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Original Articles

Mixed ligand N4O2 type metal(II) complexes as metallointercalators: Preliminary investigation of DNA-binding/cleavage and antimicrobial

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Pages 1117-1128 | Received 22 Jul 2016, Accepted 16 Jan 2017, Published online: 23 Mar 2017

References

  • Cozzi, P. G. Metal–Salen Schiff base complexes in catalysis: Practical aspects. Chem. Soc. Rev. 2004, 33, 410–421.
  • Saha, U.; Mukherjea, K. K. DNA binding and nuclease activity of an oxovanadium valinato-Schiff base complex. Int. J. Biol. Macromol. 2014, 66, 166–171.
  • Hussain, Z.; Yousif, E.; Ahmed, A.; Altaie, A. Synthesis and characterization of Schiff's bases of sulfamethoxazole. Org. Med. Chem. Lett. 2014, 4, 1.
  • Yilmaz, V. T.; Gocmen, E.; Icsel, C.; Cengiz, M.; Susluer, S. Y.; Buyukgungor, O. Synthesis, crystal structures, in vitro DNA binding, antibacterial and cytotoxic activities of new di- and polynuclear silver(I) saccharinate complexes with tertiary monophosphanes. J. Photochem. Photobiol. B 2014, 131, 31–42.
  • Shahabadi, N.; Kashanian, S.; Darabi, F. DNA binding and DNA cleavage studies of a water soluble cobalt(II) complex containing dinitrogen Schiff base ligand: The effect of metal on the mode of binding. Eur. J. Med. Chem. 2010, 45, 4239–4245.
  • Hartinger, C. G.; Dyson, P. Bioorganometallic chemistry—from teaching paradigms to medicinal applications. J. Chem. Soc. Rev. 2009, 38, 391–401.
  • (a)Ali, O. A. M. Palladium(II) and zinc(II) complexes of neutral [N2O2] donor Schiff bases derived from furfuraldehyde: Synthesis, characterization, fluorescence and corrosion inhibitors of ligands. Spectrochim. Acta A 2014, 132, 52–60. (b)Singh, A.; Pandey, O.; Sengupta, S. Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione. Spectrochim. Acta A 2013, 113, 393–399. (c)Issa, R. M.; Gaber, M.; Al-Wakiel, N. A.; Fathalla, S. K. Synthesis, spectral, thermal and biological studies of Mn(II), Co(II), Ni(II) and Cu(II) complexes with 1-(((5-mercapto-1H-1,2,4-triazol-3-yl)imino)-methyl)naphthalene-2-ol. Chin. J. Chem. 2012, 30, 547–556. (d)El-Wakiel, N.; El-Sayed, Y.; Gaber, M. Synthesis, characterization, and theoretical studies of Co(II) and Cu(II) complexes of 1-[(5-mercapto-[1,3,4]thiadiazol-2-ylimino)-methyl]-naphthalen-2-ol and its interaction with Cu nanoparticles. J. Mol. Struct. 2011, 1001, 1–11.
  • Li, Y.; Zhang, Z. X.; Li, K. C.; Song, W. D.; Li, Q. S. A novel 3D double helix cobalt(II) coordination polymer: Synthesis, crystal structures and third-order non-linear optical properties. Inorg. Chem. Commun. 2007, 10, 1557–1560.
  • Yildiz, M.; Karpuz, O.; Zeyrek, C. T.; Boyacioglu, B.; Dal, H.; Demir, N.; Yildirim, N.; Unver, H. Synthesis, biological activity, DNA binding and anion sensors, molecular structure and quantum chemical studies of a novel bidentate Schiff base derived from 3,5-bis(triflouromethyl)aniline and salicylaldehyde. J. Mol. Struct. 2015, 1094, 148–160.
  • Singh, A. K.; Pandey, O. P.; Sengupta, S. K. Synthesis, spectral characterization and biological activity of zinc(II) complexes with 3-substituted phenyl-4-amino-5-hydrazino-1, 2, 4-triazole Schiff bases. Spectrochim. Acta A 2012, 85, 1–6.
  • Halli, M. B.; Sumathi, R. B. Synthesis, spectroscopic, antimicrobial and DNA cleavage studies of new Co(II), Ni(II), Cu(II), Cd(II), Zn(II) and Hg(II) complexes with naphthofuran-2-carbohydrazide Schiff base. J. Mol. Struct. 2012, 1022, 130–138.
  • Kathiresan, S.; Anand, T.; Mugesh, S.; Annaraj, J. Synthesis, spectral characterization and DNA bindings of tridentate N2O donor Schiff base metal(II) complexes. J. Photochem. Photobiol B 2015, 148, 290–301.
  • (a)Tan, X. J.; Liu, H. Z.; Ye, C. Z.; Lou, J. F.; Liu, Y.; Xing, D. X.; Li, S. P.; Liu, S. L.; Song, L. Z. Synthesis, characterization and in vitro cytotoxic properties of new silver(I) complexes of two novel Schiff bases derived from thiazole and pyrazine. Polyhedron 2014, 71, 119–132. (b)Marijana, H.; Kristina, S.; Sandra, K. Synthesis, spectroscopic characterization and antiproliferative evaluation in vitro of novel Schiff bases related to benzimidazoles. Eur. J. Med. Chem. 2011, 46, 2274–2282. (c)Chhonker, Y. S.; Veenu, B.; Hasim, S. R. Synthesis and pharmacological evaluation of some new 2-phenyl benzimidazoles derivatives and their Schiff's bases. J. Chem. 2009, 6, S342–S346. (d)Sherif, O. E.; Abdel-Kader, N. S. Spectroscopic and biological activities studies of bivalent transition metal complexes of Schiff bases derived from condensation of 1,4-phenylenediamine and benzopyrone derivatives. Spectrochim. Acta A 2014, 117, 519–526.
  • Sadeek, S. A.; Refat, M. S.; Teleb, S. M. Spectroscopic studies and thermal analysis of lead(II) and tin(II) solid complexes with bi-, tri- and tetradentate Schiff bases. Bull. Chem. Soc. Ethiop. 2004, 18, 149–156.
  • Vanparia, S. F.; Patel, T. S.; Sojitra, N. A. Synthesis, characterization and antimicrobial study of novel 4-{[(8-hydroxyquinolin-5 yl)methyl]amino}benzenesulfonamide and its oxinates. Acta Chim. Slov. 2010, 57, 600–667.
  • Prachayasittikul, V.; Prachayasittikul, S.; Ruchirawat, S.; Prachayasittikul, V. 8-Hydroxyquinolines: A review of their metal chelating properties and medicinal applications. Drug Des. Dev. Ther. 2013, 7, 1157–1178.
  • Li, Y.; Yang, Z. Y.; Wang, M. F. Synthesis, characterization, DNA binding properties and antioxidant activity of Ln(III) complexes with hesperetin-4-one-(benzoyl) hydrazone. Eur. J. Med. Chem. 2009, 44, 4585–4595.
  • Arjmand, F.; Parveen, S.; Afzal, M.; Shahid, M. Synthesis, characterization, biological studies (DNA binding, cleavage, antibacterial and topoisomerase I) and molecular docking of copper(II) benzimidazole complexes. J. Photochem. Photobiol B 2012, 114, 15–26.
  • He, X. Q.; Lin, Q. Y.; Hu, R. D.; Lu, X. H. Synthesis, characterization and DNA-binding studies on La(III) and Ce(III) complexes containing ligand of N-phenyl-2-pyridinecarboxamide. Spectrochim. Acta A 2007, 68, 184–190.
  • Sathyanarayana, S.; Daborusak, J. C.; Chaires, J. B. Tris(phenanthroline)ruthenium(II) enantiomer interactions with DNA: Mode and specificity of binding. Biochemistry 1993, 32, 2573–2584.
  • Kashanian, S.; Khodaei, M.; Pakravan, P. Spectroscopic studies on the interaction of isatin with calf thymus DNA. DNA Cell. Biol. 2010, 29, 639–646.
  • Cohen, G.; Eisenberg, H. Viscosity and sedimentation study of sonicated DNA–proflavine complexes. Biopolymers 1969, 8, 45–55.
  • Ye Yu, Y.; Duo Xian, H.; Feng Liu, J.; Liang Zhao, G. Synthesis, characterization, crystal structure and antibacterial activities of transition metal(II) complexes of the Schiff base 2-[(4-methylphenylimino)methyl]-6-methoxyphenol. Molecules 2009, 14, 1747–1754.
  • Sundaravadivel, E.; Kandaswamy, M.; Varghese, B. Synthesis, characterization and electrochemical behavior of new acyclic mono and binuclear copper (II) complexes: DNA binding and cleavage studies. Polyhedron 2013, 61, 33–44.
  • Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bachmann, M. Advanced Inorganic Chemistry, 6th ed.; Wiley, New York, 2003.
  • Mishra, M.; Tiwari, K.; Singh, A. K.; Singh, V. P. Synthesis, structural and corrosion inhibition studies on Mn(II), Cu(II) and Zn(II) complexes with a Schiff base derived from 2-hydroxypropiophenone. Polyhedron 2014, 27, 57–65.
  • (a)Lever, A. B. P. Inorg. Electr. Spectr., 2nd ed.; Elsevier, New York, 1968. (b)Uma, V.; Vaidyanathan, V. G.; Nair, B. U. Synthesis, structure, and DNA binding studies of copper(II) complexes of terpyridine derivatives. Bull. Chem. Soc. Jpn. 2005, 78, 845–850.
  • Penfield, K. W.; Gewirth, A. A.; Solomon, E. I. Electronic structure and bonding of the blue copper site in plastocyanin. J. Am. Chem. Soc. 1985, 107, 4519–4529.
  • Patil, S. A.; Unki, S. N.; Kulkarni, A. D.; Naik, V. H.; Badami, P. S. Co(II), Ni(II) and Cu(II) complexes with coumarin-8-yl Schiff-bases: Spectroscopic, in vitro antimicrobial, DNA cleavage and fluorescence studies. Spectrochim. Acta A 2011, 79, 1128–1136.
  • Sameerah, I. A. -S.; Abdel-Nasser, M. A.; Alaghaz, R. A. A. Synthesis, spectroscopic characterization and electrochemical studies of Girard's T chromone complexes. J. Mol. Struct. 2016, 1111, 201–213.
  • Cotton, F. A.; Wilkinson, G. Advanced Inorganic Chemistry; Interscience Publishers, London, 1974.
  • Sivakami, M.; Natarajan, B.; Vijayachandrasekar, M.; Rajeswari, S.; Ram Kumar Pandian, S. Synthesis, DNA binding, cleavage and antimicrobial properties of novel Mannich base and its metal complexes. Int. J. Pharm. Sci. Rev. Res. 2014, 27, 336–342.
  • Chauhan, M.; Arjmand, F. Chiral and achiral macrocyclic copper(II) complexes: Synthesis, characterization, and comparative binding studies with calf-thymus DNA. Chem. Biodivers. 2006, 3, 660–676.
  • Xing, T. T.; Zhan, S. H.; Li, Y. T.; Wu, Z. Y.; Yan, C. W. Synthesis and structure of a new tetracopper(II) complex with N-benzoate-N′;-[2-(2-hydroxyethylamino)ethyl]oxamide as bridging ligand: in vitro anticancer activities and DNA- and BSA-binding studies. J. Coord. Chem. 2013, 66, 3149–3169.
  • Xie, C. Z.; Sun, M. M.; Li, S. H.; Zhang, X. T.; Qiao, X.; Ouyang, Y.; Xu, J. Y. Synthesis, characterization, DNA interaction, cytotoxicity, and apoptosis induction of a mixed-ligand copper(II) complex. J. Coord. Chem. 2013, 66, 3891–3905.
  • Wang, X. L.; Jiang, M.; Li, Y. T.; Wu, Z. Y.; Yan, C. W. Synthesis and crystal structure of a new dicopper(II) complex with N-benzoato-N′-(hydroxypropyl)oxamide as ligand: cytotoxic activities and reactivities towards DNA and BSA. J. Coord. Chem. 2013, 66, 1985–2003.
  • Friedman, A. E.; Chambron, J. C.; Sauvage, J. P.; Turro, N. J.; Barton, J. K. A molecular light switch for DNA: Ru(bpy)2(dppz)2+. J. Am. Chem. Soc. 1990, 112, 4960–4962.
  • Lepecp, J. B.; Paoletti, C. A fluorescent complex between ethidium bromide and nucleic acids: Physical-chemical characterization. J. Mol. Biol. 1967, 27, 87–106.
  • Abdel Aziz, A. A.; Elbadawy, H. A. Spectral, electrochemical, thermal, DNA binding ability, antioxidant and antibacterial studies of novel Ru(III) Schiff base complexes. Spectrochim. Acta A 2014, 124, 404–415.
  • Parveen, S.; Arjmand, F.; Ahmad, I. Enantiomeric in vitro DNA binding, pBR322 DNA cleavage and molecular docking studies of chiral l- and d-ternary copper(II) complexes of histidine and picolinic acid. J. Photochem. Photobiol B 2014, 130, 170–178.
  • Dong, J. F.; Li, L. Z.; Li, L.; Xu, T.; Wang, D. Synthesis, characterization, DNA-binding properties and DNA cleavage of a new ternary copper(II) complex with mixed-ligands of tridentate Schiff base and 1,10-phenanthroline. Chin. J. Chem. 2011, 29, 259–266.
  • Wen, J. H.; Li, C. Y.; Geng, Z. R.; Ma, X. Y.; Wang, Z. L. A potent antitumor Zn2+ tetraazamacrocycle complex targeting DNA: The fluorescent recognition, interaction and apoptosis studies. Chem. Commun. 2011, 47, 11330–11332.
  • Benial, A. M. F.; Ramakrishnan, V.; Murugesan, R. Single crystal EPR of Cu(C5H5NO)6(BF4)2: an example of admixed ground state. Spectrochim. Acta A 2000, 56, 2775–2781.
  • Boger, D. L.; Fink, B. E.; Brunette, S. R.; Tse, W. C.; Hedrick, M. P. A simple, high-resolution method for establishing DNA binding affinity and sequence selectivity. J. Am. Chem. Soc. 2001, 123, 5878–5891.
  • Li, L. Z.; Zhao, C.; Xu, T.; Ji, H. W.; Yu, Y. H.; Guo, G. Q.; Chao, H. Synthesis, crystal structure and nuclease activity of a Schiff base copper(II) complex. J. Inorg. Biochem. 2005, 99, 1076–1082.
  • Liu, C.; Wang, M.; Zhang, T.; Sun, H. DNA hydrolysis promoted by di- and multi-nuclear metal complexes. Coord. Chem. Rev. 2004, 248, 147–168.
  • Patel, D. D.; Patel, A. Simultaneous estimation of metoprolol succinate and olmesartan medoxomil in pharmaceutical dosage form by RP-HPLC. J. Pharm. Sci. Technol. 2011, 4, 905–912.
  • Singh, K.; Kumar, Y.; Puri, P.; Kumar, M.; Sharma, C. Cobalt, nickel, copper and zinc complexes with 1,3-diphenyl-1H-pyrazole-4-carboxaldehyde Schiff bases: Antimicrobial, spectroscopic, thermal and fluorescence studies. Eur. J. Med. Chem. 2012, 52, 313–321.
  • Patil, S. A.; Naik, V. H.; Kulkarni, A. D.; Badami, P. S. Spectroscopic, DNA cleavage and antimicrobial studies of Co(II), Ni(II) and Cu(II) complexes of sulfur donor Schiff bases. J. Sulfur Chem. 2010, 31, 109–121.
  • Ramesh, R.; Maheswaran, S. Synthesis, spectra, dioxygen affinity and antifungal activity of Ru(III) Schiff base complexes. J. Inorg. Biochem. 2003, 96, 457–462.

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