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Synthesis, antitumor activity in vitro and interaction with DNA of novel amino substituted benzimidazo[1, 2-a]quinolines

Over the past few years substituted benzimidazoles and their azino fused derivatives have been one of the most extensively studied classes of heterocyclic compounds due to their well known biological activities. Benzimidazole nuclei has been widely incorporated in the structure of numerous important medical and biochemical agents. Because of the structural similarity with some naturally occurring compounds such as purine, benzimidazole derivatives can easily interact with biomolecules of the living systems. Azino fused derivatives, due to their planar structure and interesting fluorescence properties, have the ability to intercalate into DNA/RNA molecules and could offer a potential application as fluorescent probes in homogeneous assays of biological systems for detection of biomolecules in biomedical diagnostic. As a part of our continuing research in the field of medicinal chemistry, novel amino substituted benzimidazo[1, 2-a]quinolines were synthesized. For the preparation of targeted compounds, besides clasicall reactions of organic chemistry, photochemical and microwave assisted synthesis were used. All compounds were characterized by 1H, 13C NMR, IR, UV/Vis and fluorimetric spectroscopy. Antitumor activity in vitro of prepared compounds was tested on breast, colon and lung carcinoma cell lines. All compounds showed mostly prominent antiproliferative effect on the tested panel cell lines with GI50 concentrations at submicromolar range. To shed more light on the mechanisms of biological action, additional experiments of interaction with DNA of most active compounds were performed.

benzimidazoles; benzimidazo[1; 2-a]quinolines; antiproliferative activity; DNA binding

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