Table of Contents Author Guidelines Submit a Manuscript
Journal of Chemistry
Volume 2013 (2013), Article ID 892052, 14 pages
http://dx.doi.org/10.1155/2013/892052
Research Article

Insights into the Intramolecular Properties of η6-Arene-Ru-Based Anticancer Complexes Using Quantum Calculations

Department of Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700, South Africa

Received 21 May 2013; Revised 23 July 2013; Accepted 23 July 2013

Academic Editor: James W. Gauld

Copyright © 2013 Adebayo A. Adeniyi and Peter A. Ajibade. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. E. Meggers, “Targeting proteins with metal complexes,” Chemical Communications, no. 9, pp. 1001–1010, 2009. View at Publisher · View at Google Scholar · View at Scopus
  2. C. S. Allardyce, A. Dorcier, C. Scolaro, and P. J. Dyson, “Development of organometallic (organo-transition metal) pharmaceuticals,” Applied Organometallic Chemistry, vol. 19, no. 1, pp. 1–10, 2005. View at Publisher · View at Google Scholar · View at Scopus
  3. P. J. Dyson and G. Sava, “Metal-based antitumour drugs in the post genomic era,” Dalton Transactions, no. 16, pp. 1929–1933, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. Y. N. V. Gopal, D. Jayaraju, and A. K. Kondapi, “Inhibition of topoisomerase II catalytic activity by two ruthenium compounds: a ligand-dependent mode of action,” Biochemistry, vol. 38, no. 14, pp. 4382–4388, 1999. View at Publisher · View at Google Scholar · View at Scopus
  5. C. S. K. Rajapakse, A. Martínez, B. Naoulou et al., “Synthesis, characterization, and in vitro antimalarial and antitumor activity of new ruthenium(II) complexes of chloroquine,” Inorganic Chemistry, vol. 48, no. 3, pp. 1122–1131, 2009. View at Publisher · View at Google Scholar · View at Scopus
  6. M. Groessl, Y. O. Tsybin, C. G. Hartinger, B. K. Keppler, and P. J. Dyson, “Ruthenium versus platinum: interactions of anticancer metallodrugs with duplex oligonucleotides characterised by electrospray ionisation mass spectrometry,” Journal of Biological Inorganic Chemistry, vol. 15, no. 5, pp. 677–688, 2010. View at Publisher · View at Google Scholar · View at Scopus
  7. B. Dutta, R. Scopelliti, and K. Severin, “Synthesis, structure, and reactivity of the methoxy-bridged dimer [CpRu(μ-OMe)]2 (Cp = η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl),” Organometallics, vol. 27, no. 3, pp. 423–429, 2008. View at Publisher · View at Google Scholar · View at Scopus
  8. B. Dutta, C. Scolaro, R. Scopelliti, P. J. Dyson, and K. Severin, “Importance of the π-ligand: remarkable effect of the cyclopentadienyl ring on the cytotoxicity of ruthenium PTA compounds,” Organometallics, vol. 27, no. 7, pp. 1355–1357, 2008. View at Publisher · View at Google Scholar · View at Scopus
  9. W. H. Ang and P. J. Dyson, “Classical and non-classical ruthenium-based anticancer drugs: towards targeted chemotherapy,” European Journal of Inorganic Chemistry, no. 20, pp. 4003–4018, 2006. View at Publisher · View at Google Scholar · View at Scopus
  10. G. Gasser, I. Ott, and N. Metzler-Nolte, “Organometallic anticancer compounds,” Journal of Medicinal Chemistry, vol. 54, no. 1, pp. 3–25, 2011. View at Publisher · View at Google Scholar · View at Scopus
  11. S. Betanzos-Lara, L. Salassa, A. Habtemariam et al., “Photoactivatable organometallic pyridyl ruthenium(II) arene complexes,” Organometallics, vol. 31, no. 9, pp. 3466–3479, 2012. View at Google Scholar
  12. E. A. Hillard and G. Jaouen, “Bioorganometallics: future trends in drug discovery, analytical chemistry, and catalysis,” Organometallics, vol. 30, no. 1, pp. 20–27, 2011. View at Publisher · View at Google Scholar · View at Scopus
  13. E. A. Meyer, R. K. Castellano, and F. Diederich, “Interactions with aromatic rings in chemical and biological recognition,” Angewandte Chemie, vol. 42, no. 11, pp. 1210–1250, 2003. View at Publisher · View at Google Scholar · View at Scopus
  14. I. Alkorta, F. Blanco, and J. Elguero, “Simultaneous interaction of tetrafluoroethene with anions and hydrogen-bond donors: a cooperativity study,” Journal of Chemical Theory and Computation, vol. 5, no. 4, pp. 1186–1194, 2009. View at Publisher · View at Google Scholar · View at Scopus
  15. J. A. Platts, J. Overgaard, C. Jones, B. B. Iversen, and A. Stasch, “First experimental characterization of a non-nuclear attractor in a dimeric magnesium(I) compound,” Journal of Physical Chemistry A, vol. 115, no. 2, pp. 194–200, 2011. View at Publisher · View at Google Scholar · View at Scopus
  16. I. M. Kapetanovic, “Computer-aided drug discovery and development (CADDD): in silico-chemico-biological approach,” Chemico-Biological Interactions, vol. 171, no. 2, pp. 165–176, 2008. View at Publisher · View at Google Scholar · View at Scopus
  17. Y. Duan, C. Wu, S. Chowdhury et al., “A point-charge force field for molecular mechanics simulations of proteins based on condensed-phase quantum mechanical calculations,” Journal of Computational Chemistry, vol. 24, no. 16, pp. 1999–2012, 2003. View at Publisher · View at Google Scholar · View at Scopus
  18. N. Rai, S. P. Tiwari, and E. J. Maginn, “Force field development for actinyl ions via quantum mechanical calculations: an approach to account for many body solvation effects,” Journal of Physical Chemistry B, vol. 116, pp. 10885–10897, 2012. View at Google Scholar
  19. K. Cobb, “Dock this: drug design feeds drug development,” Biomedical Computation Review, pp. 20–30, 2007. View at Google Scholar
  20. A. L. Harvey, “Natural products in drug discovery,” Drug Discovery Today, vol. 13, no. 19-20, pp. 894–901, 2008. View at Publisher · View at Google Scholar · View at Scopus
  21. S. Chatterjee, S. Kundu, A. Bhattacharyya, C. G. Hartinger, and P. J. Dyson, “The ruthenium(II)-arene compound RAPTA-C induces apoptosis in EAC cells through mitochondrial and p53-JNK pathways,” Journal of Biological Inorganic Chemistry, vol. 13, no. 7, pp. 1149–1155, 2008. View at Publisher · View at Google Scholar · View at Scopus
  22. A. E. Egger, C. G. Hartinger, A. K. Renfrew, and P. J. Dyson, “Metabolization of [Ru(η6-C6H5CF 3)(pta)Cl2]: a cytotoxic RAPTA-type complex with a strongly electron withdrawing arene ligand,” Journal of Biological Inorganic Chemistry, vol. 15, no. 6, pp. 919–927, 2010. View at Publisher · View at Google Scholar · View at Scopus
  23. M. Hanif, H. Henke, S. M. Meier et al., “Is the reactivity of M(II)-arene complexes of 3-hydroxy-2(1 H)-pyridones to biomolecules the anticancer activity determining parameteŕ,” Inorganic Chemistry, vol. 49, no. 17, pp. 7953–7963, 2010. View at Publisher · View at Google Scholar · View at Scopus
  24. F. Wang, A. Habtemariam, E. P. L. van der Geer et al., “Controlling ligand substitution reactions of organometallic complexes: tuning cancer cell cytotoxicity,” Proceedings of the National Academy of Sciences of the United States of America, vol. 102, no. 51, pp. 18269–18274, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. A. García-Fernández, J. Díez, M. P. Gamasa, and E. Lastra, “Facile modification of 1,3,5-triaza-7-phosphatricyclo[3.3.1.1 3,7]decane phosphanes coordinated to ruthenium(II),” Inorganic Chemistry, vol. 48, no. 6, pp. 2471–2481, 2009. View at Publisher · View at Google Scholar · View at Scopus
  26. W. H. Ang, E. Daldini, C. Scolaro, R. Scopelliti, L. Juillerat-Jeannerat, and P. J. Dyson, “Development of organometallic ruthenium-arene anticancer drugs that resist hydrolysis,” Inorganic Chemistry, vol. 45, no. 22, pp. 9006–9013, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. C. Adamo and V. Barone, “Toward reliable density functional methods without adjustable parameters: the PBE0 model,” Journal of Chemical Physics, vol. 110, no. 13, pp. 6158–6170, 1999. View at Google Scholar · View at Scopus
  28. W. J. Stevens, M. Krauss, H. Basch, and P. G. Jasien, “Relativistic compact effective potentials and efficient, shared-exponent basis sets for the third-, fourth-, and fifth-row atoms,” Canadian Journal of Chemistry, vol. 70, pp. 612–630, 1992. View at Google Scholar
  29. D. Feller, “The role of databases in support of computational chemistry calculations,” Journal of Computational Chemistry, vol. 17, no. 13, pp. 1571–1586, 1996. View at Google Scholar · View at Scopus
  30. K. L. Schuchardt, B. T. Didier, T. Elsethagen et al., “Basis set exchange: a community database for computational sciences,” Journal of Chemical Information and Modeling, vol. 47, no. 3, pp. 1045–1052, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. R. Marchal, P. Carbonnière, D. Begue, and C. Pouchan, “Structural and vibrational determination of small gallium-arsenide clusters from CCSD(T) and DFT calculations,” Chemical Physics Letters, vol. 453, no. 1–3, pp. 49–54, 2008. View at Publisher · View at Google Scholar · View at Scopus
  32. R. Marchal, P. Carbonnière, and C. Pouchan, “Structural and vibrational properties prediction of SnnTen clusters (n = 2-8) using the GSAM approach,” Computational and Theoretical Chemistry, vol. 990, pp. 100–105, 2012. View at Google Scholar
  33. A. D. Becke, “Density-functional thermochemistry. III. The role of exact exchange,” The Journal of Chemical Physics, vol. 98, no. 7, pp. 5648–5652, 1993. View at Google Scholar · View at Scopus
  34. K. D. Dobbs and W. J. Hehre, “Molecular orbital theory of the properties of inorganic and organometallic compounds 5. Extended basis sets for first-row transition metals,” Journal of Computational Chemistry, vol. 6, pp. 861–879, 1987. View at Google Scholar
  35. A. A. Granovsky, “Firefly version 7. 1.G,” http://classic.chem.msu.su/gran/firefly/index.html.
  36. M. W. Schmidt, K. K. Baldridge, J. A. Boatz et al., “General atomic and molecular electronic structure system,” Journal of Computational Chemistry, vol. 14, no. 11, pp. 1347–1363, 1993. View at Google Scholar
  37. M. J. Frisch, G. W. Trucks, H. B. Schlegel et al., G03a: GAUSSIAN03, Revision D. 01, Gaussian, Wallingford, UK, 2009.
  38. T. A. Keith, “AIMAll (Version 12. 06. 03),” Overland Park, Kan, USA, TK Gristmill Software, 2012, http://aim.tkgristmill.com.
  39. A. E. Reed, L. A. Curtiss, and F. Weinhold, “Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint,” Chemical Reviews, vol. 88, no. 6, pp. 899–926, 1988. View at Google Scholar · View at Scopus
  40. J. P. Foster and F. Weinhold, “Natural hybrid orbitals,” Journal of the American Chemical Society, vol. 102, no. 24, pp. 7211–7218, 1980. View at Google Scholar · View at Scopus
  41. E. D. Glendening and A. Streitwieser, “Natural energy decomposition analysis: an energy partitioning procedure for molecular interactions with application to weak hydrogen bonding, strong ionic, and moderate donor-acceptor interactions,” The Journal of Chemical Physics, vol. 100, no. 4, pp. 2900–2909, 1994. View at Google Scholar · View at Scopus
  42. Z. Chval, Z. Futera, and J. V. Burda, “Comparison of hydration reactions for “piano-stool” RAPTA-B and [Ru(η6- Arene)(en)Cl]+ complexes: density functional theory computational study,” Journal of Chemical Physics, vol. 134, no. 2, Article ID 024520, 2011. View at Publisher · View at Google Scholar · View at Scopus
  43. I. C. de Silva, R. M. de Silva, and K. M. N. de Silva, “Investigations of nonlinear optical (NLO) properties of Fe, Ru and Os organometallic complexes using high accuracy density functional theory (DFT) calculations,” Journal of Molecular Structure, vol. 728, no. 1–3, pp. 141–145, 2005. View at Publisher · View at Google Scholar · View at Scopus
  44. P. J. Mendes, J. P. Prates Ramalho, A. J. E. Candeias, M. P. Robalo, and M. H. Garcia, “Density functional theory calculations on η5- monocyclopentadienylnitrilecobalt complexes concerning their second-order nonlinear optical properties,” Journal of Molecular Structure, vol. 729, no. 1-2, pp. 109–113, 2005. View at Publisher · View at Google Scholar · View at Scopus
  45. I. N. Stepanenko, A. Casini, F. Edafe et al., “Conjugation of organoruthenium(ii) 3-(1h-benzimidazol-2 yl)pyrazolo[3,4-b]pyridines and indolo[3,2-d]benzazepines to recombinant human serum albumin: a strategy to enhance cytotoxicity in cancer cells,” Inorganic Chemistry, vol. 50, no. 24, pp. 12669–12679, 2011. View at Publisher · View at Google Scholar · View at Scopus
  46. M. J. Calhorda and P. E. M. Lopes, “An “atoms in molecules” (AIM) analysis of the dihydrogen bond in organometallic compounds,” Journal of Organometallic Chemistry, vol. 609, no. 1-2, pp. 53–59, 2000. View at Google Scholar · View at Scopus
  47. D. Tiana, Organometallic Chemistry from the Interacting Quantum Atoms Approach [Ph.D. thesis], Università degli Studi di Milano, Milan, Italy, 2009/2010.
  48. I. Rozas, I. Alkorta, and J. Elguero, “Behavior of ylides containing N, O, and C atoms as hydrogen bond acceptors,” Journal of the American Chemical Society, vol. 122, no. 45, pp. 11154–11161, 2000. View at Publisher · View at Google Scholar · View at Scopus
  49. I. Alkorta, I. Rozas, and J. Elguero, “Non-conventional hydrogen bonds,” Chemical Society Reviews, vol. 27, no. 2, pp. 163–170, 1998. View at Google Scholar · View at Scopus
  50. S. Hammerum, “Alkyl radicals as hydrogen bond acceptors: computational evidence,” Journal of the American Chemical Society, vol. 131, no. 24, pp. 8627–8635, 2009. View at Publisher · View at Google Scholar · View at Scopus
  51. J. E. D. Bene, I. Alkorta, G. Sanchez-Sanz, and J. Elguero, “Variations in the structures and binding energies of binary complexes with HBO,” Chemical Physics Letters, vol. 538, pp. 5–9, 2012. View at Google Scholar
  52. K. Tang and F. Q. Shi, “Comparative analysis of blue-shifted hydrogen bond versus conventional hydrogen bond in methyl radical complexes,” International Journal of Quantum Chemistry, vol. 107, no. 3, pp. 665–669, 2007. View at Publisher · View at Google Scholar · View at Scopus
  53. E. S. Shubina, N. V. Belkova, and L. M. Epstein, “Novel types of hydrogen bonding with transition metal π-complexes and hydrides,” Journal of Organometallic Chemistry, vol. 536-537, pp. 17–29, 1997. View at Google Scholar · View at Scopus
  54. M. Solimannejad, M. Malekani, and I. Alkorta, “Theoretical study of the halogen-hydride complexes between XeH2 and carbon halogenated derivatives,” Journal of Molecular Structure, vol. 955, no. 1–3, pp. 140–144, 2010. View at Publisher · View at Google Scholar · View at Scopus
  55. L. J. Farrugia and H. M. Senn, “On the unusual weak intramolecular CC interactions in Ru3(CO)12: a case of bond path artifacts introduced by the multipole model?” Journal of Physical Chemistry A, vol. 116, no. 1, pp. 738–746, 2012. View at Publisher · View at Google Scholar · View at Scopus
  56. Q. K. Timerghazin, I. Rizvi, and G. H. Peslherbe, “Can a dipole-bound electron form a pseudo-atom? An atoms-in-molecules study of the hydrated electron,” Journal of Physical Chemistry A, vol. 115, no. 45, pp. 13201–13209, 2011. View at Publisher · View at Google Scholar · View at Scopus
  57. K. E. Edgecombe, R. O. Esquivel, V. H. Smith Jr., and F. Müller-Plathe, “Pseudoatoms of the electron density,” The Journal of Chemical Physics, vol. 97, no. 4, pp. 2593–2599, 1992. View at Google Scholar · View at Scopus
  58. A. García-Fernández, J. Díez, Á. Manteca, J. Sánchez, M. P. Gamasa, and E. Lastra, “Novel hydridotris(pyrazolyl)borate ruthenium(II) complexes containing the water-soluble phosphane 1,3,5-triaza-7-phosphaadamantane: synthesis and evaluation of DNA binding properties,” Polyhedron, vol. 27, no. 4, pp. 1214–1228, 2008. View at Publisher · View at Google Scholar · View at Scopus