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Synthesis, DNA Binding and Topoisomerase I Inhibition Activity of Thiazacridine and Imidazacridine Derivatives

2013; Multidisciplinary Digital Publishing Institute; Volume: 18; Issue: 12 Linguagem: Inglês

10.3390/molecules181215035

1433-1373

Elizabeth Almeida Lafayette, Sinara Vitalino de Almeida, Marina da Rocha Pitta, Eduardo Carneiro Beltrão, Teresinha Gonçalves da Silva, Ricardo Olímpio de Moura, Ivan da Rocha Pitta, Luiz de Carvalho, Maria do Carmo Alves de Lima,

Bioactive Compounds and Antitumor Agents

Thiazacridine and imidazacridine derivatives have shown promising results as tumors suppressors in some cancer cell lines. For a better understanding of the mechanism of action of these compounds, binding studies of 5-acridin-9-ylmethylidene-3-amino-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo-thiazolidin-4-one, 5-acridin-9-ylmethylidene-2-thioxo-imidazolidin-4-one and 3-acridin-9-ylmethyl-thiazolidin-2,4-dione with calf thymus DNA (ctDNA) by electronic absorption and fluorescence spectroscopy and circular dichroism spectroscopy were performed. The binding constants ranged from 1.46 × 104 to 6.01 × 104 M−1. UV-Vis, fluorescence and circular dichroism measurements indicated that the compounds interact effectively with ctDNA, both by intercalation or external binding. They demonstrated inhibitory activities to human topoisomerase I, except for 5-acridin-9-ylmethylidene-2-thioxo-1,3-thiazolidin-4-one. These results provide insight into the DNA binding mechanism of imidazacridines and thiazacridines.