| CAS |
474-25-9 |
| Chinese Name |
鹅去氧胆酸 |
| English Name |
Chenodeoxycholic Acid |
| Synonyms |
CDCA;Chenodiol |
| Molecular Formula |
C24H40O4 |
| Molecular Weight |
392.57 |
| Solubility |
Soluble in DMSO ≥50mg/mL |
| Purity |
HPLC≥98% |
| Appearance |
White to off-white Solid |
| Storage |
Powder:2-8℃，2 years;Insolvent(Mother Liquid):-20℃，6 months;-80℃，1 year |
| EC |
EINECS 207-481-8 |
| MDL |
MFCD00064142 |
| SMILES |
O=C(O)CC[C@@H](C)[C@]1([H])[C@]2(C)[C@](CC1)([H])[C@]3([H])[C@H](O)C[C@@](C4)([H])[C@@](CC[C@H]4O)(C)[C@]([H])3CC2 |
| InChIKey |
RUDATBOHQWOJDD-BSWAIDMHSA-N |
| InChI |
InChI=1S/C24H40O4/c1-14(4-7-21(27)28)17-5-6-18-22-19(9-11-24(17,18)3)23(2)10-8-16(25)12-15(23)13-20(22)26/h14-20,22,25-26H,4-13H2,1-3H3,(H,27,28)/t14-,15+,16-,17-,18+,19+,20-,22+,23+,24-/m1/s1 |
| PubChem CID |
10133 |
| Target Point |
FXR |
| Passage |
Metabolic Enzyme&Protease |
| Background |
Chenodeoxycholic Acid can activate nuclear receptor FXR, which is related to cholesterol metabolism. The main function is to reduce cholesterol saturation in bile, so as to dissolve and shed cholesterol in stones. |
| Biological Activity |
Chenodeoxycholic Acid 是一种疏水初级胆汁酸，能够活化核受体 FXR，该受体与胆固醇代谢有关[1-5]。 |
| In Vitro |
Chenodeoxycholic acid能够通过激活膜G蛋白偶联受体(TGR5)依赖性途径诱导Cyclin D1蛋白和mRNA表达的显著增加来刺激Ishikawa细胞生长[2]。Chenodeoxycholic acid和Deoxycholic acid(DCA)均抑制11 beta HSD2，IC50值分别为22 mM和38 mM，并引起皮质醇依赖性核转位，并增加盐皮质激素受体(MR)的转录活性[1]。 在培养的人肝母细胞瘤细胞系Hep G2中，Chenodeoxycholic acid诱导LDL受体mRNA水平约4倍，HMG-CoA还原酶和HMG-CoA合酶的mRNA水平增加2倍[3]。Chenodeoxycholic acid处理激活C /EBPβ，如其磷酸化，核积累和HepG2细胞中的表达增加所示。 Chenodeoxycholic acid增强含有-1.65-kb GSTA2启动子的构建体的荧光素酶基因转录，该启动子含有C/EBP反应元件(pGL-1651)。 Chenodeoxycholic acid治疗激活AMP激活蛋白激酶(AMPK)，导致细胞外信号调节激酶1/2(ERK1/2)激活，使用AMPKα和化学抑制剂的显性阴性突变体的实验结果证明[ 5]。布美他尼，BaCl2和囊性纤维化跨膜传导调节因子(CFTR)抑制剂CFTRinh-172对Chenodeoxycholic acid诱导的Isc有抑制作用(≥67％)。腺苷酸环化酶抑制剂MDL12330A使鹅去氧胆酸刺激的Isc降低43％，而鹅去氧胆酸可增加细胞内cAMP浓度[4]。 |
| Cell Experiment |
通过将转染的HEK-293细胞和CHO细胞与相应浓度的胆汁酸一起孵育1小时并用台盼蓝染色来分析细胞活力。根据细胞增殖试剂盒I，使用四唑盐MTT(溴化3-(4，5-二甲基噻唑-2-基)-2，5-二苯基四唑鎓)分析胆汁酸的毒性。对照和胆汁酸之间无显著差异在两个测试中获得经处理的细胞。 |
| Kinase Experiment |
将转染的HEK-293细胞在炭处理的Dulbecco改良的Eagle培养基中培养24小时，用Hanks溶液洗涤一次，并重悬于含有100mM NaCl，1mM MgCl 2，1mM EDTA，1mM EGTA的缓冲液中，250mM蔗糖，20mM Tris-HCl，pH7.4。通过在液氮中冷冻来裂解细胞。测定脱氢酶活性，终体积为20μL，含有适当浓度的胆汁酸，30nCi的[3H]皮质醇和未标记的皮质醇，最终浓度为50nM。通过将细胞裂解物与反应混合物混合来开始反应。或者，从转染的HEK-293细胞制备内质网微粒体，并与含有各种浓度的皮质醇和CDCA的反应混合物一起温育。孵育进行20分钟，并且通过薄层色谱(TLC)测定皮质醇向可的松的转化。由于低转化率下TLC方法的不准确性以及转化率高于60-70％时11βHSD2的终产物抑制，因此仅考虑10％至60％的转化率进行计算。使用曲线拟合程序评估抑制常数IC50。结果表示为平均值±SE，并且包括至少四次独立测量。 |
| Data Literature Source |
[1]. Stauffer AT，et al. Chenodeoxycholic acid and deoxycholic acid inhibit 11 beta-hydroxysteroid dehydrogenase type 2 and cause cortisol-induced transcriptional activation of the mineralocorticoid receptor. J Biol Chem. 2002 Jul 19;277(29):26286-92
[2]. Casaburi I，et al. Chenodeoxycholic acid through a TGR5-dependent CREB signaling activation enhances cyclin D1 expression and promotes human endometrial cancer cell proliferation. Cell Cycle. 2012 Jul 15;11(14):2699-710
[3]. Kawabe Y，et al. The molecular mechanism of the induction of the low density lipoprotein receptor by chenodeoxycholic acid in cultured human cells. Biochem Biophys Res Commun. 1995 Mar 8;208(1):405-11.
[4]. Ao M，et al. Chenodeoxycholic acid stimulates Cl(-) secretion via cAMP signaling and increases cystic fibrosis transmembrane conductance regulator phosphorylation in T84 cells. Am J Physiol Cell Physiol. 2013 Aug 15;305(4):C447-56
[5]. Noh K，et al. Farnesoid X receptor activation by chenodeoxycholic acid induces detoxifying enzymes through AMP-activated protein kinase and extracellular signal-regulated kinase 1/2-mediated phosphorylation of CCAAT/enhancer binding protein β. Drug Metab |
| Unit |
Bottle |
| Specification |
50mg 10mM*1mL in DMSO 100mg |
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