Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality
Identifieur interne : 000E05 ( Ncbi/Merge ); précédent : 000E04; suivant : 000E06Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality
Auteurs : Christopher J. Vavricka [Japon] ; Chiaki Muto [Japon] ; Tomohisa Hasunuma [Japon] ; Yoshinobu Kimura [Japon] ; Michihiro Araki [Japon] ; Yan Wu [République populaire de Chine] ; George F. Gao [République populaire de Chine] ; Hiroshi Ohrui [Japon] ; Minoru Izumi [Japon] ; Hiromasa Kiyota [Japon]Source :
- Scientific Reports [ 2045-2322 ] ; 2017.
Abstract
The design, synthesis and application of
Url:
DOI: 10.1038/s41598-017-07836-y
PubMed: 28811524
PubMed Central: 5557986
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Vavricka</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Okayama</wicri:regionArea></affiliation><affiliation wicri:level="1"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1092 3077</institution-id><institution-id institution-id-type="GRID">grid.31432.37</institution-id><institution>Graduate School of Science, Technology and Innovation,</institution><institution>Kobe University,</institution></institution-wrap>Kobe, 657-0013 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Kobe</wicri:regionArea></affiliation></author><author><name sortKey="Muto, Chiaki" sort="Muto, Chiaki" uniqKey="Muto C" first="Chiaki" last="Muto">Chiaki Muto</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Okayama</wicri:regionArea></affiliation></author><author><name sortKey="Hasunuma, Tomohisa" sort="Hasunuma, Tomohisa" uniqKey="Hasunuma T" first="Tomohisa" last="Hasunuma">Tomohisa Hasunuma</name><affiliation wicri:level="1"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1092 3077</institution-id><institution-id institution-id-type="GRID">grid.31432.37</institution-id><institution>Graduate School of Science, Technology and Innovation,</institution><institution>Kobe University,</institution></institution-wrap>Kobe, 657-0013 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Kobe</wicri:regionArea></affiliation></author><author><name sortKey="Kimura, Yoshinobu" sort="Kimura, Yoshinobu" uniqKey="Kimura Y" first="Yoshinobu" last="Kimura">Yoshinobu Kimura</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Okayama</wicri:regionArea></affiliation></author><author><name sortKey="Araki, Michihiro" sort="Araki, Michihiro" uniqKey="Araki M" first="Michihiro" last="Araki">Michihiro Araki</name><affiliation wicri:level="1"><nlm:aff id="Aff2"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1092 3077</institution-id><institution-id institution-id-type="GRID">grid.31432.37</institution-id><institution>Graduate School of Science, Technology and Innovation,</institution><institution>Kobe University,</institution></institution-wrap>Kobe, 657-0013 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Kobe</wicri:regionArea></affiliation></author><author><name sortKey="Wu, Yan" sort="Wu, Yan" uniqKey="Wu Y" first="Yan" last="Wu">Yan Wu</name><affiliation wicri:level="1"><nlm:aff id="Aff3"><institution-wrap><institution-id institution-id-type="ISNI">0000000119573309</institution-id><institution-id institution-id-type="GRID">grid.9227.e</institution-id><institution>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology,</institution><institution>Chinese Academy of Sciences,</institution></institution-wrap>Beijing, 100101 China</nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Beijing</wicri:regionArea></affiliation></author><author><name sortKey="Gao, George F" sort="Gao, George F" uniqKey="Gao G" first="George F." last="Gao">George F. Gao</name><affiliation wicri:level="1"><nlm:aff id="Aff3"><institution-wrap><institution-id institution-id-type="ISNI">0000000119573309</institution-id><institution-id institution-id-type="GRID">grid.9227.e</institution-id><institution>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology,</institution><institution>Chinese Academy of Sciences,</institution></institution-wrap>Beijing, 100101 China</nlm:aff><country xml:lang="fr">République populaire de Chine</country><wicri:regionArea>Beijing</wicri:regionArea></affiliation></author><author><name sortKey="Ohrui, Hiroshi" sort="Ohrui, Hiroshi" uniqKey="Ohrui H" first="Hiroshi" last="Ohrui">Hiroshi Ohrui</name><affiliation wicri:level="1"><nlm:aff id="Aff4"><institution-wrap><institution-id institution-id-type="GRID">grid.443246.3</institution-id><institution></institution><institution>Yokohama College of Pharmacy,</institution></institution-wrap>Yokohama, 245-0066 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Yokohama</wicri:regionArea></affiliation></author><author><name sortKey="Izumi, Minoru" sort="Izumi, Minoru" uniqKey="Izumi M" first="Minoru" last="Izumi">Minoru Izumi</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Okayama</wicri:regionArea></affiliation></author><author><name sortKey="Kiyota, Hiromasa" sort="Kiyota, Hiromasa" uniqKey="Kiyota H" first="Hiromasa" last="Kiyota">Hiromasa Kiyota</name><affiliation wicri:level="1"><nlm:aff id="Aff1"><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</nlm:aff><country xml:lang="fr">Japon</country><wicri:regionArea>Okayama</wicri:regionArea></affiliation></author></analytic><series><title level="j">Scientific Reports</title><idno type="eISSN">2045-2322</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 id="Par1">The design, synthesis and application of <italic>N</italic>-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-<italic>N</italic>-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.</p></div></front><back><div1 type="bibliography"><listBibl><biblStruct></biblStruct><biblStruct><analytic><author><name sortKey="Kim, Cu" uniqKey="Kim C">CU Kim</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Vavricka, Cj" uniqKey="Vavricka C">CJ Vavricka</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Wallimann, K" uniqKey="Wallimann K">K Wallimann</name></author><author><name sortKey="Vasella, A" uniqKey="Vasella A">A Vasella</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Shie, J J" uniqKey="Shie J">J-J Shie</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="White, Cl" uniqKey="White C">CL White</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Streicher, H" uniqKey="Streicher H">H Streicher</name></author><author><name sortKey="Busse, H" uniqKey="Busse H">H Busse</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Streicher, H" uniqKey="Streicher H">H Streicher</name></author><author><name sortKey="Meisch, J" uniqKey="Meisch J">J Meisch</name></author><author><name sortKey="Bohner, C" uniqKey="Bohner C">C Bohner</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Gao, J" uniqKey="Gao J">J Gao</name></author><author><name sortKey="Martichonok, V" uniqKey="Martichonok V">V Martichonok</name></author><author><name sortKey="Whitesides, Gm" uniqKey="Whitesides G">GM Whitesides</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Chan, T H" uniqKey="Chan T">T-H Chan</name></author><author><name sortKey="Xin, Y C" uniqKey="Xin Y">Y-C Xin</name></author><author><name sortKey="Von Itzstein, M" uniqKey="Von Itzstein M">M von 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sortKey="Hurt, Ac" uniqKey="Hurt A">AC Hurt</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Yan, W" uniqKey="Yan W">W Yan</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Collins, Pj" uniqKey="Collins P">PJ Collins</name></author></analytic></biblStruct><biblStruct><analytic><author><name sortKey="Meindl, P" uniqKey="Meindl P">P Meindl</name></author><author><name sortKey="Bodo, G" uniqKey="Bodo G">G Bodo</name></author><author><name sortKey="Palese, P" uniqKey="Palese P">P Palese</name></author><author><name sortKey="Schulman, J" uniqKey="Schulman J">J Schulman</name></author><author><name sortKey="Tuppy, H" uniqKey="Tuppy H">H Tuppy</name></author></analytic></biblStruct></listBibl></div1></back></TEI><pmc article-type="research-article"><pmc-dir>properties open_access</pmc-dir>
<front><journal-meta><journal-id journal-id-type="nlm-ta">Sci Rep</journal-id><journal-id journal-id-type="iso-abbrev">Sci Rep</journal-id><journal-title-group><journal-title>Scientific Reports</journal-title></journal-title-group><issn pub-type="epub">2045-2322</issn><publisher><publisher-name>Nature Publishing Group UK</publisher-name><publisher-loc>London</publisher-loc></publisher></journal-meta><article-meta><article-id pub-id-type="pmid">28811524</article-id><article-id pub-id-type="pmc">5557986</article-id><article-id pub-id-type="publisher-id">7836</article-id><article-id pub-id-type="doi">10.1038/s41598-017-07836-y</article-id><article-categories><subj-group subj-group-type="heading"><subject>Article</subject></subj-group></article-categories><title-group><article-title>Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality</article-title></title-group><contrib-group><contrib contrib-type="author" corresp="yes"><name><surname>Vavricka</surname><given-names>Christopher J.</given-names></name><address><email>chrisv@people.kobe-u.ac.jp</email></address><xref ref-type="aff" rid="Aff1">1</xref><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Muto</surname><given-names>Chiaki</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Hasunuma</surname><given-names>Tomohisa</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Kimura</surname><given-names>Yoshinobu</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author"><name><surname>Araki</surname><given-names>Michihiro</given-names></name><xref ref-type="aff" rid="Aff2">2</xref></contrib><contrib contrib-type="author"><name><surname>Wu</surname><given-names>Yan</given-names></name><xref ref-type="aff" rid="Aff3">3</xref></contrib><contrib contrib-type="author"><name><surname>Gao</surname><given-names>George F.</given-names></name><xref ref-type="aff" rid="Aff3">3</xref></contrib><contrib contrib-type="author"><name><surname>Ohrui</surname><given-names>Hiroshi</given-names></name><xref ref-type="aff" rid="Aff4">4</xref></contrib><contrib contrib-type="author"><name><surname>Izumi</surname><given-names>Minoru</given-names></name><xref ref-type="aff" rid="Aff1">1</xref></contrib><contrib contrib-type="author" corresp="yes"><contrib-id contrib-id-type="orcid">http://orcid.org/0000-0002-1330-6522</contrib-id><name><surname>Kiyota</surname><given-names>Hiromasa</given-names></name><address><email>kiyota@okayama-u.ac.jp</email></address><xref ref-type="aff" rid="Aff1">1</xref></contrib><aff id="Aff1"><label>1</label><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1302 4472</institution-id><institution-id institution-id-type="GRID">grid.261356.5</institution-id><institution>Graduate School of Environmental and Life Science,</institution><institution>Okayama University,</institution></institution-wrap>Okayama, 700-8530 Japan</aff><aff id="Aff2"><label>2</label><institution-wrap><institution-id institution-id-type="ISNI">0000 0001 1092 3077</institution-id><institution-id institution-id-type="GRID">grid.31432.37</institution-id><institution>Graduate School of Science, Technology and Innovation,</institution><institution>Kobe University,</institution></institution-wrap>Kobe, 657-0013 Japan</aff><aff id="Aff3"><label>3</label><institution-wrap><institution-id institution-id-type="ISNI">0000000119573309</institution-id><institution-id institution-id-type="GRID">grid.9227.e</institution-id><institution>CAS Key Laboratory of Pathogenic Microbiology and Immunology, Institute of Microbiology,</institution><institution>Chinese Academy of Sciences,</institution></institution-wrap>Beijing, 100101 China</aff><aff id="Aff4"><label>4</label><institution-wrap><institution-id institution-id-type="GRID">grid.443246.3</institution-id><institution></institution><institution>Yokohama College of Pharmacy,</institution></institution-wrap>Yokohama, 245-0066 Japan</aff></contrib-group><pub-date pub-type="epub"><day>15</day><month>8</month><year>2017</year></pub-date><pub-date pub-type="pmc-release"><day>15</day><month>8</month><year>2017</year></pub-date><pub-date pub-type="collection"><year>2017</year></pub-date><volume>7</volume><elocation-id>8239</elocation-id><history><date date-type="received"><day>7</day><month>2</month><year>2017</year></date><date date-type="accepted"><day>30</day><month>6</month><year>2017</year></date></history><permissions><copyright-statement>© The Author(s) 2017</copyright-statement><license license-type="OpenAccess"><license-p><bold>Open Access</bold> This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit <ext-link ext-link-type="uri" xlink:href="http://creativecommons.org/licenses/by/4.0/">http://creativecommons.org/licenses/by/4.0/</ext-link>.</license-p></license></permissions><abstract id="Abs1"><p id="Par1">The design, synthesis and application of <italic>N</italic>-acetylneuraminic acid-derived compounds bearing anomeric sulfo functional groups are described. These novel compounds, which we refer to as sulfo-sialic acid analogues, include 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>-acetylneuraminic acid and its 4-deoxy-3,4-dehydrogenated pseudoglycal. While 2-decarboxy-2-deoxy-2-sulfo-<italic>N</italic>-acetylneuraminic acid contains no further modifications of the 2-deoxy-pyranose ring, it is still a more potent inhibitor of avian-origin H5N1 neuraminidase (NA) and drug-resistant His275Tyr NA as compared to the oxocarbenium ion transition state analogue 2,3-dehydro-2-deoxy-<italic>N</italic>-acetylneuraminic acid. The sulfo-sialic acid analogues described in this report are also more potent inhibitors of influenza NA (up to 40-fold) and bacterial NA (up to 8.5-fold) relative to the corresponding anomeric phosphonic acids. These results confirm that this novel anomeric sulfo modification offers great potential to improve the potency of next-generation NA inhibitors including covalent inhibitors.</p></abstract><custom-meta-group><custom-meta><meta-name>issue-copyright-statement</meta-name><meta-value>© The Author(s) 2017</meta-value></custom-meta></custom-meta-group></article-meta></front></pmc><affiliations><list><country><li>Japon</li><li>République populaire de Chine</li></country></list><tree><country name="Japon"><noRegion><name sortKey="Vavricka, Christopher J" sort="Vavricka, Christopher J" uniqKey="Vavricka C" first="Christopher J." last="Vavricka">Christopher J. Vavricka</name></noRegion><name sortKey="Araki, Michihiro" sort="Araki, Michihiro" uniqKey="Araki M" first="Michihiro" last="Araki">Michihiro Araki</name><name sortKey="Hasunuma, Tomohisa" sort="Hasunuma, Tomohisa" uniqKey="Hasunuma T" first="Tomohisa" last="Hasunuma">Tomohisa Hasunuma</name><name sortKey="Izumi, Minoru" sort="Izumi, Minoru" uniqKey="Izumi M" first="Minoru" last="Izumi">Minoru Izumi</name><name sortKey="Kimura, Yoshinobu" sort="Kimura, Yoshinobu" uniqKey="Kimura Y" first="Yoshinobu" last="Kimura">Yoshinobu Kimura</name><name sortKey="Kiyota, Hiromasa" sort="Kiyota, Hiromasa" uniqKey="Kiyota H" first="Hiromasa" last="Kiyota">Hiromasa Kiyota</name><name sortKey="Muto, Chiaki" sort="Muto, Chiaki" uniqKey="Muto C" first="Chiaki" last="Muto">Chiaki Muto</name><name sortKey="Ohrui, Hiroshi" sort="Ohrui, Hiroshi" uniqKey="Ohrui H" first="Hiroshi" last="Ohrui">Hiroshi Ohrui</name><name sortKey="Vavricka, Christopher J" sort="Vavricka, Christopher J" uniqKey="Vavricka C" first="Christopher J." last="Vavricka">Christopher J. Vavricka</name></country><country name="République populaire de Chine"><noRegion><name sortKey="Wu, Yan" sort="Wu, Yan" uniqKey="Wu Y" first="Yan" last="Wu">Yan Wu</name></noRegion><name sortKey="Gao, George F" sort="Gao, George F" uniqKey="Gao G" first="George F." last="Gao">George F. Gao</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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