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

Topkan F., ÖZDEMİR M., Ozkan B. N., Bozali K., Guler E. M., Zorlu Y., ...More

ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY, vol.78, pp.1143-1155, 2022 (SCI-Expanded) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 78
  • Publication Date: 2022
  • Doi Number: 10.1107/s2059798322007823
  • Journal Name: ACTA CRYSTALLOGRAPHICA SECTION D-STRUCTURAL BIOLOGY
  • Journal Indexes: 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
  • Page Numbers: pp.1143-1155
  • Keywords: double helices, X-ray crystallography, colorectal cancer, coumarin-linked phthalonitrile derivative, LoVo cells, EPSTEIN-BARR-VIRUS, AGENTS, ACTIVATION, INHIBITION, DOCKING, BINDING, GROWTH, POTENT, CELLS, PI
  • Marmara University Affiliated: Yes

Abstract

Phthalonitrile derivatives are generally reported to crystallize in space groups P2(1)/c and P (1) over bar 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) over bar. In the phthalonitrile derivative (2d), weak C-H center dot center dot center dot 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.