An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses
The compound Neu5Ac3αF-DSPE (4), in which the C-3 position was modified with an axial fluorine atom, inhibited the catalytic hydrolysis of influenza virus sialidase and the binding activity of hemagglutinin. The inhibitory activities to sialidases were independent of virus isolates examined. With th...
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| Veröffentlicht in: | Glycobiology (Oxford) 2002-03, Vol.12 (3), p.183-190 |
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| container_title | Glycobiology (Oxford) |
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| creator | Guo, Chao-Tan Sun, Xue-Long Kanie, Osamu Shortridge, Kennedy Francis Suzuki, Takashi Miyamoto, Daisei Hidari, Kazuya I.-P. Jwa Wong, Chi-Huey Suzuki, Yasuo |
| description | The compound Neu5Ac3αF-DSPE (4), in which the C-3 position was modified with an axial fluorine atom, inhibited the catalytic hydrolysis of influenza virus sialidase and the binding activity of hemagglutinin. The inhibitory activities to sialidases were independent of virus isolates examined. With the positive results obtained for inhibition of hemagglutination and hemolysis induced by A/Aichi/2/68 virus, the inhibitory effect of Neu5Ac3αF-DSPE (4) against MDCK cells was examined, and it was found that 4 inhibits the viral infection with IC50 value of 5.6 µM based on the cytopathic effects. The experimental results indicate that compound 4 not only inhibits the attachment of virus to the cell surface receptor but also disturbs the release of the progeny viruses from infected cells by inhibiting both hemagglutinin and sialidase of the influenza viruses. The study suggested that the compound is a new class of bifunctional drug candidates for the future chemotherapy of influenza. |
| doi_str_mv | 10.1093/glycob/12.3.183 |
| format | Article |
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Jwa ; Wong, Chi-Huey ; Suzuki, Yasuo</creator><creatorcontrib>Guo, Chao-Tan ; Sun, Xue-Long ; Kanie, Osamu ; Shortridge, Kennedy Francis ; Suzuki, Takashi ; Miyamoto, Daisei ; Hidari, Kazuya I.-P. Jwa ; Wong, Chi-Huey ; Suzuki, Yasuo</creatorcontrib><description>The compound Neu5Ac3αF-DSPE (4), in which the C-3 position was modified with an axial fluorine atom, inhibited the catalytic hydrolysis of influenza virus sialidase and the binding activity of hemagglutinin. The inhibitory activities to sialidases were independent of virus isolates examined. With the positive results obtained for inhibition of hemagglutination and hemolysis induced by A/Aichi/2/68 virus, the inhibitory effect of Neu5Ac3αF-DSPE (4) against MDCK cells was examined, and it was found that 4 inhibits the viral infection with IC50 value of 5.6 µM based on the cytopathic effects. The experimental results indicate that compound 4 not only inhibits the attachment of virus to the cell surface receptor but also disturbs the release of the progeny viruses from infected cells by inhibiting both hemagglutinin and sialidase of the influenza viruses. The study suggested that the compound is a new class of bifunctional drug candidates for the future chemotherapy of influenza.</description><identifier>ISSN: 0959-6658</identifier><identifier>EISSN: 1460-2423</identifier><identifier>DOI: 10.1093/glycob/12.3.183</identifier><identifier>PMID: 11971862</identifier><language>eng</language><publisher>England: Oxford University Press</publisher><subject>Binding Sites ; Carbohydrate Conformation ; Erythrocytes - immunology ; Glycosides - chemistry ; Glycosides - pharmacology ; Hemagglutination - drug effects ; Hemolysis - drug effects ; Humans ; Hydrogen-Ion Concentration ; Influenza A virus - enzymology ; Influenza virus ; Key words: hemagglutinin/influenza virus/inhibitors/resistance/sialidase ; Kinetics ; Liposomes ; Models, Molecular ; Neuraminidase - antagonists & inhibitors ; Sialic Acids - chemistry ; Sialic Acids - pharmacology</subject><ispartof>Glycobiology (Oxford), 2002-03, Vol.12 (3), p.183-190</ispartof><rights>Copyright Oxford University Press(England) Mar 1, 2002</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c430t-8354ca35882b5429bb9f353d34c5cb36a7762be06b880b445c5f388f289f79743</citedby><cites>FETCH-LOGICAL-c430t-8354ca35882b5429bb9f353d34c5cb36a7762be06b880b445c5f388f289f79743</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/11971862$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Guo, Chao-Tan</creatorcontrib><creatorcontrib>Sun, Xue-Long</creatorcontrib><creatorcontrib>Kanie, Osamu</creatorcontrib><creatorcontrib>Shortridge, Kennedy Francis</creatorcontrib><creatorcontrib>Suzuki, Takashi</creatorcontrib><creatorcontrib>Miyamoto, Daisei</creatorcontrib><creatorcontrib>Hidari, Kazuya I.-P. Jwa</creatorcontrib><creatorcontrib>Wong, Chi-Huey</creatorcontrib><creatorcontrib>Suzuki, Yasuo</creatorcontrib><title>An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses</title><title>Glycobiology (Oxford)</title><addtitle>Glycobiology</addtitle><description>The compound Neu5Ac3αF-DSPE (4), in which the C-3 position was modified with an axial fluorine atom, inhibited the catalytic hydrolysis of influenza virus sialidase and the binding activity of hemagglutinin. The inhibitory activities to sialidases were independent of virus isolates examined. With the positive results obtained for inhibition of hemagglutination and hemolysis induced by A/Aichi/2/68 virus, the inhibitory effect of Neu5Ac3αF-DSPE (4) against MDCK cells was examined, and it was found that 4 inhibits the viral infection with IC50 value of 5.6 µM based on the cytopathic effects. The experimental results indicate that compound 4 not only inhibits the attachment of virus to the cell surface receptor but also disturbs the release of the progeny viruses from infected cells by inhibiting both hemagglutinin and sialidase of the influenza viruses. The study suggested that the compound is a new class of bifunctional drug candidates for the future chemotherapy of influenza.</description><subject>Binding Sites</subject><subject>Carbohydrate Conformation</subject><subject>Erythrocytes - immunology</subject><subject>Glycosides - chemistry</subject><subject>Glycosides - pharmacology</subject><subject>Hemagglutination - drug effects</subject><subject>Hemolysis - drug effects</subject><subject>Humans</subject><subject>Hydrogen-Ion Concentration</subject><subject>Influenza A virus - enzymology</subject><subject>Influenza virus</subject><subject>Key words: hemagglutinin/influenza virus/inhibitors/resistance/sialidase</subject><subject>Kinetics</subject><subject>Liposomes</subject><subject>Models, Molecular</subject><subject>Neuraminidase - antagonists & inhibitors</subject><subject>Sialic Acids - chemistry</subject><subject>Sialic Acids - pharmacology</subject><issn>0959-6658</issn><issn>1460-2423</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2002</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkc1v0zAYhy0EYt3gzA1ZHLiltf36K8epwAaaNPElTVws23FajzQZtlMYfz0pqUDiwsmH93keyfoh9IySJSU1rDbdvR_cirIlLKmGB2hBuSQV4wweogWpRV1JKfQJOs35lhAqqRaP0QmltaJasgX6ft7j6-p3Jscm4KHFOdouemx9bHATUtzbEvcBl60tOPbb6GLJ2A1li7dhZzebbiyxjz22fTO7jc1h0icrlhjyoRn7thtD_9PifUxjDvkJetTaLoenx_cMfX7z-tP6srq6vni7Pr-qPAdSKg2CewtCa-YEZ7VzdQsCGuBeeAfSKiWZC0Q6rYnjXHjRgtYt03WrasXhDL2cu3dp-DaGXMwuZh-6zvZhGLNRVDJQXP0XZIRzzZWewBf_gLfDmPrpE4ZRAlCDONRWM-TTkHMKrblLcWfTvaHEHJYz83KGMgNmWm4ynh-zo9uF5i9_nGoCqhmIuYQff-42fTVSgRLm8uaLefXh5uP7d3xtCPwCOIWlSQ</recordid><startdate>20020301</startdate><enddate>20020301</enddate><creator>Guo, Chao-Tan</creator><creator>Sun, Xue-Long</creator><creator>Kanie, Osamu</creator><creator>Shortridge, Kennedy Francis</creator><creator>Suzuki, Takashi</creator><creator>Miyamoto, Daisei</creator><creator>Hidari, Kazuya I.-P. 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| source | MEDLINE; Oxford University Press Journals All Titles (1996-Current); EZB-FREE-00999 freely available EZB journals; Alma/SFX Local Collection |
| subjects | Binding Sites Carbohydrate Conformation Erythrocytes - immunology Glycosides - chemistry Glycosides - pharmacology Hemagglutination - drug effects Hemolysis - drug effects Humans Hydrogen-Ion Concentration Influenza A virus - enzymology Influenza virus Key words: hemagglutinin/influenza virus/inhibitors/resistance/sialidase Kinetics Liposomes Models, Molecular Neuraminidase - antagonists & inhibitors Sialic Acids - chemistry Sialic Acids - pharmacology |
| title | An O-glycoside of sialic acid derivative that inhibits both hemagglutinin and sialidase activities of influenza viruses |
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