5-methyl-1,5-dihydrophenazin-1-one

• ChemBase ID: 129186
• Molecular Formular: C13H10N2O
• Molecular Mass: 210.2313
• Monoisotopic Mass: 210.07931295
• SMILES: Cn1c2ccccc2nc2c1cccc2=O
• Canonical SMILES: Cn1c2ccccc2nc2c1cccc2=O
• InChI: 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
• InChIKey: YNCMLFHHXWETLD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-1,5-dihydrophenazin-1-one
• IUPAC Traditional name: pyocyanine
• Synonyms: Pyocyanin; Pyrocyanine; 5-Methyl-1(5H)-phenazinone; Sanasin; Sanazin; Pyocyanine; Pyocyanin, Ready Made Solution from Pseudomonas aeruginosa; 5-Methyl-1(5H)-phenazinone; Pyocyanine; Pyocyanin

Database IDs

• CAS Number: 85-66-5
• MDL Number: MFCD01794662
• PubChem SID: 162223483
• PubChem CID: 6817
• Wikipedia Title: Pyocyanine

CALCULATED PROPERTIES

• Polarizability: 23.191843 Å^3
• Polar Surface Area: 32.67 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 2.4985068
• LogD (pH = 7.4): 2.498515
• Log P: 2.498515
• Molar Refractivity: 68.0593 cm^3

PROPERTIES

Physical Property

• Solubility: acetone: soluble; chloroform: soluble; DMSO: soluble; ethanol: soluble
• Apperance: DMSO solution; Solid; solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 1
• Risk Statements: 22-41
• Safety Statements: 26-39
• GHS Pictograms: GHS05; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)
• Concentration: 5 mg/mL (in 20% DMSO)
• Biological Source: from Pseudomonas aeruginosa
• Sterility: sterile; 0.2 μm filtered
• Shipped in: dry ice; wet ice
• Empirical Formula (Hill Notation): C13H10N2O

DETAILS

Sigma Aldrich - P0046

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.
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.1,2,3 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.1,3,4 Pyocyanin has been shown to accelerate neutrophil apoptosis in vitro, resulting in resolution of acute inflammation, which is beneficial for bacteria survival.5

Sigma Aldrich - R9532

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. 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.