Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Identifieur interne : 000189 ( Main/Exploration ); précédent : 000188; suivant : 000190Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Auteurs : Yixian Liao [République populaire de Chine] ; Yilu Ye [République populaire de Chine] ; Sumei Li [République populaire de Chine] ; Yilian Zhuang [République populaire de Chine] ; Liye Chen [République populaire de Chine] ; Jianxin Chen [République populaire de Chine] ; Zining Cui [République populaire de Chine] ; Lijian Huo [République populaire de Chine] ; Shuwen Liu [République populaire de Chine] ; Gaopeng Song [République populaire de Chine]Source :
- European journal of medicinal chemistry [ 1768-3254 ] ; 2020.
Abstract
Currently, influenza PAN endonuclease has become an attractive target for development of new drugs to treat influenza infections. Herein we report the discovery of new PAN endonuclease inhibitors derived from a chelating agent dopamine moiety. A series of dopamine amide derivatives and their conformationally constrained 1,2,3,4-tetrahydroisoquinoline-6,7-diol-based analogs were elaborated and assayed against influenza virus A/WSN/33 (H1N1). Most compounds exhibited moderate to excellent antiviral activities, generating a preliminary SARs. Among them, compounds 14 and 19 showed stronger anti-IAV activity compared with the reference Peramivir. Moreover, 14 and 19 demonstrated a concentration-dependent inhibition of PAN endonuclease based on both FRET assay and SPR assay. Docking studies were also performed to elucidate the binding mode of 14 and 19 with the PAN protein and to identify amino acids involved in their mechanism of action, which were well consistent with the biological data. This finding was beneficial to laying the foundation for the rational development of more effective PAN endonuclease inhibitors.
DOI: 10.1016/j.ejmech.2020.112048
PubMed: 31954881
Affiliations:
Links toward previous steps (curation, corpus...)
- to stream PubMed, to step Corpus: 000845
- to stream PubMed, to step Curation: 000845
- to stream PubMed, to step Checkpoint: 000156
- to stream Ncbi, to step Merge: 003121
- to stream Ncbi, to step Curation: 003121
- to stream Ncbi, to step Checkpoint: 003121
- to stream Main, to step Merge: 000189
- to stream Main, to step Curation: 000189
Le document en format XML
<record><TEI><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PA<sub>N</sub> endonuclease.</title><author><name sortKey="Liao, Yixian" sort="Liao, Yixian" uniqKey="Liao Y" first="Yixian" last="Liao">Yixian Liao</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China; State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China; State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Ye, Yilu" sort="Ye, Yilu" uniqKey="Ye Y" first="Yilu" last="Ye">Yilu Ye</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author><author><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632</wicri:regionArea><wicri:noRegion>510632</wicri:noRegion></affiliation></author><author><name sortKey="Zhuang, Yilian" sort="Zhuang, Yilian" uniqKey="Zhuang Y" first="Yilian" last="Zhuang">Yilian Zhuang</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Liye" sort="Chen, Liye" uniqKey="Chen L" first="Liye" last="Chen">Liye Chen</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><affiliation wicri:level="1"><nlm:affiliation>Guangdong Provincial Key Laboratory of Veterinary Pharmaceutics Development and Safety Evaluation, College of Veterinary Medicine, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Guangdong Provincial Key Laboratory of Veterinary Pharmaceutics Development and Safety Evaluation, College of Veterinary Medicine, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Cui, Zining" sort="Cui, Zining" uniqKey="Cui Z" first="Zining" last="Cui">Zining Cui</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Huo, Lijian" sort="Huo, Lijian" uniqKey="Huo L" first="Lijian" last="Huo">Lijian Huo</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author><author><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China. Electronic address: songgp1021@scau.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PubMed</idno><date when="2020">2020</date><idno type="RBID">pubmed:31954881</idno><idno type="pmid">31954881</idno><idno type="doi">10.1016/j.ejmech.2020.112048</idno><idno type="wicri:Area/PubMed/Corpus">000845</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000845</idno><idno type="wicri:Area/PubMed/Curation">000845</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000845</idno><idno type="wicri:Area/PubMed/Checkpoint">000156</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000156</idno><idno type="wicri:Area/Ncbi/Merge">003121</idno><idno type="wicri:Area/Ncbi/Curation">003121</idno><idno type="wicri:Area/Ncbi/Checkpoint">003121</idno><idno type="wicri:Area/Main/Merge">000189</idno><idno type="wicri:Area/Main/Curation">000189</idno><idno type="wicri:Area/Main/Exploration">000189</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en">Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PA<sub>N</sub> endonuclease.</title><author><name sortKey="Liao, Yixian" sort="Liao, Yixian" uniqKey="Liao Y" first="Yixian" last="Liao">Yixian Liao</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China; State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China; State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Ye, Yilu" sort="Ye, Yilu" uniqKey="Ye Y" first="Yilu" last="Ye">Yilu Ye</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author><author><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><affiliation wicri:level="1"><nlm:affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632</wicri:regionArea><wicri:noRegion>510632</wicri:noRegion></affiliation></author><author><name sortKey="Zhuang, Yilian" sort="Zhuang, Yilian" uniqKey="Zhuang Y" first="Yilian" last="Zhuang">Yilian Zhuang</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Liye" sort="Chen, Liye" uniqKey="Chen L" first="Liye" last="Chen">Liye Chen</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><affiliation wicri:level="1"><nlm:affiliation>Guangdong Provincial Key Laboratory of Veterinary Pharmaceutics Development and Safety Evaluation, College of Veterinary Medicine, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Guangdong Provincial Key Laboratory of Veterinary Pharmaceutics Development and Safety Evaluation, College of Veterinary Medicine, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Cui, Zining" sort="Cui, Zining" uniqKey="Cui Z" first="Zining" last="Cui">Zining Cui</name><affiliation wicri:level="1"><nlm:affiliation>State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources, Integrative Microbiology Research Centre, Guangdong Province Key Laboratory of Microbial Signals and Disease Control, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Huo, Lijian" sort="Huo, Lijian" uniqKey="Huo L" first="Lijian" last="Huo">Lijian Huo</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</wicri:noRegion></affiliation></author><author><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><affiliation wicri:level="1"><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515</wicri:regionArea><wicri:noRegion>510515</wicri:noRegion></affiliation></author><author><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name><affiliation wicri:level="1"><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China. Electronic address: songgp1021@scau.edu.cn.</nlm:affiliation><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642</wicri:regionArea><wicri:noRegion>510642</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></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Currently, influenza PA<sub>N</sub> endonuclease has become an attractive target for development of new drugs to treat influenza infections. Herein we report the discovery of new PA<sub>N</sub> endonuclease inhibitors derived from a chelating agent dopamine moiety. A series of dopamine amide derivatives and their conformationally constrained 1,2,3,4-tetrahydroisoquinoline-6,7-diol-based analogs were elaborated and assayed against influenza virus A/WSN/33 (H1N1). Most compounds exhibited moderate to excellent antiviral activities, generating a preliminary SARs. Among them, compounds 14 and 19 showed stronger anti-IAV activity compared with the reference Peramivir. Moreover, 14 and 19 demonstrated a concentration-dependent inhibition of PA<sub>N</sub> endonuclease based on both FRET assay and SPR assay. Docking studies were also performed to elucidate the binding mode of 14 and 19 with the PA<sub>N</sub> protein and to identify amino acids involved in their mechanism of action, which were well consistent with the biological data. This finding was beneficial to laying the foundation for the rational development of more effective PA<sub>N</sub> endonuclease inhibitors.</div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Liao, Yixian" sort="Liao, Yixian" uniqKey="Liao Y" first="Yixian" last="Liao">Yixian Liao</name></noRegion><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><name sortKey="Chen, Liye" sort="Chen, Liye" uniqKey="Chen L" first="Liye" last="Chen">Liye Chen</name><name sortKey="Cui, Zining" sort="Cui, Zining" uniqKey="Cui Z" first="Zining" last="Cui">Zining Cui</name><name sortKey="Huo, Lijian" sort="Huo, Lijian" uniqKey="Huo L" first="Lijian" last="Huo">Lijian Huo</name><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name><name sortKey="Ye, Yilu" sort="Ye, Yilu" uniqKey="Ye Y" first="Yilu" last="Ye">Yilu Ye</name><name sortKey="Zhuang, Yilian" sort="Zhuang, Yilian" uniqKey="Zhuang Y" first="Yilian" last="Zhuang">Yilian Zhuang</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
EXPLOR_STEP=$WICRI_ROOT/Sante/explor/SrasV1/Data/Main/Exploration
HfdSelect -h $EXPLOR_STEP/biblio.hfd -nk 000189 | SxmlIndent | more
Ou
HfdSelect -h $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd -nk 000189 | SxmlIndent | more
Pour mettre un lien sur cette page dans le réseau Wicri
{{Explor lien
|wiki= Sante
|area= SrasV1
|flux= Main
|étape= Exploration
|type= RBID
|clé= pubmed:31954881
|texte= Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
}}
Pour générer des pages wiki
HfdIndexSelect -h $EXPLOR_AREA/Data/Main/Exploration/RBID.i -Sk "pubmed:31954881" \
| HfdSelect -Kh $EXPLOR_AREA/Data/Main/Exploration/biblio.hfd \
| NlmPubMed2Wicri -a SrasV1
| This area was generated with Dilib version V0.6.33. |  |