529685

Sigma-Aldrich

Prodigiosin Serratia marcescens - CAS 82-89-3 - Calbiochem

A cell-permeable tripyrrole alkaloid compound that displays immunosuppressive and anti-tumor properties irrespective of p53 status and multidrug resistance.

Synonym(s):
Casein Kinase I Inhibitor IV, 2-Methyl-3-pentyl-6-methoxyprodigiosene, NSC 47147, Prodigiosin Serratia marcescens - CAS 82-89-3 - Calbiochem
Empirical Formula (Hill Notation):
C20H25N3O
CAS Number:
Molecular Weight:
323.43

storage conditions

-20C

Quality Level

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

dark red

solubility

DMF: soluble
DMSO: soluble
ethanol: soluble
methanol: soluble

shipped in

ambient

storage temp.

−20°C

InChI

1S/C20H25N3O/c1-4-5-6-8-15-11-16(22-14(15)2)12-19-20(24-3)13-18(23-19)17-9-7-10-21-17/h7,9-13,22-23H,4-6,8H2,1-3H3/b18-17+,19-12+

InChI key

WKGQSEFBQTWRPT-FHUUTLRSSA-N

General description

A cell-permeable tripyrrole alkaloid compound that displays immunosuppressive and anti-tumor properties irrespective of p53 status and multidrug resistance. Shown to selectively upregulate p21WAF/CIP1 and NAG-1 (nonsteroidal anti-inflammatory drug-activated gene 1) and downregulate survivin expression levels, induce mitochondria-mediated apoptosis and cell cycle arrest in tumor cells. Prevents FADD phosphorylation (IC50 = 2.0 µM in A549-FKR cells) through inhibition of FADD-kinase CK1α (IC50 ~ 6.0 µM in SW620-BGCR cells) and augments cisplatin (Cat. No. 232120)-induced apoptosis. Blocks NF-κB activation by decreasing pIκBα (by 63% at 3 µM) and IκBα levels in A549 cells, and shrinks tumor growth in A549-FKR tumor xenograft mouse model (3 mg/kg, i.p., o.d.).

Packaging

200 μg in Glass bottle
Packaged under inert gas

Warning

Toxicity: Standard Handling (A)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.

Other Notes

Schinske, K.A., et al. 2011. Mol. Cancer Ther.10, 1807.
Chang, C.C., et al. 2011. J. Biosci. Bioeng.5, 501
Ho, T.F., et al. 2009. Toxicol. Appl. Pharmacol.235, 253
Soto-Cerrato, V., et al. 2007.Mol. Cancer Ther.6, 362.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Rahul K Suryawanshi et al.
Journal of virology, 94(13) (2020-04-17)
Herpes simplex virus (HSV) is among the most prevalent viral infections worldwide and remains incurable. While nucleoside analogs are used to relieve symptoms of infection, they suffer from having serious adverse effects and are unable to abolish the virus from...

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