Cyclopamine

Pricing Availability Delivery Time Qty
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)
Datasheet
Citations (6)
Literature

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
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.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
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.

Select a batch to recalculate based on the batch molecular weight:
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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Safety Datasheet

References

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


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View Related Products by Product Action

View all Hedgehog Signaling Inhibitors

Keywords: Cyclopamine, supplier, inhibitors, inhibits, hedgehog, Hh, signaling, Signalling, Hedgehog, stem, cells, Smo, smoothened, antagonist, Hedgehog, Signaling, Tocris Bioscience

6 Citations for Cyclopamine

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

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

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


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

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Literature in this Area

Cancer

Cancer Research Product Guide

A collection of over 750 products for cancer research, the guide includes research tools for the study of:

  • Cancer Metabolism
  • Epigenetics in Cancer
  • Receptor Signaling
  • Cell Cycle and DNA Damage Repair
  • Angiogenesis
  • Invasion and Metastasis
Stem Cells

Stem Cells Scientific Review

Written by Kirsty E. Clarke, Victoria B. Christie, Andy Whiting and Stefan A. Przyborski, this review provides an overview of the use of small molecules in the control of stem cell growth and differentiation. Key signaling pathways are highlighted, and the regulation of ES cell self-renewal and somatic cell reprogramming is discussed. Compounds available from Tocris are listed.

Pathways for Cyclopamine

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