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Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents

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Colleges of Science and Forestry, Northwest A&F University, Yangling 712100, Shaanxi, China
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College of Agronomy and Life Sciences, Shanxi Datong University, Datong 037009, Shanxi, China
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Authors to whom correspondence should be addressed.
Molecules 2013, 18(9), 11496-11511; https://doi.org/10.3390/molecules180911496
Received: 8 July 2013 / Revised: 2 September 2013 / Accepted: 12 September 2013 / Published: 17 September 2013
Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a3j and 4a4j, were synthesized. The apigenin and alkyl amines moieties of these compounds were separated by C2 or C3 spacers, respectively. The chemical structures of the apigenin derivatives were confirmed using 1H-NMR, 13C-NMR, and electrospray ionization mass spectroscopy. The in vitro antibacterial and antiproliferative activities of all synthesized compounds were determined. Among the tested compounds, 4a4j displayed significant antibacterial activity against the tested strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa). Additionally, 4i showed the best inhibitory activity with minimum inhibitory concentrations of 1.95, 3.91, 3.91, and 3.91 μg/mL against S. aureus, B. subtilis, E. coli, and P. aeruginosa, respectively. The antiproliferative activity of the apigenin derivatives was evaluated by an MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide] assay. We determined that 4a4j displayed better growth inhibition activity against four human cancer cell lines, namely, human lung (A549), human cervical (HeLa), human hepatocellular liver (HepG2), and human breast (MCF-7) cancer cells, than the parent apigenin. Compound 4j was found to be the most active antiproliferative compound against the selected cancer cells. Structure-activity relationships were also discussed based on the obtained experimental data. View Full-Text
Keywords: synthesis; biological evaluation; apigenin derivatives; antibacterial activity; antiproliferative activity; MTT assay synthesis; biological evaluation; apigenin derivatives; antibacterial activity; antiproliferative activity; MTT assay
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Liu, R.; Zhang, H.; Yuan, M.; Zhou, J.; Tu, Q.; Liu, J.-J.; Wang, J. Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents. Molecules 2013, 18, 11496-11511.

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