Discovery of antagonists of PqsR, a key player in 2-alkyl-4-quinolone- dependent quorum sensing in Pseudomonas aeruginosa

Chemistry and Biology

Volumn 19, Issue 3, 2012, Pages 381-390

  Lu, Cenbin ^a   Kirsch, Benjamin ^a   Zimmer, Christina ^a   De Jong, Johannes C ^a   Henn, Claudia ^a   Maurer, Christine K ^a   Müsken, Mathias ^b   Häussler, Susanne ^b,c   Steinbach, Anke ^a   Hartmann, Rolf W ^a,d  

^a SAARLAND UNIVERSITY   (Germany)

^b INSTITUTE OF INFECTION IMMUNOLOGY   (Germany)

^c HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^d SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

PQSR ANTAGONIST; PYOCYANINE; QUINOLONE DERIVATIVE; RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; ESCHERICHIA COLI; IN VITRO STUDY; NONHUMAN; PATHOGENICITY; PSEUDOMONAS AERUGINOSA; QUORUM SENSING; REPORTER GENE; VIRULENCE;

4-QUINOLONES; BACTERIAL PROTEINS; DRUG DESIGN; GENES, REPORTER; KINETICS; PSEUDOMONAS AERUGINOSA; PYOCYANINE; QUORUM SENSING;

ESCHERICHIA COLI; PSEUDOMONAS AERUGINOSA;

EID: 84858987560     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chembiol.2012.01.015     Document Type: Article

References (49)

1. O. Arunlakshana, and H.O. Schild Some quantitative uses of drug antagonists Br. J. Pharmacol. 14 1959 48 58
2. T. Bjarnsholt, and M. Givskov Quorum-sensing blockade as a strategy for enhancing host defences against bacterial pathogens Philos. Trans. R. Soc. B Biol. Sci. 362 2007 1213 1222 (Pubitemid 47075152)
3. S.G. Bratsch Group electronegative method with Pauling units J. Chem. Educ. 62 1985 101 103
4. F. Bredenbruch, M. Nimtz, V. Wray, M. Morr, R. Müller, and S. Häussler Biosynthetic pathway of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines J. Bacteriol. 187 2005 3630 3635 (Pubitemid 40705564)
5. F. Bredenbruch, R. Geffers, M. Nimtz, J. Buer, and S. Häussler The Pseudomonas aeruginosa quinolone signal (PQS) has an iron-chelating activity Environ. Microbiol. 8 2006 1318 1329 (Pubitemid 44025327)
6. H. Cao, G. Krishnan, B. Goumnerov, J. Tsongalis, R. Tompkins, and L.G. Rahme A quorum sensing-associated virulence gene of Pseudomonas aeruginosa encodes a LysR-like transcription regulator with a unique self-regulatory mechanism Proc. Natl. Acad. Sci. USA 98 2001 14613 14618 (Pubitemid 33121440)
7. D.N. Collier, L. Anderson, S.L. McKnight, T.L. Noah, M. Knowles, R. Boucher, U. Schwab, P. Gilligan, and E.C. Pesci A bacterial cell to cell signal in the lungs of cystic fibrosis patients FEMS Microbiol. Lett. 215 2002 41 46 (Pubitemid 35232580)
8. J.W. Costerton, P.S. Stewart, and E.P. Greenberg Bacterial biofilms: a common cause of persistent infections Science 284 1999 1318 1322 (Pubitemid 29289651)
9. J.M. Courtney, J. Bradley, J. Mccaughan, T.M. O'Connor, C. Shortt, C.P. Bredin, I. Bradbury, and J.S. Elborn Predictors of mortality in adults with cystic fibrosis Pediatr. Pulmonol. 42 2007 525 532 (Pubitemid 46870384)
10. C. Cugini, M.W. Calfee, J.M. Farrow 3rd, D.K. Morales, E.C. Pesci, and D.A. Hogan Farnesol, a common sesquiterpene, inhibits PQS production in Pseudomonas aeruginosa Mol. Microbiol. 65 2007 896 906 (Pubitemid 47221077)
11. E. Déziel, F. Lépine, S. Milot, J.X. He, M.N. Mindrinos, R.G. Tompkins, and L.G. Rahme Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkylquinolines (HAQs) reveals a role for 4-hydroxy-2- heptylquinoline in cell-to-cell communication Proc. Natl. Acad. Sci. USA 101 2004 1339 1344 (Pubitemid 38182690)
12. E. Déziel, S. Gopalan, A.P. Tampakaki, F. Lépine, K.E. Padfield, M. Saucier, G. Xiao, and L.G. Rahme The contribution of MvfR to Pseudomonas aeruginosa pathogenesis and quorum sensing circuitry regulation: multiple quorum sensing-regulated genes are modulated without affecting lasRI, rhlRI or the production of N-acyl-L-homoserine lactones Mol. Microbiol. 55 2005 998 1014 (Pubitemid 40299172)
13. S.P. Diggle, P. Lumjiaktase, F. Dipilato, K. Winzer, M. Kunakorn, D.A. Barrett, S.R. Chhabra, M. Cámara, and P. Williams Functional genetic analysis reveals a 2-Alkyl-4-quinolone signaling system in the human pathogen Burkholderia pseudomallei and related bacteria Chem. Biol. 13 2006 701 710 (Pubitemid 44093287)
14. S.P. Diggle, K. Winzer, S.R. Chhabra, K.E. Worrall, M. Cámara, and P. Williams The Pseudomonas aeruginosa quinolone signal molecule overcomes the cell density-dependency of the quorum sensing hierarchy, regulates rhl-dependent genes at the onset of stationary phase and can be produced in the absence of LasR Mol. Microbiol. 50 2003 29 43 (Pubitemid 37222784)
15. S.P. Diggle, S. Matthijs, V.J. Wright, M.P. Fletcher, S.R. Chhabra, I.L. Lamont, X. Kong, R.C. Hider, P. Cornelis, M. Cámara, and P. Williams The Pseudomonas aeruginosa 4-quinolone signal molecules HHQ and PQS play multifunctional roles in quorum sensing and iron entrapment Chem. Biol. 14 2007 87 96 (Pubitemid 46138049)
16. J.M. Farrow 3rd, Z.M. Sund, M.L. Ellison, D.S. Wade, J.P. Coleman, and E.C. Pesci PqsE functions independently of PqsR-Pseudomonas quinolone signal and enhances the rhl quorum-sensing system J. Bacteriol. 190 2008 7043 7051
17. M.P. Fletcher, S.P. Diggle, S.A. Crusz, S.R. Chhabra, M. Cámara, and P. Williams A dual biosensor for 2-alkyl-4-quinolone quorum-sensing signal molecules Environ. Microbiol. 9 2007 2683 2693 (Pubitemid 47547537)
18. L.A. Gallagher, S.L. McKnight, M.S. Kuznetsova, E.C. Pesci, and C. Manoil Functions required for extracellular quinolone signaling by Pseudomonas aeruginosa J. Bacteriol. 184 2002 6472 6480 (Pubitemid 35332550)
19. M.J. Gambello, and B.H. Iglewski Cloning and characterization of the Pseudomonas aeruginosa lasR gene, a transcriptional activator of elastase expression J. Bacteriol. 173 1991 3000 3009
20. J.R. Govan, and V. Deretic Microbial pathogenesis in cystic fibrosis: mucoid Pseudomonas aeruginosa and Burkholderia cepacia Microbiol. Rev. 60 1996 539 574 (Pubitemid 26303478)
21. K.L. Griffith, and R.E. Wolf Jr. Measuring beta-galactosidase activity in bacteria: cell growth, permeabilization, and enzyme assays in 96-well arrays Biochem. Biophys. Res. Commun. 290 2002 397 402 (Pubitemid 34694512)
22. R.W. Hartmann, G. Kranzfelder, E. von Angerer, and H. Schönenberger Antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,1,2,2-tetraalkyl-1,2 -diphenylethanes J. Med. Chem. 23 1980 841 848 (Pubitemid 10091525)
23. S. Häussler, and T. Becker The pseudomonas quinolone signal (PQS) balances life and death in Pseudomonas aeruginosa populations PLoS Pathog. 4 2008 e1000166
24. S. Heeb, M.P. Fletcher, S.R. Chhabra, S.P. Diggle, P. Williams, and M. Cámara Quinolones: from antibiotics to autoinducers FEMS Microbiol. Rev. 35 2011 247 274
25. J. Hodgkinson, S.D. Bowden, W.R.J.D. Galloway, D.R. Spring, and M. Welch Structure-activity analysis of the Pseudomonas quinolone signal molecule J. Bacteriol. 192 2010 3833 3837
26. G. Jander, L.G. Rahme, and F.M. Ausubel Positive correlation between virulence of Pseudomonas aeruginosa mutants in mice and insects J. Bacteriol. 182 2000 3843 3845 (Pubitemid 30413039)
27. G. Klebe Von Agonisten zu Antagonisten Wirkstoffdesign Second Edition 2009 Spektrum Akademischer Verlag Heidelberg, Germany 118 119
28. T. Klein, C. Henn, C.J. de Jong, C. Zimmer, D. Pistorius, R. Müller, A. Steinbach, and R.W. Hartmann Identification of small-molecule antagonists of the Pseudomonas aeruginosa transcriptional regulator PqsR: biophysically guided hit discovery and optimization ACS Chem. Biol. 2011 in press
29. C. Koch, and N. Høiby Pathogenesis of cystic fibrosis Lancet 341 1993 1065 1069 (Pubitemid 23114408)
30. M.T. Konieczny, G. Maciejewski, and W. Konieczny Selectivity adjustment in the cleavage of allyl phenyl and methyl phenyl ethers with boron trifluoride-methyl sulfide complex Synthesis 10 2005 1575 1577 (Pubitemid 40992055)
31. M.G. Lamarche, and E. Déziel MexEF-OprN efflux pump exports the Pseudomonas quinolone signal (PQS) precursor HHQ (4-hydroxy-2-heptylquinoline) PLoS ONE 6 2011 e24310
32. S.E. Maddocks, and P.C. Oyston Structure and function of the LysR-type transcriptional regulator (LTTR) family proteins Microbiology 154 2008 3609 3623
33. S. Mahajan-Miklos, M.W. Tan, L.G. Rahme, and F.M. Ausubel Molecular mechanisms of bacterial virulence elucidated using a Pseudomonas aeruginosa-Caenorhabditis elegans pathogenesis model Cell 96 1999 47 56 (Pubitemid 29044152)
34. L. Mashburn-Warren, J. Howe, P. Garidel, W. Richter, F. Steiniger, M. Roessle, K. Brandenburg, and M. Whiteley Interaction of quorum signals with outer membrane lipids: insights into prokaryotic membrane vesicle formation Mol. Microbiol. 69 2008 491 502 (Pubitemid 351988019)
35. L. Mashburn-Warren, J. Howe, K. Brandenburg, and M. Whiteley Structural requirements of the Pseudomonas quinolone signal for membrane vesicle stimulation J. Bacteriol. 191 2009 3411 3414
36. D.V. Mavrodi, R.F. Bonsall, S.M. Delaney, M.J. Soule, G. Phillips, and L.S. Thomashow Functional analysis of genes for biosynthesis of pyocyanin and phenazine-1-carboxamide from Pseudomonas aeruginosa PAO1 J. Bacteriol. 183 2001 6454 6465 (Pubitemid 34059420)
37. S. McGrath, D.S. Wade, and E.C. Pesci Dueling quorum sensing systems in Pseudomonas aeruginosa control the production of the Pseudomonas quinolone signal (PQS) FEMS Microbiol. Lett. 230 2004 27 34 (Pubitemid 38091735)
38. U.A. Ochsner, and J. Reiser Autoinducer-mediated regulation of rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa Proc. Natl. Acad. Sci. USA 92 1995 6424 6428
39. U.A. Ochsner, A.K. Koch, A. Fiechter, and J. Reiser Isolation and characterization of a regulatory gene affecting rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa J. Bacteriol. 176 1994 2044 2054 (Pubitemid 24103555)
40. L. Passador, J.M. Cook, M.J. Gambello, L. Rust, and B.H. Iglewski Expression of Pseudomonas aeruginosa virulence genes requires cell-to-cell communication Science 260 1993 1127 1130 (Pubitemid 23186788)
41. E.C. Pesci, J.B.J. Milbank, J.P. Pearson, S. McKnight, A.S. Kende, E.P. Greenberg, and B.H. Iglewski Quinolone signaling in the cell-to-cell communication system of Pseudomonas aeruginosa Proc. Natl. Acad. Sci. USA 96 1999 11229 11234 (Pubitemid 29487363)
42. D. Pistorius, A. Ullrich, S. Lucas, R.W. Hartmann, U. Kazmaier, and R. Müller Biosynthesis of 2-Alkyl-4(1H)-quinolones in Pseudomonas aeruginosa: potential for therapeutic interference with pathogenicity ChemBioChem 12 2011 850 853
43. G. Rampioni, C. Pustelny, M.P. Fletcher, V.J. Wright, M. Bruce, K.P. Rumbaugh, S. Heeb, M. Cámara, and P. Williams Transcriptomic analysis reveals a global alkyl-quinolone-independent regulatory role for PqsE in facilitating the environmental adaptation of Pseudomonas aeruginosa to plant and animal hosts Environ. Microbiol. 12 2010 1659 1673
44. T.B. Rasmussen, and M. Givskov Quorum-sensing inhibitors as anti-pathogenic drugs Int. J. Med. Microbiol. 296 2006 149 161 (Pubitemid 43375998)
45. R.T. Sanderson Polar covalence 1983 Academic Press New York
46. J.W. Schertzer, S.A. Brown, and M. Whiteley Oxygen levels rapidly modulate Pseudomonas aeruginosa social behaviours via substrate limitation of PqsH Mol. Microbiol. 77 2010 1527 1538
47. S. Swift, J.A. Downie, N.A. Whitehead, A.M.L. Barnard, G.P.C. Salmond, and P. Williams Quorum sensing as a population-density-dependent determinant of bacterial physiology Adv. Microb. Physiol. 45 2001 199 270 (Pubitemid 32612193)
48. A. Woschek, M. Mahout, K. Mereiter, and F. Hammerschmidt Synthesis of 2-heptyl-1-hydroxy-4(1H)-quinolone unexpected rearrangement of 4-(alkoxycarbonyloxy)quinoline N-oxides to 1-(alkoxycarbonyloxy)-4(1H)- quinolones Synthesis 10 2007 1517 1522 (Pubitemid 46847962)
49. G. Xiao, E. Déziel, J. He, F. Lépine, B. Lesic, M.H. Castonguay, S. Milot, A.P. Tampakaki, S.E. Stachel, and L.G. Rahme MvfR, a key Pseudomonas aeruginosa pathogenicity LTTR-class regulatory protein, has dual ligands Mol. Microbiol. 62 2006 1689 1699 (Pubitemid 44813813)