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Design and synthesis of (2-oxo-1,2-dihydroquinolin-4-yl)-1,2,3-triazole derivatives via click reaction: Potential apoptotic antiproliferative agents

El-Sheref, E. M.; Elbastawesy, M. A. I.; Brown, A. B.; Shawky, A. M.; Gomaa, H. A. M.; Bräse, S.; Youssif, B. G. M.


A mild and versatile method based on Cu-catalyzed [2+3] cycloaddition (Huisgen-Meldal-Sharpless reaction) was developed to tether 3,3’-((4-(prop-2-yn-1-yloxy)phenyl)methylene)bis(4-hydroxyquinolin-2(1H)-ones) with 4-azido-2-quinolones in good yields. This methodology allowed attaching three quinolone molecules via a triazole linker with the proposed mechanism. The products are interesting precursors for their anti-proliferative activity. Compound 8g was the most active one, achieving IC$_{50}$ = 1.2 ± 0.2 µM and 1.4 ± 0.2 µM against MCF-7 and Panc-1 cell lines, respectively. Moreover, cell cycle analysis of cells MCF-7 treated with 8g showed cell cycle arrest at the G2/M phase (supported by Caspase-3,8,9, Cytochrome C, BAX, and Bcl-2 studies). Additionally, significant pro-apoptotic activity is indicated by annexin V-FITC staining.

Verlagsausgabe §
DOI: 10.5445/IR/1000140520
Veröffentlicht am 01.12.2021
DOI: 10.3390/molecules26226798
Zitationen: 7
Web of Science
Zitationen: 6
Zitationen: 7
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Biologische und Chemische Systeme (IBCS)
Institut für Organische Chemie (IOC)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2021
Sprache Englisch
Identifikator ISSN: 1420-3049
KITopen-ID: 1000140520
HGF-Programm 43.33.11 (POF IV, LK 01) Adaptive and Bioinstructive Materials Systems
Erschienen in Molecules
Verlag MDPI
Band 26
Heft 22
Seiten 6798
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Schlagwörter click; azido; quinolones; triazole; anti-proliferative; apoptosis
Nachgewiesen in Dimensions
Web of Science
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