Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease.
Identifieur interne : 002741 ( PubMed/Checkpoint ); précédent : 002740; suivant : 002742Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease.
Auteurs : Jiun-Jie Shie [Taïwan] ; Jim-Min Fang ; Chih-Jung Kuo ; Tun-Hsun Kuo ; Po-Huang Liang ; Hung-Jyun Huang ; Wen-Bin Yang ; Chun-Hung Lin ; Jiun-Ling Chen ; Yin-Ta Wu ; Chi-Huey WongSource :
- Journal of medicinal chemistry [ 0022-2623 ] ; 2005.
Descripteurs français
- KwdFr :
- Anilides (), Anilides (pharmacologie), Anilides (synthèse chimique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Cinétique, Conformation des protéines, Cysteine endopeptidases, Endopeptidases (), Endopeptidases (métabolisme), Inhibiteurs de protéases (), Inhibiteurs de protéases (pharmacologie), Inhibiteurs de protéases (synthèse chimique), Modèles moléculaires, Protéines virales (), Protéines virales (métabolisme), Relation structure-activité, Syndrome respiratoire aigu sévère (traitement médicamenteux), Virus du SRAS (), Virus du SRAS (enzymologie).
- MESH :
- enzymologie : Virus du SRAS.
- métabolisme : Endopeptidases, Protéines virales.
- pharmacologie : Anilides, Antiviraux, Inhibiteurs de protéases.
- synthèse chimique : Anilides, Antiviraux, Inhibiteurs de protéases.
- traitement médicamenteux : Syndrome respiratoire aigu sévère.
- Anilides, Antiviraux, Cinétique, Conformation des protéines, Cysteine endopeptidases, Endopeptidases, Inhibiteurs de protéases, Modèles moléculaires, Protéines virales, Relation structure-activité, Virus du SRAS.
English descriptors
- KwdEn :
- Anilides (chemical synthesis), Anilides (chemistry), Anilides (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cysteine Endopeptidases, Endopeptidases (chemistry), Endopeptidases (drug effects), Endopeptidases (metabolism), Kinetics, Models, Molecular, Protease Inhibitors (chemical synthesis), Protease Inhibitors (chemistry), Protease Inhibitors (pharmacology), Protein Conformation, SARS Virus (drug effects), SARS Virus (enzymology), Severe Acute Respiratory Syndrome (drug therapy), Structure-Activity Relationship, Viral Proteins (chemistry), Viral Proteins (drug effects), Viral Proteins (metabolism).
- MESH :
- chemical , chemical synthesis : Anilides, Antiviral Agents, Protease Inhibitors.
- chemical , chemistry : Anilides, Antiviral Agents, Endopeptidases, Protease Inhibitors, Viral Proteins.
- chemical , drug effects : Endopeptidases, Viral Proteins.
- chemical , metabolism : Endopeptidases, Viral Proteins.
- chemical , pharmacology : Anilides, Antiviral Agents, Protease Inhibitors.
- chemical : Cysteine Endopeptidases.
- drug effects : SARS Virus.
- drug therapy : Severe Acute Respiratory Syndrome.
- enzymology : SARS Virus.
- Kinetics, Models, Molecular, Protein Conformation, Structure-Activity Relationship.
Abstract
A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, l-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K(i) = 0.03 muM. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.
DOI: 10.1021/jm050184y
PubMed: 15974598
Affiliations:
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pubmed:15974598Le document en format XML
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xml:lang="fr"><term>Anilides</term><term>Antiviraux</term><term>Cinétique</term><term>Conformation des protéines</term><term>Cysteine endopeptidases</term><term>Endopeptidases</term><term>Inhibiteurs de protéases</term><term>Modèles moléculaires</term><term>Protéines virales</term><term>Relation structure-activité</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, l-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K(i) = 0.03 muM. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">15974598</PMID><DateCompleted><Year>2005</Year><Month>08</Month><Day>23</Day></DateCompleted><DateRevised><Year>2020</Year><Month>03</Month><Day>25</Day></DateRevised><Article PubModel="Print"><Journal><ISSN IssnType="Print">0022-2623</ISSN><JournalIssue CitedMedium="Print"><Volume>48</Volume><Issue>13</Issue><PubDate><Year>2005</Year><Month>Jun</Month><Day>30</Day></PubDate></JournalIssue><Title>Journal of medicinal chemistry</Title><ISOAbbreviation>J. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>Discovery of potent anilide inhibitors against the severe acute respiratory syndrome 3CL protease.</ArticleTitle><Pagination><MedlinePgn>4469-73</MedlinePgn></Pagination><Abstract><AbstractText>A diversified library of peptide anilides was prepared, and their inhibition activities against the SARS-CoV 3CL protease were examined by a fluorogenic tetradecapeptide substrate. The most potent inhibitor is an anilide derived from 2-chloro-4-nitroaniline, l-phenylalanine and 4-(dimethylamino)benzoic acid. This anilide is a competitive inhibitor of the SARS-CoV 3CL protease with K(i) = 0.03 muM. The molecular docking experiment indicates that the P1 residue of this anilide inhibitor is distant from the nucleophilic SH of Cys145 in the active site.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Shie</LastName><ForeName>Jiun-Jie</ForeName><Initials>JJ</Initials><AffiliationInfo><Affiliation>Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Fang</LastName><ForeName>Jim-Min</ForeName><Initials>JM</Initials></Author><Author ValidYN="Y"><LastName>Kuo</LastName><ForeName>Chih-Jung</ForeName><Initials>CJ</Initials></Author><Author ValidYN="Y"><LastName>Kuo</LastName><ForeName>Tun-Hsun</ForeName><Initials>TH</Initials></Author><Author ValidYN="Y"><LastName>Liang</LastName><ForeName>Po-Huang</ForeName><Initials>PH</Initials></Author><Author ValidYN="Y"><LastName>Huang</LastName><ForeName>Hung-Jyun</ForeName><Initials>HJ</Initials></Author><Author ValidYN="Y"><LastName>Yang</LastName><ForeName>Wen-Bin</ForeName><Initials>WB</Initials></Author><Author ValidYN="Y"><LastName>Lin</LastName><ForeName>Chun-Hung</ForeName><Initials>CH</Initials></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Jiun-Ling</ForeName><Initials>JL</Initials></Author><Author ValidYN="Y"><LastName>Wu</LastName><ForeName>Yin-Ta</ForeName><Initials>YT</Initials></Author><Author ValidYN="Y"><LastName>Wong</LastName><ForeName>Chi-Huey</ForeName><Initials>CH</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></Article><MedlineJournalInfo><Country>United States</Country><MedlineTA>J Med Chem</MedlineTA><NlmUniqueID>9716531</NlmUniqueID><ISSNLinking>0022-2623</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000813">Anilides</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011480">Protease Inhibitors</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D014764">Viral Proteins</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.-</RegistryNumber><NameOfSubstance UI="D010450">Endopeptidases</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="C099456">3C-like proteinase, Coronavirus</NameOfSubstance></Chemical><Chemical><RegistryNumber>EC 3.4.22.-</RegistryNumber><NameOfSubstance UI="D003546">Cysteine Endopeptidases</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000813" MajorTopicYN="N">Anilides</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D003546" MajorTopicYN="N">Cysteine Endopeptidases</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D010450" MajorTopicYN="N">Endopeptidases</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D007700" MajorTopicYN="N">Kinetics</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008958" MajorTopicYN="N">Models, Molecular</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011480" MajorTopicYN="N">Protease Inhibitors</DescriptorName><QualifierName UI="Q000138" MajorTopicYN="Y">chemical synthesis</QualifierName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="N">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D011487" MajorTopicYN="N">Protein Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D045473" MajorTopicYN="N">SARS Virus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045169" MajorTopicYN="N">Severe Acute Respiratory Syndrome</DescriptorName><QualifierName UI="Q000188" MajorTopicYN="Y">drug therapy</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D014764" MajorTopicYN="N">Viral Proteins</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName><QualifierName UI="Q000378" MajorTopicYN="Y">metabolism</QualifierName></MeshHeading></MeshHeadingList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="pubmed"><Year>2005</Year><Month>6</Month><Day>25</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2005</Year><Month>8</Month><Day>24</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2005</Year><Month>6</Month><Day>25</Day><Hour>9</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">15974598</ArticleId><ArticleId IdType="doi">10.1021/jm050184y</ArticleId></ArticleIdList></PubmedData></pubmed><affiliations><list><country><li>Taïwan</li></country></list><tree><noCountry><name sortKey="Chen, Jiun Ling" sort="Chen, Jiun Ling" uniqKey="Chen J" first="Jiun-Ling" last="Chen">Jiun-Ling Chen</name><name sortKey="Fang, Jim Min" sort="Fang, Jim Min" uniqKey="Fang J" first="Jim-Min" last="Fang">Jim-Min Fang</name><name sortKey="Huang, Hung Jyun" sort="Huang, Hung Jyun" uniqKey="Huang H" first="Hung-Jyun" last="Huang">Hung-Jyun Huang</name><name sortKey="Kuo, Chih Jung" sort="Kuo, Chih Jung" uniqKey="Kuo C" first="Chih-Jung" last="Kuo">Chih-Jung Kuo</name><name sortKey="Kuo, Tun Hsun" sort="Kuo, Tun Hsun" uniqKey="Kuo T" first="Tun-Hsun" last="Kuo">Tun-Hsun Kuo</name><name sortKey="Liang, Po Huang" sort="Liang, Po Huang" uniqKey="Liang P" first="Po-Huang" last="Liang">Po-Huang Liang</name><name sortKey="Lin, Chun Hung" sort="Lin, Chun Hung" uniqKey="Lin C" first="Chun-Hung" last="Lin">Chun-Hung Lin</name><name sortKey="Wong, Chi Huey" sort="Wong, Chi Huey" uniqKey="Wong C" first="Chi-Huey" last="Wong">Chi-Huey Wong</name><name sortKey="Wu, Yin Ta" sort="Wu, Yin Ta" uniqKey="Wu Y" first="Yin-Ta" last="Wu">Yin-Ta Wu</name><name sortKey="Yang, Wen Bin" sort="Yang, Wen Bin" uniqKey="Yang W" first="Wen-Bin" last="Yang">Wen-Bin Yang</name></noCountry><country name="Taïwan"><noRegion><name sortKey="Shie, Jiun Jie" sort="Shie, Jiun Jie" uniqKey="Shie J" first="Jiun-Jie" last="Shie">Jiun-Jie Shie</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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