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203290

Sigma-Aldrich

Bisindolylmaleimide I

A highly selective, cell-permeable, and reversible protein kinase C (PKC) inhibitor (IC₅₀ = 10 nM) that is structurally similar to staurosporine.

Synonym(s):

Bisindolylmaleimide I, 2-[1-(3-Dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide, Gö 6850, GF 109203X

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About This Item

Empirical Formula (Hill Notation):
C25H24N4O2
CAS Number:
133052-90-1
Molecular Weight:
412.48
MDL number:
MFCD00236428
UNSPSC Code:
12352111
NACRES:
NA.77

Quality Level

100

Assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

deep orange

solubility

DMSO: 10 mg/mL

shipped in

ambient

storage temp.

2-8°C

InChI

1S/C25H24N4O2/c1-28(2)12-7-13-29-15-19(17-9-4-6-11-21(17)29)23-22(24(30)27-25(23)31)18-14-26-20-10-5-3-8-16(18)20/h3-6,8-11,14-15,26H,7,12-13H2,1-2H3,(H,27,30,31)

InChI key

QMGUOJYZJKLOLH-UHFFFAOYSA-N

General description

A highly selective cell-permeable protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine. Acts as a competitive inhibitor for the ATP-binding site of PKC. Shows high selectivity for PKCα, βI, βII, γ, δ, and ε isozymes. May inhibit protein kinase A at a much higher concentration (IC50 = 2 µM). Also inhibits telomerase activity in quercetin, H-89, or herbimycin A treated NPC-076 cells.
A highly selective, cell-permeable, and reversible protein kinase C (PKC) inhibitor (IC50 = 10 nM) that is structurally similar to staurosporine. Acts as a competitive inhibitor for the ATP-binding site of PKC. Shows high selectivity for PKCα-, βI-, βII-, γ-, δ-, and ε- isozymes. Potently inhibits GSK-3 in primary adipocyte lysates (IC50 = 360 nM) and in GSK-3β immunoprecipitates (IC50 = 170 nM). May inhibit protein kinase A at a much higher concentration (IC50 = 2 µM). A 1 mg/ml solution of Bisindolylmaleimide I (Cat. No. 203293) in anhydrous DMSO is also available.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
PKC
Product competes with ATP.
Reversible: yes
Target IC50: 10 nM against protein kinase C (PKC); 360 nM, 170 nM against GSK-3 in primary adipocyte lysates and in GSK-3β immunoprecipitates, respectively

Warning

Toxicity: Standard Handling (A)

Preparation Note

Further dilute with aqueous buffers just prior to use.

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.

Other Notes

Hers, I., et al. 1999. FEBS Lett.460, 433.
Ku, W.-C., et al. 1997. Biochem. Biophys. Res. Commun. 241, 730.
Gekeler, V., et al. 1996. Br. J. Cancer 74, 897.
Kiss, Z., et al. 1995. Biochim. Biophys. Acta 1265, 93.
Toullec, D., et al. 1991. J. Biol. Chem. 266, 15771.

Legal Information

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Certificates of Analysis (COA)

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Biology of the cell, 106(1), 30-43 (2013-11-02)
Heterotrimeric GTP-binding proteins play a key role in cell trafficking regulation. Above all, specific Gβγ subunits have been shown to be a major component of a signal transduction pathway, which also involves phospholipases C (PLC), protein kinases C (PKC) and
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Extracellular agonists linked to inositol-1,4,5-trisphosphate (IP3) formation elicit cytosolic Ca2+ oscillations in many cell types, but despite a common signaling pathway, distinct agonist-specific Ca2+ spike patterns are observed. Using qPCR, we show that rat hepatocytes express multiple purinergic P2Y and
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Medicinal mushrooms of the genus Hericium are known to produce secondary metabolites with homeostatic properties for the central nervous system. We and others have recently demonstrated that among these metabolites cyathane diterpenoids and in particular erinacine C possess potent neurotrophin
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