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A novel polycyclic cage-like heterocyclic hybrid comprising several privileged structures such as pyrroloisoquinoline, 4-pyridinone and a α,β -unsaturated ketone moiety has been synthesized in good yield employing a microwave mediated [3 + 2]-cycloaddition/annulation strategy in 1-butyl-3-methylimidazolium bromide ([bmim]Br). The compound thus synthesized was analyzed for in vitro anticancer activity employing MCF-7, Jurkat, HCT 116 and NCI-H460 cell lines. The effect of polycyclic cage-like heterocyclic hybrid on cells viability was analyzed by MTT assay and its DNA damage efficiency was confirmed by several examinations like apoptosis study, cell cycle analysis, caspase-3 expression analysis and TUNEL assay. Mitochondrial membrane potential was determined by JC-1 staining. The polycyclic cage-like heterocyclic hybrid bearing diverse functionalities played a major role in DNA damage of cancerous cells and in consequence inhibited the DNA cells proliferation.