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C5552

Sigma-Aldrich

Calyculin A from Discodermia calyx

≥90% (HPLC), solid

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Empirical Formula (Hill Notation):
C50H81N4O15P
CAS Number:
Molecular Weight:
1009.17
Beilstein:
4903216
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

sea sponge (Discodermia calyx)

Quality Level

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.

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

Skull and crossbones

Signal Word

Danger

Hazard Statements

Hazard Classifications

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

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

高风险级别生物产品--病毒,疫苗等

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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)
Calyculin A, protein phosphatase inhibitor, enhances capacitation of human sperm
Furuya S, et al.
Fertility and Sterility, 59(1), 216-222 (1993)
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
Michael A Kuefner et al.
International journal of radiation biology, 89(6), 424-432 (2013-02-01)
The purpose of this study was to investigate the effect of calyculin A on the number of γ-H2AX foci (phosphorylated histone variant 2AX) in lymphocytes after in vitro and in vivo irradiation with rather low doses as they are used

Articles

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