Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.
Identifieur interne : 000418 ( PubMed/Checkpoint ); précédent : 000417; suivant : 000419Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.
Auteurs : Mary K. Yates [États-Unis] ; Payel Chatterjee [États-Unis] ; Mike Flint [États-Unis] ; Yafet Arefeayne [États-Unis] ; Damjan Makuc [Slovénie] ; Janez Plavec [Slovénie] ; Christina F. Spiropoulou [États-Unis] ; Katherine L. Seley-Radtke [États-Unis]Source :
- Molecules (Basel, Switzerland) [ 1420-3049 ] ; 2019.
Descripteurs français
- KwdFr :
- MESH :
English descriptors
- KwdEn :
- Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Cell Line, Tumor, Ebolavirus (drug effects), Humans, Indicators and Reagents, Lipids (chemistry), Molecular Conformation, Proton Magnetic Resonance Spectroscopy, Pyrimidines (chemistry), Pyrimidines (pharmacology), Structure-Activity Relationship.
- MESH :
- chemical , chemistry : Antiviral Agents, Lipids, Pyrimidines.
- chemical , pharmacology : Antiviral Agents, Pyrimidines.
- drug effects : Ebolavirus.
- Cell Line, Tumor, Humans, Indicators and Reagents, Molecular Conformation, Proton Magnetic Resonance Spectroscopy, Structure-Activity Relationship.
Abstract
Due to their ability to inhibit viral DNA or RNA replication, nucleoside analogues have been used for decades as potent antiviral therapeutics. However, one of the major limitations of nucleoside analogues is the development of antiviral resistance. In that regard, flexible nucleoside analogues known as "fleximers" have garnered attention over the years due to their ability to survey different amino acids in enzyme binding sites, thus overcoming the potential development of antiviral resistance. Acyclic fleximers have previously demonstrated antiviral activity against numerous viruses including Middle East Respiratory Syndrome coronavirus (MERS-CoV), Ebola virus (EBOV), and, most recently, flaviviruses such as Dengue (DENV) and Yellow Fever Virus (YFV). Due to these interesting results, a Structure Activity Relationship (SAR) study was pursued in order to analyze the effect of the pyrimidine functional group and acyl protecting group on antiviral activity, cytotoxicity, and conformation. The results of those studies are presented herein.
DOI: 10.3390/molecules24173184
PubMed: 31480658
Affiliations:
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Yates</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250</wicri:regionArea><placeName><region type="state">Maryland</region><settlement type="city">College Park (Maryland)</settlement></placeName><orgName type="university">Université du Maryland</orgName></affiliation></author><author><name sortKey="Chatterjee, Payel" sort="Chatterjee, Payel" uniqKey="Chatterjee P" first="Payel" last="Chatterjee">Payel Chatterjee</name><affiliation wicri:level="2"><nlm:affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329</wicri:regionArea><placeName><region type="state">Géorgie (États-Unis)</region></placeName></affiliation></author><author><name sortKey="Flint, Mike" sort="Flint, Mike" uniqKey="Flint M" first="Mike" last="Flint">Mike Flint</name><affiliation wicri:level="2"><nlm:affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329</wicri:regionArea><placeName><region type="state">Géorgie (États-Unis)</region></placeName></affiliation></author><author><name sortKey="Arefeayne, Yafet" sort="Arefeayne, Yafet" uniqKey="Arefeayne Y" first="Yafet" last="Arefeayne">Yafet Arefeayne</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250</wicri:regionArea><placeName><region type="state">Maryland</region><settlement type="city">College Park (Maryland)</settlement></placeName><orgName type="university">Université du Maryland</orgName></affiliation></author><author><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name><affiliation wicri:level="1"><nlm:affiliation>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.</nlm:affiliation><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana</wicri:regionArea><wicri:noRegion>SI-1000 Ljubljana</wicri:noRegion></affiliation></author><author><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name><affiliation wicri:level="1"><nlm:affiliation>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.</nlm:affiliation><country xml:lang="fr">Slovénie</country><wicri:regionArea>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana</wicri:regionArea><wicri:noRegion>SI-1000 Ljubljana</wicri:noRegion></affiliation></author><author><name sortKey="Spiropoulou, Christina F" sort="Spiropoulou, Christina F" uniqKey="Spiropoulou C" first="Christina F" last="Spiropoulou">Christina F. Spiropoulou</name><affiliation wicri:level="2"><nlm:affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329</wicri:regionArea><placeName><region type="state">Géorgie (États-Unis)</region></placeName></affiliation></author><author><name sortKey="Seley Radtke, Katherine L" sort="Seley Radtke, Katherine L" uniqKey="Seley Radtke K" first="Katherine L" last="Seley-Radtke">Katherine L. Seley-Radtke</name><affiliation wicri:level="4"><nlm:affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA. kseley@umbc.edu.</nlm:affiliation><country xml:lang="fr">États-Unis</country><wicri:regionArea>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250</wicri:regionArea><placeName><region type="state">Maryland</region><settlement type="city">College Park (Maryland)</settlement></placeName><orgName type="university">Université du Maryland</orgName></affiliation></author></analytic><series><title level="j">Molecules (Basel, Switzerland)</title><idno type="eISSN">1420-3049</idno><imprint><date when="2019" type="published">2019</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>Cell Line, Tumor</term><term>Ebolavirus (drug effects)</term><term>Humans</term><term>Indicators and Reagents</term><term>Lipids (chemistry)</term><term>Molecular Conformation</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Pyrimidines (chemistry)</term><term>Pyrimidines (pharmacology)</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Conformation moléculaire</term><term>Ebolavirus ()</term><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire tumorale</term><term>Lipides ()</term><term>Pyrimidines ()</term><term>Pyrimidines (pharmacologie)</term><term>Relation structure-activité</term><term>Spectroscopie par résonance magnétique du proton</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Lipids</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Ebolavirus</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Pyrimidines</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Cell Line, Tumor</term><term>Humans</term><term>Indicators and Reagents</term><term>Molecular Conformation</term><term>Proton Magnetic Resonance Spectroscopy</term><term>Structure-Activity Relationship</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Conformation moléculaire</term><term>Ebolavirus</term><term>Humains</term><term>Indicateurs et réactifs</term><term>Lignée cellulaire tumorale</term><term>Lipides</term><term>Pyrimidines</term><term>Relation structure-activité</term><term>Spectroscopie par résonance magnétique du proton</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Due to their ability to inhibit viral DNA or RNA replication, nucleoside analogues have been used for decades as potent antiviral therapeutics. However, one of the major limitations of nucleoside analogues is the development of antiviral resistance. In that regard, flexible nucleoside analogues known as "fleximers" have garnered attention over the years due to their ability to survey different amino acids in enzyme binding sites, thus overcoming the potential development of antiviral resistance. Acyclic fleximers have previously demonstrated antiviral activity against numerous viruses including Middle East Respiratory Syndrome coronavirus (MERS-CoV), Ebola virus (EBOV), and, most recently, flaviviruses such as Dengue (DENV) and Yellow Fever Virus (YFV). Due to these interesting results, a Structure Activity Relationship (SAR) study was pursued in order to analyze the effect of the pyrimidine functional group and acyl protecting group on antiviral activity, cytotoxicity, and conformation. The results of those studies are presented herein.</div></front></TEI><pubmed><MedlineCitation Status="MEDLINE" Owner="NLM"><PMID Version="1">31480658</PMID><DateCompleted><Year>2020</Year><Month>01</Month><Day>30</Day></DateCompleted><DateRevised><Year>2020</Year><Month>02</Month><Day>25</Day></DateRevised><Article PubModel="Electronic"><Journal><ISSN IssnType="Electronic">1420-3049</ISSN><JournalIssue CitedMedium="Internet"><Volume>24</Volume><Issue>17</Issue><PubDate><Year>2019</Year><Month>Sep</Month><Day>02</Day></PubDate></JournalIssue><Title>Molecules (Basel, Switzerland)</Title><ISOAbbreviation>Molecules</ISOAbbreviation></Journal><ArticleTitle>Probing the Effects of Pyrimidine Functional Group Switches on Acyclic Fleximer Analogues for Antiviral Activity.</ArticleTitle><ELocationID EIdType="pii" ValidYN="Y">E3184</ELocationID><ELocationID EIdType="doi" ValidYN="Y">10.3390/molecules24173184</ELocationID><Abstract><AbstractText>Due to their ability to inhibit viral DNA or RNA replication, nucleoside analogues have been used for decades as potent antiviral therapeutics. However, one of the major limitations of nucleoside analogues is the development of antiviral resistance. In that regard, flexible nucleoside analogues known as "fleximers" have garnered attention over the years due to their ability to survey different amino acids in enzyme binding sites, thus overcoming the potential development of antiviral resistance. Acyclic fleximers have previously demonstrated antiviral activity against numerous viruses including Middle East Respiratory Syndrome coronavirus (MERS-CoV), Ebola virus (EBOV), and, most recently, flaviviruses such as Dengue (DENV) and Yellow Fever Virus (YFV). Due to these interesting results, a Structure Activity Relationship (SAR) study was pursued in order to analyze the effect of the pyrimidine functional group and acyl protecting group on antiviral activity, cytotoxicity, and conformation. The results of those studies are presented herein.</AbstractText></Abstract><AuthorList CompleteYN="Y"><Author ValidYN="Y"><LastName>Yates</LastName><ForeName>Mary K</ForeName><Initials>MK</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Chatterjee</LastName><ForeName>Payel</ForeName><Initials>P</Initials><AffiliationInfo><Affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Flint</LastName><ForeName>Mike</ForeName><Initials>M</Initials><Identifier Source="ORCID">0000-0002-5373-787X</Identifier><AffiliationInfo><Affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Arefeayne</LastName><ForeName>Yafet</ForeName><Initials>Y</Initials><AffiliationInfo><Affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Makuc</LastName><ForeName>Damjan</ForeName><Initials>D</Initials><AffiliationInfo><Affiliation>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Plavec</LastName><ForeName>Janez</ForeName><Initials>J</Initials><Identifier Source="ORCID">0000-0003-1570-8602</Identifier><AffiliationInfo><Affiliation>Slovenian NMR Center, National Institute of Chemistry, Hajdrihova 19, SI-1000 Ljubljana, Slovenia.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Spiropoulou</LastName><ForeName>Christina F</ForeName><Initials>CF</Initials><AffiliationInfo><Affiliation>Viral Special Pathogens Branch, Centers for Disease Control and Prevention, Atlanta, GA 30329, USA.</Affiliation></AffiliationInfo></Author><Author ValidYN="Y"><LastName>Seley-Radtke</LastName><ForeName>Katherine L</ForeName><Initials>KL</Initials><Identifier Source="ORCID">0000-0002-0154-3459</Identifier><AffiliationInfo><Affiliation>Department of Chemistry and Biochemistry, University of Maryland, Baltimore County, Baltimore, MD 21250, USA. kseley@umbc.edu.</Affiliation></AffiliationInfo></Author></AuthorList><Language>eng</Language><GrantList CompleteYN="Y"><Grant><GrantID>T32 GM066706</GrantID><Acronym>NH</Acronym><Agency>NIH HHS</Agency><Country>United States</Country></Grant><Grant><GrantID>AI135252</GrantID><Acronym>NH</Acronym><Agency>NIH HHS</Agency><Country>United States</Country></Grant></GrantList><PublicationTypeList><PublicationType UI="D016428">Journal Article</PublicationType></PublicationTypeList><ArticleDate DateType="Electronic"><Year>2019</Year><Month>09</Month><Day>02</Day></ArticleDate></Article><MedlineJournalInfo><Country>Switzerland</Country><MedlineTA>Molecules</MedlineTA><NlmUniqueID>100964009</NlmUniqueID><ISSNLinking>1420-3049</ISSNLinking></MedlineJournalInfo><ChemicalList><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D000998">Antiviral Agents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D007202">Indicators and Reagents</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D008055">Lipids</NameOfSubstance></Chemical><Chemical><RegistryNumber>0</RegistryNumber><NameOfSubstance UI="D011743">Pyrimidines</NameOfSubstance></Chemical><Chemical><RegistryNumber>K8CXK5Q32L</RegistryNumber><NameOfSubstance UI="C030986">pyrimidine</NameOfSubstance></Chemical></ChemicalList><CitationSubset>IM</CitationSubset><MeshHeadingList><MeshHeading><DescriptorName UI="D000998" MajorTopicYN="N">Antiviral Agents</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D045744" MajorTopicYN="N">Cell Line, Tumor</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D029043" MajorTopicYN="N">Ebolavirus</DescriptorName><QualifierName UI="Q000187" MajorTopicYN="N">drug effects</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D006801" MajorTopicYN="N">Humans</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D007202" MajorTopicYN="N">Indicators and Reagents</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D008055" MajorTopicYN="N">Lipids</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="N">chemistry</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D008968" MajorTopicYN="N">Molecular Conformation</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D066244" MajorTopicYN="N">Proton Magnetic Resonance Spectroscopy</DescriptorName></MeshHeading><MeshHeading><DescriptorName UI="D011743" MajorTopicYN="N">Pyrimidines</DescriptorName><QualifierName UI="Q000737" MajorTopicYN="Y">chemistry</QualifierName><QualifierName UI="Q000494" MajorTopicYN="Y">pharmacology</QualifierName></MeshHeading><MeshHeading><DescriptorName UI="D013329" MajorTopicYN="N">Structure-Activity Relationship</DescriptorName></MeshHeading></MeshHeadingList><KeywordList Owner="NOTNLM"><Keyword MajorTopicYN="N">SAR</Keyword><Keyword MajorTopicYN="N">filovirus</Keyword><Keyword MajorTopicYN="N">flavivirus</Keyword><Keyword MajorTopicYN="N">fleximers</Keyword><Keyword MajorTopicYN="N">nucleoside</Keyword></KeywordList></MedlineCitation><PubmedData><History><PubMedPubDate PubStatus="received"><Year>2019</Year><Month>08</Month><Day>02</Day></PubMedPubDate><PubMedPubDate 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(États-Unis)</li><li>Maryland</li></region><settlement><li>College Park (Maryland)</li></settlement><orgName><li>Université du Maryland</li></orgName></list><tree><country name="États-Unis"><region name="Maryland"><name sortKey="Yates, Mary K" sort="Yates, Mary K" uniqKey="Yates M" first="Mary K" last="Yates">Mary K. Yates</name></region><name sortKey="Arefeayne, Yafet" sort="Arefeayne, Yafet" uniqKey="Arefeayne Y" first="Yafet" last="Arefeayne">Yafet Arefeayne</name><name sortKey="Chatterjee, Payel" sort="Chatterjee, Payel" uniqKey="Chatterjee P" first="Payel" last="Chatterjee">Payel Chatterjee</name><name sortKey="Flint, Mike" sort="Flint, Mike" uniqKey="Flint M" first="Mike" last="Flint">Mike Flint</name><name sortKey="Seley Radtke, Katherine L" sort="Seley Radtke, Katherine L" uniqKey="Seley Radtke K" first="Katherine L" last="Seley-Radtke">Katherine L. Seley-Radtke</name><name sortKey="Spiropoulou, Christina F" sort="Spiropoulou, Christina F" uniqKey="Spiropoulou C" first="Christina F" last="Spiropoulou">Christina F. Spiropoulou</name></country><country name="Slovénie"><noRegion><name sortKey="Makuc, Damjan" sort="Makuc, Damjan" uniqKey="Makuc D" first="Damjan" last="Makuc">Damjan Makuc</name></noRegion><name sortKey="Plavec, Janez" sort="Plavec, Janez" uniqKey="Plavec J" first="Janez" last="Plavec">Janez Plavec</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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