PandemieGrippaleV1, PubMed, Curation, bibRecord, 000291

Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.

Identifieur interne : 000291 ( PubMed/Curation ); précédent : 000290; suivant : 000292

Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.

Source :

Journal of medicinal chemistry [ 1520-4804 ] ; 2018.

RBID : pubmed:29799746

Descripteurs français

KwdFr :
- Amantadine (), Amantadine (pharmacologie), Antienzymes (), Antienzymes (pharmacologie), Antiviraux (), Antiviraux (pharmacologie), Conformation moléculaire, Découverte de médicament, Hémagglutinines (métabolisme), Imidazoles (), Imidazoles (pharmacologie), Oséltamivir (), Oséltamivir (pharmacologie), Relation dose-effet des médicaments, Relation structure-activité, Résistance virale aux médicaments (), Sialidase (antagonistes et inhibiteurs), Sialidase (métabolisme), Tests de sensibilité microbienne, Virus de la grippe A (), Virus de la grippe A (enzymologie).
MESH :
- antagonistes et inhibiteurs : Sialidase.
- enzymologie : Virus de la grippe A.
- métabolisme : Hémagglutinines, Sialidase.
- pharmacologie : Amantadine, Antienzymes, Antiviraux, Imidazoles, Oséltamivir.
- Amantadine, Antienzymes, Antiviraux, Conformation moléculaire, Découverte de médicament, Imidazoles, Oséltamivir, Relation dose-effet des médicaments, Relation structure-activité, Résistance virale aux médicaments, Tests de sensibilité microbienne, Virus de la grippe A.

English descriptors

KwdEn :
- Amantadine (chemistry), Amantadine (pharmacology), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Dose-Response Relationship, Drug, Drug Discovery, Drug Resistance, Viral (drug effects), Enzyme Inhibitors (chemistry), Enzyme Inhibitors (pharmacology), Hemagglutinins (metabolism), Imidazoles (chemistry), Imidazoles (pharmacology), Influenza A virus (drug effects), Influenza A virus (enzymology), Microbial Sensitivity Tests, Molecular Conformation, Neuraminidase (antagonists & inhibitors), Neuraminidase (metabolism), Oseltamivir (chemistry), Oseltamivir (pharmacology), Structure-Activity Relationship.
MESH :
- chemical , antagonists & inhibitors : Neuraminidase.
- chemical , chemistry : Amantadine, Antiviral Agents, Enzyme Inhibitors, Imidazoles, Oseltamivir.
- chemical , metabolism : Hemagglutinins, Neuraminidase.
- chemical , pharmacology : Amantadine, Antiviral Agents, Enzyme Inhibitors, Imidazoles, Oseltamivir.
- drug effects : Drug Resistance, Viral, Influenza A virus.
- enzymology : Influenza A virus.
- Dose-Response Relationship, Drug, Drug Discovery, Microbial Sensitivity Tests, Molecular Conformation, Structure-Activity Relationship.

Abstract

Influenza pandemic is a constant major threat to public health caused by influenza A viruses (IAVs). IAVs are subcategorized by the surface proteins hemagglutinin (HA) and neuraminidase (NA), in which they are both essential targets for drug discovery. While it is of great concern that NA inhibitor oseltamivir resistant strains are frequently identified from human or avian influenza virus, structural and functional characterization of influenza HA has raised hopes for new antiviral therapies. In this study, we explored a structure-activity relationship (SAR) of pinanamine-based antivirals and discovered a potent inhibitor M090 against amantadine-resistant viruses, including the 2009 H1N1 pandemic strains, and oseltamivir-resistant viruses. Mechanism of action studies, particularly hemolysis inhibition, indicated that M090 targets influenza HA and it occupied a highly conserved pocket of the HA₂ domain and inhibited virus-mediated membrane fusion by "locking" the bending state of HA₂ during the conformational rearrangement process. This work provides new binding sites within the HA protein and indicates that this pocket may be a promising target for broad-spectrum anti-influenza A drug design and development.

DOI: 10.1021/acs.jmedchem.8b00042
PubMed: 29799746

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<author><name sortKey="Zhou, Yang" sort="Zhou, Yang" uniqKey="Zhou Y" first="Yang" last="Zhou">Yang Zhou</name>
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<author><name sortKey="Xiao, Mengjie" sort="Xiao, Mengjie" uniqKey="Xiao M" first="Mengjie" last="Xiao">Mengjie Xiao</name>
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<author><name sortKey="Ma, Chunlong" sort="Ma, Chunlong" uniqKey="Ma C" first="Chunlong" last="Ma">Chunlong Ma</name>
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<author><name sortKey="Yang, Zhongjin" sort="Yang, Zhongjin" uniqKey="Yang Z" first="Zhongjin" last="Yang">Zhongjin Yang</name>
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<author><name sortKey="Zeng, Shaogao" sort="Zeng, Shaogao" uniqKey="Zeng S" first="Shaogao" last="Zeng">Shaogao Zeng</name>
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</affiliation>
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<author><name sortKey="Hu, Yanmei" sort="Hu, Yanmei" uniqKey="Hu Y" first="Yanmei" last="Hu">Yanmei Hu</name>
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<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 </wicri:regionArea>
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</affiliation>
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<author><name sortKey="Mok, Chris Ka Pun" sort="Mok, Chris Ka Pun" uniqKey="Mok C" first="Chris Ka Pun" last="Mok">Chris Ka Pun Mok</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
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</affiliation>
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<author><name sortKey="Sun, Ping" sort="Sun, Ping" uniqKey="Sun P" first="Ping" last="Sun">Ping Sun</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
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</affiliation>
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<author><name sortKey="Dong, Jianghong" sort="Dong, Jianghong" uniqKey="Dong J" first="Jianghong" last="Dong">Jianghong Dong</name>
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<wicri:regionArea>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Cui, Wei" sort="Cui, Wei" uniqKey="Cui W" first="Wei" last="Cui">Wei Cui</name>
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<wicri:regionArea>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 </wicri:regionArea>
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<author><name sortKey="Wang, Jun" sort="Wang, Jun" uniqKey="Wang J" first="Jun" last="Wang">Jun Wang</name>
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<wicri:regionArea>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 </wicri:regionArea>
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<author><name sortKey="Tu, Yaoquan" sort="Tu, Yaoquan" uniqKey="Tu Y" first="Yaoquan" last="Tu">Yaoquan Tu</name>
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</affiliation>
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<author><name sortKey="Yang, Zifeng" sort="Yang, Zifeng" uniqKey="Yang Z" first="Zifeng" last="Yang">Zifeng Yang</name>
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</affiliation>
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<author><name sortKey="Hu, Wenhui" sort="Hu, Wenhui" uniqKey="Hu W" first="Wenhui" last="Hu">Wenhui Hu</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.</title>
<author><name sortKey="Zhao, Xin" sort="Zhao, Xin" uniqKey="Zhao X" first="Xin" last="Zhao">Xin Zhao</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Li, Runfeng" sort="Li, Runfeng" uniqKey="Li R" first="Runfeng" last="Li">Runfeng Li</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Zhou, Yang" sort="Zhou, Yang" uniqKey="Zhou Y" first="Yang" last="Zhou">Yang Zhou</name>
<affiliation wicri:level="1"><nlm:affiliation>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 , Sweden.</nlm:affiliation>
<country xml:lang="fr">Suède</country>
<wicri:regionArea>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Xiao, Mengjie" sort="Xiao, Mengjie" uniqKey="Xiao M" first="Mengjie" last="Xiao">Mengjie Xiao</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Ma, Chunlong" sort="Ma, Chunlong" uniqKey="Ma C" first="Chunlong" last="Ma">Chunlong Ma</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</nlm:affiliation>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Yang, Zhongjin" sort="Yang, Zhongjin" uniqKey="Yang Z" first="Zhongjin" last="Yang">Zhongjin Yang</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Zeng, Shaogao" sort="Zeng, Shaogao" uniqKey="Zeng S" first="Shaogao" last="Zeng">Shaogao Zeng</name>
<affiliation wicri:level="1"><nlm:affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Du, Qiuling" sort="Du, Qiuling" uniqKey="Du Q" first="Qiuling" last="Du">Qiuling Du</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Yang, Chunguang" sort="Yang, Chunguang" uniqKey="Yang C" first="Chunguang" last="Yang">Chunguang Yang</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Jiang, Haiming" sort="Jiang, Haiming" uniqKey="Jiang H" first="Haiming" last="Jiang">Haiming Jiang</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Hu, Yanmei" sort="Hu, Yanmei" uniqKey="Hu Y" first="Yanmei" last="Hu">Yanmei Hu</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</nlm:affiliation>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Wang, Kefeng" sort="Wang, Kefeng" uniqKey="Wang K" first="Kefeng" last="Wang">Kefeng Wang</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Mok, Chris Ka Pun" sort="Mok, Chris Ka Pun" uniqKey="Mok C" first="Chris Ka Pun" last="Mok">Chris Ka Pun Mok</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
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</affiliation>
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<author><name sortKey="Sun, Ping" sort="Sun, Ping" uniqKey="Sun P" first="Ping" last="Sun">Ping Sun</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
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</affiliation>
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<author><name sortKey="Dong, Jianghong" sort="Dong, Jianghong" uniqKey="Dong J" first="Jianghong" last="Dong">Jianghong Dong</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 </wicri:regionArea>
</affiliation>
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<author><name sortKey="Cui, Wei" sort="Cui, Wei" uniqKey="Cui W" first="Wei" last="Cui">Wei Cui</name>
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<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Wang, Jun" sort="Wang, Jun" uniqKey="Wang J" first="Jun" last="Wang">Jun Wang</name>
<affiliation wicri:level="1"><nlm:affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</nlm:affiliation>
<country xml:lang="fr">États-Unis</country>
<wicri:regionArea>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Tu, Yaoquan" sort="Tu, Yaoquan" uniqKey="Tu Y" first="Yaoquan" last="Tu">Yaoquan Tu</name>
<affiliation wicri:level="1"><nlm:affiliation>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 , Sweden.</nlm:affiliation>
<country xml:lang="fr">Suède</country>
<wicri:regionArea>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Yang, Zifeng" sort="Yang, Zifeng" uniqKey="Yang Z" first="Zifeng" last="Yang">Zifeng Yang</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 </wicri:regionArea>
</affiliation>
</author>
<author><name sortKey="Hu, Wenhui" sort="Hu, Wenhui" uniqKey="Hu W" first="Wenhui" last="Hu">Wenhui Hu</name>
<affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</nlm:affiliation>
<country xml:lang="fr" wicri:curation="lc">République populaire de Chine</country>
<wicri:regionArea>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 </wicri:regionArea>
</affiliation>
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<series><title level="j">Journal of medicinal chemistry</title>
<idno type="eISSN">1520-4804</idno>
<imprint><date when="2018" type="published">2018</date>
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<term>Amantadine (pharmacology)</term>
<term>Antiviral Agents (chemistry)</term>
<term>Antiviral Agents (pharmacology)</term>
<term>Dose-Response Relationship, Drug</term>
<term>Drug Discovery</term>
<term>Drug Resistance, Viral (drug effects)</term>
<term>Enzyme Inhibitors (chemistry)</term>
<term>Enzyme Inhibitors (pharmacology)</term>
<term>Hemagglutinins (metabolism)</term>
<term>Imidazoles (chemistry)</term>
<term>Imidazoles (pharmacology)</term>
<term>Influenza A virus (drug effects)</term>
<term>Influenza A virus (enzymology)</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Conformation</term>
<term>Neuraminidase (antagonists & inhibitors)</term>
<term>Neuraminidase (metabolism)</term>
<term>Oseltamivir (chemistry)</term>
<term>Oseltamivir (pharmacology)</term>
<term>Structure-Activity Relationship</term>
</keywords>
<keywords scheme="KwdFr" xml:lang="fr"><term>Amantadine ()</term>
<term>Amantadine (pharmacologie)</term>
<term>Antienzymes ()</term>
<term>Antienzymes (pharmacologie)</term>
<term>Antiviraux ()</term>
<term>Antiviraux (pharmacologie)</term>
<term>Conformation moléculaire</term>
<term>Découverte de médicament</term>
<term>Hémagglutinines (métabolisme)</term>
<term>Imidazoles ()</term>
<term>Imidazoles (pharmacologie)</term>
<term>Oséltamivir ()</term>
<term>Oséltamivir (pharmacologie)</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Résistance virale aux médicaments ()</term>
<term>Sialidase (antagonistes et inhibiteurs)</term>
<term>Sialidase (métabolisme)</term>
<term>Tests de sensibilité microbienne</term>
<term>Virus de la grippe A ()</term>
<term>Virus de la grippe A (enzymologie)</term>
</keywords>
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</keywords>
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<term>Antiviral Agents</term>
<term>Enzyme Inhibitors</term>
<term>Imidazoles</term>
<term>Oseltamivir</term>
</keywords>
<keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Hemagglutinins</term>
<term>Neuraminidase</term>
</keywords>
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<term>Antiviral Agents</term>
<term>Enzyme Inhibitors</term>
<term>Imidazoles</term>
<term>Oseltamivir</term>
</keywords>
<keywords scheme="MESH" qualifier="antagonistes et inhibiteurs" xml:lang="fr"><term>Sialidase</term>
</keywords>
<keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Drug Resistance, Viral</term>
<term>Influenza A virus</term>
</keywords>
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</keywords>
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<term>Antiviraux</term>
<term>Imidazoles</term>
<term>Oséltamivir</term>
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<term>Drug Discovery</term>
<term>Microbial Sensitivity Tests</term>
<term>Molecular Conformation</term>
<term>Structure-Activity Relationship</term>
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<term>Antienzymes</term>
<term>Antiviraux</term>
<term>Conformation moléculaire</term>
<term>Découverte de médicament</term>
<term>Imidazoles</term>
<term>Oséltamivir</term>
<term>Relation dose-effet des médicaments</term>
<term>Relation structure-activité</term>
<term>Résistance virale aux médicaments</term>
<term>Tests de sensibilité microbienne</term>
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<front><div type="abstract" xml:lang="en">Influenza pandemic is a constant major threat to public health caused by influenza A viruses (IAVs). IAVs are subcategorized by the surface proteins hemagglutinin (HA) and neuraminidase (NA), in which they are both essential targets for drug discovery. While it is of great concern that NA inhibitor oseltamivir resistant strains are frequently identified from human or avian influenza virus, structural and functional characterization of influenza HA has raised hopes for new antiviral therapies. In this study, we explored a structure-activity relationship (SAR) of pinanamine-based antivirals and discovered a potent inhibitor M090 against amantadine-resistant viruses, including the 2009 H1N1 pandemic strains, and oseltamivir-resistant viruses. Mechanism of action studies, particularly hemolysis inhibition, indicated that M090 targets influenza HA and it occupied a highly conserved pocket of the HA<sub>2</sub>
 domain and inhibited virus-mediated membrane fusion by "locking" the bending state of HA<sub>2</sub>
 during the conformational rearrangement process. This work provides new binding sites within the HA protein and indicates that this pocket may be a promising target for broad-spectrum anti-influenza A drug design and development.</div>
</front>
</TEI>
<pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">29799746</PMID>
<DateCompleted><Year>2019</Year>
<Month>09</Month>
<Day>23</Day>
</DateCompleted>
<DateRevised><Year>2020</Year>
<Month>03</Month>
<Day>06</Day>
</DateRevised>
<Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-4804</ISSN>
<JournalIssue CitedMedium="Internet"><Volume>61</Volume>
<Issue>12</Issue>
<PubDate><Year>2018</Year>
<Month>06</Month>
<Day>28</Day>
</PubDate>
</JournalIssue>
<Title>Journal of medicinal chemistry</Title>
<ISOAbbreviation>J. Med. Chem.</ISOAbbreviation>
</Journal>
<ArticleTitle>Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.</ArticleTitle>
<Pagination><MedlinePgn>5187-5198</MedlinePgn>
</Pagination>
<ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jmedchem.8b00042</ELocationID>
<Abstract><AbstractText>Influenza pandemic is a constant major threat to public health caused by influenza A viruses (IAVs). IAVs are subcategorized by the surface proteins hemagglutinin (HA) and neuraminidase (NA), in which they are both essential targets for drug discovery. While it is of great concern that NA inhibitor oseltamivir resistant strains are frequently identified from human or avian influenza virus, structural and functional characterization of influenza HA has raised hopes for new antiviral therapies. In this study, we explored a structure-activity relationship (SAR) of pinanamine-based antivirals and discovered a potent inhibitor M090 against amantadine-resistant viruses, including the 2009 H1N1 pandemic strains, and oseltamivir-resistant viruses. Mechanism of action studies, particularly hemolysis inhibition, indicated that M090 targets influenza HA and it occupied a highly conserved pocket of the HA<sub>2</sub>
 domain and inhibited virus-mediated membrane fusion by "locking" the bending state of HA<sub>2</sub>
 during the conformational rearrangement process. This work provides new binding sites within the HA protein and indicates that this pocket may be a promising target for broad-spectrum anti-influenza A drug design and development.</AbstractText>
</Abstract>
<AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Zhao</LastName>
<ForeName>Xin</ForeName>
<Initials>X</Initials>
<Identifier Source="ORCID">0000-0002-6659-3748</Identifier>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Li</LastName>
<ForeName>Runfeng</ForeName>
<Initials>R</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Zhou</LastName>
<ForeName>Yang</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 , Sweden.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Xiao</LastName>
<ForeName>Mengjie</ForeName>
<Initials>M</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Ma</LastName>
<ForeName>Chunlong</ForeName>
<Initials>C</Initials>
<AffiliationInfo><Affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>BIO5 Institute , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Yang</LastName>
<ForeName>Zhongjin</ForeName>
<Initials>Z</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Zeng</LastName>
<ForeName>Shaogao</ForeName>
<Initials>S</Initials>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Du</LastName>
<ForeName>Qiuling</ForeName>
<Initials>Q</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Yang</LastName>
<ForeName>Chunguang</ForeName>
<Initials>C</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Jiang</LastName>
<ForeName>Haiming</ForeName>
<Initials>H</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Hu</LastName>
<ForeName>Yanmei</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>BIO5 Institute , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Wang</LastName>
<ForeName>Kefeng</ForeName>
<Initials>K</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Mok</LastName>
<ForeName>Chris Ka Pun</ForeName>
<Initials>CKP</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>HKU-Pasteur Research Pole, School of Public Health, HKU Li Ka Shing Faculty of Medicine , The University of Hong Kong , 5 Sassoon Road , Pokfulam , Hong Kong.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Sun</LastName>
<ForeName>Ping</ForeName>
<Initials>P</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Dong</LastName>
<ForeName>Jianghong</ForeName>
<Initials>J</Initials>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Cui</LastName>
<ForeName>Wei</ForeName>
<Initials>W</Initials>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Wang</LastName>
<ForeName>Jun</ForeName>
<Initials>J</Initials>
<Identifier Source="ORCID">0000-0002-4845-4621</Identifier>
<AffiliationInfo><Affiliation>Department of Pharmacology and Toxicology, College of Pharmacy , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>BIO5 Institute , The University of Arizona , Tucson , Arizona 85721 , United States.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Tu</LastName>
<ForeName>Yaoquan</ForeName>
<Initials>Y</Initials>
<AffiliationInfo><Affiliation>Division of Theoretical Chemistry and Biology, School of Biotechnology , Royal Institute of Technology (KTH), AlbaNova University Center , Stockholm SE-100 44 , Sweden.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Yang</LastName>
<ForeName>Zifeng</ForeName>
<Initials>Z</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, National Clinical Research Center for Respiratory Disease, Guangzhou Institute of Respiratory Health, The First Affiliated Hospital , Guangzhou Medical University , Guangzhou 510120 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
<Author ValidYN="Y"><LastName>Hu</LastName>
<ForeName>Wenhui</ForeName>
<Initials>W</Initials>
<AffiliationInfo><Affiliation>State Key Laboratory of Respiratory Disease, Key Laboratory of Molecular Target & Clinical Pharmacology, School of Pharmaceutical Sciences & The Fifth Affiliated Hospital , Guangzhou Medical University , Guangzhou 511436 , P. R. China.</Affiliation>
</AffiliationInfo>
<AffiliationInfo><Affiliation>Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences , Guangzhou 510530 , P. R. China.</Affiliation>
</AffiliationInfo>
</Author>
</AuthorList>
<Language>eng</Language>
<GrantList CompleteYN="Y"><Grant><GrantID>R21 AI119187</GrantID>
<Acronym>AI</Acronym>
<Agency>NIAID NIH HHS</Agency>
<Country>United States</Country>
</Grant>
<Grant><GrantID>R33 AI119187</GrantID>
<Acronym>AI</Acronym>
<Agency>NIAID NIH HHS</Agency>
<Country>United States</Country>
</Grant>
</GrantList>
<PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType>
<PublicationType UI="D052061">Research Support, N.I.H., Extramural</PublicationType>
<PublicationType UI="D013485">Research Support, Non-U.S. Gov't</PublicationType>
</PublicationTypeList>
<ArticleDate DateType="Electronic"><Year>2018</Year>
<Month>06</Month>
<Day>11</Day>
</ArticleDate>
</Article>
<MedlineJournalInfo><Country>United States</Country>
<MedlineTA>J Med Chem</MedlineTA>
<NlmUniqueID>9716531</NlmUniqueID>
<ISSNLinking>0022-2623</ISSNLinking>
</MedlineJournalInfo>
<ChemicalList><Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D004791">Enzyme Inhibitors</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D006388">Hemagglutinins</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="D007093">Imidazoles</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>0</RegistryNumber>
<NameOfSubstance UI="C000611547">pinanamine</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>20O93L6F9H</RegistryNumber>
<NameOfSubstance UI="D053139">Oseltamivir</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>BF4C9Z1J53</RegistryNumber>
<NameOfSubstance UI="D000547">Amantadine</NameOfSubstance>
</Chemical>
<Chemical><RegistryNumber>EC 3.2.1.18</RegistryNumber>
<NameOfSubstance UI="D009439">Neuraminidase</NameOfSubstance>
</Chemical>
</ChemicalList>
<CitationSubset>IM</CitationSubset>
<MeshHeadingList><MeshHeading><DescriptorName UI="D000547" MajorTopicYN="N">Amantadine</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004305" MajorTopicYN="N">Dose-Response Relationship, Drug</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D055808" MajorTopicYN="Y">Drug Discovery</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D024882" MajorTopicYN="N">Drug Resistance, Viral</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D004791" MajorTopicYN="N">Enzyme Inhibitors</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D006388" MajorTopicYN="N">Hemagglutinins</DescriptorName>
<QualifierName UI="Q000378" MajorTopicYN="N">metabolism</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D007093" MajorTopicYN="N">Imidazoles</DescriptorName>
<QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName>
<QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D009980" MajorTopicYN="N">Influenza A virus</DescriptorName>
<QualifierName UI="Q000187" MajorTopicYN="Y">drug effects</QualifierName>
<QualifierName UI="Q000201" MajorTopicYN="N">enzymology</QualifierName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008826" MajorTopicYN="N">Microbial Sensitivity Tests</DescriptorName>
</MeshHeading>
<MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName>
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Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.

Discovery of Highly Potent Pinanamine-Based Inhibitors against Amantadine- and Oseltamivir-Resistant Influenza A Viruses.

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