Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant
Identifieur interne : 003504 ( Main/Curation ); précédent : 003503; suivant : 003505Evaluation of peptide-aldehyde inhibitors using R188I mutant of SARS 3CL protease as a proteolysis-resistant mutant
Auteurs : Kenichi Akaji [Japon] ; Hiroyuki Konno [Japon] ; Mari Onozuka [Japon] ; Ayumi Makino [Japon] ; Hiroyuki Saito [Japon] ; Kazuto Nosaka [Japon]Source :
- Bioorganic & medicinal chemistry [ 0968-0896 ] ; 2008.
Descripteurs français
- KwdFr :
- Aldéhydes (pharmacologie), Aldéhydes (synthèse chimique), Conformation des protéines, Cysteine endopeptidases (génétique), Cysteine endopeptidases (métabolisme), Données de séquences moléculaires, Humains, Hydrolyse, Inhibiteurs de protéases (pharmacologie), Inhibiteurs de protéases (synthèse chimique), Maturation post-traductionnelle des protéines, Modèles moléculaires, Mutation (génétique), Protéines virales (antagonistes et inhibiteurs), Protéines virales (génétique), Protéines virales (métabolisme), Sites de fixation, Spectrométrie de masse MALDI, Spécificité du substrat, Structure moléculaire, Syndrome respiratoire aigu sévère (génétique), Séquence d'acides aminés, Virus du SRAS (enzymologie), Virus du SRAS (génétique), Virus du SRAS (métabolisme).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- enzymologie : Virus du SRAS.
- génétique : Cysteine endopeptidases, Mutation, Protéines virales, Syndrome respiratoire aigu sévère, Virus du SRAS.
- métabolisme : Cysteine endopeptidases, Protéines virales, Virus du SRAS.
- pharmacologie : Aldéhydes, Inhibiteurs de protéases.
- synthèse chimique : Aldéhydes, Inhibiteurs de protéases.
- Pascal (Inist)
- Conformation des protéines, Données de séquences moléculaires, Humains, Hydrolyse, Maturation post-traductionnelle des protéines, Modèles moléculaires, Peptide, Aldéhyde, Inhibiteur protease, Mutation, Cysteine endopeptidases, Sites de fixation, Spectrométrie de masse MALDI, Spécificité du substrat, Structure moléculaire, Séquence d'acides aminés, Virus syndrome respiratoire aigu sévère, Résistance hydrolyse, Activité biologique, Synthèse chimique, Synthèse peptidique, In vitro, Inhibiteur enzyme, Glutamique acide(acétylthréonyl-séryl-alanyl-valyl-leucyl-1-désoxy).
English descriptors
- KwdEn :
- Aldehyde, Aldehydes (chemical synthesis), Aldehydes (pharmacology), Amino Acid Sequence, Binding Sites, Biological activity, Chemical synthesis, Cysteine Endopeptidases (genetics), Cysteine Endopeptidases (metabolism), Cysteine endopeptidases, Enzyme inhibitor, Humans, Hydrolysis, Hydrolysis resistance, In vitro, Models, Molecular, Molecular Sequence Data, Molecular Structure, Mutation, Mutation (genetics), Peptide synthesis, Peptides, Protease Inhibitors (chemical synthesis), Protease Inhibitors (pharmacology), Protease inhibitor, Protein Conformation, Protein Processing, Post-Translational, SARS Virus (enzymology), SARS Virus (genetics), SARS Virus (metabolism), Severe Acute Respiratory Syndrome (genetics), Severe acute respiratory syndrome virus, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, Substrate Specificity, Viral Proteins (antagonists & inhibitors), Viral Proteins (genetics), Viral Proteins (metabolism).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Aldehydes, Protease Inhibitors.
- chemical , genetics : Cysteine Endopeptidases, Viral Proteins.
- chemical , metabolism : Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Aldehydes, Protease Inhibitors.
- enzymology : SARS Virus.
- genetics : Mutation, SARS Virus, Severe Acute Respiratory Syndrome.
- metabolism : SARS Virus.
- Amino Acid Sequence, Binding Sites, Humans, Hydrolysis, Models, Molecular, Molecular Sequence Data, Molecular Structure, Protein Conformation, Protein Processing, Post-Translational, Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization, Substrate Specificity.
Abstract
The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a Km of 33.8 μM and kcat of 4753 s-1. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 106. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.
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Pascal:09-0041831Le document en format XML
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<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Aldehyde</term>
<term>Aldehydes (chemical synthesis)</term>
<term>Aldehydes (pharmacology)</term>
<term>Amino Acid Sequence</term>
<term>Binding Sites</term>
<term>Biological activity</term>
<term>Chemical synthesis</term>
<term>Cysteine Endopeptidases (genetics)</term>
<term>Cysteine Endopeptidases (metabolism)</term>
<term>Cysteine endopeptidases</term>
<term>Enzyme inhibitor</term>
<term>Humans</term>
<term>Hydrolysis</term>
<term>Hydrolysis resistance</term>
<term>In vitro</term>
<term>Models, Molecular</term>
<term>Molecular Sequence Data</term>
<term>Molecular Structure</term>
<term>Mutation</term>
<term>Mutation (genetics)</term>
<term>Peptide synthesis</term>
<term>Peptides</term>
<term>Protease Inhibitors (chemical synthesis)</term>
<term>Protease Inhibitors (pharmacology)</term>
<term>Protease inhibitor</term>
<term>Protein Conformation</term>
<term>Protein Processing, Post-Translational</term>
<term>SARS Virus (enzymology)</term>
<term>SARS Virus (genetics)</term>
<term>SARS Virus (metabolism)</term>
<term>Severe Acute Respiratory Syndrome (genetics)</term>
<term>Severe acute respiratory syndrome virus</term>
<term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term>
<term>Substrate Specificity</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (genetics)</term>
<term>Viral Proteins (metabolism)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Aldéhydes (pharmacologie)</term>
<term>Aldéhydes (synthèse chimique)</term>
<term>Conformation des protéines</term>
<term>Cysteine endopeptidases (génétique)</term>
<term>Cysteine endopeptidases (métabolisme)</term>
<term>Données de séquences moléculaires</term>
<term>Humains</term>
<term>Hydrolyse</term>
<term>Inhibiteurs de protéases (pharmacologie)</term>
<term>Inhibiteurs de protéases (synthèse chimique)</term>
<term>Maturation post-traductionnelle des protéines</term>
<term>Modèles moléculaires</term>
<term>Mutation (génétique)</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Protéines virales (génétique)</term>
<term>Protéines virales (métabolisme)</term>
<term>Sites de fixation</term>
<term>Spectrométrie de masse MALDI</term>
<term>Spécificité du substrat</term>
<term>Structure moléculaire</term>
<term>Syndrome respiratoire aigu sévère (génétique)</term>
<term>Séquence d'acides aminés</term>
<term>Virus du SRAS (enzymologie)</term>
<term>Virus du SRAS (génétique)</term>
<term>Virus du SRAS (métabolisme)</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>Aldehydes</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Aldehydes</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Virus du SRAS</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Mutation</term>
<term>SARS Virus</term>
<term>Severe Acute Respiratory Syndrome</term>
</keywords>
<keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Cysteine endopeptidases</term>
<term>Mutation</term>
<term>Protéines virales</term>
<term>Syndrome respiratoire aigu sévère</term>
<term>Virus du SRAS</term>
</keywords>
<keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Cysteine endopeptidases</term>
<term>Protéines virales</term>
<term>Virus du SRAS</term>
</keywords>
<keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Aldéhydes</term>
<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Aldéhydes</term>
<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term>
<term>Binding Sites</term>
<term>Humans</term>
<term>Hydrolysis</term>
<term>Models, Molecular</term>
<term>Molecular Sequence Data</term>
<term>Molecular Structure</term>
<term>Protein Conformation</term>
<term>Protein Processing, Post-Translational</term>
<term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term>
<term>Substrate Specificity</term>
</keywords>
<keywords scheme="Pascal" xml:lang="fr"><term>Conformation des protéines</term>
<term>Données de séquences moléculaires</term>
<term>Humains</term>
<term>Hydrolyse</term>
<term>Maturation post-traductionnelle des protéines</term>
<term>Modèles moléculaires</term>
<term>Peptide</term>
<term>Aldéhyde</term>
<term>Inhibiteur protease</term>
<term>Mutation</term>
<term>Cysteine endopeptidases</term>
<term>Sites de fixation</term>
<term>Spectrométrie de masse MALDI</term>
<term>Spécificité du substrat</term>
<term>Structure moléculaire</term>
<term>Séquence d'acides aminés</term>
<term>Virus syndrome respiratoire aigu sévère</term>
<term>Résistance hydrolyse</term>
<term>Activité biologique</term>
<term>Synthèse chimique</term>
<term>Synthèse peptidique</term>
<term>In vitro</term>
<term>Inhibiteur enzyme</term>
<term>Glutamique acide(acétylthréonyl-séryl-alanyl-valyl-leucyl-1-désoxy)</term>
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<front><div type="abstract" xml:lang="en">The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K<sub>m</sub>
of 33.8 μM and k<sub>cat</sub>
of 4753 s<sup>-1</sup>
. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 10<sup>6</sup>
. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.</div>
</front>
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<front><div type="abstract" xml:lang="en">The 3C-like (3CL) protease of the severe acute respiratory syndrome (SARS) coronavirus is a key enzyme for the virus maturation. We found for the first time that the mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. Replacing Arg with lle at position 188 rendered the protease resistant to proteolysis. The R188I mutant digested a conserved undecapeptide substrate with a K<sub>m</sub>
of 33.8 μM and k<sub>cat</sub>
of 4753 s<sup>-1</sup>
. Compared with the value reported for the mature protease containing a C-terminal His-tag, the relative activity of the mutant was nearly 10<sup>6</sup>
. Novel peptide-aldehyde derivatives containing a side-chain-protected C-terminal Gln efficiently inhibited the catalytic activity of the R188I mutant. The results indicated for the first time that the tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde derivatives.</div>
</front>
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<term>Cysteine endopeptidases (métabolisme)</term>
<term>Données de séquences moléculaires</term>
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<term>Hydrolyse</term>
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<term>Inhibiteurs de protéases (synthèse chimique)</term>
<term>Maturation post-traductionnelle des protéines</term>
<term>Modèles moléculaires</term>
<term>Mutation (génétique)</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Protéines virales (génétique)</term>
<term>Protéines virales (métabolisme)</term>
<term>Sites de fixation</term>
<term>Spectrométrie de masse MALDI</term>
<term>Spécificité du substrat</term>
<term>Structure moléculaire</term>
<term>Syndrome respiratoire aigu sévère (génétique)</term>
<term>Séquence d'acides aminés</term>
<term>Virus du SRAS (enzymologie)</term>
<term>Virus du SRAS (génétique)</term>
<term>Virus du SRAS (métabolisme)</term>
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<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>Aldehydes</term>
<term>Protease Inhibitors</term>
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<keywords scheme="MESH" type="chemical" qualifier="genetics" xml:lang="en"><term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Cysteine Endopeptidases</term>
<term>Viral Proteins</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Aldehydes</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Protéines virales</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymologie" xml:lang="fr"><term>Virus du SRAS</term>
</keywords>
<keywords scheme="MESH" qualifier="enzymology" xml:lang="en"><term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="genetics" xml:lang="en"><term>Mutation</term>
<term>SARS Virus</term>
<term>Severe Acute Respiratory Syndrome</term>
</keywords>
<keywords scheme="MESH" qualifier="génétique" xml:lang="fr"><term>Cysteine endopeptidases</term>
<term>Mutation</term>
<term>Protéines virales</term>
<term>Syndrome respiratoire aigu sévère</term>
<term>Virus du SRAS</term>
</keywords>
<keywords scheme="MESH" qualifier="metabolism" xml:lang="en"><term>SARS Virus</term>
</keywords>
<keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Cysteine endopeptidases</term>
<term>Protéines virales</term>
<term>Virus du SRAS</term>
</keywords>
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<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Aldéhydes</term>
<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Amino Acid Sequence</term>
<term>Binding Sites</term>
<term>Humans</term>
<term>Hydrolysis</term>
<term>Models, Molecular</term>
<term>Molecular Sequence Data</term>
<term>Molecular Structure</term>
<term>Protein Conformation</term>
<term>Protein Processing, Post-Translational</term>
<term>Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization</term>
<term>Substrate Specificity</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Conformation des protéines</term>
<term>Données de séquences moléculaires</term>
<term>Humains</term>
<term>Hydrolyse</term>
<term>Maturation post-traductionnelle des protéines</term>
<term>Modèles moléculaires</term>
<term>Sites de fixation</term>
<term>Spectrométrie de masse MALDI</term>
<term>Spécificité du substrat</term>
<term>Structure moléculaire</term>
<term>Séquence d'acides aminés</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><title>Graphical abstract</title>
<p>The mature SARS 3CL protease is subject to degradation at 188Arg/189Gln. The tetrapeptide sequence is enough for inhibitory activities of peptide-aldehyde inhibitor of the protease.</p>
<fig id="d32e1117" position="anchor"><graphic xlink:href="fx1"></graphic>
</fig>
</div>
</front>
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