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

Product Name

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

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

biological source

sea sponge (Discodermia calyx)

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

Quality Level

200

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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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.

General description

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

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

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Certificates of Analysis (COA)

Lot/Batch Number

0000516114

0000513042

0000459352

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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)

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)

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

A major role for the rho-associated coiled coil forming protein kinase in G-protein-mediated Ca2+ sensitization through inhibition of myosin phosphatase in rabbit trachea.

K Iizuka et al.

British journal of pharmacology, 128(4), 925-933 (1999-11-11)

1 G protein-mediated Ca2+ sensitization of airway smooth muscle contraction was investigated with respect to the relative importance of Rho-associated coiled coil forming protein kinase (ROCK) and protein kinase C (PKC). We examined the effects of Y-27632, a ROCK inhibitor

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