2,6-Hexadecadiynoic acid and 2,6-nonadecadiynoic acid: Novel synthesized acetylenic fatty acids as potent antifungal agents

Néstor M. Carballeira, David Sanabria, Clarisa Cruz, Keykavous Parang, Baojie Wan, Scott Franzblau

Research output: Contribution to journalArticlepeer-review

Abstract

The hitherto unknown 2,6-hexadecadiynoic acid, 2,6-nonadecadiynoic acid, and 2,9-hexadecadiynoic acid were synthesized in two steps and in 11-18% overall yields starting from either 1,5-hexadiyne or 1,8-nonadiyne. Among all the compounds 2,6-hexadecadiynoic acid displayed the best overall antifungal activity against both the fluconazole-resistant Candida albicans strains ATCC 14053 and ATCC 60193, with a minimum inhibitory concentration (MIC of 11 μM), and against Cryptococcus neoformans ATCC 66031 (MIC <5.7 μM). 2,9-Hexadecadiynoic acid did not display any significant cytotoxicity against the fluconazole-resistant C. albicans strains, but it showed fungitoxicity against C. neoformans ATCC 66031 with a MIC value of <5.8 μM. Other FA, such as 2-hexadecynoic acid, 5-hexadecynoic acid, 9-hexadecynoic acid, and 6-nonadecynoic acid were also synthesized and their antifungal activities compared with those of the novel acetylenic FA. 2-Hexadecynoic acid, a known antifungal FA, exhibited the best antifungal activity (MIC = 9.4 μM) against the fluconazole-resistant C. albicans ATCC 14053 strain, but it showed a MIC value of only 100 μM against C. albicans ATCC 60193. 2,6-Hexadecadiynoic acid and 2-hexadecynoic acid also displayed a MIC of 140-145 μM toward Mycobacterium tuberculosis H37Rv in Middlebrook 7H12 medium. In conclusion, 2,6-hexadecadiynoic acid exhibited the best fungitoxicity profile compared with other analogues. This diynoic FA has the potential to be further evaluated for use in topical antifungal formulations.

Original languageEnglish (US)
Pages (from-to)507-511
Number of pages5
JournalLipids
Volume41
Issue number5
DOIs
StatePublished - May 2006
Externally publishedYes

ASJC Scopus subject areas

  • Medicine (miscellaneous)
  • Biochemistry, Genetics and Molecular Biology(all)
  • Food Science
  • Biochemistry

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