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Molecules 2013, 18(12), 15035-15050; doi:10.3390/molecules181215035

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

Júnior 2
Received: 22 September 2013 / Revised: 27 November 2013 / Accepted: 2 December 2013 / Published: 6 December 2013
(This article belongs to the Section Medicinal Chemistry)
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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.
Keywords: thiazacridine; imidazacridine; DNA binding; topoisomerase I inhibitor thiazacridine; imidazacridine; DNA binding; topoisomerase I inhibitor
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.


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Lafayette, E.A.; Vitalino de Almeida, S.M.; da Rocha Pitta, M.G.; Carneiro Beltrão, E.I.; Gonçalves da Silva, T.; Olímpio de Moura, R.; da Rocha Pitta, I.; de Carvalho, L.B., Júnior; do Carmo Alves de Lima, M. Synthesis, DNA Binding and Topoisomerase I Inhibition Activity of Thiazacridine and Imidazacridine Derivatives. Molecules 2013, 18, 15035-15050.

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