H2N2V1, Pmc, Checkpoint, bibRecord, 000194

Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their in vitro anti-influenza entry activity††Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.‡‡Electronic supplementary information (ESI) available. See DOI: 10.1039/c7md00245a

Identifieur interne : 000194 ( Pmc/Checkpoint ); précédent : 000193; suivant : 000195

Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their in vitro anti-influenza entry activity††Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.‡‡Electronic supplementary information (ESI) available. See DOI: 10.1039/c7md00245a

Auteurs : Yongying Shi ; Longlong Si ; Xu Han ; Zibo Fan ; Shouxin Wang [République populaire de Chine] ; Man Li ; Jiaqi Sun ; Yongmin Zhang [France] ; Demin Zhou ; Sulong Xiao

Source :

MedChemComm [ 2040-2503 ] ; 2017.

RBID : PMC:6072002

Abstract

The C-4 hydroxyl group of sialic acid is not important for its binding with hemagglutinin and could be replaced with hydrophobic moieties.

Url:

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6072002

DOI: 10.1039/c7md00245a
PubMed: 30108865
PubMed Central: 6072002

Affiliations:

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PMC:6072002

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 anti-influenza entry activity<xref ref-type="fn" rid="fn1">†</xref>
<fn id="fn1"><p>†Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.</p>
</fn>
<xref ref-type="fn" rid="fn2">‡</xref>
<fn id="fn2"><p>‡Electronic supplementary information (ESI) available. See DOI: <uri xlink:type="simple" xlink:href="https://doi.org/10.1039/c7md00245a">10.1039/c7md00245a</uri>
</p>
</fn>
</title>
<author><name sortKey="Shi, Yongying" sort="Shi, Yongying" uniqKey="Shi Y" first="Yongying" last="Shi">Yongying Shi</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Si, Longlong" sort="Si, Longlong" uniqKey="Si L" first="Longlong" last="Si">Longlong Si</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Han, Xu" sort="Han, Xu" uniqKey="Han X" first="Xu" last="Han">Xu Han</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Fan, Zibo" sort="Fan, Zibo" uniqKey="Fan Z" first="Zibo" last="Fan">Zibo Fan</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Wang, Shouxin" sort="Wang, Shouxin" uniqKey="Wang S" first="Shouxin" last="Wang">Shouxin Wang</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="affc"> School of Pharmacy , Jining Medical University , Rizhao 276826 , China</nlm:aff>
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<author><name sortKey="Li, Man" sort="Li, Man" uniqKey="Li M" first="Man" last="Li">Man Li</name>
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<author><name sortKey="Sun, Jiaqi" sort="Sun, Jiaqi" uniqKey="Sun J" first="Jiaqi" last="Sun">Jiaqi Sun</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhang, Yongmin" sort="Zhang, Yongmin" uniqKey="Zhang Y" first="Yongmin" last="Zhang">Yongmin Zhang</name>
<affiliation wicri:level="3"><nlm:aff id="affb"> Institut Parisien de Chimie Moléculaire , CNRS UMR 8232 , Sorbonne Universités , UPMC Univ Paris 06 , 4 place Jussieu , 75005 Paris , France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea> Institut Parisien de Chimie Moléculaire , CNRS UMR 8232 , Sorbonne Universités , UPMC Univ Paris 06 , 4 place Jussieu , 75005 Paris </wicri:regionArea>
<placeName><region type="region" nuts="2">Île-de-France</region>
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</author>
<author><name sortKey="Zhou, Demin" sort="Zhou, Demin" uniqKey="Zhou D" first="Demin" last="Zhou">Demin Zhou</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Xiao, Sulong" sort="Xiao, Sulong" uniqKey="Xiao S" first="Sulong" last="Xiao">Sulong Xiao</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
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<idno type="pmid">30108865</idno>
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<sourceDesc><biblStruct><analytic><title xml:lang="en" level="a" type="main">Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their <italic>in vitro</italic>
 anti-influenza entry activity<xref ref-type="fn" rid="fn1">†</xref>
<fn id="fn1"><p>†Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.</p>
</fn>
<xref ref-type="fn" rid="fn2">‡</xref>
<fn id="fn2"><p>‡Electronic supplementary information (ESI) available. See DOI: <uri xlink:type="simple" xlink:href="https://doi.org/10.1039/c7md00245a">10.1039/c7md00245a</uri>
</p>
</fn>
</title>
<author><name sortKey="Shi, Yongying" sort="Shi, Yongying" uniqKey="Shi Y" first="Yongying" last="Shi">Yongying Shi</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Si, Longlong" sort="Si, Longlong" uniqKey="Si L" first="Longlong" last="Si">Longlong Si</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Han, Xu" sort="Han, Xu" uniqKey="Han X" first="Xu" last="Han">Xu Han</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Fan, Zibo" sort="Fan, Zibo" uniqKey="Fan Z" first="Zibo" last="Fan">Zibo Fan</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Wang, Shouxin" sort="Wang, Shouxin" uniqKey="Wang S" first="Shouxin" last="Wang">Shouxin Wang</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
<affiliation wicri:level="1"><nlm:aff id="affc"> School of Pharmacy , Jining Medical University , Rizhao 276826 , China</nlm:aff>
<country xml:lang="fr">République populaire de Chine</country>
<wicri:regionArea> School of Pharmacy , Jining Medical University , Rizhao 276826 </wicri:regionArea>
<wicri:noRegion>Rizhao 276826 </wicri:noRegion>
</affiliation>
</author>
<author><name sortKey="Li, Man" sort="Li, Man" uniqKey="Li M" first="Man" last="Li">Man Li</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Sun, Jiaqi" sort="Sun, Jiaqi" uniqKey="Sun J" first="Jiaqi" last="Sun">Jiaqi Sun</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Zhang, Yongmin" sort="Zhang, Yongmin" uniqKey="Zhang Y" first="Yongmin" last="Zhang">Yongmin Zhang</name>
<affiliation wicri:level="3"><nlm:aff id="affb"> Institut Parisien de Chimie Moléculaire , CNRS UMR 8232 , Sorbonne Universités , UPMC Univ Paris 06 , 4 place Jussieu , 75005 Paris , France</nlm:aff>
<country xml:lang="fr">France</country>
<wicri:regionArea> Institut Parisien de Chimie Moléculaire , CNRS UMR 8232 , Sorbonne Universités , UPMC Univ Paris 06 , 4 place Jussieu , 75005 Paris </wicri:regionArea>
<placeName><region type="region" nuts="2">Île-de-France</region>
<settlement type="city">Paris </settlement>
</placeName>
</affiliation>
</author>
<author><name sortKey="Zhou, Demin" sort="Zhou, Demin" uniqKey="Zhou D" first="Demin" last="Zhou">Demin Zhou</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
<author><name sortKey="Xiao, Sulong" sort="Xiao, Sulong" uniqKey="Xiao S" first="Sulong" last="Xiao">Sulong Xiao</name>
<affiliation><nlm:aff id="affa"> State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</nlm:aff>
</affiliation>
</author>
</analytic>
<series><title level="j">MedChemComm</title>
<idno type="ISSN">2040-2503</idno>
<idno type="eISSN">2040-2511</idno>
<imprint><date when="2017">2017</date>
</imprint>
</series>
</biblStruct>
</sourceDesc>
</fileDesc>
<profileDesc><textClass></textClass>
</profileDesc>
</teiHeader>
<front><div type="abstract" xml:lang="en"><p><graphic xlink:href="c7md00245a-ga.jpg" id="ga" position="float" orientation="portrait"></graphic>
The C-4 hydroxyl group of sialic acid is not important for its binding with hemagglutinin and could be replaced with hydrophobic moieties.</p>
</div>
</front>
</TEI>
<pmc article-type="research-article"><pmc-comment>The publisher of this article does not allow downloading of the full text in XML form.</pmc-comment>
  <front><journal-meta><journal-id journal-id-type="nlm-ta">Medchemcomm</journal-id>
<journal-id journal-id-type="iso-abbrev">Medchemcomm</journal-id>
<journal-title-group><journal-title>MedChemComm</journal-title>
</journal-title-group>
<issn pub-type="ppub">2040-2503</issn>
<issn pub-type="epub">2040-2511</issn>
<publisher><publisher-name>Royal Society of Chemistry</publisher-name>
</publisher>
</journal-meta>
<article-meta><article-id pub-id-type="pmid">30108865</article-id>
<article-id pub-id-type="pmc">6072002</article-id>
<article-id pub-id-type="publisher-id">c7md00245a</article-id>
<article-id pub-id-type="doi">10.1039/c7md00245a</article-id>
<article-categories><subj-group subj-group-type="heading"><subject>Chemistry</subject>
</subj-group>
</article-categories>
<title-group><article-title>Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their <italic>in vitro</italic>
 anti-influenza entry activity<xref ref-type="fn" rid="fn1">†</xref>
<fn id="fn1"><p>†Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.</p>
</fn>
<xref ref-type="fn" rid="fn2">‡</xref>
<fn id="fn2"><p>‡Electronic supplementary information (ESI) available. See DOI: <uri xlink:type="simple" xlink:href="https://doi.org/10.1039/c7md00245a">10.1039/c7md00245a</uri>
</p>
</fn>
</article-title>
</title-group>
<contrib-group><contrib contrib-type="author"><name><surname>Shi</surname>
<given-names>Yongying</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
<xref ref-type="author-notes" rid="fn3">§</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Si</surname>
<given-names>Longlong</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
<xref ref-type="author-notes" rid="fn3">§</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Han</surname>
<given-names>Xu</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
<xref ref-type="author-notes" rid="fn3">§</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Fan</surname>
<given-names>Zibo</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Wang</surname>
<given-names>Shouxin</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
<xref ref-type="aff" rid="affc">c</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Li</surname>
<given-names>Man</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Sun</surname>
<given-names>Jiaqi</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhang</surname>
<given-names>Yongmin</given-names>
</name>
<xref ref-type="aff" rid="affb">b</xref>
</contrib>
<contrib contrib-type="author"><name><surname>Zhou</surname>
<given-names>Demin</given-names>
</name>
<xref ref-type="aff" rid="affa">a</xref>
</contrib>
<contrib contrib-type="author" corresp="yes"><name><surname>Xiao</surname>
<given-names>Sulong</given-names>
</name>
<contrib-id contrib-id-type="orcid">http://orcid.org/0000-0002-6852-9504</contrib-id>
<xref ref-type="aff" rid="affa">a</xref>
</contrib>
</contrib-group>
<aff id="affa"><label>a</label>
 State Key Laboratory of Natural and Biomimetic Drugs , School of Pharmaceutical Sciences , Peking University , Beijing 100191 , China . Email:<email>slxiao@bjmu.edu.cn</email>
</aff>
<aff id="affb"><label>b</label>
 Institut Parisien de Chimie Moléculaire , CNRS UMR 8232 , Sorbonne Universités , UPMC Univ Paris 06 , 4 place Jussieu , 75005 Paris , France</aff>
<aff id="affc"><label>c</label>
 School of Pharmacy , Jining Medical University , Rizhao 276826 , China</aff>
<author-notes><fn id="fn3"><p>§These authors have contributed equally to this work.</p>
</fn>
</author-notes>
<pub-date pub-type="epub"><day>2</day>
<month>6</month>
<year>2017</year>
</pub-date>
<pub-date pub-type="collection"><day>1</day>
<month>7</month>
<year>2017</year>
</pub-date>
<volume>8</volume>
<issue>7</issue>
<fpage>1531</fpage>
<lpage>1541</lpage>
<history><date date-type="received"><day>11</day>
<month>5</month>
<year>2017</year>
</date>
<date date-type="accepted"><day>30</day>
<month>5</month>
<year>2017</year>
</date>
</history>
<permissions><copyright-statement>This journal is © The Royal Society of Chemistry 2017</copyright-statement>
<copyright-year>2017</copyright-year>
</permissions>
<abstract abstract-type="toc"><p><graphic xlink:href="c7md00245a-ga.jpg" id="ga" position="float" orientation="portrait"></graphic>
The C-4 hydroxyl group of sialic acid is not important for its binding with hemagglutinin and could be replaced with hydrophobic moieties.</p>
</abstract>
<abstract><p>Sialic acid derivatives, analogs, and their conjugates are important pharmacophores. Modification of the C-4 hydroxyl group of sialic acid can lead to derivatives, such as zanamivir, with potent anti-influenza activities. Herein, we described the synthesis of C-4-modified sialic acid derivatives <italic>via</italic>
 conjugation with naturally derived pentacyclic triterpenes, which are active ingredients of traditional Chinese medicine, and the evaluation of their <italic>in vitro</italic>
 anti-influenza virus activity in MDCK cells. Interestingly, a set of configurational isomers was obtained during the de-<italic>O</italic>
-acetylation reaction of two pentacyclic triterpene–sialic acid conjugates under Zemplén conditions, and a mechanism was proposed. Owing to the attachment of the Neu5Ac2en moiety, all synthesized conjugates displayed lower hydrophobicity than their parent compounds. In comparison with ursane- and lupane-type triterpenes, oleanane-type triterpene-functionalized Neu5Ac2en conjugates were most promising. The insertion of a (1,2,3-triazol-4-yl)-methyl between the amide bond and Neu5Ac2en caused a substantial decrease in activity. Compound <bold>15a</bold>
 exhibited the highest inhibitory activity (IC<sub>50</sub>
 = 8.3 μM) and selectivity index (SI = 22.7). Further studies involving hemagglutination inhibition and neuraminidase inhibition suggested that compound <bold>15a</bold>
 inhibited virus-induced hemagglutination with no effect on the enzymatic activity of neuraminidase, indicating that the antiviral activity appeared to be mediated <italic>via</italic>
 interaction with hemagglutinin at the initial stage of viral infection.</p>
</abstract>
</article-meta>
</front>
</pmc>
<affiliations><list><country><li>France</li>
<li>République populaire de Chine</li>
</country>
<region><li>Île-de-France</li>
</region>
<settlement><li>Paris </li>
</settlement>
</list>
<tree><noCountry><name sortKey="Fan, Zibo" sort="Fan, Zibo" uniqKey="Fan Z" first="Zibo" last="Fan">Zibo Fan</name>
<name sortKey="Han, Xu" sort="Han, Xu" uniqKey="Han X" first="Xu" last="Han">Xu Han</name>
<name sortKey="Li, Man" sort="Li, Man" uniqKey="Li M" first="Man" last="Li">Man Li</name>
<name sortKey="Shi, Yongying" sort="Shi, Yongying" uniqKey="Shi Y" first="Yongying" last="Shi">Yongying Shi</name>
<name sortKey="Si, Longlong" sort="Si, Longlong" uniqKey="Si L" first="Longlong" last="Si">Longlong Si</name>
<name sortKey="Sun, Jiaqi" sort="Sun, Jiaqi" uniqKey="Sun J" first="Jiaqi" last="Sun">Jiaqi Sun</name>
<name sortKey="Xiao, Sulong" sort="Xiao, Sulong" uniqKey="Xiao S" first="Sulong" last="Xiao">Sulong Xiao</name>
<name sortKey="Zhou, Demin" sort="Zhou, Demin" uniqKey="Zhou D" first="Demin" last="Zhou">Demin Zhou</name>
</noCountry>
<country name="République populaire de Chine"><noRegion><name sortKey="Wang, Shouxin" sort="Wang, Shouxin" uniqKey="Wang S" first="Shouxin" last="Wang">Shouxin Wang</name>
</noRegion>
</country>
<country name="France"><region name="Île-de-France"><name sortKey="Zhang, Yongmin" sort="Zhang, Yongmin" uniqKey="Zhang Y" first="Yongmin" last="Zhang">Yongmin Zhang</name>
</region>
</country>
</tree>
</affiliations>
</record>

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Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their in vitro anti-influenza entry activity††Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.‡‡Electronic supplementary information (ESI) available. See DOI: 10.1039/c7md00245a

Synthesis of novel pentacyclic triterpene–Neu5Ac2en derivatives and investigation of their in vitro anti-influenza entry activity††Dedicated to Professor Lihe Zhang on the Occasion of His 80th Birthday.‡‡Electronic supplementary information (ESI) available. See DOI: 10.1039/c7md00245a

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