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T9033

Sigma-Aldrich

Thapsigargin

≥98% (HPLC), solid film

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Synonym(s):
(-)-Thapsigargin, TG1
Empirical Formula (Hill Notation):
C34H50O12
CAS Number:
Molecular Weight:
650.75
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

plant (Thapsia garganica)

Quality Level

assay

≥98% (HPLC)

form

solid film

solubility

acetonitrile: soluble 9.80-10.20 mg/mL
DMSO: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

[H][C@@]12C([C@H](OC([C@]3(O)C)=O)[C@]3(O)[C@@H](OC(CCC)=O)C[C@]2(C)OC(C)=O)=C(C)[C@H](OC(/C(C)=C(C)/[H])=O)[C@H]1OC(CCCCCCC)=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

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T5580P0046S5068
Thapsigargin ≥98% (HPLC), solid film

T9033

Thapsigargin

Myxothiazol from Myxococcus fulvus Mx f85, ≥98% (HPLC)

T5580

Myxothiazol

Pyocyanin from Pseudomonas aeruginosa, ≥98% (HPLC)

P0046

Pyocyanin

Sigma-Aldrich

S5068

Salmeterol xinafoate

form

solid film

form

-

form

solid

form

solid

Quality Level

300

Quality Level

200

Quality Level

200

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

-

solubility

acetonitrile: soluble 9.80-10.20 mg/mL, ethanol: soluble, DMSO: soluble

solubility

chloroform: soluble 9.80-10.20 mg/mL, clear, colorless to yellow, DMSO: soluble, acetone: soluble, dichloromethane: soluble, ethanol: soluble, ethyl acetate: soluble, methanol: soluble

solubility

DMSO: soluble, acetone: soluble, chloroform: soluble, ethanol: soluble

solubility

H2O: slightly soluble, ethanol: slightly soluble, methanol: freely soluble

biological source

plant (Thapsia garganica)

biological source

Myxococcus fulvus Mx f85

biological source

Pseudomonas aeruginosa

biological source

-

General description

Thapsigargin, a guaianolide-type sesquiterpene lactone, is a widely used inhibitor of the ubiquitous sarcoplasmic/endoplasmic reticulum Ca2+ ATPase (SERCA). It can activate endoplasmic reticulum (ER) stress and the unfolded protein response (UPR). Thapsigargin is a natural phytochemical found in the roots and fruits of Mediterranean plants from Thapsia garganica (Apiaceae) species. Thapsigargin promotes the release of translational arrest and induces proteome-wide changes in metabolic pathways within cells infected with coronavirus (CoV).

Application

Thapsigargin has been used as an endoplasmic reticulum (ER) stress inducer:
  • to study its effect on cyclase-associated protein 2 (CAP2) expression in liver cancer cells
  • in the cell viability experiment using ARPE -19 cells (human retinal pigment epithelial cells)
  • to study its effect on lipocalin 2 (LCN2) glycosylation in primary hepatocytes
  • to study the consequences of calcium depletion in the endoplasmic reticulum (ER) of cells
  • to study its effect on tissue inhibitor of metalloproteinases-1 (TIMP-1) mRNA expression in rat Sertoli cells

Biochem/physiol Actions

Thapsigargin is a potent, cell-permeable, IP3-independent intracellular calcium release. It blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. It also induces apoptosis by disrupting intracellular free Ca2+ levels and is incorporated into chemotherapeutic prodrug formulations.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves


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Thapsigargin: key to new host-directed coronavirus antivirals?
Shaban MS, et al.
Trends in Pharmacological Sciences (2022)
Thapsigargin-From Traditional Medicine to Anticancer Drug
Agata Jaskulska, et al.
International Journal of Molecular Sciences (2020)
L M Grønning et al.
Biology of reproduction, 62(4), 1040-1046 (2000-03-22)
In the testis, FSH has been shown to induce the expression and secretion of tissue inhibitor of metalloproteinases-1 (TIMP-1) from Sertoli cells in vitro. This study was performed to elucidate further the cellular origin of testicular TIMP-1 and its expression
A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases
Treiman M, et al.
Trends in Pharmacological Sciences (1998)
Daryl A Bosco et al.
Human molecular genetics, 19(21), 4160-4175 (2010-08-12)
Mutations in the RNA-binding protein FUS (fused in sarcoma) are linked to amyotrophic lateral sclerosis (ALS), but the mechanism by which these mutants cause motor neuron degeneration is not known. We report a novel ALS truncation mutant (R495X) that leads

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