Bulletin of the Korean Chemical Society

  • 제32권3호
  • /
  • Pages.947-955
  • /
  • 2011
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  • 0253-2964(pISSN)
  • /
  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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DNA-Binding and Thermodynamic Parameters, Structure and Cytotoxicity of Newly Designed Platinum(II) and Palladium(II) Anti-Tumor Complexes

  • 투고 : 2010.11.27
  • 심사 : 2011.01.14
  • 발행 : 2011.03.20
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초록

The complexes [Pd(bpy)(Hex-dtc)]$NO_3$ and [Pt(bpy)(Hex-dtc)]$NO_3$ (bpy is 2,2'-bipyridine and Hex-dtc is hexyldithiocarbamato ligands) were synthesized and characterized by elemental analysis and spectroscopic studies. The cytotoxicity assay of the complexes has been performed on chronic myelogenous leukemia cell line, K562, at micromolar concentration. Both complexes showed cytotoxic activity far better than that of cisplatin under the same experimental conditions. The binding parameters of the complexes with calf thymus DNA (CT-DNA) was investigated using UV-visible and fluorescence techniques. They show the ability of cooperatively intercalating in CT-DNA. Gel filtration studies demonstrated that platinum complex could cleave the DNA. In the interaction studies between the Pd(II) and Pt(II) complexes with CT-DNA, several binding and thermodynamic parameters have been determined, which may provide deeper insights into the mechanism of action of these types of complexes with nucleic acids.

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참고문헌

  1. Kumar, R. S.; Arunachalam, S.; Periasamy, V. S.; Preethy, Ch. P.;Riyasdeen, A.; Akbarsha, M. A. Eur. J. Med. Chem. 2008, 43,2082. https://doi.org/10.1016/j.ejmech.2007.09.017
  2. Kelland, L. R. Eur. J. Can. 2005, 41, 971. https://doi.org/10.1016/j.ejca.2004.11.024
  3. Pyle, A. M.; Morii, T.; Barton, J. K. J. Am. Chem. Soc. 1990, 112,9432. https://doi.org/10.1021/ja00181a077
  4. Qiao, Ch.; B, Sh.; Sun, Y.; Song, D.; Zhang, H.; Zhou, W.Spectrochim. Acta A 2008, 70, 136. https://doi.org/10.1016/j.saa.2007.07.038
  5. Liu, M.; Yuan, W.; Zhang, Q.; Yan, L.; Yang, R. Spectrochim.Acta A 2008, 70, 1114. https://doi.org/10.1016/j.saa.2007.10.023
  6. Kumar, C. V.; Asuncion, H. E. J. Am. Chem. Soc. 1993, 115, 22.
  7. He, X. Q.; Lin, Q. Y.; Hu, R. D.; Lu, X. H. Spectrochim. Acta A.2007, 68, 184. https://doi.org/10.1016/j.saa.2006.11.012
  8. Kumar, R. S.; Arunachalam, S.; Periasamy, V. S.; Preethy, C. P.;Riyasdeen, A.; Akbarsha, M. A. J. Inorg. Biochem. 2009, 103,117. https://doi.org/10.1016/j.jinorgbio.2008.09.010
  9. Shavit, M.; Peri, D.; Melman, A.; Tshuva, E. Y. J. Biol. Inorg.Chem. 2007, 12, 825. https://doi.org/10.1007/s00775-007-0236-8
  10. Deegan, C.; McCann, M.; Devereux, M.; Coyle, B.; Egan, D. A.Cancer Lett. 2007, 247, 224. https://doi.org/10.1016/j.canlet.2006.04.006
  11. Tusek-Bozic, L.; Juribasic, M.; Traldi, P.; Scarcia, V.; Furlani, A.Polyhedron 2008, 27, 1317. https://doi.org/10.1016/j.poly.2008.01.002
  12. O'Dwyer, P. J.; Stevenson, P.; Johnson, S. W. Clinical Status ofCisplatin, Carboplatin, and other Platinum-based Antitumor Drugs;Lippert, B., Ed.; Chemistry and Biochemistry of a leading AnticancerDrug; Verlag Helvetica Chimica Acta: Zurich, 1999; p 31.
  13. Divsalar, A.; Saboury, A. A.; Mansouri-Torshizi, H.; Hemmatnejad,B. Bull. Korean. Chem. Soc. 2006, 27, 1801. https://doi.org/10.5012/bkcs.2006.27.11.1801
  14. Mansouri-Torshizi, H.; I-Moghaddam, M;. Divsalar, A.; Saboury,A. A. Bioorg. Med. Chem. 2008, 16, 9616. https://doi.org/10.1016/j.bmc.2008.08.021
  15. Saeidifar, M.; Mansouri-Torshizi, H.; Rezaei Behbehani, G.; Divsalar,A.; Saboury, A. A. Bull. Korean Chem. Soc. 2009, 30, 1951. https://doi.org/10.5012/bkcs.2009.30.9.1951
  16. Chen, X.; Xie, M.; Liu, W.; Ye, Q.; Yu, Y.; Hou, Sh.; Gao, W.; Liu,Y. Inorg. Chim. Acta 2007, 360, 2851. https://doi.org/10.1016/j.ica.2007.01.016
  17. Jain, N.; Srivastava, T. S. Inorg. Chim. Acta 1987, 128, 151. https://doi.org/10.1016/S0020-1693(00)86538-X
  18. I-Moghaddam, M.; Mansouri-Torshizi, H.; Divsalar, A.; Saboury,A. A. J. Iran. Chem. Soc. 2009, 6, 552. https://doi.org/10.1007/BF03246535
  19. Mansouri-Torshizi, H.; I-Moghaddam, M.; Divsalar, A.; Saboury,A. A. J. Biomol. Struct dyn. 2009, 26, 575. https://doi.org/10.1080/07391102.2009.10507273
  20. Palocsay, F. A.; Rund, J. V. Inorg. Chem. 1969, 8, 524. https://doi.org/10.1021/ic50073a022
  21. Bi, Sh.; Zhang, H.; Qiao, Ch.; Sun, Y.; Liu, Ch. Spectrochim. ActaA 2008, 69, 123. https://doi.org/10.1016/j.saa.2007.03.017
  22. Li, Y.; Yang, Z.; Wang, M. Eur. J. Med. Chem. 2009, 44, 4585. https://doi.org/10.1016/j.ejmech.2009.06.027
  23. Reichmann, M. F.; Rice, S. A.; Thomas, C. A.; Doty, P. J. Am. Chem. Soc. 1954, 76, 3047. https://doi.org/10.1021/ja01640a067
  24. Mansouri-Torshizi, H.; Saeidifar, M.; Divsalar, A.; Saboury, A.A.; Shahraki, S. Bull. Korean Chem. Soc. 2010, 31, 435. https://doi.org/10.5012/bkcs.2010.31.02.435
  25. Song, X. Q.; Wang, Y. W.; Zheng, J. R.; Liu, W. S.; Tan, M. Y.Spectrochim. Acta A 2007, 68, 701. https://doi.org/10.1016/j.saa.2006.12.048
  26. Mital, R.; Jain, N.; Srivastava, T. S. Inorg. Chim. Acta 1989, 166,135. https://doi.org/10.1016/S0020-1693(00)80798-7
  27. Gearg, W. J. J. Coord. Chem. Rev. 1971, 7, 81. https://doi.org/10.1016/S0010-8545(00)80009-0
  28. Gao, E.; Wang, L.; Zhu, M.; Liu, L.; Zhang, W. Eur. J. Med.Chem. 2010, 45, 311. https://doi.org/10.1016/j.ejmech.2009.10.014
  29. Matesanz, A. I.; Pérez, J. M.; Navarro, P.; Moreno, J. M.; Colacio,E.; Souza, P. J. Inorg. Biochem. 1999, 76, 29. https://doi.org/10.1016/S0162-0134(99)00105-1
  30. Gao, E.; Zhu, M.; Yin, H.; Liu, L.; Wu, Q.; Sun, Y. J. Inorg. Biochem. 2008, 102, 1958. https://doi.org/10.1016/j.jinorgbio.2008.07.011
  31. Divsalar, A.; Saboury, A. A.; Mansouri-Torshizi, H.; Moosavi-Movahedi, A. A. J. Biomol. Struct. Dyn. 2007, 25, 173. https://doi.org/10.1080/07391102.2007.10507166
  32. Mital, R.; Ray, K. S.; Srivastava, T. S.; Bahattacharya, R. K. J. Inorg. Biochem. 1986, 27, 133. https://doi.org/10.1016/0162-0134(86)80014-9
  33. Mital, R.; Srivastava, T. S. J. Inorg. Biochem. 1990, 40, 111. https://doi.org/10.1016/0162-0134(90)80044-X
  34. Jiang, M.; Li, Y.; Wu, Zh.; Liu, Zh.; Yan, C. J. Inorg. Biochem.2009, 103, 833. https://doi.org/10.1016/j.jinorgbio.2009.02.007
  35. Wolf, A.; Shimer, G. H., Jr.; Meehan, T. Biochemistry 1987, 26,6392. https://doi.org/10.1021/bi00394a013
  36. Liu, Z.; Wang, B.; Yang, Z.; Li, Y.; Qin, D.; Li, T. Eur. J. Med.Chem. 2009, 44, 4477. https://doi.org/10.1016/j.ejmech.2009.06.009
  37. Mansouri-Torshizi, H.; Islami-Moghaddam, M.; Saboury, A. A.Acta Biochim. Biophys. Sin. 2003, 35, 886.
  38. Greene, R. F.; Pace, C. N. J. Biol. Chem. 1974, 249, 5388.
  39. Saboury, A. A. J. Iran. Chem. Soc. 2006, 3, 1. https://doi.org/10.1007/BF03245784
  40. Peres-Flores, L.; Ruiz-Chica, A. J.; Delcros, J. G.; Sanches, F. M.;Ramirez, F. J. Spectrochim. Acta A 2008, 69, 1089. https://doi.org/10.1016/j.saa.2007.06.008
  41. King, A. M. Q.; Nicholson, B. H. Biochem. J. 1969, 114, 679.
  42. Bathaie, S. Z.; Bolhasani, A.; Hoshyar, R.; Ranjbar, B.; Sabouni,F.; Moosavi-Movahedi, A. A. Dna Cell Biol. 2007, 26, 533. https://doi.org/10.1089/dna.2007.0598
  43. Barrow, G. M. In Physical Chemistry, 5th ed.; MC. Graw-Hill:Chap. 7, New York, 1988.
  44. Divsalar, A.; Saboury, A. A.; Mansouri-Torshizi, H.; Ahmad, F. J.Phys. Chem. B 2010, 114, 3639. https://doi.org/10.1021/jp909143b
  45. Saboury, A. A.; Shamsaei, A. A.; Moosavi-Movahedi, A. A.;Mansouri-Torshizi, H. J. Chin. Chem. Soc. 1999, 46, 917.
  46. Scatchard, G. Ann. N. Y. Acad Sci. 1949, 51, 660. https://doi.org/10.1111/j.1749-6632.1949.tb27297.x
  47. Saboury, A. A.; Moosavi-Movahedi, A. A. Biochem. Edu. 1994,22, 48. https://doi.org/10.1016/0307-4412(94)90175-9
  48. Hill, A. V. J. Physil (Lond). 1910, 40, 4.
  49. Patel, M. N.; Parmar, P. A.; Gandhi, D. S. Bioorg. Med. Chem.2010, 18, 1227. https://doi.org/10.1016/j.bmc.2009.12.037
  50. Wang, Q.; Yang, Z.; Qi, G.; Qin, D. Eur. J. Med. Chem. 2009, 44,2425. https://doi.org/10.1016/j.ejmech.2008.10.023
  51. Tan, L. F.; Chao, H. Inorg. Chim. Acta 2007, 360, 2016. https://doi.org/10.1016/j.ica.2006.10.016
  52. Peng, B.; Chen, X.; Du, K.; Yu, B.; Chao, H.; Ji, L. Spectrochim.Acta A 2009, 74, 896. https://doi.org/10.1016/j.saa.2009.08.031
  53. Hacker, M. P.; Douple, E. B.; Krakoff, I. H. In PlatinumCoordination Complexes in Cancer Chemotherapy; Nijhoff, M.A., Ed.; Boston, 1984.
  54. Mansouri-Torshizi, H.; Saeidifar, M.; Divsalar, A.; Saboury, A. A.Spectrochim. Acta A 2010, 77, 312. https://doi.org/10.1016/j.saa.2010.05.029
  55. Wu, F.; Xiang, Y.; Wu, Y.; Xie, F. J. Luminesc. 2009, 129, 1286. https://doi.org/10.1016/j.jlumin.2009.06.010
  56. Sun, Y. T.; Bi, S. Y.; Song, D. Q.; Qiao, C. Y.; Mu, D.; Zhang, H.Q. Sens. Actuators B 2008, 129, 799. https://doi.org/10.1016/j.snb.2007.09.082
  57. Lakowicz, J. R.; Weber, G.; Biochemistry 1973, 12, 4161. https://doi.org/10.1021/bi00745a020
  58. Bai, G. Y.; Wang, K. Z.; Duan, Z. M.; Gao, L. H. J. Inorg. Biochem. 2004, 98, 1017. https://doi.org/10.1016/j.jinorgbio.2004.02.021
  59. Tysoe, S. A.; Kopelman, R.; Schelzig, D. Inorg. Chem. 1999, 38,5196. https://doi.org/10.1021/ic9901315
  60. Mansuri-Torshizi, H.; Mital, R.; Srivastava, T. S.; Parekh, H.;Chitnis, M. P. J. Inorg. Biochem. 1991, 44, 239. https://doi.org/10.1016/0162-0134(91)84029-9

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