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Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity
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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Received: 30 October 2012; in revised form: 30 November 2012 / Accepted: 5 December 2012 / Published: 11 December 2012
Abstract: A series of nitrogen-containing apigenin analogs 4a–j was synthesized via Mannich reactions to develop anticancer, antibacterial, and antioxidant agents from plant-derived flavonoids. The chemical structures of these compounds were confirmed using 1H-NMR, 13C-NMR, and ESI-MS. The in vitro biological activities of the analogs were evaluated via assays of their antiproliferative, antibacterial, and antioxidant activities. The prepared apigenin analogs exhibited different antiproliferative activities against four human cancer cell lines, namely human cervical (HeLa), human hepatocellular liver (HepG2), human lung (A549), and human breast (MCF-7) cancer cells. Compound 4i showed the most favorable in vitro antiproliferative activity with IC50 values of 40, 40, 223, and 166 μg/mL against HeLa, HepG2, A549, and MCF-7, respectively. The 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity assay also showed that 4i had the most potent antioxidant activity, with the smallest IC50 value (334.8 μg/mL). The antibacterial activities of the analogs were determined using a two-fold serial dilution technique against four pathogenic bacteria, namely Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa. All the prepared apigenin analogs exhibited more potent activities than the parent apigenin. Compounds 4h and 4j, in particular, exhibited the best inhibitory activities against the Gram-positive bacteria Staphylococcus aureus and Bacillus subtilis with MIC values of 3.91 and 1.95 μg/mL, respectively.
Keywords: apigenin analogs; antiproliferative activity; antibacterial activity; antioxidant activity
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Liu, R.; Zhao, B.; Wang, D.-E.; Yao, T.; Pang, L.; Tu, Q.; Ahmed, S.M.; Liu, J.-J.; Wang, J. Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity. Molecules 2012, 17, 14748-14764.
Liu R, Zhao B, Wang D-E, Yao T, Pang L, Tu Q, Ahmed SM, Liu J-J, Wang J. Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity. Molecules. 2012; 17(12):14748-14764.
Liu, Rui; Zhao, Bin; Wang, Dong-En; Yao, Tianyu; Pang, Long; Tu, Qin; Ahmed, Saeed M.; Liu, Jian-Jun; Wang, Jinyi. 2012. "Nitrogen-Containing Apigenin Analogs: Preparation and Biological Activity." Molecules 17, no. 12: 14748-14764.