681675 Wortmannin - CAS 19545-26-7 - Calbiochem

Overview

Replacement Information

Key Specifications Table

Empirical FormulaCAS #
C₂₃H₂₄O₈ 19545-26-7

Pricing & Availability

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681675-1MG
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      Glass bottle 1 mg
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      Description
      OverviewA cell-permeable, fungal metabolite that acts as a potent, selective, and irreversible inhibitor of phosphatidylinositol 3-kinase in purified preparations and cytosolic fractions (IC50 = 5 nM). Blocks the catalytic activity of PI 3-kinase without affecting the upstream signaling events. Preincubation of fibroblasts with wortmannin abolishes PDGF-mediated Ins(3,4,5)P3 formation (IC50 = 5 nM). Also blocks the metabolic effects of insulin in isolated rat adipocytes without affecting the insulin receptor tyrosine kinase activity. Inhibits MAP kinase activation induced by platelet activating factor in guinea pig neutrophils (200 - 300 nM). Also inhibits other kinases such as myosin light chain kinase (IC50 = 200 nM) and PI 4-kinase at concentrations higher than that required for inhibition of PI 3-kinase. Also blocks phospholipase D. A 10 mM (1 mg/233 µl) solution of Wortmannin (Cat. No. 681676) in DMSO is also available.
      Catalogue Number681675
      Brand Family Calbiochem®
      SynonymsKY 12420, MLCK Inhibitor II
      References
      ReferencesCross, M.J., et al. 1995. J. Biol. Chem. 270, 25352.
      Nakamura, I., et al. 1995. FEBS Lett. 361, 79.
      Ferby, I.M., et al. 1994. J. Biol. Chem. 269, 30485.
      Okada, T., et al. 1994. J. Biol. Chem. 269, 3568.
      Wymann, M.P. and Arcaro, A. 1994. Biochem. J. 298, 517.
      Arcaro, A. and Wymann, M.P. 1993. Biochem. J. 296, 297.
      Nakanishi, S., et al. 1992. J. Biol. Chem. 267, 2157.
      Bonser, R.W., et al. 1991. Br. J. Pharmacol. 103, 1237.
      Product Information
      CAS number19545-26-7
      ATP CompetitiveN
      FormWhite to off-white solid
      Hill FormulaC₂₃H₂₄O₈
      Chemical formulaC₂₃H₂₄O₈
      ReversibleN
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary Targetphosphatidylinositol-3-kinase
      Primary Target IC<sub>50</sub>5 nM against phosphatidylinositol 3-kinase; 5 nM against PDGF-mediated Ins(3,4,5)P3 formation; 200 nM against myosin light chain kinase
      Purity≥98% by HPLC
      Physicochemical Information
      Cell permeableY
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      RTECSCB9641000
      Safety Information
      R PhraseR: 26/27/28

      Very toxic by inhalation, in contact with skin and if swallowed.
      S PhraseS: 22-36/37/39-45

      Do not breathe dust.
      Wear suitable protective clothing, gloves and eye/face protection.
      In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible).
      Product Usage Statements
      Storage and Shipping Information
      Ship Code Ambient Temperature Only
      Toxicity Highly Toxic
      Hazardous Materials Attention: Due to the nature of the Hazardous Materials in this shipment, additional shipping charges may be applied to your order. Certain sizes may be exempt from the additional hazardous materials shipping charges. Please contact your local sales office for more information regarding these charges.
      Storage -20°C
      Protect from Light Protect from light
      Do not freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications

      Documentation

      Wortmannin - CAS 19545-26-7 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Wortmannin - CAS 19545-26-7 - Calbiochem Certificates of Analysis

      TitleLot Number
      681675

      References

      Reference overview
      Cross, M.J., et al. 1995. J. Biol. Chem. 270, 25352.
      Nakamura, I., et al. 1995. FEBS Lett. 361, 79.
      Ferby, I.M., et al. 1994. J. Biol. Chem. 269, 30485.
      Okada, T., et al. 1994. J. Biol. Chem. 269, 3568.
      Wymann, M.P. and Arcaro, A. 1994. Biochem. J. 298, 517.
      Arcaro, A. and Wymann, M.P. 1993. Biochem. J. 296, 297.
      Nakanishi, S., et al. 1992. J. Biol. Chem. 267, 2157.
      Bonser, R.W., et al. 1991. Br. J. Pharmacol. 103, 1237.

      Citations

      Title
    • Ying Zhang, Mingjuan Liao and Maria L. Dufau. (2006) Phosphatidylinositol 3-kinase/protein kinase Cγ-induced phosphorylation of Sp1 and p107 repressor release have a critical role in histone deacetylase inhibitor-mediated depression of transcription of the luteinizing hormone receptor gene. Molecular and Cellular Biology 26, 6748-6761.
    • Nadine N. Johnson-Farley, Tatyana Travkina and Daniel S. Cowen. (2005) Cumulative activatino of Akt and consequent inhibition of glycogen synthase kinase-3 by brain-derived neurotrophic factor and insulin-like growth factor-1 in cultured hippocampal neurons. Journal of Pharmacology and Experimental Therapeutics in press,.
    • Xu-Wen Liu, et al. (2005) Tissue inhibitor of metalloproteinase-1 protects human breast epithelial cells from extrinsic cell death: a potential oncogenic activity of tissue inhibitor of metalloproteinase-1. Cancer Research 65, 898-906.
    • Kuntebommanahalli N. Thimmaiah, et al. (2005) Identification of N10-Substituted Phenoxazines as Potent and Specific Inhibitors of Akt Signaling. Journal of Biological Chemistry in press,.
    • Yung-Luen Yu, et al. (2005) MAP kinase-mediated phosphorylation of GATA-1 promotes Bcl-XL expression and cell survival. Journal of Biological Chemistry 280, 29533-29542.
    • Hui Zeng, et al. (2005) Flagellin/TLR5 responses in epithelia reveal intertwined activation of inflammatory and apoptotic pathways. American Journal of Physiology Gastrointestinal and Liver Physiology in press,.
    • 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.

      Revision22-March-2019 JSW
      SynonymsKY 12420, MLCK Inhibitor II
      DescriptionA fungal metabolite that acts as a potent, selective, cell-permeable and irreversible inhibitor of phosphatidylinositol 3-kinase (PI 3-kinase) in purified preparations and cytosolic fractions (IC50 = 5 nM). Preincubation of fibroblasts with wortmannin abolishes PDGF-mediated Ins(3,4,5)P3 formation (IC50 = 5 nM). Blocks the catalytic activity of PI 3-kinase without affecting the upstream signaling events. Also blocks the metabolic effects of insulin in isolated rat adipocytes without affecting the insulin receptor tyrosine kinase activity. Inhibits MAP kinase activation induced by platelet activating factor in guinea pig neutrophils (0.2-0.3 µM). Inhibits osteoclastic bone resorption. Inhibits other kinases, such as myosin light chain kinase (IC50 = 200 nM) and PI 4-kinase at concentrations 100-fold higher than that required for the inhibition of PI 3-kinase. Also blocks phospholipase D.
      FormWhite to off-white solid
      Intert gas (Yes/No) Packaged under inert gas
      CAS number19545-26-7
      RTECSCB9641000
      Chemical formulaC₂₃H₂₄O₈
      Structure formulaStructure formula
      Purity≥98% by HPLC
      SolubilityDMSO (25 mg/ml)
      Storage -20°C
      Protect from light
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 2 months at -20°C.
      Toxicity Highly Toxic
      Merck USA index14, 10053
      ReferencesCross, M.J., et al. 1995. J. Biol. Chem. 270, 25352.
      Nakamura, I., et al. 1995. FEBS Lett. 361, 79.
      Ferby, I.M., et al. 1994. J. Biol. Chem. 269, 30485.
      Okada, T., et al. 1994. J. Biol. Chem. 269, 3568.
      Wymann, M.P. and Arcaro, A. 1994. Biochem. J. 298, 517.
      Arcaro, A. and Wymann, M.P. 1993. Biochem. J. 296, 297.
      Nakanishi, S., et al. 1992. J. Biol. Chem. 267, 2157.
      Bonser, R.W., et al. 1991. Br. J. Pharmacol. 103, 1237.
      Citation
    • Ying Zhang, Mingjuan Liao and Maria L. Dufau. (2006) Phosphatidylinositol 3-kinase/protein kinase Cγ-induced phosphorylation of Sp1 and p107 repressor release have a critical role in histone deacetylase inhibitor-mediated depression of transcription of the luteinizing hormone receptor gene. Molecular and Cellular Biology 26, 6748-6761.
    • Nadine N. Johnson-Farley, Tatyana Travkina and Daniel S. Cowen. (2005) Cumulative activatino of Akt and consequent inhibition of glycogen synthase kinase-3 by brain-derived neurotrophic factor and insulin-like growth factor-1 in cultured hippocampal neurons. Journal of Pharmacology and Experimental Therapeutics in press,.
    • Xu-Wen Liu, et al. (2005) Tissue inhibitor of metalloproteinase-1 protects human breast epithelial cells from extrinsic cell death: a potential oncogenic activity of tissue inhibitor of metalloproteinase-1. Cancer Research 65, 898-906.
    • Kuntebommanahalli N. Thimmaiah, et al. (2005) Identification of N10-Substituted Phenoxazines as Potent and Specific Inhibitors of Akt Signaling. Journal of Biological Chemistry in press,.
    • Yung-Luen Yu, et al. (2005) MAP kinase-mediated phosphorylation of GATA-1 promotes Bcl-XL expression and cell survival. Journal of Biological Chemistry 280, 29533-29542.
    • Hui Zeng, et al. (2005) Flagellin/TLR5 responses in epithelia reveal intertwined activation of inflammatory and apoptotic pathways. American Journal of Physiology Gastrointestinal and Liver Physiology in press,.