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: Structural Biology, cilt.78, sa.Pt 9, ss.1143-1155, 2022 (SCI-Expanded, SSCI, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 78 Sayı: Pt 9
- Basım Tarihi: 2022
- Doi Numarası: 10.1107/s2059798322007823
- Dergi Adı: Acta Crystallographica Section D: Structural Biology
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Social Sciences Citation Index (SSCI), Scopus, Academic Search Premier, Aerospace Database, BIOSIS, CAB Abstracts, Chemical Abstracts Core, Communication Abstracts, EMBASE, Food Science & Technology Abstracts, INSPEC, MEDLINE, Metadex, Veterinary Science Database, Civil Engineering Abstracts
- Sayfa Sayıları: ss.1143-1155
- Anahtar Kelimeler: double helices, X-ray crystallography, colorectal cancer, coumarin-linked phthalonitrile derivative, LoVo cells
- Sağlık Bilimleri Üniversitesi Adresli: Evet
Özet
Phthalonitrile derivatives are generally reported to crystallize in space groups P21/c and P 1 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 R 3. In the phthalonitrile derivative (2d), weak C-HO 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.