Structure via PubChem · Public domain (PubChem)
pyocyanine
Sign in to savePyocyanin (PCN−) is one of the many toxic compounds produced and secreted by the Gram negative bacterium Pseudomonas aeruginosa. Pyocyanin is a blue secondary metabolite, turning red below pH 4.9, with the ability to oxidise and reduce other molecules and therefore kill microbes competing against P. aeruginosa as well as mammalian cells of the lungs which P. aeruginosa has infected during cystic fibrosis. Since pyocyanin is a zwitterion at blood pH, it is easily able to cross the cell membrane. There are three different states in which pyocyanin can exist: oxidized (blue), monovalently reduced
Chemical data
- Formula
- C13H10N2O
- Molecular weight
- 210.23 g/mol
- IUPAC name
- 5-methylphenazin-1-one
- SMILES
- CN1C2=CC=CC=C2N=C3C1=CC=CC3=O
- InChIKey
- YNCMLFHHXWETLD-UHFFFAOYSA-N
- XLogP
- 2
- Polar surface area
- 32.7 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
2,030 papers- Pseudomonas aeruginosa's greenish-blue pigment pyocyanin: its production and biological activities.Microbial cell factories · 2023
- Simplified Flow Photosynthesis of Deuterium-Labeled Pyocyanin.Journal of labelled compounds & radiopharmaceuticals · 2024
- Modulation of pulmonary immune functions by the Pseudomonas aeruginosa secondary metabolite pyocyanin.Frontiers in immunology · 2025
- Sodium houttuyfonate, a potential phytoanticipin derivative of antibacterial agent, inhibits bacterial attachment and pyocyanine secretion of Pseudomonas aeruginosa by attenuating flagella-mediated swimming motility.World journal of microbiology & biotechnology · 2013
- Pyocyanin Modulates Gastrointestinal Transformation and Microbiota.Journal of agricultural and food chemistry · 2022
via PubMed
Wikidata facts
- Mass
- 210.079
Show 4 more facts
- chemical formula
- C₁₃H₁₀N₂O
- canonical SMILES
- CN1C2=CC=CC=C2N=C3C1=CC=CC3=O
- found in taxon
- Pseudomonas aeruginosa
- Commons category
- Pyocyanin
via Wikidata · CC0
~8 min read
Encyclopedic overview
8 sectionsContents
- Biosynthesis
- Redox warfare
- Targets
- Cystic fibrosis
- Defence against pyocyanin
- See also
- References
- External links
Pyocyanin (PCN−) is one of the many toxic compounds produced and secreted by the Gram negative bacterium Pseudomonas aeruginosa. Pyocyanin is a blue secondary metabolite, turning red below pH 4.9, with the ability to oxidise and reduce other molecules and therefore kill microbes competing against P. aeruginosa as well as mammalian cells of the lungs which P. aeruginosa has infected during cystic fibrosis. Since pyocyanin is a zwitterion at blood pH, it is easily able to cross the cell membrane. There are three different states in which pyocyanin can exist: oxidized (blue), monovalently reduced (colourless) or divalently reduced (red). Mitochondria play an important role in the cycling of pyocyanin between its redox states. Due to its redox-active properties, pyocyanin generates reactive oxygen species.
==Biosynthesis==
Excerpted from Wikipedia’s “pyocyanine” article, available under the CC BY-SA 4.0 licence.