Thapsigargin
Catalog #:
IN0067| IN0067-1mg | USD40.0 |
| IN0067-5mg | USD230.0 |
| IN0067-10mg | USD430.0 |
Synonyms: Thapsigargin, THAPSINGARGIN, TG1
IUPAC Name:
[(3S,3aR,4S,6S,6aR,7S,8S,9bS)-6-acetyloxy-4-butanoyloxy-3, 3a-dihydroxy-3,6,9-trimethyl-8-[(Z)-2-methylbut-2-enoyl]oxy-2-oxo-4,5, 6a,7,8,9b-hexahydroazuleno[4,5-b]furan-7-yl] octanoate
Functional Activity:
Thapsigargin is non-competitive inhibitor of a class of enzymes known by the acronym SERCA, which stands for sarco / endoplasmic reticulum Ca2+ ATPase. Structurally, thapsigargin is classified as a sesquiterpene lactone, and is extracted from a plant, Thapsia garganica. It is a tumor promoter in mammalian cells. The anti-malarial drug artemisinin is also a sesquiterpene lactone, leading to a proposal that this class of drugs works by inhibiting the SERCA of malaria parasites such as Plasmodium falciparum; this hypothesis awaits confirmation.
Thapsigargin raises cytosolic calcium concentration by blocking the ability of the cell to pump calcium into the sarcoplasmic and endoplasmic reticula which causes these stores to become depleted. Store-depletion can secondarily activate plasma membrane calcium channels, allowing an influx of calcium into the cytosol.
Technical Data:
M.Wt: 650.75
Formula: C34H50O12
Solubility: Soluble to 100mM in DMSO and 5mM in ethanol
Purity: >98%
Storage: Dessicate at -20°C
CAS No.: 67526-95-8
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References for Thapsigargin :
1. Vander Griend, D. J., Antony, L., Dalrymple, S. L., Xu, Y., Christensen, S. B., Denmeade, S. R., and Isaacs, J. T. Amino acid containing thapsigargin analogues deplete androgen receptor protein via synthesis inhibition and induce the death of prostate cancer cells. Mol Cancer Ther, 8: 1340-1349, 2009.
2. Lee, T. J., Lee, J. T., Kim, S. H., Choi, Y. H., Song, K. S., Park, J. W., and Kwon, T. K. Overexpression of Par-4 enhances thapsigargin-induced apoptosis via down-regulation of XIAP and inactivation of Akt in human renal cancer cells. J Cell Biochem, 103: 358-368, 2008.
3. Lee, D. I., Sumbilla, C., Lee, M., Natesavelalar, C., Klein, M. G., Ross, D. D., Inesi, G., and Hussain, A. Mechanisms of resistance and adaptation to thapsigargin in androgen-independent prostate cancer PC3 and DU145 cells. Arch Biochem Biophys, 464: 19-27, 2007.
4. O'Neill, J. P., Velalar, C. N., Lee, D. I., Zhang, B., Nakanishi, T., Tang, Y., Selaru, F., Ross, D., Meltzer, S. J., and Hussain, A. Thapsigargin resistance in human prostate cancer cells. Cancer, 107: 649-659, 2006.
5. Denmeade, S. R., Jakobsen, C. M., Janssen, S., Khan, S. R., Garrett, E. S., Lilja, H., Christensen, S. B., and Isaacs, J. T. Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer. J Natl Cancer Inst, 95: 990-1000, 2003.
6. Yamaguchi, H., Bhalla, K., and Wang, H. G. Bax plays a pivotal role in thapsigargin-induced apoptosis of human colon cancer HCT116 cells by controlling Smac/Diablo and Omi/HtrA2 release from mitochondria. Cancer Res, 63: 1483-1489, 2003.
