Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.
Identifieur interne : 000E34 ( PubMed/Curation ); précédent : 000E33; suivant : 000E35Design, synthesis, biological evaluation and molecular docking studies of phenylpropanoid derivatives as potent anti-hepatitis B virus agents.
Auteurs : Sheng Liu [République populaire de Chine] ; Wanxing Wei [République populaire de Chine] ; Yubin Li [République populaire de Chine] ; Xu Liu [République populaire de Chine] ; Xiaoji Cao [République populaire de Chine] ; Kechan Lei [République populaire de Chine] ; Min Zhou [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2015.
Descripteurs français
- KwdFr :
- Antigènes HLA-A (), Antigènes HLA-A (métabolisme), Antigènes de surface du virus de l'hépatite B (métabolisme), Antigènes e du virus de l'hépatite virale B (métabolisme), Antiviraux (), Antiviraux (métabolisme), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Cellules HepG2, Conception de médicament, Domaine catalytique, Humains, Phénols (), Phénols (métabolisme), Phénols (pharmacologie), Phénols (synthèse chimique), Relation quantitative structure-activité, Réplication de l'ADN (), Réplication virale (), Simulation de docking moléculaire, Techniques de chimie synthétique, Virus de l'hépatite B (), Virus de l'hépatite B (métabolisme), Virus de l'hépatite B (physiologie).
- MESH :
- métabolisme : Antigènes HLA-A, Antigènes de surface du virus de l'hépatite B, Antigènes e du virus de l'hépatite virale B, Antiviraux, Phénols, Virus de l'hépatite B.
- pharmacologie : Antiviraux, Phénols.
- physiologie : Virus de l'hépatite B.
- synthèse chimique : Antiviraux, Phénols.
- Antigènes HLA-A, Antiviraux, Cellules HepG2, Conception de médicament, Domaine catalytique, Humains, Phénols, Relation quantitative structure-activité, Réplication de l'ADN, Réplication virale, Simulation de docking moléculaire, Techniques de chimie synthétique, Virus de l'hépatite B.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (metabolism), Antiviral Agents (pharmacology), Catalytic Domain, Chemistry Techniques, Synthetic, DNA Replication (drug effects), Drug Design, HLA-A Antigens (chemistry), HLA-A Antigens (metabolism), Hep G2 Cells, Hepatitis B Surface Antigens (metabolism), Hepatitis B e Antigens (metabolism), Hepatitis B virus (drug effects), Hepatitis B virus (metabolism), Hepatitis B virus (physiology), Humans, Molecular Docking Simulation, Phenols (chemical synthesis), Phenols (chemistry), Phenols (metabolism), Phenols (pharmacology), Quantitative Structure-Activity Relationship, Virus Replication (drug effects).
- MESH :
- chemical , chemical synthesis : Antiviral Agents, Phenols.
- chemical , chemistry : Antiviral Agents, HLA-A Antigens, Phenols.
- chemical , metabolism : Antiviral Agents, HLA-A Antigens, Hepatitis B Surface Antigens, Hepatitis B e Antigens, Phenols.
- chemical , pharmacology : Antiviral Agents, Phenols.
- drug effects : DNA Replication, Hepatitis B virus, Virus Replication.
- metabolism : Hepatitis B virus.
- physiology : Hepatitis B virus.
- Catalytic Domain, Chemistry Techniques, Synthetic, Drug Design, Hep G2 Cells, Humans, Molecular Docking Simulation, Quantitative Structure-Activity Relationship.
Abstract
A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structure-activity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents.
DOI: 10.1016/j.ejmech.2015.03.056
PubMed: 25847765
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<front><div type="abstract" xml:lang="en">A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structure-activity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents. </div>
</front>
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<Abstract><AbstractText>A series of phenylpropanoid derivatives were synthesized, and their anti-hepatitis B virus (HBV) activity was evaluated in HepG 2.2.15 cells. Most of the synthesized derivatives showed effective anti-HBV activity. Of these compounds, compound 4c-1 showed the most potent anti-HBV activity, demonstrating potent inhibitory effect not only on the secretion of HBsAg (IC50 = 14.18 μM, SI = 17.85) and HBeAg (IC50 = 6.20 μM, SI = 40.82) secretion but also HBV DNA replication (IC50 = 23.43 μM, SI = 10.80). The structure-activity relationships (SARs) of phenylpropanoid derivatives had been discussed, which were useful for phenylpropanoid derivatives to be explored and developed as novel anti-HBV agents. Moreover, the docking study of all synthesized compounds inside the HLA-A protein (PDB ID: 3OX8) active site were carried out to explore the molecular interactions and a molecular target for activity of phenylpropanoid derivatives with the protein using a moe-docking technique. This study identified a new class of potent anti-HBV agents. </AbstractText>
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<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
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<MeshHeading><DescriptorName UI="D006513" MajorTopicYN="N">Hepatitis B e Antigens</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
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<MeshHeading><DescriptorName UI="D006515" MajorTopicYN="N">Hepatitis B virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
<QualifierName UI="Q000502" MajorTopicYN="N">physiology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName>
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<MeshHeading><DescriptorName UI="D062105" MajorTopicYN="N">Molecular Docking Simulation</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D010636" MajorTopicYN="N">Phenols</DescriptorName>
<QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D021281" MajorTopicYN="N">Quantitative Structure-Activity Relationship</DescriptorName>
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<MeshHeading><DescriptorName UI="D014779" MajorTopicYN="N">Virus Replication</DescriptorName>
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<KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Anti-HBV activity</Keyword>
<Keyword MajorTopicYN="N">Molecular docking</Keyword>
<Keyword MajorTopicYN="N">Phenylpropanoid derivatives</Keyword>
<Keyword MajorTopicYN="N">Structure–activity relationships</Keyword>
<Keyword MajorTopicYN="N">Synthesis</Keyword>
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<PubmedData><History><PubMedPubDate PubStatus="received"><Year>2014</Year>
<Month>11</Month>
<Day>05</Day>
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<PubMedPubDate PubStatus="revised"><Year>2015</Year>
<Month>03</Month>
<Day>24</Day>
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<PubMedPubDate PubStatus="accepted"><Year>2015</Year>
<Month>03</Month>
<Day>25</Day>
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<Day>8</Day>
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<PubMedPubDate PubStatus="medline"><Year>2016</Year>
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<ArticleId IdType="pii">S0223-5234(15)00223-8</ArticleId>
<ArticleId IdType="doi">10.1016/j.ejmech.2015.03.056</ArticleId>
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