| Total synthesis and in vitro-antifungal activity of (+/-)-2-methoxytetradecanoic Acid. | |
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MedLine Citation:
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PMID: 15038060 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Néstor M Carballeira; Denisse Ortiz; Keykavous Parang; Soroush Sardari |
Publication Detail:
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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:
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Title: Archiv der Pharmazie Volume: 337 ISSN: 0365-6233 ISO Abbreviation: Arch. Pharm. (Weinheim) Publication Date: 2004 Mar |
Date Detail:
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Created Date: 2004-03-23 Completed Date: 2004-06-10 Revised Date: 2007-11-14 |
Medline Journal Info:
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Nlm Unique ID: 0330167 Medline TA: Arch Pharm (Weinheim) Country: Germany |
Other Details:
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Languages: eng Pagination: 152-5 Citation Subset: IM |
Affiliation:
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Department of Chemistry, University of Puerto Rico, San Juan, Puerto Rico. ncarball@upracd.upr.clu.edu |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Acyltransferases
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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:
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S06GM08102/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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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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