Millipore Sigma Vibrant Logo

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.

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, GF 109203X, Gö 6850

Primary Target: PKC
View Products on Sigmaaldrich.com
203290
View Pricing & Availability

Overview

Replacement Information

Key Spec Table

CAS #Empirical Formula
133052-90-1C₂₅H₂₄N₄O₂

Pricing & Availability

Catalogue Number AvailabilityPackaging Qty/Pack Price Quantity
203290-1MGCN
Retrieving availability...
—
Limited Availability Limited Availability
In Stock 
Discontinued
Limited Quantities Available
Availability to be confirmed
    Remaining : Will advise
      Remaining : Will advise
      Will advise
      Contact Customer Service
      Contact Customer Service

      		 Plastic ampoule 1 mg
      Retrieving price...
      Price could not be retrieved
      Minimum Quantity is a multiple of
      Maximum Quantity is
      Upon Order Completion More Information
      You Saved ()
       
      —
      Request Pricing
      		 —
      203290-250UGCN
      Retrieving availability...
      —
      Limited Availability Limited Availability
      In Stock 
      Discontinued
      Limited Quantities Available
      Availability to be confirmed
        Remaining : Will advise
          Remaining : Will advise
          Will advise
          Contact Customer Service
          Contact Customer Service

          		 Plastic ampoule 250 μg
          Retrieving price...
          Price could not be retrieved
          Minimum Quantity is a multiple of
          Maximum Quantity is
          Upon Order Completion More Information
          You Saved ()
           
          —
          Request Pricing
          		 —
          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, GF 109203X, Gö 6850
          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
          203290-1MGCN 04055977221121
          203290-250UGCN 07790788048327

          Documentation

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

          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, GF 109203X, Gö 6850
          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.
          		•