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Synthesis, reactions with DNA, and antitumor activity of platinum complexes with aminonitroxyl radicals

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Abstract

The work is a review of the data on the synthesis of mono- and biradical PtII complexes with mono- and diaminonitroxyl radicals, as well as of a binuclear complex with diaminonitroxyl radical. A “mild” method is considered for the synthesis of a number of PtIV nitroxyl complexes (9–11), whose lipophilicity varies within a wide range due to the trans-ligands, i.e., the linear aliphatic acid moieties. Correlations between the structures of the complexes, efficiency of their binding to DNA, and the effect of this binding on the DNA stability were established. Cytotoxic properties of the complexes against the HeLa, H1299, and MCF7 tumor cells, the effect of the complexes on the cell cycle, and the p53 protein expression were studied. The data on the antitumor activity of the complexes in the animal tumor model, P388 leukemia, are given. The rate of the development of resistance to complex 10a for P388 leukemia is 2.5 times lower than the corresponding value for cisplatin. It was found that a synergistic enhancement of antitumor activity is observed when low doses of cisplatin and complexes 9b or 10b are simultaneously administered. The specificities of biological activity of the platinum nitroxyl complexes are presumably due to the antioxidant properties of the nitroxyl pharmacophore and the ability of these complexes to cause the p53-independent tumor cell death.

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References

  1. C. S. Wilcox, Pharmacol. Ther., 2010, 126, 119.

    Article  CAS  Google Scholar 

  2. B. P. Soule, F. Hyodo, K. Matsumoto, N. L. Simone, J. A. Cook, M. C. Krishna, J. B. Mitchell, Free Rad. Biol. Med., 2007, 42, 1632.

    Article  CAS  Google Scholar 

  3. N. P. Konovalova, G. N. Bogdanov, V. B. Miller, E. G. Rozantsev, M. B. Neiman, N. M. Emanuel, Dokl. Akad. Nauk SSSR, 1964, 157, 707 [Dokl. Chem. (Engl. Transl.), 1964].

    CAS  Google Scholar 

  4. A. B. Shapiro, A. A. Kropacheva, V. I. Suskina, B. V. Rozynov, E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1971, 864 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1971, 20, 780].

    Google Scholar 

  5. N. M. Emanuel, N. P. Konovalova, L. S. Povarov, A. B. Shapiro, R. F. Dyachkovskaya, V. I. Suskina, L. K. Denisova, US Pat. 4332934, 1982; http://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&adjacent=

  6. N. M. Emanuel, A. N. Rosenberg, V. A. Golubev, G. N. Bogdanov, L. S. Vasilieva, N. P. Konovalova, US Pat. 4558127, 1985; http://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&adjacent=

  7. N. M. Emanuel, V. D. Sen’, V. A. Golubev, G. N. Bogdanov, L. V. Vasil’eva, N. P. Konovalova, USSR Inventor’s Certificate No. 1259650, 1986; http://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&adjacent=

  8. N. M. Emanuel, N. P. Konovalova, in Bioactive Spin Labels, Ed. R. I. Zhdanov, Springer, Berlin, 1992, 439.

    Google Scholar 

  9. L. R. Kelland, Nature Rev., 2007, 7, 573.

    Article  CAS  Google Scholar 

  10. N. J. Wheate, S. Walker, G. E. Craig, R. Oun, Dalton Trans., 2010, 39, 8113.

    Article  CAS  Google Scholar 

  11. N. N. Blokhin, N. I. Perevodchikova, Khimioterapiya opukholevykh zabolevanii [Chemotherapy of Tumor Diseases], Moscow, Meditsina, 1984, 95 (in Russian).

    Google Scholar 

  12. L. R. Kelland, Uses of Inorganic Chemistry in Medicine, Ed. N. P. Farrell, Springer, Berlin, 1999, 109.

    Chapter  Google Scholar 

  13. A. V. Klein, T. W. Hambley, Chem. Rev., 2009, 109, 4911.

    Article  CAS  Google Scholar 

  14. B. Koeberle, M. T. Tomicic, S. Usanova, B. Kaina, Biochim. Biophys. Acta, 2010, 1806, 172.

    CAS  Google Scholar 

  15. Platinum and Other Heavy Metal Compounds in Cancer Chemotherapy, Eds A. Bonetti, R. Leone, F. M. Muggia, S. B. Howell, Humana Press, New York, 2009, 383 pp.

    Google Scholar 

  16. C. M. Giandomenico, M. J. Abrams, B. A. Murrer, J. F. Vollano, M. I. Rheinheimer, S. B. Wyer, G. E. Bossard, J. D. Higgins, Inorg. Chem., 1995, 34, 1015.

    Article  CAS  Google Scholar 

  17. V. D. Sen’, V. A. Golubev, L. M. Volkova, N. P. Konovalova, J. Inorg. Biochem., 1996, 64, 69.

    Article  Google Scholar 

  18. V. D. Sen’, A. V. Kulikov, A. V. Shugalii, N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 1998, 1640 [Russ. Chem. Bull. (Engl. Transl.), 1998, 47, 1598].

    Google Scholar 

  19. V. D. Sen’, N. A. Rukina, V. V. Tkachev, A. V. Pis’menskii, L. M. Volkova, S. A. Goncharova, T. A. Raevskaya, A. G. Tikhomirov, L. B. Gorbacheva, N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 2000, 1624 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1613]

    Google Scholar 

  20. V. D. Sen’, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2094 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1989, 38, 1928].

  21. V. D. Sen’, V. V. Tkachev, L. M. Volkova, S. A. Goncharova, T. A. Raevskaya, N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 2003, 403 [Russ. Chem. Bull., Int. Ed., 2003, 52, 421].

    Google Scholar 

  22. V. D. Sen’, V. A. Golubev, N. Yu. Lugovskaya, T. E. Sashenkova, N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 2006, 60 [Russ. Chem. Bull., Int. Ed., 2006, 55, 62].

    Google Scholar 

  23. V. D. Sen’, A. V. Shugalii, A. V. Kulikov, Izv. Akad. Nauk, Ser. Khim., 2002, 972 [Russ. Chem. Bull., Int. Ed., 2002, 51, 1058].

    Google Scholar 

  24. A. N. Chekhlov, Koord. Khim., 2005, 31, 179 [Russ. J. Coord. Chem. (Engl. Transl.), 2005, 31].

    Google Scholar 

  25. A. V. Shugalii, A. V. Kulikov, V. A. Golubev, M. V. Lichina, V. D. Sen’, J. Inorg. Biochem., 1998, 69, 67.

    Article  CAS  Google Scholar 

  26. R. A. Alderden, M. D. Hall, T. W. Hambley, J. Chem. Education, 2006, 83, 728.

    Article  CAS  Google Scholar 

  27. U. Frey, J. D. Ranford, P. J. Sadler, Inorg. Chem., 1993, 32, 1333.

    Article  CAS  Google Scholar 

  28. N. Farrell, Y. Qu, U. Bierbach, M. Valsecchi, E. Menta, Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drugs, Ed. B. Lippert, Verlag Helvetica Chimica Acta, Zurich, 1999, 479.

    Google Scholar 

  29. S. U. Dunham, C. J. Turner, S. J. Lippard, J. Am. Chem. Soc., 1998, 120, 5395.

    Article  CAS  Google Scholar 

  30. A. Miyajima, J. Nakashima, K. Yoshioka, M. Tashibana, H. Tazaki, M. Murai, British J. Cancer, 1997, 76, 206.

    Article  CAS  Google Scholar 

  31. P. Bravado, A. Armesilla, A. Silva, A. Porras, Apoptosis, 2007, 12, 1733.

    Article  Google Scholar 

  32. Y. Tsutsumishita, T. Onda, K. Okada, M. Takeda, H. Endou, S. Futaki, M. Niwa, Biochem. Biophys. Res. Comm., 1998, 242, 310.

    Article  CAS  Google Scholar 

  33. V. D. Sen’, V. A. Golubev, I. V. Kulyk, E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1976, 1745 [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1976, 25, 1647].

    Google Scholar 

  34. S. Goldstein, G. Merenyj, A. Russo, A. Samuni, J. Am. Chem. Soc., 2003, 125, 789.

    Article  CAS  Google Scholar 

  35. M. B. Gariboldi, V. Rimoldi, R. Supino, E. Favini, E. Monti, Free Radic. Biol. Med., 2000, 29, 633.

    Article  CAS  Google Scholar 

  36. S. Suy, J. B. Mitchell, A. Samuni, S. Mueller, U. Kasid, Cancer, 2005, 103, 1302.

    Article  CAS  Google Scholar 

  37. H. E. Seifried, S. S. McDonald, D. E. Anderson, P. Greenwald, J. A. Milner, Cancer Res., 2003, 63, 4295.

    CAS  Google Scholar 

  38. H. R. Sanders, M. Albitar, Cancer Gen. Cytogen., 2010, 203, 7.aaa

  39. T.-C. Chou, Pharm. Rev., 2006, 58, 621.

    Article  CAS  Google Scholar 

  40. W. Gorczyca, J. Gong, B. Ardelt, F. Traganos, Z. Darzynkiewicz, Cancer Res., 1993, 53, 3186.

    CAS  Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 prosp. Akad. Semenova, 142432, Chernogolovka, Moscow Region, Russian Federation

    V. D. Sen’, A. A. Terent’ev & N. P. Konovalova

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  1. V. D. Sen’
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  2. A. A. Terent’ev
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  3. N. P. Konovalova
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Correspondence to V. D. Sen’.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1319–1328, July, 2011.

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Sen’, V.D., Terent’ev, A.A. & Konovalova, N.P. Synthesis, reactions with DNA, and antitumor activity of platinum complexes with aminonitroxyl radicals. Russ Chem Bull 60, 1342–1351 (2011). https://doi.org/10.1007/s11172-011-0200-1

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