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Monatshefte für Chemie - Chemical Monthly

, Volume 150, Issue 2, pp 233–245 | Cite as

Bipyrazole-based palladium(II) complexes as DNA intercalator and artificial metallonuclease

  • Khyati P. Thakor
  • Miral V. Lunagariya
  • Bhupesh S. BhattEmail author
  • Mohan N. PatelEmail author
Original Paper
  • 16 Downloads

Abstract

Substituted 3′-methyl-1′,2-diphenyl-3,4-dihydro-1′H,2H-3,4′-bipyrazole and their square planar palladium(II) complexes of type [Pd(4n)Cl2], where 4n = bipyrazole-based ligands, have been synthesized. The compounds have been characterized by various techniques like elemental analysis, mass, absorption, IR, 1H NMR and 13C NMR spectroscopy. The complexes have been further analyzed by thermogravimetric analysis (TGA), conductance measurement and energy-dispersive X-ray spectroscopy (EDX). Interaction between compounds and herring sperm DNA has been studied by absorption titration, viscosity measurement, ethidium bromide displacement titration, and molecular docking study. The binding strength between compounds and DNA has been checked in terms of Kb, Ksv, and Kf values; while spontaneity of interaction has been checked by evaluating thermodynamic parameters like Gibb’s free energy, enthalpy change (∆H°) and entropy change (∆S°). The plasmid cleavage efficacy of complexes has been evaluated by gel electrophoresis technique. The minimum inhibitory concentration of compounds has been evaluated against pathogens such as Staphylococcus aureus, Escherichia coli, B. subtilis, S. marcescens and Pseudomonas aeruginosa. The in vivo and in vitro cytotoxic activity has been performed using cell viability assay and brine shrimp lethality bioassay.

Graphical abstract

Keywords

Absorption spectra Pd(II) metal complexes DNA interaction Fluorescence Thermodynamics Bipyrazole ligands Antimicrobial activity 

Notes

Acknowledgements

The authors are thankful to the Head, Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, Gujarat, India, for providing the laboratory facilities, U.G.C., New Delhi for providing financial assistance of UGC BSR Grant no. C/2013/BSR/Chemistry/59 and “BSR UGC One Time Grant”, vide UGC letter no. F.19-119/2014 (BSR).

Supplementary material

706_2018_2316_MOESM1_ESM.docx (3.5 mb)
Supplementary material 1 (DOCX 3563 kb)

References

  1. 1.
    Florea A-M, Büsselberg D (2011) Cancers 3:1351CrossRefGoogle Scholar
  2. 2.
    Gautier A, Cisnetti F (2012) Metallomics 4:23CrossRefGoogle Scholar
  3. 3.
    Icsel C, Yilmaz VT, Kaya Y, Samli H, Harrison WTA, Buyukgungor O (2015) Dalton Trans 44:6880CrossRefGoogle Scholar
  4. 4.
    Raj Kumar R, Mohamed Subarkhan MK, Ramesh R (2015) RSC Adv 5:46760CrossRefGoogle Scholar
  5. 5.
    Wagner-Schuh B, Beck W (2017) Z Anorg Allg Chem 643:632CrossRefGoogle Scholar
  6. 6.
    Krogul A, Cedrowski J, Wiktorska K, Oziminski WP, Skupińska J, Litwinienko G (2013) Bioorg Med Chem Lett 23:2765CrossRefGoogle Scholar
  7. 7.
    Bekhit AA, Ashour HMA, Abdel Ghany YS, Bekhit AE-DA, Baraka A (2008) Eur J Med Chem 43:456CrossRefGoogle Scholar
  8. 8.
    Vanicek S, Kopacka H, Wurst K, Vergeiner S, Oehninger L, Ott I, Bildstein B (2015) Z Anorg Allg Chem 641:1282CrossRefGoogle Scholar
  9. 9.
    Kalinowska-Lis U, Szabłowska-Gadomska I, Lisowska K, Ochocki J, Małecki M, Felczak A (2017) Z Anorg Allg Chem 643:993CrossRefGoogle Scholar
  10. 10.
    Lippard SJ (1994) Principles of bioinorganic chemistry. University Science Books, CaliforniaGoogle Scholar
  11. 11.
    El-Gamel NE (2013) Monatsh Chem 144:1627CrossRefGoogle Scholar
  12. 12.
    Leela DS, Ushaiah B, Anupama G, Sunitha M, Kumari CG (2015) J Fluoresc 25:185CrossRefGoogle Scholar
  13. 13.
    Nagababu P, Latha JN, Satyanarayana S (2006) Chem Biodivers 3:1219CrossRefGoogle Scholar
  14. 14.
    Afrati T, Pantazaki AA, Dendrinou-Samara C, Raptopoulou C, Terzis A, Kessissoglou DP (2010) Dalton Trans 39:765CrossRefGoogle Scholar
  15. 15.
    Jin VX, Ranford JD (2000) Inorg Chim Acta 304:38CrossRefGoogle Scholar
  16. 16.
    Liu Z-C, Wang B-D, Li B, Wang Q, Yang Z-Y, Li T-R, Li Y (2010) Eur J Med Chem 45:5353CrossRefGoogle Scholar
  17. 17.
    Raman N, Sobha S, Mitu L (2012) Monatsh Chem 143:1019CrossRefGoogle Scholar
  18. 18.
    Tjioe L, Meininger A, Joshi T, Spiccia L, Graham B (2011) Inorg Chem 50:4327CrossRefGoogle Scholar
  19. 19.
    Patel MN, Gandhi DS, Parmar PA (2011) Spectrochim Acta A 84:243CrossRefGoogle Scholar
  20. 20.
    Chitrapriya N, Mahalingam V, Zeller M, Natarajan K (2010) Inorg Chim Acta 363:3685CrossRefGoogle Scholar
  21. 21.
    N’Soukpoé-Kossi CN, Descôteaux C, Asselin É, Tajmir-Riahi H-A, Bérubé G (2007) DNA Cell Biol 27:101CrossRefGoogle Scholar
  22. 22.
    Waring MJ (1965) J Mol Biol 13:269CrossRefGoogle Scholar
  23. 23.
    Kalaivani P, Prabhakaran R, Ramachandran E, Dallemer F, Paramaguru G, Renganathan R, Poornima P, Padma VV, Natarajan K (2012) Dalton Trans 41:2486CrossRefGoogle Scholar
  24. 24.
    Shanmugapriya A, Kalaiarasi G, Kalaivani P, Dallemer F, Prabhakaran R (2016) Inorg Chim Acta 449:107CrossRefGoogle Scholar
  25. 25.
    Koumousi ES, Zampakou M, Raptopoulou CP, Psycharis V, Beavers CM, Teat SJ, Psomas G, Stamatatos TC (2012) Inorg Chem 51:7699CrossRefGoogle Scholar
  26. 26.
    Wolfe A, Shimer GH, Meehan T (1987) Biochemistry 26:6392CrossRefGoogle Scholar
  27. 27.
    Zhang Y, Zhang G, Li Y, Hu Y (2013) J Agric Food Chem 61:2638CrossRefGoogle Scholar
  28. 28.
    Rajendiran V, Murali M, Suresh E, Sinha S, Somasundaram K, Palaniandavar M (2008) Dalton Trans 1:148CrossRefGoogle Scholar
  29. 29.
    Rajendiran V, Murali M, Suresh E, Palaniandavar M, Periasamy VS, Akbarsha MA (2008) Dalton Trans 16:2157CrossRefGoogle Scholar
  30. 30.
    Inclán M, Albelda MT, Frías JC, Blasco S, Verdejo B, Serena C, Salat-Canela C, Díaz ML, García-España A, García-España E (2012) J Am Chem Soc 134:9644CrossRefGoogle Scholar
  31. 31.
    Dimiza F, Fountoulaki S, Papadopoulos AN, Kontogiorgis CA, Tangoulis V, Raptopoulou CP, Psycharis V, Terzis A, Kessissoglou DP, Psomas G (2011) Dalton Trans 40:8555CrossRefGoogle Scholar
  32. 32.
    Tan C, Liu J, Li H, Zheng W, Shi S, Chen L, Ji L (2008) J Inorg Biochem 102:347CrossRefGoogle Scholar
  33. 33.
    Tarushi A, Lafazanis K, Kljun J, Turel I, Pantazaki AA, Psomas G, Kessissoglou DP (2013) J Inorg Biochem 121:53CrossRefGoogle Scholar
  34. 34.
    Psomas G (2008) J Inorg Biochem 102:1798CrossRefGoogle Scholar
  35. 35.
    Moradi S, Ajloo D, Lashkarbolouki T, Alizadeh R, Saboury AA (2013) Monatsh Chem 144:1499CrossRefGoogle Scholar
  36. 36.
    Lakowicz JR (2006) Principles of fluorescence spectroscopy. Springer, New YorkCrossRefGoogle Scholar
  37. 37.
    Clever GH, Söltl Y, Burks H, Spahl W, Carell T (2006) Chem Eur J 12:8708CrossRefGoogle Scholar
  38. 38.
    Macías B, Villa MV, Gómez B, Borrás J, Alzuet G, González-Álvarez M, Castiñeiras A (2007) J Inorg Biochem 101:444CrossRefGoogle Scholar
  39. 39.
    Moreno RGM, Alipázaga MV, Gomes OF, Linares E, Medeiros MHG, Coichev N (2007) J Inorg Biochem 101:866CrossRefGoogle Scholar
  40. 40.
    Barton JK, Raphael AL (1984) J Am Chem Soc 106:2466CrossRefGoogle Scholar
  41. 41.
    Tweedy B (1964) Phytopathology 55:910Google Scholar
  42. 42.
    Patel MN, Patel SH, Chhasatia MR, Parmar PA (2008) Bioorg Med Chem Lett 18:6494CrossRefGoogle Scholar
  43. 43.
    Meyer BN, Ferrigni NR, Putnam JE, Jacobsen LB, Nichols DE, McLaughlin JL (1982) Planta Med 45:31CrossRefGoogle Scholar
  44. 44.
    Xu C-J, Shi Y-Q (2011) J Chem Crystallgr 41:1816CrossRefGoogle Scholar
  45. 45.
    Trilleras J, Quiroga J, Cobo J, Low JN, Glidewell C (2005) Acta Cryst E 61:1892CrossRefGoogle Scholar
  46. 46.
    Mehta JV, Gajera SB, Patel MN (2016) Med Chem Commun 7:1367CrossRefGoogle Scholar
  47. 47.
    Patel MN, Bhatt BS, Dosi PA (2013) Spectrochim Acta A 110:20CrossRefGoogle Scholar
  48. 48.
    Patel MN, Bhatt BS, Dosi PA (2012) Z Anorg Allg Chem 638:152CrossRefGoogle Scholar
  49. 49.
    Baguley BC, Le Bret M (1984) Biochemistry 23:937CrossRefGoogle Scholar
  50. 50.
    Gajera SB, Mehta JV, Patel MN (2015) RSC Adv 5:21710CrossRefGoogle Scholar
  51. 51.
    Vekariya PA, Karia PS, Vaghasiya JV, Soni S, Suresh E, Patel MN (2016) Polyhedron 110:73CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2019

Authors and Affiliations

  1. 1.Department of ChemistrySardar Patel UniversityVallabh VidyanagarIndia

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