Halogenated flavanones as potential apoptosis-inducing agents: synthesis and biological activity evaluation.

Abstract

A series of halogenated flavanones were synthesized from 2-hydroxychalcones and tested for their cytotoxicity against a panel of human cancer cell lines. Among the synthesized compounds, 3',7-dichloroflavanone (2d) showed the highest activity against MCF-7, LNCaP, PC3, Hep-G2, KB and SK-N-MC cells. However, 3',6-dichloroflavanone (2g) with IC(50) value of 2.9 ± 0.9 μM was the most potent compound against MDA-MB-231 cells, being approximately 12 times more active than etoposide as reference drug. According to the flow-cytometric analysis, compound 2g can induce apoptosis by 66.19 and 21.37% in PC3 and MDA-MB-231 cells, respectively. The results of acridine orange/ethidium bromide staining and TUNEL assay suggested that the cytotoxic activity of this compound in PC3 and MDA-MB-231 cells occurs via apoptosis.

• Authors: Maliheh Safavi, Nasim Esmati, Sussan Kabudanian Ardestani, Saeed Emami, Soheila Ajdari, Jamshid Davoodi, Abbas Shafiee, Alireza Foroumadi
• Journal: European journal of medicinal chemistry (Eur J Med Chem) Vol. 58 Pg. 573-80 (Dec 2012) ISSN: 1768-3254 [Electronic] France
• PMID: 23174316 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: Copyright © 2012 Elsevier Masson SAS. All rights reserved.

Chemical References

• Antineoplastic Agents
• Flavanones

Topics

• Antineoplastic Agents (chemical synthesis, chemistry, pharmacology)
• Apoptosis (drug effects)
• Cell Proliferation (drug effects)
• Dose-Response Relationship, Drug
• Drug Screening Assays, Antitumor
• Flavanones (chemical synthesis, chemistry, pharmacology)
• Humans
• MCF-7 Cells
• Molecular Structure
• Structure-Activity Relationship
• Tumor Cells, Cultured