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

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

Research output: Contribution to journalArticlepeer-review

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 languageEnglish (US)
Pages (from-to)152-155
Number of pages4
JournalArchiv der Pharmazie
Volume337
Issue number3
DOIs
StatePublished - Mar 2004
Externally publishedYes

Keywords

  • 2-Methoxytetradecanoic acid
  • Antifungal activity
  • Myristic acid
  • N-Myristoyltransferase

ASJC Scopus subject areas

  • Drug Discovery
  • Organic Chemistry
  • Chemistry(all)
  • Pharmacology

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