Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure–activity relationship study
Identifieur interne : 001964 ( Main/Exploration ); précédent : 001963; suivant : 001965Design, synthesis, and biological evaluation of novel dipeptide-type SARS-CoV 3CL protease inhibitors: Structure–activity relationship study
Auteurs : Pillaiyar Thanigaimalai [Japon] ; Sho Konno [Japon] ; Takehito Yamamoto [Japon] ; Yuji Koiwai [Japon] ; Akihiro Taguchi [Japon] ; Kentaro Takayama [Japon] ; Fumika Yakushiji [Japon] ; Kenichi Akaji [Japon] ; Yoshiaki Kiso [Japon] ; Yuko Kawasaki [États-Unis] ; Shen-En Chen [États-Unis] ; Aurash Naser-Tavakolian [États-Unis] ; Arne Schön [États-Unis] ; Ernesto Freire [États-Unis] ; Yoshio Hayashi [Japon]Source :
- European Journal of Medicinal Chemistry [ 0223-5234 ] ; 2013.
Descripteurs français
- KwdFr :
- Conception de médicament, Conformation moléculaire, Cysteine endopeptidases (métabolisme), Dipeptides (), Dipeptides (pharmacologie), Dipeptides (synthèse chimique), Humains, Inhibiteurs de la cystéine protéinase (), Inhibiteurs de la cystéine protéinase (pharmacologie), Inhibiteurs de la cystéine protéinase (synthèse chimique), Masse moléculaire, Modèles moléculaires, Protéines virales (antagonistes et inhibiteurs), Protéines virales (métabolisme), Relation dose-effet des médicaments, Relation structure-activité, Virus du SRAS (), Virus du SRAS (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- enzymologie : Virus du SRAS.
- métabolisme : Cysteine endopeptidases, Protéines virales.
- pharmacologie : Dipeptides, Inhibiteurs de la cystéine protéinase.
- synthèse chimique : Dipeptides, Inhibiteurs de la cystéine protéinase.
- Conception de médicament, Conformation moléculaire, Dipeptides, Humains, Inhibiteurs de la cystéine protéinase, Masse moléculaire, Modèles moléculaires, Relation dose-effet des médicaments, Relation structure-activité, Virus du SRAS.
English descriptors
- KwdEn :
- Cysteine Endopeptidases (metabolism), Cysteine Proteinase Inhibitors (chemical synthesis), Cysteine Proteinase Inhibitors (chemistry), Cysteine Proteinase Inhibitors (pharmacology), Dipeptides (chemical synthesis), Dipeptides (chemistry), Dipeptides (pharmacology), Dose-Response Relationship, Drug, Drug Design, Humans, Models, Molecular, Molecular Conformation, Molecular Weight, SARS Virus (drug effects), SARS Virus (enzymology), Structure-Activity Relationship, Viral Proteins (antagonists & inhibitors), Viral Proteins (metabolism).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Cysteine Proteinase Inhibitors, Dipeptides.
- chemical , chemistry : Cysteine Proteinase Inhibitors, Dipeptides.
- chemical , metabolism : Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Cysteine Proteinase Inhibitors, Dipeptides.
- drug effects : SARS Virus.
- enzymology : SARS Virus.
- Dose-Response Relationship, Drug, Drug Design, Humans, Models, Molecular, Molecular Conformation, Molecular Weight, Structure-Activity Relationship.
Abstract
This work describes the design, synthesis, and evaluation of low-molecular weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(pyrrolidone-3-yl)-2-benzothiazole (
Url:
DOI: 10.1016/j.ejmech.2013.05.005
PubMed: 23747811
PubMed Central: 7115367
Affiliations:
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Le document en format XML
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Kantō</region></placeName></affiliation></author><author><name sortKey="Taguchi, Akihiro" sort="Taguchi, Akihiro" uniqKey="Taguchi A" first="Akihiro" last="Taguchi">Akihiro Taguchi</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Takayama, Kentaro" sort="Takayama, Kentaro" uniqKey="Takayama K" first="Kentaro" last="Takayama">Kentaro Takayama</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Yakushiji, Fumika" sort="Yakushiji, Fumika" uniqKey="Yakushiji F" first="Fumika" last="Yakushiji">Fumika Yakushiji</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de Kantō</region></placeName></affiliation></author><author><name sortKey="Akaji, Kenichi" sort="Akaji, Kenichi" uniqKey="Akaji K" first="Kenichi" last="Akaji">Kenichi Akaji</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412</wicri:regionArea><wicri:noRegion>Kyoto 607-8412</wicri:noRegion></affiliation></author><author><name sortKey="Kiso, Yoshiaki" sort="Kiso, Yoshiaki" uniqKey="Kiso Y" first="Yoshiaki" last="Kiso">Yoshiaki Kiso</name><affiliation wicri:level="1"><nlm:aff id="aff2">Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Kyoto Pharmaceutical University, Kyoto 607-8412</wicri:regionArea><wicri:noRegion>Kyoto 607-8412</wicri:noRegion></affiliation></author><author><name sortKey="Kawasaki, Yuko" sort="Kawasaki, Yuko" uniqKey="Kawasaki Y" first="Yuko" last="Kawasaki">Yuko Kawasaki</name><affiliation wicri:level="2"><nlm:aff id="aff3">Department of Biology, Johns Hopkins University, Baltimore, MD, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biology, Johns Hopkins University, Baltimore, MD</wicri:regionArea><placeName><region type="state">Maryland</region></placeName></affiliation></author><author><name sortKey="Chen, Shen En" sort="Chen, Shen En" uniqKey="Chen S" first="Shen-En" last="Chen">Shen-En Chen</name><affiliation wicri:level="2"><nlm:aff id="aff3">Department of Biology, Johns Hopkins University, Baltimore, MD, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biology, Johns Hopkins University, Baltimore, MD</wicri:regionArea><placeName><region type="state">Maryland</region></placeName></affiliation></author><author><name sortKey="Naser Tavakolian, Aurash" sort="Naser Tavakolian, Aurash" uniqKey="Naser 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last="Freire">Ernesto Freire</name><affiliation wicri:level="2"><nlm:aff id="aff3">Department of Biology, Johns Hopkins University, Baltimore, MD, USA</nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Biology, Johns Hopkins University, Baltimore, MD</wicri:regionArea><placeName><region type="state">Maryland</region></placeName></affiliation></author><author><name sortKey="Hayashi, Yoshio" sort="Hayashi, Yoshio" uniqKey="Hayashi Y" first="Yoshio" last="Hayashi">Yoshio Hayashi</name><affiliation wicri:level="1"><nlm:aff id="aff1">Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392, Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Department of Medicinal Chemistry, Tokyo University of Pharmacy and Life Sciences, Tokyo 192-0392</wicri:regionArea><placeName><settlement type="city">Tokyo</settlement><region type="région">Région de 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Relationship</term><term>Viral Proteins (antagonists & inhibitors)</term><term>Viral Proteins (metabolism)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Cysteine endopeptidases (métabolisme)</term><term>Dipeptides ()</term><term>Dipeptides (pharmacologie)</term><term>Dipeptides (synthèse chimique)</term><term>Humains</term><term>Inhibiteurs de la cystéine protéinase ()</term><term>Inhibiteurs de la cystéine protéinase (pharmacologie)</term><term>Inhibiteurs de la cystéine protéinase (synthèse chimique)</term><term>Masse moléculaire</term><term>Modèles moléculaires</term><term>Protéines virales (antagonistes et inhibiteurs)</term><term>Protéines virales (métabolisme)</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Virus du SRAS ()</term><term>Virus du SRAS (enzymologie)</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>Cysteine Proteinase Inhibitors</term><term>Dipeptides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Cysteine Proteinase Inhibitors</term><term>Dipeptides</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>Cysteine Proteinase Inhibitors</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>SARS Virus</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="métabolisme" xml:lang="fr"><term>Cysteine endopeptidases</term><term>Protéines virales</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Dipeptides</term><term>Inhibiteurs de la cystéine protéinase</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Dipeptides</term><term>Inhibiteurs de la cystéine protéinase</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term><term>Drug Design</term><term>Humans</term><term>Models, Molecular</term><term>Molecular Conformation</term><term>Molecular Weight</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Conception de médicament</term><term>Conformation moléculaire</term><term>Dipeptides</term><term>Humains</term><term>Inhibiteurs de la cystéine protéinase</term><term>Masse moléculaire</term><term>Modèles moléculaires</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Virus du SRAS</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p>This work describes the design, synthesis, and evaluation of low-molecular weight peptidic SARS-CoV 3CL protease inhibitors. The inhibitors were designed based on the potent tripeptidic Z-Val-Leu-Ala(pyrrolidone-3-yl)-2-benzothiazole (<bold>8</bold>; <italic>K</italic><sub><italic>i</italic></sub> = 4.1 nM), in which the P3 valine unit was substituted with a variety of distinct moieties. The resulting series of dipeptide-type inhibitors displayed moderate to good inhibitory activities against 3CL<sup>pro</sup>. In particular, compounds <bold>26m</bold> and <bold>26n</bold> exhibited good inhibitory activities with <italic>K</italic><sub><italic>i</italic></sub> values of 0.39 and 0.33 μM, respectively. These low-molecular weight compounds are attractive leads for the further development of potent peptidomimetic inhibitors with pharmaceutical profiles. Docking studies were performed to model the binding interaction of the compound <bold>26m</bold> with the SARS-CoV 3CL protease. The preliminary SAR study of the peptidomimetic compounds with potent inhibitory activities revealed several structural features that boosted the inhibitory activity: (i) a benzothiazole warhead at the S1′ position, (ii) a γ-lactam unit at the S1-position, (iii) an appropriately hydrophobic leucine moiety at the S2-position, and (iv) a hydrogen bond between the <italic>N</italic>-arylglycine unit and a backbone hydrogen bond donor at the S3-position.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Drosten, C" uniqKey="Drosten C">C. Drosten</name></author><author><name sortKey="Gunther, S" uniqKey="Gunther S">S. Gunther</name></author><author><name sortKey="Preiser, W" uniqKey="Preiser W">W. Preiser</name></author><author><name sortKey="Ven Der Werf, S" uniqKey="Ven Der Werf S">S. Ven der Werf</name></author><author><name sortKey="Brodt, H R" uniqKey="Brodt H">H.R. 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HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:23747811" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a SrasV1
| This area was generated with Dilib version V0.6.33. |  |