Abstract
The mixed-ligand complexes cis-PtII[R(CH2)nNH2](NH3)X2, where R = 2,2,6,6-tetramethyl-1-oxylpiperidin-4-yl, X2 = ClI or Cl2, n = 1 or 2, and binuclear complexes trans-3,4-bis[cis-ammine(iodochloro or dichloro)platinum(ii)amino]-2,2,6,6-tetramethylpiperidin-1-oxyls were synthesized. The reactivity of the aminonitroxide complexes toward DNA, the destabilizing effect of the adducts on DNA structure, and the distribution of the Pt adducts along the DNA duplex were studied. The platination activity of the complexes is affected by the natures of both the leaving ligands X and the carrying amino ligands. The decrease in the platination activity of the complexes with an increase in the amino ligand sizes is probably caused by steric hindrance. The complexes that effectively platinate isolated DNA and cause a moderate destabilizition of DNA duplex possess high antitumor activities.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
M. J. Bloemink and J. Reedijk, in Metal Ions in Biological Systems, Eds. H. Sigel and A. Sigel, M. Dekker, New York, 1996, 32, 641.
E. R. Jamieson and S. J. Lippard, Chem. Rev., 1999, 99, 2467.
V. D. Sen´, V. A. Golubev, L. M. Volkova, and N. P. Konovalova, J. Inorg. Biochem., 1996, 64, 69.
V. D. Sen´, A. V. Kulikov, A. V. Shugalii, and N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 1998, 1640 [Russ. Chem. Bull., 1998, 47, 1598 (Engl. Transl.)].
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, and N. P. Konovalova, Izv. Akad. Nauk, Ser. Khim., 2000, 1624 [Russ. Chem. Bull., Int. Ed., 2000, 49, 1613].
A. V. Shugalii, A. V. Kulikov, M. V. Lichina, V. A. Golubev, and V. D. Sen´, J. Inorg. Biochem., 1998, 69, 67.
T. V. Hambley, Coord. Chem. Rev., 1997, 166, 181.
S. G. Chaney, Int. J. Oncology, 1995, 6, 1291.
A. B. Shapiro, L. S. Bogach, V. M. Chumakov, A. A. Kropacheva, V. I. Suskina, and E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1975, 2077 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1975, 24 (Engl. Transl.)].
R. I. Zhdanov, N. G. Kapitanova, and E. G. Rozantsev, Izv. Akad. Nauk SSSR, Ser. Khim., 1980, 364 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1980, 29 (Engl. Transl.)].
V. D. Sen´, Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2094 [Bull. Acad. Sci. USSR, Div. Chem. Sci., 1989, 38, 1928 (Engl. Transl.)].
C. M. Giandomenico, M. J. Abrams, B. A. Murrer, J. F. Vollano, M. I. Rheinheimer, S. B. Wyer, G. E. Bossard, and J. D. Higgins, Inorg. Chem., 1995, 34, 1015.
F. Cotton and G. Wilkinson, Advanced Inorganic Chemistry, Wiley, New York, 1966, 1.
V. D. Sen´, V. V. Tkachev, and L. O. Atovmyan, Izv. Akad. Nauk, Ser. Khim., 1993, 367 [Russ. Chem. Bull., 1993, 42, 328 (Engl. Transl.)].
R. Zaludova, A. Zakovska, J. Kasparkova, Z. Balcarova, V. Kleinwachter, O. Vrana, N. Farrell, and V. Brabec, Eur. J. Biochem., 1997, 246, 508.
U. Frey, J. D. Ranford, and P. J. Sadler, Inorg. Chem., 1993, 32, 1333.
K. Inagaki, C. Ninomoya, and Y. Kidani, Chem. Lett., 1986, 233.
V. Boudny, O. Vrana, F. Gaucheron, V. Kleinwachter, M. Leng, and V. Brabec, Nucleic Acids Res., 1992, 20, 267.
S. U. Dunham, C. J. Turner, and S. J. Lippard, J. Am. Chem. Soc., 1998, 120, 5395.
Yu. S. Lazurkin, M. D. Frank-Kamenetskii, and E. N. Trifonov, Biopolym., 1970, 9, 1253.
V. N. Parmon, A. I. Kokorin, and G. M. Zhidomirov, Stabil´nye biradikaly [Stable Biradicals], Nauka, Moscow, 1980, 240 pp. (in Russian).
W. Saenger, Principles of Nucleic Acid Structure, Springer, New York, 1984.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Sen", V.D., Shugalii, A.V. & Kulikov, A.V. DNA modification by cis-diaminoplatinum(ii) complexes with aminonitroxide ligands. Russian Chemical Bulletin 51, 1058–1064 (2002). https://doi.org/10.1023/A:1019686323902
Issue Date:
DOI: https://doi.org/10.1023/A:1019686323902