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. 2013 Mar 13;18(3):3266-78.
doi: 10.3390/molecules18033266.

Design, synthesis and biological evaluation of N-sulfonyl homoserine lactone derivatives as inhibitors of quorum sensing in Chromobacterium violaceum

Mingming Zhao  1 , Yingying Yu, Yuhui Hua, Fan Feng, Yigang Tong, Xiaohong Yang, Junhai Xiao, Hongrui Song
Affiliations

Design, synthesis and biological evaluation of N-sulfonyl homoserine lactone derivatives as inhibitors of quorum sensing in Chromobacterium violaceum

Mingming Zhao et al. Molecules. .

Abstract

A novel series of N-sulfonyl homoserine lactone derivatives 5a-l has been designed, synthesized and evaluated for quorum sensing inhibitory activities towards violacein production. Of the compounds synthesized, compound 5h was found to possess an excellent level of enantiopurity (99.2% e.e.). The results indicated that compounds bearing an ortho substituent on their phenyl ring exhibited excellent levels of inhibitory activity against violacein production. Compounds 5h and 5k in particular, with IC₅₀ values of 1.64 and 1.66 µM, respectively, were identified as promising lead compounds for further structural modification.

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Figures

Figure 1
Figure 1
Structures of C10-HSL, CL and target compounds 5a–l.
Scheme 1
Scheme 1
Synthesis of target compounds.
Figure 2
Figure 2
Antibacterial spot tests of compounds 5h,k.
Figure 3
Figure 3
Molecular model of CviR with C6-HSL and compound 5h bound to the active site.
See this image and copyright information in PMC

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References

    1. Geske G.D., O’Nell J.C., Miller D.M., Mattmann M.E., Blackwell H.E. Modulation of Bacterial Quorum Sensing with Synthetic Ligands: Systematic Evaluation of N-Acylated Homoserine Lactones in Multiple Species and New Insights into Their Mechanisms of Action. J. Am. Chem. Soc. 2007;129:13613–13625. - PMC - PubMed
    1. Yang L., Liu Y., Stemberg C., Molin S. Evaluation of Enoyl-Acyl Carrier Protein Reductase Inhibitors as Pseudomonas aeruginosa Quorum-Quenching Reagents. Molecules. 2010;15:780–792. doi: 10.3390/molecules15020780. - DOI - PMC - PubMed
    1. Amara N., Mashiach R., Amar D., Krief P., Spieser S.A.H., Bottomley M.J., Aharoni A., Meijler M.M. Covalent Inhibition of Bacterial Quorum Sensing. J. Am. Chem. Soc. 2009;131:10610–10619. doi: 10.1021/ja903292v. - DOI - PubMed
    1. Persson T., Hansen T.H., Rasmussen T.B., Skindersø M.E., Givskov M., Nielsen J. Rational design and synthesis of new quorum-sensing inhibitors derived from acylated homoserine lactones and natural products from garlic. Org. Biomol. Chem. 2005;3:253–262. - PubMed
    1. Kim C., Kim J., Park H.Y., Park H.J., Kim C.K., Yoon J., Lee J.H. Development of Inhibitors against TraR Quorum-Sensing System in Agrobacterium tumefaciens by Molecular Modeling of the Ligand-Receptor Interaction. Mol. Cells. 2009;28:447–453. doi: 10.1007/s10059-009-0144-6. - DOI - PubMed

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