Stemgent Stemolecule Cyclopamine

Code: 04-0022-base
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Stemolecule Cyclopamine is a steroid alkaloid isolated from the corn lily (Veratrum californicum) and originally identified as a teratogenic agent1. Cyclopamine has since been identified as a specific inhibitor of hedgehog signaling by direct binding to the heptahelical bundle of Smoothened2. Hedgehog signaling is involved in embryogenesis as well as cancer progression3. Cycoplamine has been utilized as a small molecule inducer of stem cell differentiation towards definitive endoderm pancreatic islet cells, as a modulator of cell proliferation, and as an anticancer drug4-6.

Product Name

Stemolecule Cyclopamine

Catalog Number

04-0022

Size

2 mg

Alternate Name(s)

(3S,3'R,3'aS,6'S,6aS,6bS,7'aR,9R,11aS,11bR)-3',6',10,11b tetramethylspiro[2,3,4,6,6a,6b,7,8,11,11a-decahydro-1H-benzo[a]fluorene-9,2'-3a,4,5,6,7,7a-hexahydro-3H-furo[3,2-b]pyridine]-3-ol

Chemical Formula

C27H41NO2

Molecular Weight

411.62

CAS Number

4449-51-8

Purity

Greater than 99% by TLC analysis

Formulation

White crystalline solid or clear solid film at bottom of vial

Solubility

For a 10 mM concentrated stock solution of Cyclopamine, reconstitute the compound by adding 485.9 µL of DMSO to the entire contents of the vial. If precipitate is observed, warm the solution to 37 °C for 2 to 5 minutes. For cell culture, the media should be prewarmed prior to adding the reconstituted compound. Note: for most cells, the maximum tolerance to DMSO is less than 0.5%. This molecule is reported to be soluble in DMSO at 100 mM, ethanol at 49 mM, and methanol at 17 mM.

Storage and Stability

Store powder at 4 °C protected from light. Information about the stability of Stemolecules in solution is largely not available. As a general guideline, we recommend that stock solution be freshly made and stored in aliquots at −20 °C. The effect of storage of stock solutions should be verified for each application.

Quality Control

The purity of Cyclopamine was determined by TLC analysis. The accurate mass was determined by mass spectrometry. Cellular toxicity of Cyclopamine was tested on mouse embryonic stem cells

Specification Sheets

Safety Data Sheets

  1. Gaffield, W., Incardona, J.P., Kapur, R.P., and Roelink, H. A looking glass perspective: thalidomide and cyclopamine. Cell Mol Biol (Noisy-le-grand) 45: 579-588 (1999).
  2. Chen, J.K., Taipale, J., Cooper, M.K., and Beachy, P.A. Inhibition of Hedgehog signaling by direct binding of cyclopamine to Smoothened. Genes Dev 16: 2743-2748 (2002).
  3. Jiang, J., and Hui, C.C. Hedgehog signaling in development and cancer. Dev Cell 15: 801-812 (2008).
  4. D'Amour, K.A., Bang, A.G., Eliazer, S., Kelly, O.G., Agulnick, A.D., Smart, N.G., Moorman, M.A., Kroon, E., Carpenter, M.K., and Baetge, E.E. Production of pancreatic hormone-expressing endocrine cells from human embryonic stem cells. Nat Biotechnol 24: 1392-1401 (2006).
  5. Gallo, R., Grieco, F.A., Marselli, L., Ferretti, E., Gulino, A., Marchetti, P., and Dotta, F. Hedgehog signaling during expansion of human pancreatic islet-derived precursors. Ann N Y Acad Sci 1150: 43-45 (2008).
  6. Xu, F.G., Ma, Q.Y., and Wang, Z. Blockade of hedgehog signaling pathway as a therapeutic strategy for pancreatic cancer. Cancer Lett 283: 119-124 (2009).

Additional Publications

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