Novel anilinocoumarin derivatives as agents against hepatitis C virus by the induction of IFN-mediated antiviral responses

Huang-Kai Peng; Wei-Chun Chen; Jin-Ching Lee; Shiang-Yu Yang; Cherng-Chyi Tzeng; Ying-Ting Lin; Shyh-Chyun Yang

doi:10.1039/C2OB26860D

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Organic & Biomolecular Chemistry

Issue 11, 2013

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Novel anilinocoumarin derivatives as agents against hepatitis C virus by the induction of IFN-mediated antiviral responses

Huang-Kai Peng,^a Wei-Chun Chen,^b Jin-Ching Lee,^b Shiang-Yu Yang,^c Cherng-Chyi Tzeng,^d Ying-Ting Lin*^b and Shyh-Chyun Yang*^a^e

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School of Pharmacy, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
E-mail: scyang@kmu.edu.tw ;
Fax: +886 7 3210683 ;
Tel: +886 7 3121101 ext 2662

Department of Biotechnology, College of Life Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan
E-mail: ytlin@kmu.edu.tw

School of Medicine, College of Medicine, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Department of Medicinal and Applied Chemistry, College of Life Science, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Department of Fragrance and Cosmetic Science, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan

Org. Biomol. Chem., 2013,11, 1858-1866

DOI: 10.1039/C2OB26860D
Received 21 Sep 2012, Accepted 04 Jan 2013
First published online 01 Feb 2013

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The hepatitis C virus (HCV) is the main cause of progressive liver disease, leading to the development of liver cirrhosis and hepatocellular carcinoma (HCC). Novel anilinocoumarins were synthesized, and their efficacy against HCV replication was evaluated. We demonstrated that 3-(3′,4′,5′-trimethoxyanilin-1′-yl)methylaminocoumarin (6) exhibited strong anti-HCV activity at protein and RNA levels at non-toxic concentrations, with an EC₅₀ value of 12 ± 0.3 μM and a selective index (SI) value of 10. Combined treatment of compound 6 and interferon-α (IFN) or telaprevir induced a significant decrease in HCV RNA levels, respectively. We also found that the anti-HCV replication effect of compound 6 was due to the induction of IFN-mediated antiviral responses. This is the first report demonstrating that coumarins inhibit viral replication through an IFN-mediated anti-viral response. Collectively, compound 6 possessed potent activities against HCV replication and could be a new lead compound with higher selectivity and less toxicity.

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Huang-Kai Peng
Wei-Chun Chen
Jin-Ching Lee
Shiang-Yu Yang
Cherng-Chyi Tzeng
Ying-Ting Lin
Shyh-Chyun Yang

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