5'-Silylated 3'-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus.
Identifieur interne : 000E26 ( PubMed/Corpus ); précédent : 000E25; suivant : 000E275'-Silylated 3'-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus.
Auteurs : Sanjeev Kumar V. Vernekar ; Li Qiu ; Jing Zhang ; Jayakanth Kankanala ; Hongmin Li ; Robert J. Geraghty ; Zhengqiang WangSource :
- Journal of medicinal chemistry [ 1520-4804 ] ; 2015.
English descriptors
- KwdEn :
- Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Binding, Competitive, Dengue Virus (drug effects), Dose-Response Relationship, Drug, HIV-1 (drug effects), Methyltransferases (chemistry), Molecular Docking Simulation, S-Adenosylmethionine (chemistry), Silanes (chemistry), Silanes (pharmacology), Stereoisomerism, Structure-Activity Relationship, Triazoles (chemistry), Triazoles (pharmacology), West Nile virus (drug effects), Zidovudine (analogs & derivatives), Zidovudine (chemistry), Zidovudine (pharmacology).
- MESH :
- chemical , analogs & derivatives : Zidovudine.
- chemical , chemistry : Antiviral Agents, Methyltransferases, S-Adenosylmethionine, Silanes, Triazoles, Zidovudine.
- chemical , pharmacology : Antiviral Agents, Silanes, Triazoles, Zidovudine.
- drug effects : Dengue Virus, HIV-1, West Nile virus.
- Binding, Competitive, Dose-Response Relationship, Drug, Molecular Docking Simulation, Stereoisomerism, Structure-Activity Relationship.
Abstract
West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5'-silylated nucleoside scaffold derived from 3'-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure-activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5'-silyl group and the substituent of 3'-triazole or its bioisosteres. Particularly interesting is the 5' silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive S-adenosyl-l-methionine (SAM) binding assay suggest that these compounds likely confer antiviral activity via binding to methyltransferase (MTase).
DOI: 10.1021/acs.jmedchem.5b00327
PubMed: 25909386
Links to Exploration step
pubmed:25909386Le document en format XML
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Vernekar</name><affiliation><nlm:affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Qiu, Li" sort="Qiu, Li" uniqKey="Qiu L" first="Li" last="Qiu">Li Qiu</name><affiliation><nlm:affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Zhang, Jing" sort="Zhang, Jing" uniqKey="Zhang J" first="Jing" last="Zhang">Jing Zhang</name><affiliation><nlm:affiliation>‡Wadsworth Center, New York State Department of Health, 120 New Scotland Ave., Albany, New York 12208, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Kankanala, Jayakanth" sort="Kankanala, Jayakanth" uniqKey="Kankanala J" first="Jayakanth" last="Kankanala">Jayakanth Kankanala</name><affiliation><nlm:affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Li, Hongmin" sort="Li, Hongmin" uniqKey="Li H" first="Hongmin" last="Li">Hongmin Li</name><affiliation><nlm:affiliation>‡Wadsworth Center, New York State Department of Health, 120 New Scotland Ave., Albany, New York 12208, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Geraghty, Robert J" sort="Geraghty, Robert J" uniqKey="Geraghty R" first="Robert J" last="Geraghty">Robert J. 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Geraghty</name><affiliation><nlm:affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</nlm:affiliation></affiliation></author><author><name sortKey="Wang, Zhengqiang" sort="Wang, Zhengqiang" uniqKey="Wang Z" first="Zhengqiang" last="Wang">Zhengqiang Wang</name><affiliation><nlm:affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</nlm:affiliation></affiliation></author></analytic><series><title level="j">Journal of medicinal chemistry</title><idno type="eISSN">1520-4804</idno><imprint><date when="2015" type="published">2015</date></imprint></series></biblStruct></sourceDesc></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Antiviral Agents (chemistry)</term><term>Antiviral Agents (pharmacology)</term><term>Binding, Competitive</term><term>Dengue Virus (drug effects)</term><term>Dose-Response Relationship, Drug</term><term>HIV-1 (drug effects)</term><term>Methyltransferases (chemistry)</term><term>Molecular Docking Simulation</term><term>S-Adenosylmethionine (chemistry)</term><term>Silanes (chemistry)</term><term>Silanes (pharmacology)</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term><term>Triazoles (chemistry)</term><term>Triazoles (pharmacology)</term><term>West Nile virus (drug effects)</term><term>Zidovudine (analogs & derivatives)</term><term>Zidovudine (chemistry)</term><term>Zidovudine (pharmacology)</term></keywords><keywords scheme="MESH" type="chemical" qualifier="analogs & derivatives" xml:lang="en"><term>Zidovudine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Methyltransferases</term><term>S-Adenosylmethionine</term><term>Silanes</term><term>Triazoles</term><term>Zidovudine</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Silanes</term><term>Triazoles</term><term>Zidovudine</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Dengue Virus</term><term>HIV-1</term><term>West Nile virus</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Binding, Competitive</term><term>Dose-Response Relationship, Drug</term><term>Molecular Docking Simulation</term><term>Stereoisomerism</term><term>Structure-Activity Relationship</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5'-silylated nucleoside scaffold derived from 3'-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure-activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5'-silyl group and the substituent of 3'-triazole or its bioisosteres. Particularly interesting is the 5' silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive S-adenosyl-l-methionine (SAM) binding assay suggest that these compounds likely confer antiviral activity via binding to methyltransferase (MTase). </div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">25909386</PMID><DateCompleted><Year>2015</Year><Month>08</Month><Day>06</Day></DateCompleted><DateRevised><Year>2018</Year><Month>11</Month><Day>13</Day></DateRevised><Article PubModel="Print-Electronic"><Journal><ISSN IssnType="Electronic">1520-4804</ISSN><JournalIssue CitedMedium="Internet"><Volume>58</Volume><Issue>9</Issue><PubDate><Year>2015</Year><Month>May</Month><Day>14</Day></PubDate></JournalIssue><Title>Journal of medicinal chemistry</Title><ISOAbbreviation>J. Med. Chem.</ISOAbbreviation></Journal><ArticleTitle>5'-Silylated 3'-1,2,3-triazolyl Thymidine Analogues as Inhibitors of West Nile Virus and Dengue Virus.</ArticleTitle><Pagination><MedlinePgn>4016-28</MedlinePgn></Pagination><ELocationID EIdType="doi" ValidYN="Y">10.1021/acs.jmedchem.5b00327</ELocationID><Abstract><AbstractText>West Nile virus (WNV) and Dengue virus (DENV) are important human pathogens for which there are presently no vaccine or specific antivirals. We report herein a 5'-silylated nucleoside scaffold derived from 3'-azidothymidine (AZT) consistently and selectively inhibiting WNV and DENV at low micromolar concentrations. Further synthesis of various triazole bioisosteres demonstrated clear structure-activity relationships (SARs) in which the antiviral activity against WNV and DENV hinges largely on both the 5'-silyl group and the substituent of 3'-triazole or its bioisosteres. Particularly interesting is the 5' silyl group which turns on the antiviral activity against WNV and DENV while abrogating the previously reported antiviral potency against human immunodeficiency virus (HIV-1). The antiviral activity was confirmed through a plaque assay where viral titer reduction was observed in the presence of selected compounds. Molecular modeling and competitive S-adenosyl-l-methionine (SAM) binding assay suggest that these compounds likely confer antiviral activity via binding to methyltransferase (MTase). </AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Vernekar</LastName><ForeName>Sanjeev Kumar V</ForeName><Initials>SK</Initials><AffiliationInfo><Affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Qiu</LastName><ForeName>Li</ForeName><Initials>L</Initials><AffiliationInfo><Affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Zhang</LastName><ForeName>Jing</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>‡Wadsworth Center, New York State Department of Health, 120 New Scotland Ave., Albany, New York 12208, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Kankanala</LastName><ForeName>Jayakanth</ForeName><Initials>J</Initials><AffiliationInfo><Affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Li</LastName><ForeName>Hongmin</ForeName><Initials>H</Initials><AffiliationInfo><Affiliation>‡Wadsworth Center, New York State Department of Health, 120 New Scotland Ave., Albany, New York 12208, United States.</Affiliation></AffiliationInfo><AffiliationInfo><Affiliation>§Department of Biomedical Sciences, School of Public Health, University at Albany, Albany, New York 12201, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Geraghty</LastName><ForeName>Robert J</ForeName><Initials>RJ</Initials><AffiliationInfo><Affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Wang</LastName><ForeName>Zhengqiang</ForeName><Initials>Z</Initials><AffiliationInfo><Affiliation>†Center for Drug Design, Academic Health Center, University of Minnesota, Minneapolis, Minnesota 55455, United States.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>R01 AI094335</GrantID><Acronym>AI</Acronym><Agency>NIAID NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>AI094335</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. 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