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
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da UFMG |
| Texto Completo: | https://doi.org/10.21577/0103-5053.20200211 http://hdl.handle.net/1843/52494 |
Resumo: | CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
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2023-04-26T11:34:10Z2023-04-26T11:34:10Z2021-03323572587https://doi.org/10.21577/0103-5053.202002111678-4790http://hdl.handle.net/1843/52494CNPq - Conselho Nacional de Desenvolvimento Científico e TecnológicoFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas GeraisCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível SuperiorFINEP - Financiadora de Estudos e Projetos, Financiadora de Estudos e ProjetosBenzophenones 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.engUniversidade Federal de Minas GeraisUFMGBrasilICA - INSTITUTO DE CIÊNCIAS AGRÁRIASJournal of the Brazilian Chemical SocietyBioquímicaFotoquímica orgânicaSíntese orgânicaAntioxidantesMelanomaBenzophenone1,2,3-triazoleCuAAC reactionantioxidantphotoprotectivecytotoxicitySynthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cellsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttps://www.scielo.br/j/jbchs/a/kRdTFjZzWW94z6MQvKgSVkJ/abstract/?lang=enMaria Cecília Fernandes DiasBianca Lana de SousaMarisa IontaRóbson Ricardo TeixeiraThiago Quinelato GoulartGuilherme Álvaro Ferreira da SilvaEduardo Jorge PilauMarcelo Henrique dos Santosinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFMGinstname:Universidade Federal de Minas Gerais (UFMG)instacron:UFMGLICENSELicense.txtLicense.txttext/plain; charset=utf-82042https://repositorio.ufmg.br/bitstream/1843/52494/1/License.txtfa505098d172de0bc8864fc1287ffe22MD51ORIGINALSynthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on ht-144 melanoma cells.pdfSynthesis of 1,2,3-triazole benzophenone derivatives and evaluation of in vitro sun protection, antioxidant properties, and antiproliferative activity on ht-144 melanoma cells.pdfapplication/pdf3052462https://repositorio.ufmg.br/bitstream/1843/52494/2/Synthesis%20of%201%2c2%2c3-triazole%20benzophenone%20derivatives%20and%20evaluation%20of%20in%20vitro%20sun%20protection%2c%20antioxidant%20properties%2c%20and%20antiproliferative%20activity%20on%20ht-144%20melanoma%20cells.pdfa13ef95fca1815b0978527233103c41aMD521843/524942023-04-26 16:54:28.946oai:repositorio.ufmg.br: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Repositório de PublicaçõesPUBhttps://repositorio.ufmg.br/oaiopendoar:2023-04-26T19:54:28Repositório Institucional da UFMG - Universidade Federal de Minas Gerais (UFMG)false |
| dc.title.pt_BR.fl_str_mv |
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 |
| title |
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 |
| spellingShingle |
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 Maria Cecília Fernandes Dias Benzophenone 1,2,3-triazole CuAAC reaction antioxidant photoprotective cytotoxicity Bioquímica Fotoquímica orgânica Síntese orgânica Antioxidantes Melanoma |
| title_short |
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 |
| title_full |
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 |
| title_fullStr |
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 |
| title_full_unstemmed |
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 |
| title_sort |
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 |
| author |
Maria Cecília Fernandes Dias |
| author_facet |
Maria Cecília Fernandes Dias Bianca Lana de Sousa Marisa Ionta Róbson Ricardo Teixeira Thiago Quinelato Goulart Guilherme Álvaro Ferreira da Silva Eduardo Jorge Pilau Marcelo Henrique dos Santos |
| author_role |
author |
| author2 |
Bianca Lana de Sousa Marisa Ionta Róbson Ricardo Teixeira Thiago Quinelato Goulart Guilherme Álvaro Ferreira da Silva Eduardo Jorge Pilau Marcelo Henrique dos Santos |
| author2_role |
author author author author author author author |
| dc.contributor.author.fl_str_mv |
Maria Cecília Fernandes Dias Bianca Lana de Sousa Marisa Ionta Róbson Ricardo Teixeira Thiago Quinelato Goulart Guilherme Álvaro Ferreira da Silva Eduardo Jorge Pilau Marcelo Henrique dos Santos |
| dc.subject.por.fl_str_mv |
Benzophenone 1,2,3-triazole CuAAC reaction antioxidant photoprotective cytotoxicity |
| topic |
Benzophenone 1,2,3-triazole CuAAC reaction antioxidant photoprotective cytotoxicity Bioquímica Fotoquímica orgânica Síntese orgânica Antioxidantes Melanoma |
| dc.subject.other.pt_BR.fl_str_mv |
Bioquímica Fotoquímica orgânica Síntese orgânica Antioxidantes Melanoma |
| description |
CNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico |
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2021 |
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2021-03 |
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2023-04-26T11:34:10Z |
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2023-04-26T11:34:10Z |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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article |
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publishedVersion |
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http://hdl.handle.net/1843/52494 |
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https://doi.org/10.21577/0103-5053.20200211 |
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1678-4790 |
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https://doi.org/10.21577/0103-5053.20200211 http://hdl.handle.net/1843/52494 |
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1678-4790 |
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eng |
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eng |
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Journal of the Brazilian Chemical Society |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Universidade Federal de Minas Gerais |
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UFMG |
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Brasil |
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ICA - INSTITUTO DE CIÊNCIAS AGRÁRIAS |
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Universidade Federal de Minas Gerais |
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reponame:Repositório Institucional da UFMG instname:Universidade Federal de Minas Gerais (UFMG) instacron:UFMG |
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