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. 2008 Nov 15;18(22):5978-81.
doi: 10.1016/j.bmcl.2008.07.089. Epub 2008 Jul 26.

Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators

Grant D Geske  1 , Margrith E Mattmann, Helen E Blackwell
Affiliations

Evaluation of a focused library of N-aryl L-homoserine lactones reveals a new set of potent quorum sensing modulators

Grant D Geske et al. Bioorg Med Chem Lett. .

Abstract

A focused library of N-aryl l-homoserine lactones was designed around known lactone leads and evaluated for antagonistic and agonistic activity against quorum-sensing receptors in Agrobacterium tumefaciens, Pseudomonas aeruginosa, and Vibrio fischeri. Several compounds were identified with significantly heightened activities relative to the lead compounds, and new structure-activity relationships (SARs) were delineated. Notably, 4-substituted N-phenoxyacetyl and 3-substituted N-phenylpropionyl l-homoserine lactones were identified as potent antagonists of TraR and LuxR, respectively.

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Figures

Figure 1
Figure 1
Generic structure for AHLs (top left), structures of selected naturally occurring AHLs (top right), and structures of our previously reported non-native AHLs (PHLs 1–5, POHL 6, and PPHL 7–8; bottom). Acyl chain carbon numbers are shown for clarity for native AHLs.
Figure 2
Figure 2
Structures of the acyl groups of the AHLs in Library E (E1–E39). All 39 AHLs have l-stereochemistry.
See this image and copyright information in PMC

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    2. Geske GD, O'Neill JC, Miller DM, Wezeman RJ, Mattmann ME, Lin Q, Blackwell HE. ChemBioChem. 2008;9:389. - PMC - PubMed

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