5α,6α-epoxy Cholestanol (Synonyms: NSC 18176) |
| Catalog No.GC40053 |
5α,6α-epoxy Cholestanol is a cholesterol derivative that can be catalytically generated by the cytochrome P450 enzyme system in mitochondria or induced during lipid peroxidation. 5α,6α-epoxy Cholestanol can regulate the biosynthesis of bile acids and induce the differentiation and death of tumor cells.
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 1250-95-9
Sample solution is provided at 25 µL, 10mM.
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5α,6α-epoxy Cholestanol is a cholesterol derivative that can be catalytically generated by the cytochrome P450 enzyme system in mitochondria or induced during lipid peroxidation. 5α,6α-epoxy Cholestanol can regulate the biosynthesis of bile acids and induce the differentiation and death of tumor cells[1]. 5α,6α-epoxy Cholestanol is an epoxide compound generated by the oxidation of cholesterol under specific conditions and is one of the subtypes of 5,6-epoxycholestanol, possessing unique chemical and biological properties[2]. 5α,6α-epoxy Cholestanol can inhibit the 7α-hydroxylation of cholesterol, thereby affecting the synthesis of bile acids. Additionally, 5,6α-EC has a variety of biological functions, including regulating cell differentiation, promoting the death of tumor cells, activating cholesterol esterification, and modulating membrane properties[3, 4].
In vitro, treatment of MCF-7 breast cancer cells with 5α,6α-epoxy Cholestanol (20μM) for 12 hours stimulated the expression of liver X receptor α/β in MCF-7 cells and upregulated the synthesis of triglycerides[5].
References:
[1] Poirot M, Silvente-Poirot S. Cholesterol-5,6-epoxides: chemistry, biochemistry, metabolic fate and cancer. Biochimie. 2013 Mar;95(3):622-31.
[2] Bischoff F. Carcinogenic effects of steroids. Adv Lipid Res. 1969;7:165-244.
[3] Black HS, Lo WB. Formation of a carcinogen in human skin irradiated with ultraviolet light. Nature. 1971 Dec 3;234(5327):306-8.
[4] Black HS, Douglas DR. Formation of a carcinogen of natural origin in the etiology of ultraviolet light-induced carcinogenesis. Cancer Res. 1973 Sep;33(9):2094-6.
[5] Segala G, de Medina P, Iuliano L, et al. 5,6-Epoxy-cholesterols contribute to the anticancer pharmacology of tamoxifen in breast cancer cells. Biochem Pharmacol. 2013 Jul 1;86(1):175-89.
| Cell experiment [1]: | |
Cell lines | MCF-7 and MDA-MB-231 cells |
Preparation Method | MCF-7 and MDA-MB-231 cells were grown in RPMI 1640 medium supplemented with 5% fetal bovine serum (FBS) and cultured until passage 30. The cells were then treated with 5,6α-EC (20μM) for 12h. |
Reaction Conditions | 20μM; 12h |
Applications | 5α,6α-epoxy Cholestanol stimulates the expression of hepatic X receptor α/β in MCF-7 cells and upregulates triacylglycerol synthesis. |
References: | |
| Cas No. | 1250-95-9 | SDF | |
| Sinónimos | NSC 18176 | ||
| Chemical Name | (3β,5α,6α)-5,6-epoxy-cholestan-3-ol | ||
| Canonical SMILES | C[C@H](CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C[C@H]4[C@@]5(O4)C[C@@H](O)CC[C@]5(C)[C@@]3([H])CC[C@@]21C | ||
| Formula | C27H46O2 | M.Wt | 402.7 |
| Solubility | ≤20mg/ml in ethanol; 0.1mg/ml in DMSO; 2mg/ml in dimethyl formamide | 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. | ||
| Prepare stock solution | |||
|
1 mg | 5 mg | 10 mg |
| 1 mM | 2.4832 mL | 12.4162 mL | 24.8324 mL |
| 5 mM | 496.6 μL | 2.4832 mL | 4.9665 mL |
| 10 mM | 248.3 μL | 1.2416 mL | 2.4832 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
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μL
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Calculation results:
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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 ddH2O, mix and clarify.
Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.
Note: 1. Please make sure the liquid is clear before adding the next solvent.
2. Be sure to add the solvent(s) in order. You must ensure that the solution obtained, in the previous addition, is a clear solution before proceeding to add the next solvent. Physical methods such as vortex, ultrasound or hot water bath can be used to aid dissolving.
3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Average Rating: 5 (Based on Reviews and 10 reference(s) in Google Scholar.)
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