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Synthesis, characterization, and DNA binding of complexes [Pt(bpy)(pip)]2+ and [Pt(bpy)(hpip)]2+

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Abstract

Two new platinum(II) complexes, [Pt(bpy)(pip)](NO3)2 (1) and [Pt(bpy)(hpip)](NO3)2·2H2O (2) (bpy is 2,2′-bypyridine; pip is 2-phenylimidazo[4,5-f][1,10]phenanthroline; hpip is 2-(2-hydroxyphenyl) imidazo[4,5-f][1,10]phenanthroline), have been synthesized and fully characterized by CHN analysis, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, 1H-NMR spectroscopy, IR spectroscopy (attenuated total reflection), and UV–vis spectroscopy. The DNA-binding behaviors of both complexes have been studied by spectroscopic methods and viscosity measurements, and their ability to inhibit DNA transcription was measured. The results indicate that both complexes show some degree of binding to DNA in an intercalative mode, resulting in intrinsic binding constants of (2.88 ± 0.4) × 104 and (5.38 ± 0.8) × 104 for 1 and 2, respectively. The comparatively observed difference in the DNA-binding affinities of the two complexes can be reasonably explained by the presence of intramolecular hydrogen bonding between the ortho phenolic group and the nitrogen atom of the imidazole ring. The extended coplanarity of the hpip ligand due to intramolecular hydrogen bonding may lead to an enhancement of the DNA-binding affinity of the hpip complex. In addition, the complexes can promote photocleavage of pUC19 DNA on irradiation as revealed by the spectroscopic and viscometric measurements, with 2 promoting cleavage of pUC19 DNA at lower concentration. Moreover, increasing concentrations of both complexes inhibited DNA transcription, and as expected 2 was shown to be a better antitumor agent than 1.

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References

  1. Li N, Ma Y, Yang C, Guo L, Yang X (2005) Biophys Chem 116:199–205

    Article  PubMed  CAS  Google Scholar 

  2. Barton JK, Goldberg JM, Kumar CV, Turro NJ (1986) J Am Chem Soc 108:2081–2088

    Article  CAS  Google Scholar 

  3. Cusumano M, Di Pietro ML, Giannetto A (2006) Inorg Chem 45:230–235

    Article  PubMed  CAS  Google Scholar 

  4. Xu C-J, Li B-G (2010) Macromol Chem Phys 211:1733–1740

    Article  CAS  Google Scholar 

  5. Jamieson ER, Lippard SJ (1999) Chem Rev 99:2467–2498

    Article  PubMed  CAS  Google Scholar 

  6. Novakova O, Kasparkova J, Vrana O, van Vliet PM, Reedijk J, Brabec V (1995) Biochemistry 34:12369–12378

    Article  PubMed  CAS  Google Scholar 

  7. Erkkila KE, Odom DT, Barton JK (1999) Chem Rev 99:2777–2796

    Article  PubMed  CAS  Google Scholar 

  8. Kelley SO, Holmlin RE, Stemp EDA, Barton JK (1997) J Am Chem Soc 119:9861–9870

    Article  CAS  Google Scholar 

  9. Farrell N (2002) Coord Chem Rev 232:1–4

    Article  CAS  Google Scholar 

  10. Zhang Q-L, Liu J-G, Liu J, Xue G-Q, Li H, Liu J-Z, Zhou H, Qu L-H, Ji L-N (2001) J Inorg Biochem 85:291–296

    Article  PubMed  CAS  Google Scholar 

  11. Uma Maheswari P, Palaniandavar M (2004) J Inorg Biochem 98:219–230

    Article  PubMed  CAS  Google Scholar 

  12. Chen H, Dou C, Wu Y, Li H, Xi X, Yang P (2009) J Inorg Biochem 103:827–832

    Article  PubMed  CAS  Google Scholar 

  13. Liu X-W, Lu J-L, Chen Y-D, Li L, Zhang D-S (2011) Inorg Chim Acta 379:1–6

    Article  CAS  Google Scholar 

  14. Grehl M, Krebs B (1994) Inorg Chem 33:3877–3885

    Article  CAS  Google Scholar 

  15. Yamada M, Tanaka Y, Yoshimato S, Kuroda S, Shimao I (1992) Bull Chem Soc Jpn 65:1006–1011

    Article  CAS  Google Scholar 

  16. Cohen G, Eisenberg H (1969) Biopolymers 8:45–55

    Article  CAS  Google Scholar 

  17. Steck EA, Day AR (1943) J Am Chem Soc 65:452–456

    Article  CAS  Google Scholar 

  18. Wu J-Z, Li L, Zeng T-X, Ji L-N, Zhou J-Y, Luo T, Li R-H (1997) Polyhedron 16:103–107

    Article  CAS  Google Scholar 

  19. Liu J-G, Ye B-H, Li H, Zhen Q-X, Ji L-N, Fu Y-H (1999) J Inorg Biochem 76:265–271

    Article  CAS  Google Scholar 

  20. Barton JK, Danishefsky A, Goldberg J (1984) J Am Chem Soc 106:2172–2176

    Article  CAS  Google Scholar 

  21. Cusumano M, Di Pietro ML, Giannetto A (1999) Inorg Chem 38:1754–1758

    Article  PubMed  CAS  Google Scholar 

  22. Liu J, Mei WJ, Lin LJ, Zheng KC, Chao H, Yun FC, Ji LN (2004) Inorg Chim Acta 357:285–293

    Article  CAS  Google Scholar 

  23. Tan L-F, Chao H (2007) Inorg Chim Acta 360:2016–2022

    Article  CAS  Google Scholar 

  24. Tan L-F, Chao H, Li H, Liu Y-J, Sun B, Wei W, Ji L-N (2005) J Inorg Biochem 99:513–520

    Article  PubMed  CAS  Google Scholar 

  25. Zhang Q-L, Liu J-G, Liu J-Z, Li H, Yang Y, Xu H, Chao H, Ji L-N (2002) Inorg Chim Acta 339:34–40

    Article  CAS  Google Scholar 

  26. Zhang Q-L, Xu H, Li H, Liu J, Liu J-Z, Ji L-N, Liu J-G (2002) Transit Metal Chem 27:149–154

    Article  CAS  Google Scholar 

  27. Mudasir Wijaya K, Yoshioka N, Inoue H (2003) J Inorg Biochem 94:263–271

    Article  PubMed  CAS  Google Scholar 

  28. Chen L-M, Liu J, Chen J-C, Tan C-P, Shi S, Zheng K-C, Ji L-N (2008) J Inorg Biochem 102:330–341

    Article  PubMed  CAS  Google Scholar 

  29. Ortmans I, Elias B, Kelly JM, Moucheron C, Kirsch-DeMesmaker A (2004) Dalton Trans 668–676

  30. Kelly JM, Tossi AB, McConnell DJ, OhUigin C (1985) Nucleic Acids Res 13:6017–6034

    Article  PubMed  CAS  Google Scholar 

  31. Eftink MR, Ghiron CA (1981) Anal Biochem 114:199–227

    Article  PubMed  CAS  Google Scholar 

  32. Baguley BC (1978) Nucleic Acids Res 5:161–171

    Article  PubMed  CAS  Google Scholar 

  33. Satyanarayana S, Dabrowiak JC, Chaires JB (1992) Biochemistry 31:9319–9324

    Article  PubMed  CAS  Google Scholar 

  34. Satyanarayana S, Dabrowiak JC, Chaires JB (1993) Biochemistry 32:2573–2584

    Article  PubMed  CAS  Google Scholar 

  35. Barton JK, Raphael AL (1984) J Am Chem Soc 106:2466–2468

    Article  CAS  Google Scholar 

  36. Wang XL, Chao H, Li H, Hong XL, Liu YJ, Tan LF, Ji LN (2004) J Inorg Biochem 98:1143–1150

    Article  PubMed  CAS  Google Scholar 

  37. Talib J, Harman DG, Dillon CT, Aldrich-Wright J, Beck JL, Ralph SF (2009) Dalton Trans 504–513

  38. Shi CY, Gao EJ, Ma S, Wang ML, Liu QT (2010) Bioorg Med Chem Lett 20:7250–7254

    Article  PubMed  CAS  Google Scholar 

  39. Jamieson ER, Lippard SJ (1999) Chem Soc Rev 99:2467

    Article  CAS  Google Scholar 

  40. Portugal J, Martin B, Vaquero A, Ferrer N, Villamarin S, Priebe W (2001) Curr Med Chem 8:1

    Article  PubMed  CAS  Google Scholar 

  41. Takusagawa F, Carlson RG, Weaver RF (2001) Bioorg Med Chem 9:719

    Article  PubMed  CAS  Google Scholar 

  42. Stellrecht CM, Chen LS (2011) Cancers 3:4170–4190

    Article  CAS  Google Scholar 

  43. Yan C, Higgins PJ (2013) Biochim Biophys Acta 1835:76–85

    PubMed  CAS  Google Scholar 

  44. Fu PKL, Turro C, (2001) Chem Commun 279–280

  45. Fu PKL, Bradley PM, Turro C (2003) Inorg Chem 42:878

    Article  PubMed  CAS  Google Scholar 

Download references

Acknowledgments

We are grateful for the support of Bulent Ecevit University with grant 2011-03-13-06. We also thank Zehra Safi Oz for the use of her laboratory to make it possible to visualize and photograph the gel electrophoresis results.

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Correspondence to Burak Coban.

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Coban, B., Yildiz, U. & Sengul, A. Synthesis, characterization, and DNA binding of complexes [Pt(bpy)(pip)]2+ and [Pt(bpy)(hpip)]2+ . J Biol Inorg Chem 18, 461–471 (2013). https://doi.org/10.1007/s00775-013-0991-7

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  • DOI: https://doi.org/10.1007/s00775-013-0991-7

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