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Synthesis and evaluation of the cytotoxic activity of Furanaphthoquinones tethered to 1H-1,2,3-triazoles in Caco-2, Calu-3, MDA-MB231 cells

2018; Elsevier BV; Volume: 156; Linguagem: Inglês

10.1016/j.ejmech.2018.07.018

1768-3254

Dora C. S. Costa, Gabriella Silva de Almeida, Vitor Won‐Held Rabelo, Lúcio Mendes Cabral, P.C Sathler, Paula Alvarez Abreu, Vı́tor F. Ferreira, Luiz Cláudio Rodrigues Pereira da Silva, Fernando de Carvalho da Silva,

Synthesis and biological activity

Naphthoquinones and 1,2,3-triazoles are structural pharmacophore that is known to impart several cancer cells. This work shows a synthetic methodology to obtain hybrid molecules involving naphthoquinone and triazol scaffold as multiple ligands. A simple and efficient synthetic route was used to prepare a series of sixteen compounds being eight 2-(1-aryl-1H-1,2,3-triazol-4-yl)-2,3-dihydronaphtho[1,2 b]furan-4,5-diones and eight 2-(1-aryl-1H-1,2,3-triazol-4-yl)-2,3-dihydronaphtho[2,3-b]furan-4,9-diones. These compounds were tested in MDA-MB231, Caco-2 and Calu-3 human cancer cells, and among them 7a was the most selective compound on Caco-2 cells, the most sensitized cell line in this study. In silico study suggest that the blockage of topoisomerase I and IIα may be one of the mechanisms of action responsible for the cytotoxic effect of 7a in Caco-2 cells.