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20 (S) -Hydroxycholesterol

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 Specifications

CAS Number

[516-72-3]

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

Available Sizes

Curated Selection

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