495604

Okadaic Acid, Prorocentrum sp.

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).

• Synonym(s): Okadaic Acid, Prorocentrum sp., OA
• Empirical Formula (Hill Notation): C₄₄H₆₈O₁₃
• CAS Number: 78111-17-8
• Molecular Weight: 805.00
• MDL number: MFCD00083455
• UNSPSC Code: 12352106

Properties

• Quality Level: 100
• Assay: ≥95% (HPLC)
• form: solid (glassy)
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: colorless
• solubility: DMF: soluble; chloroform: soluble; ethanol: soluble; methanol: soluble
• shipped in: ambient
• storage temp.: −20°C
• InChI: 1S/C44H68O13/c1-25-21-34(55-44(23-25)35(46)12-11-31(54-44)24-41(6,50)40(48)49)26(2)9-10-30-14-18-43(53-30)19-15-33-39(57-43)36(47)29(5)38(52-33)32(45)22-28(4)37-27(3)13-17-42(56-37)16-7-8-20-51-42/h9-10,23,26-28,30-39,45-47,50H,5,7-8,11-22,24H2,1-4,6H3,(H,48,49)/b10-9+/t26-,27-,28+,30+,31+,32+,33-,34+,35-,36-,37?,38+,39?,41-,42+,43-,44-/m1/s1
• InChI key: QNDVLZJODHBUFM-AAWJMCDUSA-N

Description

General description

An 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.

An 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.

Biochem/physiol Actions

Cell permeable: no

Primary Target
Protein phosphatase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 10-15 nM and 0.1 nM against protein phosphatase 1 and protein phosphatase 2A, respectively

Packaging

Packaged under inert gas

Warning

Toxicity: Toxic (F)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

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.

Gjertsen, B.T., et al. 1994. J. Cell Sci.107, 3363.
Kiguchi, K., et al. 1994. Cell Growth Differentiation5, 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. Blood80, 2911.
Nomura, M., et al. 1992. Biochemistry31, 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. Nature337, 78.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Pictograms: GHS06
• Signal Word: Danger
• Hazard Statements: H301 + H311 + H331 - H315
• Precautionary Statements: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Hazard Classifications: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2
• Storage Class Code: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable