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Issue 17, 2014
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Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties

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Abstract

In this work twelve benzo[k,l]xanthene lignans were synthesized by biomimetic, Mn-mediated oxidative coupling of caffeic esters and amides. These compounds, bearing different flexible pendants at position C1/C2 of the aromatic core, interact with DNA in a dual mode, as confirmed by DF-STD NMR analysis and molecular docking: the planar core acts as a base pair intercalant, whereas the flexible pendants act as minor groove binders. Their antiproliferative activity was evaluated on a panel of six tumor cell lines: HT-29, Caco-2, HCT-116 (human colon carcinoma), H226, A549 (human lung carcinoma), and SH-SY5Y (human neuroblastoma). All compounds under study, except 29, resulted in activity against one or more cell lines, and the markedly lipophilic esters 13 and 28 showed the highest activity. Compound 13 was more active than the anticancer drug 5-fluorouracil (5-FU) towards HCT-116 (colon, GI50 = 3.16 μM) and H226 (lung, GI50 = 4.33 μM) cell lines.

Graphical abstract: Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties

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Publication details

The article was received on 17 Dec 2013, accepted on 21 Feb 2014 and first published on 21 Feb 2014


Article type: Paper
DOI: 10.1039/C3OB42521E
Citation: Org. Biomol. Chem., 2014,12, 2686-2701
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    Bio-inspired benzo[k,l]xanthene lignans: synthesis, DNA-interaction and antiproliferative properties

    C. Spatafora, V. Barresi, V. M. Bhusainahalli, S. Di Micco, N. Musso, R. Riccio, G. Bifulco, D. Condorelli and C. Tringali, Org. Biomol. Chem., 2014, 12, 2686
    DOI: 10.1039/C3OB42521E

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