Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| Outros Autores: | , , , , , , , , , , , , |
| Tipo de documento: | Artigo |
| Idioma: | eng |
| Título da fonte: | Repositório Institucional da FIOCRUZ (ARCA) |
| Texto Completo: | https://www.arca.fiocruz.br/handle/icict/57054 |
Resumo: | Federal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil. |
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Cruz, Eduardo H. G. daSilvers, Molly A.Jardim, Guilherme A. M.Resende, Jarbas M.Cavalcanti, Bruno C.Bomfim, Igor S.Pessoa, ClaudiaSimone, Carlos A. deBotteselle, Giancarlo V.Braga, Antonio L.Nair, Divya K.Namboothirig, Irishi N. N.Boothmanb, David A.Silva Júnior, Eufrânio N. da2023-02-14T02:35:34Z2023-02-14T02:35:34Z2021CRUZ, Eduardo H. G. da et al. Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights. European Journal of Medicinal Chemistry, p. 1-36, Oct. 2021.0223-5234https://www.arca.fiocruz.br/handle/icict/5705410.1016/j.ejmech.2016.06.019engElsevierSynthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insightsinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleFederal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil.University of Texas Southwestern Medical Center. Departments of Pharmacology and Radiation Oncology. Simmons Comprehensive Cancer Center. Road, Dallas, USA.Federal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil.Federal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil.Federal University of Ceará. National Laboratory of Experimental Oncology. Department of Physiology and Pharmacology. Fortaleza, CE, Brazil.Federal University of Ceará. National Laboratory of Experimental Oncology. Department of Physiology and Pharmacology. Fortaleza, CE, Brazil.Federal University of Ceará. National Laboratory of Experimental Oncology. Department of Physiology and Pharmacology. Fortaleza, CE, Brazil / Fundação Oswaldo Cruz. Fiocruz Ceará. Fortaleza, CE, Brazil.University of São Paulo. Institute of Physics. São Carlos, SP, Brazil.Federal University of Santa Catarina. Department of Chemistry. Florianópolis, SC, Brazil.Federal University of Santa Catarina. Department of Chemistry. Florianópolis, SC, Brazil.Indian Institute of Technology. Department of Chemistry. Bombay, Mumbai, India.Indian Institute of Technology. Department of Chemistry. Bombay, Mumbai, India.University of Texas Southwestern Medical Center. Departments of Pharmacology and Radiation Oncology. Simmons Comprehensive Cancer Center. Road, Dallas, USA.Federal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil.Selenium-containing quinone-based 1,2,3-triazoles were synthesized using click chemistry, the copper catalyzed azide-alkyne 1,3-dipolar cycloaddition, and evaluated against six types of cancer cell lines: HL-60 (human promyelocytic leukemia cells), HCT-116 (human colon carcinoma cells), PC3 (human prostate cells), SF295 (human glioblastoma cells), MDA-MB-435 (melanoma cells) and OVCAR-8 (human ovarian carcinoma cells). Some compounds showed IC50 values < 0.3 μM. The cytotoxic potential of the quinones evaluated was also assayed using non-tumor cells, exemplified by peripheral blood mononuclear (PBMC), V79 and L929 cells. Mechanistic role for NAD(P)H:Quinone Oxidoreductase 1 (NQO1) was also elucidated. These compounds could provide promising new lead derivatives for more potent anticancer drug development and delivery, and represent one of the most active classes of lapachones reported.β-LapachoneQuinoneClick chemistryChalcogensSeleniuminfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/57054/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALCruz_Eduardo_etal_CE_2016.pdfCruz_Eduardo_etal_CE_2016.pdfapplication/pdf3394476https://www.arca.fiocruz.br/bitstream/icict/57054/2/Cruz_Eduardo_etal_CE_2016.pdf45c5377835b5efb5025bad339f58aac6MD52icict/570542023-03-27 10:42:41.846oai:www.arca.fiocruz.br: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ório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-27T13:42:41Repositório Institucional da FIOCRUZ (ARCA) - 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| dc.title.en_US.fl_str_mv |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| title |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| spellingShingle |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights Cruz, Eduardo H. G. da β-Lapachone Quinone Click chemistry Chalcogens Selenium |
| title_short |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| title_full |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| title_fullStr |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| title_full_unstemmed |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| title_sort |
Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights |
| author |
Cruz, Eduardo H. G. da |
| author_facet |
Cruz, Eduardo H. G. da Silvers, Molly A. Jardim, Guilherme A. M. Resende, Jarbas M. Cavalcanti, Bruno C. Bomfim, Igor S. Pessoa, Claudia Simone, Carlos A. de Botteselle, Giancarlo V. Braga, Antonio L. Nair, Divya K. Namboothirig, Irishi N. N. Boothmanb, David A. Silva Júnior, Eufrânio N. da |
| author_role |
author |
| author2 |
Silvers, Molly A. Jardim, Guilherme A. M. Resende, Jarbas M. Cavalcanti, Bruno C. Bomfim, Igor S. Pessoa, Claudia Simone, Carlos A. de Botteselle, Giancarlo V. Braga, Antonio L. Nair, Divya K. Namboothirig, Irishi N. N. Boothmanb, David A. Silva Júnior, Eufrânio N. da |
| author2_role |
author author author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Cruz, Eduardo H. G. da Silvers, Molly A. Jardim, Guilherme A. M. Resende, Jarbas M. Cavalcanti, Bruno C. Bomfim, Igor S. Pessoa, Claudia Simone, Carlos A. de Botteselle, Giancarlo V. Braga, Antonio L. Nair, Divya K. Namboothirig, Irishi N. N. Boothmanb, David A. Silva Júnior, Eufrânio N. da |
| dc.subject.en.en_US.fl_str_mv |
β-Lapachone Quinone Click chemistry Chalcogens Selenium |
| topic |
β-Lapachone Quinone Click chemistry Chalcogens Selenium |
| description |
Federal University of Minas Gerais. Institute of Exact Sciences. Department of Chemistry. Belo Horizonte, MG, Brazil. |
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2021 |
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2021 |
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2023-02-14T02:35:34Z |
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2023-02-14T02:35:34Z |
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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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CRUZ, Eduardo H. G. da et al. Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights. European Journal of Medicinal Chemistry, p. 1-36, Oct. 2021. |
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https://www.arca.fiocruz.br/handle/icict/57054 |
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0223-5234 |
| dc.identifier.doi.none.fl_str_mv |
10.1016/j.ejmech.2016.06.019 |
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CRUZ, Eduardo H. G. da et al. Synthesis and Antitumor Activity of Selenium-Containing Quinone-based Triazoles Possessing Two Redox Centres, and their Mechanistic Insights. European Journal of Medicinal Chemistry, p. 1-36, Oct. 2021. 0223-5234 10.1016/j.ejmech.2016.06.019 |
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Elsevier |
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Elsevier |
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