Flavin model systems. 1. The electrochemistry of 1-hydroxyphenazine and pyocyanine in aprotic solvents

Morrison, Mark M.; Seo, Eddie T.; Howie, John K.; Sawyer, Donald T.

doi:10.1021/ja00469a035

Cited by 36 publications

(20 citation statements)

References 14 publications

(20 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…4 Detection offree radicalsformed after the exposure ofendothelial cells to pyocyanin. The above and earlier data (34)(35)(36) suggested that redox cycling ofpyocyanin could serve as a continuous source of 02-(and therefore H202) in biological systems. Endothelial cells are susceptible to H202-mediated injury (44)(45)(46)(47)(48)(49).…”

Section: )Chromium Releasementioning

confidence: 56%

“…The susceptibility of endothelial cells to oxidant-mediated injury is well recognized and has been implicated in the pathogenesis of a number of disease states (23). The P. aeruginosa secretory product pyocyanin can undergo redox cycling with resultant formation of O -/H202 (34)(35)(36). In addition, we have recently demonstrated that iron bound to the P. aeruginosa siderophore pyochelin is capable of catalyzing the formation of hydroxyl radical from 0-/H202 (21).…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

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.

Britigan¹,

Roeder²,

Rasmussen³

et al. 1992

J. Clin. Invest.

135

View full text Add to dashboard Cite

IntroductionPyocyanin, a secretory product of Pseudomonas aeruginosa, has the capacity to undergo redox cycling under aerobic conditions with resulting generation of superoxide and hydrogen peroxide. By using spin trapping techniques in conjunction with electron paramagnetic resonance spectrometry (EPR), superoxide was detected during the aerobic reduction of pyocyanin by NADH or porcine endothelial cells. No evidence of hydroxyl radical formation was detected. Chromium oxalate eliminated the EPR spectrum of the superoxide-derived spin adduct resulting from endothelial cell exposure to pyocyanin, suggesting superoxide formation close to the endothelial cell plasma membrane. We have previously reported that iron bound to the P. aeruginosa siderophore pyochelin (ferripyochelin) catalyzes the formation of hydroxyl free radical from superoxide and hydrogen peroxide via the Haber-Weiss reaction. In the present study, spin trap evidence of hydroxyl radical formation was detected when NADH and pyocyanin were allowed to react in the presence of ferripyochelin. Similarly, endothelial cell exposure to pyocyanin and ferripyochelin also resulted in hydroxyl radical production which appeared to occur in close proximity to the cell surface. As assessed by 51Cr release, endothelial cells which were treated with pyocyanin or ferripyochelin alone demonstrated minimal injury. However, endothelial cell exposure to the combination of pyochelin and pyocyanin resulted in 55% specific 51Cr release. Injury was not observed with the substitution of iron-free pyochelin and was diminished by the presence of catalase or dimethyl thiourea. 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. (J. Clin. Invest. 1992. 90:2187-2196

show abstract

Section: )Chromium Releasementioning

confidence: 56%

Section: Discussionmentioning

confidence: 99%

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.

Britigan¹,

Roeder²,

Rasmussen³

et al. 1992

J. Clin. Invest.

135

View full text Add to dashboard Cite

show abstract

“…Conversely to the two‐previous species, PYO redox behavior was more deeply studied in previous works reported in the literature , , .…”

Section: Resultsmentioning

confidence: 99%

Electrochemical Characterizations of four Main Redox–metabolites of Pseudomonas Aeruginosa

et al. 2017

View full text Add to dashboard Cite

Bacterial identification is of first importance in clinic nowadays. For few years, electrochemistry appears as a reliable route for characterizations outside of laboratories. Nowadays, researchers mainly focus on the opportunistic pathogen Pseudomonas aeruginosa because of its production of the Pyocyanin toxin which has an electrochemical case study behavior. Other P. aeruginosa secreted molecules are also studied in a lesser extent. This work deals with the systematic electrochemical characterizations in aprotic and protic solvents of 4 main metabolites of this bacterium in the view of multispecies detection of P. aeruginosa. We report here the behavior of the 2‐Heptyl‐4(1H)‐quinolone (HHQ), Pseudomonas Quinolone Signal (PQS), Pyocyanin (PYO) and the 2′aminoacetophenone (2‐AA). All the mentioned species are clearly visible by using electrochemical techniques (cyclic and square wave voltammetries). The 2 most suitable species for electrochemical detection appear to be PQS and PYO because of their detection at low potential.

show abstract

“…The purified pyocyanin preparation in 0.2 N HCI showed absorption maxima at 388, 282, 246, and 215 nm, characteristic of a purified preparation (see Fig. 2) (7,12,16). Crystals from the dried samples appeared as long, fine needles when viewed microscopically and melted between 134 and 135°C.…”

mentioning

confidence: 95%

Antibiotic action of pyocyanin

Baron¹,

Rowe²

1981

Antimicrob Agents Chemother

182

127

View full text Add to dashboard Cite

Biologically produced pyocyanin was purified, and the nature of its antibacterial action was determined for several bacteria. The pigment was shown to be bactericidal for all susceptible organisms. The bactericidal effect was dependent upon pyocyanin concentration and resulted in decreases in viability ranging from 1 to 8 log viable cells ml-'. The gram-positive bacteria were more susceptible as a group to the antibiotic, action than were the gram-negative bacteria. All apyocyanogenic pseudomonads tested were totally resistant to the pigment, suggesting that resistance may be a characteristic of the genus. Pseudomonas aeruginosa, the producer organism, was also essentially unaffected by high concentrations of pyocyanin. Facultative anaerobes were twofold or more times resistant to the action of the pigment under fermentative conditions; however, the antibiotic action did not require oxygen since denitriffying bacteria were more susceptible during anaerobic respiration than during aerobic respiration.Pyocyanin is a water-soluble blue-green phenazine pigment produced in large quantities by active cultures of Pseudomonas aeruginosa. Pyocyanin has antibiotic activity against bacteria (4), fungi (8), and protozoa (9), but is of little therapeutic value because it is quite toxic to eucaryotic cells (18). The physiological significance of the pigment is not known, but because of its inhibitory action, it has been postulated that pyocyanin production may give P. aeruginosa a selective advantage in certain growth situations. The nature of bacterial inhibition by the phenazine is neither well understood nor well documented, and no information is available concerning the effect of pyocyanin on the producer organism P. aeruginosa. Recently, Hassan and Fridovich (10) proposed that the inhibitory action of pyocyanin is the result of its unique redox potential. They propose that, during respiration, pyocyanin becomes reduced and univalently reduces oxygen to the toxic superoxide radical. The resistance of various bacteria to pyocyanin would therefore be dependent upon the levels of superoxide dismutase and catalase possessed by the organism and on the presence of oxygen.The purpose of this investigation was to determine the nature of the antibacterial action of pyocyanin and to characterize its inhibitory action on a variety of bacteria, including P. aeruginosa, under different environmental and physiological conditions. The results of our study demonstrate that the antimicrobial action of pyocyanin is bactericidal in nature and that the Media and culture conditions. The semidefined medium used for most of the experimentation contained the following per liter of deionized water: K2HPO4, 7.0 g; NaH2PO4. H20, 3.0 g; MgSO4.7H20, 0.24 g; (NH4)2SO4, 1.0 g; yeast extract, 1.0 g; and Dglucose, 1.0 g. The final pH was 7.0. A combination of the first three ingredients per liter of water will be referred to as basal salts solution (pH 7.0). The entire medium as described will be referred to as medium A. When needed, medium A was supple...

show abstract

Flavin model systems. 1. The electrochemistry of 1-hydroxyphenazine and pyocyanine in aprotic solvents

Cited by 36 publications

References 14 publications

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.

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.

Electrochemical Characterizations of four Main Redox–metabolites of Pseudomonas Aeruginosa

Antibiotic action of pyocyanin

Contact Info

Product

Resources

About