Evaluation of DNA Binding and Cytotoxicity of Newly Synthesised Schiff Base (Z)-4-(((2-hydroxy phenyl)amino) (phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and Its Analogues | Chapter 1|Chemistry and Biochemistry: Research Progress Vol. 7

   A new Schiff base (Z)-4-(((2-hydroxy phenyl)amino)(phenyl)methylene)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one and its analogues were synthesised by condensation of 5-methyl-2-phenyl-4-substituted pyrazolin-3-one with 2-amino phenol from hot ethanolic solution. Schiff bases appear to be an important intermediate in a number of enzymatic reactions involving the interaction of the amino group of an enzyme, usually that of a lysine residue, with a carbonyl group of the substrate. In this study, the primary Schiff base and its derivatives are characterised by FTIR, UV, H1NMR, elemental analysis and single-crystal X- ray diffraction analysis. These potential Schiff bases are subjected to DNA binding analysis against the Calf thymus DNA, and their binding constant values were calculated and compared to the standard ruthenium intercalators. The cytotoxic nature of these Schiff bases was also studied against the human breast cancer cell line MCF-7, and their IC50 values were determined. The Schiff bases synthesised (L1, L2, L3) were stable at room temperature and possessed good keeping qualities. They were soluble in chloroform, dichloromethane, ethyl acetate and insoluble in n-hexane, petroleum ether, and toluene. The compounds exhibited different tautomeric forms (Gowri et al., 2015) in the solid state: L1 as keto-imine, L2 as imine-ol, and L3 as keto-amine. From 1H NMR spectra, it was inferred that the resulting Schiff bases exist as a mixture of tautomers (II) and (III) in CDCl3 solution. Electronic spectra revealed four types of transitions, and DNA titration studies showed increasing band intensity at ~230 and ~260 nm with DNA concentration. This study contributes to a better understanding of the interaction mechanisms between Schiff bases and nucleic acids and may aid in the development of potential probes for analysing DNA structure and conformation.

 

Author(s) Details

M. Gowri
Department of Chemistry, Avinashilingam University for Women, Coimbatore – 641 043, Tamil Nadu, India.

 

Please see the book here:- https://doi.org/10.9734/bpi/cbrp/v7/5786