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  • Title: Dual inhibition of mycobacterial fatty acid biosynthesis and degradation by 2-alkynoic acids.
    Author: Morbidoni HR, Vilchèze C, Kremer L, Bittman R, Sacchettini JC, Jacobs WR.
    Journal: Chem Biol; 2006 Mar; 13(3):297-307. PubMed ID: 16638535.
    Abstract:
    2-Hexadecynoic acid and 2-octadecynoic acid have cidal activity against Mycobacterium smegmatis and Mycobacterium bovis BCG. At subinhibitory concentrations, M. smegmatis rapidly transformed [1-(14)C]-2-hexadecynoic acid into endogenous fatty acids and elongated them into mycolic acids. Toxic concentrations of 2-hexadecynoic acid resulted in accumulation of 3-ketohexadecanoic acid, which blocked fatty acid biosynthesis, and 3-hexadecynoic acid, an inhibitor of fatty acid degradation. The combination of these two metabolites is necessary to achieve the inhibition of M. smegmatis. We conclude that 2- and 3-hexa/octadecynoic acids inhibit mycolic acid biosynthesis, fatty acid biosynthesis, and fatty acid degradation, pathways of significant importance for mycobacteria.
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