Skip to main content
Log in

Cu(II) complexes of glyco-imino-aromatic conjugates in DNA binding, plasmid cleavage and cell cytotoxicity

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

Binding of metal complexes of C2-glucosyl conjugates with DNA has been established by absorption and fluorescence studies. Conformational changes occurred in DNA upon binding have been studied by circular dichroism. All these studies are suggestive that the metal complexes bind to DNA through intercalation. Binding of di-nuclear copper complex 5 was found to be stronger when compared to the other complexes studied. Copper complexes were found to cleave the plasmid DNA in the absence of oxidizing or reducing agent, whereas, zinc complexes do not cleave. Metal complexes have shown toxicity to the HeLa and MCF–7 cell lines. Morphological studies, western blot and FACS analysis are suggestive of apoptotic cell death induced by the metal complexes. Di-nuclear copper complexes were found to be better as compared to the mononuclear ones in binding, plasmid cleavage and also in causing more cell death.

Spectral studies primarily suggest that the complexes of C2-glucosyl conjugates bind to DNA through intercalation. Copper complexes were found to cleave the plasmid DNA as well showed toxicity to HeLa and MCF–7 cell lines, suggestive of apoptotic cell death. Dinuclear complexes do bind better than the mononuclear ones.

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.

Figure 1
Figure 2
Figure 3
Chart 1
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14
Figure 15
Figure 16
Figure 17

Similar content being viewed by others

References

  1. Liu H-K and Sadler P J 2011 Acc. Chem. Res. 44 349

    Article  CAS  Google Scholar 

  2. Erkkila K E, Odom D T and Barton J K 1999 Chem. Rev. 99 2777

    Article  CAS  Google Scholar 

  3. Jamieson E R and Lippard S J 1999 Chem. Rev. 99 2467

    Article  CAS  Google Scholar 

  4. Chifotides H T and Dunbar K R 2005 Acc. Chem. Res. 38 146

    Article  CAS  Google Scholar 

  5. Farrer N J, Salassa L and Sadler P J 2009 Dalton Trans. 10690

  6. Henderson W, Nicholson B K and Tiekink E R T 2006 Inorg. Chim. Acta 359 204

    Article  CAS  Google Scholar 

  7. Quiroga A G and Ranninger C N 2004 Coord. Chem. Rev. 248 119

    Article  CAS  Google Scholar 

  8. Aguirre J D, Angeles-Boza A M, Chouai A, Turro C, Pellois J-P and Dunbar K R 2009 Dalton Trans. 10806

  9. Liu Y-C, Chen Z-F, Liu L-M, Peng Y, Hong X, Yang B, Liu H-G, Liang H and Orvig C 2009 Dalton Trans. 10813

  10. Liu Z, Habtemariam A, Pizarro A M, Fletcher S A, Kisova A, Vrana O, Salassa L, Bruijnincx P C A, Clarkson G J, Brabec V and Sadler P J 2011 J. Med. Chem. 54 3011

    Article  CAS  Google Scholar 

  11. Liu Z, Salassa L, Habtemariam A, Pizarro A M, Clarkson G J and Sadler P J 2011 Inorg. Chem. 50 5777

    Article  CAS  Google Scholar 

  12. Ruiz J, Rodriguez V, Cutillas N, Espinosa A and Hannon M J 2011 Inorg. Chem. 50 9164

    Article  CAS  Google Scholar 

  13. van Rijt S H, Mukherjee A, Pizarro A M and Sadler P J 2010 J. Med. Chem. 53 840

    Article  Google Scholar 

  14. Gottschaldt M, Pfeifer A, Koth D, Görls H, Dahse H-M, Möllmann U, Obatad M and Yano S 2006 Tetrahedron 62 11073

    Article  CAS  Google Scholar 

  15. Noguchi R, Hara A, Sugie A and Nomiya K 2006 Inorg. Chem. Commun. 9 355

    Article  CAS  Google Scholar 

  16. Coyle B, McCann M, Kavanagh K, Devereux M, McKee V, Kayal N, Egan D, Deegan C and Finn G J 2004 J. Inorg. Biochem. 98 1361

    Article  CAS  Google Scholar 

  17. Abuskhuna S, Briody J, McCann M, Devereux M, Kavanagh K, Fontecha J B and McKee V 2004 Polyhedron 23 1249

    Article  CAS  Google Scholar 

  18. Tsyba I, Mui B B, Bau R, Noguchi R and Nomiya K 2003 Inorg. Chem. 42 8028

    Article  CAS  Google Scholar 

  19. Kumar A, Singhal N K, Ramanujam B, Mitra A, Rameshwaram N R, Nadimpalli S K, Rao C P 2009 Glycoconjugate J. 26 495

    Article  CAS  Google Scholar 

  20. Kumar A, Ramanujam B, Singhal N K, Mitra A, Rao C P 2010 Carbohydrate Res. 345 2491

    Article  CAS  Google Scholar 

  21. Singhal N K, Ramanujam B, Mariappandar V, Rao C P 2006 Org. Lett. 8 3525

    Article  CAS  Google Scholar 

  22. Ahuja R, Singhal N K, Ramanujam B, Ravikumar M, Rao C P 2007 J. Org. Chem. 72 3430

    Article  CAS  Google Scholar 

  23. Singh S, Upadhyay A K, Ajay A K, Bhat M K 2007 FEBS Lett. 581 289

    Article  CAS  Google Scholar 

  24. Kumar A, Chinta J P, Ajay A K, Bhat M K and Rao C P 2011 Dalton Trans. 2011 40 10865

    Article  CAS  Google Scholar 

  25. Mitra A, Chinta J P and Rao C P 2010 Tetrahedron Lett. 51 139

    Article  CAS  Google Scholar 

  26. Mitra A, Hinge V K, Mittal A, Bhakta S, Guionneau P and Rao C P 2011 Chem. Eur. J. 17 8044

    Article  CAS  Google Scholar 

  27. Chan H L, Liu H Q, Tzeng B C, You Y S, Peng S M, Yang M and Che C M 2002 Inorg. Chem. 41 316

    Article  Google Scholar 

  28. Selvakumar B, Rajendiran V, Maheswari P U, Stoeckli-Evans H and Palaniandavar M 2006 J. Inorg. Biochem. 100 316

    Article  CAS  Google Scholar 

  29. Kelly J, Tossi A, McConnell D and Uigin O 1985 Nucleic Acid Res. 13 6017

    Article  CAS  Google Scholar 

  30. Loganathan R, Ramakrishnan S, Suresh E, Riyasdeen A, Akbarsha M A and Palaniandavar M 2012 Inorg. Chem. 51 5512

    Article  CAS  Google Scholar 

  31. Ramakrishnan S, Rajendiran V, Palaniandavar M, Periasamy V S, Srinag B S, Krishnamurthy H and Akbarsha M A 2009 Inorg. Chem. 48 1309

    Article  CAS  Google Scholar 

  32. Maheswari P U, van der Ster M, Smulders S, Barends S, van Wezel G P, Massera C, Roy S, Dulk H D, Gamez P and Reedijk J 2008 Inorg. Chem. 47 3719

    Article  CAS  Google Scholar 

  33. Aliaga-Alcalde N, Marqués-Gallego P, Kraaijkamp M, Herranz-Lancho C, Dulk H D, Gorner H, Roubeau O, Teat S J, Weyhermuller T and Reedijk J 2010 Inorg. Chem. 49 9655

    Article  CAS  Google Scholar 

  34. Maheswari P U, Roy S, Dulk H D, Barends S, Wezel G V, Kozlevcar B, Gamez P and Reedijk J 2006 J. Am. Chem. Soc. 128 710

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to CHEBROLU P RAO.

Rights and permissions

Reprints and permissions

About this article

Cite this article

KUMAR, A., MITRA, A., AJAY, A.K. et al. Cu(II) complexes of glyco-imino-aromatic conjugates in DNA binding, plasmid cleavage and cell cytotoxicity. J Chem Sci 124, 1217–1228 (2012). https://doi.org/10.1007/s12039-012-0319-0

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-012-0319-0

Keywords

Navigation