Document Detail


First total synthesis and antileishmanial activity of (Z)-16-methyl-11-heptadecenoic acid, a new marine fatty acid from the sponge Dragmaxia undata.
MedLine Citation:
PMID:  21129369     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
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:
Type:  Journal Article; Research Support, N.I.H., Extramural; Research Support, Non-U.S. Gov't     Date:  2010-12-01
Journal Detail:
Title:  Chemistry and physics of lipids     Volume:  164     ISSN:  1873-2941     ISO Abbreviation:  Chem. Phys. Lipids     Publication Date:  2011 Feb 
Date Detail:
Created Date:  2011-02-14     Completed Date:  2011-06-16     Revised Date:  2013-07-03    
Medline Journal Info:
Nlm Unique ID:  0067206     Medline TA:  Chem Phys Lipids     Country:  Ireland    
Other Details:
Languages:  eng     Pagination:  113-7     Citation Subset:  IM    
Copyright Information:
Copyright © 2010 Elsevier Ireland Ltd. All rights reserved.
Affiliation:
Department of Chemistry, University of Puerto Rico, San Juan, 00931-3346, USA. nmcarballeira@uprrp.edu
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MeSH Terms
Descriptor/Qualifier:
Acetylene / 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:
SC1 GM084708-03/GM/NIGMS NIH HHS; SC1 GM084708-04/GM/NIGMS NIH HHS; SC1GM084708/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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

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