Pyocyanine
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| Category | Antibiotics |
| Catalog number | BBF-01746 |
| CAS | 85-66-5 |
| Molecular Weight | 210.23 |
| Molecular Formula | C13H10N2O |
| Purity | ≥98% |
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Description
It is produced by the strain of Streptomyces cyanoflavus. It has anti-gram positive bacteria, negative bacteria (weak) and mycobacterium (weak) activity. It has been shown to accelerate neutrophil apoptosis in vitro, resulting in resolution of acute inflammation, which is beneficial for bacterial survival.
Specification
| Synonyms | Antibiotic 4738-B; Cyanomycin; Pyrocyanine; Sanazin; 5-methylphenazin-1(5H)-one; 5-methylphenazin-5-ium-1-olate |
| Storage | -20 °C |
| IUPAC Name | 5-methylphenazin-1-one |
| Canonical SMILES | CN1C2=CC=CC=C2N=C3C1=CC=CC3=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 |
| InChI Key | YNCMLFHHXWETLD-UHFFFAOYSA-N |
Properties
| Appearance | Dark Blue Acicular Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; Mycobacteria |
| Boiling Point | 403.3 °C at 760 mmHg |
| Melting Point | 128 °C (dec.) |
| Density | 1.24 g/cm3 |
| Solubility | Soluble in DMSO, Hydrochloric acid, sodium hydroxide |
Reference Reading
1. Roles of Two-Component Systems in Pseudomonas aeruginosa Virulence
Maria Sultan, Rekha Arya, Kyeong Kyu Kim Int J Mol Sci . 2021 Nov 10;22(22):12152. doi: 10.3390/ijms222212152.
Pseudomonas aeruginosais an opportunistic pathogen that synthesizes and secretes a wide range of virulence factors.P. aeruginosaposes a potential threat to human health worldwide due to its omnipresent nature, robust host accumulation, high virulence, and significant resistance to multiple antibiotics. The pathogenicity ofP. aeruginosa, which is associated with acute and chronic infections, is linked with multiple virulence factors and associated secretion systems, such as the ability to form and utilize a biofilm, pili, flagella, alginate, pyocyanin, proteases, and toxins. Two-component systems (TCSs) ofP. aeruginosaperform an essential role in controlling virulence factors in response to internal and external stimuli. Therefore, understanding the mechanism of TCSs to perceive and respond to signals from the environment and control the production of virulence factors during infection is essential to understanding the diseases caused byP. aeruginosainfection and further develop new antibiotics to treat this pathogen. This review discusses the important virulence factors ofP. aeruginosaand the understanding of their regulation through TCSs by focusing on biofilm, motility, pyocyanin, and cytotoxins.
2. [The physiologic role of pyocyanine synthesized by Pseudomonas aeruginosa]
A D Garagulia, E A Kiprianova, S M Trutko, V K Akimenko Mikrobiologiia . 1988 Nov-Dec;57(6):957-64.
The physiological role of pyocyanine for Pseudomonas aeruginosa was studied. Its synthesis was shown to commence at the retardation growth phase. Pyocyanine was accumulated only in the growth medium. The addition of 2,6-dichlorophenolindophenol accepting the reducing equivalents from coenzyme Q and transferring them to cytochrome c inhibited the pigment accumulation. This was indicative of the connection between pyocyanine synthesis and the level of the reducing equivalents in the cells. Pyocyanine did not accept the reducing equivalents from coenzyme Q in the respiratory chain of P. aeruginosa. Only reduced pyridine nucleotides served as substrates for pyocyanine in the reaction of autooxidation. The kinetic parameters of this reaction and the affinity of NADH dehydrogenase for the substrate were measured. The kinetic data were analysed to show that, under the physiological conditions, pyocyanine could not apparently compete with the respiratory chain for the reducing equivalents and hence directly regulate the level of NAD(P)H in P. aeruginosa cells. In order to keep the oxidising activity at a level necessary for the cells, the latter decreased the content of the reducing equivalents either by synthesizing pyocyanine or owing to the activity of cyanide-resistant oxidase. These processes of releasing the reducing equivalents are in a reciprocal relationship.
3. In vitro effect of synthetic pyocyanine on neutrophil superoxide production
R U Sorensen, D G Dearborn, K M Miller Infect Immun . 1987 Mar;55(3):559-63. doi: 10.1128/iai.55.3.559-563.1987.
Pyocyanine, a low-molecular-weight phenazine pigment produced by Pseudomonas aeruginosa, has previously been shown to strongly inhibit human lymphocyte blastogenesis. We now report that synthetic pyocyanine can also affect the generation of superoxide by human peripheral blood polymorphonuclear leukocytes (PMNs) in a dose-dependent manner. Superoxide production by PMNs stimulated with phorbol myristate acetate (PMA) was measured in the presence and absence of pyocyanine, phenazine, and trifluoperazine, a phenothiazine of similar chemical structure to the phenazine pigments. Pyocyanine at 50 microM inhibited superoxide production to 28.9 +/- 2.8% of PMA control values, whereas at the lower concentration of 1 microM, the production of superoxide was significantly enhanced (203 +/- 31.7% of PMA control values). Phenazine, the tricyclic parent compound of pyocyanine, had only a minor effect. Trifluoperazine had a marked inhibitory effect on superoxide generation at concentrations above 1 microM. None of the compounds induced superoxide generation in the absence of PMA. Pyocyanine at all concentrations, unlike phenothiazines, had very little effect on the release of neutrophil granule enzymes. The effect of P. aeruginosa phenazine pigments on polymorphonuclear phagocytes is of significance, since inhibition of host PMN function at sites of infection could result in ineffective bacterial killing, whereas enhanced PMN function could lead to greater tissue damage. These two possibilities are not mutually exclusive and may coexist depending on local pyocyanine concentrations.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
