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Merck

P0103

Sigma-Aldrich

Prodigiosin hydrochloride

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

Sinónimos:

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

Fórmula empírica (notación de Hill):
C20H25N3O · HCl
Número de CAS:
Peso molecular:
359.89
Código UNSPSC:
12352200
NACRES:
NA.32

origen biológico

Serratia marcescens

Nivel de calidad

Análisis

≥98% (HPLC)

formulario

powder

solubilidad

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

Condiciones de envío

wet ice

temp. de almacenamiento

−20°C

Descripción general

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

Acciones bioquímicas o fisiológicas

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.

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type N95 (US)


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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.
The prodigiosins, proapoptotic drugs with anticancer properties.
Perez-Tomas R
Biochemical Pharmacology, 66(8), 1447-1452 (2003)

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