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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

1,* , 1
,
1
,
2
 and
1
1 Department of Organic Chemistry, National Polytechnic Institute, National School of Biological Sciences, Carpio y Plan de Ayala S/N, Colonia Santo Tomás, 11340 México, D.F., Mexico 2 Department of Biochemistry, National Polytechnic Institute, National School of Biological Sciences, Carpio y Plan de Ayala S/N, Colonia Santo Tomás, 11340 México, D.F., Mexico
* Author to whom correspondence should be addressed.
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 (CC BY 3.0).

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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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