7-keto Cholesterol (Synonyms: SC-4722) |
| カタログ番号GC40572 |
毒性オキシステロールである 7-ケト コレステロールは、胆汁酸生合成コレステロール 7 α-ヒドロキシラーゼの律速段階を阻害し、HMG-CoA レダクターゼ (コレステロール生合成の律速酵素) を強力に阻害します。
Products are for research use only. Not for human use. We do not sell to patients.
Cas No.: 566-28-9
Sample solution is provided at 25 µL, 10mM.
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7-keto Cholesterol is a major oxysterol associated with vascular disease. It is widely present in atherosclerotic plaques and has a stronger atherogenic effect than cholesterol[1]. 7-keto Cholesterol can inhibit the rate-limiting enzymes involved in the synthesis of bile acids and cholesterol, such as cholesterol 7α-hydroxylase and HMG-CoA reductase[2]. 7-keto Cholesterol has pro-inflammatory effects[3].
In vitro, 7-keto Cholesterol (50μM) treatment of human umbilical vein endothelial cells (HUVECs) for 18h upregulated the expression of adhesion molecules (especially E-selectin), enhanced the expression of IL-8 mRNA, and enhanced the activity of NF-κB[4]. 7-keto Cholesterol (2.5-40μg/mL) treatment of human microvascular endothelial cells (HMVECs) dose-dependently inhibited cell viability and activated caspase-3/7, -8 and -12[5]. Treatment of vascular smooth muscle cells (VSMCs) with 7-keto Cholesterol (5μg/mL) for 24h significantly increased the expression of interleukin-6 (IL-6)[6].
In vivo, 7-keto Cholesterol (0.1%) added to the diet of mice treated with ischemia-reperfusion (IR) injury for 3 weeks increased the level of 7-keto Cholesterol in mouse plasma and increased the size of myocardial infarction after IR[7].
References:
[1] Brahmi F, Vejux A, Sghaier R, et al. Prevention of 7-ketocholesterol-induced side effects by natural compounds[J]. Critical reviews in food science and nutrition, 2019, 59(19): 3179-3198.
[2] Morin R J, Peng S K. Cholesterol oxides in plasma and tissues[J]. Biological effects of cholesterol oxides, 1992: 89-101.
[3] Alba G, Reyes-Quiróz M E, Sáenz J, et al. 7-Keto-cholesterol and 25-hydroxy-1 cholesterol rapidly enhance ROS production in human neutrophils[J]. European journal of nutrition, 2016, 55: 2485-2492.
[4] Tani M, Kamata Y, Deushi M, et al. 7-Ketocholesterol enhances leukocyte adhesion to endothelial cells via p38MAPK pathway[J]. PLoS One, 2018, 13(7): e0200499.
[5] Luthra S, Dong J, Gramajo A L, et al. 7-Ketocholesterol activates caspases-3/7,-8, and-12 in human microvascular endothelial cells in vitro[J]. Microvascular research, 2008, 75(3): 343-350.
[6] Sung S C, Kim K, Lee K A, et al. 7-Ketocholesterol upregulates interleukin-6 via mechanisms that are distinct from those of tumor necrosis factor-α, in vascular smooth muscle cells[J]. Journal of vascular research, 2008, 46(1): 36-44.
[7] Uchikawa T, Matoba T, Kawahara T, et al. Dietary 7-ketocholesterol exacerbates myocardial ischemia–reperfusion injury in mice through monocyte/macrophage-mediated inflammation[J]. Scientific reports, 2022, 12(1): 14902.
| Cell experiment [1]: | |
Cell lines | Human umbilical vein endothelial cells (HUVECs) |
Preparation Method | HUVECs were pretreated with 50μM cholesterol or 7-keto Cholesterol for 18h, followed by 0.1ng/mL TNF-α for an additional 4h. Fresh total protein extracts were isolated from HUVECs using RIPA lysis buffer supplemented with protease and phosphatase inhibitors. |
Reaction Conditions | 50μM; 18h |
Applications | 7-keto Cholesterol upregulated the expression of adhesion molecules, particularly E-selectin, on HUVECs. 7-keto Cholesterol also enhanced the expression of IL-8 mRNA, but had no effect on MCP-1 expression. |
| Animal experiment [2]: | |
Animal models | C57BL/6J mice |
Preparation Method | Mice were fed a normal laboratory diet (CRF-1), WD, or 7KWD for 3 weeks, and then surgery causing myocardial IR was performed. The WD contained 40% fat, 1% cholesterol and 0.5% cholic acid, and the 7KWD contained 40% fat, 0.9% cholesterol, 0.1% 7-keto Cholesterol and 0.5% cholic acid. Plasma was collected for cholesterol, oxysterol, and triglyceride measurements. Total cholesterol, low-density lipoprotein cholesterol, high-density lipoprotein cholesterol, and triglycerides were measured using enzymatic assay kits. |
Dosage form | Add 0.1% 7-keto Cholesterol to diet; p.o. |
Applications | Dietary 7-keto Cholesterol significantly increases plasma oxysterol levels, especially those of 7-ketocholesterol and 7β-hydroxycholesterol. 7-keto Cholesterol increased the expression of MCP-1 and the accumulation of CCR2-positive cells in heart. |
References: | |
| Cas No. | 566-28-9 | SDF | |
| 同義語 | SC-4722 | ||
| Canonical SMILES | CC(C)CCC[C@@H](C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])C(C=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O | ||
| Formula | C27H44O2 | M.Wt | 400.6 |
| 溶解度 | ≤20mg/ml in ethanol; 0.1/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 | 2.4963 mL | 12.4813 mL | 24.9626 mL |
| 5 mM | 0.4993 mL | 2.4963 mL | 4.9925 mL |
| 10 mM | 0.2496 mL | 1.2481 mL | 2.4963 mL |
Step 1: Enter information below (Recommended: An additional animal making an allowance for loss during the experiment)
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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.
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3. All of the above co-solvents are available for purchase on the GlpBio website.
Quality Control & SDS
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- Purity: >98.00%
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Average Rating: 5 (Based on Reviews and 25 reference(s) in Google Scholar.)
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