Skip to main content
Log in

Kinetic and Thermodynamic Investigation of Human Serum Albumin Interaction with Anticancer Glycine Derivative of Platinum Complex by Using Spectroscopic Methods and Molecular Docking

  • Published:
Applied Biochemistry and Biotechnology Aims and scope Submit manuscript

Abstract

In this paper, a new anticancer Pt (II) complex, cis-[Pt (NH3)2(tertpentylgly)]NO3, was synthesized with glycine-derivative ligand and characterized. Cytotoxicity of this water-soluble Pt complex was studied against human cancer breast cell line of MCF-7. The interaction of human serum albumin (HSA) with Pt complex was studied by using UV-Vis, fluorescence spectroscopy methods, and molecular docking at 27 and 37 °C in the physiological situation (I = 10 mM, pH = 7.4). The negative \( \varDelta {H}_b^0 \) and positive \( \varDelta {S}_b^0 \) indicated that electrostatic force may be a major mode in the binding between Pt complex and HSA. Binding constant values were obtained through UV-Vis and fluorescence spectroscopy that reveal strong interaction. The negative Gibbs free energy that was obtained by using the UV-Vis method offers spontaneous interaction. Fluorescence quenching the intensity of HSA by adding Pt complex confirms the static mode of interaction is effective for this binding process. Hill coefficients, nH, Hill constant, kH, complex aggregation number around HSA, <J>, number of binding sites, g, HSA melting temperature, Tm, and Stern-Volmer constant, kSV, were also obtained. The kinetics of the interaction was studied, which showed a second-order kinetic. The results of molecular docking demonstrate the position of binding of Pt complex on HSA is the site I in the subdomain IIA.

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

Access this article

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

Instant access to the full article PDF.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14
Fig. 15
Fig. 16
Fig. 17
Fig. 18
Fig. 19

Similar content being viewed by others

Abbreviations

HSA:

Human serum albumin

PDB:

Protein Data Bank

Tertpentylgly:

1,1-Dimethyl propyl glycine

References

  1. Yang, F., Zhang, Y., & Liang, H. (2014). Interactive association of drugs binding to human serum albumin. International Journal of Molecular Sciences, 15, 3580–3595. https://doi.org/10.4172/2254-609X.100033.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  2. Yasseen, Z. J., & El-Ghossain, M. O. (2016). Studies on binding of widely used drugs with human serum albumin at different temperatures and PHs. Journal of Biomedical Science, 5, 19–27. https://doi.org/10.4172/2254-609X.100033.

    Article  Google Scholar 

  3. Tan, X., & Song, Z. (2014). Relationship investigation of molecular structure–binding affinity of antibiotics to bovine serum albumin using flow injection chemiluminescence analysis and molecular docking. RSC Advances, 4, 3263–3271. https://doi.org/10.1039/c3ra45885g.

    Article  CAS  Google Scholar 

  4. Shahabadi, N., & Nemati, L. (2014). Multispectroscopic studies on the interaction of a platinum (II) complex containing l-histidine and 1, 10-phenanthroline ligands with bovine serum albumin. Applied Biochemistry and Biotechnology, 172, 2800–2814. https://doi.org/10.1007/s12010-013-0715-z.

    Article  CAS  PubMed  Google Scholar 

  5. Divsalar, A., Zhila, I., Saboury, A. A., Nabiuni, M., Razmi, M., & Mansuri-Torshizi, H. (2013). Cytotoxic and spectroscopic studies on binding of a new synthesized bipyridine ethyl dithiocarbamate Pt (II) nitrate complex to the milk carrier protein of BLG. Journal of the Iranian Chemical Society, 10, 951–959. https://doi.org/10.1007/s13738-013-0232-6.

    Article  CAS  Google Scholar 

  6. Ndagi, U., Mhlongo, N., & Soliman, M. E. (2017). Metal complexes in cancer therapy–an update from drug design perspective. Drug Design, Development and Therapy, 11, 599–616. https://doi.org/10.2147/DDDT.S119488.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  7. Chuang, V. T. G., Maruyama, T., & Otagiri, M. (2009). Updates on contemporary protein binding techniques. Drug Metabolism and Pharmacokinetics, 24, 358–364. https://doi.org/10.2133/dmpk.24.358.

    Article  CAS  PubMed  Google Scholar 

  8. Summa, N., Schiessl, W., Puchta, R., van Eikema Hommes, N., & van Eldik, R. (2006). Thermodynamic and kinetic studies on reactions of Pt (II) complexes with biologically relevant nucleophiles. Inorganic Chemistry, 45, 2948–2959. https://doi.org/10.1021/ic051955r.

    Article  CAS  PubMed  Google Scholar 

  9. Yousefi, R., Aghevlian, S., Mokhtari, F., Samouei, H., Rashidi, M., Nabavizadeh, S. M., Tavaf, Z., Pouryasin, Z., Niazi, A., Faghihi, R., & Papari, M. M. (2012). The anticancer activity and HSA binding properties of the structurally related platinum (II) complexes. Applied Biochemistry and Biotechnology, 167, 861–872. https://doi.org/10.1007/s12010-012-9733-5.

    Article  CAS  PubMed  Google Scholar 

  10. Zheng, Y. R., Suntharalingam, K., Johnstone, T. C., Yoo, H., Lin, W., Brooks, J. G., & Lippard, S. J. (2014). Pt (IV) prodrugs designed to bind non-covalently to human serum albumin for drug delivery. Journal of the American Chemical Society, 136, 8790–8798. https://doi.org/10.1021/ja50382.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. Saeidifar, M., & Mansouri-Torshizi, H. (2015). Investigation of the interaction between human serum albumin and antitumor palladium (II) complex containing 1, 10-phenanthroline and dithiocarbamate ligands. Nucleosides, Nucleotides & Nucleic Acids, 34, 16–32. https://doi.org/10.1080/15257770.2014.955192.

    Article  CAS  Google Scholar 

  12. Lin, X. D., Liu, Y. H., Xie, C. Z., Bao, W. G., Shen, J., & Xu, J. Y. (2017). Three Pt (II) complexes based on thiosemicarbazone: synthesis, HSA interaction, cytotoxicity, apoptosis and cell cycle arrest. RSC Advances, 7, 26478–26486. https://doi.org/10.1039/c7ra04443.

    Article  CAS  Google Scholar 

  13. Shahabadi, N., & Hadidi, S. (2015). Mechanistic and conformational studies on the interaction of a platinum (II) complex containing an antiepileptic drug, levetiracetam, with bovine serum albumin by optical spectroscopic techniques in aqueous solution. Applied Biochemistry and Biotechnology, 175, 1843–1857. https://doi.org/10.1007/s12010-014-1423-z.

    Article  CAS  PubMed  Google Scholar 

  14. Coban, B., & Yildia, U. (2014). DNA-binding studies and antitumor evaluation of novel water soluble organic pip and hpip analogs. Applied Biochemistry and Biotechnology, 172, 248–262. https://doi.org/10.1007/s12010-013-0513-7.

  15. Dehkhodaei, M., Sahihi, M., Rudbari, H. A., Ariaeefar, M., Gharaghani, S., Azadbakht, R., Taheri, S., & Kajani, A. A. (2018). Multi experimental and computational studies for DNA and HSA interaction of new nano-scale ultrasound-assisted synthesized Pd (II) complex as a potent anticancer drug. Journal of Molecular Liquids, 264, 386–397. https://doi.org/10.1016/j.molliq.2018.05.077.

    Article  CAS  Google Scholar 

  16. Chandrasekhar, V. R., Mookkandi Palsamy, K., Lokesh, R., Jegathalaprathaban, R., & Gurusamy, R. (2019). Biomolecular docking, antimicrobial and cytotoxic studies on new bidentate schiff base ligand derived metal (II) complexes. Applied Organometallic Chemistry, 33, e4753. https://doi.org/10.1002/a0c.4753.

    Article  Google Scholar 

  17. Dhahagani, K., Kesavan, M. P., Vinoth, K. G. G., Ravi, L., Rajagopal, G., & Rajesh, J. (2018). Crystal structure, optical properties, DFT analysis of new morpholine based Schiff base ligands and their copper (II) complexes: DNA, protein docking analyses, antibacterial study and anticancer evaluation. Materials Science and Engineering: C, 90, 119–130. https://doi.org/10.1016/j.msec.2018.034.032.

    Article  CAS  Google Scholar 

  18. Gubendran, A., Kesavan, M. P., Ayyanaar, S., Raja, J. D., Athappan, P., & Rajesh, J. (2017). Synthesis and characterization of water-soluble copper (II), cobalt (II) and zinc (II) complexes derived from 8-hydroxyquinoline-5-sulphonic acid: DNA binding and cleavage studies. Applied Organometallic Chemistry, 31, e3708. https://doi.org/10.1002/aoc.3708.

    Article  CAS  Google Scholar 

  19. Gubendran, A., Kesavan, M. P., Ayyanaar, S., Mitu, L., Athappan, P., & Rajesh, J. (2017). Non-enolisable Knoevenagel condensate appended Schiff bases-metal (II) complexes: spectral characteristics, DNA-binding and nuclease activities. Spectrochimica Acta A, 181, 39–46. https://doi.org/10.1016/j.saa.2017.03.031.

    Article  CAS  Google Scholar 

  20. Kesavan, M. P., Kumar, G. G. V., Anitha, K., Ravi, L., Raja, J. D., Rajagopal, G., & Rajesh, J. (2017). Natural alkaloid luotonin A and its affixed acceptor molecules: serum albumin binding studies. Journal of Photochemistry and Photobiology B, 173, 499–507. https://doi.org/10.1016/j.jphotobiol.2017.06.030.

    Article  CAS  Google Scholar 

  21. Kantoury, M., Eslami Moghadam, M., Tarlani, A. A., & Divsalar, A. (2016). Structure effect of some new anticancer Pt (II) complexes of amino acid derivatives with small branched or linear hydrocarbon chains on their DNA interaction. Chemical Biology & Drug Design, 88, 76–87. https://doi.org/10.1111/cbdd.12735.

    Article  CAS  Google Scholar 

  22. Abyaneh, F. S. S., Moghadam, M. E., Divsalar, A., Ajloo, D., & Sadr, M. H. (2018). Improving of anticancer activity and solubility of cisplatin by methylglycine and methyl amine ligands against human breast adenocarcinoma cell line. Applied Biochemistry and Biotechnology, 186, 271–291. https://doi.org/10.1007/s12010-018-2715-5.

    Article  CAS  Google Scholar 

  23. Hadian Rasanani, S., Eslami Moghadam, M., Soleimani, E., Divsalar, A., & Tarlani, A. (2017). Improving activity of anticancer oxalipalladium analog by the modification of oxalate group with isopentylglycine. Journal of Coordination Chemistry, 70, 3769–3789. https://doi.org/10.1080/00958972.2017.1395417.

    Article  CAS  Google Scholar 

  24. Kandagal, P. B., Ashoka, S., Seetharamappa, J., Vani, V., & Shaikh, S. M. T. (2006). Study of the interaction between doxepin and human serum albumin by spectroscopic methods. Journal of Photochemistry and Photobiology A, 179, 161–166. https://doi.org/10.1016/j.jphotochem.2005.08.008.

    Article  CAS  Google Scholar 

  25. Dehkhodaei, M., Sahihi, M., Rudbari, H. A., & Momenbeik, F. (2018). DNA and HSA interaction of vanadium (IV), copper (II), and zinc (II) complexes derived from an asymmetric bidentate Schiff-base ligand: multi spectroscopic, viscosity measurements, molecular docking, and ONIOM studies. Journal of Biological Inorganic Chemistry, 23, 181–192. https://doi.org/10.1007/s00775-017-1505-9.

    Article  CAS  PubMed  Google Scholar 

  26. Khosravi, I., Sahihi, M., Rudbari, H. A., Borhan, G., & Chavoshpour-Natanzi, Z. (2017). The interaction of a new Schiff base ligand with human serum albumin: molecular docking and molecular dynamics simulation studies. Journal of Macromolecular Science Part B, 56, 636–643. https://doi.org/10.1080/00222348.2017.1356634.

    Article  CAS  Google Scholar 

  27. Eslami Moghadam, M., Divsalar, A., Abolhosseini Shahrnoy, A., & Saboury, A. A. (2016). Synthesis, cytotoxicity assessment, and interaction and docking of novel palladium (II) complexes of imidazole derivatives with human serum albumin. Journal of Biomolecular Structure & Dynamics, 34, 1751–1762. https://doi.org/10.1080/07391102.2015.1090345.

    Article  CAS  Google Scholar 

  28. Bi, S., Song, D., Tian, Y., Zhou, X., Liu, Z., & Zhang, H. (2005). Molecular spectroscopic study on the interaction of tetracyclines with serum albumins. Spectrochimica Acta A, 61, 629–636. https://doi.org/10.1016/j.saa.2004.05.028.

    Article  CAS  Google Scholar 

  29. Xu, L., Hu, Y. X., Li, Y. C., Liu, Y. F., Zhang, L., Ai, H. X., & Liu, H. S. (2017). Study on the interaction of paeoniflorin with human serum albumin (HSA) by spectroscopic and molecular docking techniques. Chemistry Central Journal, 11, 116–128. https://doi.org/10.1186/s13065-017-0348-3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  30. Heydari, M., Moghadam, M. E., Tarlani, A., & Farhangian, H. (2017). DNA as a target for anticancer phen-imidazole Pd (II) complexes. Applied Biochemistry and Biotechnology, 182, 110–127. https://doi.org/10.1007/s12010-016-2314-2.

    Article  CAS  PubMed  Google Scholar 

  31. Stephanos, J. J. (1996). Drug-protein interactions: two-site binding of heterocyclic ligands to a monomeric hemoglobin. Journal of Inorganic Biochemistry, 62, 155–169. https://doi.org/10.1016/0162-0134(95)00144-1.

    Article  CAS  PubMed  Google Scholar 

  32. Aghaee, E., Ghasemi, J. B., Manouchehri, F., & Balalaie, S. (2014). Combined docking, molecular dynamics simulations and spectroscopic studies for the rational design of a dipeptide ligand for affinity chromatography separation of human serum albumin. Journal of Molecular Modeling, 20, 2446–2459. https://doi.org/10.1007/s00894-014-2446-7.

    Article  CAS  PubMed  Google Scholar 

  33. Fu, X. B., Liu, D. D., Lin, Y., Hu, W., Mao, Z. W., & Le, X. Y. (2014). Water-soluble DNA minor groove binders as potential chemotherapeutic agents: synthesis, characterization, DNA binding and cleavage, antioxidation, cytotoxicity and HSA interactions. Dalton Transactions, 43, 8721–8737. https://doi.org/10.1039/c3dt53577k.

    Article  CAS  PubMed  Google Scholar 

  34. Bordbar, A. K., Saadati, Z., & Sohrabi, N. (2004). Analysis of ligand binding process using binding capacity concept. Acta Biochimica Polonica, 51, 963–970.

    CAS  PubMed  Google Scholar 

  35. Ascenzi, P., Bocedi, A., Notari, S., Fanali, G., Fesce, R., & Fasano, M. (2006). Allosteric modulation of drug binding to human serum albumin. Medicinal Chemistry, 6, 483–489. https://doi.org/10.2174/138955706776361448.

    Article  CAS  Google Scholar 

  36. Ajloo, D., Moghadam, M. E., Ghadimi, K., Ghadamgahi, M., Saboury, A. A., Divsalar, A., Sheikhmohammadi, M., & Yousefi, K. (2015). Synthesis, characterization, spectroscopy, cytotoxic activity and molecular dynamic study on the interaction of three palladium complexes of phenanthroline and glycine derivatives with calf thymus DNA. Inorganica Chimica Acta, 430, 144–160. https://doi.org/10.1016/j.ica.2015.03.006.

    Article  CAS  Google Scholar 

  37. Rippe, K. (1997). Analysis of protein-DNA binding at equilibrium. B. I. F Futura, 12, 20–26.

    Google Scholar 

  38. Bordbar, A. K., Sohrabi, N., & Hojjati, E. (2004). The estimation of the hydrophobic and electrostatic contributions to the free energy change upon cationic surfactants binding to Jack bean urease. Colloids and Surfaces. B, Biointerfaces, 39, 171–175. https://doi.org/10.1016/j.colsurfb.2004.07.009.

    Article  CAS  PubMed  Google Scholar 

  39. Liu, P., Liu, J., Zhang, Y. Q., Wu, B. Y., & Wang, K. Z. (2015). Synthesis, DNA binding and photocleavage, and cellular uptake of an alkyl chain-linked dinuclear ruthenium (II) complex. Journal of Photochemistry and Photobiology. B, 143, 89–99. https://doi.org/10.1016/j.jphotobiol.2015.01.004.

    Article  CAS  Google Scholar 

  40. Sohrabi, N., Rasouli, N., & Raissi, M. (2017). Study the interaction of Ni complex of tetradentate schiff base ligand with hen egg white lysozyme. Physical and Chemical Research, 5, 113–123. https://doi.org/10.22036/pcr.2017.38593.

    Article  CAS  Google Scholar 

  41. Hadian Rasanani, S., Eslami Moghadam, M., Soleimani, E., Divsalar, A., Ajloo, D., Tarlani, A., & Amiri, M. (2018). Anticancer activity of new imidazole derivative of 1R, 2R-diaminocyclohexane palladium and platinum complexes as DNA fluorescent probes. Journal of Biomolecular Structure & Dynamics, 36, 3058–3076. https://doi.org/10.1080/07391102.2017.1385538.

    Article  CAS  Google Scholar 

  42. Varlan, A., Ionescu, S., & Hillebrand, M. (2011). Study of the interaction between ofloxacin and human serum albumin by spectroscopic methods. Luminescence, 26, 710–715. https://doi.org/10.1002/bio.1302.

    Article  CAS  PubMed  Google Scholar 

  43. Shahabadi, N., & Amiri, S. (2015). Spectroscopic and computational studies on the interaction of DNA with pregabalin drug. Spectrochimica Acta A, 138, 840–845. https://doi.org/10.1016/j.saa.2014.10.104.

    Article  CAS  Google Scholar 

  44. Bordbar, A. K., Dezhampanah, H., Asadi, M., Safaei, E., Sohrabi, N., & Khodadost, Y. (2007). Thermodynamics investigation of a series of metalloporphyrazine-bovine serum albumin complexes. Journal of Porphyrins and Phthalocyanines, 11, 556–565. https://doi.org/10.1142/S1088424607000655.

    Article  CAS  Google Scholar 

  45. Anjomshoa, M., Torkzadeh-Mahani, M., Sahihi, M., Rizzoli, C., Ansari, M., Janczak, J., Sherafat Esfahani, S., Ataei, F., Dehkhodaei, M., & Amirheidari, B. (2018). Tris-chelated complexes of nickel (II) with bipyridine derivatives: DNA binding and cleavage, BSA binding, molecular docking, and cytotoxicity. Journal of Biomolecular Structure & Dynamics, 11, 1–51. https://doi.org/10.1080/07391102.2018.1534700.

    Article  CAS  Google Scholar 

  46. Ghosh, P., Devi, G. P., Priya, R., Amrita, A., Sivaramakrishna, A., Babu, S., & Siva, R. (2013). Spectroscopic and in silico evaluation of interaction of DNA with six derivatives. Applied Biochemistry and Biotechnology, 170, 1127–1137. https://doi.org/10.1007/s12010-013-0259-2.

    Article  CAS  PubMed  Google Scholar 

  47. Hosseinzadeh, R., Bordbar, A. K., Matin, A. A., & Maleki, R. (2007). Potentiometric study of cetylpyridinium chloride cooperative binding to anionic azo-dyes. Journal of the Brazilian Chemical Society, 18, 359–363. https://doi.org/10.1590/S0103-50532007000200017.

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors of this article would like to thank Payame Noor University of Isfahan.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Nasrin Sohrabi or Mahboube Eslami Moghadam.

Additional information

Publisher’s Note

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

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Shiekhzadeh, A., Sohrabi, N., Moghadam, M.E. et al. Kinetic and Thermodynamic Investigation of Human Serum Albumin Interaction with Anticancer Glycine Derivative of Platinum Complex by Using Spectroscopic Methods and Molecular Docking. Appl Biochem Biotechnol 190, 506–528 (2020). https://doi.org/10.1007/s12010-019-03078-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12010-019-03078-y

Keywords

Navigation