Synthesis of Sulfo-Sialic Acid Analogues: Potent Neuraminidase Inhibitors in Regards to Anomeric Functionality
Identifieur interne : 000018 ( 1957/Analysis ); précédent : 000017; suivant : 000019Synthesis 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
Affiliations:
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PMC:5557986Le document en format XML
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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 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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><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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