20380-11-4 Usage
Description
5,25R-Cholesten-3beta,26-diol, also known as 27-Hydroxycholesterol, is an endogenous oxysterol metabolite derived from cholesterol through the action of sterol 27-hydroxylase enzyme. It possesses multiple biological functions, including acting as a selective estrogen receptor modulator (SERM) and as an agonist of the liver X receptor (LXR). Elevated concentrations of 27-Hydroxycholesterol have been observed in patients with Alzheimer's disease and mild cognitive impairment.
Uses
Used in Pharmaceutical Industry:
5,25R-Cholesten-3beta,26-diol is used as a potential therapeutic target for the development of drugs to treat breast cancer. It has been implicated in limiting the effectiveness of aromatase inhibitors in the treatment of breast cancer, and its production by the enzyme CYP27A1 has been linked to a high cholesterol and breast cancer connection.
Used in Research Applications:
5,25R-Cholesten-3beta,26-diol is used as a research tool to study its inhibitory effect on hepatic lipid accumulation, as a liver X receptor (LXR) ligand in breast cancer cell lines, and as a control in liquid chromatography with tandem mass spectrometry (LC-MS-MS) for the quantitation of 25-OHC in jejunum samples.
Used in Cholesterol and Fatty Acid Metabolism:
5,25R-Cholesten-3beta,26-diol is used as a ligand for liver X receptors (LXRα and LXRβ), which are nuclear hormone receptors that induce the expression of genes involved in cholesterol and fatty acid metabolism. It activates LXRα and LXRβ in vitro with EC50 values of 85 and 71 nM, respectively, and is a potent suppressor of cholesterol biosynthesis.
Used in Bile Synthesis:
5,25R-Cholesten-3beta,26-diol is used as a substrate for bile synthesis, playing a crucial role in the regulation of cholesterol homeostasis in the body.
Mode of action
27-Hydroxycholesterol is an endogenous metabolite of cholesterol produced by the hydroxylation of the carbon at position 27 by the enzyme sterol 26-hydroxylase, mitochondrial (CYP27A1). Some neoplasms produce excess of 27-hydroxycholesterol (27HC) or inhibit its catabolism, and high cholesterol levels are correlated with elevated levels of 27HC; under these conditions, 27HC may have deleterious selective estrogen receptor modulator (SERM) and liver X receptor (LXR) agonistic activities. As a SERM, 27HC binds to and prevents the activation of estrogen receptors (ERs) in the vasculature. This prevents ER-mediated vasodilation and abrogates the cardiovascular protective effects of estrogen. However, 27HC binds to and activates ERs and LXRs in breast tissue, which stimulates ER-dependent breast cancer cell growth and metastasis.pubchem.ncbi.nlm.nih.gov/compound/27-Hydroxycholesterol
References
1) Heverin et al. (2004), Changes in the levels of cerebral and extracerebral sterols in the brains of patients with Alzheimer's disease; J. Lipid Res.,?45?1862) Shafaati et al. (2011), Marked accumulation of 27-hydroxycholesterol in the brains of Alzheimer's patients with the Swedish APP 670-671 mutation; J. Lipid Res.,?52?10043) Umetani et al. (2007), 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen; Nature Medicine,?13?11854) Fu et al. (2001), 27-Hydroxycholesterol is an endogenous ligand for liver X receptor in cholesterol-loaded cells; J. Biol.Chem.,?276?38378
Check Digit Verification of cas no
The CAS Registry Mumber 20380-11-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,0,3,8 and 0 respectively; the second part has 2 digits, 1 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 20380-11:
(7*2)+(6*0)+(5*3)+(4*8)+(3*0)+(2*1)+(1*1)=64
64 % 10 = 4
So 20380-11-4 is a valid CAS Registry Number.
InChI:InChI=1/C27H46O2/c1-18(17-28)6-5-7-19(2)23-10-11-24-22-9-8-20-16-21(29)12-14-26(20,3)25(22)13-15-27(23,24)4/h8,18-19,21-25,28-29H,5-7,9-17H2,1-4H3/t18-,19-,21+,22+,23-,24+,25+,26+,27-/m1/s1
20380-11-4Relevant articles and documents
Synthesis of side-chain oxysterols and their enantiomers through cross-metathesis reactions of Δ22 steroids
Brownholland, David P.,Covey, Douglas F.
, p. 22 - 31 (2017/03/24)
A synthetic route that utilizes a cross-metathesis reaction with Δ22 steroids has been developed to prepare sterols with varying C-27 side-chains. Natural sterols containing hydroxyl groups at the 25 and (25R)-26 positions were prepared. Enantiomers of cholesterol and (3β,25R)-26-hydroxycholesterol (27-hydroxycholesterol) trideuterated at C-19 were prepared for future biological studies.
Inhibitory effect of oxygenated cholestan-3-ol derivatives on the growth of Mycobacterium tuberculosis
Schmidt, Arndt W.,Choi, Taylor A.,Theumer, Gabriele,Franzblau, Scott G.,Kn?lker, Hans-Joachim
, p. 6111 - 6113 (2013/11/06)
A variety of cholestan-3-ol derivatives, which are oxygenated at different positions of the steroid ring system, were prepared and tested for their inhibition of the Mycobacterium tuberculosis H37Rv strain. Several compounds showed significant antitubercular activities with MIC90 values in the range 4-8 μM and low or non-detectable toxicity against mammalian cells.
Synthesis and biological activity of the (25R)-cholesten-26-oic acids - Ligands for the hormonal receptor DAF-12 in Caenorhabditis elegans
Martin, Rene,Schmidt, Arndt W.,Theumer, Gabriele,Krause, Tilo,Entchev, Eugeni V.,Kurzchalia, Teymuras V.,Knoelker, Hans-Joachim
experimental part, p. 909 - 920 (2009/05/30)
We describe the stereoselective transformation of diosgenin (4a) to (25R)-Δ4-dafachronic acid (1a), (25R)-Δ7- dafachronic acid (2a), and (25R)-cholestenoic acid (3a), which represent potential ligands for the hormonal receptor DAF-12
