1. Synthesis and Biological Evaluation of Apigenin Derivatives as Antibacterial and Antiproliferative Agents.
- Author
-
Rui Liu, Hongchi Zhang, Maosen Yuan, Jiao Zhou, Qin Tu, Jian-Jun Liu, and Jinyi Wang
- Subjects
APIGENIN ,CELL proliferation ,ANTIBACTERIAL agents ,MOIETIES (Chemistry) ,PSEUDOMONAS aeruginosa ,ELECTROSPRAY ionization mass spectrometry ,NUCLEAR magnetic resonance ,CELL lines - 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 C
2 or C3 spacers, respectively. The chemical structures of the apigenin derivatives were confirmed using1 H-NMR,13 C-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. [ABSTRACT FROM AUTHOR]- Published
- 2013
- Full Text
- View/download PDF