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Int. J. Mol. Sci. 2012, 13(2), 1284-1299; doi:10.3390/ijms13021284
Article

Imidazolines as Non-Classical Bioisosteres of N-Acyl homoserine lactones and Quorum Sensing Inhibitors

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Received: 2 November 2011 / Revised: 6 January 2012 / Accepted: 10 January 2012 / Published: 25 January 2012
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Abstract

A series of selected 2-substituted imidazolines were synthesized in moderate to excellent yields by a modification of protocols reported in the literature. They were evaluated as potential non-classical bioisosteres of AHL with the aim of counteracting bacterial pathogenicity. Imidazolines 18a, 18e and 18f at various concentrations reduced the violacein production by Chromobacterium violaceum, suggesting an anti-quorum sensing profile against Gram-negative bacteria. Imidazoline 18b did not affect the production of violacein, but had a bacteriostatic effect at 100 µM and a bactericidal effect at 1 mM. Imidazoline 18a bearing a hexyl phenoxy moiety was the most active compound of the series, rendering a 72% inhibitory effect of quorum sensing at 100 µM. Imidazoline 18f bearing a phenyl nonamide substituent presented an inhibitory effect on quorum sensing at a very low concentration (1 nM), with a reduction percentage of 28%. This compound showed an irregular performance, decreasing inhibition at concentrations higher than 10 µM, until reaching 100 µM, at which concentration it increased the inhibitory effect with a 49% reduction percentage. When evaluated on Serratia marcescens, compound 18f inhibited the production of prodigiosin by 40% at 100 μM.
Keywords: imidazoline synthesis; quorum sensing; Chromobacterium violaceum; AHL bioisosteres imidazoline synthesis; quorum sensing; Chromobacterium violaceum; AHL bioisosteres
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.

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Reyes-Arellano, A.; Bucio-Cano, A.; Montenegro-Sustaita, M.; Curiel-Quesada, E.; Salgado-Zamora, H. Imidazolines as Non-Classical Bioisosteres of N-Acyl homoserine lactones and Quorum Sensing Inhibitors. Int. J. Mol. Sci. 2012, 13, 1284-1299.

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