Skip to Content
Merck
All Photos(1)

Documents

Safety Information

P0103

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C20H25N3O · HCl
CAS Number:
56144-17-3
Molecular Weight:
359.89
UNSPSC Code:
12352200
NACRES:
NA.32

biological source

Serratia marcescens

Quality Level

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

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

P0103-100UG-PW:
P0103-100UG:
P0103-VAR:
P0103-BULK:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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)
Daniel P Roberts et al.
AMB Express, 11(1), 10-10 (2021-01-08)
Ethanol extract of cell mass of Serratia marcescens strain N4-5, when applied as a treatment to cucumber seed, has been shown to provide control of the oomycete soil-borne plant pathogen Pythium ultimum equivalent to that provided by a seed-treatment chemical
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.
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)
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service