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Type: Artigo
Title: New Spiro-acridines: Dna Interaction, Antiproliferative Activity And Inhibition Of Human Dna Topoisomerases
Author: Vitalino de Almeida
Sinara Monica; Lafayett
Elizabeth Almeida; Silva
Willams Leal; Serafim
Vanessa de Lima; Menezes
Thais Meira; Neves
Jorge Luiz; Tasca Gois Ruiz
Ana Lucia; de Carvalho
Joao Ernesto; de Moura
Ricardo Olimpio; Carneiro Beltrao
Eduardo Isidoro; de Carvalho Junior
Luiz Bezerra; Alves de Lima
Maria do Carmo
Abstract: Two new spiro-acridines were synthesized by introducing cyano-N-acylhydrazone between the acridine and phenyl rings followed by spontaneous cyclization. The final compounds (E)-1'-(benzylideneamino)-5'-oxo-1',5'-dihydro-10H-spiro[acridine-9,2'-pyrrole]-4'-carbonitrile (AMTAC-01) and (E)-1'-((4-methoxybenzylidene)amino)-5'-oxo-1',5'-dihydro-10H-spiro[acridine-9,2'-pyrrole]-4'-carbonitrile (AMTAC-02) were evaluated for their interactions with calf thymus DNA, antiproliferative and human topoisomerase I and II alpha inhibitory activities. Both compounds presented ability to bind DNA. The binding constant determined by UV-vis spectroscopy was found to be 10(4)M(-1). Antiproliferative assay demonstrated that AMTAC-01 and AMTAC-02 were most active against prostate and melanoma tumor cell lines, respectively. The compound did not present Topo I inhibitory activity. However, both derivatives displayed topoisomerase IIa inhibitory activity comparable to amsacrine, and AMTAC-02 was more potent than AMTAC-01 with methoxy substituent group on phenyl ring. This study demonstrates that the new derivatives are promising molecules with topoisomerase II alpha inhibitory and antiproliferative activities. (C) 2016 Elsevier B.V. All rights reserved.
Subject: Spiro-acridine
Editor: Elsevier Science BV
Citation: International Journal Of Biological Macromolecules. Elsevier Science Bv, v. 92, p. 467 - 475, 2016.
Rights: fechado
Identifier DOI: 10.1016/j.ijbiomac.2016.07.057
Date Issue: 2016
Appears in Collections:Unicamp - Artigos e Outros Documentos

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