Discovery of novel 1,2,3-triazole oseltamivir derivatives as potent influenza neuraminidase inhibitors targeting the 430-cavity.
Identifieur interne : 000720 ( 2020/Analysis ); précédent : 000719; suivant : 000721Discovery of novel 1,2,3-triazole oseltamivir derivatives as potent influenza neuraminidase inhibitors targeting the 430-cavity.
Auteurs : Han Ju [République populaire de Chine] ; Siyu Xiu [République populaire de Chine] ; Xiao Ding [République populaire de Chine] ; Min Shang [République populaire de Chine] ; Ruifang Jia [République populaire de Chine] ; Bing Huang [République populaire de Chine] ; Peng Zhan [République populaire de Chine] ; Xinyong Liu [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2020.
Descripteurs français
- KwdFr :
- Animaux, Antienzymes (), Antienzymes (pharmacologie), Antienzymes (synthèse chimique), Antiviraux (), Antiviraux (pharmacologie), Antiviraux (synthèse chimique), Découverte de médicament, Fibroblastes (), Fibroblastes (virologie), Modèles moléculaires, Poulets, Relation dose-effet des médicaments, Relation structure-activité, Sialidase (antagonistes et inhibiteurs), Sialidase (métabolisme), Structure moléculaire, Tests de sensibilité microbienne, Triazoles (), Triazoles (pharmacologie), Triazoles (synthèse chimique), Virus de la grippe A ().
- MESH :
- antagonistes et inhibiteurs : Sialidase.
- métabolisme : Sialidase.
- pharmacologie : Antienzymes, Antiviraux, Triazoles.
- synthèse chimique : Antienzymes, Antiviraux, Triazoles.
- virologie : Fibroblastes.
- Animaux, Antienzymes, Antiviraux, Découverte de médicament, Fibroblastes, Modèles moléculaires, Poulets, Relation dose-effet des médicaments, Relation structure-activité, Structure moléculaire, Tests de sensibilité microbienne, Triazoles, Virus de la grippe A.
English descriptors
- KwdEn :
- Animals, Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Chickens, Dose-Response Relationship, Drug, Drug Discovery, Enzyme Inhibitors (chemical synthesis), Enzyme Inhibitors (chemistry), Enzyme Inhibitors (pharmacology), Fibroblasts (drug effects), Fibroblasts (virology), Influenza A virus (drug effects), Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Neuraminidase (antagonists & inhibitors), Neuraminidase (metabolism), Structure-Activity Relationship, Triazoles (chemical synthesis), Triazoles (chemistry), Triazoles (pharmacology).
- MESH :
- chemical , antagonists & inhibitors : Neuraminidase.
- chemical , chemical synthesis : Antiviral Agents, Enzyme Inhibitors, Triazoles.
- chemical , chemistry : Antiviral Agents, Enzyme Inhibitors, Triazoles.
- chemical , metabolism : Neuraminidase.
- chemical , pharmacology : Antiviral Agents, Enzyme Inhibitors, Triazoles.
- drug effects : Fibroblasts, Influenza A virus.
- virology : Fibroblasts.
- Animals, Chickens, Dose-Response Relationship, Drug, Drug Discovery, Microbial Sensitivity Tests, Models, Molecular, Molecular Structure, Structure-Activity Relationship.
Abstract
A novel series of 1,2,3-triazole oseltamivir derivatives, which could simultaneously occupy the classical NA catalytic site and the newly reported 430-cavity, were designed, synthesized, and evaluated for their anti-influenza activities. The results demonstrated that four compounds (6g, 6l, 6y and 8c) showed robust anti-influenza potencies against H5N1, H5N2 and H5N6 strains in both enzymatic assay and cellular assay. Especially, 6l was proved to possess the most potent and broad-spectrum anti-influenza activity, with IC50 values of 0.12 μM, 0.049 μM and 0.16 μM and EC50 values of 2.45 μM, 0.43 μM and 2.8 μM against H5N1, H5N2 and H5N6 strains, respectively, which were slightly weaker than oseltamivir carboxylate. In addition, in the embryonated egg model, 6l achieved the similar protective effect against H9N2 strain with oseltamivir carboxylate in the tested concentrations. Preliminary structure-activity relationships (SARs), molecular modeling, and calculated physicochemical properties of selected compounds were also discussed.
DOI: 10.1016/j.ejmech.2019.111940
PubMed: 31835169
Affiliations:
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pubmed:31835169Le document en format XML
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China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Xiu, Siyu" sort="Xiu, Siyu" uniqKey="Xiu S" first="Siyu" last="Xiu">Siyu Xiu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Ding, Xiao" sort="Ding, Xiao" uniqKey="Ding X" first="Xiao" last="Ding">Xiao Ding</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Shang, Min" sort="Shang, Min" uniqKey="Shang M" first="Min" last="Shang">Min Shang</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Poultry Science, Shandong Academy of Agricultural Sciences, 1, Jiaoxiao Road, 250023, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Poultry Science, Shandong Academy of Agricultural Sciences, 1, Jiaoxiao Road, 250023, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Jia, Ruifang" sort="Jia, Ruifang" uniqKey="Jia R" first="Ruifang" last="Jia">Ruifang Jia</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Huang, Bing" sort="Huang, Bing" uniqKey="Huang B" first="Bing" last="Huang">Bing Huang</name><affiliation wicri:level="1"><nlm:affiliation>Institute of Poultry Science, Shandong Academy of Agricultural Sciences, 1, Jiaoxiao Road, 250023, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Institute of Poultry Science, Shandong Academy of Agricultural Sciences, 1, Jiaoxiao Road, 250023, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong, PR China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><affiliation wicri:level="1"><nlm:affiliation>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong, PR China. Electronic address: xinyongl@sdu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), School of Pharmaceutical Sciences, Shandong University, 44 West Culture Road, 250012, Jinan, Shandong</wicri:regionArea><wicri:noRegion>Shandong</wicri:noRegion></affiliation></author></analytic><series><title level="j">European journal of medicinal chemistry</title><idno type="eISSN">1768-3254</idno><imprint><date when="2020" type="published">2020</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>Chickens</term><term>Dose-Response Relationship, Drug</term><term>Drug Discovery</term><term>Enzyme Inhibitors (chemical synthesis)</term><term>Enzyme Inhibitors (chemistry)</term><term>Enzyme Inhibitors (pharmacology)</term><term>Fibroblasts (drug effects)</term><term>Fibroblasts (virology)</term><term>Influenza A virus (drug effects)</term><term>Microbial Sensitivity Tests</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Neuraminidase (antagonists & inhibitors)</term><term>Neuraminidase (metabolism)</term><term>Structure-Activity Relationship</term><term>Triazoles (chemical synthesis)</term><term>Triazoles (chemistry)</term><term>Triazoles (pharmacology)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Animaux</term><term>Antienzymes ()</term><term>Antienzymes (pharmacologie)</term><term>Antienzymes (synthèse chimique)</term><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Antiviraux (synthèse chimique)</term><term>Découverte de médicament</term><term>Fibroblastes ()</term><term>Fibroblastes (virologie)</term><term>Modèles moléculaires</term><term>Poulets</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Sialidase (antagonistes et inhibiteurs)</term><term>Sialidase (métabolisme)</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term><term>Triazoles ()</term><term>Triazoles (pharmacologie)</term><term>Triazoles (synthèse chimique)</term><term>Virus de la grippe A ()</term></keywords><keywords scheme="MESH" type="chemical" qualifier="antagonists & inhibitors" xml:lang="en"><term>Neuraminidase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemical synthesis" xml:lang="en"><term>Antiviral Agents</term><term>Enzyme Inhibitors</term><term>Triazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Enzyme Inhibitors</term><term>Triazoles</term></keywords><keywords scheme="MESH" type="chemical" qualifier="metabolism" xml:lang="en"><term>Neuraminidase</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Enzyme Inhibitors</term><term>Triazoles</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>Fibroblasts</term><term>Influenza A virus</term></keywords><keywords scheme="MESH" qualifier="métabolisme" xml:lang="fr"><term>Sialidase</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antienzymes</term><term>Antiviraux</term><term>Triazoles</term></keywords><keywords scheme="MESH" qualifier="synthèse chimique" xml:lang="fr"><term>Antienzymes</term><term>Antiviraux</term><term>Triazoles</term></keywords><keywords scheme="MESH" qualifier="virologie" xml:lang="fr"><term>Fibroblastes</term></keywords><keywords scheme="MESH" qualifier="virology" xml:lang="en"><term>Fibroblasts</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Animals</term><term>Chickens</term><term>Dose-Response Relationship, Drug</term><term>Drug Discovery</term><term>Microbial Sensitivity Tests</term><term>Models, Molecular</term><term>Molecular Structure</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Animaux</term><term>Antienzymes</term><term>Antiviraux</term><term>Découverte de médicament</term><term>Fibroblastes</term><term>Modèles moléculaires</term><term>Poulets</term><term>Relation dose-effet des médicaments</term><term>Relation structure-activité</term><term>Structure moléculaire</term><term>Tests de sensibilité microbienne</term><term>Triazoles</term><term>Virus de la grippe A</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">A novel series of 1,2,3-triazole oseltamivir derivatives, which could simultaneously occupy the classical NA catalytic site and the newly reported 430-cavity, were designed, synthesized, and evaluated for their anti-influenza activities. The results demonstrated that four compounds (6g, 6l, 6y and 8c) showed robust anti-influenza potencies against H5N1, H5N2 and H5N6 strains in both enzymatic assay and cellular assay. Especially, 6l was proved to possess the most potent and broad-spectrum anti-influenza activity, with IC<sub>50</sub> values of 0.12 μM, 0.049 μM and 0.16 μM and EC<sub>50</sub> values of 2.45 μM, 0.43 μM and 2.8 μM against H5N1, H5N2 and H5N6 strains, respectively, which were slightly weaker than oseltamivir carboxylate. In addition, in the embryonated egg model, 6l achieved the similar protective effect against H9N2 strain with oseltamivir carboxylate in the tested concentrations. Preliminary structure-activity relationships (SARs), molecular modeling, and calculated physicochemical properties of selected compounds were also discussed.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Ju, Han" sort="Ju, Han" uniqKey="Ju H" first="Han" last="Ju">Han Ju</name></noRegion><name sortKey="Ding, Xiao" sort="Ding, Xiao" uniqKey="Ding X" first="Xiao" last="Ding">Xiao Ding</name><name sortKey="Huang, Bing" sort="Huang, Bing" uniqKey="Huang B" first="Bing" last="Huang">Bing Huang</name><name sortKey="Jia, Ruifang" sort="Jia, Ruifang" uniqKey="Jia R" first="Ruifang" last="Jia">Ruifang Jia</name><name sortKey="Liu, Xinyong" sort="Liu, Xinyong" uniqKey="Liu X" first="Xinyong" last="Liu">Xinyong Liu</name><name sortKey="Shang, Min" sort="Shang, Min" uniqKey="Shang M" first="Min" last="Shang">Min Shang</name><name sortKey="Xiu, Siyu" sort="Xiu, Siyu" uniqKey="Xiu S" first="Siyu" last="Xiu">Siyu Xiu</name><name sortKey="Zhan, Peng" sort="Zhan, Peng" uniqKey="Zhan P" first="Peng" last="Zhan">Peng Zhan</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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