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

• ChemBase编号: 129186
• 分子式: C13H10N2O
• 平均质量: 210.2313
• 单一同位素质量: 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

名称和登记号

名称

• IUPAC标准名: 5-methyl-1,5-dihydrophenazin-1-one
• IUPAC传统名: pyocyanine
• 别名: Pyocyanin; Pyrocyanine; 5-Methyl-1(5H)-phenazinone; Sanasin; Sanazin; Pyocyanine; Pyocyanin, Ready Made Solution from Pseudomonas aeruginosa; 5-Methyl-1(5H)-phenazinone; Pyocyanine; Pyocyanin

登记号

• CAS号: 85-66-5
• MDL号: MFCD01794662
• PubChem SID: 162223483
• PubChem CID: 6817
• 维基百科标题: Pyocyanine

理论计算性质

• 极化性: 23.191843 Å^3
• 极化表面积: 32.67 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true
• 质子受体: 3
• 质子供体: 0
• LogD (pH = 5.5): 2.4985068
• LogD (pH = 7.4): 2.498515
• Log P: 2.498515
• 摩尔折射率: 68.0593 cm^3

分子性质

理化性质

• 溶解度: acetone: soluble; chloroform: soluble; DMSO: soluble; ethanol: soluble
• 外观: DMSO solution; Solid; solid

安全信息

• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 1
• 危险公开号: 22-41
• 安全公开号: 26-39
• GHS危险品标识: GHS05; GHS07
• GHS警示词: Danger
• GHS危险声明: H302-H318
• GHS警示性声明: P280-P305 + P351 + P338
• 保存温度: -20°C

产品相关信息

• 纯度: ≥98% (HPLC)
• 浓度: 5 mg/mL (in 20% DMSO)
• 生物来源: from Pseudomonas aeruginosa
• 无菌消毒: sterile; 0.2 μm filtered
• 运输包装: dry ice; wet ice
• Empirical Formula (Hill Notation): C13H10N2O

详细说明

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.