Prodigiosin hydrochloride

• CAT Number: I045703
• CAS Number: 56144-17-3
• Molecular Formula: C20H26ClN3O
• Molecular Weight: 359.89
• Purity: ≥95%
• Synonyms: (2E)-3-methoxy-2-[(5-methyl-4-pentyl-1H-pyrrol-2-yl)methylidene]-5-(1H-pyrrol-2-yl)pyrrole;hydrochloride
• InChI: InChI=1S/C20H25N3O.ClH/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;/h7,9-13,21-22H,4-6,8H2,1-3H3;1H/b19-12+
• InChIKey: UQRGJSTXVCWXNU-NNTHFVATSA-N
• SMILES: CCCCCC1=C(NC(=C1)C=C2C(=CC(=N2)C3=CC=CN3)OC)C.Cl

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].
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].
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].

Reference

[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.
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[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.
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