Skip to main content
Log in

Equilibrium studies on complex formation reactions of dichlorido[(R,R)-trans-1,2-diaminocyclohexane]platinum(II) complex with ligands of biological significance

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

The hydrolysis and complex formation equilibria of [Pt(dach)(H2O)2]2+, where dach is (R,R)-trans-1,2-diaminocyclohexane, with some sulfur- and nitrogen-bonding ligands, such as l-methionine, glutathione, inosine, inosine-5′-monophosphate, and guanosine-5′-monophosphate, were studied in aqueous 0.10 M NaClO4 solution at 298 K by potentiometric titrations. The experimentally determined pK a values for the studied diaqua complex were 6.00 and 10.03, respectively. The acid dissociation constants of the ligands were also determined. The stoichiometry and stability constants of the formed complexes are reported, as well as the concentration distribution of the various complex species evaluated as a function of pH. In all studied systems, species with one coordinated molecule of ligand were detected. However, only in systems with l-methionine and inosine, complexes with two molecules of ligand directly coordinated to the Pt(II) ion were found. The results also show that glutathione formed the most stable complexes. These results could contribute to better understanding of the interactions between Pt(II) complexes and biologically significant molecules.

Graphical abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Rau T, van Eldik R (1996) In: Sigel A, Sigel H (eds) Metal ions in biological systems. Marcel Dekker, New York

    Google Scholar 

  2. Van Rijt SH, Sadler PJ (2009) Drug Discov Today 14:1089

    Article  Google Scholar 

  3. Lippert B (1999) Cisplatin, chemistry and biochemistry of a leading anticancer drug. Wiley, Zürich

    Book  Google Scholar 

  4. Wong E, Giandomenico CM (1999) Chem Rev 99:2451

    Article  CAS  Google Scholar 

  5. van Zutphen S, Reedijk J (2005) Coord Chem Rev 249:2845

    Article  Google Scholar 

  6. Reedijk J (2008) Platin Met Rev 52:2

    Article  CAS  Google Scholar 

  7. Dor RT (1996) Platinum and other metal coordination compounds in cancer chemotherapy. Plenum, New York

    Google Scholar 

  8. Kelland LR (2000) In: Kelland LR, Farrell NP (eds) Platinum-based drugs in cancer therapy. Humana, Totowa

    Chapter  Google Scholar 

  9. Yongwon J, Lippard SJ (2007) Chem Rev 107:1387

    Article  Google Scholar 

  10. Reedijk J (1999) Chem Rev 99:2499

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. Teuben JM, Rodriguez i Zubiri M, Reedijk J (2000) Dalton Trans, p 369

  13. Bose RN, Moghaddas S, Weaver EL, Cox EH (1995) Inorg Chem 34:5878

    Article  CAS  Google Scholar 

  14. Barnham KJ, Djuran MI, Murdoch PS, Sadler PJ (1994) Chem Comm 6:721

    Article  Google Scholar 

  15. Barnham KJ, Djuran MI, Murdoch PS, Ranford JD, Sadler PJ (1996) Inorg Chem 35:1065

    Article  CAS  Google Scholar 

  16. Frey U, Ranford JD, Sadler PJ (1993) Inorg Chem 32:1333

    Article  CAS  Google Scholar 

  17. Lempers ELM, Reedijk J (1991) Adv Inorg Chem 37:175

    Article  CAS  Google Scholar 

  18. Van Boom SSGE, Chen BW, Teuben JM, Reedijk J (1999) Inorg Chem 38:1450

    Article  Google Scholar 

  19. Soldatović T, Bugarčić ŽD (2005) J Inorg Biochem 99:1472

    Article  Google Scholar 

  20. Marchan V, Moreno V, Pedroso E, Grandas A (2001) Chem Eur J 7:808

    Article  CAS  Google Scholar 

  21. Suchankova T, Vojtiskova M, Reedijk J, Brabec V, Kasparkova J (2009) J Biol Inorg Chem 14:75

    Article  CAS  Google Scholar 

  22. Roy S, Westmaas JA, Hagen KD, van Wezel GP, Reedijk J (2009) J Biol Inorg Chem 103:1288

    CAS  Google Scholar 

  23. Łakomska I, Kooijman H, Spek AL, Shen WZ, Reedijk J (2009) Dalton Trans, p 10736

  24. Todd RC, Lippard SJ (2009) Metallomics 1:280

    Article  CAS  Google Scholar 

  25. Abramkin SA, Jungwirth U, Valiahdi SM, Dworak C, Habala L, Meelich K, Berger W, Jakupec MA, Hartinger CG, Nazarov AA, Galanski M, Keppler BK (2010) J Med Chem 53:7356

    Article  CAS  Google Scholar 

  26. Summa N, Schiessl W, Puchta R, van Eikema Hommes H, van Eldik R (2006) Inorg Chem 45:2948

    Article  CAS  Google Scholar 

  27. Bugarčić ŽD, Petrović BV, Jelić R (2001) Trans Met Chem 26:668

    Article  Google Scholar 

  28. Jaganyi D, Hofmann A, van Eldik R (2001) Angew Chem Int Ed 40:1680

    Article  CAS  Google Scholar 

  29. Bugarčić ŽD, Soldatović T, Jelić R, Algueró B, Grandas A (2004) Dalton Trans, p 3869

  30. Küng A, Strickmann DB, Galanski M, Keppler BK (2001) J Inorg Biochem 86:691

    Article  Google Scholar 

  31. Petrovic D, Stojimirovic B, Petrovic B, Bugarcic ZM, Bugarcic ZD (2007) Bioorg Med Chem 15:4203

    Article  CAS  Google Scholar 

  32. Djuran MI, Lampers ELM, Reedijk J (1991) J Inorg Chem 30:2648

    Article  CAS  Google Scholar 

  33. Shoukry MM, van Eldik R (1996) Dalton Trans 2373

  34. Bugarčić ŽD, Heinemann FW, van Eldik R (2004) Dalton Trans, p 279

  35. Soldatović T, Bugarčić ŽD, van Eldik R (2009) p 4526

  36. Cubo L, Pizarro AM, Quiroga AG, Salassa L, Navarro-Ranninger C, Sadler PJ (2010) 104:909

  37. Vollano JF, Al-Baker S, Dobrowiak JC, Schurig JE (1987) J Med Chem 30:716

    Article  CAS  Google Scholar 

  38. Appleton TG, Hall JR, Ralph SF, Thompson CSM (1984) Inorg Chem 23:3521

    Article  CAS  Google Scholar 

  39. Gans P, Sabatini A, Vacca A (1996) Talanta 43:1739

    Article  CAS  Google Scholar 

  40. Alderighi L, Gans P, Ienco A, Peters D, Sabatini A, Vacca A (1999) Coord Chem Rev 184:311

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge financial support from the Ministry of Science of the Republic of Serbia (projects no. 172011 and 172016).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Biljana Petrović.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jelić, R., Marković, S. & Petrović, B. Equilibrium studies on complex formation reactions of dichlorido[(R,R)-trans-1,2-diaminocyclohexane]platinum(II) complex with ligands of biological significance. Monatsh Chem 142, 985–992 (2011). https://doi.org/10.1007/s00706-011-0553-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-011-0553-z

Keywords

Navigation