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203290 Bisindolylmaleimide I - CAS 133052-90-1 - Calbiochem

Bisindolylmaleimide I, CAS 133052-90-1, is a cell-permeable, highly selective, reversible inhibitor of protein kinase C (IC50 = 10 nM). Acts on the ATP-binding site of PKC.

Bisindolylmaleimide I - CAS 133052-90-1 - Calbiochem MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

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

Primary Target: PKC
203290
Purchase on Sigma-Aldrich

Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
133052-90-1C₂₅H₂₄N₄O₂

Products

Catalogue NumberPackaging Qty/Pack
203290-1MG Plastová ampulka 1 mg
203290-250UG Plastová ampulka 250 μg
Description
OverviewA 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.
Catalogue Number203290
Brand Family Calbiochem®
Synonyms2-[1-(3-Dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide, Gö 6850, GF 109203X
References
ReferencesHers, 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.
Product Information
CAS number133052-90-1
ATP CompetitiveY
FormDeep orange solid
Hill FormulaC₂₅H₂₄N₄O₂
Chemical formulaC₂₅H₂₄N₄O₂
ReversibleY
Structure formula ImageStructure formula Image
Quality LevelMQ100
Applications
ApplicationBisindolylmaleimide I, CAS 133052-90-1, is a cell-permeable, highly selective, reversible inhibitor of protein kinase C (IC50 = 10 nM). Acts on the ATP-binding site of PKC.
Biological Information
Primary TargetPKC
Primary Target IC<sub>50</sub>10 nM against protein kinase C (PKC); 360 nM, 170 nM against GSK-3 in primary adipocyte lysates and in GSK-3β immunoprecipitates, respectively
Purity≥95% by HPLC
Physicochemical Information
Cell permeableY
Dimensions
Materials Information
Toxicological Information
Safety Information according to GHS
Safety Information
Product Usage Statements
Storage and Shipping Information
Ship Code Ambient Temperature Only
Toxicity Standard Handling
Storage +2°C to +8°C
Protect from Light Protect from light
Do not freeze Ok to freeze
Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.
Packaging Information
Transport Information
Supplemental Information
Specifications
Global Trade Item Number
Catalogue Number GTIN
203290-1MG 04055977221121
203290-250UG 07790788048327

Documentation

Bisindolylmaleimide I - CAS 133052-90-1 - Calbiochem MSDS

Title

Safety Data Sheet (SDS) 

Bisindolylmaleimide I - CAS 133052-90-1 - Calbiochem Certificates of Analysis

TitleLot Number
203290

References

Reference overview
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.

Citations

Title
  • Alexandra Thiel, Mira Heinonen, Johanna Rintahaka, Tuija Hallikainen, and Annabrita Hemmes, Dan A. Dixon, Caj Haglund, and Ari Ristimaki. (2006) EXPRESSION OF CYCLOOXYGENASE-2 IS REGULATED BY GSK-3 IN GASTRIC CANCER CELLS. Journal of Biological Chemistry in press,.
  • Xiaohua Jiang, et al. (2005) Hyperhomocystinemia impairs endothelial function and eNOS activity via PKC activation. Arteriosclerosis, Thrombosis, and Vascular Biology in press,.
  • Ademi E. Santiago-Walker, et al. (2005) Protein Kinase C δ Stimulates Apoptosis by Initiating G1 Phase Cell Cycle Progression and S Phase Arrest. Journal of Biological Chemistry 280, 32107-32114.
  • Wojciech Wojciechowski, et al. (2005) Enhanced Expression of CD20 in Human Tumor B Cells is Controlled Through ERK-Dependent Mechanisms. Journal of Immunology 174, 7859-7868.
  • Justin C. Mason, et al. (2004) Decay-accelerating actor induction on vascular endothelium by vascular endothelial growth factor (VEGF) is mediated via a VEGF receptor-2 (VEGF-R2)- and protein kinase C-α/ε (PKCα/ε)-dependent cytoprotective signaling pathway a. Journal of Biological Chemistry 279, 41611-41618.
  • Michael J. Cross, et al. (2002) The Shb Adaptor Protein Binds to Tyrosine 766 in the FGFR-1 and Regulates the Ras/MEK/MAPK Pathway via FRS2 Phosphorylation in Endothelial Cells. Molecular Biology of the Cell 13, 2881-2893.
    		•
    Data Sheet

    Note that this data sheet is not lot-specific and is representative of the current specifications for this product. Please consult the vial label and the certificate of analysis for information on specific lots. Also note that shipping conditions may differ from storage conditions.

    Revision05-May-2010 RFH
    Synonyms2-[1-(3-Dimethylaminopropyl)-1H-indol-3-yl]-3-(1H-indol-3-yl)-maleimide, Gö 6850, GF 109203X
    DescriptionA 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.
    FormDeep orange solid
    CAS number133052-90-1
    Chemical formulaC₂₅H₂₄N₄O₂
    Structure formulaStructure formula
    Purity≥95% by HPLC
    SolubilityDMSO (10 mg/ml). Further dilute with aqueous buffers just prior to use.
    Storage Protect from light
    +2°C to +8°C
    Do Not Freeze Ok to freeze
    Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). DMSO stock solutions are stable for up to 4 months at -20°C.
    Toxicity Standard Handling
    ReferencesHers, 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.
    Citation
  • Alexandra Thiel, Mira Heinonen, Johanna Rintahaka, Tuija Hallikainen, and Annabrita Hemmes, Dan A. Dixon, Caj Haglund, and Ari Ristimaki. (2006) EXPRESSION OF CYCLOOXYGENASE-2 IS REGULATED BY GSK-3 IN GASTRIC CANCER CELLS. Journal of Biological Chemistry in press,.
  • Xiaohua Jiang, et al. (2005) Hyperhomocystinemia impairs endothelial function and eNOS activity via PKC activation. Arteriosclerosis, Thrombosis, and Vascular Biology in press,.
  • Ademi E. Santiago-Walker, et al. (2005) Protein Kinase C δ Stimulates Apoptosis by Initiating G1 Phase Cell Cycle Progression and S Phase Arrest. Journal of Biological Chemistry 280, 32107-32114.
  • Wojciech Wojciechowski, et al. (2005) Enhanced Expression of CD20 in Human Tumor B Cells is Controlled Through ERK-Dependent Mechanisms. Journal of Immunology 174, 7859-7868.
  • Justin C. Mason, et al. (2004) Decay-accelerating actor induction on vascular endothelium by vascular endothelial growth factor (VEGF) is mediated via a VEGF receptor-2 (VEGF-R2)- and protein kinase C-α/ε (PKCα/ε)-dependent cytoprotective signaling pathway a. Journal of Biological Chemistry 279, 41611-41618.
  • Michael J. Cross, et al. (2002) The Shb Adaptor Protein Binds to Tyrosine 766 in the FGFR-1 and Regulates the Ras/MEK/MAPK Pathway via FRS2 Phosphorylation in Endothelial Cells. Molecular Biology of the Cell 13, 2881-2893.
    		•