C5552

Calyculin A

from sea sponge (Discodermia calyx), ≥90% (HPLC), solid, protein phosphatases types 1 and 2A inhibitor

• Empirische Formel (Hill-System): C₅₀H₈₁N₄O₁₅P
• CAS-Nummer: 101932-71-2
• Molekulargewicht: 1009.17
• Beilstein: 4903216
• MDL-Nummer: MFCD06795864
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24892795
• NACRES: NA.77

Eigenschaften

• Produktbezeichnung: Calyculin A aus Discodermia calyx, ≥90% (HPLC), solid
• Biologische Quelle: sea sponge (Discodermia calyx)
• Qualitätsniveau: 200
• Assay: ≥90% (HPLC)
• Form: solid
• Mol-Gew.: ~_1.0 kDa
• Farbe: white
• mp (Schmelzpunkt): 247-249 °C
• Löslichkeit: DMSO: soluble; ethanol: soluble
• Lagertemp.: −20°C
• SMILES String: COC[C@@H]([C@H](O)[C@H](O)C(=O)NCC[C@H](C)c1nc(\C=C\C[C@@H]2O[C@]3(C[C@@H](O)[C@@H]2C)OC([C@H](C[C@H](O)[C@H](C)[C@H](O)[C@H](C)\C=C(C)\C(C)=C\C=C\C(C)=C/C#N)OC)[C@H](OP(O)(O)=O)C3(C)C)co1)N(C)C
• InChI: 1S/C50H81N4O15P/c1-29(20-22-51)16-14-17-30(2)32(4)24-33(5)42(57)35(7)38(55)25-41(65-13)45-46(69-70(61,62)63)49(8,9)50(68-45)26-39(56)34(6)40(67-50)19-15-18-36-27-66-48(53-36)31(3)21-23-52-47(60)44(59)43(58)37(28-64-12)54(10)11/h14-18,20,24,27,31,33-35,37-46,55-59H,19,21,23,25-26,28H2,1-13H3,(H,52,60)(H2,61,62,63)/b16-14+,18-15+,29-20-,30-17+,32-24+/t31-,33+,34-,35-,37-,38-,39+,40-,41-,42+,43-,44-,45+,46-,50+/m0/s1
• InChIKey: FKAWLXNLHHIHLA-YCBIHMBMSA-N

Beschreibung

Allgemeine Beschreibung

Calyculin A is derived from the marine sponge Discodermia calyx. It corresponds to a molecular weight of 1008 Da.[1]

Anwendung

Calyculin A from Discodermia calyx has been used:

• as an inhibitor of serine-threonine protein phosphatase 2A[2]
• as an inhibitor of cyclin D1 phosphatase in human breast cancer cells[3]
• as an inhibitor of protein phosphatase 2A (PP2A) and PP1 in mouse melanoma cell lines B16-F0 cells[4]

Biochem./physiol. Wirkung

Calyculin A from Discodermia calyx binds to the okadaic acid receptors.[1] In smooth muscles, it activates calcium channel. Calyculin A regulates protein phosphorylation thereby regulating capacitation in sperm.[5] It enhances phosphorylation of nuclear factor κ-light-chain-enhancer of activated B cells (NF-κB) and apoptosis.[6]

Inhibitor of protein phosphatases types 1 and 2A; marine toxin, potent tumor promotor.

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.

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