Novel Cinobufagin Oxime Ether Derivatives as Potential Na+/K+-ATPase Inhibitors: Synthesis, Biological Screening and Molecular Docking

doi:10.1007/s40242-017-6487-1

Chemical Research in Chinese Universities ›› 2017, Vol. 33 ›› Issue (3): 378-383.doi: 10.1007/s40242-017-6487-1

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Novel Cinobufagin Oxime Ether Derivatives as Potential Na⁺/K⁺-ATPase Inhibitors: Synthesis, Biological Screening and Molecular Docking

LIANG Guangping^1,2, CHUNG Tseyu³, GUO Jinhua^1,2, ZHANG Rongrong^1,2, XÜ Wei^1,2, TZEN Jason T. C.³, JIANG Renwang^1,2

1. College of Pharmacy, Jinan University, Guangzhou 510632, P. R. China;
2. Guangdong Province Key Laboratory of Pharmacodynamic Constituents of TCM and New Drugs Research, Jinan University, Guangzhou 510632, P. R. China;
3. Graduate Institute of Biotechnology, ‘National Chung-Hsing University’, Taichung 40227, China

Received:2016-12-08 Revised:2017-03-02 Online:2017-06-01 Published:2017-04-05
Contact: TZEN Jason T.C.,E-mail:TCTZEN@dragon.nchu.edu.tw;JIANG Renwang,E-mail:trwjiang@jnu.edu.cn E-mail:TCTZEN@dragon.nchu.edu.tw;trwjiang@jnu.edu.cn
Supported by:
Supported by the National Natural Science Foundation of China(No.81573315), the Guangdong Natural Science Fund, China(No.2015A030313313) and the Guangzhou Industry-University Collaborative Innovation Major Projects, China(No. 201508030016).

Abstract

Abstract:

Some cinobufagin oxime ether derivatives as potential Na⁺/K⁺-ATPase inhibitors were synthesized by following the side chain of istaroxime. These compounds inhibit Na⁺/K⁺-ATPase in a dose-dependent manner. Compound 3c with an oxyethylamine side chain that is the same as that of istaroxime showed the most potent inhibition, which was stronger than compound 3a with only hydroxyoxime moiety at C3 and compound 3b with a methylated hydroxyoxime moiety. Molecular docking was used to explore the binding modes of the target compounds with Na⁺/K⁺-ATPase, which suggested that the longer ethyl amine group at C3 oxime moiety of compound 3c could make stronger interaction with Na⁺/K⁺-ATPase via intermolecular charge-charge and H-bond interaction as compared with other derivatives.

Key words: Cinobufagin, Istaroxime, Na⁺/K⁺-ATPase, Molecular docking

LIANG Guangping, CHUNG Tseyu, GUO Jinhua, ZHANG Rongrong, XÜ Wei, TZEN Jason T. C., JIANG Renwang. Novel Cinobufagin Oxime Ether Derivatives as Potential Na⁺/K⁺-ATPase Inhibitors: Synthesis, Biological Screening and Molecular Docking[J]. Chemical Research in Chinese Universities, 2017, 33(3): 378-383.

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Novel Cinobufagin Oxime Ether Derivatives as Potential Na⁺/K⁺-ATPase Inhibitors: Synthesis, Biological Screening and Molecular Docking

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