Lithocholic Acid
Lithocholic Acid (LCA, CAS 434-13-9) is a toxic secondary bile acid that promotes intrahepatic cholestasis (e.g., reducing bile flow and causing accumulation of bile components in the liver and blood) and tumorigenesis. It acts as an FXR antagonist and a PXR/SXR agonist and promotes fat solubilization and absorption. In vitro, it inhibits mammalian DNA polymerase. Lithocholic Acid activates TGR5 and is commonly used to establish animal models of cholestatic liver injury.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 376.57 |
| Cas No. | 434-13-9 |
| Formula | C24H40O3 |
| Synonyms | Lithocholic acid; LCA |
| Solubility | insoluble in H2O; ≥12.95 mg/mL in DMSO; ≥26.6 mg/mL in EtOH with ultrasonic |
| Chemical Name | (4R)-4-[(3R,5R,8R,9S,10S,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid |
| Canonical SMILES | C[C@H](CCC(O)=O)[C@@H](CC1)[C@@](C)(CC2)[C@@H]1[C@H](CC1)[C@H]2[C@@](C)(CC2)[C@H]1C[C@@H]2O |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Cell experiment [1]: | |
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Cell lines |
HL-1 cells |
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Preparation method |
The solubility of this compound in DMSO is > 13 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
50 or 100 μM |
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Applications |
In HL-1 cells, Lithocholic Acid reduced and prevented cardiomyocyte apoptosis at the concentrations of 50 and 100 μM, respectively. In the presences of the pro-apoptotic stimulus, Doxazosin, Lithocholic Acid inhibited hyperphosphorylation of EphA2. In addition, Lithocholic Acid increased the expression of total EphA2. |
| Animal experiment [2]: | |
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Animal models |
Mice |
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Dosage form |
0.125 mg/g; i.p.; b.i.d., for 4 days. |
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Applications |
In PXR-/- mice, Lithocholic Acid resulted in sticky residues. Analysis of the urine revealed that PXR-/- mice showed substantially increased levels of Lithocholic Acid compared with wild-type animals. In addition, wild-type mice treated with Lithocholic Acid in a shorter term showed significant increases in hepatic Cyp3a11 and Oatp2 expression, whereas Lithocholic Acid treatment exhibited no effect on the expression of those genes in PXR-/- mice. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Jehle J, Staudacher I, Wiedmann F, Schweizer P, Becker R, Katus H, Thomas D. Regulation of apoptosis in HL-1 cardiomyocytes by phosphorylation of the receptor tyrosine kinase EphA2 and protection by lithocholic acid. Br J Pharmacol. 2012 Dec;167(7):1563-72. [2]. Staudinger JL, Goodwin B, Jones SA, Hawkins-Brown D, MacKenzie KI, LaTour A, Liu Y, Klaassen CD, Brown KK, Reinhard J, Willson TM, Koller BH, Kliewer SA. The nuclear receptor PXR is a lithocholic acid sensor that protects against liver toxicity. Proc Natl Acad Sci U S A. 2001 Mar 13;98(6):3369-74. |
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| Description | Lithocholic Acid, a bile acid, is an activator of the vitamin D receptor, PXR and FXR. | |||||
| Targets | VDR | PXR | FXR | |||
| IC50 | 29μM(Ki) | |||||
Quality Control & MSDS
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Chemical structure
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