Hydrogen-bond-driven supramolecular helical assembly of a coumarin-substituted phthalonitrile derivative: synthesis and in vitro anticancer activity against colorectal adenocarcinoma,Acta Crystallographica Section D

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Hydrogen-bond-driven supramolecular helical assembly of a coumarin-substituted phthalonitrile derivative: synthesis and in vitro anticancer activity against colorectal adenocarcinoma
Acta Crystallographica Section D ( IF 2.6 ) Pub Date : 2022-08-25 , DOI: 10.1107/s2059798322007823
Füsun Topkan ₁ , Mücahit Özdemir ₁ , Beyza Nur Özkan ₂ , Kübra Bozali ₂ , Eray Metin Güler ₂ , Yunus Zorlu ₃ , Mustafa Bulut ₁ , Ahmet Orhan Görgülü ₁ , Bahattin Yalçın ₁

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Phthalonitrile derivatives are generally reported to crystallize in space groups P2₁/c and P1 in the literature. In this study, 7-hydroxy-4,8-dimethyl-3-pentylcoumarin (2) and its phthalonitrile derivative (2d) were crystallized; 2d crystallized in the rare trigonal space group R3. In the phthalonitrile derivative (2d), weak C—H…O hydrogen-bonding interactions promoted the formation of supramolecular double helices, and these supramolecular P and M double helices came together to form a honeycomb-like architectural motif involving one-dimensional tubular channels. In silico molecular-docking studies were performed to support the experimental processes and the results agree with each other. In vitro studies of compounds 2 and 2d were performed in LoVo colorectal adenocarcinoma and CCD18Co healthy human cell lines using flow cytometry. For compounds 2 and 2d, there was a statistically significant increase (p < 0.001) in both early and late apoptosis with respect to the control in a dose-dependent manner.

中文翻译：

香豆素取代邻苯二甲腈衍生物的氢键驱动超分子螺旋组装：合成及体外抗结直肠腺癌活性

文献中一般报道邻苯二甲腈衍生物在空间群P 2 ₁ / c和P 1中结晶。本研究对7-羟基-4,8-二甲基-3-戊基香豆素( 2 )及其邻苯二甲腈衍生物( 2d )进行了结晶；2d在稀有的三角空间群R 3中结晶。在邻苯二甲腈衍生物 ( 2d ) 中，弱 C—H…O 氢键相互作用促进了超分子双螺旋的形成，这些超分子P和M双螺旋聚集在一起形成一个蜂窝状的建筑图案，涉及一维管状通道。进行了计算机分子对接研究以支持实验过程，结果彼此一致。使用流式细胞仪在 LoVo 结直肠腺癌和 CCD18Co 健康人类细胞系中进行了化合物2和2d的体外研究。对于化合物2和2d ，相对于对照，早期和晚期细胞凋亡均以剂量依赖性方式显着增加 ( p < 0.001)。

更新日期：2022-08-25

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