Non-Empirical Quantum Chemical Studies on Hydration of trans- and cis-[Pt(NH3)2Cl2]. Possible Role of Relativistic Effects

• Autorzy: Chojnacki H. , Kuduk-Jaworska J. , Jaroszewicz I. , Jański J. J.
• Języki publikacji: EN

Abstrakty

EN

The motivation to this work results from the recognition of cis-dia mminedi - chloroplatinum(II) (cisplatin) hydration processes as essential for the fate of this drug in host organism. Applying quantum chemical calculations, there were evaluated the first stages of water molecule impact on platinum complexes: cisplatin and its trans isomer. Non-empirical quantum chemical calculations have been performed for reactions of cisand trans-diamminedichloroplatinum(II) (transplatin) with the water molecule, as sum - ing the associative mode of reactions running with the addition of a fifth ligand to a square planar d8 complex and formation of a trigonal-bipyramidal structure of the transition state. For the obtained structures of reactants, transition states, and products, the ther mo - dynamic characteristics (energies and Gibbs free energies) were estimated. Energetics for the ligand exchange reactions were estimated both in gas phase and water solution by using the PCM model. The hydration reactions under consideration are principally endothermic except of the solvated transplatin. Basing on our ab in itio ZORA calculations, the possible role of relativistic effects in the reaction mechanism is pointed out as well. Ob - tained results may throw some light on processes which determine the inter change of pro-drug (cisplatin) into activated drug (aqua-form) and implicate their significance in de signing of anticancer, Pt-containing chemotherapeutics.

Słowa kluczowe

EN

cisplatin; transplatin; interactions with water molecule

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2009
• Tom: Vol. 83, nr 5
• Strony: 1013--1024
• Opis fizyczny: Bibliogr. 26 poz., rys.

Twórcy

autor

Chojnacki H.

autor

Kuduk-Jaworska J.

autor

Jaroszewicz I.

autor

Jański J. J.

• Institute of Physical and Theoretical Chemistry, Wrocław University of Technology, Wyb. Wyspiańskiego 27, 50-370 Wrocław, Poland,

Bibliografia

• 1. Cleare M.J. and Hoeschele J.H., Bioinorg. Chem., 2, 187 (1973).
• 2. 0'Dwyer P.J. and Stevenson J.P, Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug, Ed. B. Lippert, Wiley-VCH Weinheim, 1999, p. 31.
• 3. Rosenberg B., Naturwiss., 60, 399 (1973).
• 4. Reedijk J. and Teuben J.M., Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug, Ed. B. Lippert, Wiley-VCH Weinheim, 1999, p. 339.
• 5. Braddock P.D, Connors T.A, Jones N.. Khokhar A.R, Melzack D.H. and Tobe M.L, Chem. Biol. Interact., 11, 145 (1975).
• 6. Rosenberg B., Chemistry and Biochemistry of a Leading Anticancer Drug, Ed. B. Lippert, Wiley-VCH Weinheim, 1999, p. 3.
• 7. Hambley T.W, Coord. Chem. Rev., 166, 181 (1997).
• 8. Wang D. and Lippard S.J, Nat. Rev. Drug Disc, 4, 307 (2005).
• 9. Cleare M.J, Hydes P.C, Hepburn D.R. and Malerbi B.W, Cisplatin: Current Status and New Developments, Eds. A.W. Prestayko, S.T Crooke, S.K. Carter, Academic Press, London, 1980, p. 49.
• 10. Martin R.B, Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug, Ed. B. Lippert, Wiley-VCH, Weinheim, 1999, p. 183.
• 11. BloeminkM.J. and Reedijk J, Metal Ions Biol. Sys., 32, 641 (1996).
• 12. Lepre C.L. and Lippard S.J, Nucleic Acids and Molecular Biology, Eds. F. Eckstein, Lilley D.M.J., Springer-Verlag, Berlin-Heidelberg, 1990, vol. 4, p. 9.
• 13. Bancroft D.P, Lepre C.A. and Lippard S.J, J. Am. Chem. Soc, 112, 6860 (1990).
• 14. Miller S.E. and House DA, Inorg. Chim. Acta, 173, 53 (1990).
• 15. Miller S.E. and House DA, Inorg. Chim. Acta, 187, 125 (1991).
• 16. LeRoy A.F., Lutz R.T. and Dedrick R.L., Cancer Treat. Rep., 63, 59 (1979).
• 17. Hindmarsh K, House DA. and Turnbull M.M., Inorg. Chim. Acta, 257, 11 (1997).
• 18. Yotsuyanagi T, Usami M., Noda Y. and Nagata M, Int. J. Pharm., 246, 95 (2002).
• 19. Arpalahti J, Metal Ions Biol. Sys., 32, 379, (1996).
• 20. Mikola M. and Arpalahti J, Inorg. Chem., 33, 4439 (1994).
• 21. Kozelka J., Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug, Ed. Lippert B, Wiley-VCH Weinheim, 1999, p. 537.
• 22. Burda V, Sponer J. and Leszczyński J, Computational Chemistry: Reviews of Current Trends, Ed. J. Leszczyński, World Scientific, London, 2006, vol. 10, p. 265.
• 23. Burda J.V., Zeizinger M. and Leszczyński J, J. Comput. Chem., 26, 907 (2005).
• 24. Bradac O, Zimmermann T. and Burda J.V, J. Mol. Model., 14, 705 (2008).
• 25. Zhang Y, Guo Z. and You X-Z, J. Am. Chem. Soc, 123, 9378 (2001).
• 26. Burda J.V, Zeizinger M. and Leszczyński J, J. Chem. Phys., 120, 1253 (2004).
• 27. Deubel D.V., J. Am. Chem. Soc, 124, 5834 (2002).
• 28. Deubel D.V., J. Am. Chem. Soc, 126, 5999 (2004).
• 29. Chojnacki H, Kuduk-Jaworska J, Jaroszewicz I. and Jański J, J. Mol. Model. (2009) (proof).
• 30. Chval Z. and Sip M., J. Mol. Struct. (THEOCHEM), 532, 59 ( 2000).
• 31. Carloni P., Sprik Z. and Andreoni W, J. Phys. Chem., B104, 823 (2000).
• 32. Lopes J.F., Rocha W.R, Dos Santos H.F. and De Almeida W.B., J. Chem. Phys., 128,165103 (2008).
• 33. Raber J., Zhu Ch. and Eriksson L.A., Mol. Phys., 102, 2357 (2004).
• 34. <http://bse.pn.gov/bse.portal>.
• 35. Gaussian Basis Sets for Molecular Calculations, Ed. S. Huzinaga, Elsevier, Amsterdam, 1984.
• 36. <http://OpenMOPAC.net>.
• 37. GAUSSIAN-03, Rev. D-01 Gaussian Inc., Pittsburgh PA 2003.
• 38. Pantazis D, Chen X.-Y, Landis C.R. and Neese F, J. Chem. Theor. Comp., 4, 908 (2008).
• 39. Lempers E. and Reedijk J, Adv. Inorg. Chem., 37, 175 (1991).
• 40. Corden B.J., Inorg. Chim. Acta, 137, 125 (1987).
• 41. Hanigan M.H. and Devarajan P., Cancer Ther., 1, 47 (2003).
• 42. Wang X. and Guo Z., Anticanc. Agents Med. Chem., 7, 19 (2007).
• 43. Brabec V. and Kasparkova J, Drug Resistance Updates, 8, 131 (2005).
• 44. Milburn G.H.W. and Truter M.R, J. Chem. Soc, A, 1609 (1966).
• 45. Chojnacki H., unpublished results.
• 46. Burda J.V. and Gu J., J. Inorg. Biochem., 102, 53 (2008).