Main Article Content
Abstract
Herein, a new tridentate (NNO) Schiff base ligand, (E)-4-[(quinoline-8-ylimino)methyl]benzene-1,2,3-triol derived from the condensation of 8-aminoquinoline with 2,3,4-trihydroxy benzaldehyde is reported. The ligand was complexed with certain metal ions like Co(II) (1), Ni(II) (2), Cu(II) (3), Zn(II) (4) and were characterized by various spectroscopic and analytical techniques such as FT-IR, UV-Vis, 1H NMR, 13C NMR, ESI-Mass, ESR, elemental analysis and magnetic susceptibility. Spectral data revealed octahedral geometry for cobalt(II), nickel(II), copper(II) complexes and tetrahedral geometry for zinc(II) complex. All the metal(II) complexes along with the Schiff base ligand were screened for their anticancer activities. The CT-DNA binding studies revealed high binding propensity for metal complexes with Kb values 1.50 × 104 M-1 for 1; 3.62 × 104 M-1 for 2; 2.53 × 104 M-1 for 3 and 1.8 × 104 M-1 for 4, respectively. Anticancer studies against A549 & MCF-7 demonstrated excellent antiproliferative activity with IC50 values in the range 17.62-48.82 μM. A standard drug cisplatin was employed to compare the activity of metal complexes. The complexes exhibited remarkable antitumour activity due to their high binding ability with DNA. It is interesting to observe that the complexes did not produce any cytotoxicity towards the normal cell lines.
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Copyright (c) 2021 Asian Journal of Organic & Medicinal Chemistry
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References
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D.A. Atwood and M.J. Harvey, Group 13 Compounds Incorporating Salen Ligands, Chem. Rev., 101, 37 (2001); https://doi.org/10.1021/cr990008v
V.C. Gibson and S.K. Spitzmesser, Advances in Non-Metallocene Olefin Polymerization Catalysis, Chem. Rev., 103, 283 (2003); https://doi.org/10.1021/cr980461r
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P.G. Cozzi, Metal-Salen Schiff Base Complexes in Catalysis: Practical Aspects, Chem. Soc. Rev., 33, 410 (2004); https://doi.org/10.1039/B307853C
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P.M. Reddy, A.V.S.S. Prasad and V. Ravinder, Synthesis, Spectral Characterization, Catalytic and Antibacterial Activity of Macrocyclic Cu(II) Compounds, Transition Met. Chem., 32, 507 (2007); https://doi.org/10.1007/s11243-007-0205-7
P.M. Reddy, A.V. Prasad, K. Shanker and V. Ravinder, Synthesis, Spectral Studies and Antibacterial Activity of Novel Macrocyclic Co(II) Compounds, Spectrochim. Acta A Mol. Biomol. Spectrosc., 68, 1000 (2007); https://doi.org/10.1016/j.saa.2007.03.002
P.M. Reddy, R. Rohini, E.R. Krishna, A. Hu and V. Ravinder, Synthesis, Spectral and Antibacterial Studies of Copper(II) Tetraaza Macrocyclic Complexes, Int. J. Mol. Sci., 13, 4982 (2012); https://doi.org/10.3390/ijms13044982
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K. Shanker, R. Rohini, V. Ravinder, P.M. Reddy and Y.P. Ho, Ru(II) Complexes of N4 and N2O2 Macrocyclic Schiff Base Ligands: Their Antibacterial and Antifungal Studies, Spectrochim. Acta A Mol. Biomol. Spectrosc., 73, 205 (2009); https://doi.org/10.1016/j.saa.2009.01.021
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K. Shanker, P.M. Reddy, R. Rohini, Y.-P. Ho and V. Ravinder, Encapsulation of Pd(II) by N4 and N2O2 Macrocyclic Ligands: Their Use in Catalysis and Biology, J. Coord. Chem., 62, 3040 (2009); https://doi.org/10.1080/00958970902980511
E. Ravi Krishna, P. Muralidhar Reddy, M. Sarangapani, G. Hanmanthu, B. Geeta, K. Shoba Rani and V. Ravinder, Synthesis of N4 Donor Macrocyclic Schiff Base Ligands and their Ru (II), Pd (II), Pt (II) Metal Complexes for Biological Studies and Catalytic Oxidation of Didanosine in Pharmaceuticals, Spectrochim. Acta A Mol. Biomol. Spectrosc., 97, 189 (2012); https://doi.org/10.1016/j.saa.2012.05.073
M.J. Hearn and M.H. Cynamon, Design and Synthesis of Antituberculars: Preparation and Evaluation Against Mycobacterium tuberculosis of an Isoniazid Schiff Base, J. Antimicrob. Chemother., 53, 185 (2004); https://doi.org/10.1093/jac/dkh041
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R. Sarkar, A. Hens and K.K. Rajak, Synthesis, Characterization and DFT Study of oxorhenium(V) Complexes Incorporating Quinoline Based Tridentate Ligands, RSC Adv., 5, 15084 (2015); https://doi.org/10.1039/C4RA15135F
A. Hens, P. Mondal and K.K. Rajak, Synthesis, Structure and Spectral Properties of O,N,N Coordinating Ligands and their Neutral Zn(II) Complexes: A Combined Experimental and Theoretical Study, Dalton Trans., 42, 14905 (2013); https://doi.org/10.1039/c3dt51571k
M.E. Reichmann, S. Rice, C.A. Thomas and P. Doty, A Further Examination of the Molecular Weight and Size of Desoxypentose Nucleic Acid, J. Am. Chem. Soc., 76, 3047 (1954); https://doi.org/10.1021/ja01640a067
J. Marmur, A Procedure for the Isolation of Deoxyribonucleic Acid from Micro-Organisms, J. Mol. Biol., 3, 208 (1961); https://doi.org/10.1016/S0022-2836(61)80047-8
F. Garland, D.E. Graves, L.W. Yielding and H.C. Cheung, Comparative Studies of the Binding of Ethidium Bromide and its Photoreactive Analogs to Nucleic Acids by Fluorescence and Rapid Kinetics, Biochemistry, 19, 3221 (1980); https://doi.org/10.1021/bi00555a019
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E. Gao, Y. sun, Q. Liu and L. Duan, An Anticancer Metallobenzyl-malonate: Crystal Structure and Anticancer Activity of A Palladium Complex of 2,2?-Bipyridine and Benzylmalonate, J. Coord. Chem., 59, 1295 (2006); https://doi.org/10.1080/00958970500491093
M. Ferrari, M.C. Fornasiero and A.M. Isetta, MTT Colorimetric Assay for Testing Macrophage Cytotoxic Activity in vitro, J. Immunol. Methods, 131, 165 (1990); https://doi.org/10.1016/0022-1759(90)90187-Z
N.A. Rey, A. Neves, P.P. Silva, F.C. Paula, J.N. Silveira, F.V. Botelho, L.Q. Vieira, C.T. Pich, H. Terenzi and E.C. Pereira-Maia, A Synthetic Dinuclear Copper(II) Hydrolase and its Potential as Antitumoral: Cytotoxicity, Cellular Uptake, and DNA Cleavage, J. Inorg. Biochem., 103, 1323 (2009); https://doi.org/10.1016/j.jinorgbio.2009.05.008
P.R. Reddy, K.S. Merugu and S. Battu, Molecular Docking, DNA Interaction and in vitro Anti-Cancer Studies of Square-Planar Ni(II) and Cu(II) Complexes, Chem. Data Collect., 17-18, 30 (2018); https://doi.org/10.1016/j.cdc.2018.07.007
P.M. Reddy, W.Y. Hsu, J.F. Hu and Y.P. Ho, Digestion Completeness of Microwave-Assisted and Conventional Trypsin-Catalyzed Reactions, J. Am. Soc. Mass Spectrom., 21, 421 (2010); https://doi.org/10.1016/j.jasms.2009.11.006
M. Reddy, K. Shanker, P. Rani, D.R. Rondla, C. Reddy and V. Ravinder, New cobalt(II) Tetraaza Macrocyclic Complexes: Synthesis, Spectral and Antimicrobial Studies, J. Indian Chem. Soc., 84, 971 (2007).
B. Geeta, K. Shravankumar, P.M. Reddy, E. Ravikrishna, M. Sarangapani, K.K. Reddy and V. Ravinder, Binuclear Cobalt(II), Nickel(II), Copper(II) and Palladium(II) Complexes of a New Schiff-Base as Ligand: Synthesis, Structural Characterization, and Antibacterial Activity, Spectrochim. Acta A Mol. Biomol. Spectrosc., 77, 911 (2010); https://doi.org/10.1016/j.saa.2010.08.004
G. Budige, M.R. Puchakayala, S.R. Kongara, A. Hu and R. Vadde, Synthesis, Characterization and Biological Evaluation of Mononuclear Co(II), Ni(II), Cu(II) and Pd(II) Complexes with New N2O2 Schiff Base Ligands, Chem. Pharm. Bull. (Tokyo), 59, 166 (2011); https://doi.org/10.1248/cpb.59.166
D. Arish and M.S. Nair, Synthesis of Some Schiff Base Metal Complexes Involving para-Substituted Aromatic Aldehydes and Glycylglycine: Spectral, Electrochemical, Thermal and Surface Morphology Studies, J. Mol. Struct., 983, 112 (2010); https://doi.org/10.1016/j.molstruc.2010.08.040
V.T. Kasumov and F. Köksal, Synthesis, ESR, UV-Visible and Reactivity Studies of New bis(N-Dimethoxyaniline-3,5-tBu2-Salicylaldiminato)copper(II) Complexes, Spectrochim. Acta A Mol. Biomol. Spectrosc., 98, 207 (2012); https://doi.org/10.1016/j.saa.2012.07.122
F.-J. Zhao, H.-Q. Zhao, F. Liu, Y.-T. Li, Z.-Y. Wu and C.-W. Yan, Synthesis and Crystal Structure of New Dicopper(II) Complexes with N,N¢-bis-(Dipropylenetriamine)Oxamide as Bridging Ligand: Effects of the Counterions on DNA/Protein-Binding Property and in vitro Antitumor Activity, J. Photochem. Photobiol. B, 143, 148 (2015); https://doi.org/10.1016/j.jphotobiol.2014.12.030
M. Mohamadi, S.Y. Ebrahimipour, J. Castro and M. Torkzadeh-Mahani, Synthesis, Characterization, Crystal Structure, DNA and BSA Binding, Molecular Docking and in vitro Anticancer Activities of a Mononuclear Dioxido-Uranium(VI) Complex Derived from a Tridentate ONO Aroylhydrazone, J. Photochem. Photobiol. B, 158, 219 (2016); https://doi.org/10.1016/j.jphotobiol.2016.03.001
Z. Tian, Y. Huang, Y. Zhang, L. Song, Y. Qiao, X. Xu and C. Wang, Spectroscopic and Molecular Modeling Methods to Study the Interaction Between Naphthalimide-Polyamine Conjugates and DNA, J. Photochem. Photobiol. B, 158, 1 (2016); https://doi.org/10.1016/j.jphotobiol.2016.01.017
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