Thapsigargin

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Cat.No. 1138 - Thapsigargin | C34H50O12 | CAS No. 67526-95-8
Description: Potent inhibitor of SERCA ATPase
Chemical Name: (3S,3aR,4S,6S,6AR,7S,8S,9bS)-6- (Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-trimethyl-8-[[(2Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl octanoate
Purity: ≥97% (HPLC)
Datasheet
Citations (26)

Biological Activity

Potent inhibitor of sarco-endoplasmic reticulum Ca2+-ATPases. Causes ER stress; can be used to induce autophagy in mammalian cells.

Technical Data

M. Wt 650.76
Formula C34H50O12
Storage Desiccate at -20°C
Purity ≥97% (HPLC)
CAS Number 67526-95-8
PubChem ID 446378
InChI Key IXFPJGBNCFXKPI-FSIHEZPISA-N
Smiles O=C(O[C@@H]2[C@@]3(O)[C@@H](OC([C@](C)3O)=O)C1=C(C)[C@H](OC(/C(C)=C\C)=O)[C@@H](OC(CCCCCCC)=O)[C@@]([H])1[C@](OC(C)=O)(C)C2)CCC

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 65.08 100

Preparing Stock Solutions

The following data is based on the product molecular weight 650.76. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.54 mL 7.68 mL 15.37 mL
5 mM 0.31 mL 1.54 mL 3.07 mL
10 mM 0.15 mL 0.77 mL 1.54 mL
50 mM 0.03 mL 0.15 mL 0.31 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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Safety Datasheet

References

References are publications that support the products' biological activity.

Davidson and Varhol (1995) Kinetics of thapsigargin-Ca2+-ATPase (sarcoplasmic reticulum) interaction reveals a two-step binding mechanism and picomolar inhibition. J.Biol.Chem. 270 11731 PMID: 7744817

Treiman et al (1998) A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca2+-ATPases. TiPS 19 131 PMID: 9612087

Yu et al (1998) Specific substitutions at amino acid 256 of the sarcoplasmic/endoplasmic reticulum Ca2+ transport ATPase mediate resistance to thapsigargin in thapsigargin-resistant hamster cells. J.Biol.Chem. 273 3542 PMID: 9452480

Ding et al (2007) Differential effects of endoplasmic reticulum stress-induced autophagy on cell survival. J.Biol.Chem. 282 4702 PMID: 17135238


If you know of a relevant reference for Thapsigargin, please let us know.

View Related Products by Product Action

View all Ca2+-ATPase Inhibitors

Keywords: Potent inhibitors inhibits SERCA ATPase Ca2+ modulators Ca2+-ATPase Signaling Signalling Calcium-ATPase P-type Transporters Ion Pumps Ca2+-ATPase

26 Citations for Thapsigargin

Citations are publications that use Tocris products. Selected citations for Thapsigargin include:

Mätlik et al (2016) Role of two sequence motifs of mesencephalic astrocyte-derived neurotrophic factor in its survival-promoting activity. Cell Death Dis 6 e2032 PMID: 26720341

Salzer et al (2016) Control of sensory neuron excitability by serotonin involves 5HT2C receptors and Ca2+-activated chloride channels. Neuropharmacology 110 (A) 277 PMID: 27511837

Shambharkar et al (2015) TMEM203 Is a Novel Regulator of Intracellular Calcium Homeostasis and Is Required for Spermatogenesis. J Cell Biol 10 e0127480 PMID: 25996873

Cao et al (2015) Calcium release through P2X4 activates calmodulin to promote endolysosomal membrane fusion. PLoS One 209 879 PMID: 26101220

Azab et al (2015) Binding of αherpesvirus Glycoprotein H to Surface α4β1-Integrins Activates Calcium-Signaling Pathways and Induces Phosphatidylserine Exposure on the Plasma Membrane. Endocrinology 6 PMID: 26489864

Velásquez-Martínez et al (2015) α-1 adrenoreceptors modulate GABA release onto ventral tegmental area dopamine neurons. Pflugers Arch 88 110 PMID: 25261018

Dobson et al (2015) Caffeine Modulates Vesicle Release and Recovery at Cerebellar Parallel Fibre Terminals, Independently of Calcium and Cyclic AMP Signalling. J Neuroinflammation 10 e0125974 PMID: 25933382

Glanowska and Moenter (2015) Differential regulation of GnRH secretion in the preoptic area (POA) and the median eminence (ME) in male mice. Neuropharmacology 156 231 PMID: 25314270

Podszywalow-Bartnicka et al (2014) Downregulation of BRCA1 protein in BCR-ABL1 leukemia cells depends on stress-triggered TIAR-mediated suppression of translation. Biochim Biophys Acta 13 3727 PMID: 25483082

Kondratska et al (2014) Orai1 and STIM1 mediate SOCE and contribute to apoptotic resistance of pancreatic adenocarcinoma. PLoS One 1843 2263 PMID: 24583265

Soltoff and Lannon (2013) Activation of ERK1/2 by store-operated calcium entry in rat parotid acinar cells. PLoS One 8 e72881 PMID: 24009711

Grassin-Delyle et al (2013) The expression and relaxant effect of bitter taste receptors in human bronchi. Respir Res 14 134 PMID: 24266887

Semenov et al (2013) Recruitment of the intracellular Ca2+ by ultrashort electric stimuli: the impact of pulse duration. Cell Calcium 54 145 PMID: 23777980

Varadarajan et al (2013) Endoplasmic reticulum membrane reorganization is regulated by ionic homeostasis. PLoS One 8 e56603 PMID: 23457590

Pinheiro et al (2013) Bradykinin-induced Ca2+ signaling in human subcutaneous fibroblasts involves ATP release via hemichannels leading to P2Y12 receptors activation. Cell Commun Signal 11 70 PMID: 24047499

Few et al (2012) Asynchronous Ca2+ current conducted by voltage-gated Ca2+ (CaV)-2.1 and CaV2.2 channels and its implications for asynchronous neurotransmitter release. Proc Natl Acad Sci U S A 109 E452 PMID: 22308469

Deldicque et al (2011) ER stress induces anabolic resistance in muscle cells through PKB-induced blockade of mTORC1. PLoS One 6 e20993 PMID: 21698202

Meitzen et al (2011) β1-Adrenergic receptors activate two distinct signaling pathways in striatal neurons. J Neurochem 116 984 PMID: 21143600

Li and Burrell (2011) Associative, bidirectional changes in neural signaling utilizing NMDA receptor- and endocannabinoid-dependent mechanisms. Learn Mem 18 545 PMID: 21844187

Earls et al (2010) Dysregulation of presynaptic calcium and synaptic plasticity in a mouse model of 22q11 deletion syndrome. PLoS One 30 15843 PMID: 21106823

Moore et al (2009) Plasticity of burst firing induced by synergistic activation of metabotropic glutamate and acetylcholine receptors. Neuron 61 287 PMID: 19186170

Szikra et al (2009) Calcium homeostasis and cone signaling are regulated by interactions between calcium stores and plasma membrane ion channels. PLoS One 4 e6723 PMID: 19696927

Gerich et al (2009) H(2)O(2)-mediated modulation of cytosolic signaling and organelle function in rat hippocampus. J Neurosci 458 937 PMID: 19430810

Kelm et al (2007) Calcium release from presynaptic internal stores is required for ethanol to increase spontaneous γ-aminobutyric acid release onto cerebellum Purkinje neurons. Cell Cycle 323 356 PMID: 17652632

Bender et al (2006) Two coincidence detectors for spike timing-dependent plasticity in somatosensory cortex. J Neurosci 26 4166 PMID: 16624937

Haeberle et al Swelling-activated Ca2+ channels trigger Ca2+ signals in Merkel cells. MBio 3 e1750 PMID: 18454189


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