Design, synthesis and in vivo activity of 9-( S)-dihydroerythromycin derivatives as potent anti-inflammatory agents
The synthesis of a new class of 9-( S)-dihydroerythromycin derivatives and their anti-inflammatory activity are reported. The synthesis of a new class of 9-( S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on...
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| Veröffentlicht in: | Bioorganic & medicinal chemistry letters 2006-11, Vol.16 (22), p.5801-5804 |
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| container_title | Bioorganic & medicinal chemistry letters |
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| creator | Mereu, A. Moriggi, E. Napoletano, M. Regazzoni, C. Manfredini, S. Mercurio, T.P. Pellacini, F. |
| description | The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity are reported.
The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3′ amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents. |
| doi_str_mv | 10.1016/j.bmcl.2006.08.076 |
| format | Article |
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S)-dihydroerythromycin derivatives and their anti-inflammatory activity are reported.
The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3′ amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents.</description><identifier>ISSN: 0960-894X</identifier><identifier>EISSN: 1464-3405</identifier><identifier>DOI: 10.1016/j.bmcl.2006.08.076</identifier><identifier>PMID: 16982191</identifier><language>eng</language><publisher>Oxford: Elsevier Ltd</publisher><subject>amide ; Amine ; Amino Sugars - chemistry ; Animals ; Anti-inflammatory ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - therapeutic use ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; CD1 mice ; Cladinose ; Desosamine ; Disease Models, Animal ; Dose-Response Relationship, Drug ; Drug Design ; Edema - drug therapy ; Edema - pathology ; Erythromycin ; Erythromycin - analogs & derivatives ; Erythromycin - chemical synthesis ; Erythromycin - pharmacology ; Erythromycin - therapeutic use ; Erythronoid ; Macrolide ; Medical sciences ; Mice ; Pharmacology. Drug treatments ; PMA induced ear edema</subject><ispartof>Bioorganic & medicinal chemistry letters, 2006-11, Vol.16 (22), p.5801-5804</ispartof><rights>2006 Elsevier Ltd</rights><rights>2007 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c384t-ea6ce939139dc935bf7f178037b26b5c9fb4783e77d2b9d6d625989225d9912d3</citedby><cites>FETCH-LOGICAL-c384t-ea6ce939139dc935bf7f178037b26b5c9fb4783e77d2b9d6d625989225d9912d3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.bmcl.2006.08.076$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=18207195$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16982191$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mereu, A.</creatorcontrib><creatorcontrib>Moriggi, E.</creatorcontrib><creatorcontrib>Napoletano, M.</creatorcontrib><creatorcontrib>Regazzoni, C.</creatorcontrib><creatorcontrib>Manfredini, S.</creatorcontrib><creatorcontrib>Mercurio, T.P.</creatorcontrib><creatorcontrib>Pellacini, F.</creatorcontrib><title>Design, synthesis and in vivo activity of 9-( S)-dihydroerythromycin derivatives as potent anti-inflammatory agents</title><title>Bioorganic & medicinal chemistry letters</title><addtitle>Bioorg Med Chem Lett</addtitle><description>The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity are reported.
The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3′ amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents.</description><subject>amide</subject><subject>Amine</subject><subject>Amino Sugars - chemistry</subject><subject>Animals</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - therapeutic use</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>CD1 mice</subject><subject>Cladinose</subject><subject>Desosamine</subject><subject>Disease Models, Animal</subject><subject>Dose-Response Relationship, Drug</subject><subject>Drug Design</subject><subject>Edema - drug therapy</subject><subject>Edema - pathology</subject><subject>Erythromycin</subject><subject>Erythromycin - analogs & derivatives</subject><subject>Erythromycin - chemical synthesis</subject><subject>Erythromycin - pharmacology</subject><subject>Erythromycin - therapeutic use</subject><subject>Erythronoid</subject><subject>Macrolide</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Pharmacology. Drug treatments</subject><subject>PMA induced ear edema</subject><issn>0960-894X</issn><issn>1464-3405</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kEGL1DAYhoO4uOPqH_AguSgK25qkbZqAF1l1V1jwoIK3kCZfdzK0yWySKfTfm2EG9uYpH-F53-_jQegNJTUllH_a1cNsppoRwmsiatLzZ2hDW95WTUu652hDJCeVkO3fS_QypR0htCVt-wJdUi4Fo5JuUPoKyT34a5xWn7dlTlh7i53Hi1sC1ia7xeUVhxHL6gP-9bGybrvaGCCueRvDvJrCWohu0QWFEk94HzL4XIqyq5wfJz3POoe4Yv1Q_tMrdDHqKcHr83uF_nz_9vvmrrr_efvj5st9ZRrR5go0NyAbSRtpjWy6YexH2gvS9APjQ2fkOLS9aKDvLRuk5ZazTgrJWGelpMw2V-j9qXcfw-MBUlazSwamSXsIh6S4kA2jrCsgO4EmhpQijGof3azjqihRR9Vqp46q1VG1IkIV1SX09tx-GGawT5Gz2wK8OwM6GT2NUXvj0hMnGOmpPG7_fOKguFgcRJWMA2_AuggmKxvc_-74BzBbneQ</recordid><startdate>20061115</startdate><enddate>20061115</enddate><creator>Mereu, A.</creator><creator>Moriggi, E.</creator><creator>Napoletano, M.</creator><creator>Regazzoni, C.</creator><creator>Manfredini, S.</creator><creator>Mercurio, T.P.</creator><creator>Pellacini, F.</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>20061115</creationdate><title>Design, synthesis and in vivo activity of 9-( S)-dihydroerythromycin derivatives as potent anti-inflammatory agents</title><author>Mereu, A. ; Moriggi, E. ; Napoletano, M. ; Regazzoni, C. ; Manfredini, S. ; Mercurio, T.P. ; Pellacini, F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c384t-ea6ce939139dc935bf7f178037b26b5c9fb4783e77d2b9d6d625989225d9912d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2006</creationdate><topic>amide</topic><topic>Amine</topic><topic>Amino Sugars - chemistry</topic><topic>Animals</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - therapeutic use</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>CD1 mice</topic><topic>Cladinose</topic><topic>Desosamine</topic><topic>Disease Models, Animal</topic><topic>Dose-Response Relationship, Drug</topic><topic>Drug Design</topic><topic>Edema - drug therapy</topic><topic>Edema - pathology</topic><topic>Erythromycin</topic><topic>Erythromycin - analogs & derivatives</topic><topic>Erythromycin - chemical synthesis</topic><topic>Erythromycin - pharmacology</topic><topic>Erythromycin - therapeutic use</topic><topic>Erythronoid</topic><topic>Macrolide</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Pharmacology. Drug treatments</topic><topic>PMA induced ear edema</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mereu, A.</creatorcontrib><creatorcontrib>Moriggi, E.</creatorcontrib><creatorcontrib>Napoletano, M.</creatorcontrib><creatorcontrib>Regazzoni, C.</creatorcontrib><creatorcontrib>Manfredini, S.</creatorcontrib><creatorcontrib>Mercurio, T.P.</creatorcontrib><creatorcontrib>Pellacini, F.</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 letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mereu, A.</au><au>Moriggi, E.</au><au>Napoletano, M.</au><au>Regazzoni, C.</au><au>Manfredini, S.</au><au>Mercurio, T.P.</au><au>Pellacini, F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Design, synthesis and in vivo activity of 9-( S)-dihydroerythromycin derivatives as potent anti-inflammatory agents</atitle><jtitle>Bioorganic & medicinal chemistry letters</jtitle><addtitle>Bioorg Med Chem Lett</addtitle><date>2006-11-15</date><risdate>2006</risdate><volume>16</volume><issue>22</issue><spage>5801</spage><epage>5804</epage><pages>5801-5804</pages><issn>0960-894X</issn><eissn>1464-3405</eissn><abstract>The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity are reported.
The synthesis of a new class of 9-(
S)-dihydroerythromycin derivatives and their anti-inflammatory activity on in vivo PMA assay are described. Modifying the desosamine sugar on the C-3′ amino group, it was possible to differentiate between anti-biotic and anti-flammatory action. The compounds are completely devoid of anti-microbial effects but their anti-inflammatory properties are enhanced. These results strongly suggest the potential of macrolides as a new class of anti-inflammatory agents.</abstract><cop>Oxford</cop><pub>Elsevier Ltd</pub><pmid>16982191</pmid><doi>10.1016/j.bmcl.2006.08.076</doi><tpages>4</tpages></addata></record> |
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| subjects | amide Amine Amino Sugars - chemistry Animals Anti-inflammatory Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - therapeutic use Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents CD1 mice Cladinose Desosamine Disease Models, Animal Dose-Response Relationship, Drug Drug Design Edema - drug therapy Edema - pathology Erythromycin Erythromycin - analogs & derivatives Erythromycin - chemical synthesis Erythromycin - pharmacology Erythromycin - therapeutic use Erythronoid Macrolide Medical sciences Mice Pharmacology. Drug treatments PMA induced ear edema |
| title | Design, synthesis and in vivo activity of 9-( S)-dihydroerythromycin derivatives as potent anti-inflammatory agents |
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