56144-17-3

56144-17-3 structure
56144-17-3 structure
  • Name: Prodigiosin hydrochloride
  • Chemical Name: 2,​2'-​Bi-​1H-​pyrrole, 4-​methoxy-​5-​[(5-​methyl-​4-​pentyl-​2H-​pyrrol-​2-​ylidene)​methyl]​-​, hydrochloride (1:1)
  • CAS Number: 56144-17-3
  • Molecular Formula: C20H26ClN3O
  • Molecular Weight: 359.89300
  • Catalog: Signaling Pathways Anti-infection Bacterial
  • Create Date: 2017-05-21 11:59:36
  • Modify Date: 2024-01-06 13:44:51
  • Prodigiosin (Prodigiosine) hydrochloride is a red pigment produced by bacteria as a bioactive secondary metabolite. Prodigiosin hydrochloride is a potent proapoptotic agent, and inhibits Wnt/β-catenin pathway. Prodigiosin hydrochloride has antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive, and anticancer properties[1][2].

Name 2,​2'-​Bi-​1H-​pyrrole, 4-​methoxy-​5-​[(5-​methyl-​4-​pentyl-​2H-​pyrrol-​2-​ylidene)​methyl]​-​, hydrochloride (1:1)
Description Prodigiosin (Prodigiosine) hydrochloride is a red pigment produced by bacteria as a bioactive secondary metabolite. Prodigiosin hydrochloride is a potent proapoptotic agent, and inhibits Wnt/β-catenin pathway. Prodigiosin hydrochloride has antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive, and anticancer properties[1][2].
Related Catalog
In Vitro Prodigiosin (25-500 nM; 24 hours) treatment reduces the viability of breast cancer cells, with IC50 values at 48 h of 62.52 nM in MDA-MB-231 cells and 261.2 nM in MDA-MB-468 cells[1]. 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[1]. Prodigiosin can inhibit proliferation and induce apoptosis in breast cancer cells[1]. 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[1]. 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[2]. Cell Proliferation Assay[1] 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 IC50 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[1] 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.
In Vivo 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[1]. Animal Model: Female BALB/c nude mice injected with MDA-MB-231 cells[1] Dosage: 5 mg/kg Administration: Intraperitoneal injection; twice weekly; for 3 weeks Result: Significantly inhibited tumor growth in mice.
References

[1]. Wang Z, et al. Prodigiosin inhibits Wnt/β-catenin signaling and exerts anticancer activity in breast cancer cells. Proc Natl Acad Sci U S A. 2016 Nov 15;113(46):13150-13155.

[2]. Woodhams DC, et al. Prodigiosin, Violacein, and Volatile Organic Compounds Produced by Widespread Cutaneous Bacteria of Amphibians Can Inhibit Two Batrachochytrium Fungal Pathogens. Microb Ecol. 2018 May;75(4):1049-1062.

Molecular Formula C20H26ClN3O
Molecular Weight 359.89300
Exact Mass 359.17600
PSA 53.17000
LogP 5.57810
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
RIDADR NONH for all modes of transport