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.

Keywords

Tridentate ligand 8-Aminoquinoline 2 3 4-Trihydroxy benzaldehyde Intercalative binding Anticancer activity MTT assay Octahedral Cisplatin.

Article Details

How to Cite
Sanjeev, A., Naresh Reddy, N., Kumara Swamy, M., Rondla, R., Ranga Reddy, S., & Muralidhar Reddy, P. (2021). Synthesis, Characterization and in vitro Anticancer Studies of New Co(II), Ni(II), Cu(II) and Zn(II) Complexes of (E)-4-((Quinoline-8-ylimino)methyl)benzene-1,2,3-triol Ligand. Asian Journal of Organic & Medicinal Chemistry, 6(4), 250–258. https://doi.org/10.14233/ajomc.2021.AJOMC-P345

References

  1. S. De Flora and L.R. Ferguson, Overview of Mechanisms of Cancer Chemopreventive Agents, Mutat. Res. Fund-Mol. Mechanisms Mutagen., 591, 8 (2005); https://doi.org/10.1016/j.mrfmmm.2005.02.029
  2. N. Vasan, J. Baselga and D.M. Hyman, A View on Drug Resistance in Cancer, Nature, 575, 299 (2019); https://doi.org/10.1038/s41586-019-1730-1
  3. N.N. Reddy, S.-J. Hung, M.K. Swamy, A. Sanjeev, V.S. Rao, R. Rohini, A.K. Raju, K. Bhaskar, A. Hu and P.M. Reddy, Synthesis and Rational Design of New Appended 1,2,3-Triazole-uracil Ensembles as Promising Anti-Tumor Agents via In Silico VEGFR-2 Transferase Inhibition, Molecules, 26, 1952 (2021); https://doi.org/10.3390/molecules26071952
  4. D.A. Atwood and M.J. Harvey, Group 13 Compounds Incorporating Salen Ligands, Chem. Rev., 101, 37 (2001); https://doi.org/10.1021/cr990008v
  5. 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
  6. D. Chatterjee, E. Ember, U. Pal, S. Ghosh and R. van Eldik, Remarkably High Catalytic Activity of the RuIII(EDTA)/H2O2 System Towards Degradation of the Azo-Dye Orange II, Dalton Trans., 40, 10473 (2011); https://doi.org/10.1039/c1dt10483g
  7. P.G. Cozzi, Metal-Salen Schiff Base Complexes in Catalysis: Practical Aspects, Chem. Soc. Rev., 33, 410 (2004); https://doi.org/10.1039/B307853C
  8. A. Arbuse, M. Font, M.A. Martínez, X. Fontrodona, M.J. Prieto, V. Moreno, X. Sala and A. Llobet, DNA-Cleavage Induced by New Macrocyclic Schiff base Dinuclear Cu(I) Complexes Containing Pyridyl Pendant Arms, Inorg. Chem., 48, 11098 (2009); https://doi.org/10.1021/ic901488j
  9. M.T. Kaczmarek, R. Jastrzab, E. Holderna-Kedzia and W. Radecka-Paryzek, Self-Assembled Synthesis, Characterization and Antimicrobial Activity of Zinc(II) Salicylaldimine Complexes, Inorg. Chim. Acta, 362, 3127 (2009); https://doi.org/10.1016/j.ica.2009.02.012
  10. P. Muralidhar Reddy, Y.-P. Ho, K. Shanker, R. Rohini and V. Ravinder, Physicochemical and Biological Characterization of Novel Macrocycles Derived from o-Phthalaldehyde, Eur. J. Med. Chem., 44, 2621 (2009); https://doi.org/10.1016/j.ejmech.2008.09.035
  11. 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
  12. 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
  13. 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
  14. R. Rohini, P. Muralidhar Reddy, K. Shanker, A. Hu and V. Ravinder, Antimicrobial Study of Newly Synthesized 6-Substituted Indolo[1,2-c]-quinazolines, Eur. J. Med. Chem., 45, 1200 (2010); https://doi.org/10.1016/j.ejmech.2009.11.038
  15. R. Rohini, P.M. Reddy, K. Shanker, K. Kanthaiah, V. Ravinder and A. Hu, Synthesis of Mono, bis-2-(2-Arylideneaminophenyl)indole Azomethines as Potential Antimicrobial Agents, Arch. Pharm. Res., 34, 1077 (2011); https://doi.org/10.1007/s12272-011-0705-z
  16. 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
  17. K. Shanker, R. Rohini, K. Shravankumar, P.M. Reddy, Y. Ho and V.Ravinder, Synthesis of Tetraaza Macrocyclic PdII Complexes: Anti-bacterial and Catalytic Studies, J. Indian Chem. Soc., 86, 153 (2009).
  18. 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
  19. 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
  20. 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
  21. E.V. Puttock, J.D. Fradgley, D.S. Yufit and J.A.G. Williams, A Family of Readily Synthesised Phosphorescent Platinum(II) Complexes Based on Tridentate N^N^O-Coordinating Schiff-Base Ligands, Dalton Trans., 48, 15012 (2019); https://doi.org/10.1039/C9DT03156A
  22. 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
  23. 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
  24. 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
  25. 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
  26. 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
  27. A. Wolfe, G.H. Shimer Jr. and T. Meehan, Polycyclic Aromatic Hydrocarbons Physically Intercalate into Duplex Regions of Denatured DNA, Biochemistry, 26, 6392 (1987); https://doi.org/10.1021/bi00394a013
  28. 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
  29. 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
  30. 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
  31. 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
  32. 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
  33. 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).
  34. 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
  35. 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
  36. 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
  37. 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
  38. 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
  39. 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
  40. 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
  41. V. Uma, M. Kanthimathi, T. Weyhermuller and B.U. Nair, Oxidative DNA Cleavage Mediated by a New Copper(II) Terpyridine Complex: Crystal Structure and DNA Binding Studies, J. Inorg. Biochem., 99, 2299 (2005); https://doi.org/10.1016/j.jinorgbio.2005.08.011
  42. S. Mathur and S. Tabassum, Template Synthesis of Novel Carboxamide Dinuclear Copper(II) Complex: Spectral Characterization and Reactivity Towards Calf-Thymus DNA, Biometals, 21, 299 (2008); https://doi.org/10.1007/s10534-007-9119-2
  43. Y. Huang, Q.-S. Lu, J. Zhang, Z.-W. Zhang, Y. Zhang, S.-Y. Chen, K. Li, X.-Y. Tan, H.-H. Lin and X.-Q. Yu, DNA Cleavage by Novel Copper(II) Complex and the Role of b-Cyclodextrin in Promoting Cleavage, Bioorg. Med. Chem., 16, 1103 (2008); https://doi.org/10.1016/j.bmc.2007.10.088