{"doi":"10.1002/lipd.12213","title":"Antibacterial Activity of Hexadecynoic Acid Isomers toward Clinical Isolates of Multidrug‐Resistant <scp><i>Staphylococcus aureus</i></scp>","abstract":"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.","journal":"Lipids","year":2020,"id":102910,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":25,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9487,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2020-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":502445,"name":"Christian Morales‐Guzmán","orcid":null,"position":1,"is_corresponding":false},{"id":502446,"name":"Joseph Mooney","orcid":null,"position":2,"is_corresponding":false},{"id":502447,"name":"Solymar Medina","orcid":null,"position":3,"is_corresponding":false},{"id":502448,"name":"Tomás Pereles‐De‐León","orcid":null,"position":4,"is_corresponding":false},{"id":502449,"name":"Ashley Rivera‐Román","orcid":null,"position":5,"is_corresponding":false},{"id":502450,"name":"Carlimar Ocasio‐Malavé","orcid":null,"position":6,"is_corresponding":false},{"id":502451,"name":"Damarith Díaz","orcid":null,"position":7,"is_corresponding":false},{"id":453676,"name":"Nataliya Chorna","orcid":"0000-0002-7761-6802","position":8,"is_corresponding":false},{"id":501700,"name":"Néstor M. Carballeira","orcid":"0000-0001-7404-0505","position":9,"is_corresponding":false},{"id":501699,"name":"David J. Sanabria‐Ríos","orcid":"0000-0001-8797-1210","position":0,"is_corresponding":true}],"reference_count":42,"raw_metadata":null,"created_at":"2026-07-18T22:41:53.173268Z","pmid":"31975430","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}