Skip to main content
Log in

Synthesis and bio-catalytic activity of isostructural cobalt(III)-phenanthroline complexes

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

Abstract

We have synthesized two isostructural mononuclear cobalt(III) complexes [1]NO3⋅3H2O and [1]NO3⋅CH3CO2H⋅H2O {[1] + = [Co(1,10-phenanthroline)2Cl2]+} and characterized by single crystal X-ray structural analyses. Mass spectral studies of the complexes indicate both the compounds to produce identical cationic species viz., [Co(phen)2Cl2]+ in methanol solution. [1]+ has been evaluated as model system for the catechol oxidase enzyme by using 3,5-di-tert-butylcatechol (3,5-DTBC) as the substrate in methanol medium, which revealed that the cationic complex efficiently inhibits catalytic activity with kcat value 9.65 ×102 h−1. [1]+ cleaved pBR 322 DNA without addition of an activating agent. Further, the anti-cancer activity of [1]+ on human hepatocarcinoma cell line (HepG2) has been examined. The induction of apoptosis induced in the cell line was assessed base on the changes in cell morphology, which showed the efficacy of [1] + to induce apoptosis in 53% of cells during 24 h treatment. Interestingly, the observed IC50 values reveal that [1]+ brings about conformational change on DNA strongly and exhibits remarkable cytotoxicity.

The cationic cobalt(III) complex exhibits good catalytic activity in saturated oxygen environment towards 3,5-ditertbutylcatechol with kcat value 9.65×102 h-1. It also exhibits important cytotoxicity against human hepatocarcinoma cell line (HepG2).

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.

Institutional subscriptions

Scheme 1
Figure 1
Figure 2
Scheme 2
Figure 3
Figure 4
Scheme 3
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9

Similar content being viewed by others

References

  1. (a) Long E C and Barton J K 1990 Acc. Chem. Res. 23 271; (b) Selvi P T, Evans H S, Palaniandavar M 2005 J. Inorg. Biochem. 99 2110

  2. (a) Sammes P G and Yahioglu G 1994 Chem. Soc. Rev. 23 327; (b) Shields T P, Barton J K, 1995 Biochemistry 34 15037; (c) Vaidyanathan V G, Nair B U 2003 J. Inorg. Biochem. 94 121

  3. (a) Barton J K and Raphael A L 1984 J. Am. Chem. Soc. 106 2466; (b) Wang X L, Chao H, Li H, Hong X L, Liu Y J, Tan L F and Ji L N 2004 J. Inorg. Biochem. 98 1143

  4. (a) Sitlani A S, Long E C, Pyle A M, Barton J K 1992 J. Am. Chem. Soc. 114 2303; (b) Dey D, Pal S, Chandraleka S, Dhanasekaran D, Kole N and Biswas B 2014 J. Indian Chem. Soc. 91 1267

  5. (a) Chan S and Wong W T 1995 Coord. Chem. Rev. 138 219; (b) Zhen Q-X, Ye B-H, Zhang Q-L, Liu J-G, Li H, Ji L-N and Wang L 1999 J. Inorg. Biochem. 76 47; (c) Dey D, Kaur G, Ranjani A, Gyathri L, Chakraborty P, Adhikary J, Pasan J, Dhanasekaran D, Choudhury A R, Akbarsha M A, Kole N and Biswas B 2014 Eur. J. Inorg. Chem. 3350

  6. (a) Pratviel G, Bernadou J and Meunier B 1998 Adv. Inorg. Chem. 45 251; (b) Shimakoshi H, Kaieda T, Matsuo T, Sato H and Hisaeda Y 2003 Tetrahedron Lett. 44 5197; (c) Biswas B, Mitra P and Ghosh R 2013 J. Indian Chem. Soc. 90 1311

  7. (a) Liang F, Wang P, Zhou X, Li T, Li Z Y, Lin H K, Gao D Z, Zheng C Y and Wu CT 2004 Bioorg. Med. Chem. Lett. 14 1901; (b) Biswas B, Mitra M, Pal A, Basu A, Rajalakshmi S, Mitra P, Aliaga-Alcalde N, Kumar G S, Nair B U and Ghosh R 2013 Ind. J. Chem. Sect. A 52A 1576

  8. (a) Biswas B, Patra M, Dutta S, Ganguly M and Kole N 2013 J. Chem. Sci. 125 1445; (b) Pal A, Biswas B, Mondal S K, Lin C-H and Ghosh R 2012 Polyhedron 31 671

  9. (a) Parshall G and Ittel S (Eds.)1992 Homogeneous Catalysis 2nd edition (New York: John Wiley); (b) Biswas B, Al-Hunaiti A, Räisänen M T, Ansalone S, Leskelä M, Repo T, Chen Y-T, Tsai H-L, Naik A D, Railliet A P, Garcia Y, Ghosh R and Kole N 2012 Eur. J. Inorg. Chem. 4479

  10. Cornils B and Herrmann W (Eds.) 1996 Applied Homogeneous Catalysis with Organometallic Compounds Vol. 1 (Weinheim: VCH)

  11. Anastas P and Warner J 1997 In Green Chemistry: Theory and Practice (Oxford: Oxford University Press)

  12. (a) Puzari A and Jubaraj B 2002 J. Mol. Cat. A Chem. 187 149; (b) Biswas B, Mitra M, Adhikary J, Krishna G R, Bag P P, Reddy C M, Aliaga-Alcalde N, Chattopadhyay T, Das D and Ghosh R 2013 Polyhedron 53 264

  13. (a) Gates B 1992 In Catalytic Chemistry (Hoboken: John Wiley); (b) Dey D, Kaur G, Patra M, Choudhury A R, Kole N and Biswas B 2014 Inorg. Chim. Acta 421 335

  14. Foote C, Valentine J, Greenberg A and Liebman J 1995 In Active Oxygen in Chemistry, SEARCH Series, Vol. 2 (Kluver)

  15. (a) Mayer A M and Harel E 1979 Phytochem 18 193; (b) Simándi T L and Simándi L I 1998 React Kinet. Catal. Lett. 65 301; (c) Simándi L I and Simándi T L 1998 J. Chem. Soc. Dalton Trans. 3275; (d) Biswas A, Das L K and Ghosh A 2013 Polyhedron 61 253

  16. (a) Selmeczi K, Reglier M, Giorgi M and Speier G 2003 Coord. Chem. Rev. 245 191; (b) Gerdemann C, Eicken C, Krebs B 2002 Acc. Chem. Res. 35 183; (c) Guha A, Chattopadhyay T, Paul N D, Mukherjee M, Goswami S, Mondal TK, Zangrando E and Das D 2012 Inorg. Chem. 51 8750

  17. (a) Than R, Feldmann A A and Krebs B 1999 Coord. Chem. Rev. 182 211; (d) Solomon E I, Sundaram U M, Machonkin T E 1996 Chem. Rev. 96 2563; (f) Klabunde T, Eicken C, Sacchettini J C and Krebs B 1998 Nat. Struct. Biol. 5 1084; (g) C Eicken, Krebs B and Sacchettini J C 1999 Curr. Opin. Struct. Biol. 9 677

  18. (a) Dervall B J 1961 Nature 189 311; (b) Koval I A, Gamez P, Belle C, Selmeczi K, Reedijk J 2006 Chem. Soc. Rev. 35 814; (c) Kitajima N and Moro-oka Y 1994 Chem. Rev. 94 737

  19. Youssef NS El-Zahany E, El-Seidy A M A, Caselli A and Cenini S 2009 J. Mol. Cat. A 308 159

  20. (a) Chan T L, To C T, Liao B-S, Liu S-T and Chan K S 2012 Eur. J. Inorg. Chem. 485; (b) Arzberger S, Soper J, Anderson O P, la Cour A and Wicholas M 1999 Inorg. Chem. 38 757

  21. (a) Simandi L I, Barna T, Argay G and Simandi T L 1995 Inorg. Chem. 34 6337; (b) Chakrabarty R, Sarmah P, Saha B, Chakravorty S and Das B K 2009 Inorg. Chem. 48 6371

  22. Ghosh S, Barve A C, Kumbhar A A, Kumbhar A S, Puranik V G, Datar P A, Sonawane U B and Joshi R R 2006 J. Inorg. Biochem. 100 331

  23. SHELXTL 5.10 Bruker Analytical X −ray Instruments Inc.,Karlsruche, Germany (1997)

  24. Farrugia L J, ORTEP-32 for Windows, University of Glasgow, Scotland (1998)

  25. Mosmann T 1983 J. Immun. Met. 65 55

  26. Spector D L, Goldman R D and Leinwand L A 1998 In Cell: A Laboratory Manual. Culture and Biochemical Analysis of Cells Vol. 1 (New York: Cold Spring Harbor Laboratory Press)

  27. Nakamoto K 1997 In Infrared and Raman Spectra of Inorganic and Coordination Compounds part B: Applications in Coordination, Organometallic and Bioinorganic Chemistry (New York: John Wiley) p. 116

  28. Sole J G, Bausa L E and Jaque D 2005 In An Introduction to Optical Spectroscopy of Inorganic Solids (John Wiley)

  29. Tsuruya S, Yanai S-I and Masai M 1986 Inorg. Chem. 25 141

  30. Zippel F, Ahlers F, Werner R, Haase W, Nolting H-F and Krebs B 1996 Inorg. Chem. 35 3409

  31. Banu K S, Chattopadhyay T, Banerjee A, Mukherjee M, Bhattacharya S, Patra G K, Zangrando E and Das D 2009 Dalton Trans. 8755

  32. Majumder S, Mondal S, Lemoineb P and Mohanta S 2013 Dalton Trans. 42 4561

  33. Ghosh R, Mitra M and Raghavaiah P 2015 New J. Chem. 39 200

  34. Dey S K and Mukherjee A 2014 New J. Chem. 38 4985

  35. Banerjee A, Guha A, Adhikary J, Khan A, Manna K, Dey S, Zangrando E and Das D 2013 Polyhedron 60 102

  36. Vaidyanathan V G and Nair B U 2003 J. Inorg. Biochem. 94 121

  37. (a) Liu X W, Li J, Li H, Zheng K C, Chao H and Ji L N 2006 J Inorg Biochem 100 385; (b) Chao H, Mei W J, Huang Q W and Ji L N 2002 J Inorg Biochem 92 165

  38. (a) Basile L A, Raphael A L and Barton J K 1987 J. Am. Chem. Soc. 109 7550; (b) Hartwig J F and Lippard S J 1992 J. Am. Chem. Soc. 114 5646; (c) Reedijk J 2009 Eur. J. Inorg. Chem. 1303

  39. (a) Ramakrishnan S, Suresh E, Riyasdeen A, Periasamy V S, Akbarsha M A, Palaniandavar M 2011 Dalton Trans. 40 3245; (b) Satyanaryana S, Dabrowiak J C and Chaires J B 1993 Biochemistry 32 2573; (c) Wang X 2010 Anticancer Agents Med. Chem. 10 396

  40. (a) Wang X and Guo Z 2013 Chem. Soc. Rev. 42 202; (b) Tabassum S, Parveen S and Arjmand F 2005 Acta Biomater. 1 677; (c) Pasternack R F, Gibbs E J and Villafranca J J 1983 Biochemistry 22 2406

  41. (a) Hannon M J 2007 Pure Appl. Chem. 79 2243; (b) Oberoi H S, Nukolova N V, Kabanov A V and Bronich T K 2013 Adv. Drug Delivery Rev. 65 1667

Download references

Acknowledgements

The work was supported financially by the Department of Science and Technology (DST), New Delhi, India under FAST TRACK SCHEME for YOUNG SCIENTIST (NO. SB/FT/CS-088/2013 dtd. 21/05/2014). B. Biswas also gratefully acknowledges the financial support from the University Grant Commission, New Delhi, India (F. No. PSW-84/12-13(ERO) dated 05/02/2013). B. Biswas is highly thankful to IACS, Kolkata for facilitating proton NMR and mass spectrometric studies.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to BHASKAR BISWAS.

Additional information

Supplementary Information

Crystallographic data are available free of charge from The Director, CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: +44-1223-336033; E-mail: deposit@ccdc.cam.ac.uk or www: http://www.ccdc.cam.ac.uk) upon request, quoting deposition number CCDC 829003 for [1]NO3⋅3H2O and and CCDC 975400 for [1]NO3⋅CH3CO2H⋅H2O. Figures S1-S9 and tables S1-S3 are available in the online version at www.ias.ac.in/chemsci.

Electronic supplementary material

Below is the link to the electronic supplementary material.

(DOC 2.96 MB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

DEY, D., ROY, A.B., RANJANI, A. et al. Synthesis and bio-catalytic activity of isostructural cobalt(III)-phenanthroline complexes. J Chem Sci 127, 649–661 (2015). https://doi.org/10.1007/s12039-015-0817-y

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12039-015-0817-y

Keywords

Navigation