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<title>Pyocyanin</title>

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<span id="openzim-page-title" class="mw-page-title-main"><span class="mw-page-title-main">Pyocyanin</span></span>

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<caption>Pyocyanin<sup id="cite_ref-1" class="reference"><a href="#cite_note-1"><span class="cite-bracket">[</span>1<span class="cite-bracket">]</span></a></sup>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Names

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<td colspan="2" style="text-align:left;"><a href="Preferred_IUPAC_name" title="Preferred IUPAC name">Preferred IUPAC name</a>

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0; max-width:22em;">5-Methylphenazin-1(5<i>H</i>)-one</div></div>

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<td colspan="2" style="text-align:left;">Other names

<div style="max-width:22em; word-wrap:break-word; padding-left:1.7em;">Pyocyanin; Pyrocyanine; 5-Methyl-1(5<i>H</i>)-phenazinone; Sanasin; Sanazin</div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Identifiers

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CAS_Registry_Number" title="CAS Registry Number">CAS Number</a></div>

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</style><div class="plainlist"><ul><li><span title="commonchemistry.cas.org"><a rel="nofollow" class="external text" href="https://commonchemistry.cas.org/detail?cas_rn=85-66-5">85-66-5</a></span><sup> <span typeof="mw:File"><span></span></span><span style="display:none">Y</span></sup></li></ul></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">3D model (<a href="JSmol" class="mw-redirect" title="JSmol">JSmol</a>)</div>

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<td><div class="plainlist"><ul><li><span title="chemapps.stolaf.edu (3D interactive model)"><a rel="nofollow" class="external text" href="https://chemapps.stolaf.edu/jmol/jmol.php?model=CN1C2%3DCC%3DCC%3DC2N%3DC3C1%3DCC%3DCC3%3DO">Interactive image</a></span></li></ul></div>

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<td><a href="ChEBI" title="ChEBI">ChEBI</a>

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<td><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chebi/searchId.do?chebiId=8653">CHEBI:8653</a></span></li></ul></div>

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<td><a href="ChEMBL" title="ChEMBL">ChEMBL</a>

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<td><div class="plainlist"><ul><li><span title="www.ebi.ac.uk"><a rel="nofollow" class="external text" href="https://www.ebi.ac.uk/chembl/explore/compound/ChEMBL2289232">ChEMBL2289232</a></span></li></ul></div>

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<td><a href="ChemSpider" title="ChemSpider">ChemSpider</a>

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<td><a href="ECHA_InfoCard" class="mw-redirect" title="ECHA InfoCard"><span title="echa.europa.eu">ECHA InfoCard</span></a>

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<td><a href="European_Community_number" title="European Community number"><span title="European Community number (chemical identifier)">EC Number</span></a>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="PubChem" title="PubChem">PubChem</a> <abbr title="Compound ID">CID</abbr></div>

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="CompTox_Chemicals_Dashboard" title="CompTox Chemicals Dashboard">CompTox Dashboard</a> <span style="font-weight:normal">(<abbr title="U.S. Environmental Protection Agency">EPA</abbr>)</span></div>

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<td><div class="plainlist"><ul><li><span title="comptox.epa.gov"><a rel="nofollow" class="external text" href="https://comptox.epa.gov/dashboard/chemical/details/DTXSID9041108">DTXSID9041108</a> </span></li></ul></div>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="International_Chemical_Identifier" title="International Chemical Identifier">InChI</a></div></div>

<ul class="mw-collapsible-content" style="margin-top: 0; margin-bottom: 0; line-height: inherit; list-style: none; margin-left: 0; word-break:break-all;"><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1S/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YNCMLFHHXWETLD-UHFFFAOYSA-N</div></div></li><li style="line-height: inherit; margin: 0"><div style="border-top:1px solid #ccc; padding:0.2em 0 0.2em 1.5em; text-align:left;"><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">InChI=1/C13H10N2O/c1-15-10-6-3-2-5-9(10)14-13-11(15)7-4-8-12(13)16/h2-8H,1H3</div><div style="word-wrap:break-word; text-indent:-1.5em; font-size:97%; line-height:120%;">Key: YNCMLFHHXWETLD-UHFFFAOYAI</div></div></li></ul>

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<div style="line-height: 1.6em; font-weight: bold; text-align:left; font-weight:normal;"><div><a href="Simplified_molecular-input_line-entry_system" class="mw-redirect" title="Simplified molecular-input line-entry system">SMILES</a></div></div>

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Properties

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<td><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Chemical_formula" title="Chemical formula">Chemical formula</a></div>

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<td><a href="Molar_mass" title="Molar mass">Molar mass</a>

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<td>Appearance

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<td>Solid

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<th colspan="2" style="background: #f8eaba;color:inherit; text-align: center;">Hazards

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<td colspan="2" style="text-align:left; background-color:#eaeaea;color:inherit;"><a href="Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals" title="Globally Harmonized System of Classification and Labelling of Chemicals"><b>GHS</b> labelling</a>:

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_hazard_pictograms" title="GHS hazard pictograms">Pictograms</a></div>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="Globally_Harmonized_System_of_Classification_and_Labelling_of_Chemicals#Signal_word" title="Globally Harmonized System of Classification and Labelling of Chemicals">Signal word</a></div>

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<td><b>Danger</b>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_hazard_statements" title="GHS hazard statements">Hazard statements</a></div>

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<td style="padding-left:1em;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;"><a href="GHS_precautionary_statements" title="GHS precautionary statements">Precautionary statements</a></div>

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<td colspan="2" style="text-align:left; background:#f8eaba; color:inherit; border:1px solid #a2a9b1;"><div style="display: inline-block; line-height: 1.2em; padding: .1em 0;">Except where otherwise noted, data are given for materials in their <a href="Standard_state" title="Standard state">standard state</a> (at 25 °C [77 °F], 100 kPa).</div>

<div style="margin-top: 0.3em;"><div style="text-align:center;"><span typeof="mw:File"><span></span></span><span style="display:none">Y</span> <span class="reflink nourlexpansion"><a class="external text external" href="https://en.wikipedia.org/w/index.php?title=Special:ComparePages&rev1=424707501&page2=Pyocyanin">verify</a></span> (what is <sup><span typeof="mw:File"><span></span></span><span style="display:none">Y</span><span typeof="mw:File"><span></span></span><span style="display:none">N</span></sup> ?)

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<div style="margin-top: 0.3em; text-align: center;">Infobox references</div>

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<p><b>Pyocyanin</b> (PCN<sup>−</sup>) is one of the many toxic compounds produced and secreted by the <a href="Gram_negative_bacterium" class="mw-redirect" title="Gram negative bacterium">Gram negative bacterium</a> <i><a href="Pseudomonas_aeruginosa" title="Pseudomonas aeruginosa">Pseudomonas aeruginosa</a></i>. Pyocyanin is a blue secondary metabolite, turning red below pH 4.9, with the ability to oxidise and reduce other molecules<sup id="cite_ref-2" class="reference"><a href="#cite_note-2"><span class="cite-bracket">[</span>2<span class="cite-bracket">]</span></a></sup> and therefore kill microbes competing against <i>P. aeruginosa</i> as well as mammalian cells of the lungs which <i>P. aeruginosa</i> has infected during <a href="Cystic_fibrosis" title="Cystic fibrosis">cystic fibrosis</a>.<sup id="cite_ref-3" class="reference"><a href="#cite_note-3"><span class="cite-bracket">[</span>3<span class="cite-bracket">]</span></a></sup><sup id="cite_ref-4" class="reference"><a href="#cite_note-4"><span class="cite-bracket">[</span>4<span class="cite-bracket">]</span></a></sup> Since pyocyanin is a <a href="Zwitterion" title="Zwitterion">zwitterion</a> at blood pH, it is easily able to cross the cell membrane. There are three different states in which pyocyanin can exist: oxidized (blue), monovalently reduced (colourless) or divalently reduced (red). Mitochondria play an important role in the cycling of pyocyanin between its redox states. Due to its redox-active properties, pyocyanin generates <a href="Reactive_oxygen_species" title="Reactive oxygen species">reactive oxygen species</a>.

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<div class="mw-heading mw-heading2"><h2 id="Biosynthesis">Biosynthesis</h2></div>

<p>Pyocyanin biosynthesis begins with the synthesis of the phenazine-1-carboxylic acid (PCA) core.<sup id="cite_ref-MavrodiBonsall2001_5-0" class="reference"><a href="#cite_note-MavrodiBonsall2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup> In this reaction the enzyme PhzE catalyzes the loss of the hydroxyl group from C4 of Chorismic Acid as well as the transfer of an amine group from glutamine to form glutamic acid and 2-amino-2-desoxyisochorismic acid (ADIC).<sup id="cite_ref-BlankenfeldtParsons2014_6-0" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> Following this, PhzD catalyzes the hydrolytic removal the pyruvate moiety from ADIC to form (5S,6S)-6-amino-5-hydroxy-1,3-cyclohexadieve-1-carboxylic acid (DHHA).<sup id="cite_ref-BlankenfeldtParsons2014_6-1" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In the next step, PhzF catalyzes two steps: the abstraction of a hydrogen from C3 of DHHA, delocalization of the double bond system and reprotonation at C1 as well as enol tautomerization to form the highly unstable 6-amino-5-oxocyclohex-2-ene-1-carboxylic acid (AOCHC).<sup id="cite_ref-BlankenfeldtParsons2014_6-2" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> From here two molecules of AOCHC are condensed by PhzB to form the tricyclic compound, hexahydrophenazine-1,6-dicarboxylic acid (HHPDC).<sup id="cite_ref-BlankenfeldtParsons2014_6-3" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The product of this reaction, HHPDC, is unstable and spontaneously undergoes oxidative decarboxylation in an uncatalyzed reaction to form tetrahydrophenazine-1,6-carboxylic acid (THPCA).<sup id="cite_ref-BlankenfeldtParsons2014_6-4" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> In the final step of phenazine-1-carboxylic acid synthesis the enzyme PhzG catalyzes the oxidation of THPCA to dihydro-phenazine-1-carboxylic acid.<sup id="cite_ref-BlankenfeldtParsons2014_6-5" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> This is the last catalyzed step in the production of PCA, the last step is an uncatalyzed oxidation of DHPCA to PCA.<sup id="cite_ref-BlankenfeldtParsons2014_6-6" class="reference"><a href="#cite_note-BlankenfeldtParsons2014-6"><span class="cite-bracket">[</span>6<span class="cite-bracket">]</span></a></sup> The conversion of PCA to Pyocyanin is achieved in two enzymatic steps: firstly, PCA is methylated on N5 to 5-methylphenazine-1-carboxylate betaine by the enzyme PhzM using the cofactor S-adenosyl-L-methionine and secondly, PhzS catalyzes the hydroxylative decarboxylation of this substrate to form the final product, Pyocyanin.<sup id="cite_ref-MavrodiBonsall2001_5-1" class="reference"><a href="#cite_note-MavrodiBonsall2001-5"><span class="cite-bracket">[</span>5<span class="cite-bracket">]</span></a></sup>

</p><p>The chromosomes of most <i>P. aeruginosa</i> strains carry two nearly identical operons, <i>phzA1B1C1D1E1F1G1</i> and <i>phzA2B2C2D2E2F2G2</i>, which encode the enzymes required to produce PCA.<sup id="cite_ref-7" class="reference"><a href="#cite_note-7"><span class="cite-bracket">[</span>7<span class="cite-bracket">]</span></a></sup> Transcription of these operons is controlled by <a href="Quorum_sensing" title="Quorum sensing">quorum sensing</a>, and more specifically by the Pseudomonas Quinolone Signal (PQS) system involving the transcriptional regulator MvfR (also known as PqsR). Conversion of PCA into pyocyanin is then achieved by the products of <i>phzS</i> and <i>phzS</i>, which are unique genes in the chromosome. Biosynthesis can be impaired by disrupting the <i>aro</i> pathway which is needed for the synthesis of chorismic acid from shikimate.<sup id="cite_ref-8" class="reference"><a href="#cite_note-8"><span class="cite-bracket">[</span>8<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Redox_warfare">Redox warfare</h2></div>

<p>Pyocyanin inactivates <a href="Catalase" title="Catalase">catalase</a> by reducing its gene’s transcription as well as directly targeting the enzyme itself. <a href="Glutathione" title="Glutathione">Glutathione</a> is an important antioxidant modulated by pyocyanin.<sup id="cite_ref-9" class="reference"><a href="#cite_note-9"><span class="cite-bracket">[</span>9<span class="cite-bracket">]</span></a></sup> In particular the pool of the reduced form is depleted while the oxidised form is promoted by hydrogen peroxide which is not dismutated by catalase.

In the cystic fibrosis lung, intracellular pyocyanin converts molecular oxygen to the superoxide free radical by oxidizing <a href="NADPH" class="mw-redirect" title="NADPH">NADPH</a> to NADP<sup>+</sup>. This has a doubly negative effect on the lungs. Firstly, the NADPH used by pyocyanin depletes the available substrate for the reaction catalysed by the <a href="NADPH_oxidase" title="NADPH oxidase">NADPH oxidase</a> enzyme. Secondly, the superoxide radical generated can inhibit <a href="Cytokines" class="mw-redirect" title="Cytokines">cytokines</a>, such as <a href="Interleukin_4" title="Interleukin 4">IL-4</a>, <a href="Interleukin_13" title="Interleukin 13">IL-13</a> and <a href="IFN-%CE%B3" class="mw-redirect" title="IFN-γ">IFN-γ</a>, which usually upregulate NADPH oxidase. When the lung is confronted with pyocyanin, an increased concentration of catalase and <a href="Superoxide_dismutase" title="Superoxide dismutase">superoxide dismutase</a> is seen in order to deal with the barrage of radicals being produced.<sup id="cite_ref-10" class="reference"><a href="#cite_note-10"><span class="cite-bracket">[</span>10<span class="cite-bracket">]</span></a></sup>

</p>

<div class="mw-heading mw-heading2"><h2 id="Targets">Targets</h2></div>

<p>Pyocyanin is able to target a wide range of cellular components and pathways. Pathways that are affected by pyocyanin include the <a href="Electron_transport_chain" title="Electron transport chain">electron transport chain</a>, vesicular transport, and cell growth. An enhanced susceptibility to pyocyanin is seen in cells with certain mutant proteins or complexes. Mutations in genes affecting <a href="V-ATPase" title="V-ATPase">V-ATPase</a> synthesis and assembly,<sup id="cite_ref-11" class="reference"><a href="#cite_note-11"><span class="cite-bracket">[</span>11<span class="cite-bracket">]</span></a></sup> vesicle transport machinery, and protein sorting machinery all confer an increased sensitivity to pyocyanin which further enhances the effects on cystic fibrosis on the patient. Vacuolar- ATPase in yeast cells is a particularly potent target as it is the main non-mitochondrial producer of ATP but also has numerous other functions such as calcium homeostatic control, the facilitation of receptor-mediated endocytosis and the degradation of proteins. Therefore, the inactivation of vacuolar-ATPase by hydrogen peroxide produced by pyocyanin has huge consequences for the lung. Additional to these effects, another target of pyocyanin is caspase 3-like proteases which can then go on to initiate <a href="Apoptosis" title="Apoptosis">apoptosis</a> and <a href="Necrosis" title="Necrosis">necrosis</a>. Mitochondrial electron carriers ubiquinone and nicotinic acid are also susceptible to pyocyanin.<sup id="cite_ref-12" class="reference"><a href="#cite_note-12"><span class="cite-bracket">[</span>12<span class="cite-bracket">]</span></a></sup> The cell cycle can be disturbed by the action of pyocyanin, and it can hinder the proliferation of <a href="Lymphocytes" class="mw-redirect" title="Lymphocytes">lymphocytes</a>.<sup id="cite_ref-13" class="reference"><a href="#cite_note-13"><span class="cite-bracket">[</span>13<span class="cite-bracket">]</span></a></sup> This is done by the generation of <a href="Reactive_oxygen_intermediate" class="mw-redirect" title="Reactive oxygen intermediate">reactive oxygen intermediates</a>, such as <a href="Hydrogen_peroxide" title="Hydrogen peroxide">hydrogen peroxide</a> and <a href="Superoxide" title="Superoxide">superoxide</a>, which cause oxidative stress by directly damaging DNA or by targeting other constituents of the cell cycle such as DNA recombination and repair machinery. Pyocyanin contributes to the disproportion of protease and antiprotease activity by disabling α<sub>1</sub>- protease inhibitor.

</p>

<div class="mw-heading mw-heading2"><h2 id="Cystic_fibrosis">Cystic fibrosis</h2></div>

<p>Many studies have concluded that pyocyanin has a derogatory effect in cystic fibrosis which enables <i>P. aeruginosa</i> to persist in the cystic fibrosis lung; it is often detected in the sputum of cystic fibrosis patients. Pyocyanin in vitro has the ability to interfere with functions such as ciliary beating and therefore cause epithelial dysfunction as the ciliary are needed to sweep mucus up the throat.<sup id="cite_ref-14" class="reference"><a href="#cite_note-14"><span class="cite-bracket">[</span>14<span class="cite-bracket">]</span></a></sup> Additionally, <a href="Neutrophil" title="Neutrophil">neutrophil</a> apoptosis,<sup id="cite_ref-15" class="reference"><a href="#cite_note-15"><span class="cite-bracket">[</span>15<span class="cite-bracket">]</span></a></sup> immunoglobulin release from <a href="B-lymphocytes" class="mw-redirect" title="B-lymphocytes">B-lymphocytes</a>, and interleukin release (e.g. <a href="Interleukin_8" title="Interleukin 8">IL-8</a><sup id="cite_ref-16" class="reference"><a href="#cite_note-16"><span class="cite-bracket">[</span>16<span class="cite-bracket">]</span></a></sup> and <a href="CCL5" title="CCL5">CCL5</a>) are all impaired by pyocyanin, weakening the immune system of the lung. In vivo studies have shown that the growth of fungus is inhibited in the presence of pyocyanin.<sup id="cite_ref-17" class="reference"><a href="#cite_note-17"><span class="cite-bracket">[</span>17<span class="cite-bracket">]</span></a></sup> The fungicidal mechanism is the activation of NAD(P)H to induce a redox-active cascade producing reactive oxygen intermediates. This allows <i>P. aeruginosa</i> to have a competitive advantage as it may dominate over other microorganisms in the cystic fibrosis lung.

The intracellular concentration of <a href="Adenosine_triphosphate" title="Adenosine triphosphate">ATP</a> is also diminished by pyocyanin causing further damage to <a href="Cystic_fibrosis_transmembrane_conductance_regulator" title="Cystic fibrosis transmembrane conductance regulator">CFTR</a> which are already impaired in cystic fibrosis. CFTR channels rely on ATP for two main purposes. Firstly, the binding and hydrolysis of ATP has to occur at two nucleotide binding domains for the channel to move between its open and closed conformation.<sup id="cite_ref-18" class="reference"><a href="#cite_note-18"><span class="cite-bracket">[</span>18<span class="cite-bracket">]</span></a></sup> Secondly, phosphorylation of CFTR by <a href="Protein_kinase_A" title="Protein kinase A">Protein kinase A</a> should occur in order for the channel to be operational. PKA is activated by cAMP which is produced from ATP. Both these processes are impaired when ATP is depleted by pyocyanin.

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<div class="mw-heading mw-heading2"><h2 id="Defence_against_pyocyanin">Defence against pyocyanin</h2></div>

<p><i><a href="Caenorhabditis_elegans" title="Caenorhabditis elegans">Caenorhabditis elegans</a></i> possesses two specific <a href="ABC_transporter" title="ABC transporter">ABC transporters</a> called <i>pgp-1</i> and <i>pgp-2</i> which are effectively able to extrude intracellular pyocyanin in an energy dependent manner.<sup id="cite_ref-19" class="reference"><a href="#cite_note-19"><span class="cite-bracket">[</span>19<span class="cite-bracket">]</span></a></sup>

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<ul><li><i><a href="Pseudomonas_Aeruginosa" class="mw-redirect" title="Pseudomonas Aeruginosa">Pseudomonas aeruginosa</a></i></li>

<li><a href="Pyoverdine" title="Pyoverdine">Pyoverdine</a></li>

<li><a href="Cystic_fibrosis" title="Cystic fibrosis">Cystic fibrosis</a></li></ul>

<div class="mw-heading mw-heading2"><h2 id="References">References</h2></div>

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<li id="cite_note-1"><span class="mw-cite-backlink"><b><a href="#cite_ref-1">^</a></b></span> <span class="reference-text"><a rel="nofollow" class="external text" href="http://www.sigmaaldrich.com/catalog/ProductDetail.do?lang=en&N4=P0046%7CSIGMA&N5=SEARCH_CONCAT_PNO%7CBRAND_KEY&F=SPEC">Pyocyanin</a> at <a href="Sigma-Aldrich" title="Sigma-Aldrich">Sigma-Aldrich</a></span>

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</style><cite id="CITEREFHassanFridovich1980" class="citation journal cs1">Hassan H, Fridovich I (1980). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC293551">"Mechanism of the antibiotic action pyocyanine"</a>. <i><a href="Journal_of_Bacteriology" title="Journal of Bacteriology">Journal of Bacteriology</a></i>. <b>141</b> (1): <span class="nowrap">156–</span>163. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FJB.141.1.156-163.1980">10.1128/JB.141.1.156-163.1980</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC293551">293551</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/6243619">6243619</a>.</cite></span>

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<li id="cite_note-3"><span class="mw-cite-backlink"><b><a href="#cite_ref-3">^</a></b></span> <span class="reference-text"><cite id="CITEREFLauHassettRanKong2004" class="citation journal cs1">Lau G, Hassett D, Ran H, Kong F (2004). "The role of pyocyanin in Pseudomonas aeruginosa infection". <i><a href="Trends_in_Molecular_Medicine" class="mw-redirect" title="Trends in Molecular Medicine">Trends in Molecular Medicine</a></i>. <b>10</b> (12): <span class="nowrap">1–</span>666. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.molmed.2004.10.002">10.1016/j.molmed.2004.10.002</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/15567330">15567330</a>.</cite></span>

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<li id="cite_note-4"><span class="mw-cite-backlink"><b><a href="#cite_ref-4">^</a></b></span> <span class="reference-text"><cite id="CITEREFBritiginRailsbackCox1999" class="citation journal cs1">Britigin B, Railsback A, Cox D (1999). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC96448">"The <i>Pseudomonas aeruginosa</i> secretory product pyocyanin inactivates α1 protease inhibitor: implications for the pathogenesis of cystic fibrosis lung disease"</a>. <i><a href="Infection_and_Immunity" title="Infection and Immunity">Infection and Immunity</a></i>. <b>67</b> (3): <span class="nowrap">1207–</span>1212. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FIAI.67.3.1207-1212.1999">10.1128/IAI.67.3.1207-1212.1999</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC96448">96448</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/10024562">10024562</a>.</cite></span>

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<li id="cite_note-MavrodiBonsall2001-5"><span class="mw-cite-backlink">^ <a href="#cite_ref-MavrodiBonsall2001_5-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-MavrodiBonsall2001_5-1"><sup><i><b>b</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFMavrodiBonsallDelaneySoule2001" class="citation journal cs1">Mavrodi, D. V.; Bonsall, R. F.; Delaney, S. M.; Soule, M. J.; Phillips, G.; Thomashow, L. S. (2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC100142">"Functional Analysis of Genes for Biosynthesis of Pyocyanin and Phenazine-1-Carboxamide from Pseudomonas aeruginosa PAO1"</a>. <i>Journal of Bacteriology</i>. <b>183</b> (21): <span class="nowrap">6454–</span>6465. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FJB.183.21.6454-6465.2001">10.1128/JB.183.21.6454-6465.2001</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0021-9193">0021-9193</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC100142">100142</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11591691">11591691</a>.</cite></span>

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<li id="cite_note-BlankenfeldtParsons2014-6"><span class="mw-cite-backlink">^ <a href="#cite_ref-BlankenfeldtParsons2014_6-0"><sup><i><b>a</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-1"><sup><i><b>b</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-2"><sup><i><b>c</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-3"><sup><i><b>d</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-4"><sup><i><b>e</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-5"><sup><i><b>f</b></i></sup></a> <a href="#cite_ref-BlankenfeldtParsons2014_6-6"><sup><i><b>g</b></i></sup></a></span> <span class="reference-text"><cite id="CITEREFBlankenfeldtParsons2014" class="citation journal cs1">Blankenfeldt, Wulf; Parsons, James F (2014). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4268259">"The structural biology of phenazine biosynthesis"</a>. <i>Current Opinion in Structural Biology</i>. <b>29</b>: <span class="nowrap">26–</span>33. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2Fj.sbi.2014.08.013">10.1016/j.sbi.2014.08.013</a>. <a href="ISSN_(identifier)" class="mw-redirect" title="ISSN (identifier)">ISSN</a> <a rel="nofollow" class="external text" href="https://search.worldcat.org/issn/0959-440X">0959-440X</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4268259">4268259</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/25215885">25215885</a>.</cite></span>

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<li id="cite_note-7"><span class="mw-cite-backlink"><b><a href="#cite_ref-7">^</a></b></span> <span class="reference-text"><cite id="CITEREFMavrodi_D,_Bonsall,_R,_Delaney,_S,_Soule,_M,_Phillips_G_&_Thomashow,_L._S.2001" class="citation journal cs1">Mavrodi D, Bonsall, R, Delaney, S, Soule, M, Phillips G & Thomashow, L. S. (2001). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC100142">"Function analysis of genes for biosynthesis of pyocyanin and phenazine -1-carboxamide from <i>Pseudomonas aeruginosa</i> PAO1"</a>. <i><a href="Journal_of_Bacteriology" title="Journal of Bacteriology">Journal of Bacteriology</a></i>. <b>183</b> (21): <span class="nowrap">6454–</span>6465. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FJB.183.21.6454-6465.2001">10.1128/JB.183.21.6454-6465.2001</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC100142">100142</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/11591691">11591691</a>.</cite><span class="cs1-maint citation-comment"><code class="cs1-code">{{cite journal}}</code>: CS1 maint: multiple names: authors list (link)</span></span>

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<li id="cite_note-8"><span class="mw-cite-backlink"><b><a href="#cite_ref-8">^</a></b></span> <span class="reference-text"><cite id="CITEREFDenningIyerReszkaO'Malley2003" class="citation journal cs1">Denning G, Iyer S, Reszka K, O'Malley Y, Rasmussen G, Britigan B (2003). "Phenazine-1-carboxylic acid, a secondary metabolite of Pseudomonas aeruginosa, alters expression of immunomodulatory proteins by human airway epithelial cells". <i><a href="American_Journal_of_Physiology" title="American Journal of Physiology">American Journal of Physiology</a></i>. <b>285</b> (3): 584–L592. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1152%2Fajplung.00086.2003">10.1152/ajplung.00086.2003</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12765878">12765878</a>.</cite></span>

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<li id="cite_note-9"><span class="mw-cite-backlink"><b><a href="#cite_ref-9">^</a></b></span> <span class="reference-text"><cite id="CITEREFMuller_M2002" class="citation journal cs1">Muller M (2002). "Pyocyanin inducesoxidative stress in human endothelialcells and modulates the glutathione redox cycle". <i><a href="Free_Radical_Biology_and_Medicine" title="Free Radical Biology and Medicine">Free Radical Biology and Medicine</a></i>. <b>33</b> (11): <span class="nowrap">1527–</span>1533. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0891-5849%2802%2901087-0">10.1016/S0891-5849(02)01087-0</a>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/12446210">12446210</a>.</cite></span>

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<cite id="CITEREFHuimin_R,_Hassett_DLau_G2003" class="citation journal cs1">Huimin R, Hassett D & Lau G (2003). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC283589">"Human targets of <i>Pseudomonas aeruginosa</i> pyocyanin"</a>. <i><a href="PNAS" class="mw-redirect" title="PNAS">PNAS</a></i>. <b>100</b> (24): <span class="nowrap">14315–</span>14320. <a href="Bibcode_(identifier)" class="mw-redirect" title="Bibcode (identifier)">Bibcode</a>:<a rel="nofollow" class="external text" href="https://ui.adsabs.harvard.edu/abs/2003PNAS..10014315R">2003PNAS..10014315R</a>. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1073%2Fpnas.2332354100">10.1073/pnas.2332354100</a></span>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC283589">283589</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/14605211">14605211</a>.</cite></span>

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<li id="cite_note-11"><span class="mw-cite-backlink"><b><a href="#cite_ref-11">^</a></b></span> <span class="reference-text"><cite id="CITEREFHoHirataUmemotaOhya1993" class="citation journal cs1">Ho M, Hirata R, Umemota N, Ohya Y, Takatsuki A, Stevens T, Anraku Y (1993). <a rel="nofollow" class="external text" href="http://www.jbc.org/content/268/24/18286.long">"VMA13 encodes a 54-kDa vacuolar H(+)ATPase subunit required for activity but not assembly of the enzyme complex in <i>Saccharomyces cerevisiae</i>"</a>. <i><a href="The_Journal_of_Biological_Chemistry" class="mw-redirect" title="The Journal of Biological Chemistry">The Journal of Biological Chemistry</a></i>. <b>268</b> (24): <span class="nowrap">18286–</span>18292. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://doi.org/10.1016%2FS0021-9258%2817%2946842-6">10.1016/S0021-9258(17)46842-6</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8349704">8349704</a>.</cite></span>

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<li id="cite_note-12"><span class="mw-cite-backlink"><b><a href="#cite_ref-12">^</a></b></span> <span class="reference-text"><cite id="CITEREFHassettWoodruffWozniakVasil1993" class="citation journal cs1">Hassett D, Woodruff W, Wozniak D, Vasil M, Cohen S, Ohman D (1993). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC206923">"Cloning and characterization of the <i>Pseudomonas aeruginosa</i> soda and sodB genes encoding manganese- and iron cofactored SOD: demonstration of increased Mn SOD dismutase activity in alginate-producing bacteria"</a>. <i><a href="Journal_of_Bacteriology" title="Journal of Bacteriology">Journal of Bacteriology</a></i>. <b>175</b> (23): <span class="nowrap">7658–</span>65. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2Fjb.175.23.7658-7665.1993">10.1128/jb.175.23.7658-7665.1993</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC206923">206923</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8244935">8244935</a>.</cite></span>

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<li id="cite_note-13"><span class="mw-cite-backlink"><b><a href="#cite_ref-13">^</a></b></span> <span class="reference-text"><cite id="CITEREFSorensenKlinger1987" class="citation book cs1">Sorensen R, Klinger J (1987). "Biological Effects of Pseudomonas aeruginosa Phenazine Pigments". <i>Basic Research and Clinical Aspects of Pseudomonas Aeruginosa</i>. Antibiotics and Chemotherapy. Vol. 39. pp. <span class="nowrap">113–</span>124. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1159%2F000414339">10.1159/000414339</a>. <a href="ISBN_(identifier)" class="mw-redirect" title="ISBN (identifier)">ISBN</a> <bdi>978-3-8055-4541-9</bdi>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/3118778">3118778</a>.</cite> <span class="cs1-visible-error citation-comment"><code class="cs1-code">{{cite book}}</code>: </span><span class="cs1-visible-error citation-comment"><code class="cs1-code">|journal=</code> ignored (help)</span></span>

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<li id="cite_note-14"><span class="mw-cite-backlink"><b><a href="#cite_ref-14">^</a></b></span> <span class="reference-text"><cite id="CITEREFKanthakumarTaylorTsangCundell1993" class="citation journal cs1">Kanthakumar K, Taylor G, Tsang K, Cundell D, Rutman A, Smith S, Jeffery P, Cole P, Wilson R (1993). <a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC280930">"Mechanism of action of <i>Pseudomona aeruginosa</i> pyocyanin on human ciliary beat in vitro"</a>. <i><a href="Infection_and_Immunity" title="Infection and Immunity">Infection and Immunity</a></i>. <b>61</b> (7): <span class="nowrap">2848–</span>2853. <a href="Doi_(identifier)" class="mw-redirect" title="Doi (identifier)">doi</a>:<a rel="nofollow" class="external text" href="https://doi.org/10.1128%2FIAI.61.7.2848-2853.1993">10.1128/IAI.61.7.2848-2853.1993</a>. <a href="PMC_(identifier)" class="mw-redirect" title="PMC (identifier)">PMC</a> <span class="id-lock-free" title="Freely accessible"><a rel="nofollow" class="external text" href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC280930">280930</a></span>. <a href="PMID_(identifier)" class="mw-redirect" title="PMID (identifier)">PMID</a> <a rel="nofollow" class="external text" href="https://pubmed.ncbi.nlm.nih.gov/8390405">8390405</a>.</cite></span>

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<ul><li><a rel="nofollow" class="external text" href="http://www.caymanchem.com/app/template/Product.vm/catalog/10009594">Pyocyanin profile</a></li></ul></div><div><div class="zim-footer">

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