Chemistry & Biology
Quinolone Quorum Quenching
REFERENCES
Diggle, S.P., Lumjiaktase, P., Dipilato, F., Winzer, K., Kunakorn, M., Barrett,
D.A., Chhabra, S.R., C a´ mara, M., and Williams, P. (2006). Functional genetic
analysis reveals a 2-alkyl-4-quinolone signaling system in the human pathogen
Burkholderia pseudomallei and related bacteria. Chem. Biol. 13, 701–710.
Allesen-Holm, M., Barken, K.B., Yang, L., Klausen, M., Webb, J.S., Kjelleberg,
S., Molin, S., Givskov, M., and Tolker-Nielsen, T. (2006). A characterization of
DNA release in Pseudomonas aeruginosa cultures and biofilms. Mol. Micro-
biol. 59, 1114–1128.
Diggle, S.P., Matthijs, S., Wright, V.J., Fletcher, M.P., Chhabra, S.R., Lamont,
I.L., Kong, X., Hider, R.C., Cornelis, P., C a´ mara, M., and Williams, P. (2007).
The Pseudomonas aeruginosa 4-quinolone signal molecules HHQ and PQS
play multifunctional roles in quorum sensing and iron entrapment. Chem.
Biol. 14, 87–96.
Ball, G., Durand, E., Lazdunski, A., and Filloux, A. (2002). A novel type II secre-
tion system in Pseudomonas aeruginosa. Mol. Microbiol. 43, 475–485.
Beermann, B., Guddorf, J., Boehm, K., Albers, A., Kolkenbrock, S., Fetzner, S.,
and Hinz, H.-J. (2007). Stability, unfolding, and structural changes of cofactor-
free 1H-3-hydroxy-4-oxoquinaldine 2,4-dioxygenase. Biochemistry 46, 4241–
Dong, Y.-H., Wang, L.-H., and Zhang, L.-H. (2007). Quorum-quenching micro-
bial infections: mechanisms and implications. Philos. Trans. R. Soc. Lond.
B Biol. Sci. 362, 1201–1211.
4
249.
Boehm, K., Guddorf, J., Albers, A., Kamiyama, T., Fetzner, S., and Hinz, H.-J.
2008). Thermodynamic analysis of denaturant-induced unfolding of HodC69S
Eiden, F., Wendt, R., and Fenner, H. (1978). Chinolyliden-Derivate. Archiv der
(
Pharmazie (Weinheim, Germany) 311, 561–568.
protein supports a three-state mechanism. Biochemistry 47, 7116–7126.
Essar, D.W., Eberly, L., Hadero, A., and Crawford, I.P. (1990). Identification
and characterization of genes for a second anthranilate synthase in Pseudo-
monas aeruginosa: interchangeability of the two anthranilate synthases and
evolutionary implications. J. Bacteriol. 172, 884–900.
Bredenbruch, F., Nimtz, M., Wray, V., Morr, M., M u¨ ller, R., and H a¨ ussler, S.
(2005). Biosynthetic pathway of Pseudomonas aeruginosa 4-hydroxy-2-alkyl-
quinolines. J. Bacteriol. 187, 3630–3635.
Bredenbruch, F., Geffers, R., Nimtz, M., Buer, J., and H a¨ ussler, S. (2006). The
Pseudomonas aeruginosa quinolone signal (PQS) has an iron chelating
activity. Environ. Microbiol. 8, 1318–1329.
Farrow, J.M., 3rd, and Pesci, E.C. (2007). Two distinct pathways supply
anthranilate as a precursor of the Pseudomonas quinolone signal. J. Bacteriol.
189, 3425–3433.
Farrow, J.M., 3rd, Sund, Z.M., Ellison, M.L., Wade, D.S., Coleman, J.P., and
Pesci, E.C. (2008). PqsE functions independently of PqsR-Pseudomonas qui-
nolone signal and enhances the rhl quorum-sensing system. J. Bacteriol. 190,
Calfee, M.W., Shelton, J.G., McCubrey, J.A., and Pesci, E.C. (2005). Solubility
and bioactivity of the Pseudomonas quinolone signal are increased by a Pseu-
domonas aeruginosa-produced surfactant. Infect. Immun. 73, 878–882.
7
043–7051.
Cao, H., Krishnan, G., Goumnerov, B., Tsongalis, J., Tompkins, R., and
Rahme, L.G. (2001). A quorum sensing-associated virulence gene of Pseudo-
monas aeruginosa encodes a LysR-like transcription regulator with a unique
self-regulatory mechanism. Proc. Natl. Acad. Sci. USA 98, 14613–14618.
Fetzner, S. (2002). Oxygenases without requirement for cofactors or metal
ions. Appl. Microbiol. Biotechnol. 60, 243–257.
Fischer, F., K u¨ nne, S., and Fetzner, S. (1999). Bacterial 2,4-dioxygenases: new
members of the a/b hydrolase-fold superfamily of enzymes functionally related
to serine hydrolases. J. Bacteriol. 181, 5725–5733.
Coleman, J.P., Hudson, L.L., McKnight, S.L., Farrow, J.M., 3rd, Calfee, M.W.,
Lindsey, C.A., and Pesci, E.C. (2008). Pseudomonas aeruginosa PqsA is an
anthranilate-coenzyme A ligase. J. Bacteriol. 190, 1247–1255.
Fletcher, M.P., Diggle, S.P., Crusz, S., Chhabra, S.R., C a´ mara, M., and
Williams, P. (2007). A dual biosensor for 2-alkyl-4-quinolone quorum-sensing
signal molecules. Environ. Microbiol. 9, 2683–2693.
Collier, D.N., Anderson, L., McKnight, S.L., Noah, T.L., Knowles, M., Boucher,
R., Schwab, U., Gilligan, P., and Pesci, E.C. (2002). A bacterial cell to cell signal
in the lungs of cystic fibrosis patients. FEMS Microbiol. Lett. 215, 41–46.
Friedemann, T.E., and Haugen, G.E. (1943). Pyruvic acid. II. The determination
of keto acids in blood and urine. J. Biol. Chem. 147, 415–442.
Cornelis, P., Anjaiah, V., Koedam, N., Delfosse, P., Jacques, P., Thonart, P.,
and Neirinckx, L. (1992). Stability, frequency and multiplicity of transposon
insertions in the pyoverdine region in the chromosomes of different fluorescent
pseudomonads. J. Gen. Microbiol. 138, 1337–1343.
Frerichs-Deeken, U., Ranguelova, K., Kappl, R., H u¨ ttermann, J., and Fetzner,
S. (2004). Dioxygenases without requirement for cofactors, and their chemical
model reaction: compulsory order ternary complex mechanism of 1H-3-
hydroxy-4-oxoquinaldine 2,4-dioxygenase involving general base catalysis
by histidine 251 and single-electron oxidation of the substrate dianion.
Biochemistry 43, 14485–14499.
Cornforth, J.W., and James, A.T. (1956). Structure of a naturally occurring
antagonist of dihydrostreptomycin. Biochem. J. 63, 124–130.
Davidge, K.S., Sanguinetti, G., Yee, C.H., Cox, A.G., McLeod, C.W., Monk,
C.E., Mann, B.E., Motterlini, R., and Poole, R.K. (2009). Carbon monoxide-
releasing antibacterial molecules target respiration and global transcriptional
regulators. J. Biol. Chem. 284, 4516–4524.
Gallagher, L.A., McKnight, S.L., Kuznetsova, M.S., Pesci, E.C., and Manoil, C.
(
2002). Functions required for extracellular quinolone signaling by Pseudo-
monas aeruginosa. J. Bacteriol. 184, 6472–6480.
Guina, T., Purvine, S.O., Yi, E.C., Eng, J., Goodlett, D.R., Aebersold, R., and
Miller, S.I. (2003). Quantitative proteomic analysis indicates increased
synthesis of a quinolone by Pseudomonas aeruginosa isolates from cystic
fibrosis airways. Proc. Natl. Acad. Sci. USA 100, 2771–2776.
Desmard, M., Davidge, K.S., Bouvet, O., Morin, D., Roux, D., Foresti, R.,
Ricard, J.D., Denamur, E., Poole, R.K., Montravers, P., et al. (2009). A carbon
monoxide-releasing molecule (CORM-3) exerts bactericidal activity against
Pseudomonas aeruginosa and improves survival in an animal model of bacter-
aemia. FASEB J. 23, 1023–1031.
Ha
¨
ussler, S., and Becker, T. (2008). The pseudomonas quinolone signal (PQS)
balances life and death in Pseudomonas aeruginosa populations. PLoS
Pathog. 4, e1000166.
D e´ ziel, E., L e´ pine, F., Milot, S., He, J., Mindrinos, M.N., Tompkins, R.G., and
Rahme, L.G. (2004). Analysis of Pseudomonas aeruginosa 4-hydroxy-2-alkyl-
quinolines (HAQs) reveals a role for 4-hydroxy-2-heptylquinoline in cell-to-cell
communication. Proc. Natl. Acad. Sci. USA 101, 1339–1344.
Jensen, P.O., Bjarnsholt, T., Phipps, R., Rasmussen, T.B., Calum, H., Christof-
fersen, L., Moser, C., Williams, P., Pressler, T., Givskov, M., and Hoiby, N.
(
2007). Rapid necrotic killing of polymorphonuclear leukocytes is caused by
D e´ ziel, E., Gopalan, S., Tampakaki, A.P., L e´ pine, F., Padfield, K.E., Saucier,
M., Xiao, G., and Rahme, L.G. (2005). The contribution of MvfR to Pseudo-
monas 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.
quorum-sensing-controlled production of rhamnolipid by Pseudomonas aeru-
ginosa. Microbiology 153, 1329–1338.
Kaniga, K., Delor, I., and Cornelis, R.G. (1991). A wide host range suicide
vector for improving reverse genetics in Gram-negative bacteria: inactivation
of the blaA gene of Yersinia enterocolitica. Gene 109, 137–141.
55, 998–1014.
Kaufmann, G.F., Park, J., and Janda, K.D. (2008). Bacterial quorum sensing:
Diggle, S.P., Winzer, K., Chhabra, S.R., Worrall, K.E., C a´ mara, M., and Wil-
liams, P. (2003). 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, 29–43.
a new target for anti-infective immunotherapy. Expert Opin. Biol. Ther. 8,
7
19–724.
Klendshoj, N.C., Feldstein, M., and Sprague, A.L. (1950). The spectrophoto-
metric determination of carbon monoxide. J. Biol. Chem. 183, 297–303.
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