P0046

Sigma-Aldrich

Pyocyanin

from Pseudomonas aeruginosa, ≥98% (HPLC)

Synonym(s):
Sanasin, Pyocyanine, 5-Methyl-1(5H)-phenazinone, Sanazin
Empirical Formula (Hill Notation):
C13H10N2O
CAS Number:
Molecular Weight:
210.23
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

biological source

Pseudomonas aeruginosa

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

Signal Word

Warning

Hazard Statements

hazcat

Acute Tox. 4 Oral - Eye Irrit. 2

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Pseudomonas aeruginosa Can Be Detected in a Polymicrobial Competition Model Using Impedance
Ward AC, et al.
PLoS ONE, 9(3), e91732-e91732 (2014)
Electrochemical sensing of biomarker for diagnostics of bacteria-specific infections
Alatraktchi F, et al.
Nanomedicine (London, England), 11(16), 2185-2195 (2016)
Fast selective detection of pyocyanin using cyclic voltammetry
Alatraktchi F, et al.
Sensors, 16(3), 408-408 (2016)
Theerthankar Das et al.
Frontiers in microbiology, 8, 2429-2429 (2018-01-10)
Pyocyanin secreted by
Mariola Andrejko et al.
Acta biochimica Polonica, 66(1), 91-100 (2019-03-05)
Thermally induced unfolding and renaturation capability of alkaline proteases (AprA) of three Pseudomonas aeruginosa strains, i.e. ATCC 27853 and two clinical isolates, was examined. Sequence analyses demonstrated a high level of aprA genes identity (99.24-99.8%) in these bacterial strains. The...
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