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C5552

Sigma-Aldrich

Calyculin A

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

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About This Item

Fórmula empírica (notación de Hill):
C50H81N4O15P
Número de CAS:
101932-71-2
Peso molecular:
1009.17
Beilstein/REAXYS Number:
4903216
MDL number:
MFCD06795864
UNSPSC Code:
12352200
PubChem Substance ID:
24892795
NACRES:
NA.77
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Nombre del producto

Calyculin A from Discodermia calyx, ≥90% (HPLC), solid

biological source

sea sponge (Discodermia calyx)

Quality Level

200

assay

≥90% (HPLC)

form

solid

mol wt

~_1.0 kDa

color

white

mp

247-249  °C

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−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

InChI key

FKAWLXNLHHIHLA-YCBIHMBMSA-N

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General description

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

Application

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 Actions

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.

Features and Benefits

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.

pictograms

Skull and crossbones
GHS06

signalword

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Skin Irrit. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000417280
0000417280
0000392436
0000387176
0000387178

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Visite la Librería de documentos

I Bize et al.
The American journal of physiology, 277(5 Pt 1), C926-C936 (1999-11-24)
Activation of K-Cl cotransport is associated with activation of membrane-bound serine/threonine protein phosphatases (S/T-PPases). We characterize red blood cell S/T-PPases and K-Cl cotransport activity regarding protein phosphatase inhibitors and response to changes in ionic strength and cell size. Protein phosphatase
Interleukin 4 regulates phosphorylation of serine 756 in the transactivation domain of Stat6 roles for multiple phosphorylation sites and Stat6 function
Wang Y, et al.
The Journal of Biological Chemistry, 279(24), 25196-25203 (2004)
Calyculin A induces apoptosis and stimulates phosphorylation of p65NF-kappaB in human osteoblastic osteosarcoma MG63 cells
Tanaka H, et al.
International Journal of Oncology, 31(2), 389-396 (2007)
Calyculin A, an inhibitor of protein phosphatases, a potent tumor promoter on CD-1 mouse skin
Suganuma M, et al.
Cancer Research, 50(12), 3521-3525 (1990)
Koji Ashizawa et al.
Theriogenology, 79(3), 558-565 (2012-12-19)
Potential mechanisms of the reversible temperature-dependent immobilization of fowl sperm were investigated. At 30 °C, motility of demembranated fowl sperm was inhibited by adding 2 mM ethylene glycol-bis (2-aminoethylether)-N,N,N',N'-tetraacetic acid (EGTA), but restored immediately after the subsequent addition of 2
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