title: Antibacterial activity of 2-alkynoic fatty acids against multidrug-resistant bacteria.
abstract: 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=15.6 μg/mL), Staphylococcus saprophyticus (MIC=15.5 μg/mL), and Bacillus cereus (MIC=31.3 μg/mL), as well as against the Gram-negative Klebsiella pneumoniae (7.8 μg/mL) and Pseudomonas aeruginosa (MIC=125 μg/mL). In addition, 2-HDA displayed significant antibacterial activity against methicillin-resistant S. aureus (MRSA) ATCC 43300 (MIC=15.6 μg/mL) and clinical isolates of MRSA (MIC=3.9 μg/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.
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States. Electronic address: dsanabria@intermetro.edu.
authors.forename: David J
authors.initials: DJ
authors.lastname: Sanabria-Ríos
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States.
authors.forename: Yaritza
authors.initials: Y
authors.lastname: Rivera-Torres
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States.
authors.forename: Gamalier
authors.initials: G
authors.lastname: Maldonado-Domínguez
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States.
authors.forename: Idializ
authors.initials: I
authors.lastname: Domínguez
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States.
authors.forename: Camille
authors.initials: C
authors.lastname: Ríos
authors.affiliation: Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR 00919, United States.
authors.forename: Damarith
authors.initials: D
authors.lastname: Díaz
authors.affiliation: Department of Microbiology and Immunology, Universidad Central del Caribe School of Medicine, PO Box 60327, Bayamón, PR 00960, United States.
authors.forename: José W
authors.initials: JW
authors.lastname: Rodríguez
authors.affiliation: Department of Microbiology and Immunology, Universidad Central del Caribe School of Medicine, PO Box 60327, Bayamón, PR 00960, United States.
authors.forename: Joanne S
authors.initials: JS
authors.lastname: Altieri-Rivera
authors.affiliation: Department of Microbiology and Immunology, Universidad Central del Caribe School of Medicine, PO Box 60327, Bayamón, PR 00960, United States.
authors.forename: Eddy
authors.initials: E
authors.lastname: Ríos-Olivares
authors.affiliation: Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR 00931-3346, United States.
authors.forename: Gabriel
authors.initials: G
authors.lastname: Cintrón
authors.affiliation: Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR 00931-3346, United States.
authors.forename: Nashbly
authors.initials: N
authors.lastname: Montano
authors.affiliation: Department of Chemistry, University of Puerto Rico, Rio Piedras Campus, PO Box 23346, San Juan, PR 00931-3346, United States.
authors.forename: Néstor M
authors.initials: NM
authors.lastname: Carballeira
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D005231:Fatty Acids, Unsaturated / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects*; D006094:Gram-Positive Bacteria / Q000187:drug effects*; D006801:Humans; D007963:Leukocytes, Mononuclear / Q000166:cytology / Q000187:drug effects; D055624:Methicillin-Resistant Staphylococcus aureus / Q000187:drug effects; D008826:Microbial Sensitivity Tests
chemical_list: D000900:Anti-Bacterial Agents; D005231:Fatty Acids, Unsaturated
keywords: 2-Alkynoic fatty acids; Antibacterial agents; MRSA; Micelles; Nosocomial infections; Synthesis