Document Detail


Total synthesis and in vitro-antifungal activity of (+/-)-2-methoxytetradecanoic Acid.
MedLine Citation:
PMID:  15038060     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
The marine fatty acid (+/-)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxy-tetradecanoate. The title compound was antifungal against Candida albicans (ATCC 14053) in RPMI medium and Aspergillus niger (ATCC 16404) and Cryptococcus neoformans (ATCC 66031) in SDB medium at the minimum inhibitory concentration (MIC) of 100 mM, which compares to the fungitoxicity of a 2-iodotetradecanoic acid against the same fungi. The title compound was also five to ten times more cytotoxic than capric acid to C. albicans and A. niger in the tested medium but comparable in cytotoxicity to either capric acid and its 2-methoxylated analog to C. neoformans. The antifungal activity of (+/-)-2-methoxytetradecanoic acid is explained in terms of inhibition of N-myristoyltransferase.
Authors:
Néstor M Carballeira; Denisse Ortiz; Keykavous Parang; Soroush Sardari
Publication Detail:
Type:  Comparative Study; In Vitro; Journal Article; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.    
Journal Detail:
Title:  Archiv der Pharmazie     Volume:  337     ISSN:  0365-6233     ISO Abbreviation:  Arch. Pharm. (Weinheim)     Publication Date:  2004 Mar 
Date Detail:
Created Date:  2004-03-23     Completed Date:  2004-06-10     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0330167     Medline TA:  Arch Pharm (Weinheim)     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  152-5     Citation Subset:  IM    
Affiliation:
Department of Chemistry, University of Puerto Rico, San Juan, Puerto Rico. ncarball@upracd.upr.clu.edu
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MeSH Terms
Descriptor/Qualifier:
Acyltransferases / antagonists & inhibitors,  biosynthesis,  pharmacokinetics
Amphotericin B / pharmacology
Antifungal Agents / chemical synthesis*,  pharmacology*
Aspergillus niger / drug effects
Candida albicans / drug effects
Cryptococcus neoformans / drug effects
Fatty Acids / chemical synthesis
Myristates / chemical synthesis*,  pharmacology*
Myristic Acids / chemical synthesis*,  pharmacology*
Grant Support
ID/Acronym/Agency:
S06GM08102/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/2-methoxytetradecanoic acid; 0/Antifungal Agents; 0/Fatty Acids; 0/Myristates; 0/Myristic Acids; 1397-89-3/Amphotericin B; EC 2.3.-/Acyltransferases; EC 2.3.1.97/glycylpeptide N-tetradecanoyltransferase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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