T9033

Thapsigargin

≥98% (HPLC), solid film

• Synonym(s): (-)-Thapsigargin, TG1
• Empirical Formula (Hill Notation): C₃₄H₅₀O₁₂
• CAS Number: 67526-95-8
• Molecular Weight: 650.75
• MDL number: MFCD00083511
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278762
• NACRES: NA.77

Properties

• 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

Description

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.

Other Notes

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

Safety Information

• Pictograms: GHS08,GHS07
• Signal Word: Danger
• Hazard Statements: H315,H319,H334,H335
• Precautionary Statements: 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 Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves