Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
Identifieur interne : 001203 ( PubMed/Corpus ); précédent : 001202; suivant : 001204Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.
Auteurs : Ji-Young Park ; 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.
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
Links to Exploration step
pubmed:23647823Le document en format XML
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Jae" last="Jeong">Hyung Jae Jeong</name></author><author><name sortKey="Kim, Young Min" sort="Kim, Young Min" uniqKey="Kim Y" first="Young Min" last="Kim">Young Min Kim</name></author><author><name sortKey="Kim, Doman" sort="Kim, Doman" uniqKey="Kim D" first="Doman" last="Kim">Doman Kim</name></author><author><name sortKey="Lee, Woo Song" sort="Lee, Woo Song" uniqKey="Lee W" first="Woo Song" last="Lee">Woo Song Lee</name></author><author><name sortKey="Ryu, Young Bae" sort="Ryu, Young Bae" uniqKey="Ryu Y" first="Young Bae" last="Ryu">Young Bae Ryu</name></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2013">2013</date><idno type="RBID">pubmed:23647823</idno><idno type="pmid">23647823</idno><idno type="doi">10.1016/j.bmc.2013.04.026</idno><idno type="wicri:Area/PubMed/Corpus">001203</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" 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Hyung Jae" uniqKey="Jeong H" first="Hyung Jae" last="Jeong">Hyung Jae Jeong</name></author><author><name sortKey="Kim, Young Min" sort="Kim, Young Min" uniqKey="Kim Y" first="Young Min" last="Kim">Young Min Kim</name></author><author><name sortKey="Kim, Doman" sort="Kim, Doman" uniqKey="Kim D" first="Doman" last="Kim">Doman Kim</name></author><author><name sortKey="Lee, Woo Song" sort="Lee, Woo Song" uniqKey="Lee W" first="Woo Song" last="Lee">Woo Song Lee</name></author><author><name sortKey="Ryu, Young Bae" sort="Ryu, Young Bae" uniqKey="Ryu Y" first="Young Bae" last="Ryu">Young Bae Ryu</name></author></analytic><series><title level="j">Bioorganic & medicinal chemistry</title><idno type="eISSN">1464-3391</idno><imprint><date when="2013" type="published">2013</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (isolation & purification)</term><term>Antiviral Agents (pharmacology)</term><term>Benzofurans (chemistry)</term><term>Benzofurans (isolation & purification)</term><term>Benzofurans (pharmacology)</term><term>Cysteine Proteases (metabolism)</term><term>Cysteine Proteinase Inhibitors (chemistry)</term><term>Cysteine Proteinase Inhibitors (isolation & purification)</term><term>Cysteine Proteinase Inhibitors (pharmacology)</term><term>Humans</term><term>Molecular Docking Simulation</term><term>Phaeophyta (chemistry)</term><term>Quantitative Structure-Activity Relationship</term><term>SARS Virus (drug effects)</term><term>SARS Virus (enzymology)</term><term>Severe Acute Respiratory Syndrome (drug therapy)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Benzofurans</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="isolation & purification" xml:lang="en"><term>Antiviral Agents</term><term>Benzofurans</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cysteine Proteases</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Benzofurans</term><term>Cysteine Proteinase Inhibitors</term></keywords><keywords scheme="MESH" qualifier="chemistry" xml:lang="en"><term>Phaeophyta</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" qualifier="drug therapy" xml:lang="en"><term>Severe Acute Respiratory Syndrome</term></keywords><keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Humans</term><term>Molecular Docking Simulation</term><term>Quantitative Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><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></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">23647823</PMID><DateCompleted><Year>2013</Year><Month>12</Month><Day>16</Day></DateCompleted><DateRevised><Year>2020</Year><Month>04</Month><Day>09</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1464-3391</ISSN><JournalIssue CitedMedium="Internet"><Volume>21</Volume><Issue>13</Issue><PubDate><Year>2013</Year><Month>Jul</Month><Day>01</Day></PubDate></JournalIssue><Title>Bioorganic & medicinal chemistry</Title><ISOAbbreviation>Bioorg. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Dieckol, a SARS-CoV 3CL(pro) inhibitor, isolated from the edible brown algae Ecklonia cava.</ArticleTitle><Pagination><MedlinePgn>3730-7</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.bmc.2013.04.026</ELocationID><ELocationID EIdType="pii" ValidYN="Y">S0968-0896(13)00352-0</ELocationID><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></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Park</LastName><ForeName>Ji-Young</ForeName><Initials>JY</Initials><AffiliationInfo><Affiliation>Infection Control Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup 580-185, Republic of Korea.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Jang Hoon</ForeName><Initials>JH</Initials></Author><Author ValidYN="Y"><LastName>Kwon</LastName><ForeName>Jung Min</ForeName><Initials>JM</Initials></Author><Author ValidYN="Y"><LastName>Kwon</LastName><ForeName>Hyung-Jun</ForeName><Initials>HJ</Initials></Author><Author ValidYN="Y"><LastName>Jeong</LastName><ForeName>Hyung Jae</ForeName><Initials>HJ</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Young Min</ForeName><Initials>YM</Initials></Author><Author ValidYN="Y"><LastName>Kim</LastName><ForeName>Doman</ForeName><Initials>D</Initials></Author><Author ValidYN="Y"><LastName>Lee</LastName><ForeName>Woo Song</ForeName><Initials>WS</Initials></Author><Author ValidYN="Y"><LastName>Ryu</LastName><ForeName>Young Bae</ForeName><Initials>YB</Initials></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType><PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2013</Year><Month>04</Month><Day>22</Day></ArticleDate></Article><MedlineJournalInfo><Country>England</Country><MedlineTA>Bioorg Med Chem</MedlineTA><NlmUniqueID>9413298</NlmUniqueID><ISSNLinking>0968-0896</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance 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