Studies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of schiff bases

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dc.creatorJoão Ernesto de Carvalho
dc.creatorJosué Carinhanha Caldas Santos
dc.creatorIsis Martins Figueiredo
dc.creatorRosemeire Brondi Alves
dc.creatorLuzia Valentina Modolo
dc.creatorCleiton Moreira da Silva
dc.creatorÂngelo de Fátima
dc.creatorMarina de Magalhães Silva
dc.creatorFabiano Souza Reis
dc.creatorAna Lucia Tasca Gois Ruiz
dc.date.accessioned2024-08-03T00:39:38Z
dc.date.accessioned2025-09-09T01:15:00Z
dc.date.available2024-08-03T00:39:38Z
dc.date.issued2017
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1016/j.jphotobiol.2017.05.020
dc.identifier.issn1011-1344
dc.identifier.urihttps://hdl.handle.net/1843/72500
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of Photochemistry and Photobiology B: Biology
dc.rightsAcesso Restrito
dc.subjectSchiff, Bases de
dc.subjectAgentes antineoplásicos
dc.subjectCélulas cancerosas
dc.subjectReações de radicais livres
dc.subjectAldeídos
dc.subjectAminas
dc.subjectDNA
dc.subjectCitotoxidade de mediação celular
dc.subject.otherSchiff bases
dc.subject.otherMicrowave-assisted synthesis
dc.subject.otherFree radical scavenging
dc.subject.otherAntiproliferative activityct
dc.subject.otherDNA interaction
dc.subject.otherCancer cells
dc.titleStudies on free radical scavenging, cancer cell antiproliferation, and calf thymus DNA interaction of schiff bases
dc.typeArtigo de periódico
local.citation.epage138
local.citation.spage129
local.citation.volume172
local.description.resumoThirty-nine Schiff bases were synthesized by performing microwave-assisted condensation of the corresponding aldehydes and aromatic amines. Their reactive nitrogen species (RNS) scavenging activity and inhibitory effects against cancer cell growth were then subsequently investigated. Additionally, the interaction between the calf thymus DNA (ctDNA) and selected Schiff bases was evaluated using fluorescence spectroscopy, and their binding parameters were determined. The yields of the various compounds ranged from moderate to excellent (43–99%) after only a 2-min reaction. The hydroxylated Schiff bases 2, 8, 15, 16, 18, 20, 29, 32, 34, and 37 were found to be potent scavengers of 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals with half-maximal scavenging concentration (SC50) values lower than that of the positive control, resveratrol. The presence of hydroxyl substituents on the aromatic rings also proved essential to the cytotoxicity of the compounds. The binding constants (Kb) obtained using fluorescence spectroscopy ranged from 0.37 to 3.07 × 105 L mol− 1, and were strongly influenced by the structure and hydroxylation degree. Schiff bases 3 and 8 showed promising cytotoxic activity, with half-maximal growth inhibitory (GI50) values in the same order of magnitude as those exhibited by the reference drug, doxorubicin against various cell lines. Interestingly, these compounds also showed the highest Kb, suggesting that the cytotoxic activity could be related to their interaction with the DNA of the tumor cells. The results of this study highlighted some Schiff bases as potential lead compounds for the design of new free radical scavengers and anticancer agents.
local.identifier.orcidhttps://orcid.org/0000-0002-6901-6815
local.identifier.orcidhttps://orcid.org/0000-0002-9525-5123
local.identifier.orcidhttps://orcid.org/0000-0002-1873-5342
local.identifier.orcidhttps://orcid.org/0000-0003-0546-2549
local.identifier.orcidhttps://orcid.org/0000-0002-8033-0434
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0002-1087-4639
local.identifier.orcidhttps://orcid.org/0000-0003-2256-4379
local.identifier.orcidhttps://orcid.org/0000-0002-0844-8702
local.publisher.countryBrasil
local.publisher.departmentICB - DEPARTAMENTO DE BOTÂNICA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S1011134417302233

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