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Synthesis, Characterization and Luminescence Sensitivity with Variance in pH, DNA and BSA Binding Studies of Ru(II) Polypyridyl Complexes

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Abstract

Three ruthenium(II) polypyridyl complexes, [Ru(phen)2(mip)](ClO4)2 (1) (phen =1,10-Phenanthroline), [Ru(bpy)2(mip)](ClO4)2 (2) (bpy = 2,2’bipyridyl) and [Ru(dmb)2(mip)](ClO4)2 (3) (dmb = 4, 4′-dimethyl 2, 2′-bipyridine), were synthesized with an intercalative ligand mip (2-morpholino-1H-imidazo[4,5-f][1, 10]phenanthroline) and characterized by 1H, 13C–NMR, IR, UV-vis, mass spectra and elemental analysis. pH effect, ion selectivity (cations, anions) and solvent sensitivity of complexes were studied. The interaction of these complexes with DNA was performed using absorption, emission spectroscopy and viscosity measurements. The experimental results indicated that the two complexes interacted with calf thymus DNA (CT-DNA) by intercalative mode. BSA (Bovine Serum Albumin) protein binding of these complexes was studied by UV-visible and fluorescence techniques. The binding capacity of these complexes was explained theoretically by molecular docking method.

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References

  1. Erkkila KE, Odem DT, Barton JK (1999) Recognition and reaction of Metallointercalators with DNA. Chem Rev 99:2777

    Article  CAS  PubMed  Google Scholar 

  2. Metcalfe C, Thomas JA (2003) Kinetically inert transition metal complexes that reversibly bind to DNA. Chem Soc Rev 32:215

    Article  CAS  PubMed  Google Scholar 

  3. Xiong Y, Ji LN (1999) Synthesis, DNA-binding and DNA-mediated luminescence quenching of Ru(II) polypyridine complexes. Coord Chem Rev 185:711

    Article  Google Scholar 

  4. Blasius R, Moucheron C, Mesmasker AK (2004) Photoadducts of metallic compounds with nucleic acids-role played by the photoelectron transfer process and by the TAP and HAT ligands in the RuII complexes. Eur J Inorg Chem 20:3971

    Article  Google Scholar 

  5. Pyle AM, Long EC, Barton JK (1989) Shape-selective targeting of DNA by Phenanthrenequinone diimine rhodium(III) Photocleaving agents. J Am Chem Soc 111:4520

    Article  CAS  Google Scholar 

  6. Sitlani A, Long EC, Pyle AM, Barton JK (1992) DNA photocleavage by Phenanthrenequinone diimine complexes of rhodium(III): shape-selective recognition and reaction. J Am Chem Soc 114:2303

    Article  CAS  Google Scholar 

  7. Jin L, Yang P (1997) Synthesis and DNA binding studies of CoIII mixed-ligand complex containing dipyrido [3,2-a: 2′,3′-c]phenazine and phen. Polyhedron 16:3395

    Article  CAS  Google Scholar 

  8. Song Y-m, Lu X-l, Yang M-l, Zheng X-r (2005) Study on the interaction of platinum(IV), gold(III) and silver(I) ions with DNA. Transit Met Chem 30:499

    Article  CAS  Google Scholar 

  9. Elschenbroich C, Salzer A (1992) Organometallics: a concise introduction, 2nd edn. VCH, Weinheim

    Google Scholar 

  10. Ji LN, Xiao-Hua Z, Jin-Gang L (2001) Shape- and enantioselective interaction of Ru(II)/Co(III) polypyridyl complexes with DNA. Coord Chem Rev 216:513–536

    Article  Google Scholar 

  11. Chang GZ, Chunn LM, Xiao WY, Qian LQ, Yang S, Jun K, Yan X (2011) Electronic effect of substituents on the DNA intercalation of ruthenium(II)[BOND]polypyridyl complexes. Chem Biodivers 8:1486

    Article  Google Scholar 

  12. Liu J, Zheng W, Shi S, Tan C, Chen J, Zheng K, Ji LN (2008) Synthesis, antitumor activity and structure-activity relationships of a series of Ru(II) complexes. J Inorg Biochem 102:193

    Article  CAS  PubMed  Google Scholar 

  13. Devi CS, Kumar DA, Singh SS, Gabra N, Deepika N, Kumar YP, Satyanarayana S (2013) Synthesis, interaction with DNA, cytotoxicity, cell cycle arrest and apoptotic inducing properties of ruthenium(II) molecular “light switch” complexes. Eur J Med Chem 64:410

    Article  Google Scholar 

  14. Boer DR, Canals A, Coll M (2009) DNA-binding drugs caught in action: the latest 3D pictures of drug-DNA complexes. Dalton Trans 3:399

    Article  Google Scholar 

  15. Haider SM, Neidle S, Parkinson GN (2011) A structural analysis of G-quadruplex/ligand interactions. Biochimie 93:1239

    Article  CAS  PubMed  Google Scholar 

  16. Yan YK, Melchart M, Habtemariam A, Sadler PJ (2005) Organometallic chemistry, biology and medicine: ruthenium arene anticancer complexes. Chem Commun 38:4764

    Article  Google Scholar 

  17. Süss-Fink G (2010) Arene ruthenium complexes as anticancer agents. Dalton Trans 39:1673

    Article  PubMed  Google Scholar 

  18. Bergamo A, Gaiddon C, Schellens JHM, Beijnen JH, Sava G (2012) Approaching tumour therapy beyond platinum drugs. Status of the art and perspectives of ruthenium drug candidates. J Inorg Biochem 106:90

    Article  CAS  PubMed  Google Scholar 

  19. Srishailam A, Praveen Kumar Y, Venkat Reddy P, Nambigari N, Vuruputuri U, Singh SS, Satyanarayana S (2014) Cellular uptake, cytotoxicity, apoptosis, DNA-binding, photocleavage and molecular docking studies of ruthenium(II) polypyridyl complexes. J Photochem Photobiol B 132:111

    Article  CAS  PubMed  Google Scholar 

  20. Srishailam A, Gabra NM, Kumar YP, Reddy KL, Devi CS, Anil Kumar D, Singh SS, Satyanarayana S (2014) Synthesis, characterization; DNA binding and antitumor activity of ruthenium(II) polypyridyl complexes. J Photochem Photobiol B 141:47

  21. Rajender Reddy M, Reddy PV, Kumar YP, Srishailam A, Nambigari N, Satyanarayana S (2014) Synthesis, characterization, DNA binding, light switch “on and off”, docking studies and cytotoxicity, of ruthenium(II) and cobalt(III) polypyridyl complexes. J Fluoresc 24:803

    Article  PubMed  Google Scholar 

  22. Deepika N, Kumar YP, Devi CS, Reddy PV, Srishailam A, Satyanarayana S (2013) Synthesis, characterization, and DNA binding, photocleavage, cytotoxicity, cellular uptake, apoptosis, and on–off light switching studies of Ru(II) mixed-ligand complexes containing 7-fluorodipyrido[3,2-a:20,30-c]phenazine. J Biol Inorg Chem 18:751

    Article  CAS  PubMed  Google Scholar 

  23. Kumar YP, Shobha Devi C, Deepika N, Gabra NM, Jain N, Srishailam A, Reddy KL, Satyanarayana S (2013) Transit Met Chem 38:811–819

    Article  CAS  Google Scholar 

  24. Kumar YP, Shilpa M, Naga Babu P, Laxma Reddy K, Rajender Reddy M, Gabra NM, Satyanarayana S (2012) Study of DNA light switch Ru(II)complexes: synthesis, characterization, photocleavage and anti microbial activity. J Fluoresc 22:835

    Article  Google Scholar 

  25. Vuradi RK, Putta VR, Nancherla D, Sirasani S (2016) Luminescent behavior of Ru(II) polypyridyl morpholine complexes, synthesis, characterization, DNA, protein binding, sensor effect of ions/solvents and docking studies. J Fluoresc 26(2):689–701

  26. Perrin DD, Annarego WLF, Perrin DR (1980) Drying of solvents and laboratory chemicals, 2nd edn. Pergamon Press, New York

  27. Marmur J (1961) A procedure for the isolation of deoxyribonucleic acid from micro organisms. J Mol Biol 3:208

  28. Reichmann ME, Rice SA, Thomas CA, Doty P (1954) A further examination of the molecular weight and size of Desoxypentose nucleic acid. J Am Chem Soc 76:3047

  29. Yamada M, Tanaka Y, Yoshimoto Y, Kuroda S, Shimo I (1992) Synthesis and properties of diammino-substituted dipyrado[3,2-a: 2′,3′-c]phenazine. Bull Chem Soc Jpn 65:1006

  30. Sullivan BP, Salmon DJ, Meyer T (1978) Mixed phosphine 2, 2′-bipyridine complexes of ruthenium. Inorg Chem 17:3334

    Article  CAS  Google Scholar 

  31. Steck EA, Day AR (1943) Reactions of Phenanthraquinone and Retenequinone with aldehydes and ammonium acetate in acetic acid solution. J Am Chem Soc 65:452

    Article  CAS  Google Scholar 

  32. Wolfe A, Shimer GH, Mechan T (1987) Polycyclic aromatic hydrocarbons physically intercalate into duplex regions of denatured DNA. Biochemistry 26:6392

    Article  CAS  PubMed  Google Scholar 

  33. Mc Ghee JD, Von Hippel PH (1974) Theoretical aspects of DNA protein interactions: co-operative and non-co-operative binding of large ligands to a one-dimensional homogeneous lattice. J Mol Biol 86:469

    Article  CAS  Google Scholar 

  34. pdf file, www.bc.ca/bcsc/resources/ (Canadian Teachers Federation)

  35. Chaires JB, Dattagupta N, Crothers DM (1982) Self-Association of Daunomycin. Biochemistry 21:3927–3932

    Article  CAS  PubMed  Google Scholar 

  36. Satyanarayana S, Dabrowiak JC, Chaires JB (1993) Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: mode and specificity of binding. Biochemistry 32:2573

    Article  CAS  PubMed  Google Scholar 

  37. Luzuriaga L, Cerdá MF (2012) Analysis of the interaction between [Ru(phenanthroline)3]2+ and bovine serum albumin. Advances in Biological Chemistry 2:262

    Article  CAS  Google Scholar 

  38. Han MJ, Duan ZM, Hao Q, Zheng SZ, Wang KZ (2007) Molecular light switches for calf thymus DNA based on three Ru(II) bipyridyl complexes with variations of heteroatoms. J Phys Chem C 111:16577–16585

    Article  CAS  Google Scholar 

  39. Lepecp JB, Paoletti C (1967) A fluorescent complex between ethidium bromide and nucleic acids: physical—chemical characterization. J Mol Biol 27:87–106

    Article  Google Scholar 

  40. Xu H, Zheng K-C, Deng H, Lin L-J, Zhang Q-L, Ji L-N (2003) Effects of the ancillary ligands of polypyridyl ruthenium(II) complexes on the DNA-binding behaviours. New J Chem 27:1255

    Article  CAS  Google Scholar 

  41. Xu L, Xie Y-Y, Zhong N-J, Liang Z-H, He J, Huang H-L, Liu Y-J (2012) DNA-binding and photocleavage, cytotoxicity, apoptosis and antioxidant activity studies of ruthenium(II) complexes. Transit Met Chem 37:197

    Article  CAS  Google Scholar 

  42. Venugopal R, Mariappan M, Eringathodi S, Mallayan P, Vaiyapuri SP, Mohammad AA (2008) Non-covalent DNA binding and cytotoxicity of certain mixed-ligand ruthenium(II) complexes of 2,2′-dipyridylamine and diimines. Dalton Trans 28:2157

  43. Zheng Z-B, Kang S-Y, Zhao Y, Zhang N, Yi X, Wang K-Z (2015) pH and copper ion luminescence on/off sensing by a dipyrazinylpyridine-appended ruthenium complex. Sens Actuators B-Chem 221:614

    Article  CAS  Google Scholar 

  44. Shanga X, Li X, Xi N, Zhai Y, Zhang J, Xu X (2011) Theory and experiment: recognition properties of chemosensor containing ruthenium(II) system in water solution. Sens Actuators B-Chem 160:1112

    Article  Google Scholar 

  45. Gale PA (2011) Anion receptor chemistry. Chem Commun 47:82

    Article  CAS  Google Scholar 

  46. Lakowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Springer, University of Maryland School of Medicine, Baltimore, pp 1–954

    Book  Google Scholar 

  47. Satyanarayana S, Dabrowiak JC, Chaires JB (1992) Neither ∆- nor ʌ tris(phenanthroline)ruthenium(II) binds to DNA by classical intercalation. Biochemistry 31:9319

    Article  CAS  PubMed  Google Scholar 

  48. Hu YJ, Liu Y, Wang JB, Xiao XH, Qu SS (2004) Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J Pharm Biomed Anal 36:915

    Article  CAS  PubMed  Google Scholar 

  49. Wen MG, Zhang XB, Tian JN, Ni SH, Bian HD, Huang YL, Liang H (2009) Binding interaction of Xanthoxylin with bovine serum albumin. J Sol Chem 38:391

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Acknowledgments

We are grateful to UGC-UPE (FAR) Program Osmania University Hyderabad, University Grant Commission (UGC) New Delhi INDIA for providing the BSR (RFSMS) Fellowship for the financial support and IICT, Hyderabad for providing Fluorescence spectroscopy instrument.

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Authors and Affiliations

  1. Department of Chemistry, Osmania University, Hyderabad, Telangana State, 500007, India

    Ravi Kumar Vuradi, Srishailam Avudoddi, Venkat Reddy Putta, Laxma Reddy Kotha, Praveen Kumar Yata & Satyanarayana Sirasani

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  1. Ravi Kumar Vuradi
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Correspondence to Satyanarayana Sirasani.

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Vuradi, R., Avudoddi, S., Putta, V. et al. Synthesis, Characterization and Luminescence Sensitivity with Variance in pH, DNA and BSA Binding Studies of Ru(II) Polypyridyl Complexes. J Fluoresc 27, 939–952 (2017). https://doi.org/10.1007/s10895-017-2029-y

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