Antifungal properties of n-alkoxyacetic acids and their methyl esters

Gershon, H.; Shanks, L.; Deangelis, A.

Journal of Pharmaceutical Sciences 68(1): 82-84


ISSN/ISBN: 0022-3549
PMID: 758471
DOI: 10.1002/jps.2600680125
Accession: 004757506

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Eleven n-alkoxyacetic acids and their methyl esters, in which the alkyl group was C1-C9, C11 or C13, were tested against Aspergillus niger, Trichoderma viride and Myrothecium verrucaria in Sabouraud dextrose agar at pH 4.0-5.6. Toxicity to Candida albicans, Trichophyton mentagrophytes and Mucor mucedo was determined in the same medium at pH 5.6 and 7.0 in the absence and presence of 10% beef serum. The fungitoxicity of the acids was influenced by chain length, pH of the medium and absence or presence of adsorbents. The toxicity of the esters was influenced primarily by chain length and to a lesser extent by the medium pH and the presence of beef serum. The order of activity of the n-alkoxyacetic acids was according to the number of linear atoms in the chain: 11 > 12 > 10 > 9 > 8 > 7 > 6 > 14 > 16. T. mentagrophytes was the organism most strongly affected by these compounds, with the esters being slightly more active than the acids. Compared to other fatty acid analogs, the order of fungitoxicity, on a weight basis, was 2-alkynoic acids > 2-alkenoic acids > alkanoic acids > 2-bromoalkanoic acids > 2-fluoroalkanoic acids > n-alkoxyacetic acids.

Antifungal properties of n-alkoxyacetic acids and their methyl esters