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495604 Okadaic Acid, Prorocentrum sp. - CAS 78111-17-8 - Calbiochem

Okadaic Acid, CAS 78111-17-8, is a highly potent inhibitor of protein phosphatase 1 (IC₅₀ = 10-15 nM) and 2A (IC₅₀ = 0.1 nM).

MSDS (material safety data sheet) or SDS, CoA and CoQ, dossiers, brochures and other available documents.

Synonyms: OA

Primary Target: Protein phosphatase
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      Overview

      Replacement Information

      Key Specifications Table

      CAS #Empirical Formula
      78111-17-8C₄₄H₆₈O₁₃
      Description
      OverviewAn ionophore-like polyether derivative of a C38 fatty acid compound that has tumor promoting properties. Potent inhibitor of protein phosphatase 1 (IC50 = 10-15 nM) and protein phosphatase 2A (IC50 = 0.1 nM). Does not affect the activity of tyrosine phosphatases, alkaline phosphatases, or acid phosphatases. Useful for the study of protein phosphatases in cell extracts as well as in intact cells. Induces apoptosis in human breast carcinoma cells (MB-231 and MCF7) and in myeloid cells but inhibits glucocorticoid-induced apoptosis in T cell hybridomas. Has marked contractile effects on smooth muscle and heart muscle. Implicated as causative agent of diarrhetic shellfish poisoning. A 250 µM (25 µg/124 µl) solution of Okadaic Acid, (Cat. No. 495609) in DMSO is also available.
      Catalogue Number495604
      Brand Family Calbiochem®
      SynonymsOA
      References
      ReferencesGjertsen, B.T., et al. 1994. J. Cell Sci. 107, 3363.
      Kiguchi, K., et al. 1994. Cell Growth Differentiation 5, 995.
      Ohaka, Y., et al. 1993. Biochem. Biophys. Res. Commun. 197, 916.
      Gopalakrishna, R., et al. 1992. Biochem. Biophys. Res. Commun. 189, 950.
      Kreienbuhl, P., et al. 1992. Blood 80, 2911.
      Nomura, M., et al. 1992. Biochemistry 31, 11915.
      Song, Q., et al. 1992. J. Cell Physiol. 153, 550.
      Tada, Y., et al. 1992. Immunopharmacol. 24, 17.
      Cohen, P., et al. 1990. Trends Biochem. Sci. 15, 98.
      Cohen, P. 1989. Annu. Rev. Biochem. 58, 453.
      Cohen, P., and Cohen, P.T. 1989. J. Biol. Chem. 264, 21435.
      Haystead, T.A., et al. 1989. Nature 337, 78.
      Product Information
      CAS number78111-17-8
      ATP CompetitiveN
      FormColorless glassy solid
      Hill FormulaC₄₄H₆₈O₁₃
      Chemical formulaC₄₄H₆₈O₁₃
      ReversibleN
      Structure formula ImageStructure formula Image
      Quality LevelMQ100
      Applications
      Biological Information
      Primary TargetProtein phosphatase
      Primary Target IC<sub>50</sub>10-15 nM and 0.1 nM against protein phosphatase 1 and protein phosphatase 2A, respectively
      Purity≥95% by HPLC
      Physicochemical Information
      Cell permeableN
      Dimensions
      Materials Information
      Toxicological Information
      Safety Information according to GHS
      RTECSAA8227800
      Safety Information
      R PhraseR: 23/24/25-38

      Toxic by inhalation, in contact with skin and if swallowed.
      Irritating to skin.
      S PhraseS: 22-26-36/37/39-45

      Do not breathe dust.
      In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
      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 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 1 month at -20°C.
      Packaging Information
      Packaged under inert gas Packaged under inert gas
      Transport Information
      Supplemental Information
      Specifications
      Global Trade Item Number
      Catalog Number GTIN
      495604 0

      Documentation

      Okadaic Acid, Prorocentrum sp. - CAS 78111-17-8 - Calbiochem SDS

      Title

      Safety Data Sheet (SDS) 

      Okadaic Acid, Prorocentrum sp. - CAS 78111-17-8 - Calbiochem Certificates of Analysis

      TitleLot Number
      495604

      References

      Reference overview
      Gjertsen, B.T., et al. 1994. J. Cell Sci. 107, 3363.
      Kiguchi, K., et al. 1994. Cell Growth Differentiation 5, 995.
      Ohaka, Y., et al. 1993. Biochem. Biophys. Res. Commun. 197, 916.
      Gopalakrishna, R., et al. 1992. Biochem. Biophys. Res. Commun. 189, 950.
      Kreienbuhl, P., et al. 1992. Blood 80, 2911.
      Nomura, M., et al. 1992. Biochemistry 31, 11915.
      Song, Q., et al. 1992. J. Cell Physiol. 153, 550.
      Tada, Y., et al. 1992. Immunopharmacol. 24, 17.
      Cohen, P., et al. 1990. Trends Biochem. Sci. 15, 98.
      Cohen, P. 1989. Annu. Rev. Biochem. 58, 453.
      Cohen, P., and Cohen, P.T. 1989. J. Biol. Chem. 264, 21435.
      Haystead, T.A., et al. 1989. Nature 337, 78.

      Brochure

      Title
      Protein Phosphatases Technical Bulletin

      Citations

      Title
    • Mike T. Lin, et al. (2005) Ca2+-activated K+ channel-associated phosphatase and kinase activities during development. American Journal of Physiology Heart and Circulatory Physiology 289, H414-H425.
    • Ramesh M. Ray, Sujoy bhattacharya and Leonard R. Johnson. (2005) Protein phosphatase 2A (PP2A) regulates apoptosis in IEC-6 cells. Journal of Biological Chemistry 280, 31091-31100.
      		•
      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.

      Revision15-May-2008 RFH
      SynonymsOA
      DescriptionAn ionophore-like polyether derivative of a C38 fatty acid compound isolated from the dinoflagellates that have fed on the marine sponge Halinchrondria okadai. It is a potent non-comepetitive, reversible inhibitor of serine/threonine-specific protein phosphatases 1 (PP1, IC50 = 10-15 nM, rabbit skeletal muscle, catalytic subunit) and 2A (PP2A, IC50 = 0.1 nM, rabbit skeletal muscle, catalytic subunit). It has only a trivial effect on protein phosphatase 2B (IC50 = 5 µM), a Ca2+/calmodulin-dependent enzyme, while PP2C, a Mg2+ dependent enzyme, is unaffected. Okadaic acid has no significant effect on the activities of tyrosine phosphatases, alkaline phosphatase, acid phosphatase, and inositol trisphosphatase. It is also a non-phorbol ester-type tumor promoter on mouse skin. Useful for the study of protein phosphatases and of PP1/PP2A in cell extracts, as well as in intact cells. Induces apoptosis in human breast carcinoma (MB-231 and MCF-7) and in myeloid cells, but inhibits glucocorticoid-induced apoptosis in T-cell hybridomas. Has marked contractile effect on smooth muscles and heart muscles. Implicated as a causative agent of diarrhetic shellfish poisoning.
      FormColorless glassy solid
      Intert gas (Yes/No) Packaged under inert gas
      CAS number78111-17-8
      RTECSAA8227800
      Chemical formulaC₄₄H₆₈O₁₃
      Structure formulaStructure formula
      Purity≥95% by HPLC
      SolubilityMethanol, ethanol, DMF, or CHCl₃
      Storage Protect from light
      -20°C
      Do Not Freeze Ok to freeze
      Special InstructionsFollowing reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.
      Toxicity Toxic
      Merck USA index14, 6819
      ReferencesGjertsen, B.T., et al. 1994. J. Cell Sci. 107, 3363.
      Kiguchi, K., et al. 1994. Cell Growth Differentiation 5, 995.
      Ohaka, Y., et al. 1993. Biochem. Biophys. Res. Commun. 197, 916.
      Gopalakrishna, R., et al. 1992. Biochem. Biophys. Res. Commun. 189, 950.
      Kreienbuhl, P., et al. 1992. Blood 80, 2911.
      Nomura, M., et al. 1992. Biochemistry 31, 11915.
      Song, Q., et al. 1992. J. Cell Physiol. 153, 550.
      Tada, Y., et al. 1992. Immunopharmacol. 24, 17.
      Cohen, P., et al. 1990. Trends Biochem. Sci. 15, 98.
      Cohen, P. 1989. Annu. Rev. Biochem. 58, 453.
      Cohen, P., and Cohen, P.T. 1989. J. Biol. Chem. 264, 21435.
      Haystead, T.A., et al. 1989. Nature 337, 78.
      Citation
    • Mike T. Lin, et al. (2005) Ca2+-activated K+ channel-associated phosphatase and kinase activities during development. American Journal of Physiology Heart and Circulatory Physiology 289, H414-H425.
    • Ramesh M. Ray, Sujoy bhattacharya and Leonard R. Johnson. (2005) Protein phosphatase 2A (PP2A) regulates apoptosis in IEC-6 cells. Journal of Biological Chemistry 280, 31091-31100.
      		•

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      Categories

      Life Science Research > Inhibitors and Biochemicals > Small Molecules & Inhibitors > Protein Phosphorylation / Dephosphorylation > Protein Phosphatase Inhibitors