner I, Claffey J, Gleeson B, Hogan M, Wallis D, Weber H, Tacke M (2008) Lett Drug Des Discov 5:489–493

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Conway Institute of Biomolecular and Biomedical Research, Centre for Synthesis and Chemical Biology, UCD School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland

    Megan Hogan & Matthias Tacke

Authors
  1. Megan Hogan
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Matthias Tacke
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Matthias Tacke .

Editor information

Editors and Affiliations

  1. Chimie de Paris (ENSCP), Ecole Nationale Superieure de, rue Pierre et Marie Curie 11, Paris CX 05, 75231, France

    Gérard Jaouen

  2. LS für Anorganische Chemie I -, Bioanorganische Chemie, Universität Bochum, Universitätsstr. 150, Bochum, 44801, Germany

    Nils Metzler-Nolte

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Hogan, M., Tacke, M. (2010). Titanocenes: Cytotoxic and Anti-angiogenic Chemotherapy Against Advanced Renal-Cell Cancer. In: Jaouen, G., Metzler-Nolte, N. (eds) Medicinal Organometallic Chemistry. Topics in Organometallic Chemistry, vol 32. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-13185-1_5

Download citation

Publish with us

Policies and ethics

Search

Navigation