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

495604
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      Overview

      Replacement Information

      Key Specifications Table

      Empirical FormulaCAS #
      C₄₄H₆₈O₁₃ 78111-17-8

      Pricing & Availability

      Catalog NumberAvailability Packaging Qty/Pack Price Quantity
      495604-100UG
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          Alu drum 100 μg
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          495604-25UG
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              Glass bottle 25 μg
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              495604-500UG
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                  Alu drum 500 μg
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                  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
                  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

                  Documentation

                  SDS

                  Title

                  Safety Data Sheet (SDS) 

                  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
                  Protease and Phosphatase Inhibitor Cocktails Brochure
                  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 -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 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.
                • Related Products & Applications

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                  Categories

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