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

Liu, Rui; Zhang, Hongchi; Yuan, Maosen; Zhou, Jiao; Tu, Qin; Liu, Jian-Jun; Wang, Jinyi

doi:10.3390/molecules180911496

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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

College of Agronomy and Life Sciences, Shanxi Datong University, Datong 037009, Shanxi, China

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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

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Abstract

Two series of apigenin [5,7-dihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one] derivatives, 3a–3j and 4a–4j, 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, 4a–4j 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 4a–4j 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

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MDPI and ACS Style

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. https://doi.org/10.3390/molecules180911496

AMA Style

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(9):11496-11511. https://doi.org/10.3390/molecules180911496

Chicago/Turabian Style

Liu, Rui, Hongchi Zhang, Maosen Yuan, Jiao Zhou, Qin Tu, Jian-Jun Liu, and Jinyi Wang. 2013. "Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents" Molecules 18, no. 9: 11496-11511. https://doi.org/10.3390/molecules180911496

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

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