Table of Contents Author Guidelines Submit a Manuscript
Bioinorganic Chemistry and Applications
Volume 2012, Article ID 984291, 10 pages
http://dx.doi.org/10.1155/2012/984291
Research Article

Thermodynamic Investigation and Mixed Ligand Complex Formation of 1,4-Bis-(3-aminopropyl)-piperazine and Biorelevant Ligands

Department of Chemistry, Faculty of Science, Cairo University, Giza 12613, Egypt

Received 3 July 2012; Revised 7 October 2012; Accepted 8 October 2012

Academic Editor: Anastasios Keramidas

Copyright © 2012 Ahmed A. El-Sherif 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. E. Jóna, M. Kubranová, P. Šimon, and J. Mroziński, “Thermochemical investigation: Ni(II)-3-pyridylcarbinol (ronicol) interactions in solid halogeno and thiocyanato complexes,” Journal of Thermal Analysis, vol. 46, no. 5, pp. 1325–1337, 1996. View at Google Scholar · View at Scopus
  2. A. S. Mildvan and M. Cohn, “Kinetic and magnetic resonance studies of the pyruvate kinase reaction. II. Complexes of enzyme, metal, and substrates,” Journal of Biological Chemistry, vol. 241, no. 5, pp. 1178–1193, 1966. View at Google Scholar · View at Scopus
  3. G. M. R. Tombo and D. Bellus, “Chiralität und pflanzenschutz,” Angewandte Chemie, vol. 103, no. 10, pp. 1219–1241, 1991. View at Publisher · View at Google Scholar
  4. E. Bouwman, W. L. Driessen, and J. Reedijk, “Model systems for type I copper proteins: structures of copper coordination compounds with thioether and azole-containing ligands,” Coordination Chemistry Reviews, vol. 104, no. 1, pp. 143–172, 1990. View at Google Scholar · View at Scopus
  5. J. A. Turpin, R. W. Buckheit, D. Derse et al., “Inhibition of acute-, latent-, and chronic-phase human immunodeficiency virus type 1 (HIV-1) replication by a bistriazoloacridone analog that selectively inhibits HIV-1 transcription,” Antimicrobial Agents and Chemotherapy, vol. 42, no. 3, pp. 487–494, 1998. View at Google Scholar · View at Scopus
  6. M. Medou, G. Priem, L. Rocheblave et al., “Synthesis and anti-HIV activity of α-thiophenoxy-hydroxyethylamide derivatives,” European Journal of Medicinal Chemistry, vol. 34, no. 7-8, pp. 625–638, 1999. View at Google Scholar · View at Scopus
  7. B. Onoa and V. Moreno, “Nickel(II) and copper(II)—L-cysteine, L-methionine, L-tryptophan-nucleotide ternary complexes,” Transition Metal Chemistry, vol. 23, no. 4, pp. 485–490, 1998. View at Google Scholar · View at Scopus
  8. K. Burger, Biocoordination Chemistry: Coordination Equilibria in Biologically Active Systems, E. Horwood, New York, NY, USA, 1990.
  9. R. P. Bonomo, B. Di Blasio, G. Maccarrone et al., “Crystal and molecular structure of the [6-deoxy-6-[(2-(4-imidazolyl)ethyl)amino]cyclomaltoheptaose]copper(II) ternary complex with L-tryptophanate. Role of weak forces in the chiral recognition process assisted by a metallocyclodextrin,” Inorganic Chemistry, vol. 35, no. 15, pp. 4497–4504, 1996. View at Google Scholar · View at Scopus
  10. M. Sabat, B. Lippert, A. Sigel, and H. Sigel, Metal Ions in Biological Systems, vol. 33, Marcel Dekker, New York, NY, USA, 1996.
  11. E. Kimura, T. Koike, and M. Shionoya, “Lewis acids and vanadium,” in Metal Sites in Proteins and Models. Phosphatases, H. A. O. Hill, P. J. Sadler, and A. J. Thomson, Eds., vol. 89, no. 1, Springer, Berlin, Germany, 1997. View at Google Scholar
  12. T. Koike, M. Inoue, E. Kimura, and M. Shiro, “Novel properties of cooperative dinuclear zinc(II) ions: The selective recognition of phosphomonoesters and their P-O ester bond cleavage by a new dinuclear zinc(II) cryptate,” Journal of the American Chemical Society, vol. 118, no. 13, pp. 3091–3099, 1996. View at Publisher · View at Google Scholar · View at Scopus
  13. T. Koike, S. Kajitani, I. Nakamura, E. Kimura, and M. Shiro, “The catalytic carboxyester hydrolysis by a new zinc(II) complex with an alcohol-pendant cyclen (1-(2-hydroxyethyl)-1,4,7,10-tetraazacyclododecane): a novel model for indirect activation of the serine nucleophile by zinc(II) in zinc enzymes,” Journal of the American Chemical Society, vol. 117, no. 4, pp. 1210–1219, 1995. View at Google Scholar · View at Scopus
  14. E. Kimura, T. Koike, T. Shiota, and Y. Iitaka, “Acid properties of zinc(II) and cadmium(II) in complexation with macrocyclic oxo polyamine ligands,” Inorganic Chemistry, vol. 29, no. 23, pp. 4621–4629, 1990. View at Google Scholar · View at Scopus
  15. X. Zhang and R. Van Eldik, “A functional model for carbonic anhydrase: thermodynamic and kinetic study of a tetraazacyclododecane complex of zinc(II),” Inorganic Chemistry, vol. 34, no. 22, pp. 5606–5614, 1995. View at Google Scholar · View at Scopus
  16. E. Kimura and K. K. Karlin, Progress in Inorganic Chemistry, vol. 41, Wiley, 1994.
  17. E. Kimura, I. Nakamura, T. Koike et al., “Carboxyester hydrolysis promoted by a new zinc(II) macrocyclic triamine complex with an alkoxide pendant: a model study for the serine alkoxide nucleophile in zinc enzymes,” Journal of the American Chemical Society, vol. 116, no. 11, pp. 4764–4771, 1994. View at Google Scholar · View at Scopus
  18. E. Kimura, M. Shionoya, A. Hoshino, T. Ikeda, and Y. Yamada, “A model for catalytically active zinc(II) ion in liver alcohol dehydrogenase: a novel “hydride transfer” reaction catalyzed by zinc(II)-macrocyclic polyamine complexes,” Journal of the American Chemical Society, vol. 114, no. 26, pp. 10134–10137, 1992. View at Google Scholar · View at Scopus
  19. A. A. El-Sherif and M. M. Shoukry, “Ternary copper(II) complexes involving 2-(aminomethyl)-benzimidazole and some bio-relevant ligands. Equilibrium studies and kinetics of hydrolysis for glycine methyl ester under complex formation,” Inorganica Chimica Acta, vol. 360, no. 2, pp. 473–487, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. A. A. El-Sherif and M. M. Shoukry, “Copper(II) complexes of imino-bis(methyl phosphonic acid) with some bio-relevant ligands. Equilibrium studies and hydrolysis of glycine methyl ester through complex formation,” Journal of Coordination Chemistry, vol. 58, no. 16, pp. 1401–1415, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. A. A. El-Sherif and M. M. Shoukry, “Coordination properties of tridentate (N,O,O) heterocyclic alcohol (PDC) with Cu(II). Mixed ligand complex formation reactions of Cu(II) with PDC and some bio-relevant ligands,” Spectrochimica Acta A, vol. 66, no. 3, pp. 691–700, 2007. View at Publisher · View at Google Scholar · View at Scopus
  22. A. A. El-Sherif, “Mixed-ligand complexes of 2-(aminomethyl)benzimidazole palladium(II) with various biologically relevant ligands,” Journal of Solution Chemistry, vol. 35, no. 9, pp. 1287–1301, 2006. View at Publisher · View at Google Scholar · View at Scopus
  23. A. A. El-Sherif, M. M. Shoukry, and R. Van Eldik, “Complex-formation reactions and stability constants for mixed-ligand complexes of diaqua(2-picolylamine)palladium(II) with some bio-relevant ligands,” Dalton Transactions, no. 7, pp. 1425–1432, 2003. View at Publisher · View at Google Scholar · View at Scopus
  24. M. M. Shoukry, E. M. Khairy, and A. A. El-Sherif, “Ternary complexes involving copper(II) and amino acids, peptides and DNA constituents. The kinetics of hydrolysis of α-amino acid esters,” Transition Metal Chemistry, vol. 27, no. 6, pp. 656–664, 2002. View at Publisher · View at Google Scholar · View at Scopus
  25. R. G. Bates, Determination of pH-Theory and Practice, Wiley-Interscience, New York, NY, USA, 2nd edition, 1975.
  26. A. A. El-Sherif, “Coordination properties of bidentate (N, O) and tridentate (N, O, O) heterocyclic alcohols with dimethyltin (IV) ion,” Journal of Coordination Chemistry, vol. 64, no. 7, pp. 1240–1253, 2011. View at Google Scholar
  27. P. Gans, A. Sabatini, and A. Vacca, “An improved computer program for the computation of formation constants from potentiometric data,” Inorganica Chimica Acta, vol. 18, pp. 237–239, 1976. View at Google Scholar · View at Scopus
  28. L. Pettit, University of Leeds, Personal Communication.
  29. H. M. N. H. Irving and R. J. P. Williams, “The stability of transition-metal complexes,” Journal of the Chemical Society, pp. 3192–3210, 1952. View at Publisher · View at Google Scholar · View at Scopus
  30. J. E. Huheey, Inorganic Chemistry-Principles of Structure and Reactivity, Harper, New York, NY, USA, 1983.
  31. F. A. Cotton and G. Wilkinson, Advaned Inorganic Chemistry, Wiley, London, UK, 1962.
  32. C. S. G. Phillips and R. J. P. Williams, Inorganic Chemistry: Metals, vol. 2, Oxford University Press, New York, NY, USA, 1966.
  33. M. M. A. Mohamed and A. A. El-Sherif, “Complex formation equilibria between zinc(II), nitrilo-tris(methyl phosphonic acid) and some bio-relevant ligands. The kinetics and mechanism for zinc(II) ion promoted hydrolysis of glycine methyl ester,” Journal of Solution Chemistry, vol. 39, no. 5, pp. 639–653, 2010. View at Publisher · View at Google Scholar · View at Scopus
  34. K. Maskos, “The interaction of metal ions with nucleic acids. A nuclear magnetic resonance relaxation time study of the copper(II)-inosine 5-monophosphate system in solution,” Acta Biochimica Polonica, vol. 28, no. 2, pp. 183–200, 1981. View at Google Scholar · View at Scopus
  35. D. J. Hodgson, “The stereochemistry of metal complexes of nucleic acid constituents,” in Progress in Inorganic Chemistry, S. J. Lippard, Ed., vol. 23, pp. 211–254, John Wiley, New York, NY, USA, 1977. View at Publisher · View at Google Scholar
  36. H. Sigel, Coordination Chemistry, vol. 20, Pergamon Press, Oxford, UK, 1980.
  37. H. Sigel, Metal Ions in Biological Systems, vol. 2, Dekker, New York, NY, USA, 1973.
  38. K. Maskos, “The interaction of metal ions with nucleic acids. A nuclear magnetic resonance relaxation time study of the copper(II)-inosine 5-monophosphate system in solution,” Acta Biochimica Polonica, vol. 28, no. 2, pp. 183–200, 1981. View at Google Scholar · View at Scopus
  39. O. Yamauchi and A. Odani, “Structure-stability relationship in ternary copper(II) complexes involving aromatic amines and tyrosine or related amino acids. Intramolecular aromatic ring stacking and its regulation through tyrosine phosphorylation,” Journal of the American Chemical Society, vol. 107, no. 21, pp. 5938–5945, 1985. View at Google Scholar · View at Scopus
  40. B. E. Fischer and H. Sigel, “Ternary complexes in solution. 35. Intramolecular hydrophobic ligand-ligand interactions in mixed ligand complexes containing an aliphatic amino acid,” Journal of the American Chemical Society, vol. 102, no. 9, pp. 2998–3008, 1980. View at Google Scholar · View at Scopus
  41. A. A. El-Sherif, “Equilibrium studies of binary and mixed-ligand complexes of zinc(II) involving 2-(aminomethyl)-benzimidazole and some bio-relevant,” Journal of Solution Chemistry. In press. View at Publisher · View at Google Scholar