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

203290
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      Empirical FormulaCAS #
      C₂₅H₂₄N₄O₂ 133052-90-1

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      203290-1MG
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          Ampoule plast. 1 mg
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          203290-250UG
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              Ampoule plast. 250 μg
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              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
              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

              Documentation

              FDS

              Titre

              Fiche de données de sécurité des matériaux (FDS) 

              Certificats d'analyse

              TitreNuméro de lot
              203290

              Références bibliographiques

              Aperçu de la référence bibliographique
              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

              Titre
            • 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.
            • Fiche technique

              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 +2°C to +8°C
              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.
              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.