O9381

Okadaic acid

from Prorocentrum concavum, 92-100% (HPLC), powder, protein phosphatase 1 inhibitor

• Synonym(e): OA
• Empirische Formel (Hill-System): C₄₄H₆₈O₁₃
• CAS-Nummer: 78111-17-8
• Molekulargewicht: 805.00
• MDL-Nummer: MFCD00083455
• UNSPSC-Code: 12352106
• PubChem Substanz-ID: 24898069
• NACRES: NA.77

Eigenschaften

• product name: Okadasäure aus Prorocentrum concavum, 92-100% (HPLC)
• Qualitätsniveau: 200
• Assay: 92-100% (HPLC)
• Form: powder
• Löslichkeit: DMSO: ≥1 mg/mL; ethanol: ≥1 mg/mL; methanol: ≥1 mg/mL; H₂O: insoluble
• Lagertemp.: −20°C
• SMILES String: O[C@@H](C[C@@H]([C@@]1([H])O[C@@]2(CCCCO2)CC[C@H]1C)C)[C@]3([H])C([C@@H](O)[C@]4([H])O[C@]5(CC[C@@](/C=C/[C@@H](C)[C@@]6([H])O[C@]7(O[C@H](C[C@@](C)(O)C(O)=O)CC[C@H]7O)C=C(C)C6)([H])O5)CC[C@@]4([H])O3)=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
• InChIKey: QNDVLZJODHBUFM-WFXQOWMNSA-N

Beschreibung

Allgemeine Beschreibung

Okadaic acid is a polyether fatty acid. It is a marine toxin produced by the genera of Prorocentrum and Dinophysis.

Anwendung

Okadaic acid from Prorocentrum concavum has been used as a phosphatase inhibitor:

• to inhibit protein phosphatase 2 in spermatocytes culture
• to treat SH-SY5Y cells to prevent dephosphorylation to maintain tau
• to treat human embryonic kidney 293T cells (HEK293T) or H4 cells to analyse its effect on fused in sarcoma (FUS) protein

Biochem./physiol. Wirkung

Dinoflagellate toxin and an ionophore-like polyether derivative of a 38 carbon, fatty acid. Readily enters cells. Inhibitor of type 1 and type 2A protein phosphatases. Does not inhibit tyrosine phosphatases, alkaline phosphatases or acid phosphatase. Known tumor promotor. Used to study various cellular processes including cell cycle, apoptosis, nitric oxide metabolism and calcium signaling.

Leistungsmerkmale und Vorteile

This compound is featured on the Phosphoprotein Phosphatases (Serine/Threonine) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Angaben zur Herstellung

Isolated from unialgal cultures of dinoflagellates.

Sicherheitshinweise

• Piktogramme: GHS06
• Signalwort: Danger
• H-Sätze: H301 + H311 + H331,H315
• P-Sätze: P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311
• Gefahreneinstufungen: Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2
• Lagerklassenschlüssel: 6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges