Imidazolines as Non-classical bioisosteres of N-Acyl homoserine lactones and quorum sensing inhibitors

Alicia Reyes-Arellano, Alejandro Bucio-Cano, Mabel Montenegro-Sustaita, Everardo Curiel-Quesada, Héctor Salgado-Zamora

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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. © 2012 by the authors; licensee MDPI, Basel, Switzerland.
Original languageAmerican English
Pages (from-to)1284-1299
Number of pages16
JournalInternational Journal of Molecular Sciences
StatePublished - 1 Feb 2012


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