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Dehydrolithocholic Acid

(Synonyms: 3-Ketolithocholic Acid) 目录号 : GC47182

Dehydrolithocholic Acid(脱氢石胆酸;3-Oxo-5β-cholanoic acid;3-oxoLCA;DLA)是一种胆汁酸代谢产物,通过与维甲酸受体相关孤儿受体(RORγt)相互作用可抑制‌T辅助细胞17‌(Th17)分化。

Dehydrolithocholic Acid Chemical Structure

Cas No.:1553-56-6

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10mM (in 1mL DMSO)
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1mg
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5mg
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10mg
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25mg
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100mg
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Sample solution is provided at 25 µL, 10mM.

Description

Dehydrolithocholic acid (3-Oxo-5β-cholanoic acid; 3-oxoLCA; DLA) is a bile acid metabolite that inhibits T helper cell 17 (Th17) differentiation by interacting with retinoic acid receptor associated orphan receptor (RORγt) [1]. Bile acids are natural surfactants derived from cholesterol, which are crucial for lipid digestion and glucose metabolism, protecting the intestinal epithelium and endowing the mammalian gut with resistance to pathogens[2]. Dehydrolithocholic acid can be a potential candidate drug for the treatment of inflammatory bowel disease[1].

In vitro, use Dehydrolithocholic acid (5µM; 24 hours) can activate the TGR 5-ERK 1/2 pathway on the surface of bronchial epithelial cells (HBEpC) and increase the expression of cathelicidin in the cells[3]. Use Dehydrolithicholic Acid (20µM; 48 hours) treatment with primary CD4+T cells can inhibit Th 17 differentiation and reduce IL-17 α expression levels, but does not affect T cell differentiation into Th 1 or Th 2 cells[4]. MKN 45 was cultured in serum-free medium and treated with 10ng/mL LIF alone or in combination with Dehydrolithocholic acid (1, 3, 10, and 20μM) to reverse LIF induced cell growth at the lowest concentration of 1μM[5].

In vivo, Jax-B6 mice were fed with fecal slurry containing SFB (segmented filamentous bacteria from C57 BL/6 NTac mice) and fed with a control diet or a diet containing 0.3% (w/w) Dehydrolithocholic acid for one week. Treatment with Dehydrolithocholic acid significantly reduced the percentage of Th17 cells in the mouse gut[4]. The rat MCAO model was treated with Dehydrolithocholic acid (pre ischemic administration; 10mg/kg; ip.), which significantly promoted neuronal death in primary culture after OGD injury by downregulating PLOD 2 levels and increasing PTEN expression[6].

References:
[1] Hang S, Paik D, Yao L, et al. Bile acid metabolites control T(H)17 and T(reg) cell differentiation[J]. Nature, 2019, 576(7785): 143-148.
[2] Cheng W, Zhou X, Jin C, et al. Acid-base transformative HADLA micelles alleviate colitis by restoring adaptive immunity and gut microbiome[J]. J Control Release, 2023, 364: 283-296.
[3] Iwona T Myszor, Kornelia Lapka, et al. Bile acid metabolites enhance expression of cathelicidin antimicrobial peptide in airway epithelium through activation of the TGR5-ERK1/2 pathway. Sci Rep. 2024 Mar 21;14(1):6750.
[4] Saiyu Hang, Donggi Paik, et al. Bile acid metabolites control Th17 and Treg cell differentiation. Nature. 2019 Dec;576(7785):143-148.
[5] Cristina Di Giorgio, Elva Morretta, et al. Bile acids serve as endogenous antagonists of the Leukemia inhibitory factor (LIF) receptor in oncogenesis. Biochem Pharmacol. 2024 May:223:116134.
[6] Xiangyi Kong, Xujin Yao, et al. tDCS Regulates ASBT-3-OxoLCA-PLOD2-PTEN Signaling Pathway to Confer Neuroprotection Following Rat Cerebral Ischemia-Reperfusion Injury. Mol Neurobiol. 2023 Nov;60(11):6715-6730.

Dehydrolithocholic Acid(脱氢石胆酸;3-Oxo-5β-cholanoic acid;3-oxoLCA;DLA)是一种胆汁酸代谢产物,通过与维甲酸受体相关孤儿受体(RORγt)相互作用可抑制‌T辅助细胞17‌(Th17)分化[1]。胆汁酸是胆固醇衍生的天然表面活性剂,对脂质消化和葡萄糖代谢至关重要,保护肠道上皮并赋予对哺乳动物肠道对病原体的抵抗力[2]。Dehydrolithocholic Acid可作为治疗炎症性肠病的潜在候选药物[1]

在体外,使用Dehydrolithocholic Acid(5µM;24h)能够激活支气管上皮细胞(HBEpC)表面TGR 5-ERK 1/2途径,增加细胞中cathelicidin的表达[3]。使用Dehydrolithocholic Acid(20µM;48h)处理原代CD 4+T细胞能够抑制细胞的Th 17分化,降低IL-17 α表达水平,但不影响T细胞分化为Th 1或Th 2细胞[4]。将MKN 45在无血清培养基中培养,单独使用10ng/mL LIF或与Dehydrolithocholic Acid(1、3、10 和 20μM)共同处理细胞,Dehydrolithocholic Acid在1μM的最低浓度下能够逆转LIF诱导的细胞生长[5]

在体内,使用含SFB(分节丝状细菌,来自C57 BL/6 NTac小鼠)的粪浆管饲Jax-B6小鼠,并给这些动物喂食对照饮食或含0.3%(w/w)Dehydrolithocholic Acid的食物一周,Dehydrolithocholic Acid处理显著降低了小鼠回肠Th 17细胞的百分比[4]. 使用Dehydrolithocholic Acid(缺血前给药;10mg/kg;ip.)处理大鼠MCAO 模型,Dehydrolithocholic Acid通过下调PLOD 2水平和增加PTEN表达显著促进了OGD损伤后原代培养的神经元死亡[6]

实验参考方法

Cell experiment [1]:

Cell lines

Primary CD4+T cells from wild-type B6 mice

Preparation Method

A low concentration of TGF-β (0.01ng/ml) was used for Treg culture. DMSO, Dehydrolithocholic acid (20μM) or isoalloLCA (20μM) was added on day 0 and CD4+ T cells were gated for analyses on day 3 for Th17 and Treg, day 5 for Th1 and Th2.

Reaction Conditions

20μM;48h

Applications

Dehydrolithocholic acid can inhibit Th 17 differentiation of cells and reduce IL-17 α expression levels, but does not affect T cell differentiation into Th 1 or Th 2 cells

Animal experiment [1]:

Animal models

C57BL/6J mice from Jackson Laboratories (Jax)

Preparation Method

Jax-B6 mice were fed with fecal slurry containing SFB (segmented filamentous bacteria from C57 BL/6 NTac mice) and fed with a control diet or a diet containing 0.3% (w/w) Dehydrolithocholic acid for one week. The average concentration of Dehydrolithocholic acid in the cecal contents is 24picomol/mg wet weight (approximately equivalent to μM)

Dosage form

0.3% (w/w) dietary administration

Applications

Dehydrolithocholic Acid treatment significantly reduced the percentage of Th17 cells in the ileum

References:
[1]Saiyu Hang, Donggi Paik, et al. Bile acid metabolites control Th17 and Treg cell differentiation. Nature. 2019 Dec;576(7785):143-148.

化学性质

Cas No. 1553-56-6 SDF
别名 3-Ketolithocholic Acid
化学名 (5β)-3-oxo-cholan-24-oic acid
Canonical SMILES C[C@H](CCC(O)=O)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC[C@]4([H])CC(CC[C@]4(C)[C@@]3([H])CC[C@@]21C)=O
分子式 C24H38O3 分子量 374.6
溶解度 DMF: 30 mg/ml,DMF:PBS (pH 7.2) (1:4): 0.20 mg/ml,DMSO: 15 mg/ml,Ethanol: 10 mg/ml 储存条件 Store at -20°C
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1 mM 2.6695 mL 13.3476 mL 26.6951 mL
5 mM 0.5339 mL 2.6695 mL 5.339 mL
10 mM 0.267 mL 1.3348 mL 2.6695 mL
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