Structure, NMR spectra and cytotoxic efect of palladium(II) and platinum(II) complexes of glyoxylic acid oxime

Chemija

Volumn 20, Issue 4, 2009, Pages 208-217

  Dodof, Nicolay I ^a   Kubiak, Maria ^b   Kuduk Jaworska, Janina ^b   Mastalarz, Agnieszka ^b   Kochel, Andrzej ^b   Vassilieva, Vladimira ^a   Vassilev, Nikolay ^c   Trendaflova, Natasha ^d   Georgieva, Ivelina ^d   Lalia Kantouri, Maria ^e   Apostolova, Margariata ^a  

^a INSTITUTE OF MOLECULAR BIOLOGY   (Bulgaria)

^b UNIVERSITY OF WROC AW   (Poland)

^c INSTITUTE OF ORGANIC CHEMISTRY   (Bulgaria)

^d INSTITUTE OF GENERAL AND INORGANIC CHEMISTRY   (Bulgaria)

^e ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

Crystal structure; Cytotoxic activity; Glyoxylic acid oxime; NMR spectra; Pd(II) and Pt(II) complexes

Indexed keywords

EID: 80052044448     PISSN: 02357216     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (79)

1. M. E. Keeney, K. Osseo-Asare, K. A. Woode, Coord. Chem. Rev., 59, 141 (1984).
2. a) T. Yu. Sliva, A. Dobosz, L. Jerzykiewicz, A. Karaczyn, A. M. Moreeuw, J. Świa̧tek-Kozłowska, T. Głowiak, H. Kołzowski, J. Chem. Soc., Dalton Trans., 1863 (1998)
3. b) A. A. Mokhir, E. Gumienna-Kontecka, J. Świa̧tek- Kozłowska, E. G. Petkova, I. O. Fritsky, L. Jerzykiewicz, A. A. Kapshuk, T. Yu. Sliva, Inorg. Chim. Acta, 329, 113 (2002)
4. c) A. Dobosz, N. M. Dudarenko, O. I. Fritsky, T. Głowiak, A. Karaszyn, H. Kołzowski, T. Yu. Sliva, J. Świa̧tek- Kozłowska, J. Chem. Soc., Dalton Trans., 743 (1999)
5. d) K. Malek, M. Vala, J. Świa̧tek-Kozłowska, L. M. Proniewicz, New J. Chem., 28, 477 (2004)
6. e) K. Malek, H. Kołzowski, L. M. Proniewicz, Polyhedron, 24, 1175 (2005).
7. A. W. Apblett, G. D. Georgieva, Phosphorus, Sulfur, Silicon Relat. Elem., 93-94, 479 (1994).
8. Z. Zhang, R. Liu, M. Zhao, Y. Qian, Mater. Chem. Phys., 71, 161 (2001).
9. M. R. Hill, A. W. Jones, J. J. Russell, N. K. Roberts, R. N. Lamb, Inorg. Chim. Acta, 358, 201 (2005).
10. a) Yu. V. Shklyaev, B. Ya. Syropyatov, V. S. Shklyaev, M. S. Gavrilov, E. S. Boronenkova, R. Z. Dautova, B. B. Aleksandrov, A. A. Gorbunov, Pharm. Chem. J., 33, 467 (1999)
11. b) V. O. Koz'minykh, E. N. Koz'minykh, Pharm. Chem. J., 38, 67 (2004).
12. A. I. Mikhaleva, A. B. Zaitsev, B. A. Trofimov, Russian Chem. Rev., 75, 797 (2006).
13. a) N. Trendafilova, G. Bauer, I. Georgieva, V. Delchev, J. Mol. Struct., 604, 211 (2002)
14. b) I. Georgieva, D. Binev, N. Trendafilova, G. Bauer, Chem. Physics, 286, 205 (2003)
15. c) I. Georgieva, N. Trendafilova, D. Binev, Vibr. Spectrosc., 31, 143 (2003)
16. d) I. Georgieva, N. Trendafilova, Chem. Physics, 321, 311 (2006).
17. a) I. Georgieva, N. Trendafilova, L. Rodríguez-Santiago, M. Sodupe, J. Phys. Chem., A, 109, 5668 (2005)
18. b) I. Georgieva, N. Trendafilova, G. Bauer, Spectrochim. Acta, A, 63, 403 (2006).
19. N. Trendafilova, G. Bauer, I. Georgieva, N. Dodoff, Spectrochim. Acta, A, 55, 2849 (1999).
20. K. Mereiter, Private Communication, CC DC-242816 (2004).
21. a) M. A. Jakupec, M. Galanski, B. K. Keppler, Rev. Physiol. Biochem. Pharmacol., 146, 1 (2003)
22. b) M. Galanski, Rec. Pat. Anti-Cancer Drug Discov., 1, 285 (2006)
23. c) I. Kostova, Rec. Pat. Anti-Cancer Drug Discov., 1, 1 ( 2006).
24. a) M. Coluccia, G. Natile, Anti Cancer Agents Med. Chem., 7, 111 (2007)
25. b) U. Kalinowska-Lis, J. Ochocki, K. Matlawska-Wasowska, Coord. Chem. Rev., 252, 1328 (2008).
26. S. Mazzega Sbovata, F. Bettio, C. Marzano, A. Tassan, M. Mozzon, R. Bertani, F. Benetollo, R. A. Michelin, J. Inorg. Biochem., 102, 882 (2008).
27. A. G. Quiroga, L. Cubo, E. de Blas, P. Aller, C. Navarro-Ranninger, J. Inorg. Biochem., 101, 104 (2007).
28. H. I. Hall, K. Taylor, M. C. Miller, X. Dothan, M. A. Khan, F. M. Bouet, Anticancer Res., 17, 2411 (1997).
29. D. Jayaraju, A. K. Kondapi, Curr. Science, 81, 787 (2001).
30. a) N. Saglam, A. Colak, K. Serbest, S. Dülger, S. Güner, S. Karaböcek, A. O. Beldüz, Biometals, 15, 357 (2002)
31. b) K. Serbest, S. Karaböcek, I. Deǧirmencioǧlu, S. Güner, Trans. Metal Chem., 26, 375 (2001).
32. M. S. S. Babu, K. H. Reddy, P. G. Krishna, Polyhedron, 26, 572 (2007).
33. S. Anbu, M. Kandaswamy, P. Suthakaran, V. Murugan, B. Varghese, J. Inorg. Biochem., 103, 401 (2009).
34. R. G. Kurmangalieva, I. A. Poplavskaya, K. A. Abdulin, T. A. Andreyanova, T. S. Safonova, Pharm. Chem. J., 26, 730 (1992).
35. S. Soga, Y. Shiotsu, S. Akinaga, S. V. Sharma, Curr. Cancer Drug Targets, 3, 359 (2003).
36. J.-G. Cui, L. Fan, L.-L. Huang, H.-L. Liu, A.-M. Zhou, Steroids, 74, 62 (2009).
37. H.-J. Park, K. Lee, S.-J. Park, B. Ahn, J.-C. Lee, H. Y. Cho, K.-I. Lee, Bioorg. Med. Chem. Lett., 15, 3307 (2005).
38. S. Rajabalian, A. Foroumadi, A. Shafiee, S. Emani, J. Pharm. Pharmaceut. Sci., 10, 153 (2007).
39. K. Cui, L. Wang, H. Zhu, S. Gou, Y. Liu, Bioorg. Med. Chem. Lett., 16, 2937 (2006).
40. A. Garoufis, S. K. Hadjikakou, N. Hadjiliadis, Coord. Chem. Rev., 253, 1384 (2009).
41. H. Wieland, Ber., 43, 3362 (1910).
42. Oxford Diffraction, CrysAlis RED, CrysAlisCCD (Version 1.171.30) and KM4CCD, Oxford Diffraction Ltd., Abingdon, Oxfordshire, UK (2004).
43. a) G. M. Sheldrick, ShelxS97, Program for the Solution of Crystal Structures, University of Göttingen, Germany (1997)
44. b) G. M. Sheldrick, ShelxL97, Program for the Refinement of Crystal Structures, University of Göttingen, Germany (1997).
45. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem., 62, 7512 (1997).
46. R. K. Harris, E. D. Becker, S. M. Cabral de M enezes, P. Granger, R. E. Hoffman, K. W. Zilm, Pure Appl. Chem., 80, 59 (2008).
47. T. Mosmann, J. Immunol. Methods, 65, 55 (1983).
48. K. Mereiter, Technical University of Vienna, Private communication (2003).
49. J. K. Maurin, Acta Cryst., C, 51, 2111 (1995).
50. a) Yu. A. Simonov, T. Yu. Sliva, M. D. Mazus, A. A. Dvorkin, R. D. Lampeka, Zh. Neorg. Khim., 34, 873 (1995)
51. Chem. Abstr., 111, 89292c (1989)
52. b) A. A. Dvorkin, Yu. A. Simonov, T. Yu. Sliva, R. D. Lampeka, M. D. Mazus, V. V. Skopenko, T. I. Malinovskii, Zh. Neorg. Khim., 34, 2582 (1989)
53. Chem. Abstr., 112, 150654m (1990)
54. V. V. Skopenko, T. Yu. Sliva, Yu. A. Simonov, A. A. Dvorkin, M. D. Mazus, R. D. Lampeka, T. I. Malinovskii, Zh. Neorg. Khim. 35, 1743 (1990)
55. Chem. Abstr., 113, 243530d (1990)
56. d) R. D. Lampeka, Z. D. Uzakbergenova, V. V. Skopenko, Z. Naturforsch., B, 48, 409 (1993)
57. e) R. D. Lampeka, N. M. Dudarenko, V. V. Skopenko, Acta Cryst., C, 50, 706 (1994)
58. R. Lampeka, R. Bergs, R. Kramer, K. Polborn, W. Beck, Z. Naturforsch., B, 49, 225 (1994)
59. f) R. Bergs, R. Lampeka, C. Robl, W. Beck, Z. Naturforsch., B, 49, 483 (1994).
60. M. V. Kirillova, M. Haukka, A. M. Kirillov, J. A. L. Silva, J. A. R. Fraústo da Silva, A. J. L. Pombeiro, Acta Cryst., E, 63, m1670 (2007).
61. A. A. Bagabas, A. W. Apblett, A. M. Shemsi, Z. S. Seddigi, Main Group Chem., 7, 65 (2008).
62. S. J. Berners-Price, L. Ronconi, P. J. Sadler, Progr. Nucl. Magnet. Reson. Spectrosc., 49, 65 (2006).
63. J. R. L. Priqueler, I. S. Butler, F. D. Rochon, Appl. Spectrosc. Rev., 41, 185 (2006).
64. R. M. Silverstein, G. C. Bassler, T. C. Morrill, Spectrometric Identification of Organic Compounds (Russian), 3rd edn., Mir, Moscow (1977).
65. N. I. Dodoff, D. Kovala-Demertzi, M. Kubiak, J. Kuduk-Jaworska, A. Kochel, G. A. Gorneva, Z. Naturforsch., B, 61, 1110 (2006).
66. a) F. D. Rochon, G. Massarweh, Inorg. Chim. Acta, 359, 4095 (2006)
67. b) F. D. Rochon, C. Bonnier, Inorg. Chim. Acta, 360, 461 (2007)
68. c) F. D. Rochon, C. Tessier, V. Buculei, Inorg. Chim. Acta, 360, 2255 (2007)
69. d) F. Rochon, C. Bensimon, C. Tessier, Inorg. Chim. Acta, 361, 16 (2008)
70. e) F. D. Rochon, P. S. Dieng, Inorg. Chim. Acta, 361, 1222 (2008).
71. G. C. Levy, R. L. Lichter, G. L. Nelson, Carbon-13 Nuclear Magnetic Resonance Spectroscopy, 2nd edn., 136-137, 161-162, John Wiley & Sons, New York (1980).
72. E. Breitmaier, Structure Elucidation by NMR in Organic Chemistry, 14-15, 27-29, John Wiley & Sons, Chichester (1993).
73. T. D. W. Claridge, High Resolution NMR Techniques in Organic Chemistry, 2nd edn., 79-80, Elsevier, Oxford (2009).
74. S. van Zutphen, E. Pantoja, R. Soriano, C. Soro, D. M. Tooke, A. L. Spek, H. den Dulk, J. Brower, J. Reedijk, J. Chem. Soc. Dalton Trans., 1020 (2006).
75. W.-C. Su, S.-L. Chang, T.-Y. Chen, J.-S. Chen, C.-J. Tsao, Jpn. J. Clin Oncol., 30, 562 (2000).
76. C. M. Riley, L. A. Sternson, in: K. Florey (ed.), Analytical Profiles of Drug Substances, Vol. 14, 78-105, Academic Press, New York (1985).
77. K. R. Harrap, Cancer Treat Rev., 12, Suppl. A, 21 (1985).
78. S. Elmore, Toxicol. Pathol., 35, 495 (2007).
79. T. Boulikas, M. Vougiouka, Oncol. Rep., 10, 1663 (2003).