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T9033

Sigma-Aldrich

Thapsigargin

≥98% (HPLC), solid film

Sinónimos:

(-)-Thapsigargin, TG1

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About This Item

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

origen biológico

plant (Thapsia garganica)

Nivel de calidad

300

Análisis

≥98% (HPLC)

formulario

solid film

solubilidad

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

temp. de almacenamiento

−20°C

cadena SMILES

[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

Clave InChI

IXFPJGBNCFXKPI-FSIHEZPISA-N

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Descripción general

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).

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Otras notas

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

Pictogramas

Exclamation markHealth hazard
GHS07,GHS08

Palabra de señalización

Danger

Frases de peligro

H315 - H319 - H334 - H335

Clasificaciones de peligro

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

Órganos de actuación

Respiratory system

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

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

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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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
Nicole S Hou et al.
Proceedings of the National Academy of Sciences of the United States of America, 111(22), E2271-E2280 (2014-05-21)
The Mediator is a conserved transcriptional coregulator complex required for eukaryotic gene expression. In Caenorhabditis elegans, the Mediator subunit mdt-15 is essential for the expression of genes involved in fatty acid metabolism and ingestion-associated stress responses. mdt-15 loss of function
Jing Deng et al.
Molecular and cellular biology, 24(23), 10161-10168 (2004-11-16)
Numerous stressful conditions activate kinases that phosphorylate the alpha subunit of translation initiation factor 2 (eIF2alpha), thus attenuating mRNA translation and activating a gene expression program known as the integrated stress response. It has been noted that conditions associated with
Maximilien Tailler et al.
Cell death and differentiation, 26(9), 1766-1781 (2018-12-13)
Drugs targeting various pro-survival BCL-2 family members (''BH3 mimetics'') have efficacy in hemopoietic malignancies, but the non-targeted pro-survival family members can promote resistance. Pertinently, the sensitivity of some tumor cell lines to BH3 mimetic ABT737, which targets BCL-2, BCL-XL, and
V Shinde et al.
Cell death & disease, 7, e2085-e2085 (2016-02-06)
The molecular mechanism of autosomal dominant retinitis pigmentosa (ADRP) in rats is closely associated with a persistently activated unfolded protein response (UPR). If unchecked, the UPR might trigger apoptosis, leading to photoreceptor death. One of the UPR-activated cellular signaling culminating
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