25-hydroxycholesterol
Synonym(s):110816;5-Cholestene-3β,25-diol
- CAS NO.:2140-46-7
- Empirical Formula: C27H46O2
- Molecular Weight: 402.65
- MDL number: MFCD00057815
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-05 19:05:58
What is 25-hydroxycholesterol?
Description
25-hydroxy Cholesterol is an oxysterol. It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection. 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM). 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 μM) and reduces increases in viral protein production in infected Vero cells when used prior to infection. It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in mice expressing human angiotensin-converting enzyme 2 (hACE2), the functional receptor for SARS-CoV-2, in a model of SARS-CoV-2 infection and in a patient with COVID-19, the primarily respiratory disease caused by SARS-CoV-2.
Chemical properties
Off-White Solid
The Uses of 25-hydroxycholesterol
25-Hydroxycholesterol was used to treat mouse neuroblastoma cells to activate the ABCA1 signaling and in studies related to fatty acid metabolism.
The Uses of 25-hydroxycholesterol
An oxygenated derivative of Cholesterol (C432501); an oxysterol. An inhibitor of human immunodeficiency virus replication in vitro. It induces apoptosis in human monocytic cell lines as well as inducing apoptosis in CEM cells associated with negative regulation of c-Myc.
What are the applications of Application
25-Hydroxycholesterol is an activator of caspases and Bcl-2 expressor
Definition
ChEBI: 25-hydroxycholesterol is an oxysterol and a 25-hydroxy steroid. It has a role as a human metabolite. It is functionally related to a cholesterol.
General Description
25-hydroxy-cholesterol is a side chain substituted oxysterol. Avanti′s unique sterol reverses cataracts in mice. Gestwicki′s team ...... settled on compound 29, a steroid found naturally in the bloodstream but not in the lens, which has no blood supply. Mice with age-related and hereditary cataracts received drops in the right eye, whereas the left eye went untreated. After just a few weeks, the treated eye was visibly clearer, says Gestwicki, who conducted the work while at the University of Michigan. Cataract severity is measured on a scale of zero to four, with four being the worst case. On average, mice in the study had about a one-grade improvement in cataract severity after 4 weeks of treatment. Science DOI: 10.1126/science.aad7400 It has been recently shown that activation of a macrophage toll-like receptor (TLR) by microbial antigens induces synthesis of 25-hydroxycholesterol, and that this oxysterol potently suppresses IgA production.
Biochem/physiol Actions
25-Hydroxycholesterol is a side-chain oxysterol that reportedly triggers activation of a number of cholesterol molecules. This triggers their movement from cell membrane to the endoplasmic reticulum (ER). 25-Hydroxycholesterol affects the immune system and has a key role in the pathogenesis of atherosclerosis.
storage
Store at -20°C
Purification Methods
25-Hydroxycholesterol forms colourless needles from MeOH [Schwartz Tetrahedron Lett 22 4655 1981]. The 3acetoxy derivative has m 142-142.8o (from Me2CO) and [] D -40.4o (c 2, CHCl3). The 3,25-diacetoxy derivative has m 119-120.5o (from MeOH) and [] 25D -35.5o (CHCl3). [Dauben & Bradlow J Am Chem Soc 72 4248 1950, Ryer et al. J Am Chem Soc 72 4247 1950, Beilstein 6 IV 6437.]
References
1) Diczialusy (2013),?On the formation and possible biological role of 25-hydroxcholesterol; Biochimie,?95?455 2) McDonald and Russell (2010),?25-hydroxycholesterol: a new life in immunology: J. Leuko. Biol.?88?1071
Properties of 25-hydroxycholesterol
Melting point: | 177-179 °C |
Boiling point: | 513.1±23.0 °C(Predicted) |
Density | 1.03±0.1 g/cm3(Predicted) |
storage temp. | -20°C |
solubility | chloroform: 50 mg/mL, clear, colorless to slightly yellow |
pka | 15.03±0.70(Predicted) |
form | solid |
color | White or pale yellow |
Merck | 13,4846 |
BRN | 3161259 |
Stability: | Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
Safety information for 25-hydroxycholesterol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 Health Hazard GHS08 |
GHS Hazard Statements |
H302:Acute toxicity,oral H312:Acute toxicity,dermal H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H332:Acute toxicity,inhalation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation H373:Specific target organ toxicity, repeated exposure |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 25-hydroxycholesterol
InChIKey | INBGSXNNRGWLJU-ZHHJOTBYSA-N |
Abamectin manufacturer
Varanous Labs Pvt Ltd
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