Cyclopamine A hedgehog [Hh] signaling pathway and Smo inhibitor

Cyclopamine (CAS 4449-51-8)

Cyclopamine | CAS 4449-51-8 is rated 5.0 out of 5 by 1.
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Synonym: 11-Deoxojervine
Application: A hedgehog [Hh] signaling pathway and Smo inhibitor
CAS Number: 4449-51-8
Purity: ≥98%
Molecular Weight: 411.62
Molecular Formula: C27H41NO2
* Refer to Certificate of Analysis for lot specific data (including water content).
Submit a review for this product and receive 15 CruzCredits

Cyclopamine is a teratogenic Smo inhibitor famous for inducing cyclopia in developing mammalian fetuses. Cyclopia arises from improper differentiation in the fetus, a process heavily regulated by the Hedgehog (Hh) signaling pathway. The proteins Smo and patched mediate cellular response to the Hedgehog protein signal, and aberrant behavior of these proteins can lead to oncogenic states. While cyclopia and fetal failure are the notorious effects of cyclopamine on development, the compound has also been used to suppress and reverse the effects of oncogenic mutations in Smo and patched.


References

1. Taipale, J., et al., 2000. Effects of oncogenic mutations in Smoothened and Patched can be reversed by cyclopamine. Nature. 406(6799): 1005-9. PMID: 10984056
2. Berman, David M., et al., 2002. Medulloblastoma growth inhibition by hedgehog pathway blockade. Science (New York, N.Y.). 297(5586): 1559-61. PMID: 12202832
3. Chen, James K., et al., 2002. Small molecule modulation of Smoothened activity. Proceedings of the National Academy of Sciences of the United States of America. 99(22): 14071-6. PMID: 12391318

Physical State :
Solid
Solubility :
Soluble in ethanol (2 mg/ml), DMF (10 mg/ml), and methanol (7 mg/ml). Insoluble in DMSO, and water.
Storage :
Store at -20° C
Melting Point :
209.82° C (Predicted)
Boiling Point :
~550.8° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.58
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
GY0750000
PubChem CID :
442972
SMILES :
C[C@H]1C[C@@H]2[C@H]([C@H]([C@]3(O2)CC[C@H]4[C@@H]5CC=C6C[C@H](CC[C@@]6([C@H]5CC4=C3C)C)O)C)NC1

Download SDS (MSDS)

Certificate of Analysis

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Cyclopamine  Product Citations

See how others have used Cyclopamine. Click on the entry to view the PubMed entry .

Citations 1 to 9 of 9 total

PMID: # 27015549  Lin, EH. et al. 2016. Oncotarget. 7: 24179-93.

PMID: # 26387793  Li, AS. et al. 2015. Mol. Reprod. Dev. 82: 1015-36.

PMID: # 26370082  Fu, X. et al. 2015. J. Biol. Chem. 290: 26445-56.

PMID: # 26299970  Srikanth, P. et al. 2015. Cell Rep. 12: 1414-29.

PMID: # 26658258  Porcu, G. et al. 2015. PLoS ONE. 10: e0144550.

PMID: # 25486364  Breslin, L. et al. 2014. Cell Cycle. 13: 2773-9.

PMID: # 25305367  Zhou, Q. et al. 2014. Biochim. Biophys. Acta. 1842: 2367-77.

PMID: # 24631215  Zannino, DA. et al. 2014. Dev. Biol. 390: 247-60.

PMID: # 15482598  Sheng, T. et al. 2004. Mol. Cancer. 3: 29.

Citations 1 to 9 of 9 total

Hi We are interested in buying 1mg of Cyclopamine. Can you please provide information regarding the solubility and solvent in which cyclopamine needs to be prepared,

Asked by: Nehaattal
Soluble in ethanol (2 mg/ml), DMF (10 mg/ml), and methanol (7 mg/ml). Insoluble in DMSO, and water.
Answered by: Technical Support
Date published: 2019-04-13

Is this soluble in water?

Asked by: SCchem16
Thank you for your question. This chemical, Cyclopamine (CAS 4449-51-8), is insoluble in water. Ethanol is recommended as it has the best solubility.
Answered by: Chemical Support 2
Date published: 2017-04-20

Is this product cell permeable?

Asked by: SCchem16
Thank you for your question. This chemical, Cyclopamine: sc-200929, is cell permeable.
Answered by: Chemical Support 2
Date published: 2017-04-20

What is the primary target and IC50 value?

Asked by: SCchem16
Thank you for your question. For this chemical, Cyclopamine (CAS 4449-51-8), the primary target is the Hh signaling in Shh-light2 assay with an IC50 value of 20 nM.
Answered by: Chemical Support 2
Date published: 2017-04-20
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Rated 5 out of 5 by from Observed by WB Observed by WB, an increase was observed in the expression of p21 in SW480 cells after treatment with cyclopamine (sc-200929). -SCBT QC
Date published: 2015-01-08
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