Lithocholic Acid

- Overview
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    Background
    
    Lithocholic acid (LCA) is a toxic secondary bile acid, causing intrahepatic cholestasis, which has tumor-promoting activity.
    In vitro: Among 17 kinds of bile acids with respect to inhibition of mammalian DNA polymerases, only LCA and its derivatives inhibited DNA polymerases, while other bile acids did not show inhibitory effect [1].
    In vivo: Administration of LCA and its conjugates to rodents causes intrahepatic cholestasis, which is a pathogenic state characterized by decreased bile flow and the accumulation of bile constituents in the liver and blood [2].
    Clinical trials: Currently no clinical data are available.
    
    [1] Ogawa A, Murate T, Suzuki M, Nimura Y, Yoshida S. Lithocholic acid, a putative tumor promoter, inhibits mammalian DNA polymerase beta. Jpn J Cancer Res. 1998 Nov;89(11):1154-9.
    [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.
- Properties
  - Categories
    
    Activator of vitamin D receptor, PXR and FXR
    
    Alternative 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
    
    CAS Number
    
    434-13-9
    
    Molecular Formula
    
    C24H40O3
    
    Molecular Weight
    
    376.57
    
    Appearance
    
    A solid
    
    Purity
    
    98.00%
    
    Solubility
    
    insoluble in H2O; ≥12.95 mg/mL in DMSO; ≥26.6 mg/mL in EtOH with ultrasonic
    
    Storage
    
    Store at -20°C
    
    SMILES
    
    O[[email protected]]1C[[email protected]@H]2[[email protected]@](CC1)(C)[[email protected]@H]3[[email protected]@H](CC2)[[email protected]]4[[email protected]@](CC3)(C)[[email protected]@H]([[email protected]](C)CCC(O)=O)CC4
    
    * For Research Use Only
- Reference
  - 1. Anqi Zhao, Liyun Zhang, et al. "Comprehensive Characterization of Bile Acids in Human Biological Samples and Effect of 4-Week Strawberry Intake on Bile Acid Composition in Human Plasm." Metabolites. 2021 Feb 10;11(2):99. PMID:33578858