Different reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analogues

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dc.creatorD´Oliveira, Giulio Demetrius Creazzo
dc.creatorCustodio, Jean Marcos Ferreira
dc.creatorMoura, Andrea Felinto
dc.creatorNapolitano, Hamilton Barbosa
dc.creatorNoda Pérez, Caridad
dc.creatorMoraes Filho, Manoel Odorico de
dc.creatorPrókai, László
dc.creatorPerjési, Pál
dc.date.accessioned2023-08-28T12:59:52Z
dc.date.available2023-08-28T12:59:52Z
dc.date.issued2019-07-01
dc.description.abstractNon-enzyme catalyzed nucleophilic addition of reduced glutathione (GSH) onto two open-chain sulfonamide chalcones and two quinolinone-chalcone hybrids were studied to investigate the relationship between tumor cell cytotoxic activities and GSH-reactivities of the compounds. The consumption of the chalcones or the quinolinone-chalcone hybrids due to conjugation with GSH was evaluated by analytical high-performance liquid chromatography, and the formed diastereomeric adducts were identified by liquid chromatography–mass spectrometry. When the reaction was conducted with the open-chain chalcones, the equilibria were shifted towards formation of the respective GSH-conjugates. On the other hand, the cyclic chalcone derivatives with the quinolinone moiety were found to equilibrate to mixtures containing predominantly the reactants despite the strong electron withdrawing group present in the B-ring of the compounds. The observed opposite behavior can be rationalized by reduced thiol-reactivity of the quinolinone-chalcone hybrids and fast decomposition of their GSH-conjugates. A combined X-ray diffraction and theoretical approach were used to explain the observed difference in the reactivities towards GSH. However, structural differences did not influence tumor cell (SF-295, PC-3 and HCT-116) cytotoxicity of the evaluated compounds. Accordingly, the altered GSH-reactivity seems to be not a determining factor in the tested tumor cell cytotoxic activity of the investigated compounds.pt_BR
dc.identifier.citationD’OLIVEIRA, Giulio D. C. et al. Different reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analogues. Medicinal Chemistry Research, [s. l.], v. 28, p. 1448-1460, 2019. DOI: 10.1007/s00044-019-02384-8. Disponível em: https://link.springer.com/article/10.1007/s00044-019-02384-8. Acesso em: 17 ago. 2023.pt_BR
dc.identifier.doi10.1007/s00044-019-02384-8
dc.identifier.issne- 1554-8120
dc.identifier.issn1054-2523
dc.identifier.urihttp://repositorio.bc.ufg.br/handle/ri/23446
dc.language.isoengpt_BR
dc.publisher.countryEstados unidospt_BR
dc.publisher.departmentInstituto de Química - IQ (RMG)pt_BR
dc.rightsAcesso Abertopt_BR
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectChalconespt_BR
dc.subjectQuinolinonept_BR
dc.subjectGlutathionept_BR
dc.subjectMichael reactionpt_BR
dc.subjectTumor cell cytotoxicitypt_BR
dc.titleDifferent reactivity to glutathione but similar tumor cell toxicity of chalcones and their quinolinone analoguespt_BR
dc.typeArtigopt_BR

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