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J Cancer Res Ther. 2019 Jul-Sep;15(5):1141-1146. doi: 10.4103/jcrt.JCRT_948_17.

A new acetylacetone derivative inhibits breast cancer by apoptosis induction and angiogenesis inhibition.

Author information

Department of Clinical Pharmacy and Therapeutics, Applied Science Private University, Amman, Jordan.
Department of Chemistry, Hashemite University, Zarqa, Jordan.
Department of Biology and Biotechnology, Hashemite University, Zarqa, Jordan.



Cancer is one of the main causes of death worldwide. High mortality rates were reported among breast cancer patients which makes the development of new anticancer agents targeting breast cancer a priority. The synthesis of the compounds incorporating- N=N- group is an important field of research that may lead to the discovery of new anticancer drug.

Materials and Methods:

In this work, we report the synthesis of a compound has O and N centers with the incorporation of the arylazo group (4-BrC6H4-N=N-) into acetylacetone to synthesize 3-(4-Bromo phenylazo)-2,4-pentanedione. Physical characteristics of the newly synthesized compound were determined by measuring electronic absorption spectra, nuclear magnetic resonances, and the infrared absorption spectrum. The inhibitory effect of the compound against breast cancer cell lines was measured by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Its effect on angiogenesis was evaluated by measuring vascular endothelial growth factor (VEGF) levels in treated cells. The ability of the compound to induce apoptosis in cancer cells was tested by measuring caspase-3 activity, and its capacity to stimulate the immune system was evaluated by measuring the levels of interferon gamma (IFN-γ), interleukin-2 (IL-2), IL-4, and IL-10 cytokines in treated lymphocytes.


Significant antiproliferative activity against breast cancer cell lines was observed in treated cells. Low levels of VEGF and high caspase-3 activity were observed in treated cells. Levels of IFN-γ, IL-2, and IL-4 were increased after treating lymphocytes with this compound.


3-(4-Bromo phenylazo)-2,4-pentanedione is a promising anticancer agent that can inhibit breast cancer cells through apoptosis induction and angiogenesis inhibition. Further testing is needed to clearly determine the molecular mechanisms of the anticancer effect of this compound.


3-(4-Bromo phenylazo)-2; 4-pentanedione; angiogenesis inhibition; apoptosis; arylazo group; breast cancer; caspase-3; cell viability; vascular endothelial growth factor

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