Advertisement

Russian Chemical Bulletin

, Volume 63, Issue 11, pp 2405–2422 | Cite as

Ferrocenes as potential anticancer drugs. Facts and hypotheses

  • V. N. Babin
  • Yu. A. Belousov
  • V. I. Borisov
  • V. V. Gumenyuk
  • Yu. S. Nekrasov
  • L. A. Ostrovskaya
  • I. K. Sviridova
  • N. S. Sergeeva
  • A. A. Simenel
  • L. V. Snegur
Reviews

Abstract

We analyzed the research data on antitumor effects of a wide range of ferrocene compounds and discussed possible mechanisms of their bioactivities. Current trends in the study of anticancer effects of ferrocene derivatives were considered. Promising ways in the design of low-toxicity anticancer ferrocene-based drugs of new generation were outlined.

Keywords

ferrocene ferrocenylalkyl azoles anticancer activity mechanisms of anticancer action telomers telomerase apoptosis 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    T. J. Kealy, P. L. Pauson, Nature, 1951, 168, 1039.Google Scholar
  2. 2.
    S. A. Miller, J. A. Tebboth, J. F. Tremaine, J. Chem. Soc., 1952, 632.Google Scholar
  3. 3.
    T. S. Zatsepin, S. Yu. Andreev, T. Hianik, T. S. Oretskaya, Russ. Chem. Rev., 2003, 72, 537 [Usp. Khim., 2003, 72, 602].Google Scholar
  4. 4.
    D. R. van Staveren, N. Metzler-Nolte, Chem. Rev., 2004, 104, 5931.Google Scholar
  5. 5.
    E. W. Neuse, J. Inorg. Organomet. Polym. Materials, 2005, 15, 3.Google Scholar
  6. 6.
    H.-B. Kraatz, J. Inorg. Organomet. Polym. Materials, 2005, 15, 83.Google Scholar
  7. 7.
    X. Wu, M. L. Go, 26Fe The Use of Iron-Based Drugs in Medicine, in Metallotherapeutic Drugs and Metall-Based Diagnostic Agents: The Use of Metals in Medicine, Eds M. Gielen, E. Tiekink, J. Wiley & Sons, Chichester, 2005.Google Scholar
  8. 8.
    Bioorganometallics: Biomolecules, Labeling, Medicine, Ed. G. Jaouen, Wiley—VCH, Weinheim, 2006.Google Scholar
  9. 9.
    L. V. Snegur, V. N. Babin, A. A. Simenel, Yu. S. Nekrasov, L. A. Ostrovskaya, N. S. Sergeeva, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 2167 [Izv. Akad. Nauk, Ser. Khim., 2010, 2113].Google Scholar
  10. 10.
    C. Omelas, New J. Chem., 2011, 35, 1973.Google Scholar
  11. 11.
    G. Gasser, I. Ott, N. Metzler-Nolte, J. Med. Chem., 2011, 54, 3.Google Scholar
  12. 12.
    USSR Pat. 263807; Chem. Abstrs., 1978, 45180.Google Scholar
  13. 13.
    US Pat. 3957841; Chem. Abstrs., 1976, 543305.Google Scholar
  14. 14.
    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.Google Scholar
  15. 15.
    J. T. Yasrington, K. W. Huffman, G. A. Lesson, D. J. Sprinkle, D. E. Loudy, C. Hampton, G. J. Wright, J. P. Gibson, Fundam. Appl. Toxicol., 1983, 3, 86.Google Scholar
  16. 16.
    R. W. Mason, K. McGrouther, P. R. R. Rnatonge-Bandarage, B. H. Robinson, J. Simpson, Appl. Organomet. Chem., 1999, 13, 163.Google Scholar
  17. 17.
    S. Top, J. Tang, A. Vessieres, D. Carrez, C. Provot, G. Jaouen, Chem. Commun., 1996, 955.Google Scholar
  18. 18.
    S. Top, A. Vessieres, C. Cabestaing, I. Laios, G. Leclercq, C. Provot, G. Jaouen, J. Organomet. Chem., 2001, 637, 500.Google Scholar
  19. 19.
    S. Top, A. Vessieres, G. Leclercq, J. Quivy, J. Tang, J. Vaissermann, M. Huche, G. Jaouen, Chem. Eur. J., 2003, 9, 5223.Google Scholar
  20. 20.
    C. Biot, G. Glorian, L. A. Maciejewski, J. S. Brocard, J. Med. Chem., 1997, 40, 3715.Google Scholar
  21. 21.
    O. Domarle, G. Blampain, H. Agnaniet, T. Nzadiyabi, J. Lebibi, J. S. Brocard, L. A. Maciejewski, C. Biot, A. J. Georges, P. Millet, Antimicrob. Agents Chemother., 1998, 42, 540.Google Scholar
  22. 22.
    L. Delhaes, C. Biot, L. Berry, L. A. Maciejewski, D. Camus, J. S. Brocard, D. Dive, Bioorg. Med. Chem., 2000, 8, 2739.Google Scholar
  23. 23.
    C. Biot, L. Delhaes, L. A. Maciejewski, M. Mortuaire, D. Camus, D. Dive, J. S. Brocard, Eur. J. Med. Chem., 2000, 35, 707.Google Scholar
  24. 24.
    M. Blackie, P. Beagley, K. Chibale, C. Clarkson, J. R. Moss, P. J. Smith, J. Organomet. Chem., 2003, 688, 144.Google Scholar
  25. 25.
    X. Wu, P. Wilairat, M. L. Go, Bioorg. Med. Chem. Lett., 2002, 12, 2299.Google Scholar
  26. 26.
    J. Howarth, K. Hanlon, Tetrahedron Lett., 2001, 42, 751.Google Scholar
  27. 27.
    T. Itoh, S. Shirakami, N. Ishida, Y. Yamashita, T. Yoshida, H. S. Kim, Y. Wataya, Bioorg. Med. Chem. Lett., 2000, 10, 1657.Google Scholar
  28. 28.
    E. I. Edwards, R. Epton, G. Marr, J. Organomet. Chem., 1976, 107, 351.Google Scholar
  29. 29.
    E. I. Edwards, R. Epton, G. Marr, J. Organomet. Chem., 1979, 168, 259.Google Scholar
  30. 30.
    D. Scutaru, L. Tataru, I. Mazilu, E. Diaconu, T. Lixandru, C. Simionescu, J. Organomet. Chem., 1991, 401, 81.Google Scholar
  31. 31.
    D. Scutaru, I. Mazilu, M. Vata, L. Tataru, A. Vlase, T. Lixandru, C. Simionescu, J. Organomet. Chem., 1991, 401, 87.Google Scholar
  32. 32.
    D. Scutaru, I. Mazilu, L. Tataru, M. Vata, T. Lixandru, J. Organomet. Chem., 1991, 406, 183.Google Scholar
  33. 33.
    M. Salmain, Labeling of Proteins with Organometallic Complexes: Strategies and Applications, in Bioorganomet-allics. Biomolecules, Labelling, Medicine, Ed. G. Jaouen, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006, 181.Google Scholar
  34. 34.
    L. V. Snegur, A. A. Simenel, A. N. Rodionov, V. I. Boev, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 26 [Izv. Akad. Nauk, Ser. Khim., 2014, 26].Google Scholar
  35. 35.
    D. W. Johnson, G. W. Rayner-Canham, J. Chem. Educ., 1972, 49, 211.Google Scholar
  36. 36.
    A. N. Nesmeyanov, R. B. Materikova, I. R. Lyatifov, T. Kh. Kurbanov, N. S. Kochetkova, J. Organomet. Chem., 1978, 145, 241.Google Scholar
  37. 37.
    D. M. Duggan, D. N. Hendrickson, Inorg. Chem., 1975, 955.Google Scholar
  38. 38.
    E. G. Perevalova, M. D. Reshetova, K. I. Grandberg, Methody elementoorganicheskoi khimiii. Zhelezoorganicheskie soedineniya. Ferrotsen [Methods of Organoelement Chemistry. Organoiron Compounds. Ferrocene], Nauka, Moscow, 1983, 40 (in Russian).Google Scholar
  39. 39.
    T. Leigh, J. Chem. Soc., 1964, 3294.Google Scholar
  40. 40.
    R. B. Woodward, M. Rosenblum, M. C. Whiting, J. Am. Chem. Soc., 1952, 74, 3458.Google Scholar
  41. 41.
    M. Sato, H. Kono, M. Shiga, I. Motoyama, K. Hata, Bull. Chem. Soc. Jpn, 1968, 41, 252.Google Scholar
  42. 42.
    C. R. Hauser, J. K. Lindsay, J. Org. Chem., 1956, 21, 382.Google Scholar
  43. 43.
    V. Weinmayr, J. Am. Chem. Soc., 1955, 77, 3009.Google Scholar
  44. 44.
    M. Rausch, M. Vogel, H. Rosenberg, J. Org. Chem., 1957, 22, 900.Google Scholar
  45. 45.
    V. N. Babin, Yu. A. Belousov, I. R. Lyatifov, R. B. Materikova, V. V. Gumenyuk, J. Organomet. Chem., 1981, 214, C13.Google Scholar
  46. 46.
    V. N. Babin, Yu. A. Belousov, I. R. Lyatifov, R. B. Materikova, V. V. Gumenyuk, J. Organomet. Chem., 1981, 214, C11.Google Scholar
  47. 47.
    V. N. Babin, Yu. A. Belousov, T. A. Belousova, Yu. A. Borisov, V. V. Gumenyuk, Yu. S. Nekrasov, Russ. Chem. Bull. (Int. Ed.), 2011, 60, 2081 [Izv. Akad. Nauk, Ser. Khim., 2011, 2044].Google Scholar
  48. 48.
    S.-C. Chen, J. Organomet. Chem., 1980, 202, 183.Google Scholar
  49. 49.
    V. I. Boev, L. V. Snegur, V. N. Babin, Yu. S. Nekrasov, Russ. Chem. Rev., 1997, 66, 613 [Usp. Khim., 1997, 66, 677].Google Scholar
  50. 50.
    L. V. Snegur, V. I. Boev, Yu. S. Nekrasov, M. M. Ilyin, V. A. Davankov, Z. A. Starikova, A. I. Yanovsky, A. F. Kolomiets, V. N. Babin, J. Organomet. Chem., 1999, 580, 26.Google Scholar
  51. 51.
    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.Google Scholar
  52. 52.
    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.Google Scholar
  53. 53.
    A. A. Simenel, Yu. V. Kuzmenko, M. M. Ilyin, V. V. Gumenyuk, L. V. Snegur, Yu. S. Nekrasov, Russ. Chem. Bull. (Int. Ed.), 2004, 53, 939 [Izv. Akad. Nauk, Ser. Khim., 2004, 901].Google Scholar
  54. 54.
    A. A. Simenel, E. A. Morozova, Yu. V. Kuzmenko, L. V. Snegur, J. Organomet. Chem., 2003, 665, 13.Google Scholar
  55. 55.
    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.Google Scholar
  56. 56.
    A. N. Rodionov, PhD Thes. (in Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds of the RAS, Moscow, 2010, 150 pp. (in Russian).Google Scholar
  57. 57.
    A. N. Rodionov, A. A. Simenel, Yu. S. Nekrasov, V. V. Kachala, E. Yu. Osipova, K. Ya. Zherebker, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 405 [Izv. Akad. Nauk, Ser. Khim., 2010, 397].Google Scholar
  58. 58.
    A. N. Rodionov, A. A. Simenel, A. A. Korlyukov, V. V. Kachala, S. M. Peregudova, K. Ya. Zherebker, E. Yu. Osipova, J. Organomet. Chem., 2011, 696, 2108.Google Scholar
  59. 59.
    M. Joksovic, Z. Ratkovic, M. Vukicevic, D. Vukicevic, Synlett, 2006, 16, 2581.Google Scholar
  60. 60.
    I. Damljanovic, M. Vukicevic, N. Radulovic, R. Palic, E. Ellmerer, Z. Ratcovic, M. D. Joksovic, R. D. Vukicevic, Bioorg. Med. Chem. Lett., 2009, 19, 1093.Google Scholar
  61. 61.
    M. D. Joksovic, V. Markovic, Z. D. Juranic, T. Stanojkovic, L. S. Jovanovic, I. S. Damljanovic, K. M. Szécsényi, N. Todorovic, S. Trifunovic, R. D. Vukicevic, J. Organomet. Chem., 2009, 694, 3935.Google Scholar
  62. 62.
    I. Damljanovic, M. olovic, M. Vukicevic, D. Malojloc, N. Radulovic, K. Wurst, G. Laus, Z. Ratcovic, M. Joksovic, R. D. Vukicevic, J. Organomet. Chem., 2009, 694, 1575.Google Scholar
  63. 63.
    E. Bucci, L. D. Napoli, G. D. Fabio, A. Messere, D. Montesarchio, A. Romanelli, G. Piccialli, M. Varra, Tetrahedron, 1999, 14435.Google Scholar
  64. 64.
    P. Meunier, I. Ouattara, B. Gautheron, J. Tirouflet, D. Camboli, J. Besanson, Eur. J. Med. Chem., 1991, 26, 351.Google Scholar
  65. 65.
    A. Anne, B. Blanc, J. Moiroux, Bioconjugate Chem., 2001, 12, 396.Google Scholar
  66. 66.
    A. E. Beilstein, M. W. Grinstaff, J. Organomet. Chem., 2001, 398, 637.Google Scholar
  67. 67.
    P. Brázdilová, M. Vrábel, R. Pohl, H. Pivonková, L. Havran, M. Hocek, M. Fojta, Chem. Eur. J., 2007, 13, 9527.Google Scholar
  68. 68.
    A. R. Pike, L. C. Ryder, B. R. Horrocks, W. Clegg, M. R. J. Eselgord, B. A. Connolly, A. Houlton, Chem. Eur. J., 2002, 8, 2891.Google Scholar
  69. 69.
    A. R. Pike, L. C. Ryder, B. R. Horrocks, W. Clegg, B. A. Connolly, A. Houlton, Chem. Eur. J., 2005, 11, 344.Google Scholar
  70. 70.
    M. Inouye, M. Takase, Angew. Chem., Int. Ed., 2001, 40, 1746.Google Scholar
  71. 71.
    G. N. Yashchenko, A. A. Shashmurina, G. M. Anoshina, L. A. Gorelova, N. G. Evstigneeva, L. V. Alekseeva, L. B. Radina, Pharm. Chem. J. (Engl. Transl.), 1978, 12, 1317 [Khim. -Farm. Zh., 1978, 12, No. 10, 68].Google Scholar
  72. 72.
    V. N. Babin, A. V. Dubinin, P. M. Raevskii, A. F. Sviridov, A. L. Sherman, Model khimicheskogo kantserogeneza (mole-kulyarnye aspekty) [Model of Chemical Carcinogenesis (Molecular Aspects)], in Modeli. Algoritmy. Prinyatie reshenii [Models. Algorithms. Decision Making], Nauka, Moscow, 1979, 153 pp. (in Russian).Google Scholar
  73. 73.
    P. Köpf-Maier, H. Köpf, E. W. Neuse, Angew. Chem., Int. Ed., 1984, 23, 456.Google Scholar
  74. 74.
    P. Köpf-Maier, H. Köpf, E. W. Neuse, J. Cancer Res. Clin. Oncol., 1984, 108, 336.Google Scholar
  75. 75.
    P. Köpf-Maier, Eur. J. Clinic. Pharm., 1994, 47, 1.Google Scholar
  76. 76.
    V. N. Babin, P. M. Raevskii, K. G. Shitkov, L. V. Snegur, Yu. S. Nekrasov, Mendeleev Chem. J., 1995, 39, 17 [Zh. Ross. Khim. Obshch-va im D. I. Mendeleeva (Ross. Khim. Zh.), 1995, 39, 19].Google Scholar
  77. 77.
    L. A. Ostrovskaya, S. D. Varfolomeev, M. G. Voronkov, D. B. Korman, N. V. Blyukhterova, M. M. Fomina, V. A. Rykova, V. M. Goldberg, K. A. Abzaeva, L. V. Zhilitskaya, L. V. Snegur, A. A. Simenel, S. I. Zykova, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 1211 [Izv. Akad. Nauk, Ser. Khim., 2014, 1211].Google Scholar
  78. 78.
    E. W. Neuse, F. Kanzawa, Appl. Organomet. Chem., 1990, 4, 19.Google Scholar
  79. 79.
    S. Takenaka, Y. Uto, H. Saita, M. Yokoyama, H. Kondo, W. D. Wilson, Chem. Commun., 1998, 1111.Google Scholar
  80. 80.
    S. Sato, S. Takenaka, J. Organomet. Chem., 2008, 693, 1177.Google Scholar
  81. 81.
    E. W. Neuse, Polym. Adv. Technol., 1998, 9, 786.Google Scholar
  82. 82.
    T. Smit, J. R. Snyman, E. W. Neuse, L. Bohm, C. E. van Rensburg, Anti-Cancer Drugs, 2005, 16, 501.Google Scholar
  83. 83.
    T. Smit, E. W. Neuse, P. Becker, R. Anderson, C. E. J. van Rensburg, Drug Development Res., 2005, 66, 204.Google Scholar
  84. 84.
    H. S. Mandal, H.-B. Kraatz, J. Organomet. Chem., 2002, 45, 5786.Google Scholar
  85. 85.
    D. Osella, M. Ferrali, P. Zanello, F. Laschi, M. Fontani, C. Nervi, G. Cavigiolio, Inorg. Chim. Acta, 2000, 306, 42.Google Scholar
  86. 86.
    G. Tabbi, C. Cassino, G. Cavigiolio, D. Colangelo, A. Ghiglia, I. Viano, D. Osella, J. Med. Chem., 2002, 45, 5786.Google Scholar
  87. 87.
    A. Vessières, S. Top, W. Beck, E. Hillard, G. Jaouen, Dalton Trans., 2006, 529.Google Scholar
  88. 88.
    I. Zanellato, J.-M. Heldt, A. Vessieres, G. Jaouen, D. Osella, Inorg. Chim. Acta, 2009, 362, 4037.Google Scholar
  89. 89.
    M. Gormen, D. Plauk, P. Pigeon, E. A. Hillard, M. A. Plamont, S. Top, A. Vessières, G. Jaouen, Tetrahedron Lett., 2010, 51, 118.Google Scholar
  90. 90.
    U. Schatzschneider, N. Metzler-Nolte, Angew. Chem., Int. Ed., 2006, 45, 1504.Google Scholar
  91. 91.
    F. Noor, R. Kinscherf, G. A. Bonaterra, S. Walczak, S. Wöltl, N. Metzler-Nolte, ChemBioChem., 2009, 10, 493.Google Scholar
  92. 92.
    Z. H. Chohan, M. M. Nasser, Appl. Organomet. Chem., 2007, 21, 1005.Google Scholar
  93. 93.
    W. Henderson, S. R. Alley, Inorg. Chim. Acta, 2001, 322, 106.Google Scholar
  94. 94.
    N. Metzler-Nolte, M. Salmain, The Bioorganometallic Chemistry of Ferrocene, in Ferrocenes: Ligands, Materials and Biomolecules, Ed. P. Št pni ka, J. Wiley and Sons, 2008.Google Scholar
  95. 95.
    T. A. K. Al Allaf, L. J. Rashan, Appl. Organomet. Chem., 1999, 13, 63.Google Scholar
  96. 96.
    F. D. Popp, S. Roth, J. Kirbay, J. Med. Chem., 1963, 6, 83.Google Scholar
  97. 97.
    F. D. Popp, J. Pharm. Sci., 1973, 62, 679.Google Scholar
  98. 98.
    V. J. Fiorina, R. J. Dubois, S. Brynes, J. Med. Chem., 1978, 21, 393.Google Scholar
  99. 99.
    H. Köpf, P. Köpf-Maier, Angew. Chem., Int. Ed., 1979, 18, 477.Google Scholar
  100. 100.
    P. Köpf-Maier, M. Leitner, H. Köpf, J. Inorg. Nucl. Chem., 1980, 42, 1789.Google Scholar
  101. 101.
    P. Köpf-Maier, B. Hesse, H. Köpf, J. Cancer Res. Clin. Oncol., 1980, 96, 43.Google Scholar
  102. 102.
    P. Köpf-Maier, A. Moorman, H. Köpf, Eur. J. Cancer Oncol., 1985, 21, 853.Google Scholar
  103. 103.
    P. Köpf-Maier, H. Köpf, Chem. Rev., 1987, 87, 1137.Google Scholar
  104. 104.
    P. Köpf-Maier, P. Erkenswick, Toxicology, 1984, 33, 171.Google Scholar
  105. 105.
    P. Köpf-Maier, Toxicology, 1985, 37, 111.Google Scholar
  106. 106.
    P. Köpf-Maier, P. Funke-Kaiser, Toxicology, 1986, 38, 81.Google Scholar
  107. 107.
    P. Köpf-Maier, Eur. J. Clin. Pharm., 1994, 47, 1.Google Scholar
  108. 108.
    K. Strohfeldt, M. Tacke, Chem. Soc. Rev., 2008, 37, 1174.Google Scholar
  109. 109.
    G. Kelter, N. Sweeney, K. Strohfeldt, H. H. Fiebig, M. Tacke, Anti-Cancer Drugs, 2005, 16, 1091.Google Scholar
  110. 110.
    O. Oberschmidt, A. R. Hamauske, C. Pampilln, K. Strohfeldt, N. J. Sweeney, M. Tacke, Anti-Cancer Drugs, 2007, 18, 317.Google Scholar
  111. 111.
    M. Tacke, Anti-Cancer Drugs, 2007, 18, 311.Google Scholar
  112. 112.
    I. Fichtmer, C. Pampilln, N. J. Sweeney, K. Strohfeldt, M. Tacke, Anti-Cancer Drugs, 2006, 17, 333.Google Scholar
  113. 113.
    L. V. Snegur, Doctorate Thes. (in Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds of the RAS, Moscow, 2002, 192 pp. (in Russian).Google Scholar
  114. 114.
    N. B. Morozova, L. V. Popova (Snegur), A. I. Ilina, 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, Izuchenie protivoopukholevoi aktivnosti triiodidov alkilza-meshchennykh kationov ferritsiniya v eksperimente [Ex-perimental Study of Anticancer Activity of Alkyl-Sub-stituted Ferrocenium Cations], in Khimioterapiya v le-chenii onkologicheskikh bolnykh [Chemotherapy in Treat-ment of Cancer Patients], Ministry of Healthcare of the Russian Federation, Moscow, 1993, 91 pp. (in Russian).Google Scholar
  115. 115.
    RF Pat. 2025125; Chem. Abstr., 1995, 806386.Google Scholar
  116. 116.
    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.Google Scholar
  117. 117.
    A. Houlton, R. M. G. Roberts, J. Silver, J. Organomet. Chem., 1991, 418, 107.Google Scholar
  118. 118.
    E. W. Neuse, Polym. Adv. Technol., 1998, 9, 786.Google Scholar
  119. 119.
    M. Wenzel, E. Nipper, W. Klose, J. Nucl. Med., 1977, 18, 367.Google Scholar
  120. 120.
    A. Taylor, M. Wenzel, Naturwiss, 1977, 64, 273.Google Scholar
  121. 121.
    M. Wenzel, M. Scheider, E. Liss, Z. Naturforsch., 1979, 34, 670.Google Scholar
  122. 122.
    W. H. Ang, P. J. Dyson, Eur. J. Inorg. Chem., 2006, 4003.Google Scholar
  123. 123.
    A. Nazarov, Ch. Hartinger, B. Keppler, P. Dyson, Appl. Organomet. Chem., 2008, 22, 300.Google Scholar
  124. 124.
    M. Gras, B. Therrien, G. Süss-Fink, A. Casini, F. Edafe, P. J. Dyson, J. Organomet. Chem., 2010, 695, 1119.Google Scholar
  125. 125.
    H. Tamura, M. Miwa, Chem. Lett., 1997, 1177.Google Scholar
  126. 126.
    L. V. Snegur, PhD Thes. (in Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds of the RAS, Moscow, 1993, 129 pp. (in Russian).Google Scholar
  127. 127.
    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.Google Scholar
  128. 128.
    A. A. Simenel, PhD Thes. (in Chem.), A. N. Nesmeyanov Institute of Organoelement Compounds of the RAS, Moscow, 2004, 120 pp. (in Russian).Google Scholar
  129. 129.
    G. Von Poelhsitz, A. L. Bogado, M. P. de Araujo, H. S. Selistre-de-Araujo, J. Ellena, E. E. Castellano, A. A. Batista, Polyhedron, 2007, 26, 4707. Google Scholar
  130. 130.
    E. W. Neuse, M. C. Meirim, N. F. Bloom, Organometallics, 1988, 7, 2562.Google Scholar
  131. 131.
    G. Pilloni, R. Graziani, B. Longato, Inorg. Chim. Acta, 1991, 190, 165.Google Scholar
  132. 132.
    D. T. Hill, G. R. Girard, F. L. McCabe, Inorg. Chem., 1989, 28, 3529.Google Scholar
  133. 133.
    J. S. Casas, M. V. Castao, M. C. Cifuentes, J. C. GarcíaMonteagudo, A. Sánchez, J. Sordo, U. Abram, J. Inorg. Biochem., 2004, 98, 1009.Google Scholar
  134. 134.
    A. Rosenfeld, J. Blum, D. Gibson, A. Ramu, Inorg. Chim. Acta, 1992, 201, 219.Google Scholar
  135. 135.
    J. C. Swarts, E. W. Neuse, G. J. Lamprecht, J. Inorg. Organomet. Polym., 1994, 4, 143.Google Scholar
  136. 136.
    M. G. Meirim, E. W. Neuse, G. Caldwell, J. Inorg. Organomet. Polym., 1997, 7, 71.Google Scholar
  137. 137.
    N. F. Blom, E. W. Neuse, H. G. Tomas, Trans. Met. Chem., 1987, 12, 301.Google Scholar
  138. 138.
    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, Mendeleev Chem. J. (Engl. Transl.), 1998, 42, 151 [Ross. Khim. Zh., 1998, 42, 178].Google Scholar
  139. 139.
    L. V. Snegur, S. I. Zykova, A. A. Simenel, Yu. S. Nekrasov, Z. A. Starikova, S. M. Peregudova, M. M. Ilin, V. V. Kachala, I. K. Sviridova, N. S. Sergeeva, Russ. Chem. Bull. (Int. Ed.), 2013, 62, 2056 [Izv. Akad. Nauk, Ser. Khim., 2013, 2056].Google Scholar
  140. 140.
    D. A. Oparin, V. D. Makhaev, V. D. Vilchevskaya, T. I. Zimatkina, Zh. V. Motylevich, S. M. Zimatkin, S. V. Zabrodskaya, A. I. Krylova, Yu. Yu. Gorelikova, Pharm. Chem. J. (Engl. Transl.), 1996, 30, 79 [Khim. -Farm. Zh., 1996, 30, No. 2, 11].Google Scholar
  141. 141.
    R. Kovjazin, T. Eldar, M. Patya, A. Vanichkin, H. M. Lander, A. Novogrodsky, The FASEB J., 2003, 17, 467.Google Scholar
  142. 142.
    S. Mueller, U. Hartmann, F. Mayer, Invest. New Drugs, 2007, 25(6), 519.Google Scholar
  143. 143.
    H. El Daly, U. M. Martens, Methods Mol. Biol., 2007, 405, 47.Google Scholar
  144. 144.
    D. Parsch, U. Brassat, T. H. Brümmendorf, J. Fellenberg, Cancer Invest., 2008, 26(6), 590.Google Scholar
  145. 145.
    E. Yu. Osipova, A. N. Rodionov, A. A. Simenel, Yu. A. Belousov, O. M. Nikitin, V. V. Kachala, J. Porphyrins Phthalocyanines, 2012, 16, 1225.Google Scholar

Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. N. Babin
    • 1
    • 2
  • Yu. A. Belousov
    • 1
  • V. I. Borisov
    • 3
  • V. V. Gumenyuk
    • 1
  • Yu. S. Nekrasov
    • 1
  • L. A. Ostrovskaya
    • 4
  • I. K. Sviridova
    • 5
  • N. S. Sergeeva
    • 5
  • A. A. Simenel
    • 1
  • L. V. Snegur
    • 1
  1. 1.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussian Federation
  2. 2.Scientific Research Company “Ultrasan”MoscowRussian Federation
  3. 3.Clinical Oncology Dispensary No. 1MoscowRussian Federation
  4. 4.N. M. Emanuel Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussian Federation
  5. 5.P. A. Herzen Moscow Research Institute of OncologyMoscowRussian Federation

Personalised recommendations