20 (S) -Hydroxycholesterol

• Description:

  20 (S) -Hydroxycholesterol (20α-Hydroxycholesterol) is an allosteric activator that selectively targets the Smoothened (Smo) of the Hedgehog pathway with an EC50 of ~30 μM (Hedgehog) . 20 (S) -Hydroxycholesterol binds to the extracellular cysteine-rich domain (CRD) of Smo in a stereoselective manner, activating downstream Gli transcription factors (without inducing transcription of receptor genes in the Wnt pathway) . 20 (S) -Hydroxycholesterol enhances osteogenic differentiation of bone marrow stromal cells and synergistically activates the Raf/MEK/ERK pathway with Simvastatin (HY-17502) to promote bone regeneration. 20 (S) -Hydroxycholesterol can be used to study the mechanisms of developmental biology, oncology, bone, and angiogenesis[1][2][3].

• Product Name Alternative:

  20α-Hydroxycholesterol

• UNSPSC:

  12352211

• Hazard Statement:

  H302, H315, H319, H335

• Target:

  Endogenous Metabolite; Smo

• Type:

  Natural Products

• Related Pathways:

  Metabolic Enzyme/Protease; Stem Cell/Wnt

• Applications:

  Cancer-programmed cell death

• Field of Research:

  Cancer; Metabolic Disease; Cardiovascular Disease

• Assay Protocol:

  https://www.medchemexpress.com/20-s-hydroxycholesterol.html

• Purity:

  99.29

• Solubility:

  DMSO : 12.5 mg/mL (ultrasonic)

• Smiles:

  C[C@@]1([C@@]2([H])[C@@](C)(O)CCCC(C)C)[C@](CC2)([H])[C@@](CC=C3[C@@]4(CC[C@H](O)C3)C)([H])[C@]4([H])CC1

• Molecular Formula:

  C27H46O2

• Molecular Weight:

  402.65

• Precautions:

  H302, H315, H319, H335

• References & Citations:

  [1]Nachtergaele S, et al. Oxysterols are allosteric activators of the oncoprotein Smoothened. Nat Chem Biol. 2012 Jan 8;8 (2) :211-20.|[2]Huang Y, et al. 20 (S) -hydroxycholesterol and simvastatin synergistically enhance osteogenic differentiation of marrow stromal cells and bone regeneration by initiation of Raf/MEK/ERK signaling. J Mater Sci Mater Med. 2019 Jul 19;30 (8) :87.|[3]Nedelcu D, et al, Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling. Nat Chem Biol. 2013 Sep;9 (9) :557-64.

• Shipping Conditions:

  Room Temperature

• Storage Conditions:

  -20°C, 3 years; 4°C, 2 years (Powder)

• Scientific Category:

  Natural Products

• Clinical Information:

  No Development Reported

• Isoform:

  Human Endogenous Metabolite

• CAS Number:

  516-72-3