The stilbene and dibenzo[b,f]oxepine derivatives as anticancer compounds

Damian Garbicz , Piotr Tobiasz , Filip Borys , Tomasz Pilżys , Michał Marcinkowski , Marcin Poterała , Elżbieta Grzesiuk , Hanna Krawczyk

Abstract

In the present study, the synthesis and cytotoxic effect of six stilbenes and three oxepine derivatives against two cancerous – HeLa and U87, and two normal – EUFA30 and HEK293 cell lines has been reported. The results of cytotoxic assay and flow cytometry analysis revealed that compounds 9-nitrobenzo[b]naphtho[1,2-f]oxepine (4), (E)-3,3′,4,4′,5,5′-hexamethoxystilbene (6) and 4-hydroxy-2′,4′-dinitrostilbene (8) were the most active and their interaction with tubulin (crystal structure from PDB) has been analyzed by computer molecular modeling. Molecular docking of these compounds on colchicine binding site of the tubulin indicates the interaction of (4), (6) and (8) with tubulin. The compound (4) could interact stronger with tubulin, relative to colchicine, however, with no selectivity of action against cancer and normal cells. Conversely, compounds (6) and (8) interact more weakly with tubulin, relative to colchicine but they act more selectively towards cancerous versus normal cell lines. Obtained results proved that the compounds that are the most active against cancerous cells operate through tubulin binding.

Author Damian Garbicz
Damian Garbicz,,
-
, Piotr Tobiasz (FC)
Piotr Tobiasz,,
- Faculty of Chemistry
, Filip Borys (FC / DOC)
Filip Borys,,
- Department Of Organic Chemistry
, Tomasz Pilżys
Tomasz Pilżys,,
-
, Michał Marcinkowski
Michał Marcinkowski,,
-
, Marcin Poterała (FC / DOC)
Marcin Poterała,,
- Department Of Organic Chemistry
, Elżbieta Grzesiuk
Elżbieta Grzesiuk,,
-
, Hanna Krawczyk (FC / DOC)
Hanna Krawczyk,,
- Department Of Organic Chemistry
Journal seriesBiomedicine & Pharmacotherapy, [Biomedicine and Pharmacotherapy], ISSN 0753-3322, e-ISSN 1950-6007
Issue year2020
Vol123
ASJC Classification2700 General Medicine; 3004 Pharmacology
DOIDOI:10.1016/j.biopha.2019.109781
Languageen angielski
Score (nominal)100
Score sourcejournalList
ScoreMinisterial score = 100.0, 15-07-2020, ArticleFromJournal
Publication indicators Scopus Citations = 0; Scopus SNIP (Source Normalised Impact per Paper): 2018 = 0.951; WoS Impact Factor: 2018 = 3.743 (2) - 2018=3.615 (5)
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