A series of novel C3-linked β -carboline pyridine (BCP) derivatives have
been synthesized via modified Khronke reaction and studied for their DNA-binding
affinities. Among all the derivatives, compound 12f has shown significant enhancement
in the DNA-binding affinity (ΔTm: 6.3 oC and 6.5 oC at 0 h and 18 h incubation)
in comparison to the standard Doxorubicin (ΔTm: 2.4 oC and 2.6 oC at 0 h and 18 h
incubation). This result suggested a strong intercalation with DNA double helix. Moreover, molecular modeling studies
also showed that the planar β-carboline ring establishes π–π interactions with DNA base pairs and these interactions are
further extended due to the presence of pyridine ring. The DNA intercalation has also been investigated for these compounds
by molecular docking and the results are in agreement with thermal denaturation data.
Keywords: β-Carbolines, DNA-binding affinity, khronke reaction, DNA intercalation, molecular modeling, terpyridine.
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