Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses
A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Acα2→3Galβ1→4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had un...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry 2009-08, Vol.17 (15), p.5465-5475 |
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| creator | Oka, Hiroyuki Onaga, Tomotsune Koyama, Tetsuo Guo, Chao-Tan Suzuki, Yasuo Esumi, Yasuaki Hatano, Ken Terunuma, Daiyo Matsuoka, Koji |
| description | A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Acα2→3Galβ1→4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycodendrimer
7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure–activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study. |
| doi_str_mv | 10.1016/j.bmc.2009.06.035 |
| format | Article |
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7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure–activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study.</description><identifier>ISSN: 0968-0896</identifier><identifier>EISSN: 1464-3391</identifier><identifier>DOI: 10.1016/j.bmc.2009.06.035</identifier><identifier>PMID: 19589684</identifier><language>eng</language><publisher>Amsterdam: Elsevier Ltd</publisher><subject>Animals ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antiviral agents ; Antiviral Agents - chemical synthesis ; Antiviral Agents - chemistry ; Antiviral Agents - pharmacology ; Biological and medical sciences ; Carbosilanes ; Cell Line ; Dendrimers ; Dendrimers - chemical synthesis ; Dendrimers - chemistry ; Dendrimers - pharmacology ; Dogs ; Erythrocytes - cytology ; Erythrocytes - virology ; Glycoclusters ; Hemagglutination - drug effects ; Hemagglutinin ; Hemolysis - drug effects ; Humans ; Influenza A virus - drug effects ; Influenza A virus - pathogenicity ; Influenza A Virus, H1N1 Subtype - drug effects ; Influenza A Virus, H1N1 Subtype - pathogenicity ; Influenza A Virus, H3N2 Subtype - drug effects ; Influenza A Virus, H3N2 Subtype - pathogenicity ; Influenza virus ; Influenza, Human - drug therapy ; Kidney - cytology ; Kidney - virology ; Lactose - chemistry ; Medical sciences ; Molecular Structure ; N-Acetylneuraminic Acid - chemistry ; Pharmacology. Drug treatments ; Sialic acid ; Sialyl lactose ; Silanes - chemical synthesis ; Silanes - chemistry ; Silanes - pharmacology ; Structure-Activity Relationship</subject><ispartof>Bioorganic & medicinal chemistry, 2009-08, Vol.17 (15), p.5465-5475</ispartof><rights>2009 Elsevier Ltd</rights><rights>2009 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c381t-965d277d0544a1c646b0ef64f09e9fe2ec58fd0df6dd8db9459c8486feca9bc53</citedby><cites>FETCH-LOGICAL-c381t-965d277d0544a1c646b0ef64f09e9fe2ec58fd0df6dd8db9459c8486feca9bc53</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmc.2009.06.035$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>315,781,785,3551,27926,27927,45997</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=21790190$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19589684$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Oka, Hiroyuki</creatorcontrib><creatorcontrib>Onaga, Tomotsune</creatorcontrib><creatorcontrib>Koyama, Tetsuo</creatorcontrib><creatorcontrib>Guo, Chao-Tan</creatorcontrib><creatorcontrib>Suzuki, Yasuo</creatorcontrib><creatorcontrib>Esumi, Yasuaki</creatorcontrib><creatorcontrib>Hatano, Ken</creatorcontrib><creatorcontrib>Terunuma, Daiyo</creatorcontrib><creatorcontrib>Matsuoka, Koji</creatorcontrib><title>Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses</title><title>Bioorganic & medicinal chemistry</title><addtitle>Bioorg Med Chem</addtitle><description>A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Acα2→3Galβ1→4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycodendrimer
7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure–activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study.</description><subject>Animals</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antiviral agents</subject><subject>Antiviral Agents - chemical synthesis</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - pharmacology</subject><subject>Biological and medical sciences</subject><subject>Carbosilanes</subject><subject>Cell Line</subject><subject>Dendrimers</subject><subject>Dendrimers - chemical synthesis</subject><subject>Dendrimers - chemistry</subject><subject>Dendrimers - pharmacology</subject><subject>Dogs</subject><subject>Erythrocytes - cytology</subject><subject>Erythrocytes - virology</subject><subject>Glycoclusters</subject><subject>Hemagglutination - drug effects</subject><subject>Hemagglutinin</subject><subject>Hemolysis - drug effects</subject><subject>Humans</subject><subject>Influenza A virus - drug effects</subject><subject>Influenza A virus - pathogenicity</subject><subject>Influenza A Virus, H1N1 Subtype - drug effects</subject><subject>Influenza A Virus, H1N1 Subtype - pathogenicity</subject><subject>Influenza A Virus, H3N2 Subtype - drug effects</subject><subject>Influenza A Virus, H3N2 Subtype - pathogenicity</subject><subject>Influenza virus</subject><subject>Influenza, Human - drug therapy</subject><subject>Kidney - cytology</subject><subject>Kidney - virology</subject><subject>Lactose - chemistry</subject><subject>Medical sciences</subject><subject>Molecular Structure</subject><subject>N-Acetylneuraminic Acid - chemistry</subject><subject>Pharmacology. Drug treatments</subject><subject>Sialic acid</subject><subject>Sialyl lactose</subject><subject>Silanes - chemical synthesis</subject><subject>Silanes - chemistry</subject><subject>Silanes - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0968-0896</issn><issn>1464-3391</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kUGO1DAQRSMEYnoGDsAGeQOCRQc7cZxYrNCIAaSRWABry7HLdLUce7CTRj0H4ACcgi0X4RCcBLe6BTtWlkqvvqvqVdUjRmtGmXixrcfJ1A2lsqaipm13p1oxLvi6bSW7W62oFMOaDlKcVec5bymlDZfsfnXGZFeqA19VPz7sw7yBDJnoYMmI0cfPaLQnsNN-0TPGkEl0xOg0xoxeByAWgk04QcpkCehimvyeuCWYA6093oIlX3HekIza7z359fNZ8_vb9_Y58drMMQOZIsKMh08zwbDBEedY0koU2SyTDqXo_ALhVpMdpqWM96C657TP8PD0XlSfrl5_vHy7vn7_5t3lq-u1aQc2r6XobNP3lnaca2YEFyMFJ7ijEqSDBkw3OEutE9YOdpS8k2bgg3BgtBxN115UT4-5Nyl-WSDPasJswB8Wj0tWou8o56wvIDuCJsWcEzh1U26i014xqg561FYVPeqgR1Ghip7S8_gUvowT2H8dJx8FeHICdC4SXNLBYP7LNayXlElauJdHDsopdghJZYMQDFhMYGZlI_5njD-fuLR_</recordid><startdate>20090801</startdate><enddate>20090801</enddate><creator>Oka, Hiroyuki</creator><creator>Onaga, Tomotsune</creator><creator>Koyama, Tetsuo</creator><creator>Guo, Chao-Tan</creator><creator>Suzuki, Yasuo</creator><creator>Esumi, Yasuaki</creator><creator>Hatano, Ken</creator><creator>Terunuma, Daiyo</creator><creator>Matsuoka, Koji</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20090801</creationdate><title>Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses</title><author>Oka, Hiroyuki ; Onaga, Tomotsune ; Koyama, Tetsuo ; Guo, Chao-Tan ; Suzuki, Yasuo ; Esumi, Yasuaki ; Hatano, Ken ; Terunuma, Daiyo ; Matsuoka, Koji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c381t-965d277d0544a1c646b0ef64f09e9fe2ec58fd0df6dd8db9459c8486feca9bc53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Animals</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antiviral agents</topic><topic>Antiviral Agents - chemical synthesis</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - pharmacology</topic><topic>Biological and medical sciences</topic><topic>Carbosilanes</topic><topic>Cell Line</topic><topic>Dendrimers</topic><topic>Dendrimers - chemical synthesis</topic><topic>Dendrimers - chemistry</topic><topic>Dendrimers - pharmacology</topic><topic>Dogs</topic><topic>Erythrocytes - cytology</topic><topic>Erythrocytes - virology</topic><topic>Glycoclusters</topic><topic>Hemagglutination - drug effects</topic><topic>Hemagglutinin</topic><topic>Hemolysis - drug effects</topic><topic>Humans</topic><topic>Influenza A virus - drug effects</topic><topic>Influenza A virus - pathogenicity</topic><topic>Influenza A Virus, H1N1 Subtype - drug effects</topic><topic>Influenza A Virus, H1N1 Subtype - pathogenicity</topic><topic>Influenza A Virus, H3N2 Subtype - drug effects</topic><topic>Influenza A Virus, H3N2 Subtype - pathogenicity</topic><topic>Influenza virus</topic><topic>Influenza, Human - drug therapy</topic><topic>Kidney - cytology</topic><topic>Kidney - virology</topic><topic>Lactose - chemistry</topic><topic>Medical sciences</topic><topic>Molecular Structure</topic><topic>N-Acetylneuraminic Acid - chemistry</topic><topic>Pharmacology. Drug treatments</topic><topic>Sialic acid</topic><topic>Sialyl lactose</topic><topic>Silanes - chemical synthesis</topic><topic>Silanes - chemistry</topic><topic>Silanes - pharmacology</topic><topic>Structure-Activity Relationship</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Oka, Hiroyuki</creatorcontrib><creatorcontrib>Onaga, Tomotsune</creatorcontrib><creatorcontrib>Koyama, Tetsuo</creatorcontrib><creatorcontrib>Guo, Chao-Tan</creatorcontrib><creatorcontrib>Suzuki, Yasuo</creatorcontrib><creatorcontrib>Esumi, Yasuaki</creatorcontrib><creatorcontrib>Hatano, Ken</creatorcontrib><creatorcontrib>Terunuma, Daiyo</creatorcontrib><creatorcontrib>Matsuoka, Koji</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Bioorganic & medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Oka, Hiroyuki</au><au>Onaga, Tomotsune</au><au>Koyama, Tetsuo</au><au>Guo, Chao-Tan</au><au>Suzuki, Yasuo</au><au>Esumi, Yasuaki</au><au>Hatano, Ken</au><au>Terunuma, Daiyo</au><au>Matsuoka, Koji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses</atitle><jtitle>Bioorganic & medicinal chemistry</jtitle><addtitle>Bioorg Med Chem</addtitle><date>2009-08-01</date><risdate>2009</risdate><volume>17</volume><issue>15</issue><spage>5465</spage><epage>5475</epage><pages>5465-5475</pages><issn>0968-0896</issn><eissn>1464-3391</eissn><abstract>A series of carbosilane dendrimers uniformly functionalized with sialyl lactose moieties (Neu5Acα2→3Galβ1→4Glc) was systematically synthesized, and biological evaluations for anti-influenza virus activity using the glycodendrimers were performed. The results suggested that the glycodendrimers had unique biological activities depending on the form of their core frame, and Dumbbell(1)6-amide type glycodendrimer
7 showed particularly strong inhibitory activities against human influenza viruses [A/PR/8/34 (H1N1) and A/Aichi/2/68 (H3N2)]. The results suggested that the structure–activity relationship (SAR) on the glycolibrary against various influenza viruses was observed, and dumbbell-shaped dendrimers as supporting carbohydrate moieties were found to be the most suitable core scaffolds in this study.</abstract><cop>Amsterdam</cop><pub>Elsevier Ltd</pub><pmid>19589684</pmid><doi>10.1016/j.bmc.2009.06.035</doi><tpages>11</tpages></addata></record> |
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| ispartof | Bioorganic & medicinal chemistry, 2009-08, Vol.17 (15), p.5465-5475 |
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| source | MEDLINE; Elsevier ScienceDirect Journals Complete |
| subjects | Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antiviral agents Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - pharmacology Biological and medical sciences Carbosilanes Cell Line Dendrimers Dendrimers - chemical synthesis Dendrimers - chemistry Dendrimers - pharmacology Dogs Erythrocytes - cytology Erythrocytes - virology Glycoclusters Hemagglutination - drug effects Hemagglutinin Hemolysis - drug effects Humans Influenza A virus - drug effects Influenza A virus - pathogenicity Influenza A Virus, H1N1 Subtype - drug effects Influenza A Virus, H1N1 Subtype - pathogenicity Influenza A Virus, H3N2 Subtype - drug effects Influenza A Virus, H3N2 Subtype - pathogenicity Influenza virus Influenza, Human - drug therapy Kidney - cytology Kidney - virology Lactose - chemistry Medical sciences Molecular Structure N-Acetylneuraminic Acid - chemistry Pharmacology. Drug treatments Sialic acid Sialyl lactose Silanes - chemical synthesis Silanes - chemistry Silanes - pharmacology Structure-Activity Relationship |
| title | Syntheses and biological evaluations of carbosilane dendrimers uniformly functionalized with sialyl α(2→3) lactose moieties as inhibitors for human influenza viruses |
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