Citation: Yu Fei, Wang Qi, Wang Han, Si Long-Long, Liu Jia-Xin, Han Xu, Xiao Su-Long, Zhang Li-He, Zhou De-Min. Synthesis and biological evaluation of echinocystic acid derivatives as HCV entry inhibitors[J]. Chinese Chemical Letters, ;2016, 27(5): 711-713. doi: 10.1016/j.cclet.2016.01.050 shu

Synthesis and biological evaluation of echinocystic acid derivatives as HCV entry inhibitors

Yu Fei ^a,, ,
Wang Qi ^b ,
Wang Han ^b ,
Si Long-Long ^b ,
Liu Jia-Xin ^a ,
Han Xu ^b ,
Xiao Su-Long ^b ,
Zhang Li-He ^b ,
Zhou De-Min ^b,,

a.
Medical Faculty of Kunming University of Science and Technology, Kunming 650500, China
b.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China

Corresponding author: Yu Fei, feiyuz8@163.com Zhou De-Min, deminzhou@bjmu.edu.cn
Received Date: 26 June 2015
Revised Date: 14 December 2015
Accepted Date: 23 January 2016
Available Online: 6 May 2016

Figures(4)

A series of echinocystic acid (EA) 28-COOH derivatives was synthesized, and their anti-HCV entry activity was evaluated by HCVpp and VSVpp entry assay. It was found that some of them showed moderate anti-HCV entry activity, especially compound 12, and these modifications also removed the undesired hemolytic effect.
- Triterpene,
- Echinocystic acid,
- HCV entry inhibitors,
- Hemolysis
1. [1]
  Sy T., Jamal M.M.. Epidemiology of hepatitis C virus (HCV) infection[J]. Int. J. Med. Sci., 2006,3:41-46.
2. [2]
  Shepard C.W., Finelli L., Alter M.J.. Global epidemiology of hepatitis C virus infection[J]. Lancet Infect. Dis., 2005,5:558-567.
3. [3]
  Sheridan C.. New Merck and Vertex drugs raise standard of care in hepatitis C[J]. Nat. Biotechnol., 2011,29:553-554.
4. [4]
  Fried M., Shiffman M., Reddy K.. Peginterferon alfa-2a plus ribavirin for chronic hepatitis C virus infection[J]. New Engl. J. Med., 2002,347:975-982.
5. [5]
  Di Bisceglie A.M., McHutchison J., Rice C.M.. New therapeutic strategies for hepatitis C[J]. Hepatology, 2002,35:224-231.
6. [6]
  Thompson A., McHutchison J.. Antiviral resistance and specifically targeted therapy for HCV (STAT-C)[J]. J. Viral Hepatitis, 2009,16:377-387.
7. [7]
  Wong-Staal F., Syder A.J., McKelvy J.F.. Targeting HCV entry for development of therapeutics[J]. Viruses, 2010,2:1718-1733.
8. [8]
  Yu F., Wang Q., Zhang Z.. Development of oleanane-type triterpenes as a new class of HCV nntry inhibitors[J]. J. Med. Chem., 2013,56:4300-4319.
9. [9]
  Mittapalli G.K., Jackson A., Zhao F.. Discovery of highly potent small molecule hepatitis C virus entry inhibitors[J]. Bioorg. Med. Chem. Lett., 2011,21:6852-6855.
10. [10]
  Yu F., Peng Y., Wang Q.. Development of bivalent oleanane-type triterpenes as potent HCV entry inhibitors[J]. Eur. J. Med. Chem., 2014,77:258-268.
11. [11]
  Wang H., Wang Q., Xiao S.. Elucidation of the pharmacophore of echinocystic acid, a new lead for blocking HCV entry[J]. Eur. J. Med. Chem., 2013,64:160-168.
12. [12]
  Yang J., Zhou D., Wong-Staal F.. Screening of small-molecule compounds as inhibitors of HCV entry[J]. Meth. Mol. Biol., 2009,510:295-304.
13. [13]
  Bartosch B., Dubuisson J., Cosset F.. Infectious hepatitis C virus pseudo-particles containing functional E1-E2 envelope protein complexes[J]. J. Exp. Med., 2003,197:633-642.
14. [14]
  Hsu M., Zhang J., Flint M.. Hepatitis C virus glycoproteins mediate pHdependent cell entry of pseudotyped retroviral particles[J]. Proc. Natl. Acad. Sci. U.S.A., 2003,100:7271-7276.
15. [15]
  Francis G., Kerem Z., Makkar H.P.. The biological action of saponins in animal systems:a review[J]. Br. J. Nutr., 2002,88:587-605.
1. [1]
  Yaping Zhang , Wei Zhou , Mingchun Gao , Tianqi Liu , Bingxin Liu , Chang-Hua Ding , Bin Xu . Oxidative cyclization of allyl compounds and isocyanide: A facile entry to polysubstituted 2-cyanopyrroles. Chinese Chemical Letters, 2024, 35(4): 108836-. doi: 10.1016/j.cclet.2023.108836
2. [2]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
3. [3]
  Mianling Yang , Meehyein Kim , Peng Zhan . Modular miniaturized synthesis and in situ biological evaluation facilitate rapid discovery of potent MraY inhibitors as antibacterial agents. Chinese Chemical Letters, 2025, 36(2): 110455-. doi: 10.1016/j.cclet.2024.110455
4. [4]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
5. [5]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
6. [6]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
7. [7]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
8. [8]
  Jian Song , Shenghui Wang , Qiuge Liu , Xiao Wang , Shuo Yuan , Hongmin Liu , Saiyang Zhang . N-Benzyl arylamide derivatives as novel and potent tubulin polymerization inhibitors against gastric cancers: Design, structure–activity relationships and biological evaluations. Chinese Chemical Letters, 2025, 36(2): 109678-. doi: 10.1016/j.cclet.2024.109678
9. [9]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
10. [10]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089
11. [11]
  Linshan Peng , Qihang Peng , Tianxiang Jin , Zhirong Liu , Yong Qian . Highly efficient capture of thorium ion by citric acid-modified chitosan gels from aqueous solution. Chinese Chemical Letters, 2024, 35(5): 108891-. doi: 10.1016/j.cclet.2023.108891
12. [12]
  Yingying Yan , Wanhe Jia , Rui Cai , Chun Liu . An AIPE-active fluorinated cationic Pt(Ⅱ) complex for efficient detection of picric acid in aqueous media. Chinese Chemical Letters, 2024, 35(5): 108819-. doi: 10.1016/j.cclet.2023.108819
13. [13]
  Fengyun Li , Zerong Pei , Shuting Chen , Gen li , Mengyang Liu , Liqin Ding , Jingbo Liu , Feng Qiu . Multifunctional nano-herb based on tumor microenvironment for enhanced tumor therapy of gambogic acid. Chinese Chemical Letters, 2024, 35(5): 108752-. doi: 10.1016/j.cclet.2023.108752
14. [14]
  Zhen Liu , Zhi-Yuan Ren , Chen Yang , Xiangyi Shao , Li Chen , Xin Li . Asymmetric alkenylation reaction of benzoxazinones with diarylethylenes catalyzed by B(C₆F₅)₃/chiral phosphoric acid. Chinese Chemical Letters, 2024, 35(5): 108939-. doi: 10.1016/j.cclet.2023.108939
15. [15]
  Peizhe Li , Qiaoling Liu , Mengyu Pei , Yuci Gan , Yan Gong , Chuchen Gong , Pei Wang , Mingsong Wang , Xiansong Wang , Da-Peng Yang , Bo Liang , Guangyu Ji . Chlorogenic acid supported strontium polyphenol networks ensemble microneedle patch to promote diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109457-. doi: 10.1016/j.cclet.2023.109457
16. [16]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
17. [17]
  Shiyu Pan , Bo Cao , Deling Yuan , Tifeng Jiao , Qingrui Zhang , Shoufeng Tang . Complexes of cupric ion and tartaric acid enhanced calcium peroxide Fenton-like reaction for metronidazole degradation. Chinese Chemical Letters, 2024, 35(7): 109185-. doi: 10.1016/j.cclet.2023.109185
18. [18]
  Xubin Qian , Lei Xu , Xu Ge , Zhun Liu , Cheng Fang , Jianbing Wang , Junfeng Niu . Can perfluorooctanoic acid be effectively degraded using β-PbO₂ reactive electrochemical membrane?. Chinese Chemical Letters, 2024, 35(7): 109218-. doi: 10.1016/j.cclet.2023.109218
19. [19]
  Xinyue Lan , Junguang Liang , Churan Wen , Xiaolong Quan , Huimin Lin , Qinqin Xu , Peixian Chen , Guangyu Yao , Dan Zhou , Meng Yu . Photo-manipulated polyunsaturated fatty acid-doped liposomal hydrogel for flexible photoimmunotherapy. Chinese Chemical Letters, 2024, 35(4): 108616-. doi: 10.1016/j.cclet.2023.108616
20. [20]
  Dexuan Xiao , Tianyu Chen , Tianxu Zhang , Sirong Shi , Mei Zhang , Xin Qin , Yunkun Liu , Longjiang Li , Yunfeng Lin . Transdermal treatment for malignant melanoma by aptamer-modified tetrahedral framework nucleic acid delivery of vemurafenib. Chinese Chemical Letters, 2024, 35(4): 108602-. doi: 10.1016/j.cclet.2023.108602

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(621)
HTML views(6)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142