Skip to main content
SpringerLink
Log in

Molecular docking, free radical scavenging, and DNA interaction studies of drug-based coordination compounds

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Five-coordinated distorted square pyramidal ternary copper(II) complexes of ciprofloxacin and derivatives of phenanthroline (2,9-dimethyl-1,10-phenanthroline, 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline, 4,5-diazafluoren-9-one, 1,10-phenanthroline-5,6-dione, and 5-nitro-1,10-phenanthroline) with one chlorine at axial position were prepared and were characterized well. Considerable raise in antimicrobial activity was observed because chelation favors the transfer of metal ion to cross the cell membrane barrier, which interferes in normal cell process. Complexes were found to exhibit intercalative mode of binding with DNA with an extent of K b values ranging from 0.725 to 1.827 × 105 M−1. The DNA-binding property of all the complexes have been also examined theoretically using molecular docking study and recommends intercalation binding mode between all complexes and nucleotide base pairs of HS DNA. DNA scissoring activity of complexes was found to be greater than ciprofloxacin by 8 % and more, also the synthesized complexes were found to be potent oxygen radical scavenger with effective concentration ranging of 0.7583–1.6865 µM.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5

Similar content being viewed by others

References

  1. Lietman P (1995) Drugs 49:159

    Article  CAS  Google Scholar 

  2. López-Gresa MP, Ortiz R, Perelló L, Latorre J, Liu-González M, García-Granda S, Pérez-Priede M, Cantón E (2002) J Inorg Biochem 92:65

    Article  Google Scholar 

  3. Turel I, Golobič A, Klavžar A, Pihlar B, Buglyó P, Tolis E, Rehder D, Sepčić K (2003) J Inorg Biochem 95:199

    Article  CAS  Google Scholar 

  4. Xiao D-R, Wang E-B, An H-Y, Su Z-M, Li Y-G, Gao L, Sun C-Y, Xu L (2005) Chem Eur J 11:6673

    Article  CAS  Google Scholar 

  5. Psomas G, Tarushi A, Efthimiadou EK (2008) Polyhedron 27:133

    Article  CAS  Google Scholar 

  6. Čurman D, Živec P, Leban I, Turel I, Polishchuk A, Klika KD, Karaseva E, Karasev V (2008) Polyhedron 27:1489

    Article  Google Scholar 

  7. Wallis SC, Gahan LR, Charles BG, Hambley TW (1995) Polyhedron 14:2835

    Article  CAS  Google Scholar 

  8. Drevensek P, Leban I, Turel I, Giester G, Tillmanns E (2003) Acta Cryst C 59:m376

    Article  Google Scholar 

  9. Saha DK, Sandbhor U, Shirisha K, Padhye S, Deobagkar D, Anson CE, Powell AK (2004) Bioorg Med Chem Lett 14:3027

    Article  CAS  Google Scholar 

  10. Saha D, Padhye S, Anson C, Powell A (2003) Transit Met Chem 28:579

    Article  CAS  Google Scholar 

  11. Hernández-Gil J, Perelló L, Ortiz R, Alzuet G, González-Álvarez M, Liu-González M (2009) Polyhedron 28:138

    Article  Google Scholar 

  12. Anacona J, Toledo C (2001) Transit Met Chem 26:228

    Article  CAS  Google Scholar 

  13. Chen Z-F, Yu L-C, Zhong D-C, Liang H, Zhu X-H, Zhou Z-Y (2006) Inorg Chem Commun 9:839

    Article  CAS  Google Scholar 

  14. Ames BN, Shigenaga MK, Hagen TM (1993) Proc Natl Acad Sci 90:7915

    Article  CAS  Google Scholar 

  15. Halliwell B, Gutteridge JMC (1989) Free radicals in biology and medicine, 2nd edn. Clarendon Press, Oxford

    Google Scholar 

  16. Kehrer JP (1993) Crit Rev Toxicol 23:21

    Article  CAS  Google Scholar 

  17. Patel RN, Singh N, Gundla VLN (2007) Polyhedron 26:757

    Article  CAS  Google Scholar 

  18. Kato M, Muto Y (1988) Coord Chem Rev 92:45

    Article  CAS  Google Scholar 

  19. Weder JE, Dillon CT, Hambley TW, Kennedy BJ, Lay PA, Biffin JR, Regtop HL, Davies NM (2002) Coord Chem Rev 232:95

    Article  CAS  Google Scholar 

  20. Mautner FA, Vicente R, Louka FRY, Massoud SS (2008) Inorg Chim Acta 361:1339

    Article  CAS  Google Scholar 

  21. Patel MN, Patel SH, Chhasatia MR, Parmar PA (2008) Bioorg Med Chem Lett 18:6494

    Article  CAS  Google Scholar 

  22. Turel I (2002) Coord Chem Rev 232:27

    Article  CAS  Google Scholar 

  23. Chohan ZH, Supuran CT, Scozzafava A (2005) J Enzym Inhib Med Chem 20:303

    Article  CAS  Google Scholar 

  24. Freedman HH (1961) J Am Chem Soc 83:2900

    Article  CAS  Google Scholar 

  25. Chohan ZH, Arif M, Akhtar MA, Supuran CT (2006) Bioinorg Chem Appl 2006

  26. Panchal PK, Parekh HM, Pansuriya PB, Patel MN (2006) J Enzym Inhib Med Chem 21:203

    Article  CAS  Google Scholar 

  27. Pyle AM, Rehmann JP, Meshoyrer R, Kumar CV, Turro NJ, Barton JK (1989) J Am Chem Soc 111:3051

    Article  CAS  Google Scholar 

  28. Satyanarayana S, Dabrowiak JC, Chaires JB (1993) Biochemistry 32:2573

    Article  CAS  Google Scholar 

  29. Pettersen EF, Goddard TD, Huang CC, Couch GS, Greenblatt DM, Meng EC, Ferrin TE (2004) J Comput Chem 25:1605

    Article  CAS  Google Scholar 

  30. Tabassum S, Zaki M, Afzal M, Arjmand F (2013) Dalton Trans 42:10029

    Article  CAS  Google Scholar 

  31. Prabahkara M, Bhojya Naik H (2008) Biometals 21:675

    Article  CAS  Google Scholar 

  32. Sitlani A, Long EC, Pyle AM, Barton JK (1992) J Am Chem Soc 114:2303

    Article  CAS  Google Scholar 

  33. Huheey JE (1983) Inorganic chemistry principles of structure and reactivity, 3rd edn. Harper and Row, New York

    Google Scholar 

  34. Ramadan AM, El-Naggar MM (1996) J Inorg Biochem 63:143

    Article  CAS  Google Scholar 

  35. Henderson LJ, Fronczek FR, Cherry WR (1984) J Am Chem Soc 106:5876

    Article  CAS  Google Scholar 

  36. Amouyal E, Homsi A, Chambron J-C, Sauvage J-P (1990) J Chem Soc Dalton Trans 1841

  37. Smith GF, Cagle FW (1947) J Org Chem 12:781

    Article  CAS  Google Scholar 

  38. Sinha D, Tiwari AK, Singh S, Shukla G, Mishra P, Chandra H, Mishra AK (2008) Eur J Med Chem 43:160

    Article  CAS  Google Scholar 

  39. Wolfe A, Shimer GH, Meehan T (1987) Biochemistry 26:6392

    Article  CAS  Google Scholar 

  40. Chaires JB, Dattagupta N, Crothers DM (1982) Biochemistry 21:3933

    Article  CAS  Google Scholar 

  41. Cohen G, Eisenberg H (1969) Biopolymers 8:45

    Article  CAS  Google Scholar 

  42. Eriksson M, Leijon M, Hiort C, Norden B, Graeslund A (1994) Biochemistry 33:5031

    Article  CAS  Google Scholar 

  43. Liu M-L, Jiang M, Zheng K, Li Y-T, Wu Z-Y, Yan C-W (2014) J Coord Chem 67:630

    Article  CAS  Google Scholar 

  44. Sambrook J, Russell DW (2001) A laboratory manual, 3rd edn. Cold Spring Harbor Laboratory Press, Cold Spring Harbor

    Google Scholar 

  45. Yang J, Wong RNS, Yang MS (2000) Chem Biol Interact 125:221

    Article  CAS  Google Scholar 

  46. Fridovich I (1985) CRC handbook of methods for oxygen radical research. CRC Press, Boca Raton

    Google Scholar 

  47. Le X, Liao S, Liu X, Feng X (2006) J Coord Chem 59:985

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Authors are thankful to the Head, Department of Chemistry, Sardar Patel University, India for making it convenient to work in laboratory and U.G.C. for providing financial support under “UGC Research Fellowship in Science for Meritorious Students” scheme.

Author information

Authors and Affiliations

  1. Department of Chemistry, Sardar Patel University, Vallabh Vidyanagar, 388 120, Gujarat, India

    Mohan N. Patel, Deepen S. Gandhi, Pradhuman A. Parmar & Jugal V. Mehta

Authors
  1. Mohan N. Patel
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Deepen S. Gandhi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Pradhuman A. Parmar
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jugal V. Mehta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohan N. Patel.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 6117 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Patel, M.N., Gandhi, D.S., Parmar, P.A. et al. Molecular docking, free radical scavenging, and DNA interaction studies of drug-based coordination compounds. Monatsh Chem 148, 901–908 (2017). https://doi.org/10.1007/s00706-016-1816-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-016-1816-5

Keywords

Search

Navigation