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Merck

T9033

Thapsigargin

From plant (Thapsia garganica), ≥98% (HPLC), IP3-independent intracellular calcium releaser, solid film

Sinónimos:

(-)-Thapsigargin, TG1

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About This Item

Fórmula empírica (notación de Hill):
C34H50O12
Número CAS:
67526-95-8
Peso molecular:
650.75
UNSPSC Code:
12352200
PubChem Substance ID:
24278762
NACRES:
NA.77
MDL number:
MFCD00083511

Nombre del producto

Thapsigargin, ≥98% (HPLC), solid film

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

biological source

plant (Thapsia garganica)

assay

≥98% (HPLC)

form

solid film

solubility

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

storage temp.

−20°C

Quality Level

300

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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

Potent, cell-permeable, IP3-independent intracellular calcium releaser.
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.

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).

Other Notes

2024 CiteAb Award Winner for Supplier Succeeding in Parkinson′s Research

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

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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Certificados de análisis (COA)

Lot/Batch Number
0000455906
0000455906
0000412742
0000412741
0000412743

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Encuentre la documentación para los productos que ha comprado recientemente en la Biblioteca de documentos.

Visite la Librería de documentos

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
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)
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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