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Journal of Chemistry
Volume 2015 (2015), Article ID 963152, 8 pages
http://dx.doi.org/10.1155/2015/963152
Research Article

Mimicking Peroxidase Activity by a Manganese(II) Complex Involving a New Asymmetric Tetradentate Ligand Containing Both Amino and Imino Groups

Departamento de Química Inorgánica, Facultad de Ciencias, Universidade de Santiago de Compostela, 27002 Lugo, Spain

Received 30 September 2015; Accepted 8 December 2015

Academic Editor: Henryk Kozlowski

Copyright © 2015 Yolanda Pérez-Otero 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. B. Halliwell and J. M. C. Gutteridge, Free Radicals in Biology and Medicine, Oxford University Press, Oxford, UK, 4th edition, 2007.
  2. V. Calabrese, C. Cornelius, C. Mancuso et al., “Cellular stress response: a novel target for chemoprevention and nutritional neuroprotection in aging, neurodegenerative disorders and longevity,” Neurochemical Research, vol. 33, no. 12, pp. 2444–2471, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. M. M. Moschos, E. Nitoda, I. P. Chatziralli, and C. A. Demopoulos, “Age-related macular degeneration: pathogenesis, genetic background, and the role of nutritional supplements,” Journal of Chemistry, vol. 2014, Article ID 317536, 9 pages, 2014. View at Publisher · View at Google Scholar · View at Scopus
  4. B. Palenik, B. Brahamsha, F. W. Larimer et al., “The genome of a motile marine Synechococcus,” Nature, vol. 424, no. 6952, pp. 1037–1042, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. A. J. Wu, J. E. Penner-Hahn, and V. L. Pecoraro, “Structural, spectroscopic, and reactivity models for the manganese catalases,” Chemical Reviews, vol. 104, no. 2, pp. 903–938, 2004. View at Publisher · View at Google Scholar · View at Scopus
  6. S. R. Doctrow, M. Liesa, S. Melov, O. S. Shirihai, and P. Tofilon, “Salen Mn complexes are superoxide dismutase and catalase mimetics that protect the mitocondria,” Current Inorganic Chemistry, vol. 2, pp. 325–334, 2012. View at Google Scholar
  7. N. Gao, H. Li, Q. Li, J. Liu, and G. Luo, “Synthesis and kinetic evaluation of a trifunctional enzyme mimic with a dimanganese active centre,” Journal of Inorganic Biochemistry, vol. 105, no. 2, pp. 283–288, 2011. View at Publisher · View at Google Scholar · View at Scopus
  8. T. R. Simmons, G. Berggren, M. Bacchi, M. Fontecave, and V. Artero, “Mimicking hydrogenases: from biomimetics to artificial enzymes,” Coordination Chemistry Reviews, vol. 270-271, pp. 127–150, 2014. View at Publisher · View at Google Scholar · View at Scopus
  9. S. Signorella and C. Hureau, “Bioinspired functional mimics of the manganese catalases,” Coordination Chemistry Reviews, vol. 256, no. 11-12, pp. 1229–1245, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. D. Bani and A. Bencini, “Developing ROS scavenging agents for pharmacological purposes: recent advances in design of manganese-based complexes with anti-inflammatory and anti-nociceptive activity,” Current Medicinal Chemistry, vol. 19, no. 26, pp. 4431–4444, 2012. View at Publisher · View at Google Scholar · View at Scopus
  11. I. Batinić-Haberle, J. S. Rebouças, and I. Spasojević, “Superoxide dismutase mimics: chemistry, pharmacology, and therapeutic potential,” Antioxidants and Redox Signaling, vol. 13, no. 6, pp. 877–918, 2010. View at Publisher · View at Google Scholar · View at Scopus
  12. M. R. Bermejo, M. I. Fernández, A. M. González-Noya et al., “Novel peroxidase mimics: μ-aqua manganese-Schiff base dimers,” Journal of Inorganic Biochemistry, vol. 100, pp. 1470–1478, 2006. View at Google Scholar
  13. A. Vázquez-Fernández, M. R. Bermejo, M. I. Fernández-García, G. González-Riopedre, M. J. Rodríguez-Doutón, and M. Maneiro, “Influence of the geometry around the manganese ions on the peroxidase and the catalase activities of Mn(III)-Schiff base complexes,” Journal of Inorganic Biochemistry, vol. 105, pp. 1538–1547, 2011. View at Google Scholar
  14. G. González-Riopedre, M. I. Fernández-García, A. M. González-Noya, M. Á. Vázquez-Fernández, M. R. Bermejo, and M. Maneiro, “Manganese-Schiff base complexes as catalysts for water photolysis,” Physical Chemistry Chemical Physics, vol. 13, no. 40, pp. 18069–18077, 2011. View at Publisher · View at Google Scholar · View at Scopus
  15. G. González-Riopedre, M. R. Bermejo, M. I. Fernández-García et al., “Alkali-metal-ion-directed self-assembly of redox-active manganese(III) supramolecular boxes,” Inorganic Chemistry, vol. 54, no. 6, pp. 2512–2521, 2015. View at Publisher · View at Google Scholar
  16. R. Noyori and S. Hashiguchi, “Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes,” Accounts of Chemical Research, vol. 30, no. 2, pp. 97–102, 1997. View at Publisher · View at Google Scholar · View at Scopus
  17. Y. Rondelez, M.-N. Rager, A. Duprat, and O. Reinaud, “Calix[6]arene-based cuprous ‘funnel complexes’: a mimic for the substrate access channel to metalloenzyme active sites,” Journal of the American Chemical Society, vol. 124, no. 7, pp. 1334–1340, 2002. View at Publisher · View at Google Scholar · View at Scopus
  18. G. Zassinovich, G. Mestroni, and S. Gladiali, “Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts,” Chemical Reviews, vol. 92, no. 5, pp. 1051–1069, 1992. View at Publisher · View at Google Scholar · View at Scopus
  19. V. Alexander, “Design and synthesis of macrocyclic ligands and their complexes of lanthanides and actinides,” Chemical Reviews, vol. 95, no. 2, pp. 273–342, 1995. View at Publisher · View at Google Scholar · View at Scopus
  20. G. Kumar, R. Johari, and S. Devi, “Synthesis, physical characterization of M(III) transition metal complexes derived from thiodihydrazide and 5-tert-butyl-2-hydroxy-3-(3-phenylpent-3-yl) benzaldehyde,” E-Journal of Chemistry, vol. 9, no. 4, pp. 2119–2127, 2012. View at Publisher · View at Google Scholar · View at Scopus
  21. E. López-Torres and M. A. Mendiola, “Mercury complexes with the ligand benzaldehyde-N(4),N(4)-dimethylthiosemicarbazone,” Inorganica Chimica Acta, vol. 363, no. 6, pp. 1275–1283, 2010. View at Publisher · View at Google Scholar · View at Scopus
  22. R. Pedrido, M. J. Romero, M. R. Bermejo et al., “Influence of the metal size in the structure of the complexes derived from a pentadentate [N3O2] hydrazone,” Dalton Transactions, no. 44, pp. 5304–5314, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. J. C. Sheehan and W. A. Bolhofer, “An improved procedure for the condensation of potassium phthalimide with organic halides,” Journal of the American Chemical Society, vol. 72, no. 6, pp. 2786–2788, 1950. View at Google Scholar · View at Scopus
  24. K. Jarowicki and P. Kocienski, “Protecting groups,” Journal of Chemical Society. Perkin Transactions, vol. 18, pp. 2109–2135, 2001. View at Google Scholar
  25. J. F. Hartwig, “Evolution of a fourth generation catalyst for the amination and thioetherification of aryl halides,” Accounts of Chemical Research, vol. 41, no. 11, pp. 1534–1544, 2008. View at Publisher · View at Google Scholar · View at Scopus
  26. A. Berkessel, M. Bolte, T. Neumann, and L. Seidel, “Synthesis and X-ray crystal structure of the first mononuclear nickel(II) alkane thiolate complex with a mixed (S,N,N,O) ligand field,” Chemische Berichte, vol. 129, no. 10, pp. 1183–1189, 1996. View at Publisher · View at Google Scholar · View at Scopus
  27. M. S. Gibson and R. W. Bradshaw, “Gabriel synthesis of primary amines,” Angewandte Chemie—International Edition, vol. 7, pp. 919–930, 1968. View at Google Scholar
  28. C. Oldham and D. G. Tuck, “The direct electrochemical synthesis of [(C6H5)3Ph]2[CoCl4]: an example of the use of anodic oxidation in the preparation of metal ion complexes,” Journal of Chemical Education, vol. 59, no. 4, pp. 420–421, 1982. View at Publisher · View at Google Scholar · View at Scopus
  29. R. Golbedaghi, S. Salehzadeh, H. R. Khavasi, and A. G. Blackman, “Mn(II) complexes of three [2+2] macrocyclic Schiff base ligands. Synthesis and X-ray crystal structure of the first binuclear-di(binuclear) cocrystal,” Polyhedron, vol. 68, pp. 151–156, 2014. View at Google Scholar
  30. 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
  31. E. S. Ryabova, P. Rydberg, M. Kolberg et al., “A comparative reactivity study of microperoxidases based on hemin, mesohemin and deuterohemin,” Journal of Inorganic Biochemistry, vol. 99, no. 3, pp. 852–863, 2005. View at Publisher · View at Google Scholar · View at Scopus
  32. C. L. Hunter, R. Maurus, M. R. Mauk et al., “Introduction and characterization of a functionally linked metal ion binding site at the exposed heme edge of myoglobin,” Proceedings of the National Academy of Sciences of the United States of America, vol. 100, no. 7, pp. 3647–3652, 2003. View at Publisher · View at Google Scholar · View at Scopus
  33. M. Zampakou, V. Tangoulis, C. P. Raptopoulou, V. Psycharis, A. N. Papadopoulos, and G. Psomas, “Structurally diverse manganese(II)-diclofenac complexes showing enhanced antioxidant activity and affinity to serum albumins in comparison to sodium diclofenaco,” European Journal of Inorganic Chemistry, vol. 2015, no. 13, pp. 2285–2294, 2015. View at Publisher · View at Google Scholar
  34. M. F. Zipplies, W. A. Lee, and T. C. Bruice, “Influence of hydrogen ion activity and general acid-base catalysis on the rate of decomposition of hydrogen peroxide by a novel nonaggregating water-soluble iron(III) tetraphenylporphyrin derivative,” Journal of the American Chemical Society, vol. 108, no. 15, pp. 4433–4445, 1986. View at Publisher · View at Google Scholar · View at Scopus
  35. M. Maneiro, M. R. Bermejo, A. Sousa et al., “Synthesis and structural characterisation of new manganese(II) and (III) complexes. Study of their photolytic and catalase activity and X-ray crystal structure of [Mn(3-OMe, 5-Br-salpn)(EtOH)(H2O)]ClO4,” Polyhedron, vol. 19, no. 1, pp. 47–54, 2000. View at Publisher · View at Google Scholar · View at Scopus
  36. K. Mitra, S. Biswas, C. R. Lucas, and B. Adhikary, “Manganese(III) complexes of N2O2 donor 5-bromosalicylideneimine ligands: combined effects of electron withdrawing substituents and chelate ring size variations on electrochemical properties,” Inorganica Chimica Acta, vol. 359, no. 7, pp. 1997–2003, 2006. View at Publisher · View at Google Scholar · View at Scopus
  37. S. Naskar, S. Naskar, R. J. Butcher, M. Corbella, A. Espinosa Ferao, and S. K. Chattopadhyay, “Synthesis, X-ray crystal structures, and spectroscopic, electrochemical, and theoretical studies of MnIIIcomplexes of pyridoxal schiff bases with two diamines,” European Journal of Inorganic Chemistry, no. 18, pp. 3249–3260, 2013. View at Publisher · View at Google Scholar · View at Scopus
  38. C. Palopoli, C. Duhayon, J.-P. Tuchagues, and S. Signorella, “Synthesis, characterization, and reactivity studies of a water-soluble bis(alkoxo)(carboxylato)-bridged diMnIII complex modeling the active site in catalase,” Dalton Transactions, vol. 43, no. 45, pp. 17145–17155, 2014. View at Publisher · View at Google Scholar · View at Scopus