European Journal of Medicinal Chemistry ( IF 6.0 ) Pub Date : 2017-05-05 , DOI: 10.1016/j.ejmech.2017.05.017 Demet Coskun , Merve Erkisa , Engin Ulukaya , Mehmet Fatih Coskun , Ferda Ari
Cancer treatment still requires new compounds to be discovered. Chalcone and its derivatives exhibit anticancer potential in different cancer cells. A new series of benzofuran substituted chalcone derivatives was synthesized by the base-catalyzed Claisen-Schmidt reaction of the 1-(7-ethoxy-1-benzofuran-2-yl) ethanone with different aromatic aldehydes to yield 1-(7-ethoxy-1-benzofuran-2-yl) substituted chalcone derivatives 3a-j. The derivatives were characterized by elemental analysis, FT-IR, 1H NMR and 13C NMR spectroscopy techniques. The anti-growth effect of chalcone compounds was tested in breast cancer (MCF-7), non-small cell lung cancer (A549) and prostate cancer (PC-3) cell lines by the SRB and ATP cell viability assays. Apoptosis was detected by mitochondrial membrane potential, Annexin V staining and caspase 3/7 activity. Formation of reactive oxygen species was determined by DCFDA. The results revealed that chalcone derivatives have anticancer activity with especially chalcone derivative 3a showing cytotoxic effects on cancer cells. In addition, chalcone derivative 3a induced apoptosis through caspase dependent pathways in prostate, lung and breast cancer cells.
中文翻译:
新型1-(7-乙氧基-1-苯并呋喃-2-基)取代的查尔酮衍生物:合成,表征和抗癌活性。
癌症治疗仍然需要发现新的化合物。查耳酮及其衍生物在不同的癌细胞中具有抗癌潜力。通过1-(7-乙氧基-1-苯并呋喃-2-基)乙酮与不同芳族醛的碱催化Claisen-Schmidt反应合成了一系列新的苯并呋喃取代的查尔酮衍生物,得到了1-(7-乙氧基- 1-苯并呋喃-2-基)取代的查耳酮衍生物3a-j。通过元素分析,FT-IR,1 H NMR和13对特征进行了表征13 C NMR光谱技术。查尔酮化合物的抗生长作用已通过SRB和ATP细胞活力测定法在乳腺癌(MCF-7),非小细胞肺癌(A549)和前列腺癌(PC-3)细胞系中进行了测试。通过线粒体膜电位,膜联蛋白V染色和胱天蛋白酶3/7活性检测凋亡。活性氧物质的形成由DCFDA确定。结果表明查尔酮衍生物具有抗癌活性,尤其是查尔酮衍生物3a对癌细胞具有细胞毒性作用。另外,查耳酮衍生物3a通过胱天蛋白酶依赖性途径在前列腺癌细胞,肺癌细胞和乳腺癌细胞中诱导凋亡。