Discovery of Hydrocarbon-Stapled Short α-Helical Peptides as Promising Middle East Respiratory Syndrome Coronavirus (MERS-CoV) Fusion Inhibitors
Identifieur interne : 000A03 ( Main/Exploration ); précédent : 000A02; suivant : 000A04Discovery of Hydrocarbon-Stapled Short α-Helical Peptides as Promising Middle East Respiratory Syndrome Coronavirus (MERS-CoV) Fusion Inhibitors
Auteurs : Chao Wang [République populaire de Chine] ; Shuai Xia [République populaire de Chine] ; Peiyu Zhang [République populaire de Chine] ; Tianhong Zhang [République populaire de Chine] ; Weicong Wang [République populaire de Chine] ; Yangli Tian [République populaire de Chine] ; Guangpeng Meng [République populaire de Chine] ; Shibo Jiang [République populaire de Chine, États-Unis] ; Keliang Liu [République populaire de Chine]Source :
- Journal of Medicinal Chemistry [ 0022-2623 ] ; 2018.
Descripteurs français
- KwdFr :
- Antiviraux (), Antiviraux (pharmacologie), Coronavirus du syndrome respiratoire du Moyen-Orient (), Découverte de médicament, Humains, Hydrocarbures (), Infections à coronavirus (), Peptides (), Peptides (pharmacocinétique), Peptides (pharmacologie), Pénétration virale (), Structure en hélice alpha.
- MESH :
- pharmacocinétique : Peptides.
- pharmacologie : Antiviraux, Peptides.
- Antiviraux, Coronavirus du syndrome respiratoire du Moyen-Orient, Découverte de médicament, Humains, Hydrocarbures, Infections à coronavirus, Peptides, Pénétration virale, Structure en hélice alpha.
English descriptors
- KwdEn :
- Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Coronavirus Infections (prevention & control), Drug Discovery, Humans, Hydrocarbons (chemistry), Middle East Respiratory Syndrome Coronavirus (drug effects), Peptides (chemistry), Peptides (pharmacokinetics), Peptides (pharmacology), Protein Conformation, alpha-Helical, Virus Internalization (drug effects).
- MESH :
- chemical , chemistry : Antiviral Agents, Hydrocarbons, Peptides.
- chemical , pharmacokinetics : Peptides.
- chemical , pharmacology : Antiviral Agents, Peptides.
- drug effects : Middle East Respiratory Syndrome Coronavirus, Virus Internalization.
- prevention & control : Coronavirus Infections.
- Drug Discovery, Humans, Protein Conformation, alpha-Helical.
Abstract
The hexameric α-helical coiled-coil formed between the C-terminal and N-terminal heptad repeat (CHR and NHR) regions of class I viral fusion proteins plays an important role in mediating the fusion of the viral and cellular membranes and provides a clear starting point for molecular mimicry that drives viral fusion inhibitor design. Unfortunately, such peptide mimicry of the short α-helical region in the CHR of Middle East respiratory syndrome coronavirus (MERS-CoV) spike protein has been thwarted by the loss of the peptide’s native α-helical conformation when taken out of the parent protein structure. Here, we describe that appropriate all-hydrocarbon stapling of the short helical portion-based peptide to reinforce its bioactive secondary structure remarkably improves antiviral potency. The resultant stapled peptide P21S10 could effectively inhibit infection by MERS-CoV pseudovirus and its spike protein-mediated cell–cell fusion; additionally, P21S10 exhibits improved pharmacokinetic properties than HR2P-M2, suggesting strong potential for development as an anti-MERS-CoV therapeutic.
Url:
DOI: 10.1021/acs.jmedchem.7b01732
PubMed: 29442512
PubMed Central: 7075646
Affiliations:
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Le document en format XML
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Kimball Research Institute,<institution>New York Blood Center</institution>, New York, New York 10065,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Liu, Keliang" sort="Liu, Keliang" uniqKey="Liu K" first="Keliang" last="Liu">Keliang Liu</name><affiliation wicri:level="1"><nlm:aff id="aff1">State Key Laboratory of Toxicology and Medical Countermeasures,<institution>Beijing Institute of Pharmacology and Toxicology</institution>, 27 Tai-Ping Road, Beijing 100850,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Key Laboratory of Structure-Based Drug Design and Discovery of the Ministry of Education,<institution>Shenyang Pharmaceutical University</institution>, Shenyang 110016,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></titleStmt><publicationStmt><idno type="wicri:source">PMC</idno><idno type="pmid">29442512</idno><idno type="pmc">7075646</idno><idno type="url">http://www.ncbi.nlm.nih.gov/pmc/articles/PMC7075646</idno><idno type="RBID">PMC:7075646</idno><idno type="doi">10.1021/acs.jmedchem.7b01732</idno><date when="2018">2018</date><idno type="wicri:Area/Pmc/Corpus">000130</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Corpus" wicri:corpus="PMC">000130</idno><idno type="wicri:Area/Pmc/Curation">000130</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Curation">000130</idno><idno type="wicri:Area/Pmc/Checkpoint">000599</idno><idno type="wicri:explorRef" wicri:stream="Pmc" wicri:step="Checkpoint">000599</idno><idno type="wicri:source">PubMed</idno><idno type="RBID">pubmed:29442512</idno><idno type="wicri:Area/PubMed/Corpus">000997</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Corpus" wicri:corpus="PubMed">000997</idno><idno type="wicri:Area/PubMed/Curation">000997</idno><idno type="wicri:explorRef" wicri:stream="PubMed" wicri:step="Curation">000997</idno><idno type="wicri:Area/PubMed/Checkpoint">000948</idno><idno type="wicri:explorRef" wicri:stream="Checkpoint" wicri:step="PubMed">000948</idno><idno type="wicri:Area/Ncbi/Merge">001D34</idno><idno type="wicri:Area/Ncbi/Curation">001D34</idno><idno type="wicri:Area/Ncbi/Checkpoint">001D34</idno><idno type="wicri:doubleKey">0022-2623:2018:Wang C:discovery:of:hydrocarbon</idno><idno type="wicri:Area/Main/Merge">000A06</idno><idno type="wicri:Area/Main/Curation">000A03</idno><idno type="wicri:Area/Main/Exploration">000A03</idno></publicationStmt><sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Discovery of Hydrocarbon-Stapled
Short α-Helical
Peptides as Promising Middle East Respiratory Syndrome Coronavirus
(MERS-CoV) Fusion Inhibitors</title><author><name sortKey="Wang, Chao" sort="Wang, Chao" uniqKey="Wang C" first="Chao" last="Wang">Chao Wang</name><affiliation wicri:level="1"><nlm:aff id="aff1">State Key Laboratory of Toxicology and Medical Countermeasures,<institution>Beijing Institute of Pharmacology and Toxicology</institution>, 27 Tai-Ping Road, Beijing 100850,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Xia, Shuai" sort="Xia, Shuai" uniqKey="Xia S" first="Shuai" last="Xia">Shuai Xia</name><affiliation wicri:level="1"><nlm:aff id="aff2">Key Laboratory of Medical Molecular Virology of MOE/MOH, School of Basic Medical Sciences and Shanghai Public Health Clinical Center,<institution>Fudan University</institution>, 130 Dong An Road, Shanghai 200032,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Zhang, Peiyu" sort="Zhang, Peiyu" uniqKey="Zhang P" first="Peiyu" last="Zhang">Peiyu Zhang</name><affiliation wicri:level="1"><nlm:aff id="aff3">Key Laboratory of Structure-Based Drug Design and Discovery of the Ministry of Education,<institution>Shenyang Pharmaceutical University</institution>, Shenyang 110016,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Zhang, Tianhong" sort="Zhang, Tianhong" uniqKey="Zhang T" first="Tianhong" last="Zhang">Tianhong Zhang</name><affiliation wicri:level="1"><nlm:aff id="aff1">State Key Laboratory of Toxicology and Medical Countermeasures,<institution>Beijing Institute of Pharmacology and Toxicology</institution>, 27 Tai-Ping Road, Beijing 100850,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Wang, Weicong" sort="Wang, Weicong" uniqKey="Wang W" first="Weicong" last="Wang">Weicong Wang</name><affiliation wicri:level="1"><nlm:aff id="aff5">Pharmaceutical Preparation Section, Plastic Surgery Hospital,<institution>Chinese Academy of Medical Sciences and Peking Union Medical College</institution>, Beijing 100144,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Tian, Yangli" sort="Tian, Yangli" uniqKey="Tian Y" first="Yangli" last="Tian">Yangli Tian</name><affiliation wicri:level="1"><nlm:aff id="aff1">State Key Laboratory of Toxicology and Medical Countermeasures,<institution>Beijing Institute of Pharmacology and Toxicology</institution>, 27 Tai-Ping Road, Beijing 100850,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Meng, Guangpeng" sort="Meng, Guangpeng" uniqKey="Meng G" first="Guangpeng" last="Meng">Guangpeng Meng</name><affiliation wicri:level="1"><nlm:aff id="aff3">Key Laboratory of Structure-Based Drug Design and Discovery of the Ministry of Education,<institution>Shenyang Pharmaceutical University</institution>, Shenyang 110016,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Jiang, Shibo" sort="Jiang, Shibo" uniqKey="Jiang S" first="Shibo" last="Jiang">Shibo Jiang</name><affiliation wicri:level="1"><nlm:aff id="aff2">Key Laboratory of Medical Molecular Virology of MOE/MOH, School of Basic Medical Sciences and Shanghai Public Health Clinical Center,<institution>Fudan University</institution>, 130 Dong An Road, Shanghai 200032,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff4">Lindsley F. Kimball Research Institute,<institution>New York Blood Center</institution>, New York, New York 10065,<country>United States</country></nlm:aff><country xml:lang="fr">États-Unis</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author><author><name sortKey="Liu, Keliang" sort="Liu, Keliang" uniqKey="Liu K" first="Keliang" last="Liu">Keliang Liu</name><affiliation wicri:level="1"><nlm:aff id="aff1">State Key Laboratory of Toxicology and Medical Countermeasures,<institution>Beijing Institute of Pharmacology and Toxicology</institution>, 27 Tai-Ping Road, Beijing 100850,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="aff3">Key Laboratory of Structure-Based Drug Design and Discovery of the Ministry of Education,<institution>Shenyang Pharmaceutical University</institution>, Shenyang 110016,<country>China</country></nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea># see nlm:aff country strict</wicri:regionArea></affiliation></author></analytic><series><title level="j">Journal of Medicinal Chemistry</title><idno type="ISSN">0022-2623</idno><idno type="eISSN">1520-4804</idno><imprint><date when="2018">2018</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>Coronavirus Infections (prevention & control)</term><term>Drug Discovery</term><term>Humans</term><term>Hydrocarbons (chemistry)</term><term>Middle East Respiratory Syndrome Coronavirus (drug effects)</term><term>Peptides (chemistry)</term><term>Peptides (pharmacokinetics)</term><term>Peptides (pharmacology)</term><term>Protein Conformation, alpha-Helical</term><term>Virus Internalization (drug effects)</term></keywords><keywords scheme="KwdFr" xml:lang="fr"><term>Antiviraux ()</term><term>Antiviraux (pharmacologie)</term><term>Coronavirus du syndrome respiratoire du Moyen-Orient ()</term><term>Découverte de médicament</term><term>Humains</term><term>Hydrocarbures ()</term><term>Infections à coronavirus ()</term><term>Peptides ()</term><term>Peptides (pharmacocinétique)</term><term>Peptides (pharmacologie)</term><term>Pénétration virale ()</term><term>Structure en hélice alpha</term></keywords><keywords scheme="MESH" type="chemical" qualifier="chemistry" xml:lang="en"><term>Antiviral Agents</term><term>Hydrocarbons</term><term>Peptides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacokinetics" xml:lang="en"><term>Peptides</term></keywords><keywords scheme="MESH" type="chemical" qualifier="pharmacology" xml:lang="en"><term>Antiviral Agents</term><term>Peptides</term></keywords><keywords scheme="MESH" qualifier="drug effects" xml:lang="en"><term>Middle East Respiratory Syndrome Coronavirus</term><term>Virus Internalization</term></keywords><keywords scheme="MESH" qualifier="pharmacocinétique" xml:lang="fr"><term>Peptides</term></keywords><keywords scheme="MESH" qualifier="pharmacologie" xml:lang="fr"><term>Antiviraux</term><term>Peptides</term></keywords><keywords scheme="MESH" qualifier="prevention & control" xml:lang="en"><term>Coronavirus Infections</term></keywords><keywords scheme="MESH" xml:lang="en"><term>Drug Discovery</term><term>Humans</term><term>Protein Conformation, alpha-Helical</term></keywords><keywords scheme="MESH" xml:lang="fr"><term>Antiviraux</term><term>Coronavirus du syndrome respiratoire du Moyen-Orient</term><term>Découverte de médicament</term><term>Humains</term><term>Hydrocarbures</term><term>Infections à coronavirus</term><term>Peptides</term><term>Pénétration virale</term><term>Structure en hélice alpha</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en"><p content-type="toc-graphic"><graphic xlink:href="jm7b01732_0006" id="ab-tgr1"></graphic></p><p>The hexameric α-helical coiled-coil
formed between the C-terminal
and N-terminal heptad repeat (CHR and NHR) regions of class I viral
fusion proteins plays an important role in mediating the fusion of
the viral and cellular membranes and provides a clear starting point
for molecular mimicry that drives viral fusion inhibitor design. Unfortunately,
such peptide mimicry of the short α-helical region in the CHR
of Middle East respiratory syndrome coronavirus (MERS-CoV) spike protein
has been thwarted by the loss of the peptide’s native α-helical
conformation when taken out of the parent protein structure. Here,
we describe that appropriate all-hydrocarbon stapling of the short
helical portion-based peptide to reinforce its bioactive secondary
structure remarkably improves antiviral potency. The resultant stapled
peptide P21S10 could effectively inhibit infection by MERS-CoV pseudovirus
and its spike protein-mediated cell–cell fusion; additionally,
P21S10 exhibits improved pharmacokinetic properties than HR2P-M2,
suggesting strong potential for development as an anti-MERS-CoV therapeutic.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct><analytic><author><name sortKey="Harrison, S C" uniqKey="Harrison S">S. C. Harrison</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Dimitrov, D S" uniqKey="Dimitrov D">D. S. Dimitrov</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Eckert, D M" uniqKey="Eckert D">D. M. Eckert</name></author><author><name sortKey="Kim, P S" uniqKey="Kim P">P. S. Kim</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Vigant, F" uniqKey="Vigant F">F. Vigant</name></author><author><name sortKey="Santos, N C" uniqKey="Santos N">N. C. Santos</name></author><author><name sortKey="Lee, B" uniqKey="Lee B">B. Lee</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Lu, M" uniqKey="Lu M">M. 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Zhou</name></author></analytic></biblStruct></listBibl></div1></back></TEI><affiliations><list><country><li>République populaire de Chine</li><li>États-Unis</li></country></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Wang, Chao" sort="Wang, Chao" uniqKey="Wang C" first="Chao" last="Wang">Chao Wang</name></noRegion><name sortKey="Jiang, Shibo" sort="Jiang, Shibo" uniqKey="Jiang S" first="Shibo" last="Jiang">Shibo Jiang</name><name sortKey="Liu, Keliang" sort="Liu, Keliang" uniqKey="Liu K" first="Keliang" last="Liu">Keliang Liu</name><name sortKey="Liu, Keliang" sort="Liu, Keliang" uniqKey="Liu K" first="Keliang" last="Liu">Keliang Liu</name><name sortKey="Meng, Guangpeng" sort="Meng, Guangpeng" uniqKey="Meng G" first="Guangpeng" last="Meng">Guangpeng Meng</name><name sortKey="Tian, Yangli" sort="Tian, Yangli" uniqKey="Tian Y" first="Yangli" last="Tian">Yangli Tian</name><name sortKey="Wang, Weicong" sort="Wang, Weicong" uniqKey="Wang W" first="Weicong" last="Wang">Weicong Wang</name><name sortKey="Xia, Shuai" sort="Xia, Shuai" uniqKey="Xia S" first="Shuai" last="Xia">Shuai Xia</name><name sortKey="Zhang, Peiyu" sort="Zhang, Peiyu" uniqKey="Zhang P" first="Peiyu" last="Zhang">Peiyu Zhang</name><name sortKey="Zhang, Tianhong" sort="Zhang, Tianhong" uniqKey="Zhang T" first="Tianhong" last="Zhang">Tianhong Zhang</name></country><country name="États-Unis"><noRegion><name sortKey="Jiang, Shibo" sort="Jiang, Shibo" uniqKey="Jiang S" first="Shibo" last="Jiang">Shibo Jiang</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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