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586005

Millipore

Thapsigargin

≥97% (TLC), solid, endoplasmic reticular Ca2+-ATPase inhibitor, Calbiochem®

Synonym(s):

Thapsigargin - CAS 67526-95-8 - Calbiochem

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About This Item

Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
67526-95-8
Molecular Weight:
650.75
MDL number:
MFCD00083511
UNSPSC Code:
12352200
NACRES:
NA.77

Product Name

Thapsigargin - CAS 67526-95-8 - Calbiochem, Thapsigargin, CAS 67526-95-8, is a cell-permeable, tumor-promoting sesquiterpene lactone that releases calcium by non-competitvley inhibiting endoplasmic reticular Ca2+-ATPase (IC₅₀ = 4-13 nM).

Quality Level

200

Assay

≥97% (TLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

colorless

solubility

DMSO: >1 mg/mL
ethanol: 5 mg/mL

shipped in

ambient

storage temp.

−20°C

SMILES string

O1[C@@H]2[C@]([C@H](C[C@@]([C@H]3[C@@H]([C@H](C(=C32)C)OC(=O)\C(=C/C)\C)OC(=O)CCCCCCC)(OC(=O)C)C)OC(=O)CCC)([C@@](C1=O)(O)C)O

InChI

1S/C34H50O12/c1-9-12-13-14-15-17-24(37)43-28-26-25(20(5)27(28)44-30(38)19(4)11-3)29-34(41,33(8,40)31(39)45-29)22(42-23(36)16-10-2)18-32(26,7)46-21(6)35/h11,22,26-29,40-41H,9-10,12-18H2,1-8H3/b19-11-/t22-,26+,27-,28-,29-,32-,33+,34+/m0/s1

InChI key

IXFPJGBNCFXKPI-FSIHEZPISA-N

Related Categories

General description

A cell-permeable tumor-promoting sesquiterpene lactone that releases Ca2+ by inhibiting endoplasmic reticular Ca2+-ATPase (IC50 = 4-13 nM). Does not increase inositol phosphates and has no significant effect on protein kinase C. Increases Ca2+-dependent Na+ influx in human platelets in a dose-dependent manner. Induces apoptosis in rat thymocytes and in human hepatoma cells. Shown to induce apoptosis in alveolar rhabdomyosarcoma cells by elevating Akt-stimulated PAX3-FOXO1 phosphorylation and promoting its proteasomal degradation.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
endoplasmic reticular Ca2+ ATPase
Product does not compete with ATP.
Reversible: no
Target IC50: 4-13 nM against endoplasmic reticular Ca2+-ATPase

Warning

Toxicity: Irritant (B)

Reconstitution

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for 2-3 months at -20°C.

Other Notes

Jothi, M., et al. 2013. Mol. Cancer Ther. In press.
Won, J.G. and Orth, D.N. 1995. Endocrinology 136, 5399.
Tepel, M., et al. 1994. Biochim. Biophys. Acta1220, 248.
Begum, N., et al. 1993. J. Biol. Chem. 268, 3352.
Low, A.M., et al. 1993. Eur. J. Pharmacol.230, 53.
Tsukamoto, A. and Karneko, Y. 1993. Cell. Biol. Int.17, 969.
Wong, W.L., et al. 1993. Biochem. J.289, 71.
Glennon, M.C., et al. 1992. J. Biol. Chem. 267, 25568.
Xu, Y., et al. 1992. J. Neurochem.59, 2224.
Mason, M.J., et al. 1991. J. Biol. Chem. 266, 20856.
Thastrup, O., et al. 1990. Proc. Natl. Acad. Sci. USA87, 2466.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Danger

Hazard Statements

H315,H319,H334,H335

Hazard Classifications

Eye Irrit. 2 - Resp. Sens. 1 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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