T9033

Thapsigargin

≥98% (HPLC), solid film

• Empirical Formula (Hill Notation): C₃₄H₅₀O₁₂
• CAS Number: 67526-95-8
• Molecular Weight: 650.75
• MDL number: MFCD00083511
• 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

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

Thapsigargin has been used to study the consequences of calcium depletion in the endoplasmic reticulum (ER) of cells. Thapsigargin has also been used 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. Blocks the transient increase in intracellular Ca²⁺ induced by angiostatin and endostatin. Induces apoptosis by disrupting intracellular free Ca²⁺ levels; incorporated into chemotherapeutic prodrug formulations.

Thapsigargin is a non-competitive inhibitor of the ubiquitous sarco/endoplasmic reticulum Ca²⁺-ATPase (SERCA), commonly used to induce endoplasmic reticulum (ER) stress, in vitro.

Safety Information

• Pictograms: GHS07,GHS08
• 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