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Novel Symmetrical 1,4-Disubstituted-bis-1,2,3-Triazoles: Synthesis by Double CuAAC and Cytotoxicity Evaluation

[ Vol. 18 , Issue. 17 ]

Author(s):

Wallace Junio Reis, Paulo Otavio Lourenco Moreira, Rosemeire B. Alves, Heloisa H. Marques Oliveira, Luciana Maria Silva, Fernando Pilla Varotti and Rossimiriam Pereira Freitas*   Pages 1475 - 1482 ( 8 )

Abstract:


A series of symmetrical 1,4-disubstituted bis-1,2,3-triazoles was prepared by double copper catalyzed azide-alkyne cycloaddition (CuAAC) from aliphatic bis-azides and a tetraethylene glycol bisazide derivative. The eighteen novel compounds were evaluated in vitro for their cytotoxic activity against two human tumor cell lines: human breast adenocarcinoma (MDA-MB 231) and ovarian adenocarcinoma (TOV-21G). The results of colorimetric MTT assays showed that compounds 4j and 4q exhibited a better selectivity index and cell viability comparable with the standard drug doxorubicin. These compounds induced apoptosis in both tested cell lines, as assessed by BrdU assay. The results suggest that these structurally simple compounds may be promising prototypes for antitumoral agents.

Keywords:

Symmetrical bis-1, 2, 3-triazoles, Bis-azides, Double CuAAC, Cytotoxicity, BrdU, Apoptosis, Cancer.

Affiliation:

Departamento de Química. ICEx. UFMG. Av. Pres. Antônio Carlos. 6627. Pampulha. Belo Horizonte - MG. 31270-901, Núcleo de Pesquisa em Química Biológica, Universidade Federal de São João del-Rei - Campus Centro-Oeste. Av. Sebastião Gonçalves Coelho. 400. Divinópolis - MG. 35501-296, Departamento de Química. ICEx. UFMG. Av. Pres. Antônio Carlos. 6627. Pampulha. Belo Horizonte - MG. 31270-901, Fundação Ezequiel Dias, Laboratório de Biologia Celular, Belo Horizonte - MG, 30510-010, Fundação Ezequiel Dias, Laboratório de Biologia Celular, Belo Horizonte - MG, 30510-010, Núcleo de Pesquisa em Química Biológica, Universidade Federal de São João del-Rei - Campus Centro-Oeste. Av. Sebastião Gonçalves Coelho. 400. Divinópolis - MG. 35501-296, Departamento de Química. ICEx. UFMG. Av. Pres. Antônio Carlos. 6627. Pampulha. Belo Horizonte - MG. 31270-901



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