7-keto Cholesterol
(Synonyms: 胆甾-3-羟基-5-烯-7-酮,SC-4722, 7-酮胆固醇) 目录号 : GC40572
7-keto Cholesterol是一种与血管疾病相关的主要氧甾醇，广泛存在于动脉粥样硬化斑块中，具有比胆固醇更强的致动脉粥样硬化作用。
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.
7-keto Cholesterol是一种与血管疾病相关的主要氧甾醇，广泛存在于动脉粥样硬化斑块中，具有比胆固醇更强的致动脉粥样硬化作用[1]。7-keto Cholesterol能够抑制参与胆汁酸和胆固醇合成的限速酶，如胆固醇7α-羟化酶和HMG-CoA还原酶[2]。7-keto Cholesterol具有促炎作用[3]。
在体外，7-keto Cholesterol（50μM）处理人脐静脉内皮细胞（HUVECs）18h，上调了粘附分子（特别是E-选择素）的表达，增强了IL-8 mRNA的表达，增强了NF-κB的活性[4]。7-keto Cholesterol（2.5-40μg/mL）处理人微血管内皮细胞（HMVEC），剂量依赖性地抑制了细胞活力，激活了caspase-3/7、-8和-12[5]。7-keto Cholesterol（5μg/mL）处理血管平滑肌细胞（VSMC）24h，显著增加了白细胞介素-6（IL-6）的表达[6]。
在体内，7-keto Cholesterol（0.1%）添加到饮食中治疗缺血再灌注（IR）损伤小鼠3周，升高了小鼠血浆中7-keto Cholesterol水平，增加了IR后的心肌梗塞面积[7]。
| 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 | |
| 别名 | 胆甾-3-羟基-5-烯-7-酮,SC-4722, 7-酮胆固醇 | ||
| 化学名 | 3β-hydroxy-cholest-5-en-7-one | ||
| 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 | ||
| 分子式 | C27H44O2 | 分子量 | 400.6 |
| 溶解度 | ≤20mg/ml in ethanol; 0.1/ml in DMSO; 2mg/ml in dimethyl formamide | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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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 |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
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Quality Control & SDS
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- Purity: >98.00%
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