Copyright (c) 2017 AJC
This work is licensed under a Creative Commons Attribution 4.0 International License.
Synthesis, Characterization, Molecular Modeling, Antimicrobial and DNA Binding Studies of Cobalt(II) Complexes of 2,3-(Diimino-4'-antipyrinyl)butane with Varying Counter Ions
Corresponding Author(s) : B.N. Anila
Asian Journal of Chemistry,
Vol. 29 No. 3 (2017): Vol 29 Issue 3
Abstract
The synthesis and characterization of perchlorate, nitrate, chloride, bromide and iodide complexes of cobalt(II) with a new Schiff base ligand 2,3-(diimino-4¢-antipyrinyl)butane prepared from 4-aminoantipyrine and 2,3-butanedione have been done by elemental analysis, electrical conductance in non-aqueous solvents, infrared and electronic and 1H NMR spectra as well as thermogravimetry. The UV-visible, magnetic susceptibility and ESR spectral data suggest an octahedral geometry around the central metal ion in chloro and bromo complexes and a tetrahedral geometry around the central metal ion for perchlorate, nitrate and iodide complexes. The molecular modeling of the proposed structure is in agreement with the above mentioned structure. Biological screening analyses of the ligands and the cobalt(II) complexes reveals that the Schiff base and its cobalt(II) complexes show significant activity against microorganisms. Binding studies of Co(II) complexes with calf thymus DNA (CT DNA) were studied by spectral methods such as absorption spectroscopy through the ethidium bromide (EB) displacement technique and viscosity measurements. The results obtained indicate that the complexes bind to DNA via intercalation.
Keywords
Download Citation
Endnote/Zotero/Mendeley (RIS)BibTeX
- R.C. Maurya, A. Pandey, J. Chaurasia and H. Martin, J. Mol. Struct., 798, 89 (2006).
- M. Hasani and A. Rezaei, Spectrochim. Acta, 65A, 1093 (2006).
- G. Turan-Zitouni, M. Sivaci, F.S. Kilic and K. Erol, Eur. J. Med. Chem., 36, 685 (2001).
- N.V. Bashkatova, E.I. Korotkova, Y.A. Karbainov, A.Y. Yagovkin and A.A. Bakibaev, J. Pharm. Biomed. Anal., 37, 1143 (2005).
- A.E. Rubtsov, R.R. Makhmudov, N.V. Kovylyaeva, N.I. Prosyanik, A.V. Bobrov and V.V. Zalesov, Pharm. Chem. J., 36, 608 (2002).
- D. Burdulene, A. Palaima, Z. Stumbryavichyute and Z. Talaikite, Pharm. Chem. J., 33, 191 (1999).
- A.N. Evstropov, V.E. Yavorovskaya, E.S. Vorob’ev, Z.P. Khudonogova, L.N. Gritsenko, E.V. Shmidt, S.G. Medvedeva, V.D. Filimonov, T.P. Prishchep and A.S. Saratikov, Pharm. Chem. J., 26, 426 (1992).
- G.H. Sayed, S.A. Shiba, A. Radwan, S.M. Mohamed and M. Khalil, Chin. J. Chem., 10, 475 (1992).
- J. Am. Coll. Toxicol., 11, 475 (1992).
- M. Verleye, I. Heulard and J.-M. Gillardin, Pharmacol. Res., 41, 539 (2000).
- K. Saraswathi, N.V.S. Naidu, K.M. Kumari and K.P. Padmaja, Chem. Environ. Res., 8, 271 (1999).
- L. Singh, A. Sharma and S.K. Sindhu, Asian J. Chem., 11, 1445 (1999).
- Y. Zhang, Y. Li, H. Tao and L. Zhu, Acta Crystallogr. Sect. E Struct. Rep. Online, 58, 24 (2002).
- A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, ELBS, London (1961).
- E. Kurz, G. Kober and M. Berl, Anal. Chem., 30, 1958 (1983).
- O.N. Irobi, M. Moo-Young and W.A. Anderson, Int. J. Pharm., 34, 87 (1996).
- N. Raman, L. Mitu, A. Sakthivel and M.S.S. Pandi, J. Iran. Chem. Soc., 6, 738 (2009).
- Y.Z. Cai, Q. Luo, M. Sun and H. Corke, Life Sci., 74, 2157 (2004).
- K.E. Heim, A.R. Tagliaferro and D.J. Bobilya, J. Nutr. Biochem., 13, 572 (2002).
- G. Cohen and H. Eisenberg, Biopolymers, 8, 45 (1969).
- W.J. Geary, Coord. Chem. Rev., 7, 81 (1971).
- S. Joseph and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 28, 423 (1998).
- M.T.H. Tarafder, N. Saravanan, K.A. Crouse and A.M. Ali, Transition Met. Chem., 26, 613 (2001).
- K.C. Raju, N.T. Madhu and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 32, 1115 (2002).
- K.P. Deepa and K.K. Aravindakshan, Synth. React. Inorg. Met.-Org. Chem., 30, 1601 (2000).
- M. Salehi, F. Rahimifar, M. Kubicki and A. Asadi, Inorg. Chim. Acta, 443, 28 (2016).
- R.C. Maurya, D.D. Mishra, P.K. Trivedi and A. Gupta, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 24, 17 (1994).
- K. Das, T.N. Mandal, S. Roy, S. Gupta, A.K. Barik, P. Mitra, A.L. Rheingold and S.K. Kar, Polyhedron, 29, 2892 (2010).
- N.T. Madhu and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 30, 1561 (2000).
- K.Z. Ismail, Transition Met. Chem., 25, 522 (2000).
- P.M. Vimal Kumar and P.K. Radhakrishnan, Polyhedron, 29, 2335 (2010).
- A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, edn 2 (1984).
- M. del Carmen Fernández-Fernández, R.B. de la Calle, A. Macías, L.V. Matarranz and P. Pérez-Lourido, Polyhedron, 27, 2301 (2008).
- A. Sousa-Pedrares, N. Camiña, J. Romero, M.L. Durán, J.A. García- Vázquez and A. Sousa, Polyhedron, 27, 3391 (2008).
- M. Amirnasr, A.H. Mahmoudkhani, A. Gorji, S. Dehghanpour and H.R. Bijanzadeh, Polyhedron, 21, 2733 (2002).
- S. Dehghanpour and A. Mahmoudi, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 37, 35 (2007).
- M. Tuncel and S. Serin, Transition Met. Chem., 31, 805 (2006).
- S. Mathew, C.G.R. Nair and K.N. Ninan, Thermochim. Acta, 144, 33 (1989).
- M.E. Brown, Introduction to Thermal Analysis-Techniques and Applications, Chapman and Hall Ltd., New York (1988).
- M. Padmaja, J. Pragathi and C.G. Kumari, J. Chem. Pharm. Res., 3, 602 (2001).
- M. Tyagi, S. Chandra and P. Tyagi, Spectrochim. Acta, 117A, 1 (2014).
- S. Chandra and A. Kumar, Spectrochim. Acta, 68A, 1410 (2007).
- N. Raman and A. Selvan, J. Mol. Struct., 985, 173 (2011).
- M. Shebl, Spectrochim. Acta, 117A, 127 (2014).
- F. Gao, H. Chao, F. Zhou, Y.-X. Yuan, B. Peng and L.N. Ji, J. Inorg. Biochem., 100, 1487 (2006).
- J.K. Barton, A.T. Danishefsky and J.M. Goldberg, J. Am. Chem. Soc., 106, 2172 (1984).
- V. Uma, M. Kanthimathi, T. Weyhermuller and B.U. Nair, J. Inorg. Biochem., 99, 2299 (2005).
- S. Anbu and M. Kandaswamy, Polyhedron, 30, 123 (2011).
- N. Mudasir, N. Yoshioka and H. Inoue, J. Inorg. Biochem., 77, 239 (1999).
- S.O. Bahaffi, A.A. Abdel Aziz and M.M. El-Naggar, J. Mol. Struct., 1020, 188 (2012).
- M. Lee, A.L. Rhodes, M.D. Wyatt, S. Forrow and A. Hartley, Biochemistry, 32, 4237 (1993).
- J.R. Lakowicz and G. Weber, Biochemistry, 12, 4161 (1973).
- S. Satyanarayana, J.C. Dabrowiak and J.B. Chaires, Biochemistry, 31, 9319 (1993).
References
R.C. Maurya, A. Pandey, J. Chaurasia and H. Martin, J. Mol. Struct., 798, 89 (2006).
M. Hasani and A. Rezaei, Spectrochim. Acta, 65A, 1093 (2006).
G. Turan-Zitouni, M. Sivaci, F.S. Kilic and K. Erol, Eur. J. Med. Chem., 36, 685 (2001).
N.V. Bashkatova, E.I. Korotkova, Y.A. Karbainov, A.Y. Yagovkin and A.A. Bakibaev, J. Pharm. Biomed. Anal., 37, 1143 (2005).
A.E. Rubtsov, R.R. Makhmudov, N.V. Kovylyaeva, N.I. Prosyanik, A.V. Bobrov and V.V. Zalesov, Pharm. Chem. J., 36, 608 (2002).
D. Burdulene, A. Palaima, Z. Stumbryavichyute and Z. Talaikite, Pharm. Chem. J., 33, 191 (1999).
A.N. Evstropov, V.E. Yavorovskaya, E.S. Vorob’ev, Z.P. Khudonogova, L.N. Gritsenko, E.V. Shmidt, S.G. Medvedeva, V.D. Filimonov, T.P. Prishchep and A.S. Saratikov, Pharm. Chem. J., 26, 426 (1992).
G.H. Sayed, S.A. Shiba, A. Radwan, S.M. Mohamed and M. Khalil, Chin. J. Chem., 10, 475 (1992).
J. Am. Coll. Toxicol., 11, 475 (1992).
M. Verleye, I. Heulard and J.-M. Gillardin, Pharmacol. Res., 41, 539 (2000).
K. Saraswathi, N.V.S. Naidu, K.M. Kumari and K.P. Padmaja, Chem. Environ. Res., 8, 271 (1999).
L. Singh, A. Sharma and S.K. Sindhu, Asian J. Chem., 11, 1445 (1999).
Y. Zhang, Y. Li, H. Tao and L. Zhu, Acta Crystallogr. Sect. E Struct. Rep. Online, 58, 24 (2002).
A.I. Vogel, A Text Book of Quantitative Inorganic Analysis, ELBS, London (1961).
E. Kurz, G. Kober and M. Berl, Anal. Chem., 30, 1958 (1983).
O.N. Irobi, M. Moo-Young and W.A. Anderson, Int. J. Pharm., 34, 87 (1996).
N. Raman, L. Mitu, A. Sakthivel and M.S.S. Pandi, J. Iran. Chem. Soc., 6, 738 (2009).
Y.Z. Cai, Q. Luo, M. Sun and H. Corke, Life Sci., 74, 2157 (2004).
K.E. Heim, A.R. Tagliaferro and D.J. Bobilya, J. Nutr. Biochem., 13, 572 (2002).
G. Cohen and H. Eisenberg, Biopolymers, 8, 45 (1969).
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971).
S. Joseph and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 28, 423 (1998).
M.T.H. Tarafder, N. Saravanan, K.A. Crouse and A.M. Ali, Transition Met. Chem., 26, 613 (2001).
K.C. Raju, N.T. Madhu and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Chem., 32, 1115 (2002).
K.P. Deepa and K.K. Aravindakshan, Synth. React. Inorg. Met.-Org. Chem., 30, 1601 (2000).
M. Salehi, F. Rahimifar, M. Kubicki and A. Asadi, Inorg. Chim. Acta, 443, 28 (2016).
R.C. Maurya, D.D. Mishra, P.K. Trivedi and A. Gupta, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 24, 17 (1994).
K. Das, T.N. Mandal, S. Roy, S. Gupta, A.K. Barik, P. Mitra, A.L. Rheingold and S.K. Kar, Polyhedron, 29, 2892 (2010).
N.T. Madhu and P.K. Radhakrishnan, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 30, 1561 (2000).
K.Z. Ismail, Transition Met. Chem., 25, 522 (2000).
P.M. Vimal Kumar and P.K. Radhakrishnan, Polyhedron, 29, 2335 (2010).
A.B.P. Lever, Inorganic Electronic Spectroscopy, Elsevier, Amsterdam, edn 2 (1984).
M. del Carmen Fernández-Fernández, R.B. de la Calle, A. Macías, L.V. Matarranz and P. Pérez-Lourido, Polyhedron, 27, 2301 (2008).
A. Sousa-Pedrares, N. Camiña, J. Romero, M.L. Durán, J.A. García- Vázquez and A. Sousa, Polyhedron, 27, 3391 (2008).
M. Amirnasr, A.H. Mahmoudkhani, A. Gorji, S. Dehghanpour and H.R. Bijanzadeh, Polyhedron, 21, 2733 (2002).
S. Dehghanpour and A. Mahmoudi, Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 37, 35 (2007).
M. Tuncel and S. Serin, Transition Met. Chem., 31, 805 (2006).
S. Mathew, C.G.R. Nair and K.N. Ninan, Thermochim. Acta, 144, 33 (1989).
M.E. Brown, Introduction to Thermal Analysis-Techniques and Applications, Chapman and Hall Ltd., New York (1988).
M. Padmaja, J. Pragathi and C.G. Kumari, J. Chem. Pharm. Res., 3, 602 (2001).
M. Tyagi, S. Chandra and P. Tyagi, Spectrochim. Acta, 117A, 1 (2014).
S. Chandra and A. Kumar, Spectrochim. Acta, 68A, 1410 (2007).
N. Raman and A. Selvan, J. Mol. Struct., 985, 173 (2011).
M. Shebl, Spectrochim. Acta, 117A, 127 (2014).
F. Gao, H. Chao, F. Zhou, Y.-X. Yuan, B. Peng and L.N. Ji, J. Inorg. Biochem., 100, 1487 (2006).
J.K. Barton, A.T. Danishefsky and J.M. Goldberg, J. Am. Chem. Soc., 106, 2172 (1984).
V. Uma, M. Kanthimathi, T. Weyhermuller and B.U. Nair, J. Inorg. Biochem., 99, 2299 (2005).
S. Anbu and M. Kandaswamy, Polyhedron, 30, 123 (2011).
N. Mudasir, N. Yoshioka and H. Inoue, J. Inorg. Biochem., 77, 239 (1999).
S.O. Bahaffi, A.A. Abdel Aziz and M.M. El-Naggar, J. Mol. Struct., 1020, 188 (2012).
M. Lee, A.L. Rhodes, M.D. Wyatt, S. Forrow and A. Hartley, Biochemistry, 32, 4237 (1993).
J.R. Lakowicz and G. Weber, Biochemistry, 12, 4161 (1973).
S. Satyanarayana, J.C. Dabrowiak and J.B. Chaires, Biochemistry, 31, 9319 (1993).