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Antagonism of Quorum Sensing Phenotypes by Analogs of the Marine Bacterial Secondary Metabolite 3-Methyl-N-(2′-Phenylethyl)-Butyramide

Department of Chemistry, Salve Regina University, Newport, RI 02840, USA
Department of Biomedical and Pharmaceutical Sciences, College of Pharmacy, University of Rhode Island, Kingston, RI 02881, USA
Authors to whom correspondence should be addressed.
Mar. Drugs 2019, 17(7), 389;
Received: 7 June 2019 / Revised: 21 June 2019 / Accepted: 27 June 2019 / Published: 1 July 2019
PDF [974 KB, uploaded 1 July 2019]


Quorum sensing (QS) antagonists have been proposed as novel therapeutic agents to combat bacterial infections. We previously reported that the secondary metabolite 3-methyl-N-(2′-phenylethyl)-butyramide, produced by a marine bacterium identified as Halobacillus salinus, inhibits QS controlled phenotypes in multiple Gram-negative reporter strains. Here we report that N-phenethyl hexanamide, a structurally-related compound produced by the marine bacterium Vibrio neptunius, similarly demonstrates QS inhibitory properties. To more fully explore structure–activity relationships within this new class of QS inhibitors, a panel of twenty analogs was synthesized and biologically evaluated. Several compounds were identified with increased attenuation of QS-regulated phenotypes, most notably N-(4-fluorophenyl)-3-phenylpropanamide against the marine pathogen Vibrio harveyi (IC50 = 1.1 µM). These findings support the opportunity to further develop substituted phenethylamides as QS inhibitors. View Full-Text
Keywords: quorum sensing; Vibrio; phenethylamide quorum sensing; Vibrio; phenethylamide

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Meschwitz, S.M.; Teasdale, M.E.; Mozzer, A.; Martin, N.; Liu, J.; Forschner-Dancause, S.; Rowley, D.C. Antagonism of Quorum Sensing Phenotypes by Analogs of the Marine Bacterial Secondary Metabolite 3-Methyl-N-(2′-Phenylethyl)-Butyramide. Mar. Drugs 2019, 17, 389.

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