Loading…

Superior anticancer activity of halogenated chalcones and flavonols over the natural flavonol quercetin

A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the r...

Full description

Saved in:
Bibliographic Details
Published in:European journal of medicinal chemistry 2013-07, Vol.65, p.500-510
Main Authors: Dias, Tatiana A., Duarte, Cecília L., Lima, Cristovao F., Proença, M. Fernanda, Pereira-Wilson, Cristina
Format: Article
Language:English
Subjects:
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A series of chalcone and flavonol derivatives were synthesized in good yield by an eco-friendly approach. A pharmacological evaluation was performed with the human colorectal carcinoma cell line HCT116 and revealed that the anticancer activity of flavonols was higher when compared with that of the respective chalcone precursors. The antiproliferative activity of halogenated derivatives increases as the substituent in the 3- or 4-positon of the B-ring goes from F to Cl and to Br. In addition, halogens in position 3 enhance anticancer activity in chalcones whereas for flavonol derivatives the best performance was registered for the 4-substituted derivatives. Flow cytometry analysis showed that compounds 3p and 4o induced cell cycle arrest and apoptosis as demonstrated by increased S, G2/M and sub-G1 phases. These data were corroborated by western blot and fluorescence microscopy analysis. In summary, halogenated chalcones and flavonols were successfully prepared and presented high anticancer activity as shown by their cell growth and cell cycle inhibitory potential against HCT116 cells, superior to that of quercetin, used as a positive control. [Display omitted] •Methoxylated and halogenated chalcones and flavonols were synthesized in good yield.•Pharmacological assays used the human colorectal carcinoma cell line HCT116.•Brominated flavonoids displayed enhanced anticancer activity.•Compounds 3p and 4o induced cell cycle arrest and apoptosis.
ISSN:0223-5234
1768-3254
DOI:10.1016/j.ejmech.2013.04.064