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7-keto Cholesterol Sale

(Synonyms: 胆甾-3-羟基-5-烯-7-酮,SC-4722) 目录号 : GC40572

A bioactive oxysterol

7-keto Cholesterol Chemical Structure

Cas No.:566-28-9

规格 价格 库存 购买数量
5mg
¥680.00
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10mg
¥1,300.00
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50mg
¥5,111.00
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100mg
¥8,845.00
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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).

Chemical Properties

Cas No. 566-28-9 SDF
别名 胆甾-3-羟基-5-烯-7-酮,SC-4722
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
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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
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Research Update

Interaction of caveolin with 7-ketocholesterol

Atherosclerosis 2001 Nov;159(1):49-55.PMID:11689206DOI:10.1016/s0021-9150(01)00486-5.

Caveolin is an integral membrane protein that interacts with cholesterol in glycosphingolipid-rich rafts at the cell surface. We have examined the interaction of recombinant His-tagged caveolin-1 with cholesterol and 7-keto Cholesterol, the most abundant non-enzymatically formed oxysterol found in oxidised LDL and atheromatous plaque. Our data show that caveolin-1 is able to interact with both sterols. This might have consequences for sterol transport and the signalling properties of cells during atherosclerosis.

Evidence for altered cholesterol metabolism in Huntington's disease post mortem brain tissue

Neuropathol Appl Neurobiol 2016 Oct;42(6):535-46.PMID:26373857DOI:10.1111/nan.12286.

Aims: Cholesterol plays an essential role in membrane structure and function, being especially important in the brain. Alteration of brain cholesterol synthesis and metabolism has been demonstrated in several Huntington's disease (HD) mouse and cell models; however, less is known about these alterations in human tissue. This study aimed to identify alterations to cholesterol synthetic and metabolic pathways in human HD brain tissue. Methods: A broad range of cholesterol synthetic precursors, metabolites and oxidation products were measured by gas chromatography-tandem mass spectrometry in five regions of human post mortem HD brain and compared with age- and sex-matched control tissues. The level of enzymes that regulate cholesterol homeostasis, cholesterol 24-hydroxylase and delta(24)-sterol reductase were investigated by Western blotting and qPCR in putamen. Results: The most significant changes were localized to the putamen, where a 60% decrease in 24(S)-hydroxycholesterol, 30% increase in cholesterol and 100-200% increase in synthetic precursors (lathosterol, zymosterol and desmosterol) was detected. The enzymes cholesterol 24-hydroxylase and delta(24)-sterol reductase were also significantly decreased in HD putamen as compared with control tissues. Free radical-generated cholesterol oxidation products 7-keto Cholesterol and 7β-hydroxycholesterol were also increased by 50-70% in HD putamen. Conclusion: Human HD brain has significantly decreased cholesterol metabolism and disrupted cholesterol homeostasis. Our data also indicate that lipid oxidative stress accompanies HD pathology.