Altering the communication networks of multispecies microbial systems using a diverse toolbox of AI-2 analogues

ACS Chemical Biology

Volumn 7, Issue 6, 2012, Pages 1023-1030

  Gamby, Sonja ^a   Roy, Varnika ^b,c   Guo, Min ^a   Smith, Jacqueline A I ^a   Wang, Jingxin ^a   Stewart, Jessica E ^c   Wang, Xiao ^b   Bentley, William E ^b,c   Sintim, Herman O ^a  

^a Bldg 142   (United States)

^b UNIVERSITY OF MARYLAND   (United States)

^c UNIVERSITY OF MARYLAND   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; BETA GALACTOSIDASE; BINDING PROTEIN; N ACYLHOMOSERINE LACTONE;

ARTICLE; BACTERIAL STRAIN; BACTERIUM; BACTERIUM IDENTIFICATION; CHEMICAL STRUCTURE; ECOSYSTEM; ESCHERICHIA COLI; GENE EXPRESSION; PRIORITY JOURNAL; PROTEIN PHOSPHORYLATION; PSEUDOMONAS AERUGINOSA; QUORUM SENSING; SALMONELLA TYPHIMURIUM; SYNTHESIS;

BETA-GALACTOSIDASE; ESCHERICHIA COLI; ESCHERICHIA COLI PROTEINS; HOMOSERINE; LACTONES; PHOSPHOTRANSFERASES (ALCOHOL GROUP ACCEPTOR); PSEUDOMONAS AERUGINOSA; QUORUM SENSING; REPRESSOR PROTEINS; SALMONELLA TYPHIMURIUM; SIGNAL TRANSDUCTION;

EID: 84862575444     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb200524y     Document Type: Article

References (43)

1. Waters, C. M. and Bassler, B. L. (2005) Quorum sensing: cell-to-cell communication in bacteria Annu. Rev. Cell Dev. Biol. 21, 319-346 (Pubitemid 41740638)
2. Bassler, B. L. and Losick, R. (2006) Bacterially speaking Cell 125, 237-246
3. Keller, L. and Surette, M. G. (2006) Communication in bacteria: an ecological and evolutionary perspective Nat. Rev. Microbiol. 4, 249-258
4. Lowery, C. A., Abe, T., Park, J., Eubanks, L. M., Sawada, D., Kaufmann, G. F., and Janda, K. D. (2009) Revisiting AI-2 quorum sensing inhibitors: direct comparison of alkyl-DPD analogues and a natural product fimbrolide J. Am. Chem. Soc. 131, 15584-15585
5. Jakobsen, T. H., Bragason, S. K., Phipps, R. K., Christensen, L. D., van Gennip, M., Alhede, M., Skindersoe, M., Larsen, T. O., Høiby, N., Bjarnsholt, T., and Givskov, M. (2012) Food as a source for quorum sensing inhibitors: iberin from horseradish revealed as a quorum sensing inhibitor of Pseudomonas aeruginosa. Appl. Environ. Microbiol. 78, 2410-2421
6. Glansdorp, F. G., Thomas, G. L., Lee, J. K., Dutton, J. M., Salmond, G. P., Welch, M., and Spring, D. R. (2004) Synthesis and stability of small molecule probes for Pseudomonas aeruginosa quorum sensing modulation Org. Biomol. Chem. 2, 3329-3336
7. Hodgkinson, J. T., Welch, M., and Spring, D. R. (2007) Learning the language of bacteria ACS Chem. Biol. 2, 715-717 (Pubitemid 350285906)
8. Geske, G. D., ONeill, J. C., and Blackwell, H. E. (2007) N -Phenylacetanoyl- l -homoserine lactones can strongly antagonize or superagonize quorum sensing in Vibrio fischeri ACS Chem. Biol. 2, 315-319 (Pubitemid 350001579)
9. Roy, V., Fernandes, R., Tsao, C. Y., and Bentley, W. E. (2010) Cross species quorum quenching using a native AI-2 processing enzyme ACS Chem. Biol. 5, 223-232
10. Roy, V., Smith, J. A., Wang, J., Stewart, J. E., Bentley, W. E., and Sintim, H. O. (2010) Synthetic analogs tailor native AI-2 signaling across bacterial species J. Am. Chem. Soc. 132, 11141-11150
11. Sintim, H. O., Smith, J. A., Wang, J., Nakayama, S., and Yan, L. (2010) Paradigm shift in discovering next-generation anti-infective agents: targeting quorum sensing, c-di-GMP signaling and biofilm formation in bacteria with small molecules Future Med. Chem. 2, 1005-1035
12. Roy, V., Adams, B. L., and Bentley, W. E. (2011) Developing next generation antimicrobials by intercepting AI-2 mediated quorum sensing Enzyme Microb. Technol. 49, 113-123
13. George, E. A., Novick, R. P., and Muir, T. W. (2008) Cyclic peptide inhibitors of staphylococcal virulence prepared by Fmoc-based thiolactone peptide synthesis J. Am. Chem. Soc. 130, 4914-4924 (Pubitemid 351500125)
14. Lyon, G. J., Wright, J. S., Muir, T. W., and Novick, R. P. (2002) Key determinants of receptor activation in the agr autoinducing peptides of Staphylococcus aureus Biochemistry 41, 10095-10104 (Pubitemid 34839755)
15. Geske, G. D., Wezeman, R. J., Siegel, A. P., and Blackwell, H. E. (2005) Small molecule inhibitors of bacterial quorum sensing and biofilm formation J. Am. Chem. Soc. 127, 12762-12763 (Pubitemid 41339140)
16. Smith, K. M., Bu, Y. G., and Suga, H. (2003) Induction and inhibition of Pseudomonas aeruginosa quorum sensing by synthetic autoinducer analogs Chem. Biol. 10, 81-89 (Pubitemid 36154477)
17. Malladi, V. L., Sobczak, A. J., Maricic, N., Murugapiran, S. K., Schneper, L., Makemson, J., Mathee, K., and Wnuk, S. F. (2011) Substituted lactam and cyclic azahemiacetals modulate Pseudomonas aeruginosa quorum sensing Bioorg. Med. Chem. 19, 5500-5506
18. Semmelhack, M. F., Campagna, S. R., Federle, M. J., and Bassler, B. L. (2005) An expeditious synthesis of DPD and boron binding studies Org. Lett. 7, 569-572 (Pubitemid 40353443)
19. Lowery, C. A., Dickerson, T. J., and Janda, K. D. (2008) Interspecies and interkingdom communication mediated by bacterial quorum sensing Chem. Soc. Rev. 37, 1337-1346
20. Taga, M. E., Miller, S. T., and Bassler, B. L. (2003) Lsr-mediated transport and processing of AI-2 in Salmonella typhimurium Mol. Microbiol. 50, 1411-1427 (Pubitemid 37475870)
21. Wang, L., Li, J., March, J. C., Valdes, J. J., and Bentley, W. E. (2005) luxS-dependent gene regulation in Escherichia coli K-12 revealed by genomic expression profiling J. Bacteriol. 187, 8350-8360 (Pubitemid 41780499)
22. Xavier, K. B. and Bassler, B. L. (2005) Regulation of uptake and processing of the quorum-sensing autoinducer AI-2 in Escherichia coli J. Bacteriol. 187, 238-248 (Pubitemid 40024200)
23. Surette, M. G., Miller, M. B., and Bassler, B. L. (1999) Quorum sensing in Escherichia coli, Salmonella typhimurium, and Vibrio harveyi: a new family of genes responsible for autoinducer production Proc. Natl. Acad. Sci. U.S.A. 96, 1639-1644 (Pubitemid 29098504)
24. Chen, X., Schauder, S., Potier, N., Van Dorsselaer, A., Pelczer, I., Bassler, B. L., and Hughson, F. M. (2002) Structural identification of a bacterial quorum-sensing signal containing boron Nature 415, 545-549 (Pubitemid 34130611)
25. Miller, S. T., Xavier, K. B., Campagna, S. R., Taga, M. E., Semmelhack, M. F., Bassler, B. L., and Hughson, F. M. (2004) Salmonella typhimurium recognizes a chemically distinct form of the bacterial quorum-sensing signal AI-2 Mol. Cell 15, 677-687 (Pubitemid 39194899)
26. Ni, N., Choudhary, G., Li, M., and Wang, B. (2008) Pyrogallol and its analogs can antagonize bacterial quorum sensing in Vibrio harveyi Biorg. Med. Chem. Lett. 18, 1567-1572 (Pubitemid 351318261)
27. Lowery, C. A., Park, J., Kaufmann, G. F., and Janda, K. D. (2008) An unexpected switch in the modulation of AI-2-based quorum sensing discovered through synthetic 4,5-dihydroxy-2,3-pentanedione analogues J. Am. Chem. Soc. 130, 9200-9201 (Pubitemid 352031109)
28. Tsuchikama, K., Lowery, C. A., and Janda, K. D. (2011) Probing autoinducer-2 based quorum sensing: the biological consequences of molecules unable to traverse equilibrium States J. Org. Chem. 76, 6981-6989
29. Kamaraju, K., Smith, J., Wang, J., Roy, V., Sintim, H. O., Bentley, W. E., and Sukharev, S. (2011) Effects on membrane lateral pressure suggest permeation mechanisms for bacterial quorum signaling molecules Biochemistry 50, 6983-6993
30. Wang, L., Hashimoto, Y., Tsao, C. Y., Valdes, J. J., and Bentley, W. E. (2005) Cyclic AMP (cAMP) and cAMP receptor protein influence both synthesis and uptake of extracellular autoinducer 2 in Escherichia coli J. Bacteriol. 187, 2066-2076 (Pubitemid 40316237)
31. Connell, N., Han, Z., Moreno, F., and Kolter, R. (1987) An E. coli promoter induced by the cessation of growth Mol. Microbiol. 1, 195-201
32. Tsao, C. Y., Hooshangi, S., Wu, H. C., Valdes, J. J., and Bentley, W. E. (2010) Autonomous induction of recombinant proteins by minimally rewiring native quorum sensing regulon of E. coli Metab. Eng. 12, 291-297
33. Smith, J. A., Wang, J., Nguyen-Mau, S. M., Lee, V., and Sintim, H. O. (2009) Biological screening of a diverse set of AI-2 analogues in Vibrio harveyi suggests that receptors which are involved in synergistic agonism of AI-2 and analogues are promiscuous Chem. Commun. (Cambridge, U. K.) 7033-7035
34. Xavier, K. B., Miller, S. T., Lu, W., Kim, J. H., Rabinowitz, J., Pelczer, I., Semmelhack, M. F., and Bassler, B. L. (2007) Phosphorylation and processing of the quorum-sensing molecule autoinducer-2 in enteric bacteria ACS Chem. Biol. 2, 128-136 (Pubitemid 47490234)
35. Hassett, D. J., Charniga, L., Bean, K., Ohman, D. E., and Cohen, M. S. (1992) Response of Pseudomonas aeruginosa to pyocyanin: mechanisms of resistance, antioxidant defenses, and demonstration of a manganese-cofactored superoxide dismutase Infect. Immun. 60, 328-336
36. Dietrich, L. E., Price-Whelan, A., Petersen, A., Whiteley, M., and Newman, D. K. (2006) The phenazine pyocyanin is a terminal signalling factor in the quorum sensing network of Pseudomonas aeruginosa Mol. Microbiol. 61, 1308-1321 (Pubitemid 44215429)
37. Duan, K. M., Dammel, C., Stein, J., Rabin, H., and Surette, M. G. (2003) Modulation of Pseudomonas aeruginosa gene expression by host microflora through interspecies communication Mol. Microbiol. 50, 1477-1491 (Pubitemid 38010446)
38. Xavier, K. B. and Bassler, B. L. (2005) Interference with AI-2-mediated bacterial cell-cell communication Nature 437, 750-753 (Pubitemid 41486545)
39. Armbruster, C. E., Hong, W., Pang, B., Weimer, K. E., Juneau, R. A., Turner, J., and Swords, W. E. (2010) Indirect pathogenicity of Haemophilus influenzae and Moraxella catarrhalis in polymicrobial otitis media occurs via interspecies quorum signaling mBio 1 (3) e00102-110
40. Merritt, J., Qi, F., Goodman, S. D., Anderson, M. H., and Shi, W. (2003) Mutation of luxS affects biofilm formation in Streptococcus mutans Infect. Immun. 71, 1972-1979 (Pubitemid 36368730)
41. Wen, Z. T. and Burne, R. A. (2004) LuxS-mediated signaling in Streptococcus mutans is involved in regulation of acid and oxidative stress tolerance and biofilm formation J. Bacteriol. 186, 2682-2691 (Pubitemid 38525922)
42. Miller, J. (1972) Experiments in Molecular Genetics, Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY.
43. Essar, D. W., Eberly, L., Hadero, A., and Crawford, I. P. (1990) Identification and characterization of genes for a second anthranilate synthase in Pseudomonas aeruginosa: interchangeability of the two anthranilate synthases and evolutionary implications J. Bacteriol. 172, 884-900 (Pubitemid 20070400)