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Cat.No. 1623 - Cyclopamine | C27H41NO2 | CAS No. 4449-51-8
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)
Citations (6)

Biological Activity

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

M. Wt 411.63
Formula C27H41NO2
Storage Desiccate at -20°C
Purity ≥97% (HPLC)
CAS Number 4449-51-8
PubChem ID 442972
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
ethanol 2.06 5

Preparing Stock Solutions

The following data is based on the product molecular weight 411.63. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 2.43 mL 12.15 mL 24.29 mL
5 mM 0.49 mL 2.43 mL 4.86 mL
10 mM 0.24 mL 1.21 mL 2.43 mL
50 mM 0.05 mL 0.24 mL 0.49 mL

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Product Datasheets

Certificate of Analysis / Product Datasheet
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References are publications that support the products' biological activity.

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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6 Citations for Cyclopamine

Citations are publications that use Tocris products. Selected citations for Cyclopamine include:

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

Rodrigues (2017) Integration of Shh and Fgf signaling in controlling Hox gene expression in cultured limb cells. PNAS 114 3139 PMID: 28270602

Yuan et al (2016) Ciliary IFT80 balances canonical versus non-canonical hedgehog signalling for osteoblast differentiation. Stem Cells Int 7 11024 PMID: 26996322

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

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

Do you know of a great paper that uses Cyclopamine from Tocris? If so please let us know.

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