Identification of unsaturated N-acylhomoserine lactones in bacterial isolates of Rhodobacter sphaeroides by liquid chromatography coupled to electrospray ionization-hybrid linear ion trap-Fourier transform ion cyclotron resonance mass spectrometry

Rapid Communications in Mass Spectrometry

Volumn 25, Issue 13, 2011, Pages 1817-1826

  Cataldi, Tommaso R I ^a   Bianco, Giuliana ^b   Abate, Salvatore ^b   Losito, Ilario ^a  

^a UNIVERSITY OF BARI   (Italy)

^b UNIVERSITY OF BASILICATA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CHAINS; CYCLOTRONS; ELECTRON CYCLOTRON RESONANCE; ESTERS; IONS; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; MATHEMATICAL TRANSFORMATIONS;

ACYL CHAIN; BACTERIAL ISOLATES; C-C BONDS; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETERS; FOURIER TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY; FOURIER-TRANSFORM ION CYCLOTRON RESONANCE MASS SPECTROMETRY; LINEAR ION TRAP; N-ACYLHOMOSERINE LACTONES; QUADRUPOLES; RHODOBACTER SPHAEROIDES;

ELECTROSPRAY IONIZATION;

EID: 79958105712     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.5054     Document Type: Article

References (43)

1. W. C. Fuqua, S. C. Winans, E. P. Greenberg,. Quorum sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulators. J. Bacteriol. 1994, 176, 269.
2. S. Swift, P. Williams, G. S. A. B. Stewart,. N-Acylhomoserine lactones and quorum sensing in proteobacteria, in Cell-Cell Signaling in Bacteria, (Eds:, G. M. Dunny, S. C. Winans,), ASM Press, Washington, DC, 1999, 5, 291.
3. C. Fuqua, M. R. Parsek, E. P. Greenberg,. Regulation of gene expression by cell-to-cell communication: acyl-homoserine lactone quorum sensing. Annu. Rev. Genet. 2001, 35, 439.
4. C. Fuqua, E. P. Greenberg,. Listening in on bacteria: acylhomoserine lactone signaling. Nature Rev. Mol. Cell Biol. 2002, 3, 685.
5. M. Cámara, P. Williams, A. Hardman,. Controlling infection by tuning in and turning down the volume of bacterial small-talk. Lancet Infect. Dis. 2002, 2, 667.
6. R. S. Blosser-Middleton, K. M. Gray,. Multiple N-acyl homoserine lactone signals of Rhizobium leguminosarum are synthesized in a distinct temporal pattern. J. Bacteriol. 2001, 183, 6771.
7. I. Wagner-Dobler, V. Thiel, L. Eberl, M. Allgaier, A. Bodor, S. Meyer, S. Ebner, A. Hennig, R. Pukall, S. Schulz,. Discovery of complex mixtures of novel long-chain quorum sensing signals in free-living and host-associated marine alphaproteobacteria. ChemBioChem 2005, 6, 2195.
8. V. Thiel, B. Kunze, P. Verma, I. Wagner-Dobler, S. Schulz,. New structural variants of homoserine lactones in bacteria. ChemBioChem 2009, 10, 1861.
9. J. S. Dickschat,. Quorum sensing and bacterial biofilms. Nat. Prod. Rep. 2010, 27, 343.
10. S. R. Chhabra, B. Philipp, L. Eberl, M. Givskov, P. Williams, M. Cámara,. Extracellular communication in bacteria, in The Chemistry of Pheromones and Other Semiochemicals II, (Ed., S. Schulz,), 2005, pp. 279-315.
11. K. H. McClean, M. K. Winson, L. Fish, A. Taylor, S. R. Chhabra, M. Càmara, M. Daykin, S. Swift, B. W. Bycroft, G. S. A. B. Stewart, P. Williams,. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acyl homoserine-lactones. Microbiology-SGM 1997, 143, 3703.
12. M. K. Winson, S. Swift, L. Fish, J. P. Throup, F. Jorgensen, S. R. Chhabra, B. W. Bycroft, P. Williams, G. S. A. B. Stewart,. Construction and analysis of lux CDABE-based plasmids sensors for investigating N-acyl homoserine lactone-mediated quorum sensing. FEMS Lett. 1998, 163, 185.
13. P. D. Shaw, G. Ping, S. L. Daly, C. Cha, J. E. Cronan Jr, K. L. Rinehaert, S. K. Farrand,. Detecting and characterizing N-acyl-homoserine lactone signal molecules by thin-layer chromatography. Proc. Natl. Acad. Sci. USA 1997, 94, 6036.
14. J. B. Andersen, A. Heydorn, M. Hentzer, L. Eberl, O. Geisenberger, B. B. Christensen, S. Molin, M. Givskov,. gfp-based N-acyl-homoserine lactone sensor systems for detection of bacterial communication. Appl. Environ. Microbiol. 2001, 67, 575.
15. A. Kumari, P. Pasini, S. K. Deo, D. Flomenhoft, H. Shashidhar, S. Daunert,. Biosensing systems for the detection of bacterial quorum signaling molecules. Anal. Chem. 2006, 78, 7603.
16. J. P. Pearson, K. M. Gray, L. Passador, K. D. Tucker, A. Eberhard, B. H. Iglewski, E. P. Greenberg,. Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes. Proc. Natl. Acad. Sci. USA 1994, 91, 197.
17. T. S. Charlton, R. de Nys, A. Netting, N. Kumar, M. Hentzer, M. Givskov, S. Kjelleberg,. A novel and sensitive method for the quantification of N-3-oxoacyl homoserine lactones using gas chromatography-mass spectrometry: application to a model bacterial biofilm. Environ. Microbiol. 2000, 2, 530.
18. T. R. I. Cataldi, G. Bianco, M. Frommberger, P. Schmitt-Kopplin,. Direct analysis of selected N-acyl-L-homoserine lactones by gas-chromatography/mass spectrometry. Rapid Commun. Mass Spectrom. 2004, 18, 1341.
19. T. R. I. Cataldi, G. Bianco, L. Palazzo, V. Quaranta,. Occurrence of N-acyl-L-homoserine lactones in extracts of some Gram-negative bacteria evaluated by gas chromatography-mass spectrometry. Anal. Biochem. 2007, 361, 226.
20. M. Frommberger, P. Schmitt-Kopplin, G. Ping, H. Frish, M. Schmid, Y. Zhang, A. Hartmann, A. Kettrup,. A simple and robust set-up for on-column sample preconcentration-nano-liquid chromatography-electrospray ionization mass spectrometry for the analysis of N-acylhomoserine lactones. Anal. Bioanal. Chem. 2004, 378, 1014.
21. X. Li, A. Fekete, M. Englmann, C. Götz, M. Rothballer, M. Frommberger, K. Buddrus, J. Fekete, C. Cai, P. Schröder, A. Hartmann, G. Chen, P. Schmitt-Kopplin,. Development and application of a method for the analysis of N-acylhomoserine lactones by solid-phase extraction and ultra high pressure liquid chromatography. J. Chromatogr. A 2006, 1134, 186.
22. C. A. Ortori, S. Atkinson, S. R. Chhabra, M. Cámara, P. Williams, D. A. Barrett,. Comprehensive profiling of N-acylhomoserine lactones produced by Yersinia pseudotuberculosis using liquid chromatography coupled to hybrid quadrupole-linear ion trap mass spectrometry. Anal. Bioanal. Chem. 2007, 387, 497.
23. D. Morin, B. Grasland, K. Vallee-Rehel, C. Dufau, D. Hara,. On-line high-performance liquid chromatography-mass spectrometric detection and quantification of N-acylhomoserine lactones, quorum sensing signal molecules, in the presence of biological matrices. J. Chromatogr. A 2003, 1002, 79.
24. A. Fekete, M. Frommberger, M. Rothballer, X. Li, M. Englmann, J. Fekete, A. Hartmann, L. Eberl, P. Schmitt-Kopplin,. Identification of bacterial N-acylhomoserine lactones (AHLs) with a combination of ultra-performance liquid chromatography (UPLC), ultra-high-resolution mass spectrometry, and in-situ biosensors. Anal. Bioanal. Chem. 2007, 387, 455.
25. J. J. Michels, E. J. Allain, S. A. Borchardt, P. Hu, W. F. McCoy,. Degradation pathway of homoserine lactone bacterial signal molecules by halogen antimicrobials identified by liquid chromatography with photodiode array and mass spectrometric detection. J. Chromatogr. A 2000, 898, 153.
26. T. A. Gould, J. Herman, J. Krank, R. C. Murphy, M. E. Churchill,. Specificity of acyl-homoserine lactone synthases examined by mass spectrometry. J. Bacteriol. 2006, 188, 773.
27. J. B. Bruhn, A. B. Christensen, L. R. Flodgaard, K. F. Nielsen, T. O. Larsen, M. Givskov, L. Gram,. Presence of acylated homoserine lactones (AHLs) and AHL-producing bacteria in meat and potential role of AHL in spoilage of meat. Appl. Environ. Microbiol. 2004, 70, 4293.
28. S. K. Farrand, Y. Qin, P. Oges,. Quorum-sensing system of Agrobacterium plasmids: analysis and utility. Methods Enzymol. 2002, 358, 452.
29. K. H. McClean, M. K. Winson, L. Fish,. Quorum sensing and Chromobacterium violaceum: exploitation of violacein production and inhibition for the detection of N-acylhomoserine lactones. Microbiology 1997, 143, 3703.
30. M. K. Winson, S. Swift, L. Fish, J. P. Throup, F. Jorgensen, S. R. Chhabra, B. W. Bycroft, P. Williams, G. S. Stewart,. Construction and analysis of luxCDABE-based plasmid sensors for investigating N-acylhomoserine lactone-mediated quorum sensing. FEMS Microbiol. Lett. 1998, 163, 185.
31. L. Steindler, V. Venturi,. Detection of quorum-sensing N-acyl homoserine lactone signal molecules by bacterial biosensors. FEMS Microbiol. Lett. 2007, 266, 1.
32. N. J. Bainton, P. Stead, S. R. Chhabra, B. W. Bycroft, G. P. C. Salmond, G. S. A. B. Stewart, P. Williams,. N-(3-Chetohexanoyl)-L-homoserine lactone regulates carbapenem antibiotic production in Erwinia carotovora. Biochem. J. 1992, 288, 997.
33. M. Frommberger, N. Hertkorn, M. Englmann, S. Jakoby, A. Hartmann, A. Kettrup, P. Schmitt-Kopplin,. Analysis of N-acylhomoserine lactones after alkaline hydrolysis and anion-exchange solid-phase extraction by capillary zone electrophoresis-mass spectrometry. Electrophoresis 2005, 26, 1523.
34. T. R. I. Cataldi, G. Bianco, S. Abate,. Profiling of N-acyl-homoserine lactones by liquid chromatography coupled with electrospray ionization and a hybrid quadrupole linear ion-trap and Fourier-transform ion-cyclotron-resonance mass spectrometry (LC-ESI-LTQ-FTICR-MS). J. Mass Spectrom. 2008, 43, 82.
35. T. R. I. Cataldi, G. Bianco, S. Abate,. Accurate mass analysis of N-acyl-homoserine-lactones and cognate lactone-opened compounds in bacterial isolates of Pseudomonas aeruginosa PAO1 by LC-ESI-LTQ-FTICR-MS. J. Mass Spectrom. 2009, 44, 182.
36. A. Puskas, E. P. Greenberg, S. Kaplan, A. L. Schaefer,. A quorum-sensing system in the free-living photosynthetic bacterium Rhodobacter sphaeroides. J. Bacteriol. 1997, 179, 7530.
37. J. Rodriguez, J. P. Dulcere,. Cohalogenation in organic synthesis. Synthesis 1993, 1177.
38. D. J. Porter, A. T. Stewart, C. T. Wigal,. Synthesis of a bromohydrin-an experiment demonstrating Markovnikov addition. J. Chem. Ed. 1995, 72, 1039.
39. A. Iida, Y. Ohnishi, S. Horinouchi,. Control of acetic acid fermentation by quorum sensing via N-acylhomoserine lactones in Gluconacetobacter intermedius. J. Bacteriol. 2008, 190, 2546.
40. A. E. M. Crotti, T. Fonseca, H. Hong, J. Staunton, S. E. Galembeck, N. P. Lopes, P. J. Gates,. The fragmentation mechanism of five-membered lactones by electrospray ionisation tandem mass spectrometry. Int. J. Mass Spectrom. 2004, 232, 271.
41. D. J. Harvey,. A new charge-associated mechanism to account for the production of fragment ions in the high-energy CID spectra of fatty acids. J. Am. Soc. Mass Spectrom. 2005, 16, 280.
42. C. H. Cheng, L. M. Gross,. Applications and mechanisms of charge remote fragmentation. Mass Spectrom. Rev. 2000, 19, 398.
43. F. F. Hsu, J. Turk, A. K. Thukkani, M. C. Messner, K. R. Wildsmith, D. A. Ford,. Characterization of alkylacyl, alk-1-enylacyl and lyso subclasses of glycerophosphocholine by tandem quadrupole mass spectrometry with electrospray ionization. J. Mass Spectrom. 2003, 38, 752.