Potentiometric and thermodynamic studies of binary and ternary transition metal(II) complexes of imidazole-4-acetic acid and some bio-relevant ligands

Journal of Solution Chemistry

Volumn 42, Issue 5, 2013, Pages 1028-1050

  Aljahdali, M ^a   El Sherif, Ahmed A ^b,c   Shoukry, Mohamed M ^b,d   Mohamed, Seham E ^b  

^a KING ABDULAZIZ UNIVERSITY   (Saudi Arabia)

^b CAIRO UNIVERSITY   (Egypt)

^c NORTHERN BORDER UNIVERSITY   (Saudi Arabia)

^d ISLAMIC UNIVERSITY OF MADINAH   (Saudi Arabia)

Author keywords

Amides; Amino acids; DNA constituents; Imidazole 4 acetic acid (IMA); Potentiometry; Thermodynamics

Indexed keywords

EID: 84879126453     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-013-0015-9     Document Type: Article

References (51)

1. Frausto da Silva, J.J.R., Williams, R.J.P.: The Biological Chemistry of the Elements; The Inorganic Chemistry of Life. Clarendon Press, Oxford (1991)
2. Bertini, I., Gray, H.B., Lippard, S.J., Valentine, J.S.: Bioinorganic Chemistry. University Science Books, Mill Valley (1994)
3. Goodman Gilman, A., Goodman, L.S.: Goodman and Gilman's the Pharmacological Basis of Therapeutics, 10th edn. Mc-Graw Hill, New Jersey (2002)
4. Kimura, E., Kurogi, Y., Shionoya, M., Shira, M.: Synthesis, properties, and complexation of a new imidazole-pendant macrocyclic 12-membered triamine ligand. Inorg. Chem. 30, 4524-4529 (1991)
5. Schayer, R.W.: The metabolism of ring labeled histamine. J. Biol. Chem. 196, 469-475 (1952)
6. Baldridge, R.C., Tourtellotte, C.D.: The metabolism of histidine. III. Urinary metabolites. J. Biol. Chem. 233, 125-127 (1958)
7. Khandelwal, J.K., Prell, G.D., Morrishow, A.M., Green, J.P.: Presence and measurement of imidazoleacetic acid, a γ-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. J. Neurochem. 52, 1107-1113 (1989)
8. García-Raso, A., Fiol, J.J., Adrover, B., Tauler, P., Pons, A., Mata, I., Espinosa, E., Molins, E.: Reactivity of copper(II) peptide complexes with bioligands (benzimidazole and creatinine). Polyhedron 22, 3255-3264 (2003)
9. Ranford, J.D., Sadler, P.J.: Cytotoxicity and antiviral activity of transition-metal salicylato complexes and crystal structure of bis(diisopropylsalicylato)(1,10-phenanthroline)copper(II). Dalton Trans. 22, 3393-3399 (1993)
10. 2 = salicylic acid; norbH2 = cis-5-norbornene-endo-2,3-dicarboxylic acid; bipy = 2,2′-bipyridine; phen = 1,10-phenanthroline). Polyhedron 18, 2931-2939 (1999)
11. Saha, D.K., Sandbhor, U., Shirisha, K., Padhye, S., Deobagkar, D., Ansond, C.E., Powell, A.K.: A novel mixed-ligand antimycobacterial dimeric copper complex of ciprofloxacin and phenanthroline. Bioorg. Med. Chem. Lett. 14, 3027-3032 (2004)
12. Zoroddu, M.A., Zanetti, S., Pogni, R., Basosi, R.: An electron spin resonance study and antimicrobial activity of copper(II)-phenanthroline complexes. J. Inorg. Biochem. 63, 291-300 (1996)
13. Sigel, H.: Metal Ions in Biological Systems, vol. 3. Marcel Dekker, New York (1974)
14. Lau, S., Sarkar, B.: Kinetic studies of copper(II)-exchange from l-histidine to human serum albumin and diglycyl-l-histidine, a peptide mimicking the copper(II)-transport site of albumin. Can. J. Chem. 53, 710-715 (1975)
15. Bensichem, M.V., Farrell, N.: Activation of the trans geometry in platinum antitumor complexes. Synthesis, characterization, and biological activity of complexes with the planar ligands pyridine, N-methylimidazole, thiazole, and quinoline. Crystal and molecular structure of trans- dichlorobis(thiazole)platinum(II). Inorg. Chem. 31, 634-639 (1992)
16. El-Sherif, A.A., Shoukry, M.M., Abd El-Gawad, M.M.A.: Protonation equilibria of some selected α-amino acids in DMSO-water mixture and their Cu(II)-complexes. J. Solution Chem. 42, 412-427 (2013)
17. Shoukry, M.M., Khairy, E.M., El-Sherif, A.A.: Ternary complexes involving copper(II) and amino acids, peptides and DNA constituents. The kinetics of hydrolysis of α-amino acid esters. Trans. Met. Chem. 27, 656-664 (2002)
18. El-Sherif, A.A., Aljahdali, M.: Equilibrium studies of binary and mixed-ligand complexes of zinc(II) involving 2-(aminomethyl)-benzimidazole and some bio-relevant ligands. J. Solution Chem. 41, 1759-1776 (2012)
19. El-Sherif, A.A., Shoukry, M.M., van Eldik, R.: Complex formation reactions and stability constants for mixed-ligand complexes of diaqua(2-picolylamine)palladium(II) with some bio-relevant ligands. J. Chem. Soc. Dalton Trans. 7, 1425-1432 (2003)
20. El-Sherif, A.A.: Mixed-ligand complexes of 2-(aminomethyl)benzimidazole palladium(II) with various biologically relevant ligands. J. Solution Chem. 35, 1287-1301 (2006)
21. Mahmoud, M.M.A., El-Sherif, A.A.: Complex formation equilibria between Zn(II), nitrile-tris(methyl phosphonic acid) and some bio-relevant ligands. The kinetics and mechanism for zinc(II) ion promoted hydrolysis of glycine methyl ester. J. Solution Chem. 39, 639-653 (2010)
22. El-Sherif, A.A.: Mixed ligand complex formation reactions and equilibrium studies of Cu(II) with bidentate heterocyclic alcohol (N, O) and some bio-relevant ligands. J. Solution Chem. 41, 813-824 (2010)
23. El-Sherif, A.A.: Coordination properties of bidentate (N, O) and tridentate (N, O, O) heterocyclic alcohols with dimethyltin(IV) ion. J. Coord. Chem. 64, 1240-1253 (2011)
24. El-Sherif, A.A., Shoukry, M.M., Hosny, W.M., Abd Al-Moghny, M.G.: Complex formation equilibria of unusual seven-coordinate Fe(EDTA) complexes with DNA constituents and related bio-relevant ligands. J. Solution Chem. 41, 813-827 (2012)
25. Welcher, F.J.: The Analytical Uses of Ethylenediamine Tetraacetic Acid. Van Nostand, Princeton (1965)
26. Gans, P., Sabatini, A., Vacca, A.: An improved computer program for the computation of formation constants from potentiometric data. Inorg. Chim. Acta 18, 237-239 (1976)
27. Pettit, L.D.: IUPAC Stability Constants Database. Academic Software (1993)
28. Perrin, D.D.: Stability Constants of Metal-Ion Complexes. Part B. Organic Ligands. Pergamon Press, Oxford (1979)
29. Török, I., Surdy, P., Rockenbauer, A., Korecz Jr, L., Anthony, G., Koolhaas, A., Gajda, T.: Nickel(II)-, copper(II)- and zinc(II)-complexes of some substituted imidazole ligands. J. Inorg. Biochem. 71, 7-14 (1998)
30. Zimmermann, S.C., Korthals, J.S., Cramer, K.D.: Syn and anti-oriented imidazole carboxylates as models for the histidine-aspartate couple in serine proteases and other enzymes. Tetrahedron 47, 2649-2660 (1991)
31. Figgs, B.N.: Introduction to Ligand Fields. Interscience Publishers, New York (1996)
32. Huheey, J.E.: Inorganic Chemistry - Principles of Structure and Reactivity. Harper SI Edn, New York (1983)
33. Irving, H., Williams, R.J.P.: Some factors controlling the selectivity of organic reagents. Analyst (Lond) 77, 813-829 (1952)
34. Cotton, F.A., Wilkinson, G.: Advanced Inorganic Chemistry. Wiley, London (1962)
35. Phillips, C.S.G., Williams, R.J.P.: Inorganic Chemistry, vol. 2, p. 268. Oxford University Press, Oxford (1966)
36. Harlly, F.R., Burgess, R.M., Alcock, R.M.: Solution Equilibria, p. 257. Ellis Harwood, Chichester (1980)
37. Sigel, H., Martin, R.B.: Coordinating properties of the amide bond. Stability and structure of metal ion complexes of peptides and related ligands. Chem. Rev. 82, 385-426 (1982)
38. Sovago, I.: In: Burger, K. (ed.) Biocoordination Chemistry. Ellis Horwood, Chichester (1990)
39. Pettit, L.D., Gregor, J.E., Kozlowski, H.: Perspectives in Bioinorganic Chemistry, vol. 1, pp. 1-41. Jai Press Ltd, Greenwich (1991)
40. El-Sherif, A.A., Shoukry, M.M.: 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. Inorg. Chim. Acta 360, 473-487 (2007)
41. Maskos, K.: 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 Biochim. Polonica 28(2), 183-200 (1981)
42. Martin, R.B., Mariam, Y.H.: Metal Ions in Biological Systems, vol. 8, pp. 57-125. Marcel Dekker, New York (1979)
43. Sigel, H.: Metal Ions in Biological Systems, vol. 2. Marcel Dekker, New York (1973)
44. Sigel, H.: Stability, structure and reactivity of mixed ligand complexes in solution. In: Banerjea, D. (ed.) Coordination Chemistry, vol. 20, pp. 27-45. IUPAC/Pergamon Press, Oxford (1980)
45. 2+ complex: stability, structure and reactivity. Angew. Chem. Int. Ed. Engl. 14, 394-402 (1975)
46. DeWitt, R., Watters, J.I.: Spectrophotometric investigation of a mixed complex of copper(II) ion with oxalate ion and ethylenediamine. J. Am. Chem. Soc. 76, 3810-3814 (1954)
47. Martin, R.B., Prados, R.: Some factors influencing mixed complex formation. J. Inorg. Nucl. Chem. 36, 1665-1670 (1974)
48. Munakata, M., Harada, M., Niina, S.: Stability enhancement of mixed-ligand copper(II), nickel(II), and cobalt(II) complexes with 2,2′-bipyridyl and β-diketonates. Inorg. Chem. 15, 1727-1729 (1976)
49. 2+ with 2,2′-dipyridyl and cyclohexane-1,1-dicarboxylic acid. Inorg. Chim. Acta 18, 155-158 (1976)
50. Walker, F.A., Sigel, H., McCormick, D.B.: Spectral properties of mixed-ligand copper(II) complexes and their corresponding binary parent complexes. Inorg. Chem. 11, 2756-2763 (1972)
51. Sigel, H., Huber, P.R., Griesser, R.: Ternary complexes in solution. IX. Stability-increasing effect of the pyridyl and imidazole groups on the formation of mixed-ligand copper(II)-pyrocatecholate complexes. Inorg. Chem. 10, 945-947 (1971)