2,5-Piperazinedione inhibits quorum sensing-dependent factor production in Pseudomonas aeruginosa PAO1

Journal of Basic Microbiology

Volumn 52, Issue 6, 2012, Pages 679-686

  Musthafa, Khadar Syed ^a   Balamurugan, Krishnaswamy ^a   Pandian, Shunmugiah Karutha ^a   Ravi, Arumugam Veera ^a  

^a ALAGAPPA UNIVERSITY   (India)

Author keywords

2,5 Piperazinedione; Caenorhabditis elegans; Molecular docking; Pseudomonas aeruginosa; Swimming motility

Indexed keywords

3,6 BIS(5 CHLORO 2 PIPERIDYL) 2,5 PIPERAZINEDIONE; 3,6-BIS(5-CHLORO-2-PIPERIDYL)-2,5-PIPERAZINEDIONE; BACTERIAL PROTEIN; DRUG DERIVATIVE; GAMMA BUTYROLACTONE; HOMOSERINE; LASR PROTEIN, PSEUDOMONAS AERUGINOSA; N (3 OXODODECANOYL)HOMOSERINE LACTONE; N-(3-OXODODECANOYL)HOMOSERINE LACTONE; PIPERAZINE DERIVATIVE; PYOCYANINE; QSCR PROTEIN, PSEUDOMONAS AERUGINOSA; REPRESSOR PROTEIN; TRANSACTIVATOR PROTEIN; VIRULENCE FACTOR;

ANIMAL; ARTICLE; BIOSYNTHESIS; CAENORHABDITIS ELEGANS; DRUG ANTAGONISM; DRUG EFFECT; METABOLISM; MICROBIOLOGY; PSEUDOMONAS AERUGINOSA; QUORUM SENSING;

4-BUTYROLACTONE; ANIMALS; BACTERIAL PROTEINS; CAENORHABDITIS ELEGANS; HOMOSERINE; PIPERAZINES; PSEUDOMONAS AERUGINOSA; PYOCYANINE; QUORUM SENSING; REPRESSOR PROTEINS; TRANS-ACTIVATORS; VIRULENCE FACTORS;

CAENORHABDITIS ELEGANS; PSEUDOMONAS AERUGINOSA;

EID: 84871070357     PISSN: 0233111X     EISSN: 15214028     Source Type: Journal    
DOI: 10.1002/jobm.201100292     Document Type: Article

References (53)

1. Ranjan, K.P., Ranjan, N., Bansal, S.K., Arora, D.R., 2010. Prevalence of Pseudomonas aeruginosa in post operative wound infection in a referral hospital in Haryana, India. J. Lab. Physicians, 2, 74-77.
2. Nalca, Y., Jansch, L., Bredenbruch, F., Geffers, R. et al., 2006. Quorum sensing antagonistic activities of azithromycin in Pseudomonas aeruginosa PAO1: A global approach. Antimicrob. Agents Chemother., 50, 1680-1688.
3. Bjarnsholt, T., Givskov, M., 2007. Quorum sensing blockade as a strategy for enhancing host defences against bacterial pathogens. Phil. Trans. R. Soc. B., 362, 1213-1222.
4. Yang, L., Rybtke, M.T., Jakobsen, T.H., Hentzer, M. et al., 2009. Computer aided identification of recognized drugs as Pseudomonas aeruginosa quorum sensing inhibitors. Antimicrob. Agents Chemother., 53, 2432-2443.
5. Su, H.C., Ramkissoon, K., Doolittle, J., Clark, M. et al., 2010. The development of ciprofloxacin resistance in Pseudomonas aeruginosa involves multiple response stages and multiple proteins. Antimicrob. Agents Chemother., 54, 4626-4635.
6. Juan, C., Zamorano, L., Perez, J.L., Ge, Y. et al., 2010. Activity of a new antipseudomonal cephalosporin, CXA-101 (FR264205), against carbapenem resistant and multidrug-resistant Pseudomonas aeruginosa clinical strains. Antimicrob. Agents Chemother., 54, 846-851.
7. Kohler, T., Perron, G.G., Buckling, A., Delden, C.V., 2010. Quorum sensing inhibition selects for virulence and cooperation in Pseudomonas aeruginosa. PLoS Pathog., 6, e1000883.
8. de Kievit, T.R., Iglewski, B.H., 2000. Bacterial quorum sensing in pathogenic relationships. Infect. Immun., 68, 4839-4849.
9. Pesci, E.C., Pearson, J.P., Seed, P.C., Iglewski, B.H., 1997. Regulation of las and rhl quorum sensing in Pseudomonas aeruginosa. J. Bacteriol., 179, 3127-3132.
10. Pearson, J.P., Pesci, E.C., Iglewski, B.H., 1997. Roles of Pseudomonas aeruginosa las and rhl quorum sensing systems in control of elastase and rhamnolipid biosynthesis genes. J. Bacteriol., 179, 5756-5767.
11. Williams, P., Winzer, K., Chan, W.C., Camara, M., 2007. Look who's talking: Communication and quorum sensing in the bacterial world. Phil. Trans. R. Soc. B., 362, 1119-1134.
12. Musthafa, K.S., Saroja, V., Pandian, S.K., Ravi, A.V., 2011. Antipathogenic potential of marine Bacillus sp. SS4 on N -acyl homoserine lactone mediated virulence factors production in Pseudomonas aeruginosa (PAO1). J. Bioscience., 36, 55-67.
13. Kazlauskas, R., Murphy, P.T., Wells, R.J., 1978. A diketopiperazine derived from trichloroleucine from the sponge Dysidea herbacea. Tetrahedron Lett., 49, 4945-4948.
14. Adamczeski, M., Reed, A.R., Crews, P., 1995. New and known diketopiperazines from the Caribbean sponge Calyx cf. podatypa. J. Nat. Prod., 58, 201-208.
15. de Rosa, S., Mitova, M., Tommonaro, G., 2003. Marine bacteria associated with sponge as source of cyclic peptides. Biomol. Eng., 20, 311-316.
16. Sjogren, M., Johnson, A.L., Hedner, E., Dahlstrom, M. et al., 2006. Antifouling activity of synthesized peptide analogs of the sponge metabolite barettin. Peptides, 27, 2058-2064.
17. Trigos, A., Reyna, S., Cervantes, L., 1995. Three diketopiperazines from the cultivated fungus Fusarium oxysporum. Nat. Prod. Lett., 6, 241-246.
18. Byun, H.G., Zhang, H.M.M., Adachi, K.S.Y., Lee, W.J. et al., 2003. Novel antifungal diketopiperazine from marine fungus. J. Antibiot., 56, 102-106.
19. Du, L., Feng, T., Zhao, B., Li, D. et al., 2010. Alkaloids from a deep ocean sediment-derived fungus Penicillium sp. and their antitumor activities. J. Antibiot., 63, 165-170.
20. Holden, M.T.G., Chhabra, S.R., de Nys, R., Stead, P. et al., 1999. Quorum sensing cross talk: Isolation and chemical characterization of cyclic dipeptides from Pseudomonas aeruginosa and other Gram-negative bacteria. Mol. Microbiol., 33, 1254-1266.
21. Qi, S.H., Xu, Y., Gao, J., Qian, P.Y. et al., 2009. Antibacterial and antilarval compounds from marine bacterium Pseudomonas rhizosphaerae. Ann. Microbiol., 59, 229-233.
22. Wang, G., Dai, S., Chen, M., Wu, H. et al., 2010. Two diketopiperazine cyclo (Pro-Phe) isomers from marine bacteria Bacillus subtilis sp. 13-2. Chem. Nat. Compd., 46, 583-585.
23. Prasad, C., 1995. Bioactive cyclic dipeptides. Peptides, 16, 151-164.
24. Musetti, R., Polizzotto, R., Vecchione, A., Borselli, S. et al., 2007. Antifungal activity of diketopiperazines extracted from Alternaria alternata against Plasmopara viticola: An ultrastructural study. Micron., 38, 643-650.
25. Li, X., Dobretsov, S., Xu, Y., Xiao, X. et al., 2006. Antifouling diketopiperazines produced by a deep-sea bacterium, Streptomyces fungicidicus. Biofouling, 22, 201-208.
26. O'Neill, J.C., Lin, Q., Geske, G.D., Blackwell H.E., 2009. New and unexpected insights into the modulation of LuxR-type quorum sensing by cyclic dipeptides. ACS Chem. Biol., 4, 1051-1059.
27. Kessler, E., Safrin, M., Olson, J.C., Ohman, D.E., 1993. Secreted LasA of Pseudomonas aeruginosa is a staphylolytic protease. J. Biol. Chem., 268, 7503-7508.
28. Ohman, D.E., Cryz, S.J., Iglewski, B.H., 1980. Isolation and characterization of a Pseudomonas aeruginosa PAO mutant that produces altered elastase. J. Bacteriol., 142, 836-842.
29. Essar, D.W., Eberly, L., Hadero, A., 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.
30. Favre-Bonte, S., Kohler, T., Delden, C.V., 2003. Biofilm formation by Pseudomonas aeruginosa: Role of the C4-HSL cell-to-cell signal and inhibition by azithromycin. J. Antimicrob. Chemother., 52, 598-604.
31. Moy, T.I., Ball, A.R., Anklesaria, Z., Casadei, G. et al., 2006. Identification of novel antimicrobials using a live-animal infection model. PNAS, 103, 10414-10419.
32. Sivamaruthi, B.S., Ganguli, A., Kumar, M., Bhaviya, S. et al., 2011. Caenorhabditis elegans as a model for studying Cronobacter sakazakii ATCC BAA-894 pathogenesis. J. Basic Microbiol., 51, 1-10.
33. McLean, R.J., Pierson, L.S., Fuqua, C., 2004. A simple screening protocol for the identification of quorum signal antagonists. J. Microbiol. Methods., 58, 351-360.
34. Rajamani, S., Bauer, W.D., Robinson, J.B., Farrow, J.M. et al., 2008. The vitamin riboflavin and its derivative lumichrome activate the LasR bacterial quorum-sensing receptor. Mol. Plant Microbe Interact., 21, 1184-1192.
35. Shih, P.C., Huang, C.T., 2002. Effects of quorum sensing deficiency on Pseudomonas aeruginosa biofilm formation and antibiotic resistance. J. Antimicrob. Chemother., 49, 309-314.
36. Deligianni, E., Pattison, S., Berrar, D., Ternan, N.G. et al., 2010. Pseudomonas aeruginosa cystic fibrosis isolates of similar RAPD genotype exhibit diversity in biofilm forming ability in vitro. BMC Microbiol., 10, 38.
37. Kessler, E., Israel, M., Landshman, N., Chechick, A. et al., 1982. In vitro inhibition of Pseudomonas aeruginosa elastase by metal chelating peptide derivatives. Infect. Immun., 38, 716-723.
38. Vandeputte, O.M., Kiendrebeogo, M., Rasamiravaka, T., Stévigny, C. et al., 2011. The flavanone naringenin reduces the production of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa PAO1. Microbiology, 157, 2120-2132.
39. Khan, M.S.A., Zahin, M., Hasan, S., Husain, F.M. et al., 2009. Inhibition of quorum sensing regulated bacterial functions by plant essential oils with special reference to clove oil. Lett. Appl. Microbiol., 49, 354-360.
40. Musthafa, K.S., Ravi, A.V., Annapoorani, A., Packiavathy, I.S.V. et al., 2010. Evaluation of antiquorum sensing activity of edible plants and fruits through inhibition of the N -acyl homoserine lactone system in Chromobacterium violaceum and Pseudomonas aeruginosa. Chemotherapy, 56, 333-339.
41. Karatuna, O., Yagci, A., 2010. Analysis of quorum sensing dependent virulence factor production and its relationship with antimicrobial susceptibility in Pseudomonas aeruginosa respiratory isolates. Clin. Microbiol. Infect., 16, 1770-1775.
42. Fothergill, J.L., Panagea, S., Hart, C.A., Walshaw, M.J. et al., 2007. Widespread pyocyanin overproduction among isolates of a cystic fibrosis epidemic strain. BMC Microbiol., 7, 45.
43. Usher, L.R., Lawson, R.A., Geary, I., Taylor, C.J. et al., 2002. Induction of neutrophil apoptosis by the Pseudomonas aeruginosa exotoxin pyocyanin: A potential mechanism of persistent infection. J. Immunol., 168, 1861-1868.
44. Muh, U., Schuster, M., Heim, R., Singh, A. et al., 2006. Novel Pseudomonas aeruginosa quorum sensing inhibitors identified in an ultra high throughput screen. Antimicrob. Agents Chemother., 50, 3674-3679.
45. Ishida, T., Ikeda, T., Takiguchi, N., Kuroda, A. et al., 2007. Inhibition of quorum sensing in Pseudomonas aeruginosa by N -acyl cyclopentylamides. Appl. Environ. Microbiol., 73, 3183-3188.
46. Vu, B., Chen, M., Crawford, R.J., Ivanova, E.P., 2009. Bacterial extracellular polysaccharides involved in biofilm formation. Molecules, 14, 2535-2554.
47. Wu, H., Lee, B., Yang, L., Wang, H., 2011. Effects of ginseng on Pseudomonas aeruginosa motility and biofilm formation. FEMS Immunol. Med. Microbiol., 62, 49-56.
48. Bandara, M.B.K., Zhu, H., Sankaridurg, P. R., Willcox, M.D.P., 2006. Salicylic acid reduces the production of several potential virulence factors of Pseudomonas aeruginosa associated with microbial keratitis. Invest. Ophthalmol. Vis. Sci., 47, 4453-4460.
49. Breger, J., Fuchs, B.B., Aperis, G., Moy, T.I. et al., 2007. Antifungal chemical compounds identified using a C. elegans pathogenicity assay. PLoS Pathog., 3, 168-178.
50. Adonizio, A., Leal, S.M., Ausubel, F.M., Mathee, K., 2008. Attenuation of Pseudomonas aeruginosa virulence by medicinal plants in a Caenorhabditis elegans model system. J. Med. Microbiol., 57, 809-813.
51. Campbell, J., Blackwell, H.E., 2009. Efficient construction of diketopiperazine macroarrays through a cyclative cleavage strategy and their evaluation as luminescence inhibitors in the bacterial symbiont Vibrio fischeri. J. Comb. Chem., 11, 1094-1099.
52. Galloway, W.R.J.D., Hodgkinson, J.T., Bowden, S.T., Welch, M. et al., 2011. Quorum sensing in Gram-negative bacteria: Small molecule modulation of AHL and AI-2 quorum sensing pathways. Chem. Rev., 111, 28-67.
53. Geske, G.D., O'Neill, J.C., Miller, D.M., Mattmann, M.E. et al., 2007. Modulation of bacterial quorum sensing with synthetic ligands: Systematic evaluation of N -acylated homoserine lactones in multiple species and new insights into their mechanisms of action. J. Am. Chem. Soc., 129, 13613-13625.