Total synthesis and in vitro-antifungal activity of (±)-2- methoxytetradecanoic acid

Néstor M. Carballeira; Denisse Ortiz; Keykavous Parang; Soroush Sardari

doi:10.1002/ardp.200300824

Total synthesis and in vitro-antifungal activity of (±)-2- methoxytetradecanoic acid

Néstor M. Carballeira, Denisse Ortiz, Keykavous Parang, Soroush Sardari

Research output: Contribution to journal › Article › peer-review

14 Scopus citations

Abstract

The marine fatty acid (±)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxytetradecanoate. 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.

Original language	English (US)
Pages (from-to)	152-155
Number of pages	4
Journal	Archiv der Pharmazie
Volume	337
Issue number	3
DOIs	https://doi.org/10.1002/ardp.200300824
State	Published - Mar 2004
Externally published	Yes

Keywords

2-Methoxytetradecanoic acid
Antifungal activity
Myristic acid
N-Myristoyltransferase

ASJC Scopus subject areas

Drug Discovery
Organic Chemistry
General Chemistry
Pharmacology

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title = "Total synthesis and in vitro-antifungal activity of (±)-2- methoxytetradecanoic acid",

abstract = "The marine fatty acid (±)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxytetradecanoate. 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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author = "Carballeira, {N{\'e}stor M.} and Denisse Ortiz and Keykavous Parang and Soroush Sardari",

year = "2004",

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doi = "10.1002/ardp.200300824",

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AU - Carballeira, Néstor M.

AU - Ortiz, Denisse

AU - Parang, Keykavous

AU - Sardari, Soroush

PY - 2004/3

Y1 - 2004/3

N2 - The marine fatty acid (±)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxytetradecanoate. 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.

AB - The marine fatty acid (±)-2-methoxytetradecanoic acid was synthesized in two steps (71% overall yield) starting from commercially available methyl-2-hydroxytetradecanoate. 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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KW - Antifungal activity

KW - Myristic acid

KW - N-Myristoyltransferase

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Total synthesis and in vitro-antifungal activity of (±)-2- methoxytetradecanoic acid

Abstract

Keywords

ASJC Scopus subject areas

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