203290

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

Properties

• 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

Description

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, β_I, β_II, 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-, β_I-, β_II-, 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

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3