495604

Okadaic acid

from Prorocentrum sp., ≥95% (HPLC), solid (glassy), protein phosphatase 1 inhibitor, Calbiochem

• Synonyme(s) : Okadaic Acid, Prorocentrum sp., OA
• Formule empirique (notation de Hill): C₄₄H₆₈O₁₃
• Numéro CAS: 78111-17-8
• Poids moléculaire : 805.00
• Numéro MDL: MFCD00083455
• Code UNSPSC : 12352106
• Nomenclature NACRES : NA.77

Propriétés

• product name: 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).
• Niveau de qualité: 100
• Pureté: ≥95% (HPLC)
• Forme: solid (glassy)
• Fabricant/nom de marque: Calbiochem^®
• Conditions de stockage: OK to freeze; protect from light
• Couleur: colorless
• Solubilité: DMF: soluble; chloroform: soluble; ethanol: soluble; methanol: soluble
• Conditions d'expédition: ambient
• Température de stockage: −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
• Clé InChI: QNDVLZJODHBUFM-AAWJMCDUSA-N

Description

Description générale

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.

Actions biochimiques/physiologiques

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

Conditionnement

Packaged under inert gas

Avertissement

Toxicity: Toxic (F)

Reconstitution

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

Autres remarques

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.

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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.
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Cohen, P., and Cohen, P.T. 1989. J. Biol. Chem.264, 21435.
Haystead, T.A., et al. 1989. Nature337, 78.

Informations légales

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

Informations sur la sécurité

• Pictogrammes: GHS06
• Mention d'avertissement: Danger
• Mentions de danger: H301 + H311 + H331,H315
• Conseils de prudence: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Classification des risques: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2
• Code de la classe de stockage: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable