期刊
JOURNAL OF THE BRAZILIAN CHEMICAL SOCIETY
卷 32, 期 3, 页码 572-587出版社
SOC BRASILEIRA QUIMICA
DOI: 10.21577/0103-5053.20200211
关键词
benzophenone; 1,2,3-triazole; CuAAC reaction; antioxidant; photoprotective; cytotoxicity
资金
- FAPEMIG
- CAPES
- FINEP
- CNPq
Benzophenones have multiple biological activities, and the synthesized 1,2,3-triazole-benzophenone derivatives exhibit good antioxidant, anticancer, and photoprotective effects, with derivatives 19, 20, and 24 showing cytotoxicity and cell cycle arrest in melanoma cells.
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-yn1-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 jig 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.
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