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Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

Michail Syrpas (UGent) , Ewout Ruysbergh (UGent) , Christian Stevens (UGent) , Norbert De Kimpe (UGent) and Sven Mangelinckx (UGent)
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Organization
Abstract
Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-position of the carbonyl function of the N-acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N-acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure–activity studies.
Keywords
N-α-haloacylated homoserine lactones, HALOGENATED FATTY-ACIDS, quorum sensing, N-acylated homoserine lactones, halogenation, halogenated fatty acids, GRAM-NEGATIVE BACTERIA, PSEUDOMONAS-AERUGINOSA, ANALOGS, COMMUNICATION, AUTOINDUCERS, DERIVATIVES, INHIBITION, RESISTANCE

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MLA
Syrpas, Michail, Ewout Ruysbergh, Christian Stevens, et al. “Synthesis and Biological Evaluation of Novel N-α-haloacylated Homoserine Lactones as Quorum Sensing Modulators.” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY 10 (2014): 2539–2549. Print.
APA
Syrpas, M., Ruysbergh, E., Stevens, C., De Kimpe, N., & Mangelinckx, S. (2014). Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 10, 2539–2549.
Chicago author-date
Syrpas, Michail, Ewout Ruysbergh, Christian Stevens, Norbert De Kimpe, and Sven Mangelinckx. 2014. “Synthesis and Biological Evaluation of Novel N-α-haloacylated Homoserine Lactones as Quorum Sensing Modulators.” Beilstein Journal of Organic Chemistry 10: 2539–2549.
Chicago author-date (all authors)
Syrpas, Michail, Ewout Ruysbergh, Christian Stevens, Norbert De Kimpe, and Sven Mangelinckx. 2014. “Synthesis and Biological Evaluation of Novel N-α-haloacylated Homoserine Lactones as Quorum Sensing Modulators.” Beilstein Journal of Organic Chemistry 10: 2539–2549.
Vancouver
1.
Syrpas M, Ruysbergh E, Stevens C, De Kimpe N, Mangelinckx S. Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators. BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY. 2014;10:2539–49.
IEEE
[1]
M. Syrpas, E. Ruysbergh, C. Stevens, N. De Kimpe, and S. Mangelinckx, “Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators,” BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, vol. 10, pp. 2539–2549, 2014.
@article{5745522,
  abstract     = {Novel N-α-haloacylated homoserine lactones, in which a halogen atom was introduced at the α-position of the carbonyl function of the N-acyl chain, have been studied as quorum sensing (QS) modulators and compared with a library of natural N-acylated homoserine lactones (AHLs). The series of novel analogues consists of α-chloro, α-bromo and α-iodo AHL analogues. Furthermore, the biological QS activity of the synthetic AHL analogues compared to the natural AHLs was evaluated. Halogenated analogues demonstrated a reduced activity in the Escherichia coli JB523 bioassay, with the α-iodo lactones being the less active ones and the α-chloro AHLs the most potent QS agonists. Most of the α-haloacylated analogues did not exhibit a significant reduction when tested in the QS inhibition test. Therefore, these novel analogues could be utilized as chemical probes for QS structure–activity studies.},
  author       = {Syrpas, Michail and Ruysbergh, Ewout and Stevens, Christian and De Kimpe, Norbert and Mangelinckx, Sven},
  issn         = {1860-5397},
  journal      = {BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY},
  keywords     = {N-α-haloacylated homoserine lactones,HALOGENATED FATTY-ACIDS,quorum sensing,N-acylated homoserine lactones,halogenation,halogenated fatty acids,GRAM-NEGATIVE BACTERIA,PSEUDOMONAS-AERUGINOSA,ANALOGS,COMMUNICATION,AUTOINDUCERS,DERIVATIVES,INHIBITION,RESISTANCE},
  language     = {eng},
  pages        = {2539--2549},
  title        = {Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators},
  url          = {http://dx.doi.org/10.3762/bjoc.10.265},
  volume       = {10},
  year         = {2014},
}

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