ACID-BASE PROPERTIES AND AFFINITY TO DNA OF INDENOQUINOXALINECARBOXYLIC ACID DERIVATIVES
DOI:
https://doi.org/10.15421/jchemtech.v32i4.311315Keywords:
indenoquinoxaline, ionization constant, spectrophotometry, DNA intercalator, biological activityAbstract
Three amide derivatives were synthesized on the basis of 11-oxoindeno[1,2-b]quinoxaline-6-carboxylic acid and amines. The structure of the synthesized compounds was confirmed by the methods of chromatography-mass spectrometry and 1H NMR spectroscopy. Their ionization constants were determined by spectrophotometry. The intercalation of the obtained compounds into DNA was proved by two independent methods - competition with ethidium bromide and spectrophotometrically. Quantitatively, the affinity of the studied compounds to DNA was determined by the method of competition with ethidium bromide, and the association constants of this interaction were calculated. N-(2,6-dimethylpyrimidin-4-yl)-11-oxoindeno[2,1-b]quinoxaline-6-carboxamide was able to suppress the fluorescence of intercalated EB at concentrations close to the concentration of EB in the experiment, but at concentrations ten times higher all compounds significantly reduced the fluorescence intensity of EB. According to the results of the experiments, it was confirmed that the studied compounds are high-affinity DNA ligands, which allows them to be considered as APIs with antiviral and cytotoxic activity.
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