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25-Hydroxycholesterol (Synonyms: 25-OH Cholesterol)

Catalog No.GC33860 Copy One-Click Copy Product Info

25-hydroxycholesterol is a side-chain oxysterol produced by cholesterol metabolism and secreted by macrophages in response to Toll-like receptor (TLR) activation.

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25-Hydroxycholesterol Chemical Structure

Cas No.: 2140-46-7

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10mM (in 1mL DMSO)
$38.00
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5mg
$35.00
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10mg
$50.00
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25mg
$98.00
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50mg
$168.00
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100mg
$259.00
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Sample solution is provided at 25 µL, 10mM.



Product has been cited by 2 publications

Description of 25-Hydroxycholesterol

25-hydroxycholesterol is a side-chain oxysterol produced by cholesterol metabolism and secreted by macrophages in response to Toll-like receptor (TLR) activation. 25-hydroxycholesterol effectively and selectively inhibits IgA production by B cells, with an EC50 of approximately 65nM[1]. 25-hydroxycholesterol directly regulates lipid metabolism and inflammatory response in hepatocytes through LXR/SREBP-1 and IκBα/NFκB signaling[2]. 25-hydroxycholesterol has antiviral effects and can also regulate transcriptional responses through AP-1 and act as an inflammatory amplifier [3].

In vitro, 25-hydroxycholesterol (5μM) stimulated mouse macrophages for 18 hours, and RNA expression was analyzed by microarray and seven members of the AP-1 family (Fos, Fosb, Fosl1, Fosl2, Jun, Junb, and Jund) was significantly up-regulated[3]. Treatment of splenic B220+ cells with 25-hydroxycholesterol (250 nM) for 6 days resulted in CSR inhibition, thereby inhibiting IgA secretion, but addition on days 4 and 5 had no effect because of the occurrence of Ig heavy chain site rearrangement[4]. 25-hydroxycholesterol (10−4, 10−5 and 10−6M) dose-dependently inhibits the growth of sparse smooth muscle cells in ethanol vehicles [5].

In vivo, 25-hydroxycholesterol (50 mg/kg; i.p.) upregulates Chop in the lungs of Ch25h–/– mice, as well as the endoplasmic reticulum stress markers BiP and Atf4 [6]. 25-hydroxycholesterol (1.5mg/kg; i.v.) can protect rhesus monkeys from ZIKV virus infection, and 25-hydroxycholesterol (50mg/kg; i.p.) can also prevent ZIKV infection in mice and prevent microcephaly symptoms [7] .

 

References:

[1] McDonald JG, et al. Editorial: 25-Hydroxycholesterol: a new life in immunology[J]. J Leukoc Biol. 2010 Dec;88(6):1071-1072.

[2] Xu L , Bai Q , Rodriguez-Agudo D ,et al. Regulation of Hepatocyte Lipid Metabolism and Inflammatory Response by 25-Hydroxycholesterol and 25-Hydroxycholesterol-3-sulfate[J]. Lipids, 2010, 45(9): 821–832.

[3]Elizabeth S. Gold, Alan H. Diercks, Irina Podolsky, et al. 25-Hydroxycholesterol acts as an amplifier of inflammatory signaling[J]. PNAS, 2014,111 (29):10666-10671.

[4] Bauman D R , Bitmansour A D , Mcdonald J G ,et al.25-Hydroxycholesterol secreted by macrophages in response to Toll-like receptor activation suppresses immunoglobulin A production[J].Proceedings of the National Academy of Sciences, 2009, 106(39):16764-16769.

[5]Cox D C , Comi K , Goldstein A L .Effects of cholesterol and 25-hydroxycholesterol on smooth muscle cell and endothelial cell growth[J].Lipids, 1988, 23(2):85-88.

[6]Madenspacher JH, Morrell ED, McDonald JG, et al. 25-Hydroxycholesterol exacerbates vascular leak during acute lung injury[J]. JCI Insight. 2023  10;8(7):e155448.

[7]Li C , Deng Y Q , Wang S ,et al.25-Hydroxycholesterol Protects Host against Zika Virus Infection and Its Associated Microcephaly in a Mouse Model.[J].Immunity, 2017, 46(3):446.

Protocol of 25-Hydroxycholesterol

Cell experiment [1]:

Cell lines

splenic B220+ cells

Preparation method

Treated cells were diluted to 1×105 cells per well (96-well plate) into medium containing the indicated cytokines (TGF-β1, IL-5, and IL-2) with or without 25-Hydroxycholesterol (250 nM) in triplicate. B cells were grown for an additional 6 days and cells and medium harvested. 

Reaction Conditions

250 nM; 6 days

Applications

25-Hydroxycholesterol inhibited IgA secretion when measured on day 6, but had no effect when added on days 4 and 5.

Animal experiment [2]:

Animal models

Ch25h–/–  mice

Preparation method

mice were treated i.p. with 50 mg/kg 25-Hydroxycholesterol or vehicle (hydroxypropyl beta cyclodextrin) daily for 3 days with sacrifice 4 hours after the final dose. 

Dosage form

50 mg/kg; i.p.

Applications

25-Hydroxycholesterol upregulated Chop and the additional ER stress markers BiP and Atf4 in the lungs of naive Ch25h–/– mice.

References:

[1] Bauman D R , Bitmansour A D , Mcdonald J G ,et al. 25-Hydroxycholesterol secreted by macrophages in response to Toll-like receptor activation suppresses immunoglobulin A production[J].Proceedings of the National Academy of Sciences, 2009, 106(39):16764-16769. 

[2] Madenspacher JH, Morrell ED, McDonald JG, et al. 25-Hydroxycholesterol exacerbates vascular leak during acute lung injury[J]. JCI Insight. 2023  10;8(7):e155448. 

Chemical Properties of 25-Hydroxycholesterol

Cas No. 2140-46-7 SDF
Synonyms 25-OH Cholesterol
Chemical Name cholest-5-ene-3β,25-diol
Canonical SMILES CC(C)(O)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
Formula C27H46O2 M.Wt 402.65
Solubility 20mg/mL in ethanol, 2mg/mL in DMF, 5mg/mL in DMSO (Need ultrasonic) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table of 25-Hydroxycholesterol

Prepare stock solution
1 mg 5 mg 10 mg
1 mM 2.4835 mL 12.4177 mL 24.8355 mL
5 mM 496.7 μL 2.4835 mL 4.9671 mL
10 mM 248.4 μL 1.2418 mL 2.4835 mL
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In vivo Formulation Calculator (Clear solution) of 25-Hydroxycholesterol

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Method for preparing DMSO master liquid: mg drug pre-dissolved in μL DMSO ( Master liquid concentration mg/mL, Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug. )

Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL saline, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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3. All of the above co-solvents are available for purchase on the GlpBio website.

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Average Rating: 5 ★★★★★ (Based on Reviews and 16 reference(s) in Google Scholar.)

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