Synthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cells

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dc.creatorMaria Cecília Fernandes Dias
dc.creatorBianca Lana de Sousa
dc.creatorMarisa Ionta
dc.creatorRóbson Ricardo Teixeira
dc.creatorThiago Quinelato Goulart
dc.creatorGuilherme Álvaro Ferreira da Silva
dc.creatorEduardo Jorge Pilau
dc.creatorMarcelo Henrique dos Santos
dc.date.accessioned2023-04-26T11:34:10Z
dc.date.accessioned2025-09-09T01:00:43Z
dc.date.available2023-04-26T11:34:10Z
dc.date.issued2021-03
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.sponsorshipFINEP - Financiadora de Estudos e Projetos, Financiadora de Estudos e Projetos
dc.identifier.doihttps://doi.org/10.21577/0103-5053.20200211
dc.identifier.issn1678-4790
dc.identifier.urihttps://hdl.handle.net/1843/52494
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectBioquímica
dc.subjectFotoquímica orgânica
dc.subjectSíntese orgânica
dc.subjectAntioxidantes
dc.subjectMelanoma
dc.subject.otherBenzophenone
dc.subject.other1,2,3-triazole
dc.subject.otherCuAAC reaction
dc.subject.otherantioxidant
dc.subject.otherphotoprotective
dc.subject.othercytotoxicity
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 cells
dc.typeArtigo de periódico
local.citation.epage587
local.citation.issue3
local.citation.spage572
local.citation.volume32
local.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.
local.publisher.countryBrasil
local.publisher.departmentICA - INSTITUTO DE CIÊNCIAS AGRÁRIAS
local.publisher.initialsUFMG
local.url.externahttps://www.scielo.br/j/jbchs/a/kRdTFjZzWW94z6MQvKgSVkJ/abstract/?lang=en

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