2140-46-7

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.

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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 induc ing apoptosis in CEM cells associated with negative regulation of c-Myc.

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.

25-Hydroxycholesterol (25-HC) is an oxysterol, an early intermediate in the metabolism of cholesterol to bile acids. Studies have shown that 25-HC is closely linked to intracellular cholesterol synthesis and metabolism, and that increased 25-HC synthesis leads to decreased cholesterol synthesis and uptake. 25-HC is also an important component in the control of intracellular cholesterol metabolism, interacting with inflammatory states. In immune function, 25-HC inhibits a wide range of viral infections by regulating the synthesis and distribution of sterols in cells, and is the first line of defence for the lungs. It has a protective effect against tumour growth and metastasis development. In addition, 25-HC and its metabolite 7α, 25-DHC also show beneficial properties by modulating immune cell migration or endothelial/epithelial barrier properties, thus making them involved in atherosclerosis and CNS diseases.

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.

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25-Hydroxycholesterol forms colourless needles from MeOH [Schwartz Tetrahedron Lett 22 4655 1981]. The 3
acetoxy 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.]

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