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Merck
CN

SML0541

Sigma-Aldrich

7α,25-二羟基胆固醇

≥98% (HPLC), powder, GPR183 agonist

别名:

5-胆甾烯-3β,7α,25-三醇

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About This Item

经验公式(希尔记法):
C27H46O3
CAS号:
分子量:
418.65
MDL编号:
UNSPSC代码:
12352211
PubChem化学物质编号:
NACRES:
NA.77

产品名称

7α,25-二羟基胆固醇, ≥98% (HPLC)

质量水平

方案

≥98% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 5 mg/mL (clear solution)

储存温度

2-8°C

SMILES字符串

C[C@H](CCCC(C)(C)O)[C@H]1CC[C@H]2[C@@H]3[C@H](O)C=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C

InChI

1S/C27H46O3/c1-17(7-6-12-25(2,3)30)20-8-9-21-24-22(11-14-27(20,21)5)26(4)13-10-19(28)15-18(26)16-23(24)29/h16-17,19-24,28-30H,6-15H2,1-5H3/t17-,19+,20-,21+,22+,23-,24+,26+,27-/m1/s1

InChI key

BQMSKLCEWBSPPY-IKVTXIKFSA-N

应用

7α,25-二羟基胆固醇已被用作G蛋白偶联受体183(Gpr183)的配体。

生化/生理作用

7α,25-二羟基胆固醇 (7α,25-OHC)是孤儿GPCR受体EBI2 (GPR183)的一种有效选择性内源性配体,其EC50值在皮摩尔范围内。新发现的EBI2-氧甾醇信号通路已被证明在适应性免疫应答中具有重要作用,包括驱动免疫细胞迁移。 体外体内 研究表明,7α,25-OHC可以作为趋化因子指导B细胞、T细胞和树突状细胞的迁移。
7α,25-二羟基胆固醇具有阻断T细胞活化早期步骤的能力。
7α,25-二羟基胆固醇是孤儿GPCR受体EBI2(GPR183)的有效激动剂;可指导免疫细胞迁移。

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable


历史批次信息供参考:

分析证书(COA)

Lot/Batch Number

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C Moog et al.
Immunology, 70(3), 344-350 (1990-07-01)
Oxygenated derivatives of cholesterol are potent immunosuppressors. It has been reported previously that 7,25-dihydroxycholesterol (7,25-OHC), synthesized in the URA31, strongly inhibits the early steps of T-cell activation. So far, the mechanisms underlying this type of effect have been mainly investigated
C Moog et al.
Antiviral chemistry & chemotherapy, 9(6), 491-496 (1998-12-29)
Oxysterols, oxygenated derivatives of cholesterol selected for their cytostatic activity and their inhibitory effect on cholesterol synthesis, have been investigated for their anti-human immunodeficiency virus (HIV) activity in vitro. The three oxysterols tested, 7 beta-hydroxycholesterol (7 beta-OHC), 25-hydroxycholesterol (25-OHC) and
C Moog et al.
International journal of immunopharmacology, 10(5), 511-518 (1988-01-01)
Several oxysterols are powerful immunosuppressors. Among them 7,25-dihydroxycholesterol (7,25-OHC) seems to be particularly interesting. The effect of this synthetic sterol on murine lymphocytes, stimulated by Con A, or by allogeneic or TNP-modified syngeneic lymphocytes, was investigated. The results showed that
Y H Ji et al.
Cancer biochemistry biophysics, 11(1), 45-57 (1990-01-01)
The antitumor effects of two new hydrosoluble derivatives of oxygenated sterols: JB69 and JC40 have been evaluated in vitro on a panel of lymphoma and leukemia cells from human and murine origins. These compounds result from the combination of a
J Zhang et al.
Biochimica et biophysica acta, 1344(3), 241-249 (1997-02-18)
The metabolism of 25-hydroxycholesterol in different cell types was studied and the role of 7 alpha-hydroxylation for the effect of 25-hydroxycholesterol on the activity of HMG-CoA reductase was determined. Human diploid fibroblasts (HDF) and the human melanoma cell line SK-MEL-2

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