{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:48:38Z","timestamp":1786978118820,"version":"build-2736575974"},"reference-count":41,"publisher":"Wiley","issue":"2","license":[{"start":{"date-parts":[[2020,1,24]],"date-time":"2020-01-24T00:00:00Z","timestamp":1579824000000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000057","name":"National Institute of General Medical Sciences","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000057","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100000097","name":"National Center for Research Resources","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100000097","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["aocs.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Lipids"],"published-print":{"date-parts":[[2020,3]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    In the present study, the structural characteristics that impart antibacterial activity to C\n                    <jats:sub>16<\/jats:sub>\n                    alkynoic fatty acids (aFA) were further investigated. The syntheses of hexadecynoic acids (HDA) containing triple bonds at C\u20103, C\u20106, C\u20108, C\u20109, C\u201010, and C\u201012 were carried out in four steps and with an overall yield of 34\u201378%. In addition, HDA analogs containing a sulfur atom at either C\u20104 or C\u20105 were also prepared in 69\u201377% overall yields, respectively. Results from this study revealed that the triple bond at C\u20102 is pivotal for the antibacterial activity displayed by 2\u2010HDA, while the farther the position of the triple bond from the carbonyl group, the lower its bactericidal activity against gram\u2010positive bacteria, including clinical isolates of methicillin\u2010resistant\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>Staphylococcus aureus<\/jats:italic>\n                    <\/jats:styled-content>\n                    (CIMRSA) strains. The potential of 2\u2010HDA as an antibacterial agent was also assessed in five CIMRSA strains that were resistant to Ciprofloxacin (Cipro) demonstrating that 2\u2010HDA was the most effective treatment in inhibiting their growth when compared with either Cipro alone or equimolar combinations of Cipro and 2\u2010HDA. Moreover, it was proved that the inhibition of\n                    <jats:styled-content style=\"fixed-case\">\n                      <jats:italic>S. aureus<\/jats:italic>\n                    <\/jats:styled-content>\n                    DNA gyrase can be linked to the antibacterial activity displayed by 2\u2010HDA. Finally, it was determined that the ability of HDA analogs to form micelles can be linked to their decreased activity against gram\u2010positive bacteria, since critical micellar concentrations (CMC) between 50 and 300\u2009\u03bcg\/mL were obtained.\n                  <\/jats:p>","DOI":"10.1002\/lipd.12213","type":"journal-article","created":{"date-parts":[[2020,1,24]],"date-time":"2020-01-24T03:33:30Z","timestamp":1579836810000},"page":"101-116","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug\u2010Resistant\n                    <scp>\n                      <i>Staphylococcus aureus<\/i>\n                    <\/scp>"],"prefix":"10.1002","volume":"55","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-8797-1210","authenticated-orcid":false,"given":"David 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