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Merck

R9532

Pyocyanin

≥98% (HPLC), oxidative metabolism enhancer, DMSO solution

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C13H10N2O
Número CAS:
Peso molecular:
210.23
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Nombre del producto

Pyocyanin, Ready Made Solution from Pseudomonas aeruginosa, 5 mg/mL in DMSO

SMILES string

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

InChI key

YNCMLFHHXWETLD-UHFFFAOYSA-N

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

assay

≥98% (HPLC)

form

DMSO solution

concentration

5 mg/mL in DMSO

shipped in

dry ice

storage temp.

−20°C

Quality Level

Categorías relacionadas

Application

Pyocyanin has been used:
  • To disable the ability of forkhead box A2 (FOXA2) to regulate goblet cell hyperplasia and metaplasia (GCHM) and mucin expression.
  • To activate 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.
  • To stimulate Pseudomonas aeruginosa PAO1 cell line adhesion and invasion in human lung carcinoma A549 cells via reactive oxygen species (ROS) production.

Biochem/physiol Actions

Pyocyanin, a redox-active phenazine, is an electron receptor, which stimulates redox cycling in bacteria, liver cells, and human epithlial cell lines.
Pyocyanin, a redox-active phenazine, is an electron receptor, which stimulates redox cycling in bacteria, liver cells, and human epithlial cell lines. It enhances oxidative metabolism, which increases the formation of intracellular reactive oxygen species (ROS) via reduction of NADPH. Pyocyanin also increases the release of the neutrophil chemoattractant IL-8 by airway epithelial cells both in vitro and in vivo. This involves signal transduction pathways that include oxidants, protein tyrosin kinases and MAP-kinases. IL-8 secretion by these cells is in synergy with inflammatory cytokines. Pyocyanin accelerates neutrophil apoptosis in vitro. Mice infected with a pyocyanin-deficient strain of P. aeruginosa showed elevated levels of neutrophils and neutrophil chemokines and cytokines, as well as compromised bacterial clearance from the lungs compared with mice infected with a wild type strain. This suggests that pyocyanin production by P. aeruginosa suppresses the acute inflammatory response by pathogen-driven acceleration of neutrophil apoptosis and by reducing local inflammation, and that this is advantageous for bacterial survival.

General description

Pyocyanin is a secondary metabolite, which is produced by Pseudomonas aeruginosa.

Clase de almacenamiento

10 - Combustible liquids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable


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Pyocyanin-induced mucin production is associated with redox modification of FOXA2
Hao Y, et al.
Respiratory Research, 14(1), 82-82 (2013)
Pseudomonas aeruginosa pyocyanin activates NRF2-ARE-mediated transcriptional response via the ROS-EGFR-PI3K-AKT/MEK-ERK MAP kinase signaling in pulmonary epithelial cells
Xu Y, et al.
PLoS ONE, 8(8), e72528-e72528 (2013)
Nuclear protein HMGN2 attenuates pyocyanin-induced oxidative stress via Nrf2 signaling and inhibits Pseudomonas aeruginosa internalization in A549 cells
Liu K, et al.
Free Radical Biology & Medicine, 108(8), 404-417 (2017)
M V Kuznetsova et al.
Zhurnal mikrobiologii, epidemiologii, i immunobiologii, (6)(6), 17-22 (2013-01-10)
Study the effect of P. aeruginosa exometabolites on planktonic and biofilm cultures of bioluminescent E. coli strain. E. coli K12 TG1 (pF1 lux+ Ap(r)) recombinant bioluminescent strain, P. aeruginosa ATCC 27853 reference strain and 2 nosocomial isolates were used. Pyocyanin
Justin E Culbertson et al.
Biochimica et biophysica acta, 1834(1), 240-246 (2012-10-27)
PhzE from Pseudomonas aeruginosa catalyzes the first step in the biosynthesis of phenazine-1-carboxylic acid, pyocyanin, and other phenazines, which are virulence factors for Pseudomonas species. The reaction catalyzed converts chorismate into aminodeoxyisochorismate using ammonia supplied by a glutamine amidotransferase domain.

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