| The influence of the long chain fatty acid on the antagonistic activities of Rhizobium sin-1 lipid A. | |
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MedLine Citation:
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PMID: 17513113 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The lipid A from nitrogen-fixing bacterial species Rhizobium sin-1 is structurally unusual due to lack of phosphates and the presence of a 2-aminogluconolactone and a very long chain fatty acid, 27-hydroxyoctacosanoic acid (27OHC28:0), moiety. This structurally unusual lipid A can antagonize TNF-alpha production by human monocytes induced by Escherichia coli LPS. To establish the relevance of the unusual long chain 27-hydroxyoctacosanoic acid for antagonistic properties, a highly convergent strategy for the synthesis of several derivatives of the lipid A of R. sin-1 has been developed. Compound 1 is a natural R. sin-1 lipid A having a 27-hydroxyoctacosanoic acid at C-2', compound 2 contains an octacosanoic acid moiety at this position, and compound 3 is modified by a short chain tetradecanoic acid. Cellular activation studies with a human monocytic cell line have shown that the octacosanoic acid is important for optimal antagonistic properties. The hydroxyl of the natural 27-hydroxyoctacosanoic moiety does, however, not account for inhibitory activity. The resulting structure-activity relationships are important for the design of compounds for the treatment of septic shock. |
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Authors:
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Yanghui Zhang; Margreet A Wolfert; Geert-Jan Boons |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2007-05-06 |
Journal Detail:
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Title: Bioorganic & medicinal chemistry Volume: 15 ISSN: 0968-0896 ISO Abbreviation: Bioorg. Med. Chem. Publication Date: 2007 Jul |
Date Detail:
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Created Date: 2007-06-06 Completed Date: 2007-08-08 Revised Date: 2011-06-16 |
Medline Journal Info:
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Nlm Unique ID: 9413298 Medline TA: Bioorg Med Chem Country: England |
Other Details:
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Languages: eng Pagination: 4800-12 Citation Subset: IM |
Affiliation:
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Complex Carbohydrate Research Center, The University of Georgia, 315 Riverbend Road, Athens, GA 30602, USA. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cell Line Fatty Acids / chemical synthesis, chemistry*, pharmacology* Humans Lipid A / antagonists & inhibitors*, metabolism Molecular Structure Monocytes / drug effects, metabolism Rhizobium / metabolism* Structure-Activity Relationship |
| Grant Support | |
ID/Acronym/Agency:
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GM061761/GM/NIGMS NIH HHS; R01 GM061761-06A1/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Fatty Acids; 0/Lipid A |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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