A P. aeruginosa virulence factor
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1-Hydroxyphenazine

Item No. 28064

Technical Information
Formal Name
1-phenazinol
CAS Number
528-71-2
Synonyms
  • Hemipyocyanine
  • NSC 88882
Molecular Formula
C12H8N2O
Formula Weight
Purity
≥98%
A crystalline solid
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 1 mg/ml
λmax
264, 369 nm
SMILES
OC1=CC=CC2=C1N=C(C=CC=C3)C3=N2
InChi Code
InChI=1S/C12H8N2O/c15-11-7-3-6-10-12(11)14-9-5-2-1-4-8(9)13-10/h1-7,15H
InChi Key
SVRNCBGWUMMBQB-UHFFFAOYSA-N
Origin
Synthetic
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    1-Hydroxyphenazine is a phenazine pigment and virulence factor produced by P. aeruginosa.1,2 It increases production of reactive oxygen species (ROS) in RAW 264.7 cells in a concentration-dependent manner.2 1-Hydroxyphenazine (≥1.55 and ≥3.12 μM) increases release of elastase and myeloperoxidase (MPO), respectively, by human neutrophils activated with N-formyl-L-methionyl-L-leucyl-L-phenylalanine (fMLP; Item No. 21495) and cytochalasin B (Item No. 11328).1 It reduces ciliary beat frequency in isolated guinea pig tracheal rings, resulting in ciliary dyskinesia by 1 hour when used at concentrations of 10, 50, and 100 μM and ciliary stasis by 5 hours at 50 and 100 μM.3 1-Hydroxyphenazine reduces tracheal mucus velocity in anesthetized guinea pigs when administered as a 100 or 200 ng bolus dose. It is also active against the plant pathogenic fungi F. graminearum, P. grisea, A. solani, F. oxysporium, and S. sclerotiorum (MICs = 2-50 μg/ml).4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Ramafi, G., Anderson, R., Theron, A., et al. Exposure of N-formyl-L-methionyl-L-leucyl-L-phenylalanine-activated human neutrophils to the Pseudomonas aeruginosa-derived pigment 1-hydroxyphenazine is associated with impaired calcium efflux and potentiation of primary granule enzyme release. Infect. Immun. 67(10), 5157-5162 (1999).

    2. Sinha, S., Shen, X., Gallazzi, F., et al. Generation of reactive oxygen species mediated by 1‑hydroxyphenazine, a virulence factor of Pseudomonas aeruginosa. Chem. Res. Toxicol. 28(2), 175-181 (2015).

    3. Munro, N.C., Barker, A., Rutman, A., et al. Effect of pyocyanin and 1-hydroxyphenazine on in vivo tracheal mucus velocity. J. Appl. Physiol. 67(1), 316-323 (1985).

    4. Luo, Q., Hu, H., Peng, H., et al. Isolation and structural identification of two bioactive phenazines from Streptomyces griseoluteus P510. Chin. J. Chem. Eng. 23(4), 699-703 (2015).