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This work is licensed under a Creative Commons Attribution 4.0 International License.
Mixed Ligand Complexes with 4-Aminoantipyrine Derivatives to Combat Natural Antioxidant System: Synthesis, Characterization and Biological Studies
Corresponding Author(s) : J. Joseph
Asian Journal of Chemistry,
Vol. 27 No. 3 (2015): Vol 27 Issue 3
Abstract
Novel 4-aminoantipyrine based mixed ligand metal complexes with the Schiff bases of L1 (L1- 4-aminoantipyrine with furfuraldehyde and L2/L3/L4/L5 are and L2-2-aminophenol with salicylaldehyde, L3-2-aminophenol with cinnamaldehyde, L4-2-aminobenzothiazole with salicylaldehyde, L5-2-aminobenzothiazole with cinnamaldehyde) were synthesized. The structures of the mixed ligand complexes were established by analytical and spectral techniques. They were screened for in vitro antimicrobial activity against of bacteria and fungi by disc diffusion method. The interaction of metal complexes with calf thymus-DNA (CT-DNA) was investigated by UV-visible, cyclic voltammetry, viscosity and thermal denaturation studies. DNA interaction studies suggest that metal complex binds to calf thymus-DNA through intercalation mode. Superoxide dismutase activity of these complexes has also been studied. The free ligands and their metal complexes have been tested for in vitro antioxidant activity by the reduction of 1,1-diphenyl-2-picryl hydrazyl (DPPH). The antioxidant activities of the complexes were studied and compared with the activity of ascorbic acid. Copper(II) complex showed superior antioxidant activity than other complexes.
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- A.A. Khandar, S.A. Hosseini-Yazdi, S.A. Zarei and U.M. Rabie, Inorg. Chim. Acta, 358, 3211 (2005); doi:10.1016/j.ica.2005.04.028.
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References
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T.D. Bradshaw, M.C. Bibby, J.A. Double, I. Fichtner, P.A. Cooper, M.C. Alley, S. Donohue, S.F. Stinson, J.E. Tomaszewjski, E.A. Sausville and M.F.G. Stevens, Mol. Cancer. Ther., 1, 239 (2002).
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E. Abignente, P. De-Capariis, A. Sacchi and E. Marmole, Farmaco Sci., 38, 533 (1983).
C. Ramalingan, S. Balasubramanian, S. Kabilan and M. Vasudevan, Eur. J. Med. Chem., 39, 527 (2004); doi:10.1016/j.ejmech.2004.02.005.
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M. Ismail, Indian J. Pharm. Sci., 45, 121 (1986); Chem. Abstr., 107, 175589 (1987).
P.O. Lumme and H. Knuuttila, Polyhedron, 14, 1553 (1995); doi:10.1016/0277-5387(94)00442-H.
R.A. Holley and D. Patel, Food Microbiol., 22, 273 (2005); doi:10.1016/j.fm.2004.08.006.
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J.M. Dornish, E.O. Pettersen and R. Oftebro, Cancer Res., 49, 3917 (1989).
S. Cunha, S.M. Oliveira, M.T. Rodrigues Jr., R.M. Bastos, J. Ferrari, C.M.A. de Oliveira, L. Kato, H.B. Napolitano, I. Vencato and C. Lariucci, J. Mol. Struct., 752, 32 (2005); doi:10.1016/j.molstruc.2005.05.016.
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V.C. Filho, R. Correa, Z. Vaz, J.B. Calixto, R.J. Nunes, T.R. Pinheiro, A.D. Andricopulo and R.A. Yunes, Farmaco, 53, 55 (1998); doi:10.1016/S0014-827X(97)00006-2.
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A.I. Vogel, A Textbook of Quantitative Inorganic Analysis Including Elementary Instrumental Analysis edn 4, Longman, London (1978).
M.E. Bodini, M. Angelica del Valle and S. Cáceres, Polyhedron, 16, 2903 (1997); doi:10.1016/S0277-5387(97)00062-4.
R.L. De, M. Mandal, L. Roy, J. Mukherjee and B.K.M. Ruchika, Indian J. Chem., 47A, 1480 (2008).
V.D. Bhatt and S.R. Ram, Chem. Sci. J., 63, 1 (2012).
Y. Chen, M. Wang, R.T. Rosen and C.T. Ho, J. Agric. Food Chem., 47, 2226 (1999); doi:10.1021/jf990092f.
R.G. Bhirud and T.S. Srivastava, Inorg. Chim. Acta, 179, 125 (1991); doi:10.1016/S0020-1693(00)85383-9.
W.J. Geary, Coord. Chem. Rev., 7, 81 (1971); doi:10.1016/S0010-8545(00)80009-0.
A.B.P. Lever, Inorganic Electronic Spectroscopy, edn 2, Elsevier, New York (1968).
A.B.P. Lever and E. Mantovani, Inorg. Chem., 10, 817 (1971); doi:10.1021/ic50098a031.
A.B.P. Lever, Inorganic Electronic Spectroscopy, edn 2, Elsevier, New York (1968).
G. Maki, J. Chem. Phys., 28, 651 (1958); doi:10.1063/1.1744207.
H. Temel, S. Ilhan, M. Sekerci and R. Ziyadanogullari, Spectrosc. Lett., 35, 219 (2002); doi:10.1081/SL-120003807.
B.J. Hathaway and D.E. Billing, Coord. Chem. Rev., 5, 143 (1970); doi:10.1016/S0010-8545(00)80135-6.
R.K. Ray and G.R. Kauffman, Inorg. Chim. Acta, 173, 207 (1990); doi:10.1016/S0020-1693(00)80215-7.
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J.B. Le Pecq and C. Paoletti, J. Mol. Biol., 27, 87 (1967); doi:10.1016/0022-2836(67)90353-1.
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J. SantaLucia, Proc. Natl. Acad. Sci. USA, 95, 1460 (1998); doi:10.1073/pnas.95.4.1460.
S. Arounaguiri and B.G. Maiya, Inorg. Chem., 35, 4267 (1996); doi:10.1021/ic9508684.
A. McCoubrey, H.C. Latham, P.R. Cook, A. Rodger and G. Lowe, FEBS Lett., 73, 380 (1996); doi:10.1016/0014-5793(95)01537-X.
E. Tselepi-Kalouli and N. Katsaros, J. Inorg. Biochem., 37, 271 (1989); doi:10.1016/0162-0134(89)85002-0.
J.R. Soare, T.C.P. Dinis, A.P. Cunha and L. Almeida, Free Radic. Res., 26, 469 (1997); doi:10.3109/10715769709084484.
P.D. Duh, Y.Y. Tu and G.C. Yen, Lebensm.-Wissen. Technol., 32, 269 (1999); doi:10.1006/fstl.1999.0548.
I. Gulcin, F. Topal, S.B.O. Sarikaya, E. Bursal, G. Bilsel and A.C. Goren, Rec. Nat. Prod., 5, 158 (2011).
J. Gabrielska, M. Soczynska-Kordala, J. Hladyszowski, R. Zylka, J. Miskiewicz and S. Przestalski, J. Agric. Food Chem., 54, 7735 (2006); doi:10.1021/jf060720a.
J.A. Fee, in ed.: H. Sigel, Metal Ions in Biological System, vol. 28, Marcel Dekker, New York, pp. 455-505 (1981).
S. Belaid, A. Landreau, S. Djebbar, O. Benali-Baitich, G. Bouet and J.-P. Bouchara, J. Inorg. Biochem., 102, 63 (2008); doi:10.1016/j.jinorgbio.2007.07.001.
N. Dharmaraj, P. Viswanathamurthi and K. Natarajan, Transition Met. Chem., 26, 105 (2001); doi:10.1023/A:1007132408648.
N. Farrell, Coord. Chem. Rev., 232, 1 (2002); doi:10.1016/S0010-8545(02)00100-5.
H. Arslan, N. Duran, G. Borekci, C. Koray Ozer and C. Akbay, Molecules, 14, 519 (2009); doi:10.3390/molecules14010519.