It takes two to tango, part II: synthesis of A-ring functionalised quinones containing two redox-active centres with antitumour activities

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dc.creatorJoyce Oliveira
dc.creatorRafaela Ferreira
dc.creatorMaria Helena de Araujo
dc.creatorClaus Jacob
dc.creatorEufrânio da Silva Júnior
dc.creatorRenato de Carvalho
dc.creatorHugo Sampaio
dc.creatorJoão Honorato
dc.creatorJavier Ellena
dc.creatorFelipe Martins
dc.creatorJoão Pereira
dc.creatorPedro Costa
dc.creatorClaudia Pessoa
dc.date.accessioned2025-01-24T21:54:05Z
dc.date.accessioned2025-09-09T00:32:33Z
dc.date.available2025-01-24T21:54:05Z
dc.date.issued2023-02-27
dc.format.mimetypepdf
dc.identifier.doihttps://doi.org/10.3390/molecules28052222
dc.identifier.issn1420-3049
dc.identifier.urihttps://hdl.handle.net/1843/79484
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofMolecules
dc.rightsAcesso Aberto
dc.subjectCélulas cancerosas
dc.subjectCâncer
dc.subjectTratamento
dc.subjectPesquisa imunológica
dc.subject.otherClick chemistry
dc.subject.otherTriazoles
dc.subject.otherQuinones
dc.subject.otherRedox centres
dc.subject.otherAnticancer activity
dc.titleIt takes two to tango, part II: synthesis of A-ring functionalised quinones containing two redox-active centres with antitumour activities
dc.typeArtigo de periódico
local.citation.epage24
local.citation.issue5
local.citation.spage1
local.citation.volume28
local.description.resumoIn 2021, our research group published the prominent anticancer activity achieved through the successful combination of two redox centres (ortho-quinone/para-quinone or quinone/selenium-containing triazole) through a copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction. The combination of two naphthoquinoidal substrates towards a synergetic product was indicated, but not fully explored. Herein, we report the synthesis of 15 new quinone-based derivatives prepared from click chemistry reactions and their subsequent evaluation against nine cancer cell lines and the murine fibroblast line L929. Our strategy was based on the modification of the A-ring of para-naphthoquinones and subsequent conjugation with different ortho-quinoidal moieties. As anticipated, our study identified several compounds with IC50 values below 0.5 µM in tumour cell lines. Some of the compounds described here also exhibited an excellent selectivity index and low cytotoxicity on L929, the control cell line. The antitumour evaluation of the compounds separately and in their conjugated form proved that the activity is strongly enhanced in the derivatives containing two redox centres. Thus, our study confirms the efficiency of using A-ring functionalized para-quinones coupled with ortho-quinones to obtain a diverse range of two redox centre compounds with potential applications against cancer cell lines. Here as well, it literally takes two for an efficient tango!
local.identifier.orcidhttps://orcid.org/0000-0003-3324-0601
local.identifier.orcidhttps://orcid.org/0000-0002-6288-7220
local.identifier.orcidhttps://orcid.org/0000-0003-1281-5453
local.identifier.orcidhttps://orcid.org/0000-0002-1127-6083
local.identifier.orcidhttps://orcid.org/0000-0002-0676-3098
local.publisher.countryBrasil
local.publisher.departmentICB - DEPARTAMENTO DE BIOQUÍMICA E IMUNOLOGIA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.mdpi.com/1420-3049/28/5/2222

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