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Synthesis of novel cyanine dyes as antitumor agents
Archiv der Pharmazie ( IF 4.3 ) Pub Date : 2020-11-10 , DOI: 10.1002/ardp.202000186
Ahmed A Fadda 1 , Eman H Tawfik 1, 2 , Marwa Abdel-Motaal 1, 3 , Yasser A Selim 4
Affiliation  

In this study, some novel cyanine dyes, 1, 3, and 5-15, were synthesized by a one-pot step reaction of pyridinium salts 2 and/or 4 with benzenaminium salt 1. N-{[1-Chloro-3,4-dihydronaphthalen-2-yl)methylene]benzenaminium} chloride 1 was obtained by the reaction of α-tetralone with Vilsmeier-Haack reagent, followed by a mixture of an equimolar ratio of anilin/ethanol (1:1). All new cyanine dyes were evaluated in vitro for their anticancer activity against two cell lines, that is, HepG2 (human hepatocellular liver carcinoma) and MCF-7 (breast cancer). The obtained results were compared with human lung fibroblasts (WI-38) and Vero cells (derived from the kidney of an African green monkey) as normal cells. In particular, some of these compounds, 6, 9, 13, and 14, were found to be the most potent derivatives against all the cancer cell lines, without effect on the normal cells. According to the structure-activity relationship, compound 13 (IC50 = 8.8 µg/ml) exhibited a higher activity against HepG2 cells, as it contains the azo group and two phenyl rings and due to the presence of the π-conjugated system attached to the two pyridine rings. Compound 6 (IC50 = 8 µg/ml) exhibited a higher activity against MCF-7 cells, as it contains two chlorine atoms and the π-conjugated system of the pyridine rings.

中文翻译:

作为抗肿瘤剂的新型花青染料的合成

在本研究中,一些新型花青染料 1、3 和 5-15 通过吡啶盐 2 和/或 4 与苯胺盐 1 的一锅步反应合成。 N-{[1-Chloro-3, 4-二氢萘-2-基)亚甲基]苯胺}氯化物1是通过α-四氢萘酮与Vilsmeier-Haack试剂反应,然后加入等摩尔比苯胺/乙醇(1:1)的混合物获得的。所有新的花青染料都在体外评估了它们对两种细胞系的抗癌活性,即 HepG2(人肝细胞肝癌)和 MCF-7(乳腺癌)。将获得的结果与作为正常细胞的人肺成纤维细胞(WI-38)和Vero细胞(来自非洲绿猴的肾脏)进行比较。特别是,其中一些化合物 6、9、13 和 14 被发现是对抗所有癌细胞系最有效的衍生物,对正常细胞无影响。根据构效关系,化合物 13 (IC50 = 8.8 µg/ml) 对 HepG2 细胞表现出更高的活性,因为它含有偶氮基团和两个苯环,并且由于存在与两个吡啶环。化合物 6 (IC50 = 8 µg/ml) 对 MCF-7 细胞表现出更高的活性,因为它含有两个氯原子和吡啶环的 π 共轭系统。
更新日期:2020-11-10
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