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

Novel Heterocyclic Fused Pyarzolequinolines: An Efficient Synthesis, DNA Binding Interaction and Antimicrobial Activity | Chapter 1 | Novel Aspects on Chemistry and Biochemistry Vol. 6

This unit reported a rapid and adept method for the combination of novel fused- pyarzolequinolines derivatives in tart acid aqueous television with quantitative yield. The combined compounds (2a) and (4a) interact with CT-DNA. Fused tetracyclic plans containing a quinoline core represent an important class of heterocyclic bioactive unrefined products and pharmaceuticals by way of their significant and wide-range biological properties. Several of these compounds have existed obtained accompanying diverse pharmacological and biological ventures, such as antiplasmodial, antifungal, antibacterial, powerful antiparasitic, antiproliferative, anti-swelling and anti-inflammatory exercises.In the present division, the synthesis of 3-(5-phenyl-4,5-dihydro-1H-pyrazol-3-yl)quinolin-2-ol (2a)/(3a) and 3-(2-hydroxyquinolin-3-yl)-5-phenyl-4,5-dihydro-1H-pyrazole-1 carbothioamide(4a) were prepared in accordance with Claisen-Schmidt condensation, via abridgment of 2- hydroxyquinoline-3-carbaldehyde with ketones. All basic solvents used for the combining were of analytical grade. The TLC was acted on Baker-Flex silica gel 1B-F (1.55) plates using ethyl acetate and oil ether. Then finally, a, Q-unsaturated ketone (3) reacts accompanying hydrazine hydrate, phenylhydrazine and thiosemicarbazide obtained from the matching substituted fused-pyarzolequinolines. The proposed constructions of the products and characterizations combined compounds of the reactions were assured established the spectral data and synthetic evidences. Viscosity experiment is considered all at once of the least ambiguous and ultimate critical tests of a binding manner in solution in the absence of crystallographic building data. The newly combined compounds were characterized by basic analysis, IR, 1H-NMR, and Mass spectral dossier. The interaction of the chosen projectiles for weaponry with shin thymus-DNA (CT-DNA) was investigated exploiting electronic ranges, viscosity tests, and thermal denaturation studies. The absorbance range experienced bathochromic and hypochromic alterations upon binding to CT-DNA. The binding constant (Kb) present value of 5.3x104 M-1 for (2a) and 6.5x105 M-1 for (4a). The stickiness measurements indicated that the viscosities of sonicated bar like DNA fragments were increased. The recently synthesized compounds tested for antimicrobial venture and, from protocol shows sulfur containing carbothioamide compounds (4a) shown significant inhibitory project and also bind more strongly accompanying calf organ meat-DNA compared to (2a).

Author(s) Details:

Devappa S. Lamani,
Department of Chemistry, Prof. CNR Rao Research Center, Basaveshwar Science College, Bagalkot Karnataka, India.

Please see the link here: https://stm.bookpi.org/NACB-V6/article/view/11713