5α,6α-epoxy Cholestanol
(Synonyms: 胆固醇-5Α,6Α-环氧化物,NSC 18176) 目录号 : GC40053
5α,6α-epoxy Cholestanol 是一种胆固醇衍生物，可以通过线粒体中的细胞色素P450酶系催化生成或是在脂质过氧化过程中诱导生成，可调节胆汁酸的生物合成、诱导肿瘤细胞的分化和死亡。
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.
5α,6α-epoxy Cholestanol是一种胆固醇衍生物，可以通过线粒体中的细胞色素P450酶系催化生成或是在脂质过氧化过程中诱导生成，可调节胆汁酸的生物合成、诱导肿瘤细胞的分化和死亡[1]。5α,6α-epoxy Cholestanol是胆固醇在特定条件下氧化生成的一种环氧化合物，是5,6-epoxy Cholestanol的其中一个亚型，具有独特的化学和生物学特性[2]，5α,6α-epoxy Cholestanol 能够抑制胆固醇的7α-羟化，影响胆汁酸的合成，5α,6α-epoxy Cholestanol还具有调节细胞分化、促进肿瘤细胞死亡、激活胆固醇酯化以及调节膜性质等多种生物学功能[3, 4]。
在体外，5α,6α-epoxy Cholestanol（20μM）处理乳腺癌MCF-7 细胞12小时，刺激了MCF-7细胞中肝脏X受体α/β的表达，并上调了三酰甘油的合成[5]。
| 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 | |
| 别名 | 胆固醇-5Α,6Α-环氧化物,NSC 18176 | ||
| 化学名 | (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 | ||
| 分子式 | C27H46O2 | 分子量 | 402.7 |
| 溶解度 | ≤20mg/ml in ethanol; 0.1mg/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 | 2.4832 mL | 12.4162 mL | 24.8324 mL |
| 5 mM | 0.4966 mL | 2.4832 mL | 4.9665 mL |
| 10 mM | 0.2483 mL | 1.2416 mL | 2.4832 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。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Quality Control & SDS
- View current batch:
- Purity: >95.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet