O9381

Okadaic acid

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

• Synonyme(s) : OA
• Formule empirique (notation de Hill): C₄₄H₆₈O₁₃
• Numéro CAS: 78111-17-8
• Poids moléculaire : 805.00
• Numéro MDL: MFCD00083455
• Code UNSPSC : 12352106
• ID de substance PubChem : 24898069
• Nomenclature NACRES : NA.77

Propriétés

• product name: Okadaic acid from Prorocentrum concavum, 92-100% (HPLC)
• Niveau de qualité: 200
• Pureté: 92-100% (HPLC)
• Forme: powder
• Solubilité: DMSO: ≥1 mg/mL; ethanol: ≥1 mg/mL; methanol: ≥1 mg/mL; H₂O: insoluble
• Température de stockage: −20°C
• Chaîne SMILES: 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
• Clé InChI: QNDVLZJODHBUFM-WFXQOWMNSA-N

Description

Description générale

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

Application

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Notes préparatoires

Isolated from unialgal cultures of dinoflagellates.

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
• Équipement de protection individuelle: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges