Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Identifieur interne : 000845 ( PubMed/Corpus ); précédent : 000844; suivant : 000846Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PAN endonuclease.
Auteurs : Yixian Liao ; Yilu Ye ; Sumei Li ; Yilian Zhuang ; Liye Chen ; Jianxin Chen ; Zining Cui ; Lijian Huo ; Shuwen Liu ; Gaopeng SongSource :
- 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
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<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><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></affiliation></author><author><name sortKey="Ye, Yilu" sort="Ye, Yilu" uniqKey="Ye Y" first="Yilu" last="Ye">Yilu Ye</name><affiliation><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation></affiliation></author><author><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><affiliation><nlm:affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</nlm:affiliation></affiliation></author><author><name sortKey="Zhuang, Yilian" sort="Zhuang, Yilian" uniqKey="Zhuang Y" first="Yilian" last="Zhuang">Yilian Zhuang</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Chen, Liye" sort="Chen, Liye" uniqKey="Chen L" first="Liye" last="Chen">Liye Chen</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><affiliation><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></affiliation></author><author><name sortKey="Cui, Zining" sort="Cui, Zining" uniqKey="Cui Z" first="Zining" last="Cui">Zining Cui</name><affiliation><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></affiliation></author><author><name sortKey="Huo, Lijian" sort="Huo, Lijian" uniqKey="Huo L" first="Lijian" last="Huo">Lijian Huo</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><affiliation><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation></affiliation></author><author><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China. Electronic address: songgp1021@scau.edu.cn.</nlm:affiliation></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></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><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></affiliation></author><author><name sortKey="Ye, Yilu" sort="Ye, Yilu" uniqKey="Ye Y" first="Yilu" last="Ye">Yilu Ye</name><affiliation><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</nlm:affiliation></affiliation></author><author><name sortKey="Li, Sumei" sort="Li, Sumei" uniqKey="Li S" first="Sumei" last="Li">Sumei Li</name><affiliation><nlm:affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</nlm:affiliation></affiliation></author><author><name sortKey="Zhuang, Yilian" sort="Zhuang, Yilian" uniqKey="Zhuang Y" first="Yilian" last="Zhuang">Yilian Zhuang</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Chen, Liye" sort="Chen, Liye" uniqKey="Chen L" first="Liye" last="Chen">Liye Chen</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Chen, Jianxin" sort="Chen, Jianxin" uniqKey="Chen J" first="Jianxin" last="Chen">Jianxin Chen</name><affiliation><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></affiliation></author><author><name sortKey="Cui, Zining" sort="Cui, Zining" uniqKey="Cui Z" first="Zining" last="Cui">Zining Cui</name><affiliation><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></affiliation></author><author><name sortKey="Huo, Lijian" sort="Huo, Lijian" uniqKey="Huo L" first="Lijian" last="Huo">Lijian Huo</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</nlm:affiliation></affiliation></author><author><name sortKey="Liu, Shuwen" sort="Liu, Shuwen" uniqKey="Liu S" first="Shuwen" last="Liu">Shuwen Liu</name><affiliation><nlm:affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</nlm:affiliation></affiliation></author><author><name sortKey="Song, Gaopeng" sort="Song, Gaopeng" uniqKey="Song G" first="Gaopeng" last="Song">Gaopeng Song</name><affiliation><nlm:affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China. Electronic address: songgp1021@scau.edu.cn.</nlm:affiliation></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><pubmed><MedlineCitation Status="In-Process" Owner="NLM"><PMID Version="1">31954881</PMID><DateRevised><Year>2020</Year><Month>02</Month><Day>18</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1768-3254</ISSN><JournalIssue CitedMedium="Internet"><Volume>189</Volume><PubDate><Year>2020</Year><Month>Mar</Month><Day>01</Day></PubDate></JournalIssue><Title>European journal of medicinal chemistry</Title><ISOAbbreviation>Eur J Med Chem</ISOAbbreviation></Journal><ArticleTitle>Synthesis and SARs of dopamine derivatives as potential inhibitors of influenza virus PA<sub>N</sub> endonuclease.</ArticleTitle><Pagination><MedlinePgn>112048</MedlinePgn></Pagination><ELocationID EIdType="pii" ValidYN="Y">S0223-5234(20)30015-5</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.1016/j.ejmech.2020.112048</ELocationID><Abstract><AbstractText>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.</AbstractText><CopyrightInformation>Copyright © 2020 Elsevier Masson SAS. All rights reserved.</CopyrightInformation></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Liao</LastName><ForeName>Yixian</ForeName><Initials>Y</Initials><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Ye</LastName><ForeName>Yilu</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Sumei</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>Department of Human Anatomy, School of Medicine, Jinan University, Guangzhou, 510632, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhuang</LastName><ForeName>Yilian</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Liye</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chen</LastName><ForeName>Jianxin</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>Guangdong Provincial Key Laboratory of Veterinary Pharmaceutics Development and Safety Evaluation, College of Veterinary Medicine, South China Agricultural University, Guangzhou, 510642, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Cui</LastName><ForeName>Zining</ForeName><Initials>Z</Initials><AffiliationInfo><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.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Huo</LastName><ForeName>Lijian</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Liu</LastName><ForeName>Shuwen</ForeName><Initials>S</Initials><AffiliationInfo><Affiliation>School of Pharmaceutical Sciences, Southern Medical University, Guangzhou, 510515, China. Electronic address: liusw@smu.edu.cn.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Song</LastName><ForeName>Gaopeng</ForeName><Initials>G</Initials><AffiliationInfo><Affiliation>College of Materials and Energy, South China Agricultural University, Guangzhou, 510642, China. Electronic address: songgp1021@scau.edu.cn.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2020</Year><Month>01</Month><Day>11</Day></ArticleDate></Article><MedlineJournalInfo><Country>France</Country><MedlineTA>Eur J Med Chem</MedlineTA><NlmUniqueID>0420510</NlmUniqueID><ISSNLinking>0223-5234</ISSNLinking></MedlineJournalInfo><CitationSubset>IM</CitationSubset><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">Influenza a virus</Keyword><Keyword MajorTopicYN="N">PA(N) endonuclease inhibitors</Keyword><Keyword MajorTopicYN="N">Polyphenols</Keyword><Keyword MajorTopicYN="N">SARs</Keyword></KeywordList><CoiStatement>Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.</CoiStatement></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>11</Month><Day>25</Day></PubMedPubDate><PubMedPubDate PubStatus="revised"><Year>2020</Year><Month>01</Month><Day>07</Day></PubMedPubDate><PubMedPubDate PubStatus="accepted"><Year>2020</Year><Month>01</Month><Day>07</Day></PubMedPubDate><PubMedPubDate PubStatus="pubmed"><Year>2020</Year><Month>1</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="medline"><Year>2020</Year><Month>1</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate><PubMedPubDate PubStatus="entrez"><Year>2020</Year><Month>1</Month><Day>20</Day><Hour>6</Hour><Minute>0</Minute></PubMedPubDate></History><PublicationStatus>ppublish</PublicationStatus><ArticleIdList><ArticleId IdType="pubmed">31954881</ArticleId><ArticleId IdType="pii">S0223-5234(20)30015-5</ArticleId><ArticleId IdType="doi">10.1016/j.ejmech.2020.112048</ArticleId></ArticleIdList></PubmedData></pubmed></record>Pour manipuler ce document sous Unix (Dilib)
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