The binding assessment with human serum albumin of novel six-coordinate Pt(IV) complexes, containing bidentate nitrogen donor/methyl ligands

Document Type : Original article

Authors

1 Protein Chemistry Laboratory (PCL), Department of Biology, Shiraz University, Shiraz, Iran. Institute of Biotechnology, Shiraz University, Shiraz, Iran

2 Department of Biotechnology, Faculty of Advanced Sciences and Technologies, University of Isfahan, Isfahan, 81746-73441, Iran

3 Department of Chemistry, College of Sciences, Shiraz University, Shiraz, Iran

4 Protein Chemistry Laboratory (PCL), Department of Biology, College of Sciences, Shiraz University, Shiraz, Iran

Abstract

The interactions between platinum complexes and human serum albumin (HSA) play crucial roles in the distribution, metabolism, and activity of platinum-based anticancer drugs. Octahedral platinum (IV) complexes represent a significant class of anticancer agents that display molecular pharmacological properties different from cisplatin. In this study, the interaction between two Pt(IV) complexes with the general formula [Pt(X)2Me2 (tbu2bpy)], where tbu2bpy = 4,4′-ditert-butyl-2,2′-bipyridine, with two leaving groups of X = Cl (Com1) or Br (Com2), and HSA were investigated, using Ultraviolet-Visible (UV-Vis) spectroscopy, fluorescence spectroscopy, circular dichroism (CD) and molecular docking simulation. The spectroscopic and thermodynamic data revealed that the HSA/Pt(IV) complexes interactions were spontaneous process and Com2 demonstrated stronger interaction and binding constant in comparison with Com1. Also, the results suggest approximately similar structural alteration of HSA in the presence of these Pt complexes. Molecular docking revealed that both Pt(IV) complexes bind with HSA in subdomain IB, literally the same as each other. This study suggests that variation in the leaving group, displaying differing departure rate, has no significant contribution in denaturing prosperities of the Pt(IV) complexes against HSA. 

Keywords


  1. Wang X, Guo Z. Towards the rational design of platinum (II) and gold (III) complexes as antitumour agents. Dalton Trans 2008; (12):1521-1532.
  2. Teni Boulikas AP, Evagelos B, Petros C. Designing platinum compounds in cancer: structures and mechanisms. Cancer Ther 2007; 5:537-583.
  3. Wang X. Fresh platinum complexes with promising antitumor activity. Anticancer Agents Med Chem 2010; 10(5):396-411.
  4. Kostova I. Platinum complexes as anticancer agents. Recent Pat Anticancer Drug Discov 2006; 1(1):1-22.
  5. Hall MD, Amjadi S, Zhang M, Beale PJ, Hambley TW. The mechanism of action of platinum (IV) complexes in ovarian cancer cell lines. J Inorg Biochem 2004; 98(10):1614-1624.
  6. Zhong W, Zhang Q, Yan Y, Yue S, Zhang B, Tang W. Interaction of sodium chloroplatinate and iproplatin with metallothionein in vivo. J Inorg Biochem 1997; 66(3):159-164.
  7. George CM, Haraf DJ, Mauer AM, Krauss SA, Hoffman PC, Rudin CM, Szeto L, Vokes EE. A phase I trial of the oral platinum analogue JM216 with concomitant radiotherapy in advanced malignancies of the chest. Invest New Drugs 2001; 19(4):303-310.
  8. Pendyala L, Kidani Y, Perez R, Wilkes J, Bernacki RJ, Creaven PJ. Cytotoxicity, cellular accumulation and DNA binding of oxaliplatin isomers. Cancer Lett 1995; 97(2):177-184.
  9. Carter DC, Ho JX. Structure of serum albumin. Adv Protein Chem. 1994; 45:153-203.
  10. Margarson MP, Soni N. Serum albumin: touchstone or totem? Anaesthesia 1998; 53(8):789-803.
  11. Fasano M, Curry S, Terreno E, Galliano M, Fanali G, Narciso P, Notari S, Ascenzi P. The extraordinary ligand binding properties of human serum albumin. IUBMB Life 2005; 57(12):787-796.
  12. Ahmed-Ouameur A, Diamantoglou S, Sedaghat-Herati MR, Nafisi S, Carpentier R, Tajmir-Riahi HA. The effects of drug complexation on the stability and conformation of human serum albumin: protein unfolding. Cell Biochem Biophys 2006; 45(2):203-213.
  13. Bolli A, Marino M, Rimbach G, Fanali G, Fasano M, Ascenzi P. Flavonoid binding to human serum albumin. Biochem Biophys Res Commun 2010; 398(3):444-449.
  14. Brown JR, Shockley P. Serum albumin: structure and characterization of its ligand binding sites. New York: Wiley; 1982: 25-68.
  15. Hill GS, Vittal JJ, Puddephatt RJ. Methyl (hydrido) platinum (IV) complexes:  X-ray structure of the first (μ-Hydrido) diplatinum (IV) complex. Organometallics 1997; 16(6):1209-1217.
  16. Kelly ME, Gómez-Ruiz S, Kluge R, Merzweiler K, Steinborn D, Wagner C, Schmidt H. Studies of mononuclear and dinuclear complexes of dibromodimethylplatinum(IV): preparation, characterization and crystal structures. Inorganica Chimica Acta 2009; 362(4):1323-1332.
  17. Hu Y-J, Liu Y, Wang J-B, Xiao X-H, Qu S-S. Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J Pharm Biomed Anal 2004;36(4):915-919.
  18. Divsalar A, Saboury AA, Yousefi R, Moosavi-Movahedi AA, Mansoori-Torshizi H. Spectroscopic and cytotoxic studies of the novel designed palladium (II) complexes: β-Lactoglobulin and K562 as the targets. Int J Biol Macromol 2007; 40(4):381-386.
  19. Thomsen R, Christensen MH. MolDock:  A new technique for high-accuracy molecular docking. J Med Chem 2006; 49(11):3315-3321.
  20. Keshavarz FA, M. M. Yousefi, R. Molecular dynamics simulation and docking studies on the binding properties of several anticancer drugs to human serum albumin. Mol Biol Res Commun 2012; 1(2):65-73.
  21. Yotsuyanagi T, Ohta N, Futo T, Ito S, Chen DN, Ikeda K. Multiple and irreversible binding of cis-diamminedichloroplatinum(II) to human serum albumin and its effect on warfarin binding. Chem Pharm Bull (Tokyo) 1991; 39(11):3003-3006.
  22. Ohta N, Yotsuyanagi T, Chen D, Ono R, Ito S, Ikeda K. Disulfide bond cleavage of human serum albumin and alterations of its secondary structure by cis-diamminedichloroplatinum(II). Int J Pharm 1992; 85(1–3):39-44.
  23. Zhmareva EN, Zegzhda GD, Kas'ian GB, Livenskaia OA. Interaction of proteins with platinum and palladium compounds with differing biological activities. Ukr Biokhim Zh (1978) 1996; 68(3):74-79.
  24. Trynda-Lemiesz L, Kozlowski H, Katsaros N. Interaction of cis- and trans-RuCl (2)(DMSO)(4) with human serum albumin. Met Based Drugs 2000;7(6):293-299.
  25. Bischin C, Lupan A, Taciuc V, Silaghi-Dumitrescu R. Interactions between proteins and platinum-containing anti-cancer drugs. Mini Rev Med Chem 2011;11(3):214-224.
  26. Pouryasin Z, Yousefi R, Nabavizadeh SM, Rashidi M, Hamidizadeh P, Alavianmehr MM, Moosavi-Movahedi AA. Anticancer and DNA binding activities of platinum (IV) complexes; importance of leaving group departure rate. Appl Biochem Biotechnol 2014;172(5):2604-2617.
  27. Yang F, Lee P, Ma Z, Ma L, Yang G, Wu X, Liang H. Regulation of amantadine hydrochloride binding with IIA subdomain of human serum albumin by fatty acid chains. J Pharm Sci 2013; 102(1):84-92.
  28. He W, Li Y, Tian J, Liu H, Hu Z, Chen X. Spectroscopic studies on binding of shikonin to human serum albumin. J. Photochem. Photobiol. A Chem 2005;174(1):53-61.
  29. Qian Y, Zhou X, Chen J, Zhang Y. Binding of bezafibrate to human serum albumin: insight into the non-covalent interaction of an emerging contaminant with biomacromolecules. Molecules 2012;17(6):6821-6831.