Abstract
Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) mixed-ligand complexes were synthesized using 4-[(furan-2-ylmethylene)amino]-1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one as the main ligand and 1,10-phenanthroline/2,2′-bipyridine as co-ligand(s). They were characterized by the usual analytical and spectral techniques. The data obtained reveal that the complexes adopt an octahedral geometry around the central metal ions. These complexes were found to be better antimicrobial agents than the free ligands. The DNA (CT) binding properties of the complexes were explored by UV–Vis, viscosity measurements, cyclic voltammetry, differential pulse voltammetry, and molecular docking studies. Binding constants for the above complexes were found to be on the order of 104, indicating that most of the synthesized complexes are partial intercalators. The DNA-cleavage activities of the complexes were also assessed using supercoiled pUC19 DNA and gel electrophoresis, and the results revealed that the hydroxyl radical is likely to be the reactive species responsible for the cleavage of pUC19 DNA by the synthesized complexes.
Graphical abstract
.
Similar content being viewed by others
References
Belaid S, Laandreau A, Djebbar S, Benail-Bouchara O (2008) J Inorg Biochem 102:63
Patil M, Hunoor R, Gudasi K (2010) Eur J Med Chem 45:2981
Liu YJ, Wang N, Mei WJ, Chen F, He LX, Jian LQ, Wang RJ (2007) Transition Met Chem 32:332
Vijayalakshmi R, Kanthimathi M, Subramanian V, Nair BU (2000) Biochim Biophys Acta 1475:157
Kasprzak KS (1991) Chem Res Toxicol 4:604
Raman N, Jeyamurugan R, Rajkapoor B, Mahesh V (2009) Appl Organometal Chem 23:283
Zeitsch KJ (2000) The chemistry and technology of furfural and its many by-products, 1st edn. Elsevier, Amsterdam, p 327
Stubbe J, Kozarich JW (1987) Chem Rev 87:1107
Pratviel G, Bernadou J, Meunier B (1995) Angew Chem Int Ed 34:746
Burrows CJ, Muller JG (1998) Chem Rev 98:1109
Sissi C, Mancin F, Gatos M, Palumbo M, Tecilla P, Tonellato U (2005) Inorg Chem 44:2111
Frey ST, Sun HHJ, Murthy NN, Karlin KD (1996) Inorg Chim Acta 242:329
Ranford JD, Sadler PJ, Tocher DA (1993) J Chem Soc Dalton Trans 3393
Mamedov VA, Kalinin AA, Azancheev NM, Levin YA (2003) Russ J Org Chem 39:125
Selvakumar PM, Suresh E, Subramanian PS (2007) Polyhedron 26:749
Bareefield EK, Freeman GM, Van Derveer DG (1986) Inorg Chem 25:552
Devries N, Reedijk J (1990) Inorg Chem 30:3700
Raman N, Sobha S (2012) Spectrochim Acta A 85:223
Nakamoto K (1970) Infrared spectra of inorganic and coordination compounds, 2nd edn. Wiley, New York
Lever ABP (1968) Inorganic electronic spectroscopy, 2nd edn. Elsevier, New York
Cotton FA, Wilkinson G (1988) Advanced inorganic chemistry, 5th edn. Wiley, New York
Konstantinovic SS, Radovanovic BC, Krkljes A (2007) J Therm Anal Calorim 90:525
Roy S, Mandal TN, Barik AK, Gupta S, Butcher RJ, Nethaji M, Kar SK (2008) Polyhedron 27:593
Raman N, Pothiraj K, Baskaran T (2011) J Mol Struct 1000:135
Prasad Singh V, Katiyar A (2008) Pestic Biochem Phys 92:8
Speier G, Csihony J, Whalen AM, Pierpont CG (1996) Inorg Chem 35:3519
Hathaway BJ, Bardley JN, Gillard RD (eds) (1971) Essays in chemistry. Academic, New York
Sitlani AS, Long EC, Pyle AM, Barton JK (1992) J Am Chem Soc 114:2303
Tysoe SA, Morgan RJ, Barker AD, Strekas TC (1993) J Phys Chem 97:1707
Kelly TM, Tossi AB, McConnell DJ, Oh Uigin C (1985) Nucleic Acid Res 13:6017
Pyle AM, Rehmann JP, Meshoyrer R, Kumar CV, Turro NJ, Barton JK (1989) J Am Chem Soc 111:3051
Li QG, Wang HM, Li AZ (1992) Molecular biophysical chemistry. Higher Education, Beijing (in Chinese)
Garnovskii AD, Nivorozkhin AL, Minkin VI (1993) Coord Chem Rev 126:1
Shahabadi N, Kashanian S, Darabi F (2010) Eur J Med Chem 45:4239
Chitrapriya N, Mahalingam V, Zeller M, Natarajan K (2010) Inorg Chim Acta 363:3685
Norden B, Tjerneld T (1982) Biopolymers 21:1713
Peng B, Chen X, Du KJ, Leyu B, Chao H, Nianji L (2009) Spectrochim Acta A 74:896
Ramakrishnan S, Palaniandavar M (2005) J Chem Sci 117:179
Tweedy BG (1964) Phytopathology 55:910
Raman N, Sakthivel A, Rajasekaran K (2009) J Coord Chem 62:1661
Sigel H (1973) Metal ions in biological systems, vol 2. Marcel Dekker, New York
Senthil Kumar R, Sasikala K, Arunachalam S (2008) Inorg Biochem 102:234
Panchal PK, Parekh HM, Pansuriya PB (2006) J Enz Inhib Med Chem 21:203
Perrin DD, Armarego WLF, Perrin DR (1980) Purification of laboratory chemicals. Pergamon, Oxford
Angllici RJ (1969) Synthesis and techniques in inorganic chemistry. WB Saunders, Philadelphia
Vogel AI (1989) Text book of quantitative chemical analysis, 5th edn. Longman, London
Ismail KZ, El-Dissouky A, Sheehada AZ (1997) Polyhedron 17:2909
Wolfe A, Shimer GH, Meehan T (1987) Biochemistry 26:6392
Reichmann ME, Rice SA, Thomas CA, Doty P (1954) J Am Chem Soc 76:3047
Tan LF, Liu XH, Chao H, Ji LN (2007) J Inorg Biochem 101:56
Charies JB, Dattagupta N, Cromers DM (1982) Biochemistry 21:3933
Satyanarayanan S, Davorusak JC, Charies JB (1983) Biochemistry 32:2573
Boyd RF (1988) General microbiology, 2nd int edn. Times Mirror/Mosby College, St. Louis
Kannan N (1996) Laboratory manual in general microbiology, 1st edn. Palani Paramount, Palani
Acknowledgments
The authors express their sincere thanks to the Managing Board, the Principal, and the Head of the Department of Chemistry for providing research facilities and moral support. AS thanks the University Grants Commission (UGC) in Hyderabad for financial support.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Sakthivel, A., Raman, N. & Mitu, L. DNA interaction studies of pyrazolone- and diimine-incorporated Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes: synthesis, spectroscopic characterization, and antimicrobial study. Monatsh Chem 144, 605–620 (2013). https://doi.org/10.1007/s00706-012-0857-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-012-0857-7