Skip to main content
Log in

Antitumor activities of ferrocene compounds

  • Reviews
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Data on the antitumor activities of ferrocene compounds and the results concerning the mechanisms of their action published between 1995 and 2010 are discussed. The biomedical aspects of the study of ferrocene derivatives are briefly analyzed.

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

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. M. D. Mashkovskii, Lekarstvennye sredstva [Pharmaceuticals] Meditsina, Moscow, 1993, 2

    Google Scholar 

  2. VIDAL’ Handbook Lekarstvennye preparaty v Rossii [Pharmaceuticals in Russia], 6th edition, AstraFarmServis, Moscow, 2000

    Google Scholar 

  3. D. A. Kharkevich, Farmakologiya, Geotar Meditsina, Moscow, 2000, p. 582 (in Russian).

    Google Scholar 

  4. P. N. Magee, E. Faber, Biochem. J., 1962, 83, 114.

    CAS  Google Scholar 

  5. K. Y. Lee, W. Lijinsky, J. Nat. Cancer Inst., 1966, 37, 401.

    CAS  Google Scholar 

  6. P. F. Swan, P. N. Magee, Biochem. J., 1971, 125, 841.

    Google Scholar 

  7. E. C. Miller, J. A. Miller, Ann. N.Y. Acad. Sci., 1969, 163, 731.

    Article  CAS  Google Scholar 

  8. M. M. Vilenchik, Zakonomernosti moleculeyarno-geneticheskogo deistviya kantserogennykh uglevodorodov [Characteristic Features of the Molecular Genetic Action of Carcinogenic Hydrocarbons], Nauka, Moscow, 1977 (in Russian).

    Google Scholar 

  9. H. Sigel, J. Am. Chem. Soc., 1975, 97, 3209.

    Article  CAS  Google Scholar 

  10. D. K. Granner, Organization and Replication of DNA, in R. K. Murray, D. K. Granner, P. A. Mayes, V. W. Rodwell, Harper’s Biochemistry, Appleton & Lange, Norwalk-Connecticut-San Mateo-California, 21nd ed., 1988.

    Google Scholar 

  11. E. Farber, Cancer Res., 1970, 33, 2537.

    Google Scholar 

  12. H. W. Thielman, Eur. J. Biochem., 1976, 61, 501.

    Article  Google Scholar 

  13. M. A. Girgis, Compt. Rend. Acad. Sci., 1967, D-265, 245.

    Google Scholar 

  14. Ya. G. Erenpreis, Arkhiv patalogich. anatomii i gistologii [Pathology and Histology Archive], 1972, 34, 31 (in Russian).

    Google Scholar 

  15. Yu. S. Larin, Dokl. Akad. Nauk SSSR, 1969, 184, 701 [Dokl. Chem. (Engl. Transl.), 1969].

    Google Scholar 

  16. V. N. Babin, A. V. Dubinin, P. M. Raevskii, A. F. Sviridov, A. L. Sherman, Model’ khimicheskogo carcinogeneza (molekulyarnye aspekty) [Chemical Carcinogenesis Model (Molecular Aspects)], in Modeli. Algoritmy. Prinyatie reshenii, Nauka, Moscow, 1979, p. 153 (in Russian).

    Google Scholar 

  17. P. Köpf-Maier, H. Köpf, E. W. Neuse, Angew. Chem., 1984, 96, 446; Angew. Chem., Int. Ed., 1984, 23, 456

    Article  Google Scholar 

  18. P. Köpf-Maier, H. Köpf, E. W. Neuse, J. Cancer. Res. Clin. Oncol., 1984, 108, 336

    Article  Google Scholar 

  19. P. Köpf-Maier, H. Köpf, E. W. Neuse, Ger. Offen, DE, 1985, No. 3403443.

  20. L. V. Popova (Snegur), V. N. Babin, Yu. A. Belousov, Yu. S. Nekrasov, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, O. B. Bychenko, P. M. Raevskii, N. B. Morozova, A. I. Ilyina, K. G. Shitkov, Appl. Organomet. Chem., 1993, 7, 85

    Article  CAS  Google Scholar 

  21. L. V. Snegur, Yu. S. Nekrasov, V. V. Gumenyuk, N. B. Morozova, Zh. V. Zhilina, I. K. Sviridova, I. A. Rodina, N. S. Sergeeva, K. G. Shchitkov, V. N. Babin, Ross. Khim. Zhurn., 1998, 42, 178 [Mendeleev Chem. J. (Engl. Transl.), 1998, 42, 151]

    CAS  Google Scholar 

  22. Yu. S. Nekrasov, Zh. V. Zhilina, V. V. Gumenyuk, L. V. Snegur, N. S. Sergeeva, V. N. Babin, Ross. Khim. Zhurn., 1997, 41, 117 [Mendeleev Chem. J. (Engl. Transl.), 1999, 41, 172].

    CAS  Google Scholar 

  23. K. G. Shchitkov, L. V. Snegur, N. B. Morozova, A. I. Il’ina, V. N. Babin, V. I. Borisov, I. G. Rusakov, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, RF Pat. No. 2098096, 1993

  24. L. V. Snegur, V. N. Babin, N. V. Polyakova, V. I. Boev, A. F. Kolomiets, Yu. S. Nekrasov, K. G. Shchitkov, A. A. Pankratov, N. B. Morozova, A. I. Il’ina, RF Pat. No. 2089507, 1996.

  25. L. V. Snegur, A. A. Simenel, Yu. S. Nekrasov, E. A. Morozova, Z. A. Starikova, S. M. Peregudova, Yu. V. Kuzmenko, V. N. Babin, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, J. Organomet. Chem., 2004, 689, 2473

    Article  CAS  Google Scholar 

  26. L. V. Snegur, Yu. S. Nekrasov, N. S. Sergeeva, Zh. V. Zhilina, V. V. Gumenyuk, Z. A. Starikova, A. A. Simenel, N. B. Morozova, I. K. Sviridova, V. N. Babin, Appl. Organomet. Chem., 2008, 22, 139

    Article  CAS  Google Scholar 

  27. A. A. Simenel, S. V. Samarina, L. V. Snegur, Z. A. Starikova, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, Appl. Organomet. Chem., 2008, 22, 276

    Article  CAS  Google Scholar 

  28. A. A. Simenel, E. A. Morozova, L. V. Snegur, S. I. Zykova, V. V. Kachala, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, Appl. Organomet. Chem., 2009, 23, 219

    Article  CAS  Google Scholar 

  29. A. A. Simenel, G. A. Dokuchaeva, L. V. Snegur, A. N. Rodionov, M. M. Ilyin, S. I. Zykova, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, V. A. Rikova, Appl. Organomet. Chem., 2011, 25, 70.

    Article  CAS  Google Scholar 

  30. R. Kovjazin, T. Eldar, M. Patya, A. Vanichkin, H. M. Lander, A. Novogrodsky, FASEB J., 2003, 17, 467.

    CAS  Google Scholar 

  31. G. Jaouen, S. Top, A. Vessières, G. Leclercq, M. J. McGlinchey, Curr. Med. Chem., 2004, 11, 2505

    CAS  Google Scholar 

  32. A. Vessiires, S. Top, W. Beck, E. Hillard, G. Jaouen, Dalton Trans., 2006, 529

  33. M. Gormen, D. Plaïuk, P. Pigeon, E. A. Hillard, M. -A. Plamont, S. Top, A. Vessiires, G. Jaouen, Tetrahedron Lett., 2010, 51, 118.

    Article  CAS  Google Scholar 

  34. K. E. Dombrovski, W. Baldwin, J. E. Sheats, J. Organomet. Chem., 1986, 302, 281.

    Article  Google Scholar 

  35. P. Köpf-Maier, H. Köpf, Chem. Rev., 1987, 87, 1137.

    Article  Google Scholar 

  36. J. Haiduc, C. Silvestry, Coord. Chem. Rev., 1990, 99, 253.

    Article  CAS  Google Scholar 

  37. N. Motohashi, R. Meyer, S. R. Gollapudi, K. R. Bhattiprolu, J. Organomet. Chem., 1990, 398, 205.

    Article  CAS  Google Scholar 

  38. V. N. Babin, P. M. Raevskii, K. G. Shchitkov, L. V. Snegur, Yu. S. Nekrasov, Ross. Khim. Zhurn. (Zhurn. Ross. khim. o-va im. D. I. Mendeleeva), 1995, 39, 19 [Mendeleev Chem. J. (Engl. Transl.), 1995, 39, 17].

    CAS  Google Scholar 

  39. E. W. Neuse, J. Inorg. Organomet. Polym. Materials, 2005, 15, 3

    Article  CAS  Google Scholar 

  40. X. Wu, M. L. Go, in Metallotherapeutic Drugs and Metall-Based Diagnostic Agents: The Use of Metals in Medicine, Eds M. Gielen and E. R. T. Tiekink, 2005, John Wiley and Sons, Ltd

  41. Bioorganometallics: Biomolecules, Labeling, Medicine, Ed. G. Jaouen, WILEY-VCH, Weinheim, 2006.

    Google Scholar 

  42. N. S. Kochetkova, V. I. Boev, V. N. Babin, R. B. Materikova, L. V. Popova (Snegur), V. M. Bondareneko, A. s. SSSR 320 212, 1985, No. 1

  43. N. S. Kochetkova, V. I. Boev, L. V. Popova (Snegur), V. N. Babin, Izv. Akad. Nauk SSSR. Ser. Khim., 1985, 1397 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1985, 34, 1278].

    Google Scholar 

  44. L. V. Popova (Snegur), V. N. Babin, R. B. Materikova, V. I. Boev, A. E. Snegireva, N. P. Borodina, G. M. Shaposhnikova, O. B. Bychenko, V IUPAC Symposium on Organo-Metallic Chemistry directed towards Organic Synthesis, OMCOS-V-Italy-Florence, 1989, pS2–28.

  45. B. Rosenberg, L. Van Camp, J. E. Trosko, V. H. Mansour, Nature, 1969, 222, 385.

    Article  CAS  Google Scholar 

  46. T. A. K. Al-Allaf, L. J. Rashan, Appl. Organometal. Chem., 1999, 13, 63.

    Article  CAS  Google Scholar 

  47. F. D. Popp, S. Roth, J. Kirbay, J. Med. Chem., 1963, 6, 83.

    Article  CAS  Google Scholar 

  48. F. D. Popp, J. Pharm. Sci., 1973, 62, 679.

    Article  CAS  Google Scholar 

  49. G. N. Yashchenko, A. A. Shashmurina, G. M. Anoshina, L. A. Gorelova, N. G. Evstigneeva, L. V. Alekseeva, L. B. Radina, Khim.-Farm. Zhurn., 1978, 12, 68 [Pharm.-Chem. J., 1978, 12, 68].

    CAS  Google Scholar 

  50. V. J. Fiorina, R. J. Dubois, S. Brynes, J. Med. Chem., 1978, 21, 393.

    Article  CAS  Google Scholar 

  51. P. Köpf-Maier, Angew. Chem. Int. Ed., 1979, 91, 509.

    Google Scholar 

  52. P. Köpf-Maier, H. Köpf, Z. Naturforsch., 1979, 34c, 805.

    Google Scholar 

  53. P. Köpf-Maier, M. Leitner, R. Voigtlander, H. Köpf, Z. Naturforsch., 1979, 34c, 1174.

    Google Scholar 

  54. P. Köpf-Maier, M. Leitner, H. Köpf, J. Inorg. Nucl. Chem., 1980, 42, 1789.

    Article  Google Scholar 

  55. P. Köpf-Maier, B. Hesse, H. Köpf, J. Cancer. Res. Clin. Oncol., 1980, 96, 43.

    Article  Google Scholar 

  56. P. Köpf-Maier, A. Moorman, H. Köpf, Eur. J. Cancer. Oncol., 1985, 21, 853.

    Article  Google Scholar 

  57. P. Köpf-Maier, Proc. Sem. Tumor Xenografts in Anticancer Drug Devel., Milano, 1986 (cited from Ref. 22).

  58. P. Köpf-Maier, P. Erkenswick, Toxicology, 1984, 33, 171.

    Article  Google Scholar 

  59. P. Köpf-Maier, Toxicology, 1985, 37, 111.

    Article  Google Scholar 

  60. P. Köpf-Maier, P. Funke-Kaiser, Toxicology, 1986, 38, 81.

    Article  Google Scholar 

  61. P. Köpf-Maier, Eur. J. Clin. Pharm., 1994, 47, 1.

    Article  Google Scholar 

  62. M. Tacke, Book of Abstracts, International Conference on Organometallic and Coordination Chemistry, September 2–8, 2008, N. Novgorod, Russia, S18.

  63. K. Strohfeldt, M. Tacke, Chem. Soc. Rev., 2008, 37, 1174.

    Article  CAS  Google Scholar 

  64. O. Oberschmidt, A.-R. Hamauske, C. Pampillun, K. Strohfeldt, N. J. Sweeney, M. Tacke, Anti-Cancer Drugs, 2007, 18, 317

    Article  CAS  Google Scholar 

  65. M. Tacke, Anti-Cancer Drugs, 2007, 18, 311

    Article  Google Scholar 

  66. I. Fichtmer, C. Pampillun, N. J. Sweeney, K. Strohfeldt, M. Tacke, Anti-Cancer Drugs, 2006, 17, 333

    Article  Google Scholar 

  67. G. Kelter, N. Sweeney, K. Strohfeldt, H.-H. Fiebig, M. Tacke, Anti-Cancer Drugs, 2005, 16, 1091.

    Article  CAS  Google Scholar 

  68. S.-C. Chen, J. Organomet. Chem., 1980, 202, 183.

    Article  CAS  Google Scholar 

  69. M. N. Hughes, The Inorganic Chemistry of Biological Processes, John Wiley and Sons, Chichester-New York-Brisbane-Toronto, 2nd ed.

  70. Ferrotseron, USSR Ministry of Medical Industry, Moscow, 24 pp. (in English).

  71. P. Köpf-Maier, H. Köpf, E. W. Neuse, US Pat. No. 4851430, 1989.

  72. N. B. Morozova, L. V. Popova (Snegur), A. I. Il’ina, V. N. Babin, K. G. Shchitkov, V. I. Borisov, I. G. Rusakov, N. I. Dunyakhina, A. E. Snegireva, N. S. Sergeeva, O. I. Skotnikova, N. P. Borodina, G. M. Shaposhnikova, in Khimioterapiya v lechenii onkologicheskikh bol’nykh [Chemotherapy in the Therapy of Cancer Patients], RF Ministry of Health, Moscow, 1993, p. 91 (in Russian).

    Google Scholar 

  73. N. B. Morozova, L. V. Popova (Snegur), A. I. Il’ina, V. N. Babin, K. G. Shchitkov, Yu. S. Nekrasov, V. I. Borisov, I. G. Rusakov, T. K. Kulabukhova, A. E. Snegireva, V. I. Boev, N. S. Sergeeva, O. I. Skotnikova, N. P. Borodina, G. M. Shaposhnikova, RF Pat. No. 2025125, 1991 (in Russian).

  74. A. Houlton, R. M. G. Roberts, J. Silver, J. Organomet. Chem., 1991, 418, 107.

    Article  CAS  Google Scholar 

  75. P. Meunier, I. Ouattara, B. Gautheron, J. Tirouflet, D. Camboli, J. Besancon, F. Boulay, Eur. J. Med. Chem., 1991, 26, 351.

    Article  CAS  Google Scholar 

  76. K. G. Shchitkov, L. V. Popova, N. B. Morozova, V. N. Babin, A. I. Il’ina, I. G. Rusakov, A. E. Snegireva, N. S. Sergeeva, O. I. Skotnikova, N. P. Borodina, V. I. Boev, O. B. Bychenko, G. M. Shaposhnikova, Khimioterapiya v lechenii onkologicheskikh bol’nykh [Chemotherapy in the Therapy of Cancer Patients], RF Ministry of Health, Moscow, 1993, p. 95 (in Russian).

    Google Scholar 

  77. L. V. Snegur, Ph.D. Thesis, A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, 1993 (in Russian).

  78. G. Caldwell, M. G. Meirim, E. W. Neuse, C. E. J. van Rensburg, Appl. Organomet Chem., 1998, 12, 793.

    Article  CAS  Google Scholar 

  79. M. Wenzel, J. Wu, E. Liss, E. W. Neuse, Z. Naturforsch., 1988, 43c, 963.

    Google Scholar 

  80. E. W. Neuse, F. Kanzawa, Appl. Organomet. Chem., 1990, 4, 19.

    Article  CAS  Google Scholar 

  81. E. W. Neuse, Polym. Adv. Technol., 1998, 9, 786.

    Article  CAS  Google Scholar 

  82. M. Wenzel, E. Nipper, W. Klose, J. Nucl. Med., 1977, 18, 367.

    CAS  Google Scholar 

  83. A. Taylor, M. Wenzel, Naturwiss, 1977, 18, 273.

    Article  Google Scholar 

  84. M. Wenzel, M. Scheider, E. Liss, Z. Naturforsch., 1979, 34, 670.

    Google Scholar 

  85. W. H. Ang, P. J. Dyson, Eur. J. Inorg. Chem., 2006, 4003.

  86. A. Nazarov, Ch. Hartinger, B. Keppler, P. Dyson, Appl. Organomet. Chem., 2008, 22, 300.

    Article  Google Scholar 

  87. M. Gras, B. Therrien, G. Süss-Fink, A. Casini, F. Edafe, P. J. Dyson, J. Organomet. Chem., 2010, 695, 1119

    Article  CAS  Google Scholar 

  88. G. Von Poelhsitz, A. L. Bogado, M. P. de Araujo, H. S. Selistre-de-Araújo, J. Ellena, E. E. Castellano, A. A. Batista, Polyhedron, 2007, 26, 4707.

    Article  Google Scholar 

  89. E. W. Neuse, M. C. Meirim, N. F. Bloom, Organometallics, 1988, 7, 2562.

    Article  CAS  Google Scholar 

  90. G. Pilloni, R. Graziani, B. Longato, Inorg. Chim. Acta, 1991, 190, 165.

    Article  CAS  Google Scholar 

  91. D. T. Hill, G. R. Girard, F. L. McCabe, Inorg. Chem., 1989, 28, 3529.

    Article  CAS  Google Scholar 

  92. J. S. Casas, M. V. Castaño, M. C. Cifuentes, J. C. García-Monteagudo, A. Sánchez, J. Sordo, U. Abram, J. Inorg. Biochem., 2004, 98, 1009.

    Article  CAS  Google Scholar 

  93. A. Rosenfeld, J. Blum, D. Gibson, A. Ramu, Inorg. Chim. Acta, 1992, 201, 219.

    Article  CAS  Google Scholar 

  94. H. Tamura, M. Miwa, Chem. Lett., 1997, 1177.

  95. N. M. Emanuel’, Kinetika eksperimental’nykh opukholevykh protsessov [Kinetics of Experimental Tumor Processes], Nauka, Moscow, 1977, 416 pp (in Russian).

    Google Scholar 

  96. D. A. Oparin, V. D. Makhaev, V. D. Vil’chevskaya, T. I. Zimatkina, Zh. V. Motylevich, S. M. Zimatkin, S. V. Zabrodskaya, A. I. Krylova, Yu. Yu. Gorelikova, Khim.-Farm. Zhurn., 1996, 30, 11 [Pharm.-Chem. J., 1996, 30, 11].

    CAS  Google Scholar 

  97. L. V. Snegur, Doctoral Thesis (Chemistry), A. N. Nesmeyanov Institute of Organoelement Compounds, Moscow, 2002.

  98. S. Takenaka, Y. Uto, M. Takagi, H. Kondo, Chem. Lett., 1998, 989.

  99. S. Takenaka, Y. Uto, H. Saita, M. Yokoyama, H. Kondo, W. D. Wilson, J. Chem. Soc., Chem. Commun., 1998, 1111

  100. S. Sato, S. Takenaka, J. Organomet. Chem., 2008, 693, 1177.

    Article  CAS  Google Scholar 

  101. M. Inouye, M. Takase, Angew. Chem., Int. Ed., 2001, 40, 1746.

    Article  CAS  Google Scholar 

  102. T. Smit, J. R. Snyman, E. W. Neuse, L. Bohm, C. E. van Rensburg, Anti-Cancer Drugs, 2005, 16, 501.

    Article  CAS  Google Scholar 

  103. M. G. Meirim, E. W. Neuse, G. Caldwell, J. Inorg. Organometal. Polym., 1997, 7, 71.

    Article  CAS  Google Scholar 

  104. T. Smit, E. W. Neuse, P. Becker, R. Anderson, C. E. J. van Rensburg, Drug Davelop. Res., 2006, 66, 204.

    Article  Google Scholar 

  105. N. F. Blom, E. W. Neuse, H. G. Tomas, Transition. Met. Chem., 1987, 12, 301.

    Article  CAS  Google Scholar 

  106. J. C. Swarts, E. W. Neuse, G. J. Lamprecht, J. Inorg. Organometal. Polym., 1994, 4, 143.

    Article  CAS  Google Scholar 

  107. S. Cowell, Zh. Zhilina, M. Kavarana, I. Alves, V. J. Hruby, 2nd International Symposium, 17th American Peptide Symposium, San Diego, California, 2001, Program and Abstracts, p. 371.

  108. S. G. Ward, R. C. Taylor, P. Köpf-Maier, H. Köpf, J. Balzarini, E. De Clercq, Appl. Organomet. Chem., 1989, 3, 491.

    Article  CAS  Google Scholar 

  109. D. Osella, M. Ferrali, P. Zanello, F. Laschi, M. Fontani, C. Nervi, G. Cavigiolio, Inorg. Chim. Acta, 2000, 306, 42

    Article  CAS  Google Scholar 

  110. G. Tabbi, C. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I. Viano, D. Osella, J. Med. Chem., 2002, 45, 5786.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to L. V. Snegur.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2113–2124, December, 2010.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Snegur, L.V., Babin, V.N., Simenel, A.A. et al. Antitumor activities of ferrocene compounds. Russ Chem Bull 59, 2167–2178 (2010). https://doi.org/10.1007/s11172-010-0377-8

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-010-0377-8

Key words

Navigation