Substituted 3-acyl-2-phenylamino-1,4-naphthoquinones intercalate into DNA and cause genotoxicity through the increased generation of reactive oxygen species culminating in cell death

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dc.contributor.authorFarias, Mirelle Sifroni
dc.contributor.authorPich, Claus Troeger
dc.contributor.authorKviecinski, Maicon Roberto
dc.contributor.authorFalcao Bucker, Nadia Cristina
dc.contributor.authorFelipe, Karina Bettega
dc.contributor.authorDa Silva, Fabiana Ourique
dc.contributor.authorFisher Guenther, Tania Mara
dc.contributor.authorCorreia, Joao Francisco
dc.contributor.authorRios, David
dc.contributor.authorBenites, Julio
dc.contributor.authorValderrama, Jaime A.
dc.contributor.authorBuc Calderon, Pedro
dc.contributor.authorPedrosa, Rozangela Curi
dc.date.accessioned2025-01-23T21:44:20Z
dc.date.available2025-01-23T21:44:20Z
dc.date.issued2014
dc.description.abstractNaphthoquinones interact with biological systems by generating reactive oxygen species (ROS) that can damage cancer cells. The cytotoxicity and the antitumor activity of 3-acyl-2-phenylamino-1,4-naphthoquinones (DPB1-DPB9) were evaluated in the MCF7 human breast cancer cell line and in male Ehrlich tumor-bearing Balb/c mice. DPB4 was the most cytotoxic derivative against MCF7 cells (EC50 15 mu M) and DPB6 was the least cytotoxic one (EC50 56 mu M). The 1,4-naphthoquinone derivatives were able to cause DNA damage and promote DNA fragmentation as shown by the plasmid DNA cleavage assay (FII form). In addition, 1,4-naphthoquinone derivatives possibly interacted with DNA as intercalating agents, which was demonstrated by the changes caused in the fluorescence of the DNA-ethidium bromide complexes. Cell death of MCF7 cells induced by 3-acyl-2-phenylamino-1,4-naphthoquinones was mostly due to apoptosis. The DNA fragmentation and subsequent apoptosis may be correlated to the redox potential of the 1,4-naphthoquinone derivatives that, once present in the cell nucleus, led to the increased generation of ROS. Finally, certain 1,4-naphthoquinone derivatives and particularly DPB4 significantly inhibited the growth of Ehrlich ascites tumors in mice (73%).
dc.fuente.origenWOS
dc.identifier.doi10.3892/mmr.2014.2160
dc.identifier.eissn1791-3004
dc.identifier.issn1791-2997
dc.identifier.urihttps://doi.org/10.3892/mmr.2014.2160
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/101691
dc.identifier.wosidWOS:000337764600061
dc.issue.numero1
dc.language.isoen
dc.pagina.final410
dc.pagina.inicio405
dc.revistaMolecular medicine reports
dc.rightsacceso restringido
dc.subject3-acyl-2-phenylamino-1,4-naphthoquinones
dc.subjectreactive oxygen species generation
dc.subjectDNA fragmentation
dc.subjectcytotoxicity
dc.subjectapoptosis
dc.subjectantitumor effect
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleSubstituted 3-acyl-2-phenylamino-1,4-naphthoquinones intercalate into DNA and cause genotoxicity through the increased generation of reactive oxygen species culminating in cell death
dc.typeartículo
dc.volumen10
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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