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Please use this identifier to cite or link to this item: http://hdl.handle.net/1843/52494
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dc.creatorMaria Cecília Fernandes Diaspt_BR
dc.creatorBianca Lana de Sousapt_BR
dc.creatorMarisa Iontapt_BR
dc.creatorRóbson Ricardo Teixeirapt_BR
dc.creatorThiago Quinelato Goulartpt_BR
dc.creatorGuilherme Álvaro Ferreira da Silvapt_BR
dc.creatorEduardo Jorge Pilaupt_BR
dc.creatorMarcelo Henrique dos Santospt_BR
dc.date.accessioned2023-04-26T11:34:10Z-
dc.date.available2023-04-26T11:34:10Z-
dc.date.issued2021-03-
dc.citation.volume32pt_BR
dc.citation.issue3pt_BR
dc.citation.spage572pt_BR
dc.citation.epage587pt_BR
dc.identifier.doihttps://doi.org/10.21577/0103-5053.20200211pt_BR
dc.identifier.issn1678-4790pt_BR
dc.identifier.urihttp://hdl.handle.net/1843/52494-
dc.description.resumoBenzophenones display several biological activities, including antioxidant, anticancer, and photoprotective. Furthermore, antioxidants can minimize both ultraviolet absorption and tumor development. In the present investigation, a series of twenty-six 1,2,3-triazole-benzophenone derivatives were synthesized and had their antioxidant, anticancer, and photoprotective effects evaluated. For the compounds synthesis, 4,4’-dihydroxybenzophenone (1a) and 2,4-dihydroxybenzophenone (1b) were propargylated, affording the alkynes bis(4-(prop-2-yn-1-yloxy))benzophenone (2a) and (2-hydroxy-4-(prop-2-yn-1-yloxy))benzophenone (2b), respectively. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction between the compounds 2a/2b and several benzyl azides gave the 1,2,3-triazole-benzophenone derivatives with yields ranging from 35 to 95%. The 1,2,3-triazole-benzophenone derivatives at the concentration of 0.2 μg mL-1 (a no-cytotoxic concentration) exhibited a solar protection factor (SPF) comparable to positive control benzophonen-3 (BP-3). Concerning their antioxidant and cytotoxic effects, the derivatives from 1b showed high in vitro antioxidant effects as well as cytotoxicity against A549 (lung carcinoma), MCF-7 (breast carcinoma), and HT-144 (metastatic melanoma) cell lines, without significant cytotoxicity to a non-cancerous cell line. Derivatives 19, 20, and 24 induced cell death and cell cycle arrest at G1/S in HT-144 melanoma cells.pt_BR
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológicopt_BR
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Geraispt_BR
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superiorpt_BR
dc.description.sponsorshipFINEP - Financiadora de Estudos e Projetos, Financiadora de Estudos e Projetospt_BR
dc.languageengpt_BR
dc.publisherUniversidade Federal de Minas Geraispt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentICA - INSTITUTO DE CIÊNCIAS AGRÁRIASpt_BR
dc.publisher.initialsUFMGpt_BR
dc.relation.ispartofJournal of the Brazilian Chemical Society-
dc.rightsAcesso Abertopt_BR
dc.subjectBenzophenonept_BR
dc.subject1,2,3-triazolept_BR
dc.subjectCuAAC reactionpt_BR
dc.subjectantioxidantpt_BR
dc.subjectphotoprotectivept_BR
dc.subjectcytotoxicitypt_BR
dc.subject.otherBioquímicapt_BR
dc.subject.otherFotoquímica orgânicapt_BR
dc.subject.otherSíntese orgânicapt_BR
dc.subject.otherAntioxidantespt_BR
dc.subject.otherMelanomapt_BR
dc.titleSynthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cellspt_BR
dc.typeArtigo de Periódicopt_BR
dc.url.externahttps://www.scielo.br/j/jbchs/a/kRdTFjZzWW94z6MQvKgSVkJ/abstract/?lang=enpt_BR
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