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Revisiting AI-2 quorum sensing inhibitors: Direct comparison of alkyl-DPD analogues and a natural product fimbrolide

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Overview

related to degree

  • Lowery, Colin, Ph.D. in Chemistry, Scripps Research 2004 - 2010

authors

  • Lowery, Colin
  • Abe, T.
  • Park, J.
  • Eubanks, L. M.
  • Sawada, D.
  • Kaufmann, Gunnar
  • Janda, Kim

publication date

  • November 2009

journal

  • Journal of the American Chemical Society  Journal

abstract

  • Quorum sensing (QS) systems have been discovered in a wide variety of bacteria, and mediate both intra- and interspecies communication. The AI-2-based QS system represents the most studied of these proposed interspecies systems and has been shown to regulate diverse functions such as bioluminescence, expression of virulence factors, and biofilm formation. As such, the development of modulatory compounds, both agonists and antagonists, is of great interest for the study of unknown AI-2-based QS systems and the potential treatment of bacterial infections. The fimbrolide class of natural products has exhibited excellent inhibitory activity against AI-2-based QS and as such may be considered the "gold standard" of AI-2 inhibitors. Thus, we sought to include a fimbrolide as a control compound for our recently developed alkyl-DPD panel of AI-2 modulators. Herein, we present a revised synthesis of a commonly studied fimbrolide as well as a direct comparison between the fimbrolide and alkyl-DPD analogues. We demonstrate that our alkyl-DPD analogues are more potent inhibitors of QS in both Vibrio harveyi and Salmonella typhimurium, the two organisms with defined AI-2 QS systems, and in doing so call into question the widely accepted use of fimbrolide-derived compounds as the "gold standard" of AI-2 inhibition.

subject areas

  • Biological Products
  • Furans
  • Quorum Sensing
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Identity

PubMed Central ID

  • PMC2784249

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja9066783

PubMed ID

  • 19824634
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Additional Document Info

start page

  • 15584

end page

  • 15585

volume

  • 131

issue

  • 43

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