Volume 78, Issue 9 pp. 1143-1155
research papers

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

Füsun Topkan

Füsun Topkan

Marmara University, Department of Chemistry, Istanbul, 34722 Türkiye

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Mücahit Özdemir

Mücahit Özdemir

Marmara University, Department of Chemistry, Istanbul, 34722 Türkiye

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Beyza Nur Özkan

Beyza Nur Özkan

University of Health Sciences, Department of Medical Biochemistry, Istanbul, 34668 Türkiye

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Kübra Bozali

Kübra Bozali

University of Health Sciences, Department of Medical Biochemistry, Istanbul, 34668 Türkiye

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Eray Metin Güler

Eray Metin Güler

University of Health Sciences, Department of Medical Biochemistry, Istanbul, 34668 Türkiye

University of Health Sciences, Department of Medical Biochemistry, Istanbul, 34668 Türkiye

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Yunus Zorlu

Yunus Zorlu

Gebze Technical University, Department of Chemistry, Kocaeli, 41400 Türkiye

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Mustafa Bulut

Mustafa Bulut

Marmara University, Department of Chemistry, Istanbul, 34722 Türkiye

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Ahmet Orhan Görgülü

Ahmet Orhan Görgülü

Marmara University, Department of Chemistry, Istanbul, 34722 Türkiye

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Bahattin Yalçın

Corresponding Author

Bahattin Yalçın

Marmara University, Department of Chemistry, Istanbul, 34722 Türkiye

Bahattin Yalçın, e-mail: [email protected]Search for more papers by this author
First published: 25 August 2022
Citations: 1

Abstract

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.

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