P0103

Prodigiosin hydrochloride

from Serratia marcescens, ≥98% (HPLC), powder

• Synonym(s): 2,2′-Bi-1H-Pyrrole,4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl, 2-Methyl-3-amyl-6-methoxyprodigiosene hydrochloride
• Empirical Formula (Hill Notation): C₂₀H₂₅N₃O · HCl
• CAS Number: 56144-17-3
• Molecular Weight: 359.89
• NACRES: NA.32
• UNSPSC Code: 12352200

Properties

• biological source: Serratia marcescens
• Quality Segment: 200
• assay: ≥98% (HPLC)
• form: powder
• solubility: DMSO: soluble, H₂O: insoluble, acetonitrile: soluble, chloroform: soluble, methanol: soluble
• shipped in: wet ice
• storage temp.: −20°C

Description

General description

Prodigiosin is a red pigment with common pyrrolyl pyrromethene skeleton and is biosynthesized by Serratia marcescens and other bacteria.

Biochem/physiol Actions

Prodigiosin (PG) exhibits antibacterial, anticancer, cytotoxic, immunosuppressive and antiproliferative activities. Prodigiosin stimulates apoptosis in hematopoietic cancer cells and in cells derived from other human cancers, such as gastric and colon, with no marked toxicity in nonmalignant cell lines. In addition, prodigiosin also has p53-independent anti-proliferative activity. Experimental studies show that prodigiosin promotes various cellular processes such as cell shrinkage, chromatin condensation, restructuring of actin microfilament network and detachment of cells from the cell culture substrate. Different targets and mechanisms of action were described for prodigiosin, including induction of single- and double stranded DNA breaks modulation of pH, regulation of mitogen-activated protein kinase, and inhibition of cell cycle progression.

Prodigiosin, a tripyrrole red pigment biosynthesized by Serratia marcescens and other bacteria, exhibits antibacterial, anticancer, cytotoxic, immunosuppressive, and antiproliferative activities. Prodigiosin induces apoptosis in hematopoietic cancer cells and cells derived from other human cancers, including gastric and colon with no marked toxicity in nonmalignant cell lines. Morphological analysis of prodigiosin-treated cells demonstrated that prodigiosin induces cell shrinkage, chromatin condensation, reorganization of actin microfilament architecture, and detachment of cells from the cell culture substrate. Different targets and mechanisms of action are described for prodigiosin, including induction of single- and double-strand DNA breaks, modulation of pH, regulation of mitogen-activated protein kinase, and inhibition of cell cycle progression.

Prodigiosin, a tripyrrole red pigment biosynthesized by Serratia marcescens and other bacteria, induces apoptosis and exhibits antibacterial, anticancer, cytotoxic, immunosuppressive, and antiproliferative activities.

Safety Information

• Storage Class: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point (°F): Not applicable
• Flash Point (°C): Not applicable
• PPE (personal protective equipment): Eyeshields, Gloves, type N95 (US)