Skip to main content
Log in

Potentiometric Investigation on Complex Formation and Stabilities of Some Divalent Metal Ions with l-Cysteine and Glycine as Ligands in Aqueous Solutions

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

Complexes of the divalent metal ions, Ca2+ and Zn2+ with the bio-relevant α-amino acids, l-cysteine and glycine were investigated by means of the potentiometric technique. The dissociation constants of the bio-ligands were determined and used for determining the stability constants of their binary and ternary complexes formed in aqueous solutions at 25 ± 0.1 °C and constant ionic strength of 0.20 mol·dm−3 NaNO3. The acid–base properties of glycine were investigated at different ionic strengths, ranging from 0.01 to 0.30 mol·dm−3 NaNO3 at 25.0 ± 0.1 °C. The concentration distribution of the different glycine species formed in solution due to variation of pH was evaluated and discussed. The formation of the different 1:1 and 1:2 binary complexes and 1:1:1 ternary complexes were inferred from the potentiometric pH-metric titration curves. The ternary complex formation occurred in a stepwise manner with l-cysteine acting as the primary ligand. The stability constants of these binary and ternary complex systems were evaluated. The ∆log10 K values, percentage of relative stabilization (%R.S.) and log10 X for the ternary complexes were evaluated and are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Sheng, L., Whorton, A.R.: Identification of stereoselective transporters for S-nitroso-L-cysteine. J. Biol. Chem. 14, 3027–3032 (2004)

    Google Scholar 

  2. Chen, Y.Y., Chu, H.M., Pan, K.T., Teng, C.H., Wang, D.L., Wang, A.H.J., Khoo, K.H., Meng, T.C.: Cysteine S-nitrosylation protects protein-tyrosine phosphatase 1B against oxidation-induced permanent inactivation. J. Biol. Chem. 283, 35265–352671 (2008)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. Sigel, H.: Metal Ions in Biological Systems, vol. 3. Marcel Dekker, New York (1974)

    Google Scholar 

  4. 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)

    Article  CAS  Google Scholar 

  5. van Beusichem, M., Farrell, N.: Crystal and molecular structure of trans-dichlorobis(thiazole) platinum(II). J. Inorg. Chem. 31, 634–639 (1992)

    Article  Google Scholar 

  6. Naydenova, E.D., Todorov, P.T., Topashka-Ancheva, M.N., Momekov, G.T., Yordanova, T.Z., Konstantinov, S.M., Troev, K.D.: Novel N-(phosphonomethyl) glycine derivatives: design, characterization and biological activity. Eur. J. Med. Chem. 43, 1199–1205 (2008)

    Article  CAS  PubMed  Google Scholar 

  7. 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)

    Google Scholar 

  8. Bertini, I., Gray, H.B., Lippard, S.J., Valentine, J.S.: Bioinorganic Chemistry. University Science Books, Mill Valley (1994)

    Google Scholar 

  9. Goodman Gilman, A., Goodman, L.S.: Goodman and Gilman’s he pharmacological basis of therapeutics, 10th edn. Mc-Graw Hill, New York (2002)

    Google Scholar 

  10. Kimura, E., Kurogi, Y., Shionoya, M., Shiro, M.: Synthesis, properties, and complexation of a new imidazole-pendant macrocyclic 12-membered triamine ligand. Inorg. Chem. 30, 4524–4529 (1991)

    Article  CAS  Google Scholar 

  11. Schayer, R.W.: The metabolism of ring labeled histamine. J. Biol. Chem. 196, 469–475 (1952)

    Article  CAS  PubMed  Google Scholar 

  12. Baldridge, R.C., Tourtellotte, C.D.: The metabolism of histidine. III. Urinary metabolites. J. Biol. Chem. 233, 125–127 (1958)

    Article  CAS  PubMed  Google Scholar 

  13. Khandelwal, J.K., Prell, G.D., Morrishow, A.M., Green, J.P.: Presence and measurement of imidazoleacetic acid, a c-aminobutyric acid agonist, in rat brain and human cerebrospinal fluid. J. Neurochem. 52, 1107–1113 (1989)

    Article  CAS  PubMed  Google Scholar 

  14. Garcıa-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)

    Article  CAS  Google Scholar 

  15. Ranford, J.D., Sadler, P.J.: Cytotoxicity and antiviral activity of transition-metal salicylatocomplexes and crystal structure of bis(diisopropylsalicylato)(1,10-phenanthroline)copper(II). J. Chem. Soc. Dalton Trans. 22, 3393–3399 (1993)

    Article  Google Scholar 

  16. Geraghty, M., Sheridan, V., McCann, M., Devereux, M., McKee, V.: Synthesis and anti-candida activity of copper(II) and manganese(II) carboxylate complexes: x-ray crystal structures of [Cu(sal)(bipy)]·C2H5OH·H2O and [Cu(norb)(phen)2]·6.5H2O (salH2 = salicylic acid; norbH2 = cis-5-norbornene-endo-2,3-dicarboxylic acid; bipy = 2,20-bipyridine; phen = 1,10-phenanthroline). Polyhedron 18, 2931–2939 (1999)

    Article  CAS  Google Scholar 

  17. Khalil, M.M., El-Deeb, M.M., Mahmoud, R.K.: Equilibrium studies of binary systems involving lanthanide and actinide metal ions and some selected aliphatic and aromatic monohydroxamic acids. J. Chem. Eng. Data 52, 1571–1579 (2007)

    Article  CAS  Google Scholar 

  18. Khalil, M.M., Mahmoud, R.K.: New insights into M(II)-hydroxamate interactions: the electro-analytical behavior of metal(II) complexes involving monohydroxamic acids and diamines in an aqueous medium. J. Chem. Eng. Data 53, 2318–2327 (2008)

    Article  CAS  Google Scholar 

  19. Khalil, M.M., Attia, A.E.: potentiometric studies on the binary and ternary complexes of copper(II) containing dipicolinic acid and amino acids. J. Chem. Eng. Data 44, 180–184 (1999)

    Article  CAS  Google Scholar 

  20. Khalil, M.M.: complexation equilibria and determination of stability constants of binary and ternary complexes with ribonucleotides (AMP, ADP, and ATRP) and salicylhydroxamic acid as ligands. J. Chem. Eng. Data 45, 70–74 (2000)

    Article  CAS  Google Scholar 

  21. Khalil, M.M.: solution equilibria and stabilities of binary and ternary complexes with N-(2-acetamido) iminodiacetic acid and ribonucleotides (AMP, ADP, and ATP). J. Chem. Eng. Data 45, 837–840 (2000)

    Article  CAS  Google Scholar 

  22. Khalil, M.M., Attia, A.E.: potentiometric studies on the formation equilibria of binary and ternary complexes of some metal ions with dipicolinic acid and amino acids. J. Chem. Eng. Data 45, 1108–1110 (2000)

    Article  CAS  Google Scholar 

  23. Khalil, M.M., Taha, M.: Equilibrium studies of binary and ternary complexes involving tricine and some selected amino acids. Monatsh. Chem. 135, 385–395 (2004)

    Article  CAS  Google Scholar 

  24. Khalil, M.M., Fazary, A.E.: Potentiometric studies on binary and ternary complexes of di- and trivalent metal ions involving some hydroxamic acids, amino acids and nucleic acid components. Monatsh. Chem. 135, 1455–1474 (2004)

    Article  CAS  Google Scholar 

  25. Khalil, M.M., Mohamed, S.A., Radalla, A.M.: Potentiometric and conductometric studies on the binary and mixed-ligand complexes in solution: mII–dipicolinic acid-glycine systems. Talanta 44, 1365–1369 (1997)

    Article  CAS  PubMed  Google Scholar 

  26. Khalil, M.M., Radalla, A.M.: Binary and ternary complexes of inosine. Talanta 46, 53–61 (1998)

    Article  CAS  PubMed  Google Scholar 

  27. Khalil, M.M., Radalla, A.M., Mohamed, A.G.: Potentiometric Investigation on Complexation of Divalent Transition Metal Ions with some zwitterionic buffers and triazoles. J. Chem. Eng. Data 54, 3261–3272 (2009)

    Article  CAS  Google Scholar 

  28. Khalil, M.M., Radalla, A.M, Mohamed, N.A.: Solution equilibria and thermodynamic studies on complexation of divalent transition metal ions with some triazoles and biologically important aliphatic dicarboxylic acids in aqueous media. The First Scientific Conference for Postgraduate Students. Beni-Suef University, Beni-Suef, Egypt. p 200 (2009)

  29. Khalil, M. M., Radalla, A. M., Qassim, F.: Equilibrium and thermodynamic studies on binary and ternary complex systems including some triazoles and aromatic carboxylic acids. The First Scientific Conference for Postgraduate Students. Beni-Suef University, Beni-Suef, Egypt. p. 400 (2009)

  30. Radalla, A.M.: Potentiometric and conductometric studies on binary and ternary complexes of divalent transition metal ions with gallic acid and some aliphatic dicarboxylic acids as ligands. Pittsburgh Conference for Analytical Chemistry and Applied Spectroscopy (PITTCON), Orlando. 1401-7 CO-2026 (2012)

  31. Radalla, A.M., Khalil, M.M., Mohamed, N.A.: Solution equilibrium and thermodynamic studies of complexation of divalent transition metal ions with some triazoles and biologically important aliphatic dicarboxylic acids in aqueous media. J. Solution Chem. 42, 1123–1145 (2013)

    Article  CAS  Google Scholar 

  32. Radalla, A.M., Khalil, M.M., Mohamed, F.Q., Mahmoud, R.K.: Equilibrium studies of ternary systems involving some selected transition metal ions, triazoles and aromatic carboxylic acids. Korean J. Chem. Eng. 31, 109–119 (2014)

    Article  CAS  Google Scholar 

  33. Radalla, A.M.M.: Potentiometric studies on binary and ternary complexes of some divalent transition metal ions involving gallic acid and some aliphatic dicarboxylic acids in aqueous solutions. Beni-Suef Univ. J. Basic Appl. Sci. (BJABS) 4, 174–182 (2015)

    Article  Google Scholar 

  34. Gran, G.: Determination of the equivalence point in potentiometric titration. Analyst 77, 61–671 (1952)

    Article  Google Scholar 

  35. Welcher, F.J.: The Analytical Uses of Ethylenediaminetetraacetic Acid. Von Nostrand, Princeton, NJ (1965)

    Google Scholar 

  36. Longhi, P., D’Andrea, F., Mussini, T., Rondinini, S.: Verification of the approximate equitransference of the aqueous potassium chloride salt bridge at high concentrations. Anal. Chem. 62, 1019–1021 (1990)

    Article  CAS  Google Scholar 

  37. Irving, H., Rossotti, H.S.: Methods for computing successive stability constants from experimental formation curves. J. Chem. Soc. 40, 397–3405 (1953)

    Google Scholar 

  38. Irving, H.M., Rossotti, H.S.: The calculation of formation curves of metal complexes from pH titration curves in mixed solvent. J. Chem. Soc. 24, 2904–2913 (1954)

    Article  Google Scholar 

  39. Martell, A.E., Smith, R.M.: Critical Stability Constants, pp. 1–4. Plenum Press, New York (1976)

    Google Scholar 

  40. Inezedy, J.: Determination of equilibrium constants, In: Analytical Applications of Complex Equilibria. Ellis Horwood, Chechester, (1976)

  41. Cannan, R.K., Knight, J.G.: Dissociation constants of some thioacids. J. Am. Chem. Soc. 10, 1385–1389 (1927)

    Google Scholar 

  42. Melisa, A.G., Neilands, J.B.: Apparent dissociation constants of l-cysteine derivatives. J. Chem. Eng. Data 12, 3389–3397 (1954)

    Google Scholar 

  43. Kennedy, C.D.: Ionic Strength and the dissociation of acids. Biochem. Educ. 18, 35–40 (1990)

    Article  CAS  Google Scholar 

  44. James, P.D., Parameswaran, K.N.: Acidic dissociation constants of thiols. J. Chem. Eng. Data 6, 386–389 (1955)

    Google Scholar 

  45. Elliott, D.C., Dawson, R.M., James, K.M.: Data for Biochemical Research, pp. 1–31. Oxford Science Publications, Oxford (1986)

    Google Scholar 

  46. Martin, R.B., Prados, R.J.: Some factors influencing mixed complex formation. J. Inorg. Nucl. Chem. 36, 1665–1674 (1974)

    Article  CAS  Google Scholar 

  47. Sigel, H.: Metal Ions In Biological Sytems, Vol. 2. Marcel Dekker, New York (1973)

  48. Laurie, S.H., James, C.: Binary and ternary complexes of hydroxmic acids. Inorg. Chim. Acta 78, 225–229 (1974)

    Article  Google Scholar 

  49. Chaires, J.B.: Calorimetry and thermodynamics in drug design. Ann. Rev. Biophys. 37, 135–151 (2008)

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Abdelatty Mohamed Radalla.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file 1 (DOC 135 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Radalla, A.M. Potentiometric Investigation on Complex Formation and Stabilities of Some Divalent Metal Ions with l-Cysteine and Glycine as Ligands in Aqueous Solutions. J Solution Chem 50, 954–967 (2021). https://doi.org/10.1007/s10953-021-01100-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-021-01100-8

Keywords

Navigation