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C5552

Calyculin A

Name: Calyculin A
Brand: SIGMA

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

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About This Item

Empirical Formula (Hill Notation):

C₅₀H₈₁N₄O₁₅P

CAS Number:

101932-71-2

Molecular Weight:

1009.17

UNSPSC Code:

12352200

PubChem Substance ID:

24892795

NACRES:

NA.77

Beilstein/REAXYS Number:

4903216

MDL number:

MFCD06795864

Assay:

≥90% (HPLC)

Form:

solid

Quality level:

200

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Product Name

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

General description

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

Application

Calyculin A from Discodermia calyx has been used:

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

Biochem/physiol Actions

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

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

GHS06

signalword

Danger

hcodes

H301 + H311 + H331,H315

pcodes

P261 - P264 - P280 - P301 + P310 - P302 + P352 + P312 - P304 + P340 + P311

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

Regulatory Information

高风险级别生物产品--病毒，疫苗等

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Certificates of Analysis (COA)

Lot/Batch Number

0000517986

0000516114

0000513042

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Serine/threonine protein phosphatases and regulation of K-Cl cotransport in human erythrocytes.

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, 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)

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)

Regulation of fowl sperm motility: evidence for the indirect, but not direct, involvement of dynein-ATPase activity on the reversible temperature-dependent immobilization.

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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ReadyShield Phosphatase and Protease Inhibitor Cocktail FAQ

ReadyShield^® phosphatase and protease inhibitor cocktail FAQ for sample protection in a variety of cell types and tissue extracts, including mammalian, plant, and microbial samples. Our ReadyShield^® Protease Inhibitor Cocktail is a non-freezing solution that contains inhibitors with a broad specificity for serine, cysteine, acid proteases and aminopeptidases.

Global Trade Item Number

SKU	GTIN
C5552-10UG	04061833502303

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