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Key Documents

P0103

Sigma-Aldrich

Prodigiosin

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

Sinonimo/i:

2,2′-Bi-1H-Pyrrole,4-methoxy-5-[(5-methyl-4-pentyl-2H-pyrrol-2-ylidene)methyl, 2-Methyl-3-amyl-6-methoxyprodigiosene

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About This Item

Formula empirica (notazione di Hill):
C20H25N3O · HCl
Numero CAS:
Peso molecolare:
359.89
Codice UNSPSC:
12352200
NACRES:
NA.32

Origine biologica

Serratia marcescens

Livello qualitativo

Saggio

≥98% (HPLC)

Forma fisica

powder

Solubilità

DMSO: soluble
H2O: insoluble
acetonitrile: soluble
chloroform: soluble
methanol: soluble

Condizioni di spedizione

wet ice

Temperatura di conservazione

−20°C

Descrizione generale

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

Azioni biochim/fisiol

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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T-cell specific immunosuppression by prodigiosin isolated from Serratia marcescens.
Han SB
International Journal of Immunopharmacology, 20(1-3), 1-13 (1998)
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
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
Purification and characterization of prodigiosin produced by integrated bioreactor from Serratia sp. KH-95.
Song MJ
Journal of Bioscience and Bioengineering, 101(2), 157-161 (2006)
The prodigiosins, proapoptotic drugs with anticancer properties.
Perez-Tomas R
Biochemical Pharmacology, 66(8), 1447-1452 (2003)

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