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

doi:10.1007/s40242-017-6487-1

高等学校化学研究 ›› 2017, Vol. 33 ›› Issue (3): 378-383.doi: 10.1007/s40242-017-6487-1

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

收稿日期:2016-12-08 修回日期:2017-03-02 出版日期:2017-06-01 发布日期:2017-04-05
通讯作者: 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
基金资助:
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).

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).

摘要/Abstract

摘要：

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.

关键词: Cinobufagin, Istaroxime, Na⁺/K⁺-ATPase, Molecular docking

Abstract:

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]. 高等学校化学研究, 2017, 33(3): 378-383.

参考文献

[1] Skou J. C., Angew. Chem. Int. Ed., 1998, 37, 2320
[2] Kaplan J. H., Annu. Rev. Biochem., 2002, 71, 511
[3] Laursen M., Gregersen J. L., Yatime L., Nissen P., Fedosova N. U., P. Natl. Acad. Sci. USA, 2015, 112, 1755
[4] Bavishi C., Khan A. R., Ather S., Int. J. Cardiol., 2015, 188, 99
[5] Li Z., Xie Z., Pfluügers Arch, 2009, 457, 635
[6] Prassas I., Diamandis E. P., Nat. Rev. Drug Discov., 2008, 7, 926
[7] Tian H. Y., Wang L., Zhang X. Q., Zhang D. M., Wang Y., Jiang R. W., Ye W. C., Steroids, 2010, 75, 884
[8] Tian H. Y., Wang L., Zhang X. Q., Wang Y., Zhang D. M., Jiang R. W., Liu Z., Liu J. S., Li Y. L., Ye W. C., Chem. Eur. J., 2010, 16, 10989
[9] Tian H. Y., Luo S. L., Liu J. S., Wang L., Wang Y., Zhang D. M., Zhang X. Q., Jiang R. W., Ye W. C., J. Nat. Prod., 2013, 76, 1842
[10] Li B. J., Tian H. Y., Zhang D. M., Lei Y. H., Wang L., Jiang R. W., Ye W. C., Fitoterapia, 2015, 105, 7
[11] Tian H. Y., Zhang P. W., Liu J. S., Zhang D. M., Zhang X. Q., Jiang R. W., Ye W. C., Chin. Chem. Lett., 2014, 25, 1104
[12] Cheng W., Tan Y. F., Tian H. Y., Gong X. W., Chen K. L., Jiang R. W., Nat. Prod. Res., 2014, 28, 901
[13] Zhang R. R., Tian H. Y., Tan Y. F., Chung T. Y., Sun X. H., Xia X., Ye W. C., Middleton D. A., Fedosova N., Esmann M., Tzen J. T. C., Jiang R. W., Org. Biomol. Chem., 2014, 12, 8919
[14] Tian H. Y., Yuan X. F., Jin L., Li J., Luo C., Ye W. C., Jiang R. W., Chem. Biol. Interact., 2014, 207, 16
[15] Zhang P. W., Tang H. J., Tian H. Y., Zhang R. R., Jiang R. W., Chin. J. Struct. Chem., 2014, 33, 1123
[16] Gobbini M., Armaroli S., Banfi L., Benicchio A., Carzana G., Fedrizzi G., Ferrari P., Giacalone G., Giubileo M., Marazzi G., Micheletti R., Moro B., Pozzi M., Scotti P. E., Torri M., Cerri A., J. Med. Chem., 2008, 51, 4601
[17] Aditya S., Rattan A., J. Pharmacol. Pharmacother., 2012, 3, 353
[18] Meng Q., Yau L. F., Lu J. G., Wu Z. Z., Zhang B. X., Wang J. R., Jiang Z. H., J. Ethnopharmacol., 2016, 187, 74
[19] Hirai Y., Morishita S., Ito C., Sakanashi M., Nihon Yakurigaku Zasshi, 1992, 100, 127
[20] Wang Z. J., Sun L., Heinbockel T., PLoS One, 2014, 9, e113272
[21] Zhang G., Wang C., Sun M., Li J., Wang B., Jin C., Hua P., Song G., Zhang Y., Nguyen L. L., Cui R., Liu R., Wang L., Zhang X., Onco-target, 2016, 7, 28935
[22] Li P., Song Q., Liu T., Wu Z., Chu X., Zhang X., Zhang Y., Gao Y., Zhang J., Chu L., Scientific World Journal, 2014, 2014, 496705
[23] Hao S., Bao Y. M., An L. J., Cheng W., Zhao R. G., Bi J., Wang H. S., Sun C. S., Liu J. W., Jiang B., Toxicol. in Vitro, 2011, 25, 1644
[24] Zhang Z., Li Z., Tian J., Jiang W., Wang Y., Zhang X., Li Z., You Q. D., Shapiro J. I., Si S., Xie Z., Mol. Pharmacol., 2010, 77, 961
[25] Xie Z., Wang Y., Liu G., Zolotarjova N., Periyasamy S. M., Askari A., Arch. Biochem. Biophys., 1996, 330, 153
[26] Brooks B. R., Bruccoleri R. E., Olafson B. D., States D. J., Swaminathan S., Karplus M., J. Comp. Chem., 1983, 4, 187
[27] Dixon S. L., Jr. Merz K. M., J. Med. Chem., 2001, 44, 3795
[28] He X. J., Tang J. S., Qiao A. M., Wang G. H., Jiang M. M., Liu R. H., Yao X. S., Steroids, 2006, 71, 392

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

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

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Ghadah F. ALJOHANI, Fatma A. A. EL-HAG, Mohamed S. BEKHEIT, Ewies F. EWIES, May A. EL-MANAWATY. An Efficient One-pot Synthesis of Certain Stereoselective Spiro[pyrazole-4,5'-isoxazoline]-5-one Derivatives: In vitro Evaluation of Antitumor Activities,Molecular Docking and In silico ADME Predictions[J]. 高等学校化学研究, 2022, 38(4): 1073-1082.
[2]	QUAN Jishun, ZHANG Dongping, ZHANG Zhuo, WANG Jian, MA Chao, CHENG Maosheng. Design, Synthesis and Biological Evaluation of Pyrrolo[2,1-c] [1,4]benzodiazepine-3,11-dione Derivatives as Novel Neuroprotective Agents[J]. 高等学校化学研究, 2021, 37(3): 647-654.
[3]	LI Huangong, ZHAO Yangyang, SUN Pengwei, GAO Li, XIONG Lixia, YANG Na, ZHOU Sha, LI Yuxin, LI Zhengming. Targeted Synthesis of Anthranilic Diamides Insecticides Containing Trifluoroethoxyl Phenylpyrazole[J]. 高等学校化学研究, 2021, 37(3): 655-661.
[4]	CHEN Aiyu, LIANG Yongdong, YE Jiao, HU Aixi, LIAN Wenwen, LIU Ailin, DU Guanhua. Synthesis of Chalcone Derivatives Containing Furan or/and Pyran Ring as Neuraminidase Inhibitors[J]. 高等学校化学研究, 2019, 35(3): 395-402.
[5]	LIU Sicheng, SUN Shijun. Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties[J]. 高等学校化学研究, 2019, 35(3): 478-484.
[6]	MA Junjie, HUANG Kun, NI Xin, CHEN Roufen, XU Boxuan, WANG Cuifang. Design, Synthesis, Biological Activity and Molecular Docking Study of Coumarin Derivatives Bearing 2-Methyl b iphenyl Moiety[J]. 高等学校化学研究, 2019, 35(3): 410-417.
[7]	ZHAO Xiaohui, QIU Youli, JIANG Long, LI Yu. Analysis of Affinity Energy Between Biphenyl Dioxygenase and Polychlorinated Biphenyls Using Molecular Docking[J]. 高等学校化学研究, 2019, 35(2): 325-332.
[8]	JIN Bo, TAO Ye, YANG Hongliang. Synthesis, Biological Evaluation and Molecular Docking of Novel Phenylpyrimidine Derivatives as Potential Anticancer Agents[J]. 高等学校化学研究, 2018, 34(6): 912-917.
[9]	HE Wei, ZHAO Anran, ZOU Jiajia, LUO Xuan, LIN Xiao, WANG Lisheng, LIN Cuiwu. Synthesis, In vitro Coagulation Activities and Molecular Docking Studies on Three L-Histidine Amide Derivatives[J]. 高等学校化学研究, 2018, 34(1): 90-94.
[10]	GUO Jinhua, TAN Bei, YE Qingmei, LIANG Guangping, YI Min, JIANG Renwang. Synthesis and Cytotoxic Activities of Spin-labeled Derivatives of Cinobufagin[J]. 高等学校化学研究, 2017, 33(4): 581-586.
[11]	LI Xu, LI Chuanhua, JIANG Jianhong, GU Huiwen, WEI Deliang, YE Lijuan, HU Jilin, XIAO Shengxiong, ZHANG Hui, LI Xia, LI Qiangguo. Fluorescence Spectroscopic Studies on the Interaction Between a New Bismuth(III) Schiff Base Complex and Bovine Serum Albumin[J]. 高等学校化学研究, 2017, 33(2): 166-171.
[12]	YANG Haoran, REN Yujie, GAO Xiaodong, GAO Yonghong. Synthesis and Anticoagulant Bioactivity Evaluation of 1, 2, 5-Trisubstituted Benzimidazole Fluorinated Derivatives[J]. 高等学校化学研究, 2016, 32(6): 973-978.
[13]	CHEN Jiawen, XU Lin, SUN Shiyang, ZHANG Huafei, MA Tonghui, SU Weiheng, JIANG Chunlai. Identification of Cinobufagin and Resibufogenin as Inhibitors of Enterovirus 71 Infection[J]. 高等学校化学研究, 2014, 30(6): 953-958.
[14]	FANG Ting, SUN Chuanwen, XU Yiyi, YUAN Jing, WANG Yuanfeng, XING Jiahua. Synthesis, Insecticidal Activities and Molecular Docking Studies on cis-Nitenpyram Analogues with a Flexible Amido Segment Anchored on Tetrahydropyrimidine Ring[J]. 高等学校化学研究, 2014, 30(6): 931-936.
[15]	ZHANG Xiaoyi, DENG Dongjie, TAN Jianjun, HE Yu, LI Chunhua, WANG Cunxin. Pharmacophore and Docking-based 3D-QSAR Studies on HIV-1 Integrase Inhibitors[J]. 高等学校化学研究, 2014, 30(2): 297-305.