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529685

Prodigiosin Serratia marcescens

Name: Prodigiosin <i>Serratia marcescens</i>
Brand: MM

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

Synonym(s):

Prodigiosin Serratia marcescens, Casein Kinase I Inhibitor IV, 2-Methyl-3-pentyl-6-methoxyprodigiosene, NSC 47147

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About This Item

Empirical Formula (Hill Notation):

C₂₀H₂₅N₃O

CAS Number:

82-89-3

Molecular Weight:

323.43

UNSPSC Code:

12352200

NACRES:

NA.77

Quality Level

100

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

SMILES string

CC1=C(CCCCC)C=C(/C=C2N=C(C3=CC=CN3)C=C\2OC)N1

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 p21^WAF/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

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

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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’.

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Bacterial Pigment Prodigiosin Demonstrates a Unique Antiherpesvirus Activity That Is Mediated through Inhibition of Prosurvival Signal Transducers.

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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