Prodigiosin

Prodigiosin (Prodigiosine) is a red pigment produced by bacteria as a bioactive secondary metabolite. Prodigiosin is a potent inhibitor of the Wnt/β-catenin pathway. Prodigiosin has antibacterial, antifungal, antiprotozoal, antimalarial, immunosuppressive, and anticancer properties.

Product information

CAS Number: 82-89-3

Molecular Weight: 323.43

Formula: C20H25N3O

Synonym:

Prodigiosine

Chemical Name: 4-methoxy-5-{[(2E)-5-methyl-4-pentyl-2H-pyrrol-2-ylidene]methyl}-1H, 1'H-2, 2'-bipyrrole

Smiles: CC1=N/C(=C/C2NC(=CC=2OC)C2=CC=CN2)/C=C1CCCCC

InChiKey: SZXDNGVQRDTJSD-FOWTUZBSSA-N

InChi: InChI=1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,21,23H,4-6,8H2,1-3H3/b16-12+

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Soluble in DMSO

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. 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.

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.

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.

Products are for research use only. Not for human use.