516-72-3 Usage
Description
20ALPHA-HYDROXYCHOLESTEROL, also known as 20(S)-hydroxy Cholesterol, is an oxysterol that is a cholesterol oxidation product with a hydroxy group substituted at position 20. It is a metabolite of cholesterol and has cytotoxicity effects. As an allosteric agonist of the smoothened (Smo) receptor, it activates the hedgehog (Hh) signaling pathway, which is necessary for normal Hh signaling. It also stimulates osteogenic differentiation of pluripotent bone marrow stromal cells through Hh and Notch signaling. 20ALPHA-HYDROXYCHOLESTEROL is a white solid.
Uses
Used in Pharmaceutical Industry:
20ALPHA-HYDROXYCHOLESTEROL is used as a cytotoxic agent for its cholesterol oxidation product properties, which can have potential applications in the development of drugs targeting specific cellular pathways.
Used in Research Applications:
20ALPHA-HYDROXYCHOLESTEROL is used as a research tool for studying the hedgehog (Hh) signaling pathway, Smo receptor activation, and its role in various cellular processes, including osteogenic differentiation of pluripotent bone marrow stromal cells.
Used in Drug Development:
20ALPHA-HYDROXYCHOLESTEROL is used as a lead compound in the development of drugs targeting the hedgehog signaling pathway, which is involved in various diseases, including cancer.
Used in Cell Biology:
20ALPHA-HYDROXYCHOLESTEROL is used as a reagent in cell biology experiments to investigate the effects of Hh signaling modulation on cell differentiation and proliferation.
References
1) Janowski?et al. (1996),?An oxysterol signaling pathway mediated by the nuclear receptor LXR7alpha; Nature,?383?728
2) Kha?et al. (2004),?Oxysterols regulate differentiation of mesenchymal stem cells: Pro-bone and Anti-fat: J. Bone Min. Res.,?19?830
3) Kim?et al. (2010),?Osteogenic oxysterol, 20(S)-hydroxycholesterol, induces notch target gene expression in bone marrow stromal cells; J. Bone Miner. Res.,?25?7823
4) Dwyer?et al. (2007),?Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells; J. Biol. Chem.,?282?8959
5) Nedelcu?et al. (2013);?Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling; Nat. Chem. Biol.,?9?557
6) Cheng?et al. (2021);?A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes; Nat. Chem. Biol.,?17?1271
Check Digit Verification of cas no
The CAS Registry Mumber 516-72-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,1 and 6 respectively; the second part has 2 digits, 7 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 516-72:
(5*5)+(4*1)+(3*6)+(2*7)+(1*2)=63
63 % 10 = 3
So 516-72-3 is a valid CAS Registry Number.
InChI:InChI=1/C27H46O2/c1-18(2)7-6-14-27(5,29)24-11-10-22-21-9-8-19-17-20(28)12-15-25(19,3)23(21)13-16-26(22,24)4/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t20-,21-,22-,23-,24-,25-,26-,27+/m0/s1
516-72-3Relevant articles and documents
Preparation of oxysterols by c–h oxidation of dibromocholestane with ru(Bpga) catalyst
Doiuchi, Daiki,Fujii, Yui,Hirai, Go,Igawa, Kazunobu,Makino, Kana,Takeda, Daiki,Tomooka, Katsuhiko,Uchida, Tatsuya,Yoritate, Makoto
, (2022/01/04)
Seven mono-and dihydroxycholesterols were prepared by direct C–H oxidation of the cholestane skeleton with a recently developed Ru(Bpga) catalyst (Ru(Bpga) = [RuCl (bpga) (PPh3 )] Cl; bpga = 2-(bis(pyridin-2-ylmethyl)amino)-N-(2,6-dimethylphenyl)acetamide)). Due to the high selectivity of the Ru(Bpga) complex for tertiary C–H, the reaction afforded a mixture of 25-, 20-, 17-, and 14-oxygenated cholesterols that could be easily separated by high-performance liquid chromatography. These results suggest that late-stage C–H oxidation could be a viable strategy for preparing candidate metabolites of biologically important molecules.
Glucal-conjugated sterols as novel vascular leakage blocker: Structure-activity relationship focusing on the C17-side chain
Kim, Kyeojin,Maharjan, Sony,Lim, Changjin,Kim, Nam-Jung,Agrawal, Vijayendra,Han, Young Taek,Lee, Sujin,An, Hongchan,Yun, Hwayoung,Choi, Hyun-Jung,Kwon, Young-Guen,Suh, Young-Ger
, p. 184 - 194 (2014/03/21)
A series of glucal-conjugated sterols as novel vascular leakage blocker were identified through design, synthesis and biologically evaluation. In addition, the structure-activity relationship (SAR) of the glucal-conjugated sterols focusing on the C17-side chain was also established. The sterol analogs linked with the rigid C17-side chain side chains exhibited potent cell survival activities. In particular, analog 21l, which possesses a cyclopentyl oxime moiety, was shown to have excellent pharmacological effects on retinal vascular leakage in a diabetic mouse model.
NOVEL VASCULAR LEAK INHIBITOR
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Page/Page column 41-42, (2012/09/21)
The present disclosure relates to a novel vascular leakage inhibitor. The novel vascular leakage inhibitor of the present disclosure inhibits the apoptosis of vascular endothelial cells, inhibits the formation of actin stress fibers induced by VEGF, enhances the cortical actin ring structure, and improves the stability of the tight junctions (TJs) between vascular cells, thereby inhibiting vascular leakage. The vascular leakage inhibitor of the present disclosure has the activity of not only reducing vascular permeability but also recovering the integrity of damaged blood vessels. Accordingly, the vascular leakage inhibitor of the present disclosure can prevent or treat various diseases caused by vascular leakage. Since the vascular leakage inhibitor of the present disclosure is synthesized from commercially available or easily synthesizable cholesterols, it has remarkably superior feasibility of commercial synthesis.
