Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor.
Identifieur interne : 001599 ( Ncbi/Checkpoint ); précédent : 001598; suivant : 001600Synthesis, crystal structure, structure-activity relationships, and antiviral activity of a potent SARS coronavirus 3CL protease inhibitor.
Auteurs : Syaulan Yang [République populaire de Chine] ; Shu-Jen Chen ; Min-Feng Hsu ; Jen-Dar Wu ; Chien-Te K. Tseng ; Yu-Fan Liu ; Hua-Chien Chen ; Chun-Wei Kuo ; Chi-Shen Wu ; Li-Wen Chang ; Wen-Chang Chen ; Shao-Ying Liao ; Teng-Yuan Chang ; Hsin-Hui Hung ; Hui-Lin Shr ; Cheng-Yuan Liu ; Yu-An Huang ; Ling-Yin Chang ; Jen-Chi Hsu ; Clarence J. Peters ; Andrew H-J Wang ; Ming-Chu HsuSource :
- Journal of medicinal chemistry [ 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.
- 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, Virus du SRAS.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Carbamates (chemical synthesis), Carbamates (chemistry), Carbamates (pharmacology), Cell Line, Chlorocebus aethiops, Coronavirus 229E, Human (drug effects), Crystallography, X-Ray, Cysteine Endopeptidases (chemistry), Dipeptides (chemical synthesis), Dipeptides (chemistry), Dipeptides (pharmacology), Drug Stability, Humans, Hydrogen Bonding, Hydrophobic and Hydrophilic Interactions, Mice, Models, Molecular, Molecular Structure, Rats, SARS Virus (drug effects), Structure-Activity Relationship, Viral Proteins (antagonists & inhibitors), Viral Proteins (chemistry), Virus Replication (drug effects).
- 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 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.
DOI: 10.1021/jm0603926
PubMed: 16884309
Affiliations:
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pubmed:16884309Le document en format XML
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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. 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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></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><noCountry><name sortKey="Chang, Li Wen" sort="Chang, Li Wen" uniqKey="Chang L" first="Li-Wen" last="Chang">Li-Wen Chang</name><name sortKey="Chang, Ling Yin" sort="Chang, Ling Yin" uniqKey="Chang L" first="Ling-Yin" last="Chang">Ling-Yin Chang</name><name sortKey="Chang, Teng Yuan" sort="Chang, Teng Yuan" uniqKey="Chang T" first="Teng-Yuan" last="Chang">Teng-Yuan Chang</name><name sortKey="Chen, Hua Chien" sort="Chen, Hua Chien" uniqKey="Chen H" first="Hua-Chien" last="Chen">Hua-Chien Chen</name><name sortKey="Chen, Shu Jen" sort="Chen, Shu Jen" uniqKey="Chen S" first="Shu-Jen" last="Chen">Shu-Jen Chen</name><name sortKey="Chen, Wen Chang" sort="Chen, Wen Chang" uniqKey="Chen W" first="Wen-Chang" last="Chen">Wen-Chang Chen</name><name sortKey="Hsu, Jen Chi" sort="Hsu, Jen Chi" uniqKey="Hsu J" first="Jen-Chi" last="Hsu">Jen-Chi Hsu</name><name sortKey="Hsu, Min Feng" sort="Hsu, Min Feng" uniqKey="Hsu M" first="Min-Feng" last="Hsu">Min-Feng Hsu</name><name sortKey="Hsu, Ming Chu" sort="Hsu, Ming Chu" uniqKey="Hsu M" first="Ming-Chu" last="Hsu">Ming-Chu Hsu</name><name sortKey="Huang, Yu An" sort="Huang, Yu An" uniqKey="Huang Y" first="Yu-An" last="Huang">Yu-An Huang</name><name sortKey="Hung, Hsin Hui" sort="Hung, Hsin Hui" uniqKey="Hung H" first="Hsin-Hui" last="Hung">Hsin-Hui Hung</name><name sortKey="Kuo, Chun Wei" sort="Kuo, Chun Wei" uniqKey="Kuo C" first="Chun-Wei" last="Kuo">Chun-Wei Kuo</name><name sortKey="Liao, Shao Ying" sort="Liao, Shao Ying" uniqKey="Liao S" first="Shao-Ying" last="Liao">Shao-Ying Liao</name><name sortKey="Liu, Cheng Yuan" sort="Liu, Cheng Yuan" uniqKey="Liu C" first="Cheng-Yuan" last="Liu">Cheng-Yuan Liu</name><name sortKey="Liu, Yu Fan" sort="Liu, Yu Fan" uniqKey="Liu Y" first="Yu-Fan" last="Liu">Yu-Fan Liu</name><name sortKey="Peters, Clarence J" sort="Peters, Clarence J" uniqKey="Peters C" first="Clarence J" last="Peters">Clarence J. Peters</name><name sortKey="Shr, Hui Lin" sort="Shr, Hui Lin" uniqKey="Shr H" first="Hui-Lin" last="Shr">Hui-Lin Shr</name><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><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><name sortKey="Wu, Chi Shen" sort="Wu, Chi Shen" uniqKey="Wu C" first="Chi-Shen" last="Wu">Chi-Shen Wu</name><name sortKey="Wu, Jen Dar" sort="Wu, Jen Dar" uniqKey="Wu J" first="Jen-Dar" last="Wu">Jen-Dar Wu</name></noCountry><country name="République populaire de Chine"><noRegion><name sortKey="Yang, Syaulan" sort="Yang, Syaulan" uniqKey="Yang S" first="Syaulan" last="Yang">Syaulan Yang</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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