| Identification | More | [Name]
THAPSIGARGIN | [CAS]
67526-95-8 | [Synonyms]
THAPSIGARGIN
Thapsigargin,97%
Thapsigargin (TG)
THAPSIGARGIN USP/EP/BP
InSolution? Thapsigargin
Thapsigargin, FroM Thapsia garganica
Azuleno[4,5-b]furan octanoic acid deriv.
Thapsigargin, 99%, from Thapsia garganica
Thapsigargin - CAS 67526-95-8 - Calbiochem
Thapsigargin (Synonyms: Thapsigargin (TG))
InSolution Thapsigargin - CAS 67526-95-8 - Calbiochem
Thapsigargin Azuleno[4,5-b]furan octanoic acid deriv
Octanoic acid [(3S)-6α-acetoxy-2,3,3a,4,5,6,6aα,7,8,9bβ-decahydro-3β,3aα-dihydroxy-3,6,9-trimethyl-8β-[[(Z)-2-methyl-1-oxo-2-butenyl]oxy]-2-oxo-4β-(1-oxobutoxy)azuleno[4,5-b]furan]-7α-yl ester
(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
Octanoic Acid (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 Ester
Octanoic Acid [3S-[3α,3aβ,4α,6β,6aβ,7β,8α(Z),9bα]]-6-(Acetyloxy)-2,3,3a,4,5,6,6a,7,8,9b-decahydro-3,3a-dihydroxy-3,6,9-triMethyl-8-[(2-Methyl-1-oxo-2-butenyl)oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]furan-7-yl Ester
Octanoic acid, (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-buten-1-yl]oxy]-2-oxo-4-(1-oxobutoxy)azuleno[4,5-b]f
uran-7-yl ester | [EINECS(EC#)]
614-076-3 | [Molecular Formula]
C34H50O12 | [MDL Number]
MFCD00083511 | [Molecular Weight]
650.75 | [MOL File]
67526-95-8.mol |
| Chemical Properties | Back Directory | [Appearance]
colourless film | [Boiling point ]
597.77°C (rough estimate) | [density ]
1.1521 (rough estimate) | [refractive index ]
1.6390 (estimate) | [RTECS ]
RH0325700 | [storage temp. ]
−20°C
| [solubility ]
DMSO: soluble
| [form ]
liquid or film
| [pka]
10.57±0.70(Predicted) | [color ]
Colorless | [biological source]
plant (Thapsia garganica) | [Sensitive ]
Light Sensitive | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 1 week. | [InChIKey]
IXFPJGBNCFXKPI-FSIHEZPISA-N | [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 | [CAS DataBase Reference]
67526-95-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,T | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R42:May cause sensitization by inhalation. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [RIDADR ]
UN 2811 6.1/PG 2
| [WGK Germany ]
3
| [HS Code ]
29181990 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Resp. Sens. 1
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Description]
In cells, sarco/endoplasmic calcium ATPases (SERCAs) transport free calcium into the sarcoplasmic and endoplasmic reticula, lowering intracellular calcium levels to stop signaling through this cation. Thapsigargin is a non-competitive, cell permeable inhibitor of calcium transport by SERCAs (IC50 values are cell type-dependent and range from ~2-80 nM).1,2 Inhibition of SERCAs leads to an increase in intracellular calcium, which has been linked to cell activation, release of histamine from mast cells, and increased proliferation of certain types of cancer cells.1,3,4 In vivo, thapsigargin and related sesquiterpene lactones have anti-inflammatory and anti-cancer effects.5,6 | [Chemical Properties]
THAPSIGARGIN is colourless film
| [Uses]
Reagent for defining and manipulating intracellular calcium pools. | [Uses]
THAPSIGARGIN is a widely used inhibitor of the ubiquitous sarco-endoplasmic reticulum Ca(2+)-ATPases in mammalian cells. It acts as a potent, cell-permeable, IP3-independent intracellular calcium releaser that blocks the transient increase in intracellular Ca2+ induced by angiostatin and endostatin. It induces apoptosis by disrupting intracellular free Ca2+ levels.
| [Definition]
THAPSIGARGIN is an organic heterotricyclic compound that is a hexa-oxygenated 6,7-guaianolide isolated fron the roots of Thapsia garganica L., Apiaceae. A potent skin irritant, it is used in traditional medicine as a counter-irritant. Thapsigargi inhibits Ca2+-transporting ATPase mediated uptake of calcium ions into sarcoplasmic reticulum and is used in experimentation examining the impacts of increasing cytosolic calcium concentrations.
| [Biological Activity]
Potent inhibitor of sarco-endoplasmic reticulum Ca 2+ -ATPases. | [Biochem/physiol Actions]
Thapsigargin is an effective inhibitor of calcium ion pumps located on sarcoplasmic reticulum (SR) and endoplasmic reticulum (ER) microsomes of skeletal, cardiac, muscle and brain tissues. The inhibition of calcium ion pumps causes intracellular increase of calcium ion levels. It was found that thapsigargin at 100 nM concentration effectively inhibited the SR Ca2+- adenosine triphosphatase (ATPase) in cardiac and skeletal muscles. Thapsigargin was also reported to be effective in blocking autophagy by interfering with the autophagosome-lysosome fusion. | [storage]
Store at -20°C | [Mode of action]
The actual mechanism of action of thapsigargin is thought actually to block calcium channels in an open conformation that results in excess calcium entry from outside the cell. Excess calcium activates DNAses and precipitates the natural death sequence of the cells.Scientists are now thinking of modifying thapsigargin in such a way thatit will kill prostate cells preferentially and will not penetrate healthy cells elsewhere in the body.At the same time, they are determining whether this drug can also induce cell death in breast cancer cells. | [References]
1) Treiman et al. (1998), A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca(2+)-ATPases; Trends Pharmacol. Sci., 19 131
2) Zhou et al. (2009), Autophagy-mediated insulin receptor down-regulation contributes to endoplasmic reticulum stress-induced insulin resistance; Mol. Pharmacol., 76 596 |
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