Solid-phase synthesis of 2′-hydroxychalcones. Effects on cell growth inhibition, cell cycle and apoptosis of human tumor cell lines

Thirty-one substituted 2′-hydroxychalcones were prepared via an aldol condensation via a solid-phase approach. Chalcones were tested for their growth inhibitory activity in three human tumor cell lines using a SRB assay. To gain further insight on the cellular mechanism of action of this class of co...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2012-01, Vol.20 (1), p.25-33
Main Authors: Neves, Marta Perro, Cravo, Sara, Lima, Raquel T., Vasconcelos, M. Helena, Nascimento, M. São José, Silva, Artur M.S., Pinto, Madalena, Cidade, Honorina, Corrêa, Arlene G.
Format: Article
Language:English
Subjects:
2′-Hydroxychalcones
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antitumor
Apoptosis
Benzaldehydes - chemistry
Biological and medical sciences
Cell cycle
Cell Cycle Checkpoints - drug effects
Cell Line, Tumor
Cell Proliferation - drug effects
Chalcones - chemical synthesis
Chalcones - chemistry
Chalcones - pharmacology
Drug Screening Assays, Antitumor
Humans
Medical sciences
Pharmacology. Drug treatments
Solid-phase
Solid-Phase Synthesis Techniques
Structure-Activity Relationship
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Summary:Thirty-one substituted 2′-hydroxychalcones were prepared via an aldol condensation via a solid-phase approach. Chalcones were tested for their growth inhibitory activity in three human tumor cell lines using a SRB assay. To gain further insight on the cellular mechanism of action of this class of compounds, studies of their effect on cell cycle profile as well as on induction of cellular apoptosis were also carried out. Thirty-one 2′-hydroxychalcones were prepared via solid-phase synthesis by base-catalyzed aldol condensation of substituted 2′-hydroxyacetophenones and benzaldehydes. Chalcones were tested for their growth inhibitory activity in three human tumor cell lines (MCF-7, NCI-H460 and A375-C5) using the SRB assay. Results revealed that several of the tested compounds caused a pronounced dose-dependent growth inhibitory effect on the tumor cell lines studied in the low micromolar range. To gain further insight on the cellular mechanism of action of this class of compounds, studies of their effect on cell cycle profile as well as on induction of cellular apoptosis were also carried out. Generally, the tested chalcones interfered with the cell cycle profile and increased the percentage of apoptotic MCF-7 cells. The results here presented may help to identify new chalcone-like structures with optimized cell growth inhibitory activity which may be further tested as potential antitumor agents.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2011.11.042