Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria
2014
Sanabria-Ríos, David J. | Rivera-Torres, Yaritza | Maldonado-Domínguez, Gamalier | Domínguez, Idializ | Ríos, Camille | Díaz, Damarith | Rodríguez, José W. | Altieri-Rivera, Joanne S. | Ríos-Olivares, Eddy | Cintrón, Gabriel | Montano, Nashbly | Carballeira, Néstor M.
The first study aimed at determining the structural characteristics needed to prepare antibacterial 2-alkynoic fatty acids (2-AFAs) was accomplished by synthesizing several 2-AFAs and other analogs in 18–76% overall yields. Among all the compounds tested, the 2-hexadecynoic acid (2-HDA) displayed the best overall antibacterial activity against Gram-positive Staphylococcus aureus (MIC=15.6μg/mL), Staphylococcus saprophyticus (MIC=15.5μg/mL), and Bacillus cereus (MIC=31.3μg/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8μg/mL) and Pseudomonas aeruginosa (MIC=125μg/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC=15.6μg/mL) and clinical isolates of MRSA (MIC=3.9μg/mL). No direct relationship was found between the antibacterial activity of 2-AFAs and their critical micelle concentration (CMC) suggesting that the antibacterial properties of these fatty acids are not mediated by micelle formation. It was demonstrated that the presence of a triple bond at C-2 and the carboxylic acid moiety in 2-AFAs are important for their antibacterial activity. 2-HDA has the potential to be further evaluated for use in antibacterial formulations.
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