ArticleBioorganic & medicinal chemistry2011
Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing.
Article in Bioorganic & medicinal chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 7 papers.
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Who cites it
7 citing papers in PubMed, 19 citations in OpenAlex.
- Complex Analysis of Vanillin and Syringic Acid as Natural Antimicrobial Agents againstInternational journal of molecular sciences · 2022Article
- Article
- Design, Synthesis and Biological Evaluation of Isoxazole-Based CK1 Inhibitors Modified with Chiral Pyrrolidine Scaffolds.Molecules (Basel, Switzerland) · 2019Article
- S-Ribosylhomocysteine analogs containing a [4-thio]ribose ring.Carbohydrate research · 2015Article
- Sodium houttuyfonate affects production of N-acyl homoserine lactone and quorum sensing-regulated genes expression in Pseudomonas aeruginosa.Frontiers in microbiology · 2014Article
- Exploiting quorum sensing to confuse bacterial pathogens.Microbiology and molecular biology reviews : MMBR · 2013Review
- Inhibition of LuxS by S-ribosylhomocysteine analogues containing a [4-aza]ribose ring.Bioorganic & medicinal chemistry · 2011Article
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Authors and funding
8 authors at 1 institution in 1 country.
Funding
Abstract
Quorum sensing (QS) is a population-dependent signaling process bacteria use to control multiple processes including virulence that is critical for establishing infection. The most common QS signaling molecule used by Gram-negative bacteria are acylhomoserine lactones. The development of non-native acylhomoserine lactone (AHL) ligands has emerged as a promising new strategy to inhibit QS in Gram-negative bacteria. In this work, we have synthesized a set of optically pure γ-lactams and their reduced cyclic azahemiacetal analogues, bearing the additional alkylthiomethyl substituent, and evaluated their effect on the AHL-dependent Pseudomonas aeruginosa las and rhl QS pathways. The concentration of these ligands and the simple structural modification such as the length of the alkylthio substituent has notable effect on activity. The γ-lactam derivatives with nonylthio or dodecylthio chains acted as inhibitors of las signaling with moderate potency. The cyclic azahemiacetal with shorter propylthio or hexylthio substituent was found to strongly inhibit both las and rhl signaling at higher concentrations while the propylthio analogue strongly stimulated the las QS system at lower concentrations.
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