Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2017 (2017), Article ID 2562780, 9 pages
https://doi.org/10.1155/2017/2562780
Research Article

Synthesis, Characterization, Cytotoxic Activity, and Interactions with CT-DNA and BSA of Cationic Ruthenium(II) Complexes Containing Dppm and Quinoline Carboxylates

1Instituto de Química, Universidade Federal de Uberlândia, 38400-902 Uberlândia, MG, Brazil
2Departamento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil
3Universidade de Franca, 14404-600 Franca, SP, Brazil

Correspondence should be addressed to Gustavo Von Poelhsitz; rb.ufu@ztishleopovatsug

Received 6 March 2017; Revised 30 May 2017; Accepted 13 June 2017; Published 26 July 2017

Academic Editor: Claudio Pettinari

Copyright © 2017 Edinaldo N. da Silva et al. 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. S. Dasari and P. B. Tchounwou, “Cisplatin in cancer therapy: molecular mechanisms of action,” European Journal of Pharmacology, vol. 740, pp. 364–378, 2014. View at Publisher · View at Google Scholar
  2. N. J. Wheate, S. Walker, G. E. Craig, and R. Oun, “The status of platinum anticancer drugs in the clinic and in clinical trials,” Dalton Transactions, vol. 39, no. 35, pp. 8113–8127, 2010. View at Publisher · View at Google Scholar · View at Scopus
  3. K. D. Mjos and C. Orvig, “Metallodrugs in medicinal inorganic chemistry,” Chemical Reviews, vol. 114, no. 8, pp. 4540–4563, 2014. View at Publisher · View at Google Scholar · View at Scopus
  4. S. Gómez-Ruiz, D. Maksimović-Ivanić, S. Mijatović, and G. N. Kaluđerović, “On the discovery, biological effects, and use of cisplatin and metallocenes in anticancer chemotherapy,” Bioinorganic Chemistry and Applications, vol. 2012, Article ID 140284, 14 pages, 2012. View at Publisher · View at Google Scholar
  5. C. G. Hartinger, S. Zorbas-Seifried, M. A. Jakupec, B. Kynast, H. Zorbas, and B. K. Keppler, “From bench to bedside - preclinical and early clinical development of the anticancer agent indazolium trans-[tetrachlorobis(1H-indazole)ruthenate(III)] (KP1019 or FFC14A),” Journal of Inorganic Biochemistry, vol. 100, no. 5-6, pp. 891–904, 2006. View at Publisher · View at Google Scholar · View at Scopus
  6. W. H. Ang, A. Casini, G. Sava, and P. J. Dyson, “Organometallic ruthenium-based antitumor compounds with novel modes of action,” Journal of Organometallic Chemistry, vol. 696, no. 5, pp. 989–998, 2011. View at Publisher · View at Google Scholar · View at Scopus
  7. A. Bergamo, C. Gaiddon, J. H. Schellens, J. H. Beijnen, and G. Sava, “Approaching tumour therapy beyond platinum drugs: status of the art and perspectives of ruthenium drug candidates,” Journal of Inorganic Biochemistry, vol. 106, no. 1, pp. 90–99, 2012. View at Publisher · View at Google Scholar
  8. V. Moreno, J. Lorenzo, F. X. Aviles et al., “Studies of the antiproliferative activity of ruthenium (II) Cyclopentadienyl-derived complexes with nitrogen coordinated ligands,” Bioinorganic Chemistry and Applications, vol. 2010, Article ID 936834, 11 pages, 2010. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Pillozzi, L. Gasparoli, M. Stefanini et al., “NAMI-A is highly cytotoxic toward leukaemia cell lines: Evidence of inhibition of KCa 3.1 channels,” Dalton Transactions, vol. 43, no. 32, pp. 12150–12155, 2014. View at Publisher · View at Google Scholar · View at Scopus
  10. R. Trondl, P. Heffeter, C. R. Kowol, M. A. Jakupec, W. Berger, and B. K. Keppler, “NKP-1339, the first ruthenium-based anticancer drug on the edge to clinical application,” Chemical Science, vol. 5, no. 8, pp. 2925–2932, 2014. View at Publisher · View at Google Scholar
  11. C. G. Hartinger, M. A. Jakupec, S. Zorbas-Seifried et al., “KP1019, a new redox-active anticancer agent—preclinical development and results of a clinical phase I study in tumor patients,” Chemistry and Biodiversity, vol. 5, no. 10, pp. 2140–2155, 2008. View at Publisher · View at Google Scholar · View at Scopus
  12. M. Oszajca, E. Kuliś, G. Stochel, and M. Brindell, “Interaction of the NAMI-A complex with nitric oxide under physiological conditions,” New Journal of Chemistry, vol. 38, no. 8, pp. 3386–3394, 2014. View at Publisher · View at Google Scholar · View at Scopus
  13. F. R. Pavan, G. V. Poelhsitz, F. B. do Nascimento et al., “Ruthenium (II) phosphine/picolinate complexes as antimycobacterial agents,” European Journal of Medicinal Chemistry, vol. 45, no. 2, pp. 598–601, 2010. View at Publisher · View at Google Scholar · View at Scopus
  14. F. R. Pavan, G. V. Poelhsitz, L. V. P. da Cunha et al., “In vitro and in vivo activities of ruthenium(II) phosphine/diimine/picolinate complexes (SCAR) against Mycobacterium tuberculosis,” PLoS ONE, vol. 8, no. 5, Article ID e64242, 2013. View at Publisher · View at Google Scholar · View at Scopus
  15. T. M. P. Pagoto, L. L. G. Sobrinho, A. E. Graminha et al., “A ruthenium(II) complex with the propionate ion: Synthesis, characterization and cytotoxic activity,” Comptes Rendus Chimie, vol. 18, no. 12, pp. 1313–1319, 2015. View at Publisher · View at Google Scholar · View at Scopus
  16. J. C. S. Lopes, J. L. Damasceno, P. F. Oliveira et al., “Ruthenium(II) Complexes containing anti-inflammatory drugs as ligands: synthesis, characterization and in vitro cytotoxicity activities on cancer cell lines,” Journal of the Brazilian Chemical Society, vol. 26, no. 9, pp. 1838–1847, 2015. View at Publisher · View at Google Scholar · View at Scopus
  17. B. P. Sullivan and T. J. Meyer, “Comparisons of the physical and chemical properties of isomeric pairs. 2. Photochemical, thermal, and electrochemical cis-trans isomerizations of M(Ph2PCH2PPh2)2Cl2 (M = RuII, OsII),” Inorganic Chemistry, vol. 21, no. 3, pp. 1037–1040, 1982. View at Publisher · View at Google Scholar · View at Scopus
  18. W. J. Geary, “The use of conductivity measurements in organic solvents for the characterisation of coordination compounds,” Coordination Chemistry Reviews, vol. 7, no. 1, pp. 81–122, 1971. View at Publisher · View at Google Scholar · View at Scopus
  19. E. Fredericq, A. Oth, and F. Fontaine, “The ultraviolet spectrum of deoxyribonucleic acids and their constituents,” Journal of Molecular Biology, vol. 3, no. 1, pp. 11–17, 1961. View at Publisher · View at Google Scholar
  20. E. Gratton, N. Silva, G. Mei, N. Rosato, I. Savini, and A. Finazzi‐Agro, “Fluorescence lifetime distribution of folded and unfolded proteins,” International Journal of Quantum Chemistry, vol. 42, no. 5, pp. 1479–1489, 1992. View at Publisher · View at Google Scholar · View at Scopus
  21. J. A. Robson, F. Gonzàlez De Rivera, K. A. Jantan et al., “Bifunctional chalcogen linkers for the stepwise generation of multimetallic assemblies and functionalized nanoparticles,” Inorganic Chemistry, vol. 55, no. 24, pp. 12982–12996, 2016. View at Publisher · View at Google Scholar · View at Scopus
  22. M. C. Barral, R. Jiménez-Aparicio, E. C. Royer et al., “Synthesis and crystal structure of a ruthenium complex containing two monodentate DPPM ligands (DPPM = bis(diphenylphosphino)methane),” Inorganica Chimica Acta, vol. 209, no. 1, pp. 105–109, 1993. View at Publisher · View at Google Scholar · View at Scopus
  23. K. Nakamoto, Infrared and Raman Spectra of Inorganic and Coordination Compounds, Wiley-Interscience, New York, NY, USA, 5th edition, 1997.
  24. W. Lewandowski, M. Kalinowska, and H. Lewandowska, “The influence of metals on the electronic system of biologically important ligands. Spectroscopic study of benzoates, salicylates, nicotinates and isoorotates. Review,” Journal of Inorganic Biochemistry, vol. 99, no. 7, pp. 1407–1423, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. P. Lincoln, E. Tuite, and B. Norden, “Short-circuiting the molecular wire: cooperative binding of Δ-[Ru(phen)2dppz]2+ and Δ-[Rh(phi)2bipy]3+ to DNA,” Journal of the American Chemical Society, vol. 119, no. 6, pp. 1454-1455, 1997. View at Publisher · View at Google Scholar · View at Scopus
  26. V. I. Ivanov, L. E. Minchenkova, A. K. Schyolkina, and A. I. Poletayev, “Different conformations of double-stranded nucleic acid in solution as revealed by circular dichroism,” Biopolymers, vol. 12, no. 1, pp. 89–110, 1973. View at Publisher · View at Google Scholar · View at Scopus
  27. B. Norden and F. Tjerneld, “Structure of methylene blue-DNA complexes studied by linear and circular dichroism spectroscopy,” Biopolymers, vol. 21, no. 9, pp. 1713–1734, 1982. View at Publisher · View at Google Scholar · View at Scopus
  28. P. Uma Maheswari and M. Palaniandavar, “DNA binding and cleavage properties of certain tetrammine ruthenium(II) complexes of modified 1,10-phenanthrolines - Effect of hydrogen-bonding on DNA-binding affinity,” Journal of Inorganic Biochemistry, vol. 98, no. 2, pp. 219–230, 2004. View at Publisher · View at Google Scholar · View at Scopus
  29. F. Dimiza, A. N. Papadopoulos, V. Tangoulis et al., “Biological evaluation of cobalt(II) complexes with non-steroidal anti-inflammatory drug naproxen,” Journal of Inorganic Biochemistry, vol. 107, no. 1, pp. 54–64, 2012. View at Publisher · View at Google Scholar · View at Scopus
  30. L. Shang, Y. Wang, J. Jiang, and S. Dong, “PH-dependent protein conformational changes in albumin:Gold nanoparticle bioconjugates: a spectroscopic study,” Langmuir, vol. 23, no. 5, pp. 2714–2721, 2007. View at Publisher · View at Google Scholar · View at Scopus
  31. M. Ganeshpandian, R. Loganathan, E. Suresh, A. Riyasdeen, M. A. Akbarsha, and M. Palaniandavar, “New ruthenium(II) arene complexes of anthracenyl-appended diazacycloalkanes: effect of ligand intercalation and hydrophobicity on DNA and protein binding and cleavage and cytotoxicity,” Dalton Transactions, vol. 43, no. 3, pp. 1203–1219, 2014. View at Publisher · View at Google Scholar · View at Scopus
  32. X. Zhao, R. Liu, Z. Chi, Y. Teng, and P. Qin, “New insights into the behavior of bovine serum albumin adsorbed onto carbon nanotubes: comprehensive spectroscopic studies,” Journal of Physical Chemistry B, vol. 114, no. 16, pp. 5625–5631, 2010. View at Publisher · View at Google Scholar · View at Scopus
  33. R. S. Correa, K. M. Oliveira, H. Pérez et al., “cis-bis(N-benzoyl-N',N'-dibenzylthioureido)platinum(II): Synthesis, molecular structure and its interaction with human and bovine serum albumin,” Arabian Journal of Chemistry, vol. 2015, 2015. View at Publisher · View at Google Scholar · View at Scopus
  34. R. S. Correa, K. M. De Oliveira, F. G. Delolo et al., “Ru(II)-based complexes with N-(acyl)-N′,N′-(disubstituted)thiourea ligands: synthesis, characterization, BSA- and DNA-binding studies of new cytotoxic agents against lung and prostate tumour cells,” Journal of Inorganic Biochemistry, vol. 150, article 9708, pp. 63–71, 2015. View at Publisher · View at Google Scholar · View at Scopus
  35. L. Colina-Vegas, J. L. Dutra, W. Villarreal et al., “Ru(II)/clotrimazole/diphenylphosphine/bipyridine complexes: Interaction with DNA, BSA and biological potential against tumor cell lines and Mycobacterium tuberculosis,” Journal of Inorganic Biochemistry, vol. 162, pp. 135–145, 2016. View at Publisher · View at Google Scholar · View at Scopus
  36. M. Mathew, S. Sreedhanya, P. Manoj, C. T. Aravindakumar, and U. K. Aravind, “Exploring the interaction of bisphenol-S with serum albumins: a better or worse alternative for bisphenol A?” Journal of Physical Chemistry B, vol. 118, no. 14, pp. 3832–3843, 2014. View at Publisher · View at Google Scholar · View at Scopus
  37. B. Ojha and G. Das, “The interaction of 5-(Alkoxy)naphthalen-1-amine with bovine serum albumin and Its effect on the conformation of protein,” Journal of Physical Chemistry B, vol. 114, no. 11, pp. 3979–3986, 2010. View at Publisher · View at Google Scholar · View at Scopus
  38. S.-L. Zhang, G. L. V. Damu, L. Zhang, R.-X. Geng, and C.-H. Zhou, “Synthesis and biological evaluation of novel benzimidazole derivatives and their binding behavior with bovine serum albumin,” European Journal of Medicinal Chemistry, vol. 55, pp. 164–175, 2012. View at Publisher · View at Google Scholar · View at Scopus
  39. P. D. Ross and S. Subramanian, “Thermodynamics of protein association reactions: forces contributing to stability,” Biochemistry, vol. 20, no. 11, pp. 3096–3102, 1981. View at Publisher · View at Google Scholar · View at Scopus