Abstract:
The diazo coupliling reaction of 3- amino pyridine with coumarin in water medium produces water soluble 6-[3-
pyridyl]azocoumarin. The synthesised compound has been fully charecterised by IR, NMR, and Mass spectroscopy.
The frontier molecular orbital calculations reveal that 6-[3-pyridyl]azocoumarin is more biologically and
chemically active in comparison to coumarin. The cytotoxicity evaluation confirms that 6-[3-pyridyl]azocoumarin
is more active than coumarin against human brain glioblastoma cell lines, LN-229 with IC50 value
9.09 μM (IC50 value for coumarin is 9.9 μM). The compound (I) has been synthesized by coupling of diazotized
solution of 3-aminopyridine with coumarin in an aqueous medium at ~ pH 10. The structure of the compound (I)
has been characterized using UV–vis, IR, NMR, and Mass spectral studies. Frontier molecular orbital calculations
reveal that 6-[3-pyridyl]azocoumarin (I) is more active chemically and biologically in comparison to coumarin.
IC50 value 9.09 and 9.9 μM of 6-[3-pyridyl]azocoumarin and coumarin respectively obtained in cytotoxicity
evaluation confirms the enhanced activity of the synthesized compound against human brain glioblastoma cell
lines, LN-229. The synthesized compound also shows strong binding interactions with DNA and BSA in comparison
with coumarin. The DNA binding study shows groove binding interaction of the synthesized compound
with CT-DNA. The nature of interaction, binding parameters and structural variations of BSA in the presence of
the synthesized compound and coumarin have been evaluated using several usefull spectroscopy approaches
such as UV –Vis, time resolved and stady state flurescence. The molecular docking interaction has been carried
out to justify the experimental binding interaction with DNA and BSA.
