Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection

Michels, James J.; Allain, E. J.; Borchardt, Scott A.; Hu, Peifeng; McCoy, William F.

doi:10.1016/s0021-9673(00)00849-9

Cited by 35 publications

(44 citation statements)

References 6 publications

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“…The ␣-carbon is rapidly dihalogenated and is subsequently hydrolyzed at the pH values tested. The ultimate products of the reaction are a dihalogenated acyl HSL and a carboxylic acid (27).…”

Section: Discussionmentioning

confidence: 99%

“…As previously stated, the acyl HSL molecule itself will break down slowly in solution, especially under alkaline conditions (as seen in the control). This was found to be due to hydrolysis of the lactone ring (27). However, the sample that contained both the brown algae and the H 2 O 2 demonstrated a significant increase in the degradation of the 3-oxo hexanoyl HSL as monitored by the C. violaceum CV026 bioassay.…”

Section: Effect Of Oxidized Halogen Antimicrobials On Acylated Hsl Acmentioning

confidence: 94%

“…A control was taken prior to addition of stabilized hypobromite, and the reaction was sampled at 5 min. Solutions were assayed for the halogenated acyl HSL reaction product by using a previously published high-performance liquid chromatography (HPLC) methodology (27). The liquid chromatograph consisted of a Waters (Milford, Mass.)…”

Section: Methodsmentioning

confidence: 99%

“…Figure 4 presents overlaid liquid chromatograms of a 0.05 mM 3-oxo-hexanoyl homoserine lactone prereaction control and the reaction with stabilized hypobromite in a P. aeruginosa biofilm medium buffered at pH 8.3. The chromatographic traces illustrate how the 3-oxo-HSL is completely converted to the dibrominated products DBEHL and hyd-DBEHL (27). Peaks eluting at or near the void volume of the chromatographic system at 2.5 min are biofilm components and antimicrobial.…”

Section: Effect Of Oxidized Halogen Antimicrobials On Acylated Hsl Acmentioning

confidence: 99%

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Reaction of Acylated Homoserine Lactone Bacterial Signaling Molecules with Oxidized Halogen Antimicrobials

Borchardt¹,

Allain²,

Michels³

et al. 2001

Appl Environ Microbiol

157

111

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Oxidized halogen antimicrobials, such as hypochlorous and hypobromous acids, have been used extensively for microbial control in industrial systems. Recent discoveries have shown that acylated homoserine lactone cell-to-cell signaling molecules are important for biofilm formation in Pseudomonas aeruginosa, suggesting that biofouling can be controlled by interfering with bacterial cell-to-cell communication. This study was conducted to investigate the potential for oxidized halogens to react with acylated homoserine lactone-based signaling molecules. Acylated homoserine lactones containing a 3-oxo group were found to rapidly react with oxidized halogens, while acylated homoserine lactones lacking the 3-oxo functionality did not react. The Chromobacterium violaceum CV026 bioassay was used to determine the effects of such reactions on acylated homoserine lactone activity. The results demonstrated that 3-oxo acyl homoserine lactone activity was rapidly lost upon exposure to oxidized halogens; however, acylated homoserine lactones lacking the 3-oxo group retained activity. Experiments with the marine alga Laminaria digitata demonstrated that natural haloperoxidase systems are capable of mediating the deactivation of acylated homoserine lactones. This may illustrate a natural defense mechanism to prevent biofouling on the surface of this marine alga. The Chromobacterium violaceum activity assay illustrates that reactions between 3-oxo acylated homoserine lactone molecules and oxidized halogens do occur despite the presence of biofilm components at much greater concentrations. This work suggests that oxidized halogens may control biofilm not only via a cidal mechanism, but also by possibly interfering with 3-oxo acylated homoserine lactone-based cell signaling.

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Section: Discussionmentioning

confidence: 99%

Section: Effect Of Oxidized Halogen Antimicrobials On Acylated Hsl Acmentioning

confidence: 94%

Section: Methodsmentioning

confidence: 99%

Section: Effect Of Oxidized Halogen Antimicrobials On Acylated Hsl Acmentioning

confidence: 99%

See 2 more Smart Citations

Reaction of Acylated Homoserine Lactone Bacterial Signaling Molecules with Oxidized Halogen Antimicrobials

Borchardt¹,

Allain²,

Michels³

et al. 2001

Appl Environ Microbiol

157

111

View full text Add to dashboard Cite

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“…Beneath other limitations (for discussion see [25]), especially the last step in classical AHL analysis is time-consuming and nonquantitative. Except for an approach with GC-MS [26], little profound data is present on systematic analysis of AHLs with modern chromatographic or electrophoretic techniques, presumably because the AHL molecules show a UV-absorbance maximum at or below 200 nm [27], which makes detection with UV difficult or requires large sample concentrations. MS detection, as a strictly concentration-dependent detection technique, overcomes this limitation, and, especially when run in selective fragmentation modes (MS/ MS, MS n ), provides structural information unmatched by other detection techniques.…”

Section: Introductionmentioning

confidence: 99%

Analysis of N‐acyl‐L‐homoserine lactones produced by Burkholderia cepacia with partial filling micellar electrokinetic chromatography – electrospray ionization‐ion trap mass spectrometry

Frommberger¹,

Schmitt‐Kopplin²,

Menzinger³

et al. 2003

Electrophoresis

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A method for the analysis of N-acyl-L-homoserine lactones (AHLs) with micellar electrokinetic chromatography coupled to electrospray ionization-ion trap mass spectrometry, combining the flexibility of capillary electrophoresis with the unmatched structural information provided by mass spectrometry is presented. Different surfactants were evaluated, with sodium dodecyl sulfate (SDS) yielding the best results considering sensitivity and flexibility. We examined the interaction of AHLs with the SDS micelles at different analysis conditions and applied the optimized method to the analysis of a real bacterial sample. Two AHLs from Burkholderia cepacia colonizing the rhizosphere of traditional Indian rice cultivars could be unambiguously determined in an ethyl acetate extract with high resolution flexibility.

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Identification of Bacterial Autoinducers – Methods Chapter

Fekete

Rothballer

Hartmann

et al. 2009

Bacterial Signaling

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Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection

Cited by 35 publications

References 6 publications

Reaction of Acylated Homoserine Lactone Bacterial Signaling Molecules with Oxidized Halogen Antimicrobials

Reaction of Acylated Homoserine Lactone Bacterial Signaling Molecules with Oxidized Halogen Antimicrobials

Analysis of N‐acyl‐L‐homoserine lactones produced by Burkholderia cepacia with partial filling micellar electrokinetic chromatography – electrospray ionization‐ion trap mass spectrometry

Identification of Bacterial Autoinducers – Methods Chapter

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