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Molecules 2014, 19(5), 6368-6381; doi:10.3390/molecules19056368
Article

Synthesis, Molecular Docking and Biological Evaluation of Glycyrrhizin Analogs as Anticancer Agents Targeting EGFR

1
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Received: 10 April 2014; in revised form: 4 May 2014 / Accepted: 14 May 2014 / Published: 19 May 2014
(This article belongs to the Section Medicinal Chemistry)
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Abstract: Glycyrrhizin (GA) analogs in the form of 3-glucuronides and 18-epimers were synthesized and their anticancer activities were evaluated. Alkaline isomerization of monoglucuronides is reported. In vitro and in vivo studies showed that glycyrrhetinic acid monoglucuronides (GAMGs) displayed higher anticancer activities than those of bisglucuronide GA analogs, while anticancer activity of the 18α-epimer was superior to that of the 18β-epimer. 18α-GAMG was firstly nicely bound to epidermal growth factor receptor (EGFR) via six hydrogen bonds and one charge interaction, and the docking calculation proved the correlation between anticancer activities and EGFR inhibitory activities. Highly active 18α-GAMG is thus of interest for the further studies as a potential anticancer agent.
Keywords: glycyrrhizin; anticancer activity; EGFR; 18-epimer; molecular docking glycyrrhizin; anticancer activity; EGFR; 18-epimer; molecular docking
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Yang, Y.-A.; Tang, W.-J.; Zhang, X.; Yuan, J.-W.; Liu, X.-H.; Zhu, H.-L. Synthesis, Molecular Docking and Biological Evaluation of Glycyrrhizin Analogs as Anticancer Agents Targeting EGFR. Molecules 2014, 19, 6368-6381.

AMA Style

Yang Y-A, Tang W-J, Zhang X, Yuan J-W, Liu X-H, Zhu H-L. Synthesis, Molecular Docking and Biological Evaluation of Glycyrrhizin Analogs as Anticancer Agents Targeting EGFR. Molecules. 2014; 19(5):6368-6381.

Chicago/Turabian Style

Yang, Yong-An; Tang, Wen-Jian; Zhang, Xin; Yuan, Ji-Wen; Liu, Xin-Hua; Zhu, Hai-Liang. 2014. "Synthesis, Molecular Docking and Biological Evaluation of Glycyrrhizin Analogs as Anticancer Agents Targeting EGFR." Molecules 19, no. 5: 6368-6381.



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