| First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata. | |
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MedLine Citation:
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PMID: 21129369 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The first total synthesis for the (Z)-16-methyl-11-heptadecenoic acid, a novel fatty acid from the sponge Dragmaxia undata, was accomplished in seven steps and in a 44% overall yield. The use of (trimethylsilyl)acetylene was key in the synthesis. Based on a previous developed strategy in our laboratory the best synthetic route towards the title compound was first acetylide coupling of (trimethylsilyl)acetylene to the long-chain protected 10-bromo-1-decanol followed by a second acetylide coupling to the short-chain 1-bromo-4-methylpentane, which resulted in higher yields. Complete spectral data is also presented for the first time for this recently discovered fatty acid and the cis double bond stereochemistry of the natural acid was established. The title compound displayed antiprotozoal activity against Leishmania donovani (IC(50) = 165.5 ± 23.4 μM) and inhibited the leishmania DNA topoisomerase IB enzyme (LdTopIB) with an IC(50) = 62.3 ± 0.7 μM. |
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Authors:
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Néstor M Carballeira; Nashbly Montano; Gabriel A Cintrón; Carmary Márquez; Celia Fernández Rubio; Christopher Fernández Prada; Rafael Balaña-Fouce |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't Date: 2010-12-01 |
Journal Detail:
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Title: Chemistry and physics of lipids Volume: 164 ISSN: 1873-2941 ISO Abbreviation: Chem. Phys. Lipids Publication Date: 2011 Feb |
Date Detail:
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Created Date: 2011-02-14 Completed Date: 2011-06-16 Revised Date: 2013-05-27 |
Medline Journal Info:
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Nlm Unique ID: 0067206 Medline TA: Chem Phys Lipids Country: Ireland |
Other Details:
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Languages: eng Pagination: 113-7 Citation Subset: IM |
Copyright Information:
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Copyright © 2010 Elsevier Ireland Ltd. All rights reserved. |
Affiliation:
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Department of Chemistry, University of Puerto Rico, San Juan, 00931-3346, USA. nmcarballeira@uprrp.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acetylene
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chemistry Animals Antiprotozoal Agents / chemical synthesis*, chemistry, pharmacology*, toxicity Cell Line DNA Topoisomerases, Type I / metabolism Fatty Acids / chemical synthesis*, chemistry, pharmacology*, toxicity Fatty Acids, Monounsaturated / chemical synthesis*, chemistry, pharmacology*, toxicity Indicators and Reagents / chemistry Leishmania donovani / drug effects*, enzymology Macrophages / drug effects Mice Porifera / chemistry* Stereoisomerism Topoisomerase Inhibitors / chemical synthesis, chemistry, pharmacology, toxicity |
| Grant Support | |
ID/Acronym/Agency:
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SC1 GM084708-03/GM/NIGMS NIH HHS; SC1 GM084708-04/GM/NIGMS NIH HHS; SC1GM084708/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/16-methyl-8-heptadecenoic acid; 0/Antiprotozoal Agents; 0/Fatty Acids; 0/Fatty Acids, Monounsaturated; 0/Indicators and Reagents; 0/Topoisomerase Inhibitors; 74-86-2/Acetylene; EC 5.99.1.2/DNA Topoisomerases, Type I |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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