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7-keto Cholesterol
本产品不向个人销售，仅用作科学研究，不用于任何人体实验及非科研性质的动物实验。
7-keto Cholesterol图片
CAS NO:566-28-9
包装与价格：
包装价格(元)
5mg电议
10mg电议
50mg电议
100mg电议

产品介绍
7-酮胆固醇，有毒的氧甾醇，抑制胆汁酸生物合成胆固醇 7 α-羟化酶的限速步骤，以及强烈抑制 HMG-CoA 还原酶（胆固醇生物合成中的限速酶）。
Cas No.566-28-9
别名胆甾-3-羟基-5-烯-7-酮,SC-4722
化学名3β-hydroxy-cholest-5-en-7-one
Canonical SMILESCC(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 tipsFor obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.
Shipping ConditionEvaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
产品描述

7-keto Cholesterol is a bioactive sterol and a major oxysterol component of oxidized LDL.[1] [2] It is produced by oxidation of cholesterol via ethanol-mediated lipid peroxidation or photodamage as well as oxidation of 7-dehydro cholesterol by the cytochrome P450 (CYP) isoform CYP7A1. [3][4][5] 7-keto Cholesterol inhibits CYP7A1 (IC50 = ~1 μM).[4] It induces activation and chemotaxis of retinal microglia as well as polarization to a pro-inflammatory state via NLRP3 inflammasome activation in vitro.[6] Intraocular implantation of 7-keto cholesterol coated wafers increases ocular levels of VEGF, IL-1β, and GRO/KC, macrophage infiltration, and neovascularization in rat eye. [7] Levels of 7-keto cholesterol in lipid deposits are increased in a variety of chronic diseases, including atherosclerosis, Alzheimer’s disease, and age-related macular degeneration.

Reference:
[1]. Shentu, T.P., Titushkin, I., Singh, D.K., et al. oxLDL-induced decrease in lipid order of membrane domains is inversely correlated with endothelial stiffness and network formation. American Journal of Physiology.Cell Physiology 299(2), C218-C229 (2010).
[2]. Brown, A.J., Leong, S.l., Dean, R.T., et al. 7-Hydroperoxycholesterol and its products in oxidized low density lipoprotein and human atherosclerotic plaque. Journal of Lipid Research 38, 1730-1745 (1997).
[3]. Rodriguez, I.R., and Fliesler, S.J. Photodamage generates 7-keto- and 7-hydroxycholesterol in the rat retina via a free radical-mediated mechanism. Photochemistry and Photobiology 85(5), 1116-1125 (2009).
[4]. Shinkyo, R., Xu, L., Tallman, K.A., et al. Conversion of 7-dehydrocholesterol to 7-ketocholesterol is catalyzed by human cytochrome P450 7A1 and occurs by direct oxidation without an epoxide intermediate. The Journal of Biological Chemisty 286(38), 33021-33028 (2011).
[5]. Mitic, T., Shave, S., Semjonous, N., et al. 11β-Hydroxysteroid dehydrogenase type 1 contributes to the balance between 7-keto- and 7-hydroxy-oxysterols in vivo. Biochemical Pharmacology 86(1), 146-153 (2013).
[6]. Indaram, M., Ma, W., Zhao, L., et al. 7-Ketocholesterol increases retinal microglial migration, activation, and angiogenicity: A potential pathogenic mechanism underlying age-related macular degeneration. Sci. Rep. 5:9144, (2015).
[7]. Amaral, J., Lee, J.W., Chou, J., et al. 7-Ketocholesterol induces inflammation and angiogenesis in vivo: A novel rat model. PLoS One 8(2), e56099 (2013).