85-66-5 Usage
Description
Pyocyanine is a redox-active phenazine produced by P. aeruginosa and other pathogens, acting as an electron receptor that stimulates redox cycling in bacteria and various human cell lines. It enhances oxidative metabolism, leading to increased formation of intracellular reactive oxygen species (ROS) via the reduction of NADPH. Pyocyanine accelerates neutrophil apoptosis in vitro and suppresses the acute inflammatory response by pathogen-driven acceleration of neutrophil apoptosis and associated reduction of local inflammation.
Uses
Used in Pharmaceutical Applications:
Pyocyanine is used as a regulator to disable the ability of forkhead box A2 (FOXA2) in controlling goblet cell hyperplasia and metaplasia (GCHM) and mucin expression.
Used in Cellular Signaling:
Pyocyanine is used as an activator of nuclear factor (erythroid-derived 2)-like 2 (NRF2) through the reactive oxygen species (ROS)-inducible epidermal growth factor receptor (EGFR)-phosphoinositide 3-kinase (PI3K) cellular signal transduction pathway and its downstream effectors.
Used in Microbiology Research:
Pyocyanine is used to stimulate Pseudomonas aeruginosa PAO1 cell line adhesion and invasion in human lung carcinoma A549 cells via reactive oxygen species (ROS) production.
Used in Antibiotic Research:
Pyocyanine is used as an antibiotic accelerator of neutrophil apoptosis, which can potentially enhance the effectiveness of certain antibiotics in treating infections.
Biochem/physiol Actions
Pyocyanin, a blue-green pigment belonging to phenazine pigments, is a redox-active phenazine. Pyocyanin is an electron receptor, which stimulates redox cycling in bacteria, liver cells, and human epithlial cell lines. Pyocyanin enhances the oxidative metabolism, which in turn increases the formation of intracellular reactive oxygen species (ROS) via reduction of NADPH. Pyocyanin also increases the release of IL-8 by airway epithelial cells both in vitro and in vivo. This involves signal transduction pathways that include oxidants, protein tyrosine kinases, and MAP kinases. IL-8 secretion by these cells is in synergy with inflammatory cytokines. Pyocyanin has been shown to accelerate neutrophil apoptosis in vitro, resulting in resolution of acute inflammation, which is beneficial for bacteria survival.
Enzyme inhibitor
This natural pigment (FW = 210.24 g/mol), which has an antifungal activity, is a secretory agent produced by Pseudomonas aeruginosa (formerly P. pyocyanea and Bacillus pyocyaneus). It is a blue solid that is soluble in chloroform and pyridine generates reactive oxygen species, such as superoxide and hydrogen peroxide. Pyocyanine is slightly soluble in cold water and the aqueous blue solution can be decolorized under alkaline conditions upon the addition of glucose or sodium hydrosulfite. Target(s): catalase; cytochrome P450 leukotriene B4 w-oxidation; and diamine oxidase.
Purification Methods
It crystallises from H2O as dark blue needles. The picrate has m 190o (dec). [Beilstein 23 H 395, 23 I 59, 23 II 234, 23/8 V 395.]
References
1) Rada and Leto (2013),?Pyocyanin effects on respiratory epithelium: relevance in Pseudomonas Aeruginosa airway infections; Trends Microbiol.,?21?73
2) Reszka?et al. (2012),?Inactivation of the potent Pseudomonas aeruginosa cytotoxin pyocyanin by airway peroxidases and nitrite; Am. J. Physiol. Lung Cell Mol. Physiol.,?302?L1044
Check Digit Verification of cas no
The CAS Registry Mumber 85-66-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 5 respectively; the second part has 2 digits, 6 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 85-66:
(4*8)+(3*5)+(2*6)+(1*6)=65
65 % 10 = 5
So 85-66-5 is a valid CAS Registry Number.
InChI: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
85-66-5Relevant articles and documents
A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa
Mortzfeld, Frederik B.,Pietruszka, J?rg,Baxendale, Ian R.
, p. 5424 - 5433 (2019/06/13)
The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product have been facilitated by the use of flow chemistry techniques and immobilised reagents. Using these procedures gram quantities of pyocyanin were easily prepared in high yield and purity.
PHENAZINE DERIVATIVES AS ANTIMICROBIAL AGENTS
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Paragraph 00298-00301, (2015/07/15)
The present invention provides novel phenazine derivatives, such as compounds of Formula (I) and (II), and pharmaceutically acceptable salts thereof. The compounds of the invention are expected to be anitmicrobial agents and may act by a microbial warfare strategy (e.g., a reactive oxygen species (ROS)-based competition strategy). The present invention also provides pharmaceutical compositions, kits, uses, and methods that involve the compounds of the invention and may be useful in preventing or treating a microbial infection (e.g., a bacterial infection) in a subject, inhibiting the growth and/or reproduction of a microorganism (e.g., a bacterium), killing a microorganism (e.g., a bacterium), inhibiting the formation and/or growth of a biofilm, or reducing or clearing a biofilm.
