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82-89-3

中文名称 灵菌红素
英文名称 PRODIGIOSIN
CAS 82-89-3
分子式 C20H25N3O
分子量 323.43
MOL 文件 82-89-3.mol
更新日期 2024/01/27 15:20:22
82-89-3 结构式 82-89-3 结构式

基本信息

中文别名
灵杆菌素
灵菌红素
英文别名
Nsc47147
Aids010622
Aids-010622
PRODIGIOSIN
Prodigiosine
2-Methyl-3-amyl-6-methoxyprodigiosene
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl], 2,2'bipyrrole
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrol]
4-Methoxy-5-(4-pentyl-5-methyl-2H-pyrrole-2-ylidenemethyl)-2,2'-bi[1H-pyrrole]
4-Methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl]-2,2'-bi[1H-pyrrole]

物理化学性质

熔点151-152°
沸点554.3±50.0 °C(Predicted)
密度1.12±0.1 g/cm3(Predicted)
储存条件-20C
溶解度Acetonitrile: Soluble; Ethanol: Soluble; Methanol: Soluble
酸度系数(pKa)17.09±0.50(Predicted)
形态暗红色固体
颜色深红

常见问题列表

生物活性
Prodigiosin (Prodigiosine),一种天然的红色素,是一种具有生物活性的次生代谢产物。Prodigiosin 是 Wnt/β-catenin 途径的有效抑制剂。Prodigiosin 具有抗菌,抗真菌,抗原生动物,抗疟疾,免疫抑制和抗癌特性。
体外研究

Prodigiosin (25-500 nM; 24 hours) treatment reduces the viability of breast cancer cells, with IC 50 values at 48 h of 62.52 nM in MDA-MB-231 cells and 261.2 nM in MDA-MB-468 cells.
Prodigiosin (25-500 nM; 24 hours) treatment significantly reduces the levels of phosphorylated LRP6 and DVL2, active β-catenin, and total β-catenin. Prodigiosin noticeably inhibits the phosphorylation of GSK3β at Ser9 in HEK293T cells, which is indicative of an increase in GSK3β activity.
Prodigiosin can inhibit proliferation and induce apoptosis in breast cancer cells.
Prodigiosin (25-500 nM; 24 hours) treatment dose-dependently blocks Wnt signaling activated by Wnt1, Wnt3, Wnt1/LRP6, Wnt3/LRP6, and Dishevelled 2 (DVL2) in transfected HEK293T cells. Prodigiosin treatment inhibits Wnt3A-CM-induced transcription in a dose-dependent manner. Prodigiosin inhibits transcription of the SuperTopFlash reporter activated by either Wnt transfection or Wnt3A treatment.
When applied to cultures of chytrid fungi Batrachochytrium dendrobatidis and B. salamandrivorans , Prodigiosin causes significant growth inhibition, with MIC values of 10 μM and 50 μM, respectively.

Cell Proliferation Assay

Cell Line: MDA-MB-231 and MDA-MB-468 cells
Concentration: 10 nM, 25 nM, 50 nM, 100 nM, 250 nM, 500 nM, 1000 nM, 2500 nM, 5000 nM
Incubation Time: 24 hours, 48 hours
Result: Reduced the viability of breast cancer cells, with IC 50 values at 48 h of 62.52 nM in MDA-MB-231 cells and 261.2 nM in MDA-MB-468 cells.

Western Blot Analysis

Cell Line: HEK293T cells
Concentration: 50 nM, 100 nM, 250 nM, 500 nM
Incubation Time: 24 hours
Result: Significantly reduced the levels of phosphorylated LRP6 and DVL2, active β-catenin, and total β-catenin.
体内研究

Prodigiosin (5 mg/kg; intraperitoneal injection; twice weekly; for 3 weeks) treatment significantly inhibits tumor growth. Prodigiosin treatment decreases tumor cell density and expression of the proliferation marker Ki-67.

Animal Model: Female BALB/c nude mice injected with MDA-MB-231 cells
Dosage: 5 mg/kg
Administration: Intraperitoneal injection; twice weekly; for 3 weeks
Result: Significantly inhibited tumor growth in mice.
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