Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor
Identifieur interne : 004408 ( Main/Curation ); précédent : 004407; suivant : 004409Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor
Auteurs : Syaulan Yang [Taïwan] ; Shu-Jen Chen [Taïwan] ; Min-Feng Hsu [Taïwan] ; Jen-Dar Wu [Taïwan] ; Chien-Te K. Tseng [États-Unis] ; Yu-Fan Liu [Taïwan] ; Hua-Chien Chen [Taïwan] ; Chun-Wei Kuo [Taïwan] ; Chi-Shen Wu [Taïwan] ; Li-Wen Chang [Taïwan] ; Wen-Chang Chen [Taïwan] ; Shao-Ying Liao [Taïwan] ; Teng-Yuan Chang [Taïwan] ; Hsin-Hui Hung [Taïwan] ; Hui-Lin Shr [Taïwan] ; Cheng-Yuan Liu [Taïwan] ; Yu-An Huang [Taïwan] ; Ling-Yin Chang [Taïwan] ; Jen-Chi Hsu [Taïwan] ; Clarence J. Peters [États-Unis] ; Andrew H.-J. Wang [Taïwan] ; Ming-Chu Hsu [Taïwan]Source :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2006.
Descripteurs français
- KwdFr :
- Animaux, Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Carbamates (), Carbamates (pharmacologie), Carbamates (synthèse chimique), Coronavirus humain 229E (), Cristallographie aux rayons X, Cysteine endopeptidases (), Dipeptides (), Dipeptides (pharmacologie), Dipeptides (synthèse chimique), Humains, Interactions hydrophobes et hydrophiles, Liaison hydrogène, Lignée cellulaire, Modèles moléculaires, Protéines virales (), Protéines virales (antagonistes et inhibiteurs), Rats, Relation structure-activité, Réplication virale (), Souris, Stabilité de médicament, Structure moléculaire, Virus du SRAS ().
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- pharmacologie : Antiviraux, Carbamates, Dipeptides.
- synthèse chimique : Antiviraux, Carbamates, Dipeptides.
- Pascal (Inist)
- Animaux, Antiviraux, Carbamates, Coronavirus humain 229E, Cristallographie aux rayons X, Cysteine endopeptidases, Dipeptides, Humains, Interactions hydrophobes et hydrophiles, Liaison hydrogène, Lignée cellulaire, Modèles moléculaires, Protéines virales, Rats, Relation structure-activité, Réplication virale, Souris, Stabilité de médicament, Structure moléculaire, Synthèse chimique, Structure cristalline, Relation structure activité, Antiviral, Synthèse peptidique, Virus du SRAS, Virus syndrome respiratoire aigu sévère, Inhibiteur protease, Résistance hydrolyse, Plasma sanguin, Tripeptide, Aminoaldéhyde, Hétérocycle azote, Cycle 5 chaînons, Lactame, Modèle moléculaire, Complexe enzyme inhibiteur, Carboxamide, In vitro, Peptidases, Inhibiteur enzyme, Diffraction RX, Structure moléculaire, Liquide biologique, Sang, Peptide, Modélisation, Cyclohexylalanamide([N-benzyloxycarbonyl-3-O-t-butyl-thréonyl]-N-[1-forrmyl-2-(2-oxopyrrolidin-3-yl)éthyl]), TG 0205221, Pyrrolidin-2-one dérivé.
English descriptors
- KwdEn :
- Aminoaldehyde, Animals, Antiviral, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Biological fluid, Blood, Blood plasma, Carbamates (chemical synthesis), Carbamates (chemistry), Carbamates (pharmacology), Carboxamide, Cell Line, Chemical synthesis, Chlorocebus aethiops, Coronavirus 229E, Human (drug effects), Crystalline structure, Crystallography, X-Ray, Cysteine Endopeptidases (chemistry), Dipeptides (chemical synthesis), Dipeptides (chemistry), Dipeptides (pharmacology), Drug Stability, Enzyme inhibitor, Five membered ring, Humans, Hydrogen Bonding, Hydrolysis resistance, Hydrophobic and Hydrophilic Interactions, In vitro, Inhibitor enzyme complex, Lactam, Mice, Modeling, Models, Molecular, Molecular Structure, Molecular model, Molecular structure, Nitrogen heterocycle, Peptidases, Peptide synthesis, Peptides, Protease inhibitor, Rats, SARS Virus (drug effects), Severe acute respiratory syndrome virus, Structure activity relation, Structure-Activity Relationship, Tripeptide, Viral Proteins (antagonists & inhibitors), Viral Proteins (chemistry), Virus Replication (drug effects), X ray diffraction.
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Antiviral Agents, Carbamates, Dipeptides.
- chemical , chemistry : Antiviral Agents, Carbamates, Cysteine Endopeptidases, Dipeptides, Viral Proteins.
- chemical , pharmacology : Antiviral Agents, Carbamates, Dipeptides.
- drug effects : Coronavirus 229E, Human, SARS Virus, Virus Replication.
- Animals, Cell Line, Chlorocebus aethiops, Crystallography, X-Ray, Drug Stability, Humans, Hydrogen Bonding, Hydrophobic and Hydrophilic Interactions, Mice, Models, Molecular, Molecular Structure, Rats, Structure-Activity Relationship.
Abstract
A potent SARS coronavirus (CoV) 3CL protease inhibitor (TG-0205221, Ki = 53 nM) has been developed. TG-0205221 showed remarkable activity against SARS CoV and human coronavirus (HCoV) 229E replications by reducing the viral titer by 4.7 log (at 5 μM) for SARS CoV and 5.2 log (at 1.25 μM) for HCoV 229E. The crystal structure of TG-0205221 (resolution = 1.93 Å) has revealed a unique binding mode comprising a covalent bond, hydrogen bonds, and numerous hydrophobic interactions. Structural comparisons between TG-0205221 and a natural peptide substrate were also discussed. This information may be applied toward the design of other 3CL protease inhibitors.
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Pascal:06-0539611Le document en format XML
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor</title>
<author><name sortKey="Yang, Syaulan" sort="Yang, Syaulan" uniqKey="Yang S" first="Syaulan" last="Yang">Syaulan Yang</name>
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</author>
<author><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name>
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</author>
<author><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name>
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<author><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name>
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<author><name sortKey="Tseng, Chien Te K" sort="Tseng, Chien Te K" uniqKey="Tseng C" first="Chien-Te K." last="Tseng">Chien-Te K. Tseng</name>
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<author><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name>
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<author><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name>
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<author><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name>
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<author><name sortKey="Wu, Chi Shen" sort="Wu, Chi Shen" uniqKey="Wu C" first="Chi-Shen" last="Wu">Chi-Shen Wu</name>
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<author><name sortKey="Chang, Li Wen" sort="Chang, Li Wen" uniqKey="Chang L" first="Li-Wen" last="Chang">Li-Wen Chang</name>
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<author><name sortKey="Chen, Wen Chang" sort="Chen, Wen Chang" uniqKey="Chen W" first="Wen-Chang" last="Chen">Wen-Chang Chen</name>
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<author><name sortKey="Liao, Shao Ying" sort="Liao, Shao Ying" uniqKey="Liao S" first="Shao-Ying" last="Liao">Shao-Ying Liao</name>
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<author><name sortKey="Chang, Teng Yuan" sort="Chang, Teng Yuan" uniqKey="Chang T" first="Teng-Yuan" last="Chang">Teng-Yuan Chang</name>
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<author><name sortKey="Hung, Hsin Hui" sort="Hung, Hsin Hui" uniqKey="Hung H" first="Hsin-Hui" last="Hung">Hsin-Hui Hung</name>
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<author><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name>
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<author><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name>
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<author><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name>
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<author><name sortKey="Peters, Clarence J" sort="Peters, Clarence J" uniqKey="Peters C" first="Clarence J." last="Peters">Clarence J. Peters</name>
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<s2>Galveston, Texas 77555</s2>
<s3>USA</s3>
<sZ>5 aut.</sZ>
<sZ>20 aut.</sZ>
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<country>États-Unis</country>
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<author><name sortKey="Wang, Andrew H J" sort="Wang, Andrew H J" uniqKey="Wang A" first="Andrew H.-J." last="Wang">Andrew H.-J. Wang</name>
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<s2>Taipei 106</s2>
<s3>TWN</s3>
<sZ>3 aut.</sZ>
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<sZ>21 aut.</sZ>
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<author><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
<sZ>1 aut.</sZ>
<sZ>2 aut.</sZ>
<sZ>4 aut.</sZ>
<sZ>6 aut.</sZ>
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</analytic>
<series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
<title level="j" type="abbreviated">J. med. chem. : (Print)</title>
<idno type="ISSN">0022-2623</idno>
<imprint><date when="2006">2006</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
<seriesStmt><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
<title level="j" type="abbreviated">J. med. chem. : (Print)</title>
<idno type="ISSN">0022-2623</idno>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoaldehyde</term>
<term>Animals</term>
<term>Antiviral</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Biological fluid</term>
<term>Blood</term>
<term>Blood plasma</term>
<term>Carbamates (chemical synthesis)</term>
<term>Carbamates (chemistry)</term>
<term>Carbamates (pharmacology)</term>
<term>Carboxamide</term>
<term>Cell Line</term>
<term>Chemical synthesis</term>
<term>Chlorocebus aethiops</term>
<term>Coronavirus 229E, Human (drug effects)</term>
<term>Crystalline structure</term>
<term>Crystallography, X-Ray</term>
<term>Cysteine Endopeptidases (chemistry)</term>
<term>Dipeptides (chemical synthesis)</term>
<term>Dipeptides (chemistry)</term>
<term>Dipeptides (pharmacology)</term>
<term>Drug Stability</term>
<term>Enzyme inhibitor</term>
<term>Five membered ring</term>
<term>Humans</term>
<term>Hydrogen Bonding</term>
<term>Hydrolysis resistance</term>
<term>Hydrophobic and Hydrophilic Interactions</term>
<term>In vitro</term>
<term>Inhibitor enzyme complex</term>
<term>Lactam</term>
<term>Mice</term>
<term>Modeling</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Molecular model</term>
<term>Molecular structure</term>
<term>Nitrogen heterocycle</term>
<term>Peptidases</term>
<term>Peptide synthesis</term>
<term>Peptides</term>
<term>Protease inhibitor</term>
<term>Rats</term>
<term>SARS Virus (drug effects)</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</term>
<term>Structure-Activity Relationship</term>
<term>Tripeptide</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (chemistry)</term>
<term>Virus Replication (drug effects)</term>
<term>X ray diffraction</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Carbamates ()</term>
<term>Carbamates (pharmacologie)</term>
<term>Carbamates (synthèse chimique)</term>
<term>Coronavirus humain 229E ()</term>
<term>Cristallographie aux rayons X</term>
<term>Cysteine endopeptidases ()</term>
<term>Dipeptides ()</term>
<term>Dipeptides (pharmacologie)</term>
<term>Dipeptides (synthèse chimique)</term>
<term>Humains</term>
<term>Interactions hydrophobes et hydrophiles</term>
<term>Liaison hydrogène</term>
<term>Lignée cellulaire</term>
<term>Modèles moléculaires</term>
<term>Protéines virales ()</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Rats</term>
<term>Relation structure-activité</term>
<term>Réplication virale ()</term>
<term>Souris</term>
<term>Stabilité de médicament</term>
<term>Structure moléculaire</term>
<term>Virus du SRAS ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Cysteine Endopeptidases</term>
<term>Dipeptides</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Coronavirus 229E, Human</term>
<term>SARS Virus</term>
<term>Virus Replication</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Cell Line</term>
<term>Chlorocebus aethiops</term>
<term>Crystallography, X-Ray</term>
<term>Drug Stability</term>
<term>Humans</term>
<term>Hydrogen Bonding</term>
<term>Hydrophobic and Hydrophilic Interactions</term>
<term>Mice</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Rats</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Animaux</term>
<term>Antiviraux</term>
<term>Carbamates</term>
<term>Coronavirus humain 229E</term>
<term>Cristallographie aux rayons X</term>
<term>Cysteine endopeptidases</term>
<term>Dipeptides</term>
<term>Humains</term>
<term>Interactions hydrophobes et hydrophiles</term>
<term>Liaison hydrogène</term>
<term>Lignée cellulaire</term>
<term>Modèles moléculaires</term>
<term>Protéines virales</term>
<term>Rats</term>
<term>Relation structure-activité</term>
<term>Réplication virale</term>
<term>Souris</term>
<term>Stabilité de médicament</term>
<term>Structure moléculaire</term>
<term>Synthèse chimique</term>
<term>Structure cristalline</term>
<term>Relation structure activité</term>
<term>Antiviral</term>
<term>Synthèse peptidique</term>
<term>Virus du SRAS</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Inhibiteur protease</term>
<term>Résistance hydrolyse</term>
<term>Plasma sanguin</term>
<term>Tripeptide</term>
<term>Aminoaldéhyde</term>
<term>Hétérocycle azote</term>
<term>Cycle 5 chaînons</term>
<term>Lactame</term>
<term>Modèle moléculaire</term>
<term>Complexe enzyme inhibiteur</term>
<term>Carboxamide</term>
<term>In vitro</term>
<term>Peptidases</term>
<term>Inhibiteur enzyme</term>
<term>Diffraction RX</term>
<term>Structure moléculaire</term>
<term>Liquide biologique</term>
<term>Sang</term>
<term>Peptide</term>
<term>Modélisation</term>
<term>Cyclohexylalanamide([N-benzyloxycarbonyl-3-O-t-butyl-thréonyl]-N-[1-forrmyl-2-(2-oxopyrrolidin-3-yl)éthyl])</term>
<term>TG 0205221</term>
<term>Pyrrolidin-2-one dérivé</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A potent SARS coronavirus (CoV) 3CL protease inhibitor (TG-0205221, K<sub>i</sub>
= 53 nM) has been developed. TG-0205221 showed remarkable activity against SARS CoV and human coronavirus (HCoV) 229E replications by reducing the viral titer by 4.7 log (at 5 μM) for SARS CoV and 5.2 log (at 1.25 μM) for HCoV 229E. The crystal structure of TG-0205221 (resolution = 1.93 Å) has revealed a unique binding mode comprising a covalent bond, hydrogen bonds, and numerous hydrophobic interactions. Structural comparisons between TG-0205221 and a natural peptide substrate were also discussed. This information may be applied toward the design of other 3CL protease inhibitors.</div>
</front>
</TEI>
<double idat="0022-2623:2006:Yang S:synthesis:crystal:structure"><INIST><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en" level="a">Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor</title>
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<author><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name>
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<author><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name>
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<author><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name>
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<author><name sortKey="Tseng, Chien Te K" sort="Tseng, Chien Te K" uniqKey="Tseng C" first="Chien-Te K." last="Tseng">Chien-Te K. Tseng</name>
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<author><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name>
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<author><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name>
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<author><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name>
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<author><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name>
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<author><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name>
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<author><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name>
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<country>États-Unis</country>
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<author><name sortKey="Wang, Andrew H J" sort="Wang, Andrew H J" uniqKey="Wang A" first="Andrew H.-J." last="Wang">Andrew H.-J. Wang</name>
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<author><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name>
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</titleStmt>
<publicationStmt><idno type="wicri:source">INIST</idno>
<idno type="inist">06-0539611</idno>
<date when="2006">2006</date>
<idno type="stanalyst">PASCAL 06-0539611 INIST</idno>
<idno type="RBID">Pascal:06-0539611</idno>
<idno type="wicri:Area/PascalFrancis/Corpus">000432</idno>
<idno type="wicri:Area/PascalFrancis/Curation">000558</idno>
<idno type="wicri:Area/PascalFrancis/Checkpoint">000424</idno>
<idno type="wicri:explorRef" wicri:stream="PascalFrancis" wicri:step="Checkpoint">000424</idno>
<idno type="wicri:doubleKey">0022-2623:2006:Yang S:synthesis:crystal:structure</idno>
<idno type="wicri:Area/Main/Merge">004625</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a">Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor</title>
<author><name sortKey="Yang, Syaulan" sort="Yang, Syaulan" uniqKey="Yang S" first="Syaulan" last="Yang">Syaulan Yang</name>
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</inist:fA14>
<country>Taïwan</country>
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</affiliation>
</author>
<author><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name>
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<country>Taïwan</country>
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</affiliation>
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<author><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name>
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<country>Taïwan</country>
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</affiliation>
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<country>Taïwan</country>
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<author><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name>
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<author><name sortKey="Tseng, Chien Te K" sort="Tseng, Chien Te K" uniqKey="Tseng C" first="Chien-Te K." last="Tseng">Chien-Te K. Tseng</name>
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<author><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name>
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<author><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name>
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<author><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name>
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</inist:fA14>
<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
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<author><name sortKey="Wu, Chi Shen" sort="Wu, Chi Shen" uniqKey="Wu C" first="Chi-Shen" last="Wu">Chi-Shen Wu</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
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<author><name sortKey="Chang, Li Wen" sort="Chang, Li Wen" uniqKey="Chang L" first="Li-Wen" last="Chang">Li-Wen Chang</name>
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<author><name sortKey="Chen, Wen Chang" sort="Chen, Wen Chang" uniqKey="Chen W" first="Wen-Chang" last="Chen">Wen-Chang Chen</name>
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<country>Taïwan</country>
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</affiliation>
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<author><name sortKey="Liao, Shao Ying" sort="Liao, Shao Ying" uniqKey="Liao S" first="Shao-Ying" last="Liao">Shao-Ying Liao</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
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</inist:fA14>
<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Chang, Teng Yuan" sort="Chang, Teng Yuan" uniqKey="Chang T" first="Teng-Yuan" last="Chang">Teng-Yuan Chang</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
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</affiliation>
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<author><name sortKey="Hung, Hsin Hui" sort="Hung, Hsin Hui" uniqKey="Hung H" first="Hsin-Hui" last="Hung">Hsin-Hui Hung</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
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<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Shr, Hui Lin" sort="Shr, Hui Lin" uniqKey="Shr H" first="Hui-Lin" last="Shr">Hui-Lin Shr</name>
<affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Institute of Biological Chemistry, Academia Sinica</s1>
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<s3>TWN</s3>
<sZ>3 aut.</sZ>
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<country>Taïwan</country>
<wicri:noRegion>Taipei 115</wicri:noRegion>
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<s3>TWN</s3>
<sZ>3 aut.</sZ>
<sZ>15 aut.</sZ>
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<country>Taïwan</country>
<wicri:noRegion>Taipei 115</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Liu, Cheng Yuan" sort="Liu, Cheng Yuan" uniqKey="Liu C" first="Cheng-Yuan" last="Liu">Cheng-Yuan Liu</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
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<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
<sZ>1 aut.</sZ>
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<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
<sZ>1 aut.</sZ>
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<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
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<author><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
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<affiliation wicri:level="1"><inist:fA14 i1="05"><s1>Department of Microbiology and Immunology, University of Texas Medical Branch</s1>
<s2>Galveston, Texas 77555</s2>
<s3>USA</s3>
<sZ>5 aut.</sZ>
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<country>États-Unis</country>
<wicri:noRegion>Galveston, Texas 77555</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Wang, Andrew H J" sort="Wang, Andrew H J" uniqKey="Wang A" first="Andrew H.-J." last="Wang">Andrew H.-J. Wang</name>
<affiliation wicri:level="1"><inist:fA14 i1="02"><s1>Institute of Biochemical Sciences, National Taiwan University</s1>
<s2>Taipei 106</s2>
<s3>TWN</s3>
<sZ>3 aut.</sZ>
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<country>Taïwan</country>
<wicri:noRegion>Taipei 106</wicri:noRegion>
</affiliation>
<affiliation wicri:level="1"><inist:fA14 i1="03"><s1>Institute of Biological Chemistry, Academia Sinica</s1>
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<country>Taïwan</country>
<wicri:noRegion>Taipei 115</wicri:noRegion>
</affiliation>
<affiliation wicri:level="1"><inist:fA14 i1="04"><s1>Core Facility for Protein X-ray Crystallography, Academia Sinica</s1>
<s2>Taipei 115</s2>
<s3>TWN</s3>
<sZ>3 aut.</sZ>
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<sZ>21 aut.</sZ>
</inist:fA14>
<country>Taïwan</country>
<wicri:noRegion>Taipei 115</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name>
<affiliation wicri:level="1"><inist:fA14 i1="01"><s1>TaiGen Biotechnology Co</s1>
<s2>Taipei 114</s2>
<s3>TWN</s3>
<sZ>1 aut.</sZ>
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<country>Taïwan</country>
<wicri:noRegion>TaiGen Biotechnology Co</wicri:noRegion>
</affiliation>
</author>
</analytic>
<series><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
<title level="j" type="abbreviated">J. med. chem. : (Print)</title>
<idno type="ISSN">0022-2623</idno>
<imprint><date when="2006">2006</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
<seriesStmt><title level="j" type="main">Journal of medicinal chemistry : (Print)</title>
<title level="j" type="abbreviated">J. med. chem. : (Print)</title>
<idno type="ISSN">0022-2623</idno>
</seriesStmt>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aminoaldehyde</term>
<term>Antiviral</term>
<term>Biological fluid</term>
<term>Blood</term>
<term>Blood plasma</term>
<term>Carboxamide</term>
<term>Chemical synthesis</term>
<term>Crystalline structure</term>
<term>Enzyme inhibitor</term>
<term>Five membered ring</term>
<term>Hydrolysis resistance</term>
<term>In vitro</term>
<term>Inhibitor enzyme complex</term>
<term>Lactam</term>
<term>Modeling</term>
<term>Molecular model</term>
<term>Molecular structure</term>
<term>Nitrogen heterocycle</term>
<term>Peptidases</term>
<term>Peptide synthesis</term>
<term>Peptides</term>
<term>Protease inhibitor</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Structure activity relation</term>
<term>Tripeptide</term>
<term>X ray diffraction</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Synthèse chimique</term>
<term>Structure cristalline</term>
<term>Relation structure activité</term>
<term>Antiviral</term>
<term>Synthèse peptidique</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Inhibiteur protease</term>
<term>Résistance hydrolyse</term>
<term>Plasma sanguin</term>
<term>Tripeptide</term>
<term>Aminoaldéhyde</term>
<term>Hétérocycle azote</term>
<term>Cycle 5 chaînons</term>
<term>Lactame</term>
<term>Modèle moléculaire</term>
<term>Complexe enzyme inhibiteur</term>
<term>Carboxamide</term>
<term>In vitro</term>
<term>Peptidases</term>
<term>Inhibiteur enzyme</term>
<term>Diffraction RX</term>
<term>Structure moléculaire</term>
<term>Liquide biologique</term>
<term>Sang</term>
<term>Peptide</term>
<term>Modélisation</term>
<term>Cyclohexylalanamide([N-benzyloxycarbonyl-3-O-t-butyl-thréonyl]-N-[1-forrmyl-2-(2-oxopyrrolidin-3-yl)éthyl])</term>
<term>TG 0205221</term>
<term>Pyrrolidin-2-one dérivé</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A potent SARS coronavirus (CoV) 3CL protease inhibitor (TG-0205221, K<sub>i</sub>
= 53 nM) has been developed. TG-0205221 showed remarkable activity against SARS CoV and human coronavirus (HCoV) 229E replications by reducing the viral titer by 4.7 log (at 5 μM) for SARS CoV and 5.2 log (at 1.25 μM) for HCoV 229E. The crystal structure of TG-0205221 (resolution = 1.93 Å) has revealed a unique binding mode comprising a covalent bond, hydrogen bonds, and numerous hydrophobic interactions. Structural comparisons between TG-0205221 and a natural peptide substrate were also discussed. This information may be applied toward the design of other 3CL protease inhibitors.</div>
</front>
</TEI>
</INIST>
<PubMed><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor.</title>
<author><name sortKey="Yang, Syaulan" sort="Yang, Syaulan" uniqKey="Yang S" first="Syaulan" last="Yang">Syaulan Yang</name>
<affiliation wicri:level="1"><nlm:affiliation>TaiGen Biotechnology Co., Taipei 114, Taiwan, ROC.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>TaiGen Biotechnology Co., Taipei 114, Taiwan</wicri:regionArea>
<wicri:noRegion>Taiwan</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name>
</author>
<author><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name>
</author>
<author><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name>
</author>
<author><name sortKey="Tseng, Chien Te K" sort="Tseng, Chien Te K" uniqKey="Tseng C" first="Chien-Te K" last="Tseng">Chien-Te K. Tseng</name>
</author>
<author><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name>
</author>
<author><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name>
</author>
<author><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name>
</author>
<author><name sortKey="Wu, Chi Shen" sort="Wu, Chi Shen" uniqKey="Wu C" first="Chi-Shen" last="Wu">Chi-Shen Wu</name>
</author>
<author><name sortKey="Chang, Li Wen" sort="Chang, Li Wen" uniqKey="Chang L" first="Li-Wen" last="Chang">Li-Wen Chang</name>
</author>
<author><name sortKey="Chen, Wen Chang" sort="Chen, Wen Chang" uniqKey="Chen W" first="Wen-Chang" last="Chen">Wen-Chang Chen</name>
</author>
<author><name sortKey="Liao, Shao Ying" sort="Liao, Shao Ying" uniqKey="Liao S" first="Shao-Ying" last="Liao">Shao-Ying Liao</name>
</author>
<author><name sortKey="Chang, Teng Yuan" sort="Chang, Teng Yuan" uniqKey="Chang T" first="Teng-Yuan" last="Chang">Teng-Yuan Chang</name>
</author>
<author><name sortKey="Hung, Hsin Hui" sort="Hung, Hsin Hui" uniqKey="Hung H" first="Hsin-Hui" last="Hung">Hsin-Hui Hung</name>
</author>
<author><name sortKey="Shr, Hui Lin" sort="Shr, Hui Lin" uniqKey="Shr H" first="Hui-Lin" last="Shr">Hui-Lin Shr</name>
</author>
<author><name sortKey="Liu, Cheng Yuan" sort="Liu, Cheng Yuan" uniqKey="Liu C" first="Cheng-Yuan" last="Liu">Cheng-Yuan Liu</name>
</author>
<author><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name>
</author>
<author><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name>
</author>
<author><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name>
</author>
<author><name sortKey="Peters, Clarence J" sort="Peters, Clarence J" uniqKey="Peters C" first="Clarence J" last="Peters">Clarence J. Peters</name>
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<author><name sortKey="Wang, Andrew H J" sort="Wang, Andrew H J" uniqKey="Wang A" first="Andrew H-J" last="Wang">Andrew H-J Wang</name>
</author>
<author><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name>
</author>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor.</title>
<author><name sortKey="Yang, Syaulan" sort="Yang, Syaulan" uniqKey="Yang S" first="Syaulan" last="Yang">Syaulan Yang</name>
<affiliation wicri:level="1"><nlm:affiliation>TaiGen Biotechnology Co., Taipei 114, Taiwan, ROC.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>TaiGen Biotechnology Co., Taipei 114, Taiwan</wicri:regionArea>
<wicri:noRegion>Taiwan</wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name>
</author>
<author><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name>
</author>
<author><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name>
</author>
<author><name sortKey="Tseng, Chien Te K" sort="Tseng, Chien Te K" uniqKey="Tseng C" first="Chien-Te K" last="Tseng">Chien-Te K. Tseng</name>
</author>
<author><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name>
</author>
<author><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name>
</author>
<author><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name>
</author>
<author><name sortKey="Wu, Chi Shen" sort="Wu, Chi Shen" uniqKey="Wu C" first="Chi-Shen" last="Wu">Chi-Shen Wu</name>
</author>
<author><name sortKey="Chang, Li Wen" sort="Chang, Li Wen" uniqKey="Chang L" first="Li-Wen" last="Chang">Li-Wen Chang</name>
</author>
<author><name sortKey="Chen, Wen Chang" sort="Chen, Wen Chang" uniqKey="Chen W" first="Wen-Chang" last="Chen">Wen-Chang Chen</name>
</author>
<author><name sortKey="Liao, Shao Ying" sort="Liao, Shao Ying" uniqKey="Liao S" first="Shao-Ying" last="Liao">Shao-Ying Liao</name>
</author>
<author><name sortKey="Chang, Teng Yuan" sort="Chang, Teng Yuan" uniqKey="Chang T" first="Teng-Yuan" last="Chang">Teng-Yuan Chang</name>
</author>
<author><name sortKey="Hung, Hsin Hui" sort="Hung, Hsin Hui" uniqKey="Hung H" first="Hsin-Hui" last="Hung">Hsin-Hui Hung</name>
</author>
<author><name sortKey="Shr, Hui Lin" sort="Shr, Hui Lin" uniqKey="Shr H" first="Hui-Lin" last="Shr">Hui-Lin Shr</name>
</author>
<author><name sortKey="Liu, Cheng Yuan" sort="Liu, Cheng Yuan" uniqKey="Liu C" first="Cheng-Yuan" last="Liu">Cheng-Yuan Liu</name>
</author>
<author><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name>
</author>
<author><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name>
</author>
<author><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name>
</author>
<author><name sortKey="Peters, Clarence J" sort="Peters, Clarence J" uniqKey="Peters C" first="Clarence J" last="Peters">Clarence J. Peters</name>
</author>
<author><name sortKey="Wang, Andrew H J" sort="Wang, Andrew H J" uniqKey="Wang A" first="Andrew H-J" last="Wang">Andrew H-J Wang</name>
</author>
<author><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name>
</author>
</analytic>
<series><title level="j">Journal of medicinal chemistry</title>
<idno type="ISSN">0022-2623</idno>
<imprint><date when="2006" type="published">2006</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Animals</term>
<term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Carbamates (chemical synthesis)</term>
<term>Carbamates (chemistry)</term>
<term>Carbamates (pharmacology)</term>
<term>Cell Line</term>
<term>Chlorocebus aethiops</term>
<term>Coronavirus 229E, Human (drug effects)</term>
<term>Crystallography, X-Ray</term>
<term>Cysteine Endopeptidases (chemistry)</term>
<term>Dipeptides (chemical synthesis)</term>
<term>Dipeptides (chemistry)</term>
<term>Dipeptides (pharmacology)</term>
<term>Drug Stability</term>
<term>Humans</term>
<term>Hydrogen Bonding</term>
<term>Hydrophobic and Hydrophilic Interactions</term>
<term>Mice</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Rats</term>
<term>SARS Virus (drug effects)</term>
<term>Structure-Activity Relationship</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (chemistry)</term>
<term>Virus Replication (drug effects)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Carbamates ()</term>
<term>Carbamates (pharmacologie)</term>
<term>Carbamates (synthèse chimique)</term>
<term>Coronavirus humain 229E ()</term>
<term>Cristallographie aux rayons X</term>
<term>Cysteine endopeptidases ()</term>
<term>Dipeptides ()</term>
<term>Dipeptides (pharmacologie)</term>
<term>Dipeptides (synthèse chimique)</term>
<term>Humains</term>
<term>Interactions hydrophobes et hydrophiles</term>
<term>Liaison hydrogène</term>
<term>Lignée cellulaire</term>
<term>Modèles moléculaires</term>
<term>Protéines virales ()</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Rats</term>
<term>Relation structure-activité</term>
<term>Réplication virale ()</term>
<term>Souris</term>
<term>Stabilité de médicament</term>
<term>Structure moléculaire</term>
<term>Virus du SRAS ()</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Cysteine Endopeptidases</term>
<term>Dipeptides</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Coronavirus 229E, Human</term>
<term>SARS Virus</term>
<term>Virus Replication</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term>
<term>Carbamates</term>
<term>Dipeptides</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Animals</term>
<term>Cell Line</term>
<term>Chlorocebus aethiops</term>
<term>Crystallography, X-Ray</term>
<term>Drug Stability</term>
<term>Humans</term>
<term>Hydrogen Bonding</term>
<term>Hydrophobic and Hydrophilic Interactions</term>
<term>Mice</term>
<term>Models, Molecular</term>
<term>Molecular Structure</term>
<term>Rats</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Animaux</term>
<term>Antiviraux</term>
<term>Carbamates</term>
<term>Coronavirus humain 229E</term>
<term>Cristallographie aux rayons X</term>
<term>Cysteine endopeptidases</term>
<term>Dipeptides</term>
<term>Humains</term>
<term>Interactions hydrophobes et hydrophiles</term>
<term>Liaison hydrogène</term>
<term>Lignée cellulaire</term>
<term>Modèles moléculaires</term>
<term>Protéines virales</term>
<term>Rats</term>
<term>Relation structure-activité</term>
<term>Réplication virale</term>
<term>Souris</term>
<term>Stabilité de médicament</term>
<term>Structure moléculaire</term>
<term>Virus du SRAS</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en">A potent SARS coronavirus (CoV) 3CL protease inhibitor (TG-0205221, Ki = 53 nM) has been developed. TG-0205221 showed remarkable activity against SARS CoV and human coronavirus (HCoV) 229E replications by reducing the viral titer by 4.7 log (at 5 microM) for SARS CoV and 5.2 log (at 1.25 microM) for HCoV 229E. The crystal structure of TG-0205221 (resolution = 1.93 A) has revealed a unique binding mode comprising a covalent bond, hydrogen bonds, and numerous hydrophobic interactions. Structural comparisons between TG-0205221 and a natural peptide substrate were also discussed. This information may be applied toward the design of other 3CL protease inhibitors.</div>
</front>
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