T4557
Thapsigargicin
≥90%
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About This Item
Empirical Formula (Hill Notation):
C32H46O12
CAS Number:
Molecular Weight:
622.70
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:
Assay
≥90%
storage temp.
−20°C
SMILES string
CCCCCC(=O)O[C@@H]1[C@@H](OC(=O)\C(C)=C/C)C(C)=C2[C@@H]3OC(=O)[C@@](C)(O)[C@@]3(O)[C@H](C[C@](C)(OC(C)=O)[C@@H]12)OC(=O)CCC
InChI
1S/C32H46O12/c1-9-12-13-15-22(35)41-26-24-23(18(5)25(26)42-28(36)17(4)11-3)27-32(39,31(8,38)29(37)43-27)20(40-21(34)14-10-2)16-30(24,7)44-19(6)33/h11,20,24-27,38-39H,9-10,12-16H2,1-8H3/b17-11-/t20-,24+,25-,26-,27-,30-,31+,32+/m0/s1
InChI key
LXWLOFYIORKNSA-FFOGNQQCSA-N
Application
Thapsigargicin has been assayed as a potential inhibitor of S. mansoni ATPdiphosphohydrolases (ATPDase)2.
Biochem/physiol Actions
Thapsigargicin is known to mobilize intracellular Ca2+. Furthermore, studies have reported that thapsigargicin can induce the release of histamine from pulmonary, mesentery and cardiac mast cells of rats3.
Other Notes
Less potent and less hydrophobic analog of thapsigargin.
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Regulatory Information
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H Hakii et al.
Journal of cancer research and clinical oncology, 111(3), 177-181 (1986-01-01)
Thapsigargin, a hexaoxygenated tetraacylated sesquiterpene lactone, induced irritation of mouse ear and histidine decarboxylase (HDC) activity in mouse skin, but it did not induce ornithine decarboxylase in mouse skin or adhesion of human promyelocytic leukemia (HL-60) cells. Although thapsigargin did
Fabio Blandini et al.
Clinical neuropharmacology, 32(3), 133-139 (2008-11-04)
Long-term treatment of Parkinson disease (PD) is frequently associated with l-3,4-dihydroxyphenylalanine (L-DOPA)-induced dyskinesias (LIDs). L-DOPA-induced dyskinesias are likely due to changes in the signal transduction pathways, at the striatal level, related to pulsatile stimulation of dopamine receptors. We investigated whether
Regalla Kumarswamy et al.
European heart journal, 33(9), 1067-1075 (2012-03-01)
Impaired myocardial sarcoplasmic reticulum calcium ATPase 2a (SERCA2a) activity is a hallmark of failing hearts, and SERCA2a gene therapy improves cardiac function in animals and patients with heart failure (HF). Deregulation of microRNAs has been demonstrated in HF pathophysiology. We
S Länge et al.
Biochimica et biophysica acta, 1278(2), 191-196 (1996-01-31)
Caffeine inhibits 45Ca2+ sequestration by subplasmalemmal calcium stores ('alveolar sacs') of low thapsigargicin sensitivity which we have isolated from the ciliated protozoan, Paramecium tetraurelia. Inhibition depends on caffeine concentration, with an IC50 of 31.8 mM. According to kinetic evaluation this
Dóra Hargitai et al.
Respiratory physiology & neurobiology, 170(1), 67-75 (2009-12-10)
The extracellular pH, sodium and divalent cation concentrations influence the ATP-induced changes in cytosolic Ca(2+) concentration ([Ca(2+)](i)). This elevation of [Ca(2+)](i) and activation of Ca(2+)-dependent Cl(-) channels represent a possible therapeutic approach in cystic fibrosis (CF). We investigated the changes
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