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
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About This Item
Empirical Formula (Hill Notation):
C20H25N3O · HCl
CAS Number:
Molecular Weight:
359.89
UNSPSC Code:
12352200
NACRES:
NA.32
Recommended Products
biological source
Serratia marcescens
Quality Level
Assay
≥98% (HPLC)
form
powder
solubility
DMSO: soluble
H2O: insoluble
acetonitrile: soluble
chloroform: soluble
methanol: soluble
shipped in
wet ice
storage temp.
−20°C
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.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Prodigiosin induces cell death and morphological changes indicative of apoptosis in gastric cancer cell line HGT-1.
Histology and Histopathology, 16(2), 415-421 (2001)
The prodigiosins, proapoptotic drugs with anticancer properties.
Perez-Tomas R
Biochemical Pharmacology, 66(8), 1447-1452 (2003)
Prodigiosin from the supernatant of Serratia marcescens induces apoptosis in haematopoietic cancer cell lines.
Montaner B
British Journal of Pharmacology, 131(3), 585-593 (2000)
Jacob M C Shaffer et al.
Frontiers in microbiology, 14, 1156033-1156033 (2023-05-30)
The McMurdo Dry Valleys of Antarctica experience a range of selective pressures, including extreme seasonal variation in temperature, water and nutrient availability, and UV radiation. Microbial mats in this ecosystem harbor dense concentrations of biomass in an otherwise desolate environment.
Beatriz Montaner et al.
Annals of the New York Academy of Sciences, 973, 246-249 (2002-12-18)
Prodigiosin (PG) is an active component of bacterial origin, with reported apoptotic effects. We examined the activation of caspases-9, -8, and -3 in PG-treated Jurkat cells in a dose-response study. These caspases were activated in apoptotic cells, as judged by
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