Please use this identifier to cite or link to this item:
http://hdl.handle.net/1843/52494| Type: | Artigo de Periódico |
| 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 |
| Authors: | 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 |
| Abstract: | Benzophenones 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. |
| Subject: | Bioquímica Fotoquímica orgânica Síntese orgânica Antioxidantes Melanoma |
| language: | eng |
| metadata.dc.publisher.country: | Brasil |
| Publisher: | Universidade Federal de Minas Gerais |
| Publisher Initials: | UFMG |
| metadata.dc.publisher.department: | ICA - INSTITUTO DE CIÊNCIAS AGRÁRIAS |
| Rights: | Acesso Aberto |
| metadata.dc.identifier.doi: | https://doi.org/10.21577/0103-5053.20200211 |
| URI: | http://hdl.handle.net/1843/52494 |
| Issue Date: | Mar-2021 |
| metadata.dc.url.externa: | https://www.scielo.br/j/jbchs/a/kRdTFjZzWW94z6MQvKgSVkJ/abstract/?lang=en |
| metadata.dc.relation.ispartof: | Journal of the Brazilian Chemical Society |
| Appears in Collections: | Artigo de Periódico |
Files in This Item:
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.