Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
Identifieur interne : 001203 ( PubMed/Curation ); précédent : 001202; suivant : 001204Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
Auteurs : Ji-Young Park [Corée du Sud] ; Jang Hoon Kim ; Jung Min Kwon ; Hyung-Jun Kwon ; Hyung Jae Jeong ; Young Min Kim ; Doman Kim ; Woo Song Lee ; Young Bae RyuSource :
- Bioorganic & medicinal chemistry [ 1464-3391 ] ; 2013.
Descripteurs français
- KwdFr :
- Antiviraux (), Antiviraux (isolement et purification), Antiviraux (pharmacologie), Benzofuranes (), Benzofuranes (isolement et purification), Benzofuranes (pharmacologie), Cysteine proteases (métabolisme), Humains, Inhibiteurs de la cystéine protéinase (), Inhibiteurs de la cystéine protéinase (isolement et purification), Inhibiteurs de la cystéine protéinase (pharmacologie), Phaeophyta (), Relation quantitative structure-activité, Simulation de docking moléculaire, Syndrome respiratoire aigu sévère (traitement médicamenteux), Virus du SRAS (), Virus du SRAS (enzymologie).
- MESH :
- enzymologie : Virus du SRAS.
- isolement et purification : Antiviraux, Benzofuranes, Inhibiteurs de la cystéine protéinase.
- métabolisme : Cysteine proteases.
- pharmacologie : Antiviraux, Benzofuranes, Inhibiteurs de la cystéine protéinase.
- traitement médicamenteux : Syndrome respiratoire aigu sévère.
- Antiviraux, Benzofuranes, Humains, Inhibiteurs de la cystéine protéinase, Phaeophyta, Relation quantitative structure-activité, Simulation de docking moléculaire, Virus du SRAS.
English descriptors
- KwdEn :
- Antiviral Agents (chemistry), Antiviral Agents (isolation & purification), Antiviral Agents (pharmacology), Benzofurans (chemistry), Benzofurans (isolation & purification), Benzofurans (pharmacology), Cysteine Proteases (metabolism), Cysteine Proteinase Inhibitors (chemistry), Cysteine Proteinase Inhibitors (isolation & purification), Cysteine Proteinase Inhibitors (pharmacology), Humans, Molecular Docking Simulation, Phaeophyta (chemistry), Quantitative Structure-Activity Relationship, SARS Virus (drug effects), SARS Virus (enzymology), Severe Acute Respiratory Syndrome (drug therapy).
- MESH :
- chemical , chemistry : Antiviral Agents, Benzofurans, Cysteine Proteinase Inhibitors.
- chemical , isolation & purification : Antiviral Agents, Benzofurans, Cysteine Proteinase Inhibitors.
- chemical , metabolism : Cysteine Proteases.
- chemical , pharmacology : Antiviral Agents, Benzofurans, Cysteine Proteinase Inhibitors.
- chemistry : Phaeophyta.
- drug effects : SARS Virus.
- drug therapy : Severe Acute Respiratory Syndrome.
- enzymology : SARS Virus.
- Humans, Molecular Docking Simulation, Quantitative Structure-Activity Relationship.
Abstract
SARS-CoV 3CL(pro) plays an important role in viral replication. In this study, we performed a biological evaluation on nine phlorotannins isolated from the edible brown algae Ecklonia cava. The nine isolated phlorotannins (1-9), except phloroglucinol (1), possessed SARS-CoV 3CL(pro) inhibitory activities in a dose-dependently and competitive manner. Of these phlorotannins (1-9), two eckol groups with a diphenyl ether linked dieckol (8) showed the most potent SARS-CoV 3CL(pro) trans/cis-cleavage inhibitory effects (IC(50)s = 2.7 and 68.1 μM, respectively). This is the first report of a (8) phlorotannin chemotype significantly blocking the cleavage of SARS-CoV 3CL(pro) in a cell-based assay with no toxicity. Furthermore, dieckol (8) exhibited a high association rate in the SPR sensorgram and formed extremely strong hydrogen bonds to the catalytic dyad (Cys145 and His41) of the SARS-CoV 3CL(pro).
DOI: 10.1016/j.bmc.2013.04.026
PubMed: 23647823
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pubmed:23647823Le document en format XML
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<front><div type="abstract" xml:lang="en">SARS-CoV 3CL(pro) plays an important role in viral replication. In this study, we performed a biological evaluation on nine phlorotannins isolated from the edible brown algae Ecklonia cava. The nine isolated phlorotannins (1-9), except phloroglucinol (1), possessed SARS-CoV 3CL(pro) inhibitory activities in a dose-dependently and competitive manner. Of these phlorotannins (1-9), two eckol groups with a diphenyl ether linked dieckol (8) showed the most potent SARS-CoV 3CL(pro) trans/cis-cleavage inhibitory effects (IC(50)s = 2.7 and 68.1 μM, respectively). This is the first report of a (8) phlorotannin chemotype significantly blocking the cleavage of SARS-CoV 3CL(pro) in a cell-based assay with no toxicity. Furthermore, dieckol (8) exhibited a high association rate in the SPR sensorgram and formed extremely strong hydrogen bonds to the catalytic dyad (Cys145 and His41) of the SARS-CoV 3CL(pro).</div>
</front>
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<ArticleTitle>Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.</ArticleTitle>
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<Abstract><AbstractText>SARS-CoV 3CL(pro) plays an important role in viral replication. In this study, we performed a biological evaluation on nine phlorotannins isolated from the edible brown algae Ecklonia cava. The nine isolated phlorotannins (1-9), except phloroglucinol (1), possessed SARS-CoV 3CL(pro) inhibitory activities in a dose-dependently and competitive manner. Of these phlorotannins (1-9), two eckol groups with a diphenyl ether linked dieckol (8) showed the most potent SARS-CoV 3CL(pro) trans/cis-cleavage inhibitory effects (IC(50)s = 2.7 and 68.1 μM, respectively). This is the first report of a (8) phlorotannin chemotype significantly blocking the cleavage of SARS-CoV 3CL(pro) in a cell-based assay with no toxicity. Furthermore, dieckol (8) exhibited a high association rate in the SPR sensorgram and formed extremely strong hydrogen bonds to the catalytic dyad (Cys145 and His41) of the SARS-CoV 3CL(pro).</AbstractText>
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<ForeName>Ji-Young</ForeName>
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<ForeName>Jang Hoon</ForeName>
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<Author ValidYN="Y"><LastName>Kwon</LastName>
<ForeName>Jung Min</ForeName>
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<Author ValidYN="Y"><LastName>Kwon</LastName>
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<Author ValidYN="Y"><LastName>Lee</LastName>
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