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Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity.

Publication ,  Journal Article
Frey, RL; He, L; Cui, Y; Decho, AW; Kawaguchi, T; Ferguson, PL; Ferry, JL
Published in: Environmental science & technology
October 2010

Chemical communication in bacteria, sometimes called quorum sensing, is a fundamental microbial process that is based on the exchange of molecular signals between cells. The signaling molecules involved in this process are thermodynamically unstable in some environments and their degradation affects microbial communication. This work reports the oxidation of a series of substituted N-acylhomoserine lactones (AHLs, a class of quorum sensing signals) by hydroxyl radicals. The corresponding bimolecular rate constants were obtained and correlated positively with the length of the acyl side chain (C, in numbers of carbon atoms) ranging from 2.4 × 10(9) M(-1) s(-1) to 9.4 × 10(9) M(-1) s(-1) (C4- to C10-AHL), 2.4 × 10(8) M(-1) s(-1) for 3-oxo C6-AHL, and 2.94 × 10(9) M(-1) s(-1) for 3-oxo C8-AHL. Liquid chromatography-mass spectrometric techniques were applied to qualify the identity and quantify the yields of the hydroxyl radical oxidation products of C6-AHL (aldo, keto, and hydroxylated C6-analogues identified). The biological activity of C6-AHL and associated products was determined using the Vibrio harveyi bioluminescence bioassay. Oxidation resulted in a net increase in assay response indexed against the starting AHL. This result suggested that the application of HO• based technologies such as advanced oxidation processes for biofilm control may result in unintended quorum sensing responses by microbial communities.

Duke Scholars

Published In

Environmental science & technology

DOI

EISSN

1520-5851

ISSN

0013-936X

Publication Date

October 2010

Volume

44

Issue

19

Start / End Page

7465 / 7469

Related Subject Headings

  • Vibrio
  • Spectrometry, Fluorescence
  • Quorum Sensing
  • Oxidation-Reduction
  • Mass Spectrometry
  • Luminescence
  • Kinetics
  • Hydroxyl Radical
  • Environmental Sciences
  • Chromatography, High Pressure Liquid
 

Citation

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Frey, R. L., He, L., Cui, Y., Decho, A. W., Kawaguchi, T., Ferguson, P. L., & Ferry, J. L. (2010). Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity. Environmental Science & Technology, 44(19), 7465–7469. https://doi.org/10.1021/es100663e
Frey, Rebecca L., Lijian He, Yiling Cui, Alan W. Decho, Tomohiro Kawaguchi, P Lee Ferguson, and John L. Ferry. “Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity.Environmental Science & Technology 44, no. 19 (October 2010): 7465–69. https://doi.org/10.1021/es100663e.
Frey RL, He L, Cui Y, Decho AW, Kawaguchi T, Ferguson PL, et al. Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity. Environmental science & technology. 2010 Oct;44(19):7465–9.
Frey, Rebecca L., et al. “Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity.Environmental Science & Technology, vol. 44, no. 19, Oct. 2010, pp. 7465–69. Epmc, doi:10.1021/es100663e.
Frey RL, He L, Cui Y, Decho AW, Kawaguchi T, Ferguson PL, Ferry JL. Reaction of N-acylhomoserine lactones with hydroxyl radicals: rates, products, and effects on signaling activity. Environmental science & technology. 2010 Oct;44(19):7465–7469.
Journal cover image

Published In

Environmental science & technology

DOI

EISSN

1520-5851

ISSN

0013-936X

Publication Date

October 2010

Volume

44

Issue

19

Start / End Page

7465 / 7469

Related Subject Headings

  • Vibrio
  • Spectrometry, Fluorescence
  • Quorum Sensing
  • Oxidation-Reduction
  • Mass Spectrometry
  • Luminescence
  • Kinetics
  • Hydroxyl Radical
  • Environmental Sciences
  • Chromatography, High Pressure Liquid