2-((4-Hydroxyphenylimino)methyl)-6-methoxyphenol ligand was synthesized by refluxing 2-hydroxy-3-methoxybenzaldehyde with p-aminophenol in 1:1 molar ratio. A series of transition metal complexes with the synthesized ligand OVAP, [Cr(OVAP) 2 ] (1), [Fe(OVAP) 2 ] (2), [Co(OVAP) 2 ] (3) and [Cu(OVAP) 2 ](4) is reported. Characterisation of the complexes by sophisticated analytical techniques revealed the geometry around central metal ion to be octahedral for 1, 2 and 3 complexes and complex 4 with square planar geometry. Kinetic parameters of the complexes were estimated by Coats-Redfern method, and the complexes were found to be thermally stable. DNA binding affinity of these metal complexes was explored by means of fluorescence, ultraviolet (UV)-visible and viscosity studies and the studies suggested intercalative mode. The K b values from the absorption studies are 2.98 Â 10 5 , 2.16 Â 10 5 , 4.66 Â 10 5 and 5.46 Â 10 5 M À1 and K sv values from fluorescence studies are 3.79 Â 10 4 , 2.14 Â 10 4 , 4.92 Â 10 4 and 6.47 Â 10 4 M À1 for 1, 2, 3 and 4 complexes, respectively. Nuclease studies in the presence of H 2 O 2 were performed using pUC19 supercoiled DNA. Docking studies were done using human DNA topoisomerase-I (DNA topoI) receptor protein. Biological studies revealed higher activity for complexes than the ligand, and in vitro antitumour studies showed that complexes 3 and 4 possess potential inhibitory efficiency with an IC 50 of 42.32 ± 0.5 and 38.12 ± 1.2 μg/ml correspondingly.
Funding information DST-FIST Program of India Schiff base ligand named 2-((E)-(2-fluorophenylimino)methyl)phenol (HL) was prepared by the condensation of 2-hydroxybenzaldehyde and 2-fluorobenzamine in 1:1 molar ratio. The coordination behaviour of a series of transition metal ions with the synthesized HL ligand, [Cr(HL) 2 ] (1), [Fe (HL) 2 ] (2), [Co(HL) 2 ] (3) and [Cu(HL) 2 ] (4) is reported. The structure and bonding of the metal complexes have been deduced by analytical and spectral studies. Based on the above studies, the metal centres were found to be octahedral for all the complexes. The activation thermodynamic properties were calculated using the Coats-Redfern method. Thermal decomposition processes of complexes 1, 2, 3 and 4 are non-spontaneous; that is, the complexes are thermally stable. The positive value of Gibbs free energy of decomposition (ΔG*) for all the complexes is non-spontaneous processes. DNA binding properties of these metal complexes, investigated using UV-visible absorption, fluorescence and viscosity measurement studies, imply that the complexes bind to DNA by intercalation. The intrinsic binding constant K b from the electronic absorption studies are 3.12 × 10 4 M −1 , 1.86 × 10 4 M −1 , 3.96 × 10 4 M −1 and 5.89 × 10 4 M −1 , and the Stern-Volmer quenching constant K sv values from fluorescence studies are 2.29 × 10 4 M −1 , 1.92 × 10 4 M −1 , 5.62 × 10 4 M −1 and 8.91 × 10 4 M −1 , for the complexes 1, 2, 3 and 4, respectively. DNA photo cleavage activities of these complexes were studied with supercoiled pUC19 DNA, in the presence of H 2 O 2. GOLD 3.1 program was used to evaluate binding affinities of complexes with human DNA topoisomerase I protein. in vitro cytotoxic and antimicrobial studies revealed higher activity of metal complexes, compared with the ligand.
The ligand [2‐((2‐fluorophenylimino)methyl)‐6‐methoxyphenol] and its metal complexes [Cr(HL)2] (1), [Fe(HL)2] (2), [Co(HL)2] (3) and [Cu(HL)2] (4) are synthesized. Characterization of the complexes by sophisticated analytical techniques revealed the geometry around central metal ion to be octahedral for 1, 2 and 3 complexes and complex 4 with square planar geometry. Kinetic parameters of the complexes were estimated by the Coats–Redfern method, and the complexes were found to be thermally stable. DNA binding affinity of these metal complexes was explored by means of fluorescence, UV–visible and viscosity studies, and the studies suggested intercalative mode. Kb and KSV values were determined from the absorption and fluorescence studies for the synthesized complexes. Nuclease studies in the presence of H2O2 were performed using pUC19 supercoiled DNA. Docking studies were done using human DNA topoisomerase‐I (DNA topo I) receptor protein. Biological studies revealed higher activity for complexes than the ligand, and in vitro antitumour studies showed that complexes 3 and 4 possess potential inhibitory efficiency with an IC50 of 48.79 ± 0.7 and 39.74 ± 1.6 μg/ml, respectively. Molecular docking studies were carried out using Argus labs, and geometry optimization is performed. Molecular orbital calculations of the ligand and complexes are computed using the reasonably accurate parametric model PM3 method 16–19.
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