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P0046

Sigma-Aldrich

Pyocyanin

from Pseudomonas aeruginosa, ≥98% (HPLC), solid, redox-active phenazine

Synonym(s):

5-Methyl-1(5H)-phenazinone, Pyocyanine, Sanasin, Sanazin

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About This Item

Empirical Formula (Hill Notation):
C13H10N2O
CAS Number:
85-66-5
Molecular Weight:
210.23
MDL number:
MFCD01794662
UNSPSC Code:
12352200
PubChem Substance ID:
329819996
NACRES:
NA.77

product name

Pyocyanin, from Pseudomonas aeruginosa, ≥98% (HPLC)

biological source

Pseudomonas aeruginosa

Quality Level

200

Assay

≥98% (HPLC)

form

solid

solubility

DMSO: soluble
acetone: soluble
chloroform: soluble
ethanol: soluble

shipped in

wet ice

storage temp.

−20°C

SMILES string

CN1c2ccccc2N=C3C(=O)C=CC=C13

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

InChI key

YNCMLFHHXWETLD-UHFFFAOYSA-N

Application

Pyocyanin has been used as a biomarker to detect Pseudomonas aeruginosa.

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.

Preparation Note

For the preparation of an aqueous solution, dissolve pyocyanin in ethanol using 10% of the final required volume and then add distilled water to complete the volume.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Mout De Vrieze et al.
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Pf prophages are ssDNA filamentous prophages that are prevalent among various Pseudomonas aeruginosa strains. The genomes of Pf prophages contain not only core genes encoding functions involved in phage replication, structure and assembly but also accessory genes. By studying the
Fast selective detection of pyocyanin using cyclic voltammetry
Alatraktchi F, et al.
Sensors, 16(3), 408-408 (2016)
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PloS one, 7(5), e38148-e38148 (2012-06-06)
The opportunistic pathogen Pseudomonas aeruginosa responds to zinc, cadmium and cobalt by way of the CzcRS two-component system. In presence of these metals the regulatory protein CzcR induces the expression of the CzcCBA efflux pump, expelling and thereby inducing resistance
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