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529685

Prodigiosin Serratia marcescens

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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Size/SKUAvailabilityPrice
200 μg
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$205.00

About This Item

Empirical Formula (Hill Notation):
C20H25N3O
CAS Number:
Molecular Weight:
323.43
NACRES:
NA.77
UNSPSC Code:
12352200
Assay:
≥95% (HPLC)
Form:
solid
Storage condition:
OK to freeze, protect from light

$205.00


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Quality Segment

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 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

Packaged under inert gas

Preparation Note

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

Disclaimer

Toxicity: Standard Handling (A)

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description

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

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form

solid

form

solid

form

waxy solid

form

solid

assay

≥95% (HPLC)

assay

≥95% (HPLC)

assay

≥98% (TLC)

assay

≥90% (HPLC)

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

manufacturer/tradename

Calbiochem®

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

−20°C

storage condition

OK to freeze, protect from light

storage condition

OK to freeze

storage condition

OK to freeze

storage condition

OK to freeze


Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable



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