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Submit Review20(S)-Hydroxycholesterol
Description: Allosteric activator of Hedgehog (Hh) signaling; induces Smo accumulation
Chemical Name: (3β)-Cholest-5-ene-3,20-diol
Purity: ≥95% (HPLC)
Biological Activity for 20(S)-Hydroxycholesterol
20(S)-Hydroxycholesterol is an allosteric activator of the Hedgehog signaling pathway Smoothened (Smo) oncoprotein; binds at a site distinct from the canonical cyclopamine binding site. Activates Hedgehog (Hh) signaling (EC50 ~ 3μM for induction of Hh reporter gene transcription in in NIH 3T3 cells). Induces Smo accumulation in primary cilia; also exhibits osteogenic activity and activates the liver X receptor (LXR).
Technical Data for 20(S)-Hydroxycholesterol
| M. Wt | 402.65 |
| Formula | C27H46O2 |
| Storage | Store at -20°C |
| Purity | ≥95% (HPLC) |
| CAS Number | 516-72-3 |
| PubChem ID | 440711 |
| InChI Key | MCKLJFJEQRYRQT-APGJSSKUSA-N |
| Smiles | O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@]4([H])[C@](O)(C)CCCC(C)C |
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 20(S)-Hydroxycholesterol
| Solvent | Max Conc. mg/mL | Max Conc. mM | |
|---|---|---|---|
| Solubility | |||
| ethanol | 40.26 | 100 |
Preparing Stock Solutions for 20(S)-Hydroxycholesterol
The following data is based on the product molecular weight 402.65. 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 |
|---|---|---|---|
| 1 mM | 2.48 mL | 12.42 mL | 24.84 mL |
| 5 mM | 0.5 mL | 2.48 mL | 4.97 mL |
| 10 mM | 0.25 mL | 1.24 mL | 2.48 mL |
| 50 mM | 0.05 mL | 0.25 mL | 0.5 mL |
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Product Datasheets for 20(S)-Hydroxycholesterol
References for 20(S)-Hydroxycholesterol
References are publications that support the biological activity of the product.
Nachtergaele et al (2012) Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat.Chem.Biol. 8 211 PMID: 22231273
Dwyer et al (2007) Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells J.Biol.Chem. 282 8959 PMID: 17200122
Nedelcu et al (2013) Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat.Chem.Biol. 9 557 PMID: 23831757
If you know of a relevant reference for 20(S)-Hydroxycholesterol, please let us know.
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Keywords: 20(S)-Hydroxycholesterol, 20(S)-Hydroxycholesterol supplier, Oxysterols, allosteric, activators, positive, modulators, Smo, smoothened, Hedgehog, signaling, pathways, Signaling, Stem, Cell, Smoothened, Receptors, 4474, Tocris Bioscience
2 Citations for 20(S)-Hydroxycholesterol
Citations are publications that use Tocris products. Selected citations for 20(S)-Hydroxycholesterol include:
Craig B et al (2017) Metabolic origins of spatial organization in the tumor microenvironment. Proc Natl Acad Sci U S A 114 2934-2939 PMID: 28246332
Lucia et al (2020) HDL inhibits endoplasmic reticulum stress-induced apoptosis of pancreatic β-cells in vitro by activation of Smoothened. J Lipid Res 61 492-504 PMID: 31907205
Do you know of a great paper that uses 20(S)-Hydroxycholesterol from Tocris? Please let us know.
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