Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug-Resistant Staphylococcus aureus.

Autor: Sanabria-Ríos DJ; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Morales-Guzmán C; Department of Chemistry, University of Puerto Rico, Río Piedras Campus, 17 Ave Universidad STE 1701, San Juan, PR, 00925, USA., Mooney J; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Medina S; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Pereles-De-León T; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Rivera-Román A; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Ocasio-Malavé C; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Díaz D; Faculty of Science and Technology, Inter American University of Puerto Rico, Metropolitan Campus, PO Box 191293, San Juan, PR, 00919, USA., Chorna N; Department of Biochemistry, University of Puerto Rico, Medical Sciences, Campus, PO Box 365067, San Juan, PR, 00936, USA., Carballeira NM; Department of Chemistry, University of Puerto Rico, Río Piedras Campus, 17 Ave Universidad STE 1701, San Juan, PR, 00925, USA.
Jazyk: angličtina
Zdroj: Lipids [Lipids] 2020 Mar; Vol. 55 (2), pp. 101-116. Date of Electronic Publication: 2020 Jan 24.
DOI: 10.1002/lipd.12213
Abstrakt: In the present study, the structural characteristics that impart antibacterial activity to C 16 alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C-3, C-6, C-8, C-9, C-10, and C-12 were carried out in four steps and with an overall yield of 34-78%. In addition, HDA analogs containing a sulfur atom at either C-4 or C-5 were also prepared in 69-77% overall yields, respectively. Results from this study revealed that the triple bond at C-2 is pivotal for the antibacterial activity displayed by 2-HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram-positive bacteria, including clinical isolates of methicillin-resistant Staphylococcus aureus (CIMRSA) strains. The potential of 2-HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2-HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2-HDA. Moreover, it was proved that the inhibition of S. aureus DNA gyrase can be linked to the antibacterial activity displayed by 2-HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram-positive bacteria, since critical micellar concentrations (CMC) between 50 and 300 μg/mL were obtained.
(© 2020 AOCS.)
Databáze: MEDLINE
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