5-Nitro-Thiophene-Thiosemicarbazone Derivatives Present Antitumor Activity Mediated by Apoptosis and DNA Intercalation

Author(s): Karla Mirella Roque Marques , Maria Rodrigues do Desterro , Sandrine Maria de Arruda , Luiz Nascimento de Araújo Neto , Maria do Carmo Alves de Lima , Sinara Mônica Vitalino de Almeida , Edjan Carlos Dantas da Silva , Thiago Mendonça de Aquino , Edeildo Ferreira da Silva-Júnior , João Xavier de Araújo-Júnior , Marina de M. Silva , Maria Dayanne de A. Dantas , Josué Carinhanha C. Santos , Isis M. Figueiredo , Marc-Antoine Bazin , Pascal Marchand , Teresinha Gonçalves da Silva , Francisco Jaime Bezerra Mendonça Junior* .

Journal Name: Current Topics in Medicinal Chemistry

Volume 19 , Issue 13 , 2019

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Graphical Abstract:


Abstract:

Background: Considering the need for the development of new antitumor drugs, associated with the great antitumor potential of thiophene and thiosemicarbazonic derivatives, in this work we promote molecular hybridization approach to synthesize new compounds with increased anticancer activity.

Objective: Investigate the antitumor activity and their likely mechanisms of action of a series of N-substituted 2-(5-nitro-thiophene)-thiosemicarbazone derivatives.

Methods: Methods were performed in vitro (cytotoxicity, cell cycle progression, morphological analysis, mitochondrial membrane potential evaluation and topoisomerase assay), spectroscopic (DNA interaction studies), and in silico studies (docking and molecular modelling).

Results: Most of the compounds presented significant inhibitory activity; the NCIH-292 cell line was the most resistant, and the HL-60 cell line was the most sensitive. The most promising compound was LNN-05 with IC50 values ranging from 0.5 to 1.9 µg.mL-1. The in vitro studies revealed that LNN-05 was able to depolarize (dose-dependently) the mitochondrial membrane, induceG1 phase cell cycle arrest noticeably, promote morphological cell changes associated with apoptosis in chronic human myelocytic leukaemia (K-562) cells, and presented no topoisomerase II inhibition. Spectroscopic UV-vis and molecular fluorescence studies showed that LNN compounds interact with ctDNA forming supramolecular complexes. Intercalation between nitrogenous bases was revealed through KI quenching and competitive ethidium bromide assays. Docking and Molecular Dynamics suggested that 5-nitro-thiophene-thiosemicarbazone compounds interact against the larger DNA groove, and corroborating the spectroscopic results, may assume an intercalating interaction mode.

Conclusion: Our findings highlight 5-nitro-thiophene-thiosemicarbazone derivatives, especially LNN-05, as a promising new class of compounds for further studies to provide new anticancer therapies.

Keywords: Antitumor activity, Thiophene, Thiosemicarbazone, Apoptosis, DNA Intercalation, Cancer.

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VOLUME: 19
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Year: 2019
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