PYOCYANINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H10N2O
Molecular Weight	210.2313
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C2=CC=CC(=O)C2=NC3=C1C=CC=C3

InChI

InChIKey=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

HIDE SMILES / InChI

Molecular Formula	C13H10N2O
Molecular Weight	210.2313
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

PubMed

Title	Date	PubMed
Analysis of quorum sensing-dependent virulence factor production and its relationship with antimicrobial susceptibility in Pseudomonas aeruginosa respiratory isolates.	2010-12	20132256
Lactoferrin-derived peptides and Lactoferricin chimera inhibit virulence factor production and biofilm formation in Pseudomonas aeruginosa.	2010-10	20477900
Design, synthesis and antibacterial activity of novel andrographolide derivatives.	2010-06-15	20493714
Transcriptomic analysis reveals a global alkyl-quinolone-independent regulatory role for PqsE in facilitating the environmental adaptation of Pseudomonas aeruginosa to plant and animal hosts.	2010-06	20406282
Metabolism and function of phenazines in bacteria: impacts on the behavior of bacteria in the environment and biotechnological processes.	2010-05	20352425
Quenching of singlet oxygen by pyocyanin and related phenazines.	2010-04-23	20408986
The Pseudomonas aeruginosa oxidative stress regulator OxyR influences production of pyocyanin and rhamnolipids: protective role of pyocyanin.	2010-03	19926657
Production of rhamnolipid biosurfactants by Pseudomonas aeruginosa DS10-129 in a microfluidic bioreactor.	2010-02-02	19958287
Editorial: Maintaining the balance--fishing for drugs to treat persistent neutrophilic inflammation.	2010-02	20123680
Pivotal Advance: Pharmacological manipulation of inflammation resolution during spontaneously resolving tissue neutrophilia in the zebrafish.	2010-02	19850882
Approaching intelligent infection diagnostics: Carbon fibre sensor for electrochemical pyocyanin detection.	2010-02	19666245
Paraoxonase 2 is down-regulated by the Pseudomonas aeruginosa quorumsensing signal N-(3-oxododecanoyl)-L-homoserine lactone and attenuates oxidative stress induced by pyocyanin.	2010-01-27	19925453
Reduced expression of virulence factors in multidrug-resistant Pseudomonas aeruginosa strains.	2010-01	19960337
Pseudomonas aeruginosa exotoxin pyocyanin causes cystic fibrosis airway pathogenesis.	2009-12	19893030
Endogenous nitric oxide protects bacteria against a wide spectrum of antibiotics.	2009-09-11	19745150
The neuroendocrine hormone norepinephrine increases Pseudomonas aeruginosa PA14 virulence through the las quorum-sensing pathway.	2009-09	19517106
Subinhibitory concentrations of the cationic antimicrobial peptide colistin induce the pseudomonas quinolone signal in Pseudomonas aeruginosa.	2009-09	19477905
Polyphenol cytotoxicity induced by the bacterial toxin pyocyanin: role of NQO1.	2009-07-01	19362588
A strand-specific RNA-Seq analysis of the transcriptome of the typhoid bacillus Salmonella typhi.	2009-07	19609351
Synthesis and evaluation of antibacterial activities of andrographolide analogues.	2009-07	19152987
Pseudomonas pyocyanin inhibits wound repair by inducing premature cellular senescence: role for p38 mitogen-activated protein kinase.	2009-06	19286324
Electrochemical analysis of quorum sensing inhibition.	2009-05-28	19436882
HD-GYP domain proteins regulate biofilm formation and virulence in Pseudomonas aeruginosa.	2009-05	19170727
Revisiting the quorum-sensing hierarchy in Pseudomonas aeruginosa: the transcriptional regulator RhlR regulates LasR-specific factors.	2009-03	19246742
Development of a simple and low cost microbioreactor for high-throughput bioprocessing.	2009-02	18854953
The role of the cytoplasmic heme-binding protein (PhuS) of Pseudomonas aeruginosa in intracellular heme trafficking and iron homeostasis.	2009-01-02	18990702
The role of quorum sensing in chronic cystic fibrosis Pseudomonas aeruginosa infections.	2009-01	19016870
Pseudomonas aeruginosa and the hyperlipidaemia of sepsis.	2009	20001339
Pseudomonas aeruginosa PAO1 preferentially grows as aggregates in liquid batch cultures and disperses upon starvation.	2009	19436737
Redox warfare between airway epithelial cells and Pseudomonas: dual oxidase versus pyocyanin.	2009	18979077
Oxidative stress caused by pyocyanin impairs CFTR Cl(-) transport in human bronchial epithelial cells.	2008-12-15	18845244
Liver sinusoidal endothelial cells and acute non-oxidative hepatic injury induced by Pseudomonas aeruginosa pyocyanin.	2008-12	19134050
Rsd family proteins make simultaneous interactions with regions 2 and 4 of the primary sigma factor.	2008-12	18826409
Exploring antagonistic metabolites of established biocontrol agent of marine origin.	2008-12	18626581
Community organizers and (bio)filmmaking.	2008-11	18936747
Solenopsin A, a venom alkaloid from the fire ant Solenopsis invicta, inhibits quorum-sensing signaling in Pseudomonas aeruginosa.	2008-10-15	18713055
Redox-independent activation of NF-kappaB by Pseudomonas aeruginosa pyocyanin in a cystic fibrosis airway epithelial cell line.	2008-10-03	18682396
The Pseudomonas toxin pyocyanin inhibits the dual oxidase-based antimicrobial system as it imposes oxidative stress on airway epithelial cells.	2008-10-01	18802092
The PA4204 gene encodes a periplasmic gluconolactonase (PpgL) which is important for fitness of Pseudomonas aeruginosa.	2008-10	18832304
Modulation of secreted virulence factor genes by subinhibitory concentrations of antibiotics in Pseudomonas aeruginosa.	2008-08	18758736
Depletion of intestinal phosphate after operative injury activates the virulence of P aeruginosa causing lethal gut-derived sepsis.	2008-08	18656625
Potassium and sodium transporters of Pseudomonas aeruginosa regulate virulence to barley.	2008-07	18481058
Crystal structure of the pyocyanin biosynthetic protein PhzS.	2008-05-13	18416536
Quorum-sensing activity and related virulence factor expression in clinically pathogenic isolates of Pseudomonas aeruginosa.	2008-04	18190582
Curcumin, a known phenolic from Curcuma longa, attenuates the virulence of Pseudomonas aeruginosa PAO1 in whole plant and animal pathogenicity models.	2008-03-26	18284200
Subversion of a lysosomal pathway regulating neutrophil apoptosis by a major bacterial toxin, pyocyanin.	2008-03-01	18292577
Use of the lambda Red recombinase system to rapidly generate mutants in Pseudomonas aeruginosa.	2008-02-04	18248677
Multiple phenotypic alterations caused by a c-type cytochrome maturation ccmC gene mutation in Pseudomonas aeruginosa.	2008-01	18174132
Inactivation of pyocyanin synthesis genes has no effect on the virulence of Pseudomonas aeruginosa PAO1 toward the silkworm, Bombyx mori.	2008-01	18031534
Reactions of Pseudomonas aeruginosa pyocyanin with reduced glutathione.	2008	18797520

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:21:55 GMT 2025` Edited by `admin` on `Mon Mar 31 21:21:55 GMT 2025`
Record UNII	9OQM399341
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-400612

Preferred Name

English

PYOCYANINE

Common Name

English

SANASIN

Common Name

English

PYOCYANINE [MI]

Common Name

English

5-METHYL-1(5H)-PHENAZINONE

Systematic Name

English

PYOCYANIN

Common Name

English

SANAZIN

Common Name

English

Code System Code Type Description

CHEBI

8653