Crossref journal-article
American Society for Microbiology
Journal of Bacteriology (235)
Abstract

A series of structural analogs of the Pseudomonas aeruginosa autoinducer [PAI, N-3-oxo-dodecanoyl homoserine lactone] were obtained and tested for their ability to act as autoinducers in stimulating the expression of the gene for elastase (lasB) by measuring beta-galactosidase production from a lasB-lacZ gene fusion in the presence of the transcriptional activator LasR. The data suggest that the length of the acyl side chain of the autoinducer molecule is the most critical factor for activity. Replacement of the ring O by S in the homoserine lactone moiety can be tolerated. Tritium-labelled PAI ([3H]PAI) was synthesized and used to demonstrate the association of [3H]PAI with cells overexpressing LasR. The PAI analogs were also tested for their ability to compete with [3H]PAI for binding of LasR. Results from the competition assays suggest that once again the length of the acyl side chain appears to be crucial for antagonist activity. The presence of the 3-oxo moiety also plays a significant role in binding since analogs which lacked this moiety were much less effective in blocking binding of [3H]PAI. All analogs demonstrating competition with PAI in binding to LasR also exhibited the ability to activate lasB expression, suggesting that they are functional analogs of PAI.

Bibliography

Passador, L., Tucker, K. D., Guertin, K. R., Journet, M. P., Kende, A. S., & Iglewski, B. H. (1996). Functional analysis of the Pseudomonas aeruginosa autoinducer PAI. Journal of Bacteriology, 178(20), 5995–6000.

Authors 6
  1. L Passador (first)
  2. K D Tucker (additional)
  3. K R Guertin (additional)
  4. M P Journet (additional)
  5. A S Kende (additional)
  6. B H Iglewski (additional)
References 31 Referenced 144
  1. Adamson , D. W. 1943 . Anhydrides of basic amino-acids . J. Chem. Soc. 1943 : 39 - 40 . (10.1039/jr9430000039) / J. Chem. Soc. / Anhydrides of basic amino-acids by Adamson D. W. (1943)
  2. Chhabra , S. R. , P. Stead , N. J. Bainton , G. P. C. Salmond , G. S. A. B. Stewart , P. Williams , and B. W. Bycroft . 1993 . Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl) L-homoserine lactone . J. Antibiotics 46 : 441 - 454 . (10.7164/antibiotics.46.441) / J. Antibiotics / Autoregulation of carbapenem biosynthesis in Erwinia carotovora by analogues of N-(3-oxohexanoyl) L-homoserine lactone by Chhabra S. R. (1993)
  3. Eberhard , A. , C. A. Widrig , P. McBath , and J. B. Schineller . 1986 . Analogs of the autoinducer of bioluminescence in Vibrio fischeri . Arch. Microbiol. 146 : 35 - 40 . (10.1007/BF00690155) / Arch. Microbiol. / Analogs of the autoinducer of bioluminescence in Vibrio fischeri by Eberhard A. (1986)
  4. Fuqua , C. W. , S. C. Winans , and E. P. Greenberg . 1994 . Quorum-sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulation . J. Bacteriol. 176 : 269 - 275 . (10.1128/JB.176.2.269-275.1994) / J. Bacteriol. / Quorum-sensing in bacteria: the LuxR-LuxI family of cell density-responsive transcriptional regulation by Fuqua C. W. (1994)
  5. Gambello , M. J. , S. Kaye , and B. H. Iglewski . 1993 . LasR of Pseudomonas aeruginosa is a transcriptional activator of the alkaline protease gene (apr) and an enhancer of exotoxin A expression . Infect. Immun. 61 : 1180 - 1184 . (10.1128/IAI.61.4.1180-1184.1993) / Infect. Immun. / LasR of Pseudomonas aeruginosa is a transcriptional activator of the alkaline protease gene (apr) and an enhancer of exotoxin A expression by Gambello M. J. (1993)
  6. Gambello , M. J. , and B. H. Iglewski . 1991 . Cloning and characterization of the Pseudomonas aeruginosa lasR gene, a transcriptional activator of elastase expression . J. Bacteriol. 173 : 3000 - 3009 . (10.1128/JB.173.9.3000-3009.1991) / J. Bacteriol. / Cloning and characterization of the Pseudomonas aeruginosa lasR gene, a transcriptional activator of elastase expression by Gambello M. J. (1991)
  7. Gilson , L. , A. Kuo , and P. V. Dunlap . 1995 . ainS and a new family of autoinducer synthesis proteins . J. Bacteriol. 177 : 6946 - 6951 . (10.1128/JB.177.23.6946-6951.1995) / J. Bacteriol. / ainS and a new family of autoinducer synthesis proteins by Gilson L. (1995)
  8. Gray , K. M. , L. Passador , B. H. Iglewski , and E. P. Greenberg . 1994 . Interchangeability and specificity of components from the quorum-sensing regulatory systems of Vibrio fischeri and Pseudomonas aeruginosa . J. Bacteriol. 176 : 3076 - 3080 . (10.1128/JB.176.10.3076-3080.1994) / J. Bacteriol. / Interchangeability and specificity of components from the quorum-sensing regulatory systems of Vibrio fischeri and Pseudomonas aeruginosa by Gray K. M. (1994)
  9. Greenberg , E. P. , J. W. Hastings , and S. Ulitzur . 1979 . Induction of Iuciferase synthesis in Beneckea harveyi by other marine bacteria . Arch. Microbiol. 120 : 87 - 91 . (10.1007/BF00409093) / Arch. Microbiol. / Induction of Iuciferase synthesis in Beneckea harveyi by other marine bacteria by Greenberg E. P. (1979)
  10. Hanzelka , B. L. , and E. P. Greenberg . 1995 . Evidence that the N-terminal region of the Vibrio fischeri LuxR protein constitutes an autoinducer-binding domain . J. Bacteriol. 177 : 815 - 817 . (10.1128/jb.177.3.815-817.1995) / J. Bacteriol. / Evidence that the N-terminal region of the Vibrio fischeri LuxR protein constitutes an autoinducer-binding domain by Hanzelka B. L. (1995)
  11. Hwang , I. , P. L. Li , L. Zhang , K. R. Piper , D. M. Cook , M. E. Tate , and S. K. Farrand . 1994 . TraI, a LuxI homologue, is responsible for production of conjugation factor, the Ti plasmid N-acylhomoserine lactone autoinducer . Proc. Natl. Acad. Sci. USA 91 : 4639 - 4643 . (10.1073/pnas.91.11.4639) / Proc. Natl. Acad. Sci. USA / TraI, a LuxI homologue, is responsible for production of conjugation factor, the Ti plasmid N-acylhomoserine lactone autoinducer by Hwang I. (1994)
  12. Kaplan , H. B. , A. Eberhard , C. Widrig , and E. P. Greenberg . 1985 . Synthesis of N-[3-oxo-(4,5-3H2)-hexanoyl] homoserine lactone: biologically active tritium-labelled Vibrio fischeri autoinducer . J. Labelled Compd. Radiopharm. 22 : 387 - 395 . (10.1002/jlcr.2580220411) / J. Labelled Compd. Radiopharm. / Synthesis of N-[3-oxo-(4,5-3H2)-hexanoyl] homoserine lactone: biologically active tritium-labelled Vibrio fischeri autoinducer by Kaplan H. B. (1985)
  13. Kuo , A. , N. V. Blough , and P. V. Dunlap . 1994 . Multiple N-acyl-L-homoserine lactone autoinducers of Iuminescence in the marine symbiotic bacterium Vibrio fischeri . J. Bacteriol. 176 : 7558 - 7565 . (10.1128/JB.176.24.7558-7565.1994) / J. Bacteriol. / Multiple N-acyl-L-homoserine lactone autoinducers of Iuminescence in the marine symbiotic bacterium Vibrio fischeri by Kuo A. (1994)
  14. Linn , T. , and R. St. Pierre . 1990 . Improved vector system for constructing transcriptional fusions that ensures independent translation of lacZ . J. Bacteriol. 172 : 1077 - 1084 . (10.1128/JB.172.2.1077-1084.1990) / J. Bacteriol. / Improved vector system for constructing transcriptional fusions that ensures independent translation of lacZ by Linn T. (1990)
  15. Maniatis T. E. F. Fritsch and J. Sambrook. 1982. Molecular cloning: a laboratory manual. Cold Spring Harbor Laboratory Cold Spring Harbor N.Y.
  16. McKenney , D. , K. E. Brown , and D. G. Allison . 1995 . Influence of Pseudomonas aeruginosa exoproducts on virulence factor production in Burkholderia cepacia: evidence of interspecies communication . J. Bacteriol. 177 : 6989 - 6992 . (10.1128/JB.177.23.6989-6992.1995) / J. Bacteriol. / Influence of Pseudomonas aeruginosa exoproducts on virulence factor production in Burkholderia cepacia: evidence of interspecies communication by McKenney D. (1995)
  17. Ochsner , U. A. , A. K. Koch , A. Fiechter , and J. Reiser . 1994 . Isolation and characterization of a regulatory gene affecting rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa . J. Bacteriol. 176 : 2044 - 2054 . (10.1128/JB.176.7.2044-2054.1994) / J. Bacteriol. / Isolation and characterization of a regulatory gene affecting rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa by Ochsner U. A. (1994)
  18. Ochsner , U. A. , and J. Reiser . 1995 . Autoinducer-mediated regulation of rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa . Proc. Natl. Acad. Sci. USA 92 : 6424 - 6428 . (10.1073/pnas.92.14.6424) / Proc. Natl. Acad. Sci. USA / Autoinducer-mediated regulation of rhamnolipid biosurfactant synthesis in Pseudomonas aeruginosa by Ochsner U. A. (1995)
  19. Oikawa , Y. , K. Sugano , and O. Yonemitsu . 1978 . Meldrum's acid in organic synthesis. 2. A general and versatile synthesis ofketo esters . J. Org. Chem. 43 : 2087 - 2088 . (10.1021/jo00404a066) / J. Org. Chem. / Meldrum's acid in organic synthesis. 2. A general and versatile synthesis ofketo esters by Oikawa Y. (1978)
  20. Passador , L. , J. M. Cook , M. J. Gambello , L. Rust , and B. H. Iglewski . 1993 . Expression of Pseudomonas aeruginosa virulence genes requires cell to cell communication . Science 260 : 1127 - 1130 . (10.1126/science.8493556) / Science / Expression of Pseudomonas aeruginosa virulence genes requires cell to cell communication by Passador L. (1993)
  21. Passador , L. , and T. Linn . 1989 . Autogenous regulation of the RNA polymerasesubunit of Escherichia coli occurs at the translational level in vivo . J. Bacteriol. 171 : 6234 - 6242 . (10.1128/jb.171.11.6234-6242.1989) / J. Bacteriol. / Autogenous regulation of the RNA polymerasesubunit of Escherichia coli occurs at the translational level in vivo by Passador L. (1989)
  22. Pearson , J. P. , K. M. Gray , L. Passador , K. D. Tucker , A. Eberhard , B. H. Iglewski , and E. P. Greenberg . 1994 . Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes . Proc. Natl. Acad. Sci. USA 91 : 197 - 201 . (10.1073/pnas.91.1.197) / Proc. Natl. Acad. Sci. USA / Structure of the autoinducer required for expression of Pseudomonas aeruginosa virulence genes by Pearson J. P. (1994)
  23. Pearson J. P. and B. H. Iglewski. Unpublished data.
  24. Pearson , J. P. , L. Passador , B. H. Iglewski , and E. P. Greenberg . 1995 . A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa . Proc. Natl. Acad. Sci. USA 92 : 1490 - 1494 . (10.1073/pnas.92.5.1490) / Proc. Natl. Acad. Sci. USA / A second N-acylhomoserine lactone signal produced by Pseudomonas aeruginosa by Pearson J. P. (1995)
  25. Ralling , G. , Bodrug, S. , and T. G. Linn . 1985 . Growth rate dependent regulation of RNA polymerase synthesis in Escherichia coli . Mol. Gen. Genet. 201 : 379 - 386 . (10.1007/BF00331327) / Mol. Gen. Genet. / Growth rate dependent regulation of RNA polymerase synthesis in Escherichia coli by Ralling G. (1985)
  26. Schaefer , A. L. , B. L. Hanzelka , A. Eberhard , and E. P. Greenberg . 1996 . Quorum sensing in Vibrio fischeri: probing autoinducer-LuxR interactions with autoinducer analogs . J. Bacteriol. 178 : 2897 - 2901 . (10.1128/JB.178.10.2897-2901.1996) / J. Bacteriol. / Quorum sensing in Vibrio fischeri: probing autoinducer-LuxR interactions with autoinducer analogs by Schaefer A. L. (1996)
  27. Seed , P. C. , L. Passador , and B. H. Iglewski . 1995 . Activation of the Pseudomonas aeruginosa lasI gene by LasR and the Pseudomonas autoinducer PAI: an autoinduction regulatory hierarchy . J. Bacteriol. 177 : 654 - 659 . (10.1128/jb.177.3.654-659.1995) / J. Bacteriol. / Activation of the Pseudomonas aeruginosa lasI gene by LasR and the Pseudomonas autoinducer PAI: an autoinduction regulatory hierarchy by Seed P. C. (1995)
  28. Throup , J. P. , M. Camara , G. S. Briggs , M. K. Winson , S. R. Chhabra , B. W. Bycroft , P. Williams , and G. S. A. B. Stewart . 1995 . Characterisation of the yenI/yenR locus from Yersinia enterocolitica mediating the synthesis of two N-acyl homoserine lactone signal molecules . Mol. Microbiol. 17 : 345 - 356 . (10.1111/j.1365-2958.1995.mmi_17020345.x) / Mol. Microbiol. / Characterisation of the yenI/yenR locus from Yersinia enterocolitica mediating the synthesis of two N-acyl homoserine lactone signal molecules by Throup J. P. (1995)
  29. Toder , D. S. , M. J. Gambello , and B. H. Iglewski . 1991 . Pseudomonas aeruginosa LasA; a second elastase gene under transcriptional control of lasR . Mol. Microbiol. 5 : 2003 - 2010 . (10.1111/j.1365-2958.1991.tb00822.x) / Mol. Microbiol. / Pseudomonas aeruginosa LasA; a second elastase gene under transcriptional control of lasR by Toder D. S. (1991)
  30. Winson , M. K. , M. Camara , A. Latifi , M. Foglino , S. R. Chhabra , M. Daykin , M. Bally , V. Chapon , G. P. C. Salmond , B. W. Bycroft , A. Lazdunski , G. Stewart , and P. Williams . 1995 . Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa . Proc. Natl. Acad. Sci. USA 92 : 9427 - 9431 . (10.1073/pnas.92.20.9427) / Proc. Natl. Acad. Sci. USA / Multiple N-acyl-L-homoserine lactone signal molecules regulate production of virulence determinants and secondary metabolites in Pseudomonas aeruginosa by Winson M. K. (1995)
  31. Zhang , L. , P. J. Murphy , A. Kerr , and M. E. Tate . 1993 . Agrobacterium conjugation and gene regulation by N-acyl-L-homoserine lactones . Nature (London) 362 : 446 - 448 . (10.1038/362446a0) / Nature (London) / Agrobacterium conjugation and gene regulation by N-acyl-L-homoserine lactones by Zhang L. (1993)
Dates
Type When
Created 8 years, 9 months ago (Nov. 10, 2016, 8:27 a.m.)
Deposited 4 years, 1 month ago (July 29, 2021, 1:58 p.m.)
Indexed 1 year ago (Sept. 3, 2024, 10:19 a.m.)
Issued 28 years, 11 months ago (Oct. 1, 1996)
Published 28 years, 11 months ago (Oct. 1, 1996)
Published Print 28 years, 11 months ago (Oct. 1, 1996)
Funders 0

None

@article{Passador_1996, title={Functional analysis of the Pseudomonas aeruginosa autoinducer PAI}, volume={178}, ISSN={1098-5530}, url={http://dx.doi.org/10.1128/jb.178.20.5995-6000.1996}, DOI={10.1128/jb.178.20.5995-6000.1996}, number={20}, journal={Journal of Bacteriology}, publisher={American Society for Microbiology}, author={Passador, L and Tucker, K D and Guertin, K R and Journet, M P and Kende, A S and Iglewski, B H}, year={1996}, month=oct, pages={5995–6000} }