Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents

Tsurng Juhn Huang; Hong Chuang; Yu Chuan Liang; Hui Hsien Lin; Jia Cherng Horng; Yu Cheng Kuo; Chia Wen Chen; Fu Yuan Tsai; Shih Chieh Yen; Shih Ching Chou; Ming Hua Hsu

doi:10.1016/j.ejmech.2014.11.050

Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents

Tsurng Juhn Huang, Hong Chuang, Yu Chuan Liang, Hui Hsien Lin, Jia Cherng Horng, Yu Cheng Kuo, Chia Wen Chen, Fu Yuan Tsai, Shih Chieh Yen, Shih Ching Chou, Ming Hua Hsu^*

^*Corresponding author for this work

Center for General Education

Research output: Contribution to journal › Journal Article › peer-review

37 Scopus citations

Abstract

Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-α and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC₅₀ value of 0.36 μM, and high selectivity index, SI (TC₅₀/IC₅₀) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development.

Original language	English
Pages (from-to)	428-435
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	90
DOIs	https://doi.org/10.1016/j.ejmech.2014.11.050
State	Published - 27 01 2015

Bibliographical note

Publisher Copyright:
© 2014 Elsevier Masson SAS.

Keywords

Anti-HBV agent
HBV
Hepatitis B virus
Paeonol
Phenylsulfonyl group

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.ejmech.2014.11.050

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title = "Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents",

abstract = "Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-α and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC50 value of 0.36 μM, and high selectivity index, SI (TC50/IC50) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development.",

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doi = "10.1016/j.ejmech.2014.11.050",

language = "英语",

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T1 - Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents

AU - Huang, Tsurng Juhn

AU - Chuang, Hong

AU - Liang, Yu Chuan

AU - Lin, Hui Hsien

AU - Horng, Jia Cherng

AU - Kuo, Yu Cheng

AU - Chen, Chia Wen

AU - Tsai, Fu Yuan

AU - Yen, Shih Chieh

AU - Chou, Shih Ching

AU - Hsu, Ming Hua

PY - 2015/1/27

Y1 - 2015/1/27

N2 - Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-α and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC50 value of 0.36 μM, and high selectivity index, SI (TC50/IC50) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development.

AB - Hepatitis B virus (HBV) is a causative reagent that frequently causes progressive liver diseases, leading to the development of acute, chronic hepatitis, cirrhosis, and eventually hepatocellular carcinoma (HCC). Despite several antiviral drugs including interferon-α and nucleotide derivatives are approved for clinical treatment for HBV, critical issues remain unresolved, e.g., low-to-moderate efficacy, adverse side effects, and resistant strains. In this study, novel Paeonol-phenylsulfonyl derivatives were synthesized and their antiviral effect against HBV was evaluated. The experimental results indicated that these compounds process significant antiviral potential, including the inhibition of viral antigen expression and secretion, and the suppression of HBV viral DNA replication. Among compounds synthesized in this research, compound 2-acetyl-5-methoxyphenyl 4-methoxybenzenesulfonate (7f) had the most potent inhibitory activity with IC50 value of 0.36 μM, and high selectivity index, SI (TC50/IC50) 47.75; which exhibited an apparent inhibition effect on viral gene expression and viral propagation in cell culture model. So, we believe our compounds could serve as reservoir for antiviral drug development.

KW - Anti-HBV agent

KW - HBV

KW - Hepatitis B virus

KW - Paeonol

KW - Phenylsulfonyl group

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ER -

Design, synthesis, and bioevaluation of paeonol derivatives as potential anti-HBV agents

Abstract

Bibliographical note

Keywords

UN SDGs

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