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T9033

Thapsigargin

Name: Thapsigargin
Brand: SIGMA

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

Synonym(s):

(-)-Thapsigargin, TG1

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About This Item

Empirical Formula (Hill Notation):

C₃₄H₅₀O₁₂

CAS Number:

67526-95-8

Molecular Weight:

650.75

UNSPSC Code:

12352200

PubChem Substance ID:

24278762

NACRES:

NA.77

MDL number:

MFCD00083511

Assay:

≥98% (HPLC)

Form:

solid film

Quality level:

300

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Product Name

Thapsigargin, ≥98% (HPLC), solid film

biological source

plant (Thapsia garganica)

Quality Level

300

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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Related Categories

Bioactive Small Molecule Inhibitors

Bioactive Small Molecules

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

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.

Other Notes

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

pictograms

GHS08,GHS07

signalword

Danger

hcodes

H315,H319,H334,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number

0000524193

0000455906

0000412742

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Regulation of tissue inhibitor of metalloproteinases-1 in rat Sertoli cells: induction by germ cell residual bodies, interleukin-1alpha, and second messengers.

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)

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)

Thapsigargin-From Traditional Medicine to Anticancer Drug

Agata Jaskulska, et al.

International Journal of Molecular Sciences (2020)

Mutant FUS proteins that cause amyotrophic lateral sclerosis incorporate into stress granules.

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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Global Trade Item Number

SKU	GTIN
T9033-.5MG	04061837380372
T9033-1MG	04061837380402
T9033-5MG	04061837380419
T9033-10MG	04061837380396

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