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Submit ReviewCyclopamine
Description: Inhibitor of Hedgehog (Hh) signaling
Chemical Name: (2'R,3S,3'R,3'aS,6'S,6aS,6bS,7'aR,11aS,11bR)-1,2,3,3'a,4,4',5',6,6',6a,6b,7,7',7'a,8,11,11a,11b-Octadecahydro-3',6',10,11b-tetramethylspiro[9H-benzo[a]fluorene-9,2'(3'H)-furo[3,2-b]pyridin]-3-ol
Purity: ≥97% (HPLC)
Biological Activity for Cyclopamine
Cyclopamine is an inhibitor of hedgehog (Hh) signaling, likely via direct inhibition of Smoothened, the accessory protein to the putative Hh receptor Patched. Anticancer and teratogenic in vivo. Depletes stem-like cancer cells in glioblastoma and blocks tumor engraftment. Can also be used to induce differentiation of human embryonic stem cells (hESCs) into hormone-expressing endocrine cells.
Technical Data for Cyclopamine
| M. Wt | 411.63 |
| Formula | C27H41NO2 |
| Storage | Desiccate at -20°C |
| Purity | ≥97% (HPLC) |
| CAS Number | 4449-51-8 |
| PubChem ID | 442972 |
| InChI Key | QASFUMOKHFSJGL-LAFRSMQTSA-N |
| Smiles | O[C@H](C2)CC[C@@]1(C)C2=CC[C@]([C@@]([H])3CC[C@@]54O[C@@](C[C@H](C)CN6)([H])[C@]6([H])[C@H]5C)([H])[C@@]([H])1CC3=[C@@]4C |
The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.
Tocris products are intended for laboratory research use only, unless stated otherwise.
Solubility Data for Cyclopamine
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 2.06 | 5 |
Preparing Stock Solutions for Cyclopamine
The following data is based on the product molecular weight 411.63. Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 0.05 mM | 48.59 mL | 242.94 mL | 485.87 mL |
| 0.25 mM | 9.72 mL | 48.59 mL | 97.17 mL |
| 0.5 mM | 4.86 mL | 24.29 mL | 48.59 mL |
| 2.5 mM | 0.97 mL | 4.86 mL | 9.72 mL |
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Product Datasheets for Cyclopamine
References for Cyclopamine
References are publications that support the biological activity of the product.
Chen et al (2002) Inhibition of hedgehog signaling by direct binding of cyclopamine to smoothened. Genes Dev. 16 2743 PMID: 12414725
Scott (2003) Cancer: a twist in a hedgehog's tale. Nature 425 780 PMID: 14574396
Bar et al (2007) Cyclopamine-mediated hedgehog pathway inhibition depletes stem-like cancer cells in glioblastoma. Stem Cells 25 2524 PMID: 17628016
D'Amour et al (2006) Production of pancreatic hormone-expressing endocrine cells from human embryonic stem cells. Nat.Biotechnol. 24 1392 PMID: 17053790
If you know of a relevant reference for Cyclopamine, please let us know.
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Keywords: Cyclopamine, Cyclopamine supplier, inhibitors, inhibits, hedgehog, Hh, signaling, Signalling, Hedgehog, stem, cells, Smo, smoothened, antagonist, Signaling, Stem, Cell, Smoothened, Receptors, Cancer, Cells, ESCs, and, iPSC, 1623, Tocris Bioscience
8 Citations for Cyclopamine
Citations are publications that use Tocris products. Selected citations for Cyclopamine include:
Yuan et al (2016) Ciliary IFT80 balances canonical versus non-canonical hedgehog signalling for osteoblast differentiation. Stem Cells Int 7 11024 PMID: 26996322
Atzmon et al (2018) Drug Screening Identifies Sigma-1-Receptor as a Target for the Therapy of VWM Leukodystrophy. Front Mol Neurosci 11 336 PMID: 30279648
Yan et al (2017) Chemical inhibition reveals differential requirements of signaling pathways in krasV12- and Myc-induced liver tumors in transgenic zebrafish. Sci Rep 7 45796 PMID: 28378824
Rodrigues (2017) Integration of Shh and Fgf signaling in controlling Hox gene expression in cultured limb cells. PNAS 114 3139 PMID: 28270602
Atwood et al (2013) GLI activation by atypical protein kinase C Ι/λ regulates the growth of basal cell carcinomas. Nat Commun 494 484 PMID: 23446420
Zou et al (2015) Sonic hedgehog produced by bone marrow-derived mesenchymal stromal cells supports cell survival in myelodysplastic syndrome. Sci Signal 2015 957502 PMID: 25861282
Moisan et al (2015) White-to-brown metabolic conversion of human adipocytes by JAK inhibition. Nat Cell Biol 17 57 PMID: 25487280
Kumar et al (2015) Generation of an expandable intermediate mesoderm restricted progenitor cell line from human pluripotent stem cells. Elife 4 PMID: 26554899
Do you know of a great paper that uses Cyclopamine from Tocris? Please let us know.
Reviews for Cyclopamine
Average Rating: 5 (Based on 1 Review.)
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Modulators of Hh signalling and stress fibres.
By
Anonymous on 11/09/2019
Assay Type: In Vitro
Species: Human
Cell Line/Tissue: Primary OPCs
Modulators of Hh signalling and stress fibres. Cyclopamine (Tocris Bioscience, 1623) was dissolved in ethanol and DMSO. The final concentration used for cells was 5 mM of cyclopamine.
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