Discovery of unsymmetrical aromatic disulfides as novel inhibitors of SARS-CoV main protease: Chemical synthesis, biological evaluation, molecular docking and 3D-QSAR study
Identifieur interne : 002E15 ( Ncbi/Checkpoint ); précédent : 002E14; suivant : 002E16Discovery of unsymmetrical aromatic disulfides as novel inhibitors of SARS-CoV main protease: Chemical synthesis, biological evaluation, molecular docking and 3D-QSAR study
Auteurs : Li Wang [République populaire de Chine] ; Bo-Bo Bao [République populaire de Chine] ; Guo-Qing Song [République populaire de Chine] ; Cheng Chen [République populaire de Chine] ; Xu-Meng Zhang [République populaire de Chine] ; Wei Lu [République populaire de Chine] ; Zefang Wang [République populaire de Chine] ; Yan Cai [République populaire de Chine] ; Shuang Li [République populaire de Chine] ; Sheng Fu [République populaire de Chine] ; Fu-Hang Song [République populaire de Chine] ; Haitao Yang [République populaire de Chine] ; Jian-Guo Wang [République populaire de Chine]Source :
- European Journal of Medicinal Chemistry [ 0223-5234 ] ; 2017.
Descripteurs français
- KwdFr :
- Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Cysteine endopeptidases (métabolisme), Disulfures (), Disulfures (pharmacologie), Disulfures (synthèse chimique), Découverte de médicament, Hydrocarbures aromatiques (), Hydrocarbures aromatiques (pharmacologie), Hydrocarbures aromatiques (synthèse chimique), Inhibiteurs de protéases (), Inhibiteurs de protéases (pharmacologie), Inhibiteurs de protéases (synthèse chimique), Protéines virales (antagonistes et inhibiteurs), Protéines virales (métabolisme), Relation dose-effet des médicaments, Relation quantitative structure-activité, Simulation de docking moléculaire, Structure moléculaire, Tests de sensibilité microbienne, Virus du SRAS (), Virus du SRAS (enzymologie).
- MESH :
- antagonistes et inhibiteurs : Protéines virales.
- enzymologie : Virus du SRAS.
- métabolisme : Cysteine endopeptidases, Protéines virales.
- pharmacologie : Antiviraux, Disulfures, Hydrocarbures aromatiques, Inhibiteurs de protéases.
- synthèse chimique : Antiviraux, Disulfures, Hydrocarbures aromatiques, Inhibiteurs de protéases.
- Antiviraux, Disulfures, Découverte de médicament, Hydrocarbures aromatiques, Inhibiteurs de protéases, Relation dose-effet des médicaments, Relation quantitative structure-activité, Simulation de docking moléculaire, Structure moléculaire, Tests de sensibilité microbienne, Virus du SRAS.
English descriptors
- KwdEn :
- Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cysteine Endopeptidases (metabolism), Disulfides (chemical synthesis), Disulfides (chemistry), Disulfides (pharmacology), Dose-Response Relationship, Drug, Drug Discovery, Hydrocarbons, Aromatic (chemical synthesis), Hydrocarbons, Aromatic (chemistry), Hydrocarbons, Aromatic (pharmacology), Microbial Sensitivity Tests, Molecular Docking Simulation, Molecular Structure, Protease Inhibitors (chemical synthesis), Protease Inhibitors (chemistry), Protease Inhibitors (pharmacology), Quantitative Structure-Activity Relationship, SARS Virus (drug effects), SARS Virus (enzymology), Viral Proteins (antagonists & inhibitors), Viral Proteins (metabolism).
- MESH :
- chemical , antagonists & inhibitors : Viral Proteins.
- chemical , chemical synthesis : Antiviral Agents, Disulfides, Hydrocarbons, Aromatic, Protease Inhibitors.
- chemical , chemistry : Antiviral Agents, Disulfides, Hydrocarbons, Aromatic, Protease Inhibitors.
- chemical , metabolism : Cysteine Endopeptidases, Viral Proteins.
- chemical , pharmacology : Antiviral Agents, Disulfides, Hydrocarbons, Aromatic, Protease Inhibitors.
- drug effects : SARS Virus.
- enzymology : SARS Virus.
- Dose-Response Relationship, Drug, Drug Discovery, Microbial Sensitivity Tests, Molecular Docking Simulation, Molecular Structure, Quantitative Structure-Activity Relationship.
Abstract
The worldwide outbreak of severe acute respiratory syndrome (SARS) in 2003 had caused a high rate of mortality. Main protease (Mpro) of SARS-associated coronavirus (SARS-CoV) is an important target to discover pharmaceutical compounds for the therapy of this life-threatening disease. During the course of screening new anti-SARS agents, we have identified that a series of unsymmetrical aromatic disulfides inhibited SARS-CoV Mpro significantly for the first time. Herein, 40 novel unsymmetrical aromatic disulfides were synthesized chemically and their biological activities were evaluated
Url:
DOI: 10.1016/j.ejmech.2017.05.045
PubMed: 28624700
PubMed Central: 7115414
Affiliations:
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<author><name sortKey="Lu, Wei" sort="Lu, Wei" uniqKey="Lu W" first="Wei" last="Lu">Wei Lu</name>
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</author>
<author><name sortKey="Fu, Sheng" sort="Fu, Sheng" uniqKey="Fu S" first="Sheng" last="Fu">Sheng Fu</name>
<affiliation wicri:level="1"><nlm:aff id="aff2">School of Life Sciences, Tianjin University, Tianjin 300072, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>School of Life Sciences, Tianjin University, Tianjin 300072</wicri:regionArea>
<placeName><settlement type="city">Tianjin</settlement>
</placeName>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="aff3">Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457</wicri:regionArea>
<placeName><settlement type="city">Tianjin</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Song, Fu Hang" sort="Song, Fu Hang" uniqKey="Song F" first="Fu-Hang" last="Song">Fu-Hang Song</name>
<affiliation wicri:level="1"><nlm:aff id="aff4">CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology, Chinese Academy of Sciences, Beijing 100101</wicri:regionArea>
<placeName><settlement type="city">Pékin</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Yang, Haitao" sort="Yang, Haitao" uniqKey="Yang H" first="Haitao" last="Yang">Haitao Yang</name>
<affiliation wicri:level="1"><nlm:aff id="aff2">School of Life Sciences, Tianjin University, Tianjin 300072, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>School of Life Sciences, Tianjin University, Tianjin 300072</wicri:regionArea>
<placeName><settlement type="city">Tianjin</settlement>
</placeName>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="aff3">Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>Tianjin International Joint Academy of Biotechnology and Medicine, Tianjin 300457</wicri:regionArea>
<placeName><settlement type="city">Tianjin</settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Wang, Jian Guo" sort="Wang, Jian Guo" uniqKey="Wang J" first="Jian-Guo" last="Wang">Jian-Guo Wang</name>
<affiliation wicri:level="1"><nlm:aff id="aff1">State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center, College of Chemistry, Nankai University, Tianjin 300071, China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea>State-Key Laboratory and Research Institute of Elemento-Organic Chemistry, National Pesticide Engineering Research Center, College of Chemistry, Nankai University, Tianjin 300071</wicri:regionArea>
<placeName><settlement type="city">Tianjin</settlement>
</placeName>
</affiliation>
</author>
</analytic>
<series><title level="j">European Journal of Medicinal Chemistry</title>
<idno type="ISSN">0223-5234</idno>
<idno type="eISSN">1768-3254</idno>
<imprint><date when="2017">2017</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemical synthesis)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Cysteine Endopeptidases (metabolism)</term>
<term>Disulfides (chemical synthesis)</term>
<term>Disulfides (chemistry)</term>
<term>Disulfides (pharmacology)</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Discovery</term>
<term>Hydrocarbons, Aromatic (chemical synthesis)</term>
<term>Hydrocarbons, Aromatic (chemistry)</term>
<term>Hydrocarbons, Aromatic (pharmacology)</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Docking Simulation</term>
<term>Molecular Structure</term>
<term>Protease Inhibitors (chemical synthesis)</term>
<term>Protease Inhibitors (chemistry)</term>
<term>Protease Inhibitors (pharmacology)</term>
<term>Quantitative Structure-Activity Relationship</term>
<term>SARS Virus (drug effects)</term>
<term>SARS Virus (enzymology)</term>
<term>Viral Proteins (antagonists & inhibitors)</term>
<term>Viral Proteins (metabolism)</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Antiviraux (synthèse chimique)</term>
<term>Cysteine endopeptidases (métabolisme)</term>
<term>Disulfures ()</term>
<term>Disulfures (pharmacologie)</term>
<term>Disulfures (synthèse chimique)</term>
<term>Découverte de médicament</term>
<term>Hydrocarbures aromatiques ()</term>
<term>Hydrocarbures aromatiques (pharmacologie)</term>
<term>Hydrocarbures aromatiques (synthèse chimique)</term>
<term>Inhibiteurs de protéases ()</term>
<term>Inhibiteurs de protéases (pharmacologie)</term>
<term>Inhibiteurs de protéases (synthèse chimique)</term>
<term>Protéines virales (antagonistes et inhibiteurs)</term>
<term>Protéines virales (métabolisme)</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation quantitative structure-activité</term>
<term>Simulation de docking moléculaire</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</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>Antiviral Agents</term>
<term>Disulfides</term>
<term>Hydrocarbons, Aromatic</term>
<term>Protease Inhibitors</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term>
<term>Disulfides</term>
<term>Hydrocarbons, Aromatic</term>
<term>Protease Inhibitors</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>Antiviral Agents</term>
<term>Disulfides</term>
<term>Hydrocarbons, Aromatic</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="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>Antiviraux</term>
<term>Disulfures</term>
<term>Hydrocarbures aromatiques</term>
<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antiviraux</term>
<term>Disulfures</term>
<term>Hydrocarbures aromatiques</term>
<term>Inhibiteurs de protéases</term>
</keywords>
<keywords scheme="MESH" xml:lang="en"><term>Dose-Response Relationship, Drug</term>
<term>Drug Discovery</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Docking Simulation</term>
<term>Molecular Structure</term>
<term>Quantitative Structure-Activity Relationship</term>
</keywords>
<keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term>
<term>Disulfures</term>
<term>Découverte de médicament</term>
<term>Hydrocarbures aromatiques</term>
<term>Inhibiteurs de protéases</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation quantitative structure-activité</term>
<term>Simulation de docking moléculaire</term>
<term>Structure moléculaire</term>
<term>Tests de sensibilité microbienne</term>
<term>Virus du SRAS</term>
</keywords>
</textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p>The worldwide outbreak of severe acute respiratory syndrome (SARS) in 2003 had caused a high rate of mortality. Main protease (M<sup>pro</sup>
) of SARS-associated coronavirus (SARS-CoV) is an important target to discover pharmaceutical compounds for the therapy of this life-threatening disease. During the course of screening new anti-SARS agents, we have identified that a series of unsymmetrical aromatic disulfides inhibited SARS-CoV M<sup>pro</sup>
significantly for the first time. Herein, 40 novel unsymmetrical aromatic disulfides were synthesized chemically and their biological activities were evaluated <italic>in vitro</italic>
against SARS-CoV M<sup>pro</sup>
. These novel compounds displayed excellent <italic>IC</italic>
<sub>50</sub>
data in the range of 0.516–5.954 μM. Preliminary studies indicated that these disulfides are reversible and mpetitive inhibitors. A possible binding mode was generated via molecular docking simulation and a comparative field analysis (CoMFA) model was constructed to understand the structure-activity relationships. The present research therefore has provided some meaningful guidance to design and identify anti-SARS drugs with totally new chemical structures.</p>
</div>
</front>
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</TEI>
<affiliations><list><country><li>République populaire de Chine</li>
</country>
<settlement><li>Pékin</li>
<li>Tianjin</li>
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</list>
<tree><country name="République populaire de Chine"><noRegion><name sortKey="Wang, Li" sort="Wang, Li" uniqKey="Wang L" first="Li" last="Wang">Li Wang</name>
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<name sortKey="Bao, Bo Bo" sort="Bao, Bo Bo" uniqKey="Bao B" first="Bo-Bo" last="Bao">Bo-Bo Bao</name>
<name sortKey="Bao, Bo Bo" sort="Bao, Bo Bo" uniqKey="Bao B" first="Bo-Bo" last="Bao">Bo-Bo Bao</name>
<name sortKey="Cai, Yan" sort="Cai, Yan" uniqKey="Cai Y" first="Yan" last="Cai">Yan Cai</name>
<name sortKey="Cai, Yan" sort="Cai, Yan" uniqKey="Cai Y" first="Yan" last="Cai">Yan Cai</name>
<name sortKey="Chen, Cheng" sort="Chen, Cheng" uniqKey="Chen C" first="Cheng" last="Chen">Cheng Chen</name>
<name sortKey="Chen, Cheng" sort="Chen, Cheng" uniqKey="Chen C" first="Cheng" last="Chen">Cheng Chen</name>
<name sortKey="Fu, Sheng" sort="Fu, Sheng" uniqKey="Fu S" first="Sheng" last="Fu">Sheng Fu</name>
<name sortKey="Fu, Sheng" sort="Fu, Sheng" uniqKey="Fu S" first="Sheng" last="Fu">Sheng Fu</name>
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<name sortKey="Wang, Jian Guo" sort="Wang, Jian Guo" uniqKey="Wang J" first="Jian-Guo" last="Wang">Jian-Guo Wang</name>
<name sortKey="Wang, Zefang" sort="Wang, Zefang" uniqKey="Wang Z" first="Zefang" last="Wang">Zefang Wang</name>
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<name sortKey="Yang, Haitao" sort="Yang, Haitao" uniqKey="Yang H" first="Haitao" last="Yang">Haitao Yang</name>
<name sortKey="Yang, Haitao" sort="Yang, Haitao" uniqKey="Yang H" first="Haitao" last="Yang">Haitao Yang</name>
<name sortKey="Zhang, Xu Meng" sort="Zhang, Xu Meng" uniqKey="Zhang X" first="Xu-Meng" last="Zhang">Xu-Meng Zhang</name>
</country>
</tree>
</affiliations>
</record>
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