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Chemical Compound Review

Pyocyanin     5-methylphenazin-1-one

Synonyms: Sanasin, Sanazin, PYOCYANINE, Pyrocyanine, SureCN689070, ...
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Disease relevance of PYOCYANINE

  • Pyocyanin, a secretory product of Pseudomonas aeruginosa, has the capacity to undergo redox cycling under aerobic conditions with resulting generation of superoxide and hydrogen peroxide [1].
  • Pseudomonas aeruginosa produces copious amounts of the redoxactive tricyclic compound pyocyanin that kills competing microbes and mammalian cells, especially during cystic fibrosis lung infection [2].
  • Cyanide-insensitive respiration, used as an indicator of intracellular superoxide and/or hydrogen peroxide production, was 50-fold less in pyocyanin-treated P. aeruginosa than in E. coli [3].
  • The Pseudomonas aeruginosa secretory product pyocyanin inactivates alpha1 protease inhibitor: implications for the pathogenesis of cystic fibrosis lung disease [4].
  • Subcellular site(s) of pyocyanin redox cycling and toxicity have not been well studied [5].

Psychiatry related information on PYOCYANINE

  • From these results we conclude that this property of pyocyanine may lead to suppression of specific defense mechanisms and enhance harmful inflammatory reactions of the host during infection with Pseudomonas aeruginosa [6].

High impact information on PYOCYANINE


Chemical compound and disease context of PYOCYANINE

  • These data suggest the possibility that the P. aeruginosa secretory products pyocyanin and pyochelin may act synergistically via the generation of hydroxyl radical to damage local tissues at sites of pseudomonas infection [1].
  • Cell extracts from E. coli contained an NADPH:pyocyanin oxidoreductase which increased the rate of reduction of pyocyanin by NADPH [3].
  • The effects of the Pseudomonas aeruginosa-derived pigments, pyocyanin and 1-hydroxyphenazine (1-hp), on membrane-associated oxidative metabolism and release of lysozomal enzymes by human neutrophils were investigated in vitro [10].
  • These data suggest that pyocyanin could contribute to lung injury in the P. aeruginosa-infected airway of cystic fibrosis patients by decreasing the ability of alpha1PI to control the local activity of serine proteases [4].
  • The ability of unstimulated human PMNL to metabolize exogenous LTB4 was found to be inhibited by pyocyanin, a phenazine derivative produced by Pseudomonas aeruginosa, in a dose-dependent manner [11].

Biological context of PYOCYANINE

  • Pyocyanin-induced apoptosis was associated with rapid and sustained generation of reactive oxygen intermediates and subsequent reduction of intracellular cAMP [12].
  • Evidence is provided to show that the mexEF-oprN operon may be involved in the excretion of intermediates for the biosynthesis of pyocyanin, a typical secondary metabolite of P. aeruginosa [13].
  • Through mutational analysis, we show that pyocyanin is the physiological signal for the upregulation of these quorum sensing-controlled genes during stationary phase and that the response is mediated by the transcription factor SoxR [14].
  • In parallel, the gacA gene dosage markedly influenced the BHL/RhIR-dependent formation of the cytotoxic compounds pyocyanin and cyanide and the exoenzyme lipase [15].
  • All cells treated with pyocyanin (10 muM) converted to the senescent phenotype, which remained stable for up to 7 days [16].

Anatomical context of PYOCYANINE

  • As assessed by 51Cr release, endothelial cells which were treated with pyocyanin or ferripyochelin alone demonstrated minimal injury [1].
  • In clinical isolates of P. aeruginosa pyocyanin production was associated with a proapoptotic effect upon neutrophils in culture [12].
  • To determine the mechanism of the inhibitory action of pyocyanine, we studied its effect on the early stages of T cell activation [17].
  • Pyocyanin induced a concentration- and time-dependent acceleration of neutrophil apoptosis, with 50 microM pyocyanin causing a 10-fold induction of apoptosis at 5 h (p < 0.001), a concentration that has been documented in sputum from patients colonized with P. aeruginosa [12].
  • At a pyocyanine concentration of 0.1 micrograms/ml or less the proliferation of T and B lymphocytes was enhanced, but at 0.5 micrograms/ml it was suppressed [6].

Associations of PYOCYANINE with other chemical compounds


Gene context of PYOCYANINE


Analytical, diagnostic and therapeutic context of PYOCYANINE


  1. Interaction of the Pseudomonas aeruginosa secretory products pyocyanin and pyochelin generates hydroxyl radical and causes synergistic damage to endothelial cells. Implications for Pseudomonas-associated tissue injury. Britigan, B.E., Roeder, T.L., Rasmussen, G.T., Shasby, D.M., McCormick, M.L., Cox, C.D. J. Clin. Invest. (1992) [Pubmed]
  2. Human targets of Pseudomonas aeruginosa pyocyanin. Ran, H., Hassett, D.J., Lau, G.W. Proc. Natl. Acad. Sci. U.S.A. (2003) [Pubmed]
  3. Response of Pseudomonas aeruginosa to pyocyanin: mechanisms of resistance, antioxidant defenses, and demonstration of a manganese-cofactored superoxide dismutase. Hassett, D.J., Charniga, L., Bean, K., Ohman, D.E., Cohen, M.S. Infect. Immun. (1992) [Pubmed]
  4. The Pseudomonas aeruginosa secretory product pyocyanin inactivates alpha1 protease inhibitor: implications for the pathogenesis of cystic fibrosis lung disease. Britigan, B.E., Railsback, M.A., Cox, C.D. Infect. Immun. (1999) [Pubmed]
  5. Subcellular localization of Pseudomonas pyocyanin cytotoxicity in human lung epithelial cells. O'Malley, Y.Q., Abdalla, M.Y., McCormick, M.L., Reszka, K.J., Denning, G.M., Britigan, B.E. Am. J. Physiol. Lung Cell Mol. Physiol. (2003) [Pubmed]
  6. Inhibitory and stimulatory effects of Pseudomonas aeruginosa pyocyanine on human T and B lymphocytes and human monocytes. Ulmer, A.J., Pryjma, J., Tarnok, Z., Ernst, M., Flad, H.D. Infect. Immun. (1990) [Pubmed]
  7. Structure and function of the phenazine biosynthetic protein PhzF from Pseudomonas fluorescens. Blankenfeldt, W., Kuzin, A.P., Skarina, T., Korniyenko, Y., Tong, L., Bayer, P., Janning, P., Thomashow, L.S., Mavrodi, D.V. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  8. Pyocyanin production by Pseudomonas aeruginosa induces neutrophil apoptosis and impairs neutrophil-mediated host defenses in vivo. Allen, L., Dockrell, D.H., Pattery, T., Lee, D.G., Cornelis, P., Hellewell, P.G., Whyte, M.K. J. Immunol. (2005) [Pubmed]
  9. Pyocyanin and its precursor phenazine-1-carboxylic acid increase IL-8 and intercellular adhesion molecule-1 expression in human airway epithelial cells by oxidant-dependent mechanisms. Look, D.C., Stoll, L.L., Romig, S.A., Humlicek, A., Britigan, B.E., Denning, G.M. J. Immunol. (2005) [Pubmed]
  10. Proinflammatory interactions of pyocyanin and 1-hydroxyphenazine with human neutrophils in vitro. Ras, G.J., Anderson, R., Taylor, G.W., Savage, J.E., Van Niekerk, E., Wilson, R., Cole, P.J. J. Infect. Dis. (1990) [Pubmed]
  11. Leukotriene B4 omega-oxidation by human polymorphonuclear leukocytes is inhibited by pyocyanin, a phenazine derivative produced by Pseudomonas aeruginosa. Muller, M., Sorrell, T.C. Infect. Immun. (1992) [Pubmed]
  12. Induction of neutrophil apoptosis by the Pseudomonas aeruginosa exotoxin pyocyanin: a potential mechanism of persistent infection. Usher, L.R., Lawson, R.A., Geary, I., Taylor, C.J., Bingle, C.D., Taylor, G.W., Whyte, M.K. J. Immunol. (2002) [Pubmed]
  13. Characterization of MexE-MexF-OprN, a positively regulated multidrug efflux system of Pseudomonas aeruginosa. Köhler, T., Michéa-Hamzehpour, M., Henze, U., Gotoh, N., Curty, L.K., Pechère, J.C. Mol. Microbiol. (1997) [Pubmed]
  14. The phenazine pyocyanin is a terminal signalling factor in the quorum sensing network of Pseudomonas aeruginosa. Dietrich, L.E., Price-Whelan, A., Petersen, A., Whiteley, M., Newman, D.K. Mol. Microbiol. (2006) [Pubmed]
  15. The global activator GacA of Pseudomonas aeruginosa PAO positively controls the production of the autoinducer N-butyryl-homoserine lactone and the formation of the virulence factors pyocyanin, cyanide, and lipase. Reimmann, C., Beyeler, M., Latifi, A., Winteler, H., Foglino, M., Lazdunski, A., Haas, D. Mol. Microbiol. (1997) [Pubmed]
  16. Premature cellular senescence induced by pyocyanin, a redox-active Pseudomonas aeruginosa toxin. Muller, M. Free Radic. Biol. Med. (2006) [Pubmed]
  17. Studies on the mechanism of T cell inhibition by the Pseudomonas aeruginosa phenazine pigment pyocyanine. Nutman, J., Berger, M., Chase, P.A., Dearborn, D.G., Miller, K.M., Waller, R.L., Sorensen, R.U. J. Immunol. (1987) [Pubmed]
  18. Pyocyanin induces oxidative stress in human endothelial cells and modulates the glutathione redox cycle. Muller, M. Free Radic. Biol. Med. (2002) [Pubmed]
  19. Direct oxidation of 2',7'-dichlorodihydrofluorescein by pyocyanin and other redox-active compounds independent of reactive oxygen species production. O'Malley, Y.Q., Reszka, K.J., Britigan, B.E. Free Radic. Biol. Med. (2004) [Pubmed]
  20. Augmentation of oxidant injury to human pulmonary epithelial cells by the Pseudomonas aeruginosa siderophore pyochelin. Britigan, B.E., Rasmussen, G.T., Cox, C.D. Infect. Immun. (1997) [Pubmed]
  21. A C. elegans orphan nuclear receptor contributes to xenobiotic resistance. Lindblom, T.H., Pierce, G.J., Sluder, A.E. Curr. Biol. (2001) [Pubmed]
  22. PtxR modulates the expression of QS-controlled virulence factors in the Pseudomonas aeruginosa strain PAO1. Carty, N.L., Layland, N., Colmer-Hamood, J.A., Calfee, M.W., Pesci, E.C., Hamood, A.N. Mol. Microbiol. (2006) [Pubmed]
  23. Advancing the quorum in Pseudomonas aeruginosa: MvaT and the regulation of N-acylhomoserine lactone production and virulence gene expression. Diggle, S.P., Winzer, K., Lazdunski, A., Williams, P., Cámara, M. J. Bacteriol. (2002) [Pubmed]
  24. Identification and characterization of genes for a second anthranilate synthase in Pseudomonas aeruginosa: interchangeability of the two anthranilate synthases and evolutionary implications. Essar, D.W., Eberly, L., Hadero, A., Crawford, I.P. J. Bacteriol. (1990) [Pubmed]
  25. Subversion of a lysosomal pathway regulating neutrophil apoptosis by a major bacterial toxin, pyocyanin. Prince, L.R., Bianchi, S.M., Vaughan, K.M., Bewley, M.A., Marriott, H.M., Walmsley, S.R., Taylor, G.W., Buttle, D.J., Sabroe, I., Dockrell, D.H., Whyte, M.K. J. Immunol. (2008) [Pubmed]
  26. Effects of pyocyanine, a blue pigment from Pseudomonas aeruginosa, on separate steps of T cell activation: interleukin 2 (IL 2) production, IL 2 receptor formation, proliferation and induction of cytolytic activity. Mühlradt, P.F., Tsai, H., Conradt, P. Eur. J. Immunol. (1986) [Pubmed]
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