Pyocyanin

Item № 10009594
CAS № 85-66-5
Purity ≥98%
SIZE PRICE QUANTITY SUBTOTAL
CART TOTAL $0.00
5 mg $68.00 0.00
10 mg $129.00 0.00
50 mg $435.00 0.00
100 mg $734.00 0.00

Pricing updated 2018-02-18. Prices are subject to change without notice.

Description
Synonyms
  • Sanasin
  • Sanazin
  • Pyocyanine

Pseudomonas aeruginosa (P. aeruginosa) is a common pathogen affecting immunocompromised patients with acute diseases such as pneumonia and vasculitis or chronic diseases such as cystic fibrosis. It produces several phenazine toxic metabolites, the most predominant of which is a blue pigment, pyocyanin. Pyocyanin, which can reach concentrations of 100 µM in cystic fibrosis patients infected with P. aeruginosa, activates the aryl hydrocarbon receptor with a Ki value of 5.4 µM.1 This induces the expression of both detoxifying enzymes, resulting in pyocyanin degradation, and cytokines that facilitate the clearance of bacteria.1 Pyocyanin has been shown to accelerate neutrophil apoptosis in vitro, resulting in resolution of acute inflammation, which is beneficial for bacterial survival. It also induces a 10-fold acceleration of neutrophil apoptosis in vivo.2 Pyocyanin production results in reduced bacterial clearance from the lungs of immunocompromised patients. It has also been reported to induce apoptosis in human lung epithelial cells and to induce premature cellular senescence in mammalian cells.3 Pyocyanin undergoes nonenzymatic reduction by NADPH, which produces hydrogen peroxide and depletes intracellular glutathione levels, causing oxidative stress in susceptible cells.4

Recommended Products

Related Products
View Related Product Categories
View Screening Libraries with Pyocyanin
Technical Information
Formal Name
5-methyl-1(5H)-phenazinone
CAS Number
85-66-5
Synonyms
  • Sanasin
  • Sanazin
  • Pyocyanine
Molecular Formula
C13H10N2O
Formula Weight
210.2
Purity
≥98%
Formulation
A crystalline solid
λmax
238, 322, 720 nm
SMILES
Cn1c2ccccc2nc2c(=O)cccc12
InChI Code
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

Warning - this product is not for human or veterinary use.

Shipping & Storage
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Stability
≥ 2 years
Downloads & Resources
Product Downloads

Download Product Insert

Download Safety Data Sheet (SDS)

Download free InChI Key generation software

Additional Information

View the Cayman Structure Database for chemical structure definitions for many Cayman products

Get Batch-Specific Data and Documents by Batch Number

Provide batch numbers separated by commas to download or request available product inserts, QC sheets, certificates of analysis, data pack, and GC-MS data.

References & Product Citations
Product Description References

1. Moura-Alves, P.,Faé, K.,Houthuys, E., et al. AhR sensing of bacterial pigments regulates antibacterial defence. Nature 512(7515), 387-392 (2014).

2. Allen, L.,Dockrell, D.H.,Pattery, T., et al. Pyocyanin production by Pseudomonas aeruginosa induces neutrophil apoptosis and impairs neutrophil-mediated host defenses in vivo. Journal of Immunology 174, 3643-3649 (2005).

3. Muller, M. Premature cellular senescence induced by pyocyanin, a redox-active Pseudomonas aeruginosa toxin. Free Radical Biology & Medicine 41, 1670-1677 (2006).

4. Muller, M. Pyocyanin induces oxidative stress in human endothelial cells and modulates the glutathione redox cycle. Free Radical Biology & Medicine 33(11), 1527-1533 (2002).

Technical Support
Contact Us
  • Toll Free Phone (USA and Canada Only): (888) 526-5351
  • Direct Phone: (734) 975-3888
Contract Research Services

We work with scientists to support their research, drug discovery, and drug development needs through our expertise in the following research services:

Cayman Chemical

1180 East Ellsworth Road

Ann Arbor, Michigan 48108 USA

Toll Free: (800) 364-9897

(USA and Canada Only)

Fax: (734) 971-3640